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(2S,4aS,5S,6R,8aS)-5-(2-((1S,3aS,5R,8aS,Z)-1-hydroxy-1,4,4,6-tetramethyl-1,2,3,3a,4,5,8,8a-octahydroazulen-5-yl)-ethyl)-4a,6-dimethyloctahydro-2H-chromene-2,6-diol

Family: Animalia - Callyspongiidae
Kingdom: Animalia
Class: Terpenoid
- Subclass: Triterpene

Canonical Smiles	O[C@@H]1CC[C@@]2([C@@H](O1)CC[C@@]([C@H]2CCC1C(=CC[C@H]2[C@@H](C1(C)C)CC[C@]2(C)O)C)(C)O)C
InChI	InChI=1S/C27H46O4/c1-17-7-8-20-19(11-15-26(20,5)29)24(2,3)18(17)9-10-21-25(4)14-13-23(28)31-22(25)12-16-27(21,6)30/h7,18-23,28-30H,8-16H2,1-6H3/t18?,19-,20-,21-,22-,23-,25-,26-,27+/m0/s1
InChIKey	QHUWGQUBUQPIRE-RJELFLFTSA-N
Formula	C₂₇H₄₆O₄
HBA	4
HBD	3
MW	434.66
Rotatable Bonds	3
TPSA	69.92
LogP	5.2
Number Rings	4
Number Aromatic Rings	0
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.93
Exact Mass	434.34
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Callyspongia siphonella	Callyspongiidae	Animalia	469330

Showing of synonyms

Jain S, Abraham I, et al. (2009). Sipholane triterpenoids: Chemistry, reversal of ABCB1/P-glycoprotein-mediated multidrug resistance, and pharmacophore modeling.. Journal of Natural Products,2009,72(7),1291-1298. [View] [PubMed]

Pubchem: 162899510

No compound-protein relationship available.

SMILES: C1CCC(C12)CC(C=CC2)CCC3CCCC(C34)OCCC4

Level: 1

Mol. Weight: 434.66 g/mol

SMILES: C1CCOC(C12)CCCC2

Level: 0

Mol. Weight: 434.66 g/mol

SMILES: C1CCC(C12)CCC=CC2

Level: 0

Mol. Weight: 434.66 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.73
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.68
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.44

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.96
Plasma Protein Binding: 71.86
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.08
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.32
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.62
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.6
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -33.1
Rat (Acute): 2.62
Rat (Chronic Oral): 1.6
Fathead Minnow: 3.84
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 452.83
Hydration Free Energy: -4.73
Log(D) at pH=7.4: 4.22
Log(P): 5.29
Log S: -5.78
Log(Vapor Pressure): -8.23
Melting Point: 172.62
pKa Acid: 10.51
pKa Basic: 7.96

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8126
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8126
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7608
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7608

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