Structure

Physi-Chem Properties

Molecular Weight:  733.34
Volume:  732.361
LogP:  4.771
LogD:  2.793
LogS:  -4.365
# Rotatable Bonds:  10
TPSA:  229.8
# H-Bond Aceptor:  16
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.094
Synthetic Accessibility Score:  5.675
Fsp3:  0.611
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.426
MDCK Permeability:  7.952787564136088e-05
Pgp-inhibitor:  0.996
Pgp-substrate:  0.971
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.027
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.047
Plasma Protein Binding (PPB):  84.93463897705078%
Volume Distribution (VD):  0.564
Pgp-substrate:  5.627335071563721%

ADMET: Metabolism

CYP1A2-inhibitor:  0.014
CYP1A2-substrate:  0.035
CYP2C19-inhibitor:  0.118
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.449
CYP2C9-substrate:  0.115
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.094
CYP3A4-inhibitor:  0.781
CYP3A4-substrate:  0.285

ADMET: Excretion

Clearance (CL):  3.855
Half-life (T1/2):  0.119

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.905
Drug-inuced Liver Injury (DILI):  0.949
AMES Toxicity:  0.016
Rat Oral Acute Toxicity:  0.023
Maximum Recommended Daily Dose:  0.164
Skin Sensitization:  0.137
Carcinogencity:  0.273
Eye Corrosion:  0.003
Eye Irritation:  0.02
Respiratory Toxicity:  0.147

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  Natural Product: NPC477392

Natural Product ID:  NPC477392
Common Name*:   Valyl-respirantin
IUPAC Name:   N-[(2S,5S,8S,13S,16R,17S)-5-butan-2-yl-2,10,10,16-tetramethyl-8-(2-methylpropyl)-3,6,9,11,14,18-hexaoxo-13-propan-2-yl-1,4,12,15-tetraoxa-7-azacyclooctadec-17-yl]-3-formamido-2-hydroxybenzamide
Synonyms:  
Standard InCHIKey:  NBVBHNUFSYRTEN-OQFKUZRZSA-N
Standard InCHI:  InChI=1S/C36H51N3O13/c1-11-19(6)28-31(44)38-24(15-17(2)3)29(42)36(9,10)35(48)52-27(18(4)5)34(47)49-20(7)25(33(46)50-21(8)32(45)51-28)39-30(43)22-13-12-14-23(26(22)41)37-16-40/h12-14,16-21,24-25,27-28,41H,11,15H2,1-10H3,(H,37,40)(H,38,44)(H,39,43)/t19?,20-,21+,24+,25+,27+,28+/m1/s1
SMILES:  CCC(C)[C@H]1C(=O)N[C@H](C(=O)C(C(=O)O[C@H](C(=O)O[C@@H]([C@@H](C(=O)O[C@H](C(=O)O1)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)C(C)C)(C)C)CC(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   23634473
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0001961] Depsipeptides
          • [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344559]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344578]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10348041]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10604756]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10695669]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10724004]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10994816]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11099231]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11132958]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11374972]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11473415]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14738393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Australian n.a. PMID[15497950]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15813185]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15844966]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15974616]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16180833]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1666120]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724845]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16830891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16872146]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17125235]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17315965]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17551212]
NPO33536 Kitasatospora sp. Species Streptomycetaceae Bacteria n.a. Prudhoe Bay (Beaufort Sea), Alaska n.a. PMID[17608530]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17608531]
NPO33536 Kitasatospora sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17608531]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17844998]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17887721]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17917237]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18044841]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Indonesian n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Northwest Territories, Canada 1995 PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18666798]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18776684]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19007176]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19129624]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19191549]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19856955]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19883065]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20092333]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20545334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20836523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028889]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21090727]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21314175]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21639131]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21728289]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21751787]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21807523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21873059]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21879726]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[22145663]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22574670]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22583058]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22591466]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22758660]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22775474]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23387796]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23662937]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24592993]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24754815]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24878306]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24964393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25211234]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25455147]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25495422]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25537064]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25918793]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25934225]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26035239]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26465675]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26798949]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26905826]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31013087]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31298537]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31894983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32298122]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8501018]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[8784423]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8931733]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8982334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031666]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031676]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066767]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066768]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9186568]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9531983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[9711246]

