8alpha-hydroxy-13-epi-pimar-16-en-18-al - Compound Card

8alpha-hydroxy-13-epi-pimar-16-en-18-al

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8alpha-hydroxy-13-epi-pimar-16-en-18-al

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC(=O)[C@]1(C)CCC[C@]2(C1CC=C1[C@@H]2C[C@H]([C@](C1)(C)C=C)O)C
InChI InChI=1S/C21H32O3/c1-6-19(2)13-14-8-9-16-20(3,15(14)12-17(19)22)10-7-11-21(16,4)18(23)24-5/h6,8,15-17,22H,1,7,9-13H2,2-5H3/t15-,16?,17+,19+,20+,21+/m0/s1
InChIKey OLBJZJJCPIJGGV-FKFNPBDMSA-N
Formula C21H32O3
HBA 3
HBD 1
MW 332.48
Rotatable Bonds 2
TPSA 46.53
LogP 4.27
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 332.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tetraclinis articulata Cupressaceae Plantae 13717

Showing of synonyms

  • Barrero AF, Quılez del Moral JF, et al. (2003). Diterpenoids from Tetraclinis articulata that inhibit various human leukocyte functions. Journal of Natural Products,2003,66(6),844-850. [View] [PubMed]
Pubchem: 11034960

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C1=2)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 332.48 g/mol

Inhibit various human leukocyte functions

Absorption

Caco-2 (logPapp)
-4.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.400
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.980
Plasma Protein Binding
64.47
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
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.390
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.730
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.400
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.180
Micronucleos
Safe
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
-1.330
Rat (Acute)
2.140
Rat (Chronic Oral)
1.870
Fathead Minnow
3.920
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
381.660
Hydration Free Energy
-4.580
Log(D) at pH=7.4
4.420
Log(P)
5.26
Log S
-5.06
Log(Vapor Pressure)
-6.0
Melting Point
126.0
pKa Acid
10.87
pKa Basic
6.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9103
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9103
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8931
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8931
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8848
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8848
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8788
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8788
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8472
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8472
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8442
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8442
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8440
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8440
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8396
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8396
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8335
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8335
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8307
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8307
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8276
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8276
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8160
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8160
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8158
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8158
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8118
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8118
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8110
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8110
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8098
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8098
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8066
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8066
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8006
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8006
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7983
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7983
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7829
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7829
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7825
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7825
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7809
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7809
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7808
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7808
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7707
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7707
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7672
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7672
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7665
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7665
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7639
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7639
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7630
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7630
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7625
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7625
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7607
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7607
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7592
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7592
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7533
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7533
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7529
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7529
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7528
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7528
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7527
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7527
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7473
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7473
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7447
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7447
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7412
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7412
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7357
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7357
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7354
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7354
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7326
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7326
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7306
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7306
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7274
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7274
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7268
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7268
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7263
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7263
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7258
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7258
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7248
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7248
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7204
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7204
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7203
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7203
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7195
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7195
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7189
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7189
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7178
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7178
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7153
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7153
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7151
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7151
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7110
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7110
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7100
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7100
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7067
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7067
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7067
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7067
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7039
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7039
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 4 0.7034
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 4 0.7034
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7033
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7033
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7032
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7032
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7030
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7030
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7029
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7029
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7008
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7008

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