(1R*,2R*,3E,7R*,llR*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,8(17)-dien-2,7,16,18-tetrol - Compound Card

(1R*,2R*,3E,7R*,llR*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,8(17)-dien-2,7,16,18-tetrol

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(1R*,2R*,3E,7R*,llR*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,8(17)-dien-2,7,16,18-tetrol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles OC(=O)C[C@@](CCC(=O)OC/C/1=C/[C@H](O)[C@@]2(C)CC[C@H]([C@H]2CCC(=C)[C@H](CC1)O)C(O)(C)C)(O)C
InChI InChI=1S/C27H44O8/c1-17-6-8-20-19(25(2,3)33)10-13-27(20,5)22(29)14-18(7-9-21(17)28)16-35-24(32)11-12-26(4,34)15-23(30)31/h14,19-22,28-29,33-34H,1,6-13,15-16H2,2-5H3,(H,30,31)/b18-14+/t19-,20-,21+,22+,26-,27+/m1/s1
InChIKey FGUBTMXAPHNLQD-XEWQPSFPSA-N
Formula C27H44O8
HBA 7
HBD 5
MW 496.64
Rotatable Bonds 8
TPSA 144.52
LogP 3.12
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 496.3
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chrozophora obliqua Euphorbiaceae Plantae 316753

Showing of synonyms

  • Mohamed KM, Ohtani K, et al. (1995). 3-Hydroxy-3-methylglutaryl dolabellane diterpenes from Chrozophora obliqua. Phytochemistry,1995,39(1),151-161. [View]
Pubchem: 162817260
Nmrshiftdb2: 60051708

No compound-protein relationship available.

Structure

SMILES: C1C=CCCCC(=C)CCC(C12)CCC2

Level: 0

Mol. Weight: 496.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.08
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.08
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.8
Plasma Protein Binding
76.55
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.88
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
-101.85
Rat (Acute)
2.81
Rat (Chronic Oral)
2.34
Fathead Minnow
4.06
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
490.88
Hydration Free Energy
-2.49
Log(D) at pH=7.4
-0.12
Log(P)
1.68
Log S
-2.97
Log(Vapor Pressure)
-10.99
Melting Point
161.13
pKa Acid
3.6
pKa Basic
6.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9320
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9320
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9021
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9021
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8651
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8651
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8506
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8506
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8344
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8344
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8238
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8238
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8139
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8139
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8075
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8075
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8061
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8061
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7935
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7935
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7847
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7847
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7759
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7759
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7697
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7697
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7606
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7606
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7567
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7567
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7558
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7558
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7550
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7550
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7518
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7518
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7503
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7503
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7479
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7479
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7363
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7363
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7315
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7315
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7305
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7305
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7288
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7288
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7271
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7271
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7259
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7259
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7252
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7252
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7180
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7180
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7177
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7177
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7167
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7167
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7154
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7154
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7148
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7148
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7094
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7094
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7087
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7087
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7079
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7079
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7042
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7042
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7038
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7038
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7037
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7037
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7035
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7035
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7009
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7009

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