NPs Basic Information

Name
Paxilline
Molecular Formula C27H33NO4
IUPAC Name*
(1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one
SMILES
C[C@]12CC[C@H]3C(=CC(=O)[C@H](O3)C(C)(C)O)[C@@]1(CC[C@@H]4[C@@]2(C5=C(C4)C6=CC=CC=C6N5)C)O
InChI
InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1
InChIKey
ACNHBCIZLNNLRS-UBGQALKQSA-N
Synonyms
paxilline; 57186-25-1; NSC 658707; BRN 5317894; MLS000028812; C27H33NO4; CHEBI:34907; 3T9U9Z96L7; (1s,2r,5s,7r,11s,14s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one; 1233509-81-3; SMR000058863; paxillin; 2H-Pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)-rel-; PAXILINE; UNII-3T9U9Z96L7; NSC-658707; (+)-paxilline; 2H-Pyrano(2'',3'':5',6')benz(1',2':6,7)indeno(1,2-b)indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)-; MFCD00083464; Spectrum5_001975; CBiol_001842; BSPBio_001427; KBioGR_000147; KBioSS_000147; SCHEMBL361232; CHEMBL410063; cid_105008; BDBM50854; KBio2_000147; KBio2_002715; KBio2_005283; KBio3_000293; KBio3_000294; DTXSID10972643; Bio1_000128; Bio1_000617; Bio1_001106; Bio2_000147; Bio2_000627; HMS1361H09; HMS1791H09; HMS1989H09; HMS2232J18; HMS3268F05; HMS3402H09; HY-N6778; ZINC3996035; HB1056; KC-155; AKOS024456907; Paxilline, powder, >=98% (HPLC); IDI1_033897; NCGC00025342-05; NCGC00025342-07; 2H-1-Benzopyrano(5',6':6,7)indeno(1,2-b)indol-3(4bh)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2-alpha,4b-beta,6a-alpha,12b-beta,12c-alpha,14a-beta)-; CS-0026740; SR-01000597527; SR-01000597527-1; BRD-K38251852-001-02-5; BRD-K38251852-001-06-6; Q10860377; EDD20523-48C0-4594-B22A-1FE297F60611; (2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-[1]benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one; (2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one; (2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a, 7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-h ydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2 '',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one; (2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a,7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one; NCGC00025342-07_C27H33NO4_(2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxy-2-propanyl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one
CAS 57186-25-1
PubChem CID 105008
ChEMBL ID CHEMBL410063
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Organoheterocyclic compou
      • Class: Naphthopyrans
        • Subclass: No Rank at Level Subclass
          • Direct Parent: Naphthopyrans

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

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

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 435.6 ALogp: 3.5
HBD: 3 HBA: 4
Rotatable Bonds: 1 Lipinski's rule of five: Accepted
Polar Surface Area: 82.6 Aromatic Rings: 6
Heavy Atoms: 32 QED Weighted: 0.612

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.882 MDCK Permeability: 0.00002600
Pgp-inhibitor: 0.232 Pgp-substrate: 0.934
Human Intestinal Absorption (HIA): 0.008 20% Bioavailability (F20%): 0.003
30% Bioavailability (F30%): 0.288

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.954 Plasma Protein Binding (PPB): 78.78%
Volume Distribution (VD): 1.1 Fu: 9.12%

ADMET: Metabolism

CYP1A2-inhibitor: 0.153 CYP1A2-substrate: 0.883
CYP2C19-inhibitor: 0.486 CYP2C19-substrate: 0.807
CYP2C9-inhibitor: 0.544 CYP2C9-substrate: 0.248
CYP2D6-inhibitor: 0.069 CYP2D6-substrate: 0.108
CYP3A4-inhibitor: 0.901 CYP3A4-substrate: 0.92

ADMET: Excretion

Clearance (CL): 7.922 Half-life (T1/2): 0.426

ADMET: Toxicity

hERG Blockers: 0.038 Human Hepatotoxicity (H-HT): 0.29
Drug-inuced Liver Injury (DILI): 0.398 AMES Toxicity: 0.508
Rat Oral Acute Toxicity: 0.96 Maximum Recommended Daily Dose: 0.937
Skin Sensitization: 0.81 Carcinogencity: 0.897
Eye Corrosion: 0.005 Eye Irritation: 0.013
Respiratory Toxicity: 0.988
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC001492 0.824 D0H4JM 0.281
ENC005990 0.712 D0U7GP 0.281
ENC002279 0.709 D01JGV 0.281
ENC005988 0.661 D05MQK 0.263
ENC001966 0.588 D0V4WD 0.254
ENC005989 0.571 D0K0KH 0.250
ENC003172 0.571 D04RLY 0.246
ENC002951 0.568 D04GJN 0.246
ENC000857 0.530 D06AEO 0.240
ENC004710 0.521 D0OT9S 0.240
*Note: the compound similarity was calculated by RDKIT.