NCBI Taxonomy: 1136792

Rolandrinae (ncbi_taxid: 1136792)

found 42 associated metabolites at subtribe taxonomy rank level.

Ancestor: Vernonieae

Child Taxonomies: Rolandra, Spiracantha, Acilepidopsis

Vanillin

Vanillin melting point standard, Pharmaceutical Secondary Standard; Certified Reference Material

C8H8O3 (152.0473418)


Vanillin, also known as vanillaldehyde or lioxin, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is used by the food industry as well as ethylvanillin. Vanillin exists in all living species, ranging from bacteria to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns, ryes, and sherries and in a lower concentration in beers, rums, and oats. Vanillin has also been detected, but not quantified, in several different foods, such as gooseberries, other bread, brazil nuts, shea tree, and ohelo berries. This could make vanillin a potential biomarker for the consumption of these foods. Vanillin is a potentially toxic compound. Synthetic vanillin, instead of natural Vanillin extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. Vanillin is the primary component of the extract of the Vanillin bean. Because of the scarcity and expense of natural Vanillin extract, there has long been interest in the synthetic preparation of its predominant component. Artificial Vanillin flavoring is a solution of pure vanillin, usually of synthetic origin. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Vanillin appears as white or very slightly yellow needles. Vanillin is a member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. It has a role as a plant metabolite, an anti-inflammatory agent, a flavouring agent, an antioxidant and an anticonvulsant. It is a member of phenols, a monomethoxybenzene and a member of benzaldehydes. Vanillin is a natural product found in Ficus erecta var. beecheyana, Pandanus utilis, and other organisms with data available. Vanillin is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. It is used by the food industry as well as ethylvanillin.Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. (Wiki). Vanillin is a metabolite found in or produced by Saccharomyces cerevisiae. Constituent of vanilla (Vanilla subspecies) and many other plants, e.g. Peru balsam, clove bud oil. Widely used flavouring agent especies in cocoa products. obtained from spent wood-pulp liquors. Vanillin is found in many foods, some of which are pomes, elderberry, common cabbage, and dock. A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; ML_ID 59 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

   

Lupeol

(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol

C30H50O (426.386145)


Lupeol is a pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. It has a role as an anti-inflammatory drug and a plant metabolite. It is a secondary alcohol and a pentacyclic triterpenoid. It derives from a hydride of a lupane. Lupeol has been investigated for the treatment of Acne. Lupeol is a natural product found in Ficus auriculata, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

   

Epimagnolin

1-(3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-hexahydrofuro[3,4-c]furan

C23H28O7 (416.1834938)


   

Lupeol acetate

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-yl acetate

C32H52O2 (468.3967092)


   

Lupeol acetate

Acetic acid (1R,3aR,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-yl ester

C32H52O2 (468.3967092)


Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1]. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].

   

Vanillin

4-hydroxy-3-methoxybenzaldehyde

C8H8O3 (152.0473418)


CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3579; ORIGINAL_PRECURSOR_SCAN_NO 3578 D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3566; ORIGINAL_PRECURSOR_SCAN_NO 3561 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3549; ORIGINAL_PRECURSOR_SCAN_NO 3546 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3560; ORIGINAL_PRECURSOR_SCAN_NO 3556 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3573; ORIGINAL_PRECURSOR_SCAN_NO 3570 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3577; ORIGINAL_PRECURSOR_SCAN_NO 3575 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.504 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.503 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.500 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

   

lupeol

Lup-20(29)-en-3.beta.-ol

C30H50O (426.386145)


D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

   

caryophyllene

(-)-beta-Caryophyllene

C15H24 (204.18779039999998)


A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

   

Cyperene

3H-3a,7-Methanoazulene,2,4,5,6,7,8-hexahydro-1,4,9,9-tetramethyl-, (3aR,4R,7R)-

C15H24 (204.18779039999998)


   

Lupeol acetate

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-yl acetate

C32H52O2 (468.3967092)


Lupeyl acetate, also known as lupeyl acetic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Lupeyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Lupeyl acetate can be found in burdock, date, and fig, which makes lupeyl acetate a potential biomarker for the consumption of these food products. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1]. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].

   

(4r,6r,8r)-8-(acetyloxy)-3-(ethoxymethyl)-6-hydroxy-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

(4r,6r,8r)-8-(acetyloxy)-3-(ethoxymethyl)-6-hydroxy-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C23H30O8 (434.194058)


   

8-(acetyloxy)-3-[(acetyloxy)methyl]-10-hydroxy-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylbut-2-enoate

8-(acetyloxy)-3-[(acetyloxy)methyl]-10-hydroxy-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylbut-2-enoate

C24H30O9 (462.18897300000003)


   

(3s,3as,6ar,9ar,9bs)-3-methyl-6,9-dimethylidene-octahydroazuleno[4,5-b]furan-2,8-dione

(3s,3as,6ar,9ar,9bs)-3-methyl-6,9-dimethylidene-octahydroazuleno[4,5-b]furan-2,8-dione

C15H18O3 (246.1255878)


   

(4r,6s,8s)-8-(acetyloxy)-6-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

(4r,6s,8s)-8-(acetyloxy)-6-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C21H26O8 (406.1627596)


   

(1s,2s,4r,6r,7e,10s)-6-(acetyloxy)-12-[(acetyloxy)methyl]-4,8-dimethyl-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradeca-7,11-dien-10-yl 2-methylpropanoate