☑ 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
NPT168 Cell Line P388 Mus musculus ED50 = 0.033 ug/ml PMID[17608530]
NPT1081 Cell Line BXPC-3 Homo sapiens GI50 = 1.2 ug/ml PMID[17608530]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 0.00064 ug/ml PMID[17608530]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 0.016 ug/ml PMID[17608530]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 0.00063 ug/ml PMID[17608530]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 = 0.00058 ug/ml PMID[17608530]
NPT90 Cell Line DU-145 Homo sapiens GI50 < 0.0001 ug/ml PMID[17608530]
NPT168 Cell Line P388 Mus musculus GI50 = 0.033 ug/ml PMID[17608531]
NPT1081 Cell Line BXPC-3 Homo sapiens GI50 = 1.2 ug/ml PMID[17608531]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 0.00062 ug/ml PMID[17608531]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 0.016 ug/ml PMID[17608531]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 0.00063 ug/ml PMID[17608531]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 = 0.00058 ug/ml PMID[17608531]
NPT90 Cell Line DU-145 Homo sapiens GI50 < 0.0001 ug/ml PMID[17608531]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 64 ug/ml PMID[17608530]

☑ 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 NPC477392 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
1.0 High Similarity NPC315934
0.9699 High Similarity NPC477391
0.8988 High Similarity NPC95412
0.8869 High Similarity NPC83241
0.7262 Intermediate Similarity NPC6570
0.7202 Intermediate Similarity NPC70340
0.7193 Intermediate Similarity NPC91953
0.7168 Intermediate Similarity NPC323798
0.7135 Intermediate Similarity NPC197921
0.7115 Intermediate Similarity NPC314270
0.705 Intermediate Similarity NPC472330
0.705 Intermediate Similarity NPC472329
0.7031 Intermediate Similarity NPC132751
0.7005 Intermediate Similarity NPC225381
0.6995 Remote Similarity NPC475983
0.6994 Remote Similarity NPC469360
0.6989 Remote Similarity NPC196091
0.6977 Remote Similarity NPC471201
0.6947 Remote Similarity NPC126515
0.6947 Remote Similarity NPC472331
0.6947 Remote Similarity NPC274002
0.6946 Remote Similarity NPC296712
0.6936 Remote Similarity NPC181526
0.6907 Remote Similarity NPC288854
0.6885 Remote Similarity NPC476194
0.68 Remote Similarity NPC314113
0.6791 Remote Similarity NPC314861
0.6789 Remote Similarity NPC26108
0.6782 Remote Similarity NPC322526
0.6776 Remote Similarity NPC207675
0.6776 Remote Similarity NPC212699
0.6776 Remote Similarity NPC56635
0.6768 Remote Similarity NPC190663
0.676 Remote Similarity NPC132771
0.6751 Remote Similarity NPC295287
0.6725 Remote Similarity NPC45191
0.6724 Remote Similarity NPC473055
0.6724 Remote Similarity NPC473052
0.672 Remote Similarity NPC72291
0.6719 Remote Similarity NPC315631
