orthosiphol A

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	9cdb645a-6abe-472b-a28b-9a2e28758776
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name	[(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,10-diacetyloxy-5-benzoyloxy-2-ethenyl-7,10a-dihydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate
SMILES (Canonical)	CC(=O)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(CC3OC(=O)C4=CC=CC=C4)(C)C=C)O)C)OC(=O)C5=CC=CC=C5)OC(=O)C)O)(C)C
SMILES (Isomeric)	CC(=O)O[C@@H]1C[C@@H]2[C@@]([C@@H]3[C@@]1(C(=O)[C@@](C[C@H]3OC(=O)C4=CC=CC=C4)(C)C=C)O)([C@H]([C@H]([C@H](C2(C)C)O)OC(=O)C)OC(=O)C5=CC=CC=C5)C
InChI	InChI=1S/C38H44O11/c1-8-36(6)20-25(48-32(42)23-15-11-9-12-16-23)29-37(7)26(19-27(46-21(2)39)38(29,45)34(36)44)35(4,5)30(41)28(47-22(3)40)31(37)49-33(43)24-17-13-10-14-18-24/h8-18,25-31,41,45H,1,19-20H2,2-7H3/t25-,26+,27-,28+,29-,30-,31+,36+,37+,38+/m1/s1
InChI Key	HIBFBUSEUDRQMX-OFUWLHILSA-N
Popularity	3 references in papers

Physical and Chemical Properties

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Molecular Formula	C₃₈H₄₄O₁₁
Molecular Weight	676.70 g/mol
Exact Mass	676.28836222 g/mol
Topological Polar Surface Area (TPSA)	163.00 Å²
XlogP	5.30
Atomic LogP (AlogP)	4.24
H-Bond Acceptor	11
H-Bond Donor	2
Rotatable Bonds	7

Synonyms

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CHEMBL508620

SCHEMBL1990731

HIBFBUSEUDRQMX-OFUWLHILSA-

AKOS040762796

142741-25-1

[(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,10-diacetyloxy-5-benzoyloxy-2-ethenyl-7,10a-dihydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate

InChI=1/C38H44O11/c1-8-36(6)20-25(48-32(42)23-15-11-9-12-16-23)29-37(7)26(19-27(46-21(2)39)38(29,45)34(36)44)35(4,5)30(41)28(47-22(3)40)31(37)49-33(43)24-17-13-10-14-18-24/h8-18,25-31,41,45H,1,19-20H2,2-7H3/t25-,26+,27-,28+,29-,30-,31+,36+,37+,38+/m1/s1

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	-	0.8209	82.09%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7196	71.96%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8730	87.30%
OATP1B3 inhibitior	+	0.8203	82.03%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9858	98.58%
P-glycoprotein inhibitior	+	0.8462	84.62%
P-glycoprotein substrate	-	0.6152	61.52%
CYP3A4 substrate	+	0.6688	66.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	+	0.5260	52.60%
CYP2C9 inhibition	-	0.8244	82.44%
CYP2C19 inhibition	-	0.8391	83.91%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.6953	69.53%
CYP2C8 inhibition	+	0.6561	65.61%
CYP inhibitory promiscuity	-	0.9041	90.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.5696	56.96%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.8962	89.62%
Skin irritation	-	0.7073	70.73%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6944	69.44%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.6724	67.24%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5963	59.63%
Acute Oral Toxicity (c)	III	0.6242	62.42%
Estrogen receptor binding	+	0.7525	75.25%
Androgen receptor binding	+	0.6774	67.74%
Thyroid receptor binding	+	0.6370	63.70%
Glucocorticoid receptor binding	+	0.7445	74.45%
Aromatase binding	+	0.6085	60.85%
PPAR gamma	+	0.7095	70.95%
Honey bee toxicity	-	0.6938	69.38%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.67%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.43%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.28%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.26%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.84%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.68%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.08%	94.62%
CHEMBL340	P08684	Cytochrome P450 3A4	91.53%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.96%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.49%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.25%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.12%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.25%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.22%	96.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.47%	82.69%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.09%	83.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.48%	97.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.97%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.46%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.34%	91.07%
CHEMBL5028	O14672	ADAM10	81.09%	97.50%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.00%	97.53%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Angelica ursina

Ardisia macrocarpa

Asplenium nidus

Astragalus laxmannii subsp. laxmannii

Celmisia petriei

Cenchrus americanus

Chlorophytum malayense