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Crassoside A

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Diterpenoid

Canonical Smiles	CC(=O)O[C@H]1/C(=C/CC/C(=C/CC[C@@]([C@H](C[C@H]2[C@H]1OC(=O)C2=C)O)(C)O)/C)/C
InChI	InChI=1S/C22H32O6/c1-13-8-6-10-14(2)19(27-16(4)23)20-17(15(3)21(25)28-20)12-18(24)22(5,26)11-7-9-13/h9-10,17-20,24,26H,3,6-8,11-12H2,1-2,4-5H3/b13-9+,14-10+/t17-,18+,19+,20-,22-/m1/s1
InChIKey	LOBTUTHTMBAWQV-RCJCYISHSA-N
Formula	C₂₂H₃₂O₆
HBA	6
HBD	2
MW	392.49
Rotatable Bonds	1
TPSA	93.06
LogP	2.98
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.64
Exact Mass	392.22
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Crassocephalum mannii	Asteraceae	Plantae	189252

Showing of synonyms

Hegazy MEF, Aly AA, et al. (2008). A new 14,15-dinor-labdane glucoside from Crassocephalum mannii. Natural Product Communications,2008,3(6),869-872. [View]

Pubchem: 11995173

Zinc: ZINC000040872439

Nmrshiftdb2: 70044384

Chembl: CHEMBL462803

No compound-protein relationship available.

SMILES: C=C1C(=O)OC(C12)CC=CCCC=CCCCCC2

Level: 0

Mol. Weight: 392.49 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp): -4.52
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.67
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.67

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.63
Plasma Protein Binding: 55.84
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: 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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.4
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.47
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.49
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.43
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: -4.92
Rat (Acute): 2.84
Rat (Chronic Oral): 2.12
Fathead Minnow: 4.17
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 399.25
Hydration Free Energy: -7.62
Log(D) at pH=7.4: 2.32
Log(P): 3.03
Log S: -4.09
Log(Vapor Pressure): -7.49
Melting Point: 157.44
pKa Acid: 8.0
pKa Basic: 4.55

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8290
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8290
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8128
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8128
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8095
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8095
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7918
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7918
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7889
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7889
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7793
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7793
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7689
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7689
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7529
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7529
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7528
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7528
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7470
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7470
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7409
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7409
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7384
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7384
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7358
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7358
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7066
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7066
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7010
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7010

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