Natural Product: ENC002260

NPs Basic Information

Download MOL File
Name
Verruculogen
Molecular Formula C27H33N3O7
IUPAC Name*
(9R,14S,17S,23R,24S)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-enyl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.02,7.08,25.015,23.017,21]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione
SMILES
CC(=C[C@@H]1N2C3=C(C=CC(=C3)OC)C4=C2[C@H](CC(OO1)(C)C)N5C(=O)[C@@H]6CCCN6C(=O)[C@@]5([C@H]4O)O)C
InChI
InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20+,23-,27+/m0/s1
InChIKey
LRXYHMMJJCTUMY-GWXUGYLUSA-N
Synonyms
verruculogen; 12771-72-1; TR 1 toxin; TR 1; CHEBI:72765; (5R,10S,10aR,14aS,15bS)-10,10a-dihydroxy-6-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,14,14a,15b-hexahydro-12H-3,4-dioxa-5a,11a,15a-triazacycloocta[1,2,3-lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione; (9R,14S,17S,23R,24S)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-enyl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.02,7.08,25.015,23.017,21]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione; 4-Methyl-4-(2-(4-nitro-N-phenylbenzamido)ethyl)morpholin-4-ium bromide; Verrculogen; Verruculogen, powder; CHEMBL551369; DTXSID30894030; TR1; MFCD00079645; ZINC85564414; AKOS030213151; 5H,12H-3,4-Dioxa-5a,11a,15a-triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione,1,10,10a,14,14a,15b-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-, (5R,10S,10aR,14aS,15bS)-; C20045; J-005532; (5R,10S,10aR,14aS,15bS)-10,10a-Dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,12,13,14,14a,15b-octahydro-3,4-dioxa-5a,11a,15a-triazacycloocta[lm]indeno[5,6-b]fluorene-11,15(2H,5H)-dione; (5R-(5alpha,10 alpha,10aalpha,14aalpha,15balpha))-1,10,10a,14,14a,15b-Hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-5H,12H-3,4-dioxa-5a,11a,15a-triaza cyclooct (1m) indeno (5,6-b)fluorene-11,15(2H,13H)-dione; 10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)- 1,10,10a,14,14a,15b-hexahydro-5H,12H-3,4-dioxa-5a,11a,15a- triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione; 5H,12H-3,4-Dioxa-5a,11a,15a-triazacyclooct(lm)indeno(5,6-b)fluorene-11,15(2H,13H)-dione, 1,10,10a,14,14a,15b-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-, (5R,10S,10aR,14aS,15bS)-; 5H,12H-3,4-Dioxa-5a,11a,15a-triazacyclooct(lm)indeno(5,6-b)fluorene-11,15(2H,13H)-dione, 1,10,10a,14,14a,15b-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-,(5R-(5-alpha,10-alpha,10a-alpha,14a-alpha-15b-alpha))-; 8H5
CAS 12771-72-1
PubChem CID 13887805
ChEMBL ID CHEMBL551369
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Organoheterocyclic compou
      • Class: Indoles and derivatives
        • Subclass: Pyridoindoles
          • Direct Parent: Beta carbolines

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

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NPs Physi-Chem Properties

Molecular Weight: 511.6 ALogp: 1.8
HBD: 2 HBA: 7
Rotatable Bonds: 2 Lipinski's rule of five: Rejected
Polar Surface Area: 114.0 Aromatic Rings: 6
Heavy Atoms: 37 QED Weighted: 0.467

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.874 MDCK Permeability: 0.00001460
Pgp-inhibitor: 0.995 Pgp-substrate: 0.534
Human Intestinal Absorption (HIA): 0.063 20% Bioavailability (F20%): 0.47
30% Bioavailability (F30%): 0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.255 Plasma Protein Binding (PPB): 83.16%
Volume Distribution (VD): 1.43 Fu: 9.42%

ADMET: Metabolism

CYP1A2-inhibitor: 0.016 CYP1A2-substrate: 0.117
CYP2C19-inhibitor: 0.548 CYP2C19-substrate: 0.912
CYP2C9-inhibitor: 0.689 CYP2C9-substrate: 0.796
CYP2D6-inhibitor: 0.012 CYP2D6-substrate: 0.15
CYP3A4-inhibitor: 0.472 CYP3A4-substrate: 0.936

ADMET: Excretion

Clearance (CL): 8.571 Half-life (T1/2): 0.271

ADMET: Toxicity

hERG Blockers: 0.02 Human Hepatotoxicity (H-HT): 0.989
Drug-inuced Liver Injury (DILI): 0.989 AMES Toxicity: 0.039
Rat Oral Acute Toxicity: 0.082 Maximum Recommended Daily Dose: 0.997
Skin Sensitization: 0.192 Carcinogencity: 0.459
Eye Corrosion: 0.003 Eye Irritation: 0.005
Respiratory Toxicity: 0.802
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

*Note: the compound similarity was calculated by RDKIT.