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Andirobin

Family: Plantae - Meliaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Limonoid

Canonical Smiles	COC(=O)C[C@@H]1[C@](C)(C=CC(=O)C1(C)C)[C@@H]1CC[C@@]2([C@]3(C1=C)O[C@@H]3C(=O)O[C@H]2c1cocc1)C
InChI	InChI=1S/C27H32O7/c1-15-17(25(4)10-8-19(28)24(2,3)18(25)13-20(29)31-6)7-11-26(5)21(16-9-12-32-14-16)33-23(30)22-27(15,26)34-22/h8-10,12,14,17-18,21-22H,1,7,11,13H2,2-6H3/t17-,18+,21+,22-,25-,26+,27-/m1/s1
InChIKey	BFUCTROUWLSVBH-NMFQCOFDSA-N
Formula	C₂₇H₃₂O₇
HBA	7
HBD	0
MW	468.55
Rotatable Bonds	4
TPSA	95.34
LogP	4.34
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.59
Exact Mass	468.21
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pseudocedrela kotschyi	Meliaceae	Plantae	356281

Showing of synonyms

Sidjui LS, Nganso YOD, et al. (2018). Kostchyienones A and B, new antiplasmodial and cytotoxicity of limonoids from the roots of Pseudocedrela kotschyi (Schweinf.) Harms.. Zeitschrift fur Naturforschung. C, Journal of biosciences,2018, 73(3-4), 153-160. [View] [PubMed]

Pubchem: 12306782

Cas: 6488-63-7

Nmrshiftdb2: 60052015

Chembl: CHEMBL2373853

No compound-protein relationship available.

SMILES: O=C1C=CC(CC1)C(C2=C)CCC3C(OC(=O)C(C234)O4)c5ccoc5

Level: 2

Mol. Weight: 468.55 g/mol

SMILES: O=C1C=CC(CC1)C(C2=C)CCC3COC(=O)C(C234)O4

Level: 1

Mol. Weight: 468.55 g/mol

SMILES: C=C1CCCC2C(OC(=O)C(C123)O3)c4ccoc4

Level: 1

Mol. Weight: 468.55 g/mol

SMILES: C=C1CCCC2COC(=O)C(C123)O3

Level: 0

Mol. Weight: 468.55 g/mol

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 468.55 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 468.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.19
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.880
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.52

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.820
Plasma Protein Binding: 53.15
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: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 14.050
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.230
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.330
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 7.330
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: -235.470
Rat (Acute): 4.320
Rat (Chronic Oral): 2.120
Fathead Minnow: 4.270
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 468.310
Hydration Free Energy: -3.030
Log(D) at pH=7.4: 3.590
Log(P): 3.24
Log S: -5.58
Log(Vapor Pressure): -8.85
Melting Point: 194.88
pKa Acid: 4.98
pKa Basic: 3.93

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8053
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7852
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7849
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7744
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7689
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7665
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7664
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7601
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7600
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7540
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7531
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7530
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7498
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7470
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7415
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7376
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7374
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7348
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7306
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7303
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7297
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7293
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7288
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7283
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7282
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7274
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7274
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7270
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7251
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7250
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7225
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7221
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7196
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7184
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	2	0.7182
Probable esterase KAI2	Q9SZU7	KAI2_ARATH	Arabidopsis thaliana	3	0.7157
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7109
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7100
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7069
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7047
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7032
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7013
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	3	0.7009

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