Structure

Physi-Chem Properties

Molecular Weight:  273.14
Volume:  277.888
LogP:  1.346
LogD:  1.509
LogS:  -2.358
# Rotatable Bonds:  1
TPSA:  38.77
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.537
Synthetic Accessibility Score:  5.233
Fsp3:  0.562
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.987
MDCK Permeability:  2.887738992285449e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.041
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.051
30% Bioavailability (F30%):  0.067

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.959
Plasma Protein Binding (PPB):  49.883506774902344%
Volume Distribution (VD):  1.772
Pgp-substrate:  56.41618347167969%

ADMET: Metabolism

CYP1A2-inhibitor:  0.014
CYP1A2-substrate:  0.122
CYP2C19-inhibitor:  0.049
CYP2C19-substrate:  0.809
CYP2C9-inhibitor:  0.189
CYP2C9-substrate:  0.16
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.148
CYP3A4-inhibitor:  0.497
CYP3A4-substrate:  0.928

ADMET: Excretion

Clearance (CL):  14.242
Half-life (T1/2):  0.609

ADMET: Toxicity

hERG Blockers:  0.051
Human Hepatotoxicity (H-HT):  0.403
Drug-inuced Liver Injury (DILI):  0.423
AMES Toxicity:  0.964
Rat Oral Acute Toxicity:  0.177
Maximum Recommended Daily Dose:  0.944
Skin Sensitization:  0.806
Carcinogencity:  0.81
Eye Corrosion:  0.005
Eye Irritation:  0.018
Respiratory Toxicity:  0.902

