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Tessmannic acid

Family: Plantae - Caesalpiniaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Nor-Halimane Diterpenoid

Canonical Smiles	OC(=O)CC[C@@H]1C(=C(C)C)CC[C@H]([C@]1(C)CCc1cocc1)C
InChI	InChI=1S/C20H30O3/c1-14(2)17-6-5-15(3)20(4,18(17)7-8-19(21)22)11-9-16-10-12-23-13-16/h10,12-13,15,18H,5-9,11H2,1-4H3,(H,21,22)/t15-,18-,20+/m1/s1
InChIKey	OMCFKAYBHWTBQV-ZTNFWEORSA-N
Formula	C₂₀H₃₀O₃
HBA	2
HBD	1
MW	318.46
Rotatable Bonds	6
TPSA	50.44
LogP	5.47
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.65
Exact Mass	318.22
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tessmannia densiflora	Caesalpiniaceae	Plantae	1911674

Showing of synonyms

Kihampa C, Nkunya MH, et al. (2009). Anti-mosquito and antimicrobial nor-halimanoids, isocoumarins and an anilinoid from Tessmannia densiflora. Phytochemistry,2009,70(10),1233-1238. [View] [PubMed]

Pubchem: 44472192

Zinc: ZINC000014693582

Nmrshiftdb2: 70038069

No compound-protein relationship available.

SMILES: C=C1CC(CCC1)CCc2ccoc2

Level: 1

Mol. Weight: 318.46 g/mol

SMILES: C=C1CCCCC1

Level: 0

Mol. Weight: 318.46 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 318.46 g/mol

Antibacterial

Antifungal

Larvicidal

Absorption

Caco-2 (logPapp): -4.78
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.76
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.42

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.29
Plasma Protein Binding: 89.56
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: 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: 1.5
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.82
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.06
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.04
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: -0.88
Rat (Acute): 2.27
Rat (Chronic Oral): 1.94
Fathead Minnow: 3.95
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 359.14
Hydration Free Energy: -6.05
Log(D) at pH=7.4: 2.48
Log(P): 5.52
Log S: -4.65
Log(Vapor Pressure): -7.5
Melting Point: 105.85
pKa Acid: 6.07
pKa Basic: 7.2

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8151
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8151
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7942
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7942
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7906
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7906
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7877
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7877
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7749
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7749
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7729
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7729
Aspartate-semialdehyde dehydrogenase	Q51344	DHAS_PSEAE	Pseudomonas aeruginosa	3	0.7687
Aspartate-semialdehyde dehydrogenase	Q51344	DHAS_PSEAE	Pseudomonas aeruginosa	3	0.7687
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7600
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7600
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7525
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7525
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7374
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7374
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7354
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7354
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7318
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7318
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	2	0.7303
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	2	0.7303
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7270
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7270
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7267
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7267
2'-5'-oligoadenylate synthase 1	P00973	OAS1_HUMAN	Homo sapiens	2	0.7219
2'-5'-oligoadenylate synthase 1	P00973	OAS1_HUMAN	Homo sapiens	2	0.7219
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7219
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7219
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7215
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7215
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7168
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7168
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7126
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7126
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7105
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7105
C-C chemokine receptor type 5	P51681	CCR5_HUMAN	Homo sapiens	3	0.7093
C-C chemokine receptor type 5	P51681	CCR5_HUMAN	Homo sapiens	3	0.7093
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	2	0.7078
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	2	0.7078
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7071
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7071
Alpha-aminoadipic semialdehyde dehydrogenase	P49419	AL7A1_HUMAN	Homo sapiens	2	0.7051
Alpha-aminoadipic semialdehyde dehydrogenase	P49419	AL7A1_HUMAN	Homo sapiens	2	0.7051
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	2	0.7017
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	2	0.7017
Three-prime repair exonuclease 1	Q91XB0	TREX1_MOUSE	Mus musculus	2	0.7001
Three-prime repair exonuclease 1	Q91XB0	TREX1_MOUSE	Mus musculus	2	0.7001

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