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Isochamaejasmin A

Family: Plantae - Ochnaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Biflavanone

Canonical Smiles	Oc1ccc(cc1)[C@@H]1Oc2cc(O)cc(c2C(=O)[C@H]1[C@@H]1[C@H](Oc2c(C1=O)c(O)cc(c2)O)c1ccc(cc1)O)O
InChI	InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)29-25(27(37)23-19(35)9-17(33)11-21(23)39-29)26-28(38)24-20(36)10-18(34)12-22(24)40-30(26)14-3-7-16(32)8-4-14/h1-12,25-26,29-36H/t25-,26+,29+,30-
InChIKey	RNQBLQALVMHBKH-SQYWJIFTSA-N
Formula	C₃₀H₂₂O₁₀
HBA	10
HBD	6
MW	542.5
Rotatable Bonds	3
TPSA	173.98
LogP	4.49
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	542.12
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ochna holstii	Ochnaceae	Plantae	1389766

Showing of synonyms

Kalenga TM, Ndoile MM, et al. (2021). Biflavanones, Chalconoids, and Flavonoid Analogues from the Stem Bark of Ochna holstii. Journal of natural products,2021, 84(2), 364-372. [View] [PubMed]

Pubchem: 390361

Cas: 93859-63-3

Zinc: ZINC000004098324

Kegg Ligand: C09758

Chebi: 5994

Nmrshiftdb2: 60075141

Metabolights: MTBLC5994

Chembl: CHEMBL3318021

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 542.5 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 542.5 g/mol

SMILES: c1cccc(c12)OCC(C2=O)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 542.5 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 542.5 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 542.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 542.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.12
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.990
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 2.87

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.210
Plasma Protein Binding: 92.05
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.280
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.070
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.960
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.790
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -5349.460
Rat (Acute): 2.240
Rat (Chronic Oral): 3.700
Fathead Minnow: 18.950
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 552.770
Hydration Free Energy: -3.040
Log(D) at pH=7.4: 3.440
Log(P): 4.44
Log S: -6.33
Log(Vapor Pressure): -9.0
Melting Point: 340.08
pKa Acid: 9.81
pKa Basic: 5.74

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.9243
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9078
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9035
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8932
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8916
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8902
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8813
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8734
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8682
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8653
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8588
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8535
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8509
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8497
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8457
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.8456
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8439
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8409
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8401
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8289
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8260
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8253
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.8229
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8226
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8208
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8128
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8121
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8014
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7949
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7946
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7940
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7849
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7824
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7799
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7788
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7730
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7722
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7702
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7690
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7633
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7628
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7600
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7595
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7569
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7550
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7549
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7535
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7522
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7522
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7516
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7501
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7492
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7457
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7454
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7428
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7403
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7375
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7339
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7313
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7310
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7300
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	4	0.7286
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	5	0.7271
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7264
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7260
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7249
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7223
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7222
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.7201
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7197
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7140
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7137
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7132
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7129
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7119
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7105
Prostaglandin reductase 1	Q14914	PTGR1_HUMAN	Homo sapiens	5	0.7100
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7099
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7086
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7078
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7074
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7071
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7052
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7047
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7036
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7023

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