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Pachycladin C

Family: Animalia - Alcyoniidae
Kingdom: Animalia
Class: Terpenoid
- Subclass: Eunicellin-Type Diterpene

Canonical Smiles	CC(=O)O[C@H]1CC[C@@](C)(O)[C@@H]2O[C@H](CC1=C)[C@@H]1[C@H]2[C@H](CCC1=C)C(C)C
InChI	InChI=1S/C22H34O4/c1-12(2)16-8-7-13(3)19-18-11-14(4)17(25-15(5)23)9-10-22(6,24)21(26-18)20(16)19/h12,16-21,24H,3-4,7-11H2,1-2,5-6H3/t16-,17+,18-,19-,20-,21-,22-/m1/s1
InChIKey	CDRWIAOABOJFQY-CZIVXSDSSA-N
Formula	C₂₂H₃₄O₄
HBA	4
HBD	1
MW	362.51
Rotatable Bonds	2
TPSA	55.76
LogP	4.03
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.77
Exact Mass	362.25
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cladiella pachyclados	Alcyoniidae	Animalia	859391

Showing of synonyms

Hassan HM, Khanfar MA, et al. (2010). Pachycladins A-E, prostate cancer invasion and migration inhibitory eunicellin-based diterpenoids from the Red Sea soft coral Cladiella pachyclados. Journal of Natural Products,2010,73(5),848-853. [View] [PubMed]

Pubchem: 46833116

Zinc: ZINC000049110861

Chembl: CHEMBL1096781

No compound-protein relationship available.

SMILES: C=C1CCCC(C12)C3CCCCC(=C)CC2O3

Level: 0

Mol. Weight: 362.51 g/mol

Antimigratory

Absorption

Caco-2 (logPapp): -4.58
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.62
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.05

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.92
Plasma Protein Binding: 59.51
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.74
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.43
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.94
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.66
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: -2.02
Rat (Acute): 3.37
Rat (Chronic Oral): 1.24
Fathead Minnow: 3.92
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: 397.85
Hydration Free Energy: -3.51
Log(D) at pH=7.4: 3.32
Log(P): 5.18
Log S: -4.99
Log(Vapor Pressure): -6.97
Melting Point: 128.12
pKa Acid: 9.44
pKa Basic: 6.04

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9519
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9519
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8689
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8689
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8608
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8608
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8154
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8154
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8153
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8153
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7963
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7963
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7800
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7800
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7767
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7767
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7649
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7649
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7439
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7439
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7380
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7380
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7359
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7359
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7348
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7348
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7303
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7303
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7295
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7295
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7248
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7248
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7225
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7225
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7125
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7125
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7113
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7113
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7077
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7077
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7059
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7059
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7003
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7003

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