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC241426

Natural Product ID:  NPC241426
Common Name*:   PXWINCSLFXUWBZ-BBRMVZONSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  PXWINCSLFXUWBZ-BBRMVZONSA-N
Standard InCHI:  InChI=1S/C16H19NO3/c1-19-13-3-2-12-5-7-17-6-4-11-10-20-15(18)8-14(11)16(12,17)9-13/h2-3,5,13H,4,6-10H2,1H3/t13-,16-/m0/s1
SMILES:  CO[C@H]1C=CC2=CCN3[C@]2(C1)C1=C(CC3)COC(=O)C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3318888
PubChem CID:   10074
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO3286 Erythrina americana Species Fabaceae Eukaryota Flowers Tantempango, Hidalgo, Mexico 2019-May DOI[10.1007/s11130-020-00822-2]
NPO7457 Erythrina berteroana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3286 Erythrina americana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3286 Erythrina americana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7457 Erythrina berteroana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3286 Erythrina americana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3286 Erythrina americana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3174 Sulfolobus shibatae Species Sulfolobaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO24842 Bulla gouldiana Species Bullidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7457 Erythrina berteroana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 1100.0 nM PMID[523950]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC241426 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.7071 Intermediate Similarity NPC296589
0.7064 Intermediate Similarity NPC133420
0.6909 Remote Similarity NPC75523
0.6822 Remote Similarity NPC476344
0.6818 Remote Similarity NPC199831
0.6818 Remote Similarity NPC474828
0.6818 Remote Similarity NPC68001
0.6818 Remote Similarity NPC474827
0.6792 Remote Similarity NPC150041
0.6759 Remote Similarity NPC270813
0.6727 Remote Similarity NPC473289
0.6667 Remote Similarity NPC469860
0.6667 Remote Similarity NPC469861
0.6667 Remote Similarity NPC130436
0.6667 Remote Similarity NPC72183
0.6667 Remote Similarity NPC110875
0.6667 Remote Similarity NPC118844
0.6667 Remote Similarity NPC299808
0.6633 Remote Similarity NPC471768
0.6609 Remote Similarity NPC63511
0.6579 Remote Similarity NPC474099
0.6574 Remote Similarity NPC476449
0.6571 Remote Similarity NPC469372
0.6552 Remote Similarity NPC58281
0.6514 Remote Similarity NPC52820
0.6491 Remote Similarity NPC271562
0.6421 Remote Similarity NPC163003
0.6415 Remote Similarity NPC212679
0.6415 Remote Similarity NPC220454
0.6415 Remote Similarity NPC469595
0.6392 Remote Similarity NPC228978
0.6372 Remote Similarity NPC6271
0.6355 Remote Similarity NPC32944
0.6355 Remote Similarity NPC193396
0.6339 Remote Similarity NPC77703
0.6337 Remote Similarity NPC42470
0.6327 Remote Similarity NPC123360
0.6321 Remote Similarity NPC81195
0.6321 Remote Similarity NPC95364
0.6321 Remote Similarity NPC142159
0.6316 Remote Similarity NPC64168
0.6289 Remote Similarity NPC470994
0.6289 Remote Similarity NPC476355
0.6289 Remote Similarity NPC140287
0.6283 Remote Similarity NPC474244
0.6277 Remote Similarity NPC218477
0.6263 Remote Similarity NPC41780
0.6263 Remote Similarity NPC187568
0.6262 Remote Similarity NPC159568
0.6228 Remote Similarity NPC80439
0.6228 Remote Similarity NPC279833
0.6228 Remote Similarity NPC173690
0.6216 Remote Similarity NPC4834
0.6214 Remote Similarity NPC193198
0.621 Remote Similarity NPC23963
0.6204 Remote Similarity NPC166110
0.62 Remote Similarity NPC471220
0.62 Remote Similarity NPC267231
0.6195 Remote Similarity NPC474348
0.619 Remote Similarity NPC26285
0.619 Remote Similarity NPC321197
0.6186 Remote Similarity NPC58956
0.6186 Remote Similarity NPC295633
0.6186 Remote Similarity NPC269206
0.6176 Remote Similarity NPC325031
0.6174 Remote Similarity NPC44514
0.6167 Remote Similarity NPC130124
0.6167 Remote Similarity NPC193471
0.6147 Remote Similarity NPC248193
0.6142 Remote Similarity NPC329401
0.6142 Remote Similarity NPC477987
0.6139 Remote Similarity NPC471299
0.6139 Remote Similarity NPC158565
0.6139 Remote Similarity NPC472965
0.6139 Remote Similarity NPC63649
0.6139 Remote Similarity NPC178277
0.6139 Remote Similarity NPC264227