0.6718 Remote Similarity NPC471048
0.6718 Remote Similarity NPC294951
0.6718 Remote Similarity NPC471049
0.6718 Remote Similarity NPC471050
0.6702 Remote Similarity NPC279871
0.6687 Remote Similarity NPC160493
0.6686 Remote Similarity NPC328070
0.6684 Remote Similarity NPC475421
0.6667 Remote Similarity NPC80150
0.6667 Remote Similarity NPC478015
0.6667 Remote Similarity NPC478016
0.6667 Remote Similarity NPC478014
0.6634 Remote Similarity NPC214368
0.6632 Remote Similarity NPC471568
0.6632 Remote Similarity NPC473693
0.6631 Remote Similarity NPC57105
0.6629 Remote Similarity NPC106183
0.6628 Remote Similarity NPC313466
0.6607 Remote Similarity NPC476241
0.6607 Remote Similarity NPC476260
0.6606 Remote Similarity NPC227033
0.6605 Remote Similarity NPC313804
0.6605 Remote Similarity NPC315804
0.6599 Remote Similarity NPC315542
0.6598 Remote Similarity NPC269750
0.6598 Remote Similarity NPC194671
0.6596 Remote Similarity NPC139506
0.6596 Remote Similarity NPC292143
0.6593 Remote Similarity NPC162104
0.6591 Remote Similarity NPC268841
0.6591 Remote Similarity NPC307357
0.6591 Remote Similarity NPC46098
0.6588 Remote Similarity NPC476353
0.6587 Remote Similarity NPC474862
0.6582 Remote Similarity NPC167763
0.6582 Remote Similarity NPC470112
0.6582 Remote Similarity NPC470903
0.6579 Remote Similarity NPC186617
0.6578 Remote Similarity NPC231862
0.6575 Remote Similarity NPC315829
0.6573 Remote Similarity NPC314817
0.6573 Remote Similarity NPC316297
0.6573 Remote Similarity NPC66191
0.6568 Remote Similarity NPC476179
0.6568 Remote Similarity NPC476125
0.6566 Remote Similarity NPC476183
0.6562 Remote Similarity NPC248670
0.6556 Remote Similarity NPC145113
0.6552 Remote Similarity NPC108847
0.655 Remote Similarity NPC473305
0.655 Remote Similarity NPC163961
0.655 Remote Similarity NPC101372
0.6548 Remote Similarity NPC477816
0.6548 Remote Similarity NPC469829
0.6545 Remote Similarity NPC310467
0.6545 Remote Similarity NPC237420
0.6545 Remote Similarity NPC257354
0.6543 Remote Similarity NPC199737
0.6543 Remote Similarity NPC133470
0.6543 Remote Similarity NPC191863
0.6543 Remote Similarity NPC289776
0.6534 Remote Similarity NPC316574
0.6528 Remote Similarity NPC158277
0.6528 Remote Similarity NPC473354
0.6527 Remote Similarity NPC476281
0.6527 Remote Similarity NPC476184
0.6526 Remote Similarity NPC238430
0.6524 Remote Similarity NPC471203
0.6522 Remote Similarity NPC184161
0.6515 Remote Similarity NPC299806
0.6512 Remote Similarity NPC478147
0.651 Remote Similarity NPC310894
0.6494 Remote Similarity NPC244866
0.6488 Remote Similarity NPC323662
0.6485 Remote Similarity NPC169328
0.648 Remote Similarity NPC313708
0.6477 Remote Similarity NPC273755
0.6471 Remote Similarity NPC476218
0.6471 Remote Similarity NPC108804
0.6471 Remote Similarity NPC4974
