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C-28 aldehyde of sipholenol A

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

Canonical Smiles	O=CC1=CCC2C(C(C1CC[C@H]1[C@@](C)(O)CC[C@@H]3[C@]1(C)CC[C@H](C(O3)(C)C)O)(C)C)CC[C@@]2(C)O
InChI	InChI=1S/C30H50O5/c1-26(2)20(19(18-31)8-9-22-21(26)12-16-29(22,6)33)10-11-23-28(5)15-13-24(32)27(3,4)35-25(28)14-17-30(23,7)34/h8,18,20-25,32-34H,9-17H2,1-7H3/t20?,21?,22?,23-,24-,25-,28-,29-,30+/m1/s1
InChIKey	BDNMFPOVAWCGRX-NXHAIPTASA-N
Formula	C₃₀H₅₀O₅
HBA	5
HBD	3
MW	490.73
Rotatable Bonds	4
TPSA	86.99
LogP	5.2
Number Rings	4
Number Aromatic Rings	0
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.9
Exact Mass	490.37
Number of Lipinski Rule Violations	1

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

Showing of synonyms

Jain S, Laphookhieo S, et al. (2007). Reversal of P-glycoprotein-mediated multidrug resistance by sipholane triterpenoids.. Journal of Natural Products,2007,70(6),928-931. [View] [PubMed]

Pubchem: 16736856

Nmrshiftdb2: 70065750

Chembl: CHEMBL226197

No compound-protein relationship available.

SMILES: C1CCC(C12)CC(C=CC2)CCC3CCCC(C34)OCCCC4

Level: 1

Mol. Weight: 490.73 g/mol

SMILES: C1CCCC(C12)OCCCC2

Level: 0

Mol. Weight: 490.73 g/mol

SMILES: C1CCC(C12)CCC=CC2

Level: 0

Mol. Weight: 490.73 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.95
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.76
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.85

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.73
Plasma Protein Binding: 62.58
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: Non-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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.69
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.78
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.21
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.56
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -154.08
Rat (Acute): 5.31
Rat (Chronic Oral): 1.46
Fathead Minnow: 3.85
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: 492.88
Hydration Free Energy: -3.21
Log(D) at pH=7.4: 4.31
Log(P): 4.91
Log S: -5.07
Log(Vapor Pressure): -8.5
Melting Point: 160.06
pKa Acid: 8.31
pKa Basic: 7.29

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.9392
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.9392
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7864
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7864
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7771
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7771
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7759
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7759
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7751
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7751
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7562
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7562
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7529
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7529
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7514
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7514
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7298
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7298
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7234
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7234
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7228
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7228
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7179
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7179
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7150
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7150
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7140
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7140
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7122
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7122
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7115
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7115

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