(1s,2s,4r,6r,7e,10s)-6-(acetyloxy)-12-[(acetyloxy)methyl]-4,8-dimethyl-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradeca-7,11-dien-10-yl 2-methylpropanoate

C23H30O9 (450.18897300000003)


   

8-(acetyloxy)-3-[(acetyloxy)methyl]-10-hydroxy-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

8-(acetyloxy)-3-[(acetyloxy)methyl]-10-hydroxy-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C23H28O9 (448.17332380000005)


   

8-(acetyloxy)-3-(ethoxymethyl)-6-hydroxy-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

8-(acetyloxy)-3-(ethoxymethyl)-6-hydroxy-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C23H30O8 (434.194058)


   

(1s,2r,4r,6r,7e,10s)-6-(acetyloxy)-12-[(acetyloxy)methyl]-4,8-dimethyl-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradeca-7,11-dien-10-yl 2-methylprop-2-enoate

(1s,2r,4r,6r,7e,10s)-6-(acetyloxy)-12-[(acetyloxy)methyl]-4,8-dimethyl-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradeca-7,11-dien-10-yl 2-methylprop-2-enoate

C23H28O9 (448.17332380000005)


   

9,14-dimethyl-5-methylidene-3,12-dioxatricyclo[7.5.0.0²,⁶]tetradeca-10,13-dien-4-one

9,14-dimethyl-5-methylidene-3,12-dioxatricyclo[7.5.0.0²,⁶]tetradeca-10,13-dien-4-one

C15H18O3 (246.1255878)


   

(4r,6s,8s)-8-(acetyloxy)-3-(ethoxymethyl)-6-hydroxy-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

(4r,6s,8s)-8-(acetyloxy)-3-(ethoxymethyl)-6-hydroxy-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C23H30O8 (434.194058)


   

6-(acetyloxy)-12-[(acetyloxy)methyl]-4,8-dimethyl-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradeca-7,11-dien-10-yl 2-methylprop-2-enoate

6-(acetyloxy)-12-[(acetyloxy)methyl]-4,8-dimethyl-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradeca-7,11-dien-10-yl 2-methylprop-2-enoate

C23H28O9 (448.17332380000005)


   

(1s,2s,6s,9s)-9,14-dimethyl-5-methylidene-3,12-dioxatricyclo[7.5.0.0²,⁶]tetradeca-10,13-dien-4-one

(1s,2s,6s,9s)-9,14-dimethyl-5-methylidene-3,12-dioxatricyclo[7.5.0.0²,⁶]tetradeca-10,13-dien-4-one

C15H18O3 (246.1255878)


   

(4s,8s,10s)-8-(acetyloxy)-10-hydroxy-3-(methoxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

(4s,8s,10s)-8-(acetyloxy)-10-hydroxy-3-(methoxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C22H28O8 (420.1784088)


   

8-(acetyloxy)-10-hydroxy-3-(methoxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

8-(acetyloxy)-10-hydroxy-3-(methoxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C22H28O8 (420.1784088)


   

(4r,8r,10s)-8-(acetyloxy)-10-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

(4r,8r,10s)-8-(acetyloxy)-10-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C21H26O8 (406.1627596)


   

(4r,8r,10s)-8-(acetyloxy)-3-[(acetyloxy)methyl]-10-hydroxy-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

(4r,8r,10s)-8-(acetyloxy)-3-[(acetyloxy)methyl]-10-hydroxy-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C23H28O9 (448.17332380000005)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.386145)


   

(2r,5s,10s)-6,10-dimethyl-2-(prop-1-en-2-yl)spiro[4.5]dec-6-ene

(2r,5s,10s)-6,10-dimethyl-2-(prop-1-en-2-yl)spiro[4.5]dec-6-ene

C15H24 (204.18779039999998)


   

3-methyl-6,9-dimethylidene-octahydroazuleno[4,5-b]furan-2,8-dione

3-methyl-6,9-dimethylidene-octahydroazuleno[4,5-b]furan-2,8-dione

C15H18O3 (246.1255878)


   

(1s,2s,6s,9r)-9,14-dimethyl-5-methylidene-3,12-dioxatricyclo[7.5.0.0²,⁶]tetradeca-10,13-dien-4-one

(1s,2s,6s,9r)-9,14-dimethyl-5-methylidene-3,12-dioxatricyclo[7.5.0.0²,⁶]tetradeca-10,13-dien-4-one

C15H18O3 (246.1255878)


   

8-(acetyloxy)-6-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

8-(acetyloxy)-6-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,7h,8h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C21H26O8 (406.1627596)


   

6-(acetyloxy)-12-[(acetyloxy)methyl]-4,8-dimethyl-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradeca-7,11-dien-10-yl 2-methylpropanoate

6-(acetyloxy)-12-[(acetyloxy)methyl]-4,8-dimethyl-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradeca-7,11-dien-10-yl 2-methylpropanoate

C23H30O9 (450.18897300000003)


   

8-(acetyloxy)-10-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

8-(acetyloxy)-10-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C21H26O8 (406.1627596)


   

(4s,8r,10s)-8-(acetyloxy)-10-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

(4s,8r,10s)-8-(acetyloxy)-10-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C21H26O8 (406.1627596)


   

(4r,8r,10s)-8-(acetyloxy)-3-[(acetyloxy)methyl]-10-hydroxy-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate

(4r,8r,10s)-8-(acetyloxy)-3-[(acetyloxy)methyl]-10-hydroxy-6,10-dimethyl-2-oxo-4h,5h,8h,9h-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate

C24H30O9 (462.18897300000003)