(1R*,2R*,3E,7E,11R*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-18-O-acetyldolabella-3,7-dien-2,16,18-triol - Compound Card

(1R*,2R*,3E,7E,11R*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-18-O-acetyldolabella-3,7-dien-2,16,18-triol

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(1R*,2R*,3E,7E,11R*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-18-O-acetyldolabella-3,7-dien-2,16,18-triol

Structure
Zoomed Structure
  • Family: Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles O=C(C[C@@](CC(=O)O)(O)C)OC/C/1=C\[C@H](O)[C@@]2(C)CC[C@H]([C@@H]2CC/C(=C/CC1)/C)C(OC(=O)C)(C)C
InChI InChI=1S/C28H44O8/c1-18-8-7-9-20(17-35-25(33)16-27(5,34)15-24(31)32)14-23(30)28(6)13-12-21(22(28)11-10-18)26(3,4)36-19(2)29/h8,14,21-23,30,34H,7,9-13,15-17H2,1-6H3,(H,31,32)/b18-8+,20-14-/t21-,22+,23+,27-,28+/m1/s1
InChIKey JQVPIVAXUXJKRP-NTLAMMLDSA-N
Formula C28H44O8
HBA 7
HBD 3
MW 508.65
Rotatable Bonds 8
TPSA 130.36
LogP 4.33
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 508.3
Number of Lipinski Rule Violations 1
# 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: 162897415

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC=CCCC=CC2

Level: 0

Mol. Weight: 190.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.8
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.100
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
85.01
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.260
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.970
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.370
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.600
Micronucleos
Toxic
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
-147.130
Rat (Acute)
2.290
Rat (Chronic Oral)
2.530
Fathead Minnow
4.080
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
490.550
Hydration Free Energy
-2.570
Log(D) at pH=7.4
1.390
Log(P)
4.15
Log S
-3.83
Log(Vapor Pressure)
-10.11
Melting Point
151.62
pKa Acid
4.66
pKa Basic
6.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9428
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9428
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8829
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8829
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8452
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8452
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8392
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8392
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8325
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8325
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8257
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8257
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8176
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8176
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 4 0.8159
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 4 0.8159
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8002
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8002
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7930
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7930
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7876
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7876
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7844
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7844
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7793
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7793
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7761
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7761
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7739
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7739
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7576
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7576
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7538
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7538
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7512
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7512
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7506
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7506
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7494
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7494
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7493
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7493
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7451
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7451
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7384
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7384
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7383
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7383
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7331
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7331
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7258
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7258
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7248
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7248
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 4 0.7237
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 4 0.7237
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7176
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7176
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7121
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7121
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7114
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7114
3-hydroxy-3-methylglutaryl-coenzyme A reductase P13702 MVAA_PSEMV Pseudomonas mevalonii 3 0.7092
3-hydroxy-3-methylglutaryl-coenzyme A reductase P13702 MVAA_PSEMV Pseudomonas mevalonii 3 0.7092
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7092
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7092
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7070
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7070
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7065
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7065
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7053
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7053
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7008
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7008

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