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2-epi-16-deoxysarcophine

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

Canonical Smiles	C/C/1=C\CC[C@]2(C)O[C@H]2CC/C(=C/[C@@H]2C(=C(C)CO2)CC1)/C
InChI	InChI=1S/C20H30O2/c1-14-6-5-11-20(4)19(22-20)10-8-15(2)12-18-17(9-7-14)16(3)13-21-18/h6,12,18-19H,5,7-11,13H2,1-4H3/b14-6+,15-12+/t18-,19+,20+/m1/s1
InChIKey	OQGXDKRHMBRZCS-FYMBVOBGSA-N
Formula	C₂₀H₃₀O₂
HBA	2
HBD	0
MW	302.46
Rotatable Bonds	0
TPSA	21.76
LogP	5.11
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.7
Exact Mass	302.22
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Sarcophyton glaucum	Alcyoniidae	Animalia	70919

Showing of synonyms

Sawant SS, Youssef DTA, et al. (2006). Biocatalytic and antimetastatic studies of the marine cembranoids sarcophine and 2-epi-16-deoxysarcophine. Journal of Natural Products,2006,69(7),1010-1013. [View] [PubMed]

Pubchem: 13245417

Zinc: ZINC000039433926

Nmrshiftdb2: 60070609

Chembl: CHEMBL496841

No compound-protein relationship available.

SMILES: C12C(O2)CCC=CCCC=3C(OCC3)C=CCC1

Level: 0

Mol. Weight: 302.46 g/mol

Antimetastatic

Absorption

Caco-2 (logPapp): -4.96
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.31
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.28

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.4
Plasma Protein Binding: 34.61
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: 15.57
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.06
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.33
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.9
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: 0.43
Rat (Acute): 1.66
Rat (Chronic Oral): 1.49
Fathead Minnow: 4.85
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 366.72
Hydration Free Energy: -3.03
Log(D) at pH=7.4: 3.87
Log(P): 5.38
Log S: -4.92
Log(Vapor Pressure): -3.75
Melting Point: 40.04
pKa Acid: 9.17
pKa Basic: 5.61

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9382
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9382
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9296
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9296
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8559
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8559
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.8544
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.8544
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8500
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8500
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8427
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8427
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.8042
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.8042
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8039
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8039
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8027
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8027
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8015
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8015
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7884
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7884
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7776
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7776
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7764
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7764
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7697
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7697
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7678
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7678
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7653
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7653
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7639
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7639
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7610
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7610
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7574
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7574
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7520
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7520
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7511
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7511
Retinoic acid receptor RXR	Q8T5C6	RXR_BIOGL	Biomphalaria glabrata	3	0.7509
Retinoic acid receptor RXR	Q8T5C6	RXR_BIOGL	Biomphalaria glabrata	3	0.7509
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7504
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7504
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7470
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7470
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7469
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7469
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7463
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7463
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7450
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7450
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7419
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7419
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7409
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7409
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7376
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7376
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7328
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7328
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7323
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7323
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7317
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7317
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7314
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7314
Putative cytochrome P450 120	Q59990	CP120_SYNY3	Synechocystis sp	3	0.7313
Putative cytochrome P450 120	Q59990	CP120_SYNY3	Synechocystis sp	3	0.7313
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7295
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7295
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7293
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7293
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7260
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7260
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7229
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7229
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7211
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7211
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7203
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7203
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7176
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7176
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7167
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7167
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7146
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7146
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7144
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7144
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7129
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7129
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7093
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7093
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7060
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7060
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7058
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7058
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7051
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7051
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7050
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7050
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7044
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7044
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7037
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7037
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7034
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7034
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7026
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7026
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7014
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7014
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7002
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7002

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