0.6134 Remote Similarity NPC316984
0.6134 Remote Similarity NPC47857
0.6134 Remote Similarity NPC181510
0.6134 Remote Similarity NPC168758
0.6134 Remote Similarity NPC21713
0.6134 Remote Similarity NPC475608
0.6134 Remote Similarity NPC44733
0.6134 Remote Similarity NPC30911
0.6129 Remote Similarity NPC477140
0.6129 Remote Similarity NPC230849
0.6129 Remote Similarity NPC182794
0.6129 Remote Similarity NPC477143
0.6126 Remote Similarity NPC112654
0.6121 Remote Similarity NPC93179
0.6121 Remote Similarity NPC86906
0.6117 Remote Similarity NPC268122
0.6117 Remote Similarity NPC474252
0.6102 Remote Similarity NPC24389
0.6102 Remote Similarity NPC21324
0.61 Remote Similarity NPC171204
0.61 Remote Similarity NPC116177
0.61 Remote Similarity NPC7563
0.61 Remote Similarity NPC320630
0.61 Remote Similarity NPC141789
0.61 Remote Similarity NPC97516
0.61 Remote Similarity NPC57744
0.61 Remote Similarity NPC476028
0.6098 Remote Similarity NPC174463
0.6095 Remote Similarity NPC474369
0.6095 Remote Similarity NPC281172
0.6091 Remote Similarity NPC477129
0.6091 Remote Similarity NPC477130
0.6082 Remote Similarity NPC129665
0.6075 Remote Similarity NPC472302
0.6075 Remote Similarity NPC471057
0.6075 Remote Similarity NPC471058
0.6075 Remote Similarity NPC477128
0.6075 Remote Similarity NPC24816
0.6061 Remote Similarity NPC329826
0.6061 Remote Similarity NPC469414
0.6058 Remote Similarity NPC118423
0.6053 Remote Similarity NPC244456
0.6053 Remote Similarity NPC175531
0.6053 Remote Similarity NPC469657
0.605 Remote Similarity NPC469603
0.6042 Remote Similarity NPC199557
0.604 Remote Similarity NPC93763
0.604 Remote Similarity NPC299235
0.604 Remote Similarity NPC474341
0.604 Remote Similarity NPC108816
0.604 Remote Similarity NPC128276
0.6038 Remote Similarity NPC116575
0.6036 Remote Similarity NPC295347
0.602 Remote Similarity NPC474705
0.602 Remote Similarity NPC135703
0.6019 Remote Similarity NPC471325
0.6019 Remote Similarity NPC284561
0.6015 Remote Similarity NPC473703
0.6015 Remote Similarity NPC239252
0.6 Remote Similarity NPC27205
0.6 Remote Similarity NPC235369
0.6 Remote Similarity NPC14575
0.6 Remote Similarity NPC30486
0.6 Remote Similarity NPC97861
0.6 Remote Similarity NPC196487
0.6 Remote Similarity NPC235906
0.5983 Remote Similarity NPC195841
0.5983 Remote Similarity NPC233256
0.5981 Remote Similarity NPC312561
0.598 Remote Similarity NPC475210
0.598 Remote Similarity NPC270126
0.598 Remote Similarity NPC150646
0.5979 Remote Similarity NPC475310
0.5968 Remote Similarity NPC201889
0.5968 Remote Similarity NPC106791
0.5968 Remote Similarity NPC156336
0.5968 Remote Similarity NPC284656
0.5968 Remote Similarity NPC200412
0.5968 Remote Similarity NPC120599
0.5962 Remote Similarity NPC178676
0.5962 Remote Similarity NPC35556
0.5962 Remote Similarity NPC173609
0.5962 Remote Similarity NPC475690
0.5962 Remote Similarity NPC94200
0.5957 Remote Similarity NPC133904
0.5954 Remote Similarity NPC477988
0.5948 Remote Similarity NPC469895
0.5946 Remote Similarity NPC38830
0.5943 Remote Similarity NPC471060
0.5943 Remote Similarity NPC215364
0.5943 Remote Similarity NPC76283
0.5943 Remote Similarity NPC189311
0.5941 Remote Similarity NPC65603
0.5941 Remote Similarity NPC476794
0.5941 Remote Similarity NPC470240
0.5941 Remote Similarity NPC474760
0.5941 Remote Similarity NPC473825
0.5929 Remote Similarity NPC202705
0.5929 Remote Similarity NPC150967
0.5929 Remote Similarity NPC208094
0.5926 Remote Similarity NPC226863
0.5926 Remote Similarity NPC472220
0.5926 Remote Similarity NPC473151
0.5926 Remote Similarity NPC97884
0.5923 Remote Similarity NPC478136
0.5922 Remote Similarity NPC268827
0.5922 Remote Similarity NPC195424
0.5922 Remote Similarity NPC281132
0.5918 Remote Similarity NPC84038
0.5918 Remote Similarity NPC186531
0.5917 Remote Similarity NPC113012
0.5917 Remote Similarity NPC122926
0.5917 Remote Similarity NPC196073
0.5917 Remote Similarity NPC195435
0.5917 Remote Similarity NPC158854
0.5913 Remote Similarity NPC313234
0.5913 Remote Similarity NPC469851
0.5909 Remote Similarity NPC261730
0.5909 Remote Similarity NPC49420
0.5909 Remote Similarity NPC161644
0.5905 Remote Similarity NPC250315
0.5905 Remote Similarity NPC16488
0.59 Remote Similarity NPC138408