0.6462 Remote Similarity NPC315406
0.6456 Remote Similarity NPC317727
0.645 Remote Similarity NPC476278
0.6443 Remote Similarity NPC159767
0.6443 Remote Similarity NPC155506
0.6443 Remote Similarity NPC227778
0.6443 Remote Similarity NPC471165
0.6442 Remote Similarity NPC311357
0.644 Remote Similarity NPC107938
0.644 Remote Similarity NPC294516
0.6437 Remote Similarity NPC275538
0.6436 Remote Similarity NPC28510
0.6436 Remote Similarity NPC291359
0.6432 Remote Similarity NPC39431
0.6432 Remote Similarity NPC313886
0.6422 Remote Similarity NPC476129
0.6422 Remote Similarity NPC476212
0.6422 Remote Similarity NPC476205
0.6422 Remote Similarity NPC476207
0.6422 Remote Similarity NPC476257
0.6422 Remote Similarity NPC259791
0.6422 Remote Similarity NPC476256
0.6422 Remote Similarity NPC476206
0.641 Remote Similarity NPC50016
0.6409 Remote Similarity NPC81026
0.6407 Remote Similarity NPC319950
0.6402 Remote Similarity NPC19023
0.6398 Remote Similarity NPC123011
0.6398 Remote Similarity NPC256689
0.6398 Remote Similarity NPC316403
0.6396 Remote Similarity NPC186351
0.6392 Remote Similarity NPC306804
0.6392 Remote Similarity NPC137627
0.6387 Remote Similarity NPC204179
0.6384 Remote Similarity NPC122542
0.6374 Remote Similarity NPC135121
0.6373 Remote Similarity NPC328763
0.6373 Remote Similarity NPC46009
0.6369 Remote Similarity NPC45777
0.6369 Remote Similarity NPC477061
0.6369 Remote Similarity NPC314252
0.6364 Remote Similarity NPC476321
0.6359 Remote Similarity NPC476227
0.6359 Remote Similarity NPC478049
0.6359 Remote Similarity NPC314948
0.6354 Remote Similarity NPC266741
0.6354 Remote Similarity NPC19555
0.6354 Remote Similarity NPC127362
0.6354 Remote Similarity NPC473502
0.6354 Remote Similarity NPC209463
0.6345 Remote Similarity NPC45037
0.6343 Remote Similarity NPC326966
0.634 Remote Similarity NPC89831
0.634 Remote Similarity NPC112336
0.634 Remote Similarity NPC474814
0.6335 Remote Similarity NPC63931
0.6333 Remote Similarity NPC176226
0.6333 Remote Similarity NPC197682
0.6332 Remote Similarity NPC471526
0.6332 Remote Similarity NPC469973
0.6332 Remote Similarity NPC469831
0.6329 Remote Similarity NPC473558
0.6324 Remote Similarity NPC67246
0.6324 Remote Similarity NPC33372
0.6324 Remote Similarity NPC241392
0.6323 Remote Similarity NPC244536
0.6322 Remote Similarity NPC325651
0.6319 Remote Similarity NPC314186
0.6318 Remote Similarity NPC282092
0.6307 Remote Similarity NPC470392
0.6306 Remote Similarity NPC477394
0.6304 Remote Similarity NPC146097
0.6304 Remote Similarity NPC339338
0.6304 Remote Similarity NPC227905
0.6303 Remote Similarity NPC14339
0.6301 Remote Similarity NPC199738
0.6301 Remote Similarity NPC210950
0.63 Remote Similarity NPC320394
0.6294 Remote Similarity NPC27581
0.6294 Remote Similarity NPC142577

