(+)-[1R*,4S*,10R*]-4-hydroxycembra-2E, 7E,11Z-trien-20,10-olide - Compound Card

(+)-[1R*,4S*,10R*]-4-hydroxycembra-2E, 7E,11Z-trien-20,10-olide

Select a section from the left sidebar

(+)-[1R*,4S*,10R*]-4-hydroxycembra-2E, 7E,11Z-trien-20,10-olide

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Cembranolide Diterpene
Canonical Smiles C/C/1=C\CC[C@](C)(O)/C=C/[C@H](CCC2=C[C@@H](C1)OC2=O)C(C)C
InChI InChI=1S/C20H30O3/c1-14(2)16-7-8-17-13-18(23-19(17)21)12-15(3)6-5-10-20(4,22)11-9-16/h6,9,11,13-14,16,18,22H,5,7-8,10,12H2,1-4H3/b11-9+,15-6+/t16-,18+,20-/m0/s1
InChIKey KLOZYZWTTNSEEN-IBKADNNNSA-N
Formula C20H30O3
HBA 3
HBD 1
MW 318.46
Rotatable Bonds 1
TPSA 46.53
LogP 4.33
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 318.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Croton gratissimus Euphorbiaceae Plantae 316784

Showing of synonyms

  • Mulholland DA, Langat MK, et al. (2010). Cembranolides from the stem bark of the southern African medicinal plant, Croton gratissimus (Euphorbiaceae). Phytochemistry, 2010, 71(11-12), 1381–1386. [View]
Pubchem: 46872827
Chebi: 68867
Nmrshiftdb2: 60056488
Metabolights: MTBLC68867

No compound-protein relationship available.

Structure

SMILES: O=C1OC(C=C12)CC=CCCCC=CCCC2

Level: 0

Mol. Weight: 318.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.39
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.72
Plasma Protein Binding
67.26
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
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
6.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.47
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.01
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.06
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
-2.53
Rat (Acute)
2.01
Rat (Chronic Oral)
1.76
Fathead Minnow
4.45
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
360.55
Hydration Free Energy
-5.02
Log(D) at pH=7.4
4.02
Log(P)
4.36
Log S
-4.92
Log(Vapor Pressure)
-5.31
Melting Point
108.31
pKa Acid
9.35
pKa Basic
6.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9534
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9312
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.9287
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8978
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8906
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8742
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8627
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.8143
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7965
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7919
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7859
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7854
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7800
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7785
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7767
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7732
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7713
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7647
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7615
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7569
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7551
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7541
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7508
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7497
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7431
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7427
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7417
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7411
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7402
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7391
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7363
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7338
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7310
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7292
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7290
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7280
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7273
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7272
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7240
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7222
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7199
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7195
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7188
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7185
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7176
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7168
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7157
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7154
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7145
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7139
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7118
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7109
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7075
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7065
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7027
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7022

Download SDF