1alpha,3beta-dihydroxytotarol - Compound Card

1alpha,3beta-dihydroxytotarol

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1alpha,3beta-dihydroxytotarol

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC(=O)[C@]1(C)CCC[C@]2(C1CCC1=C[C@@]([C@@H](C[C@H]21)O)(C)C=C)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/h6,13,15-17,22H,1,7-12H2,2-5H3/t15-,16?,17+,19+,20+,21+/m0/s1
InChIKey BSMXGJOGRNXRNP-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
2 Tetraclinis articulata Cupressaceae Plantae 13717

Showing of synonyms

  • Barrero A.F, Quílez del Moral J.F, et al. (2003). Diterpenoids from Tetraclinis articulata that Inhibit Various Human Leukocyte Functions. Journal of natural products, 2003, 66(6), 844-50. [View] [PubMed]
  • 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: 162994129

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C=12)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 332.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.57
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.390
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.980
Plasma Protein Binding
63.51
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
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
10.870
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.960
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.620
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.090
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
-1.470
Rat (Acute)
2.410
Rat (Chronic Oral)
1.920
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
382.720
Hydration Free Energy
-4.390
Log(D) at pH=7.4
4.230
Log(P)
4.91
Log S
-5.12
Log(Vapor Pressure)
-6.05
Melting Point
123.41
pKa Acid
10.77
pKa Basic
6.13
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 0.9121
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9121
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8944
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8944
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8875
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8875
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8450
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8450
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8373
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8373
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8314
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8314
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8159
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8159
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8080
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8080
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8039
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8039
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7910
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7910
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7823
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7823
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7801
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7801
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7768
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7768
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7707
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7707
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7704
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7704
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7679
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7679
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7618
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7618
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7553
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7553
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7533
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7533
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7520
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7520
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7477
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7477
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7402
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7402
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7401
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7401
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7381
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7381
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7364
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7364
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7356
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7356
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7355
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7355
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7354
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7354
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7344
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7344
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7330
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7330
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7290
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7290
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7261
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7261
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 4 0.7258
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 4 0.7258
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7209
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7209
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7184
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7184
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7164
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7164
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7131
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7131
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7115
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7115
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7104
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7104
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7100
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7100
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7089
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7089
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7068
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7068
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7064
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7064
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7029
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7029
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7028
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7028
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7027
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7027
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7005
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7005

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