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Sipholenol J

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

Canonical Smiles	C[C@@H]1C(=O)C[C@H]2[C@H](/C/1=C/C[C@@H]1[C@@H](O)CC[C@H]3[C@@]1(C)CC[C@@H](C(O3)(C)C)O)C(C)(C)CC[C@H]2O
InChI	InChI=1S/C28H46O5/c1-16-17(25-18(15-22(16)31)20(29)11-13-26(25,2)3)7-8-19-21(30)9-10-24-28(19,6)14-12-23(32)27(4,5)33-24/h7,16,18-21,23-25,29-30,32H,8-15H2,1-6H3/b17-7+/t16-,18+,19+,20+,21-,23-,24-,25-,28-/m0/s1
InChIKey	ABGNAICVJIMFGN-XVOYISEWSA-N
Formula	C₂₈H₄₆O₅
HBA	5
HBD	3
MW	462.67
Rotatable Bonds	2
TPSA	86.99
LogP	4.42
Number Rings	4
Number Aromatic Rings	0
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.89
Exact Mass	462.33
Number of Lipinski Rule Violations	0

#	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: 44234696

Cas: 1169792-78-2

Zinc: ZINC000101840339

Nmrshiftdb2: 70095375

Chembl: CHEMBL563310

No compound-protein relationship available.

SMILES: C1CCCC(C12)CC(=O)CC2=CCC3CCCC(C34)OCCCC4

Level: 1

Mol. Weight: 462.67 g/mol

SMILES: C=C1CC(=O)CC(C12)CCCC2

Level: 0

Mol. Weight: 462.67 g/mol

SMILES: C1CCCC(C12)OCCCC2

Level: 0

Mol. Weight: 462.67 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.53
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.72
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.0
Plasma Protein Binding: 77.55
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: 10.33
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.13
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.83
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.82
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -78.33
Rat (Acute): 4.24
Rat (Chronic Oral): 2.08
Fathead Minnow: 3.86
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 478.22
Hydration Free Energy: -2.68
Log(D) at pH=7.4: 3.38
Log(P): 4.48
Log S: -4.84
Log(Vapor Pressure): -8.74
Melting Point: 164.49
pKa Acid: 8.18
pKa Basic: 5.96

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8618
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8618
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8254
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8254
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8203
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8203
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8174
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8174
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7935
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7935
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7806
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7806
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7667
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7667
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7488
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7488
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7462
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7462
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7341
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7341
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7317
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7317
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7164
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7164
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7059
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7059
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7032
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7032
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7009
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7009

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