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7beta-chloro-8alpha-hydroxy-12-acetoxy-deepoxysarcophine

Family: Animalia - Alcyoniidae
Kingdom: Animalia
Class: Terpenoid
- Subclass: Cembranoid Diterpene

Canonical Smiles	C/C/1=C\[C@H]2OC(=O)C(=C2CC[C@](/C=C/C[C@@](C(CC1)Cl)(C)O)(C)OC(=O)C)C
InChI	InChI=1S/C22H31ClO5/c1-14-7-8-19(23)22(5,26)11-6-10-21(4,28-16(3)24)12-9-17-15(2)20(25)27-18(17)13-14/h6,10,13,18-19,26H,7-9,11-12H2,1-5H3/b10-6+,14-13+/t18-,19?,21-,22-/m1/s1
InChIKey	KGDGALKCDPHUOO-MPHPMYICSA-N
Formula	C₂₂H₃₁ClO₅
HBA	5
HBD	1
MW	410.94
Rotatable Bonds	1
TPSA	72.83
LogP	4.38
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.64
Exact Mass	410.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Sarcophyton ehrenbergi	Alcyoniidae	Animalia	358800

Showing of synonyms

Elkhateeb A, El-Beih AA, et al. (2014). New terpenes from the Egyptian soft coral Sarcophyton ehrenbergi. Marine Drugs,2014,12,1977-1986. [View] [PubMed]

Pubchem: 162817607

Nmrshiftdb2: 70048045

No compound-protein relationship available.

SMILES: C1C(=O)OC(C=12)C=CCCCCCC=CCCC2

Level: 0

Mol. Weight: 410.94 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.71
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.76
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.64

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.57
Plasma Protein Binding: 57.86
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: 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: 7.69
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.1
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.16
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.18
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: Safe
T. Pyriformis: -7.28
Rat (Acute): 2.51
Rat (Chronic Oral): 1.61
Fathead Minnow: 4.59
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: 393.27
Hydration Free Energy: -4.84
Log(D) at pH=7.4: 3.37
Log(P): 3.85
Log S: -4.54
Log(Vapor Pressure): -6.4
Melting Point: 123.92
pKa Acid: 9.46
pKa Basic: 4.93

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9276
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9276
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8807
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8807
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8666
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8666
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8054
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8054
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7898
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7898
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7865
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7865
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7794
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7794
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7730
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7730
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7672
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7672
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7666
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7666
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7518
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7518
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7442
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7442
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7421
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7421
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7408
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7408
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7360
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7360
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7206
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7206
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7157
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7157
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7088
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7088
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7079
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7079
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7052
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7052

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