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Cedkathryn B

Family: Plantae - Ptaeroxylaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Pentanortriterpenoid

Canonical Smiles	O=C1C=C[C@@](O1)(C)[C@H]1C[C@@]2(OC1(C)C)O[C@H]1[C@@H](C2)[C@]23C[C@]3(CC1)[C@@H](OC2=O)c1cocc1
InChI	InChI=1S/C25H28O7/c1-21(2)17(22(3)7-5-18(26)31-22)11-24(32-21)10-15-16(30-24)4-8-23-13-25(15,23)20(27)29-19(23)14-6-9-28-12-14/h5-7,9,12,15-17,19H,4,8,10-11,13H2,1-3H3/t15-,16-,17+,19+,22+,23-,24-,25-/m1/s1
InChIKey	ZLKNSNBMQLJCPU-AROYWQBSSA-N
Formula	C₂₅H₂₈O₇
HBA	7
HBD	0
MW	440.49
Rotatable Bonds	2
TPSA	84.2
LogP	3.84
Number Rings	7
Number Aromatic Rings	1
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.68
Exact Mass	440.18
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cedrelopsis gracilis	Ptaeroxylaceae	Plantae	864331

Showing of synonyms

Mulholland DA, McFarland K, et al. (2004). Cedkathryns A and B, pentanortriterpenoids from Cedrelopsis gracilis (Ptaeroxylaceae). Phytochemistry, 2004, 65(21), 2929–2934. [View]

Pubchem: 11464841

Zinc: ZINC000095910047

Nmrshiftdb2: 70065422

No compound-protein relationship available.

SMILES: c1occc1C(OC2=O)C(C234)(C3)CCC5C4CC6(O5)CC(CO6)C(O7)C=CC7=O

Level: 2

Mol. Weight: 440.49 g/mol

SMILES: O=C1OCC(C123)(C2)CCC4C3CC5(O4)CC(CO5)C(O6)C=CC6=O

Level: 1

Mol. Weight: 440.49 g/mol

SMILES: c1occc1C(OC2=O)C(C234)(C3)CCC5C4CC6(O5)CCCO6

Level: 1

Mol. Weight: 440.49 g/mol

SMILES: O=C1OCC(C123)(C2)CCC4C3CC5(O4)CCCO5

Level: 0

Mol. Weight: 440.49 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 440.49 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 440.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.93
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.09
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.74

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.05
Plasma Protein Binding: 57.31
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.34
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.3
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.72
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.87
Micronucleos: Toxic
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: -148.42
Rat (Acute): 4.13
Rat (Chronic Oral): 1.71
Fathead Minnow: 3.97
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 484.71
Hydration Free Energy: -3.06
Log(D) at pH=7.4: 2.66
Log(P): 2.59
Log S: -5.72
Log(Vapor Pressure): -9.28
Melting Point: 250.98
pKa Acid: 6.99
pKa Basic: 6.17

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9046
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8673
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8375
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8137
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7956
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7845
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7801
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7709
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7672
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7646
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7634
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7595
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7562
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7509
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7506
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7490
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7466
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7423
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7357
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7357
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7356
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7343
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7327
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7298
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7292
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7278
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7235
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7231
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7231
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7227
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7187
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7186
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7183
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7174
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7157
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7114
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7092
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7071
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7068
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7055
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7039
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7021
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7016
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7011
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7010
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7007
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	2	0.7006
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7002

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