  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 NPC477392 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
0.7031 Intermediate Similarity NPD6045 Phase 3
0.6995 Remote Similarity NPD3153 Approved
0.6995 Remote Similarity NPD3154 Approved
0.6788 Remote Similarity NPD6104 Discontinued
0.6753 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6751 Remote Similarity NPD1898 Discontinued
0.6736 Remote Similarity NPD6184 Discontinued
0.6705 Remote Similarity NPD7978 Discontinued
0.6703 Remote Similarity NPD7972 Discontinued
0.6703 Remote Similarity NPD4003 Phase 3
0.6685 Remote Similarity NPD1196 Approved
0.6685 Remote Similarity NPD3400 Discontinued
0.6685 Remote Similarity NPD6913 Approved
0.6667 Remote Similarity NPD6807 Phase 3
0.6667 Remote Similarity NPD4738 Phase 2
0.6667 Remote Similarity NPD3136 Phase 2
0.6633 Remote Similarity NPD7628 Phase 3
0.6633 Remote Similarity NPD7630 Phase 3
0.6633 Remote Similarity NPD7629 Clinical (unspecified phase)
0.6629 Remote Similarity NPD1195 Approved
0.6606 Remote Similarity NPD8067 Phase 3
0.6596 Remote Similarity NPD3453 Discontinued
0.6575 Remote Similarity NPD1543 Discontinued
0.6569 Remote Similarity NPD4668 Phase 2
0.6564 Remote Similarity NPD6211 Clinical (unspecified phase)
0.655 Remote Similarity NPD4258 Approved
0.655 Remote Similarity NPD4259 Approved
0.6545 Remote Similarity NPD1759 Phase 1
0.6534 Remote Similarity NPD9279 Approved
0.6532 Remote Similarity NPD1048 Approved
0.6529 Remote Similarity NPD2579 Approved
0.6526 Remote Similarity NPD7129 Suspended
0.6505 Remote Similarity NPD2366 Approved
0.6503 Remote Similarity NPD9509 Clinical (unspecified phase)
0.6494 Remote Similarity NPD5729 Clinical (unspecified phase)
0.6489 Remote Similarity NPD3558 Approved
0.6489 Remote Similarity NPD3559 Clinical (unspecified phase)
0.6489 Remote Similarity NPD3560 Approved
0.6489 Remote Similarity NPD3556 Approved
0.6489 Remote Similarity NPD3557 Approved
0.6485 Remote Similarity NPD1758 Phase 1
0.6473 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6462 Remote Similarity NPD3965 Phase 1
0.6456 Remote Similarity NPD5609 Approved
0.6456 Remote Similarity NPD6874 Approved
0.6456 Remote Similarity NPD5608 Approved
0.6439 Remote Similarity NPD4605 Approved
0.6439 Remote Similarity NPD4604 Approved
0.6438 Remote Similarity NPD8356 Approved
0.6417 Remote Similarity NPD980 Clinical (unspecified phase)
0.6406 Remote Similarity NPD7292 Approved
0.6396 Remote Similarity NPD8430 Approved
0.6373 Remote Similarity NPD4606 Clinical (unspecified phase)
0.6368 Remote Similarity NPD7302 Phase 3
0.6368 Remote Similarity NPD7300 Phase 3
0.6368 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3684 Discontinued
0.6354 Remote Similarity NPD2162 Clinical (unspecified phase)
0.635 Remote Similarity NPD8167 Discontinued
0.6349 Remote Similarity NPD4335 Clinical (unspecified phase)
0.6337 Remote Similarity NPD8025 Phase 2
0.6332 Remote Similarity NPD5034 Approved
0.6332 Remote Similarity NPD4955 Approved
0.6332 Remote Similarity NPD36 Approved
0.6332 Remote Similarity NPD5028 Approved
0.6332 Remote Similarity NPD5026 Approved
0.6332 Remote Similarity NPD4954 Approved
0.633 Remote Similarity NPD3067 Approved
0.6323 Remote Similarity NPD4086 Phase 1
0.6321 Remote Similarity NPD2247 Approved
0.6321 Remote Similarity NPD7043 Discontinued
0.6321 Remote Similarity NPD2249 Approved
0.631 Remote Similarity NPD1634 Approved
0.6304 Remote Similarity NPD6682 Clinical (unspecified phase)
0.63 Remote Similarity NPD5035 Approved
0.6296 Remote Similarity NPD3812 Clinical (unspecified phase)
0.6289 Remote Similarity NPD7608 Discontinued
0.6286 Remote Similarity NPD5848 Clinical (unspecified phase)
0.6281 Remote Similarity NPD5030 Phase 2
0.6281 Remote Similarity NPD8014 Clinical (unspecified phase)
0.628 Remote Similarity NPD8485 Approved
0.6277 Remote Similarity NPD6502 Phase 2
