orthosiphol B

Details

• Internal ID: 0ed6e4cb-441d-4842-a454-925482150cee
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-7,10-diacetyloxy-5-benzoyloxy-2-ethenyl-6,10a-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)O)OC(=O)C)(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)OC(=O)C)O)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(47-22(3)40)28(41)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: BXKNTIMTKVZYDP-OFUWLHILSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

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

Synonyms

• CHEMBL509129
• SCHEMBL1996101
• BXKNTIMTKVZYDP-OFUWLHILSA-
• AKOS040762798
• 144078-08-0
• 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(47-22(3)40)28(41)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

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	-	0.8035	80.35%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7196	71.96%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8937	89.37%
OATP1B3 inhibitior	+	0.8203	82.03%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9689	96.89%
P-glycoprotein inhibitior	+	0.8555	85.55%
P-glycoprotein substrate	-	0.5843	58.43%
CYP3A4 substrate	+	0.6795	67.95%
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	+	0.6707	67.07%
CYP inhibitory promiscuity	-	0.9041	90.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.5696	56.96%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.8985	89.85%
Skin irritation	-	0.7073	70.73%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7574	75.74%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.6724	67.24%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5564	55.64%
Acute Oral Toxicity (c)	III	0.6242	62.42%
Estrogen receptor binding	+	0.7542	75.42%
Androgen receptor binding	+	0.6757	67.57%
Thyroid receptor binding	+	0.6418	64.18%
Glucocorticoid receptor binding	+	0.7530	75.30%
Aromatase binding	+	0.6041	60.41%
PPAR gamma	+	0.7277	72.77%
Honey bee toxicity	-	0.6765	67.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
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	96.34%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	96.22%	90.17%
CHEMBL1951	P21397	Monoamine oxidase A	95.87%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.75%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.70%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.76%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.94%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	91.38%	91.19%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.88%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.77%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.68%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.35%	95.50%
CHEMBL2535	P11166	Glucose transporter	86.30%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.24%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.59%	100.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.54%	83.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.01%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.90%	96.95%
CHEMBL5028	O14672	ADAM10	82.30%	97.50%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.48%	97.53%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.01%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.14%	85.14%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Catoferia spicata
• Celmisia petriei
• Cenchrus americanus
• Chlorophytum malayense
• Cirsium helenioides
• Clausena indica
• Clusia torresii
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Ferula assa-foetida
• Gentiana olivieri
• Handroanthus guayacan
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus
• Orthosiphon aristatus var. aristatus
• Oryza sativa
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Populus tremula
• Primula veris
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Senecio integerrimus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Ulmus laciniata
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 15385859
• NPASS: NPC237549
• ChEMBL: CHEMBL509129
• LOTUS: LTS0044083
• wikiData: Q104399586