26-hydroxy-3-keto-24-methylenecycloartan-30-oic acid - Compound Card

26-hydroxy-3-keto-24-methylenecycloartan-30-oic acid

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26-hydroxy-3-keto-24-methylenecycloartan-30-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Rhizophoraceae
  • Kingdom: Plantae
  • Class: Cycloartanol
Canonical Smiles OCC(C(=C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CCC(=O)C2(C)C)C)C)C
InChI InChI=1S/C31H50O2/c1-20(22(3)18-32)8-9-21(2)23-12-14-29(7)25-11-10-24-27(4,5)26(33)13-15-30(24)19-31(25,30)17-16-28(23,29)6/h21-25,32H,1,8-19H2,2-7H3/t21-,22?,23-,24+,25+,28-,29+,30-,31+/m1/s1
InChIKey OKILVWSNJYSCMZ-IUNBOQICSA-N
Formula C31H50O2
HBA 2
HBD 1
MW 454.74
Rotatable Bonds 6
TPSA 37.3
LogP 7.6
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 454.38
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Cassipourea congoensis Rhizophoraceae Plantae 2708747

Showing of synonyms

  • Takou DM, Waffo AFK, et al. (2019). Melanin Production Inhibitors from the West African Cassipourea congoensis. Planta Medica International Open 2019; 6(02): e50-e56. [View]
Pubchem: 10623623
Nmrshiftdb2: 60060960

No compound-protein relationship available.

Structure

SMILES: C1CC(=O)CC(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 454.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.03
Plasma Protein Binding
91.05
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.93
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.21
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.23
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.52
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-142.59
Rat (Acute)
2.21
Rat (Chronic Oral)
1.87
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
464.45
Hydration Free Energy
-2.82
Log(D) at pH=7.4
6.66
Log(P)
7.28
Log S
-6.29
Log(Vapor Pressure)
-8.8
Melting Point
175.89
pKa Acid
11.69
pKa Basic
7.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9516
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9157
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9127
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8955
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8803
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8733
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8697
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8587
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8537
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8510
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8434
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8334
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8290
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8168
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8072
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8006
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8001
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7935
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7922
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7883
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7864
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7744
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7738
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7719
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7692
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7636
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7616
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7597
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7547
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7546
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7542
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7520
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7513
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7506
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7397
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7384
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7376
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7347
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7323
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7323
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7236
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7231
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7221
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7218
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7201
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7197
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7181
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7166
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7141
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7119
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7073
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7058
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7054
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7052
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7047
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7042
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7038
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7037
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7014

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