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Siphonellinol C-23-hydroperoxide

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

Canonical Smiles	OOC(/C=C/C[C@]1(C)[C@H](O)CCC(=C1CC[C@@H]1[C@](C)(O)CC[C@H]2[C@@]1(C)CC[C@@H](C(O2)(C)C)O)C)(C)C
InChI	InChI=1S/C30H52O6/c1-20-10-13-24(32)28(6,17-9-16-26(2,3)36-34)21(20)11-12-22-29(7)18-14-23(31)27(4,5)35-25(29)15-19-30(22,8)33/h9,16,22-25,31-34H,10-15,17-19H2,1-8H3/b16-9+/t22-,23-,24+,25-,28-,29-,30+/m0/s1
InChIKey	KKUBOUCKYPCBMT-CDMQMTAESA-N
Formula	C₃₀H₅₂O₆
HBA	6
HBD	4
MW	508.74
Rotatable Bonds	7
TPSA	99.38
LogP	5.94
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	36
Formal Charge	0
Fraction CSP3	0.87
Exact Mass	508.38
Number of Lipinski Rule Violations	2

#	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: 44234958

Zinc: ZINC000096903560

Nmrshiftdb2: 70095374

Chembl: CHEMBL558129

No compound-protein relationship available.

SMILES: C1CCCC=C1CCC2CCCC(C23)OCCCC3

Level: 1

Mol. Weight: 508.74 g/mol

SMILES: C1CCCC(C12)OCCCC2

Level: 0

Mol. Weight: 508.74 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 508.74 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.76
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.800
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.88

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.870
Plasma Protein Binding: 89.57
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: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.260
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.280
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.200
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.730
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: -184.400
Rat (Acute): 3.850
Rat (Chronic Oral): 1.830
Fathead Minnow: 3.890
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 474.870
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 3.460
Log(P): 4.8
Log S: -5.21
Log(Vapor Pressure): -8.33
Melting Point: 161.18
pKa Acid: 10.64
pKa Basic: 6.52

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.8767
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.8767
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8290
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8290
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8135
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8135
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8122
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8122
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7725
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7725
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7537
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7537
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7487
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7487
Methyl-branched lipid omega-hydroxylase	P9WPP3	CP124_MYCTU	Mycobacterium tuberculosis	3	0.7465
Methyl-branched lipid omega-hydroxylase	P9WPP3	CP124_MYCTU	Mycobacterium tuberculosis	3	0.7465
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7424
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7424
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7384
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7384
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7337
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7337
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7303
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7303
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7127
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7127

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