(1R,3aS,5aS,5bR,9R,10R,11aR)-9,10-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Details

• Internal ID: 3bf6ef88-7884-4222-bae4-f53d70780d6b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,3aS,5aS,5bR,9R,10R,11aR)-9,10-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• SMILES (Canonical): CC(=C)C1CCC2(C1C3=CCC4C(C3(CC2)C)(CCC5C4(CC(C(C5(C)C)O)O)C)C)C(=O)O
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@]2(C1C3=CCC4[C@]([C@@]3(CC2)C)(CCC5[C@@]4(C[C@H]([C@@H](C5(C)C)O)O)C)C)C(=O)O
• InChI: InChI=1S/C30H46O4/c1-17(2)18-10-13-30(25(33)34)15-14-28(6)19(23(18)30)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h8,18,20-24,31-32H,1,9-16H2,2-7H3,(H,33,34)/t18-,20+,21?,22?,23?,24-,27-,28+,29+,30-/m0/s1
• InChI Key: YVFUWFRLVWFNLF-LAYMWGLGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₄
• Molecular Weight: 470.70 g/mol
• Exact Mass: 470.33960994 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 5.98
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• (1R,3aS,5aS,5bR,9R,10R,11aR)-9,10-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-9,10-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• DTXSID80941301
• 2,3-Dihydroxylupa-12,20(29)-dien-28-oic acid
• (1R,3aS,5aS,5bR,9R,10R,11aR)-9,10-dihydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	-	0.5619	56.19%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8355	83.55%
OATP2B1 inhibitior	-	0.7129	71.29%
OATP1B1 inhibitior	+	0.8790	87.90%
OATP1B3 inhibitior	-	0.3770	37.70%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6071	60.71%
BSEP inhibitior	+	0.7980	79.80%
P-glycoprotein inhibitior	-	0.8500	85.00%
P-glycoprotein substrate	-	0.6965	69.65%
CYP3A4 substrate	+	0.6498	64.98%
CYP2C9 substrate	-	0.8262	82.62%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.8811	88.11%
CYP2C9 inhibition	-	0.8651	86.51%
CYP2C19 inhibition	-	0.8654	86.54%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.8776	87.76%
CYP2C8 inhibition	+	0.5505	55.05%
CYP inhibitory promiscuity	-	0.9542	95.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6735	67.35%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9238	92.38%
Skin irritation	+	0.6729	67.29%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4427	44.27%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.6725	67.25%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5391	53.91%
Acute Oral Toxicity (c)	III	0.5877	58.77%
Estrogen receptor binding	+	0.7323	73.23%
Androgen receptor binding	+	0.7249	72.49%
Thyroid receptor binding	+	0.6122	61.22%
Glucocorticoid receptor binding	+	0.7578	75.78%
Aromatase binding	+	0.6904	69.04%
PPAR gamma	+	0.5324	53.24%
Honey bee toxicity	-	0.8518	85.18%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.47%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.97%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.61%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.13%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.46%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.41%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.90%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.30%	93.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.14%	93.03%

Plants that contains it

• Alphitonia excelsa
• Alphitonia whitei
• Chaenomeles sinensis
• Dryobalanops aromatica
• Eucalyptus camaldulensis
• Plumeria obtusa
• Prunus dulcis
• Rosa davurica
• Rosa woodsii
• Syzygium sandwicense
• Ziziphus jujuba
• Ziziphus jujuba var. spinosa
• Ziziphus mauritiana

Cross-Links

• PubChem: 470606
• LOTUS: LTS0004577
• wikiData: Q105365308