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC241426 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.6729 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6392 Remote Similarity NPD8039 Approved
0.6134 Remote Similarity NPD2204 Approved
0.6047 Remote Similarity NPD5667 Approved
0.6033 Remote Similarity NPD2607 Approved
0.5968 Remote Similarity NPD4574 Approved
0.5968 Remote Similarity NPD4576 Approved
0.5954 Remote Similarity NPD8392 Approved
0.5954 Remote Similarity NPD8391 Approved
0.5954 Remote Similarity NPD8390 Approved
0.5948 Remote Similarity NPD2258 Approved
0.5948 Remote Similarity NPD2259 Approved
0.5917 Remote Similarity NPD6420 Discontinued
0.5917 Remote Similarity NPD1752 Approved
0.5917 Remote Similarity NPD1756 Approved
0.5909 Remote Similarity NPD7260 Phase 2
0.5902 Remote Similarity NPD1376 Discontinued
0.5895 Remote Similarity NPD616 Clinical (unspecified phase)
0.5891 Remote Similarity NPD8451 Approved
0.5891 Remote Similarity NPD8273 Phase 1
0.5878 Remote Similarity NPD2627 Approved
0.5878 Remote Similarity NPD2628 Approved
0.5878 Remote Similarity NPD2626 Approved
0.5878 Remote Similarity NPD2160 Approved
0.5878 Remote Similarity NPD2159 Approved
0.5878 Remote Similarity NPD2625 Approved
0.5846 Remote Similarity NPD8448 Approved
0.5827 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5814 Remote Similarity NPD2608 Approved
0.5814 Remote Similarity NPD2609 Approved
0.5814 Remote Similarity NPD4216 Approved
0.5814 Remote Similarity NPD2611 Approved
0.5814 Remote Similarity NPD4215 Approved
0.5814 Remote Similarity NPD4217 Approved
0.5814 Remote Similarity NPD4218 Approved
0.5814 Remote Similarity NPD2612 Approved
0.5814 Remote Similarity NPD2610 Approved
0.5814 Remote Similarity NPD3131 Approved
0.5814 Remote Similarity NPD3132 Approved
0.581 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5802 Remote Similarity NPD2199 Approved
0.5802 Remote Similarity NPD2198 Approved
0.5794 Remote Similarity NPD1694 Approved
0.5781 Remote Similarity NPD7623 Phase 3
0.5781 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5738 Remote Similarity NPD2201 Approved
0.5727 Remote Similarity NPD6101 Approved
0.5727 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5714 Remote Similarity NPD2696 Approved
0.5714 Remote Similarity NPD5779 Approved
0.5714 Remote Similarity NPD2697 Approved
0.5714 Remote Similarity NPD5778 Approved
0.5714 Remote Similarity NPD2694 Approved
0.5714 Remote Similarity NPD2695 Approved
0.5714 Remote Similarity NPD7333 Discontinued
0.5714 Remote Similarity NPD7641 Discontinued
0.5702 Remote Similarity NPD4228 Discovery
0.5692 Remote Similarity NPD8341 Approved
0.5692 Remote Similarity NPD8340 Approved
0.5692 Remote Similarity NPD8299 Approved
0.5692 Remote Similarity NPD8342 Approved
0.5683 Remote Similarity NPD2567 Approved
0.5683 Remote Similarity NPD2569 Approved
0.5672 Remote Similarity NPD5204 Approved
0.5667 Remote Similarity NPD5704 Approved
0.5667 Remote Similarity NPD5706 Approved
0.5667 Remote Similarity NPD5705 Approved
0.566 Remote Similarity NPD5209 Approved
0.5659 Remote Similarity NPD2838 Clinical (unspecified phase)
0.5656 Remote Similarity NPD5240 Approved
0.5656 Remote Similarity NPD5239 Approved
0.5656 Remote Similarity NPD5236 Approved
0.5656 Remote Similarity NPD5237 Approved
0.5656 Remote Similarity NPD5235 Approved
0.5638 Remote Similarity NPD9418 Clinical (unspecified phase)
0.563 Remote Similarity NPD4620 Approved
0.563 Remote Similarity NPD4617 Approved
0.563 Remote Similarity NPD6845 Suspended
0.563 Remote Similarity NPD5201 Approved
0.563 Remote Similarity NPD5203 Approved
0.5625 Remote Similarity NPD6411 Approved
0.5607 Remote Similarity NPD7154 Phase 3
0.5606 Remote Similarity NPD7747 Phase 1
0.5606 Remote Similarity NPD7746 Phase 1

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data