0.6275 Remote Similarity NPD5871 Discontinued
0.6263 Remote Similarity NPD6283 Phase 2
0.6262 Remote Similarity NPD7256 Discontinued
0.6257 Remote Similarity NPD1633 Approved
0.6256 Remote Similarity NPD7293 Approved
0.6256 Remote Similarity NPD1913 Phase 1
0.625 Remote Similarity NPD3141 Discontinued
0.625 Remote Similarity NPD7883 Discontinued
0.6244 Remote Similarity NPD2361 Approved
0.6243 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6238 Remote Similarity NPD7476 Discontinued
0.6237 Remote Similarity NPD6390 Discontinued
0.6231 Remote Similarity NPD7959 Clinical (unspecified phase)
0.6222 Remote Similarity NPD5788 Clinical (unspecified phase)
0.622 Remote Similarity NPD7565 Approved
0.6209 Remote Similarity NPD2498 Approved
0.6209 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6207 Remote Similarity NPD5037 Approved
0.6207 Remote Similarity NPD5038 Approved
0.6207 Remote Similarity NPD6793 Clinical (unspecified phase)
0.6203 Remote Similarity NPD8330 Clinical (unspecified phase)
0.6197 Remote Similarity NPD6905 Phase 2
0.6195 Remote Similarity NPD5077 Approved
0.6195 Remote Similarity NPD5076 Approved
0.6193 Remote Similarity NPD2359 Approved
0.619 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6186 Remote Similarity NPD8367 Approved
0.6176 Remote Similarity NPD8370 Discontinued
0.6167 Remote Similarity NPD8461 Discontinued
0.6158 Remote Similarity NPD2672 Discontinued
0.6158 Remote Similarity NPD5036 Approved
0.6154 Remote Similarity NPD7083 Clinical (unspecified phase)
0.6154 Remote Similarity NPD2821 Approved
0.6151 Remote Similarity NPD8492 Approved
0.615 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6146 Remote Similarity NPD2996 Approved
0.6142 Remote Similarity NPD2246 Approved
0.6142 Remote Similarity NPD3952 Approved
0.6142 Remote Similarity NPD3951 Phase 3
0.6142 Remote Similarity NPD2248 Approved
0.6142 Remote Similarity NPD3953 Clinical (unspecified phase)
0.6135 Remote Similarity NPD5610 Approved
0.6126 Remote Similarity NPD8019 Approved
0.6122 Remote Similarity NPD1839 Phase 1
0.6114 Remote Similarity NPD6519 Phase 2
0.6101 Remote Similarity NPD7301 Phase 3
0.61 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6099 Remote Similarity NPD5507 Approved
0.6099 Remote Similarity NPD5506 Approved
0.6099 Remote Similarity NPD7805 Phase 3
0.6096 Remote Similarity NPD1664 Clinical (unspecified phase)
0.6094 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6091 Remote Similarity NPD7475 Clinical (unspecified phase)
0.6089 Remote Similarity NPD2802 Phase 3
0.6087 Remote Similarity NPD8146 Phase 2
0.608 Remote Similarity NPD659 Approved
0.608 Remote Similarity NPD663 Approved
0.608 Remote Similarity NPD662 Approved
0.608 Remote Similarity NPD656 Approved
0.608 Remote Similarity NPD658 Approved
0.6077 Remote Similarity NPD7880 Clinical (unspecified phase)
0.6075 Remote Similarity NPD4465 Phase 2
0.6075 Remote Similarity NPD4467 Phase 2
0.6073 Remote Similarity NPD7105 Phase 1
0.6073 Remote Similarity NPD3778 Approved
0.607 Remote Similarity NPD5445 Approved
0.607 Remote Similarity NPD3823 Discontinued
0.6068 Remote Similarity NPD8361 Approved
0.6068 Remote Similarity NPD8435 Approved
0.6068 Remote Similarity NPD8360 Approved
0.6062 Remote Similarity NPD7318 Phase 3
0.6061 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6059 Remote Similarity NPD2217 Approved
0.6059 Remote Similarity NPD2218 Phase 2
0.6056 Remote Similarity NPD555 Phase 2
0.6054 Remote Similarity NPD2575 Approved
0.6053 Remote Similarity NPD5811 Approved
0.6048 Remote Similarity NPD6161 Approved
0.6048 Remote Similarity NPD6162 Approved
0.6048 Remote Similarity NPD7282 Approved
0.6048 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6047 Remote Similarity NPD9692 Approved
0.6047 Remote Similarity NPD9693 Approved
0.6033 Remote Similarity NPD2578 Phase 3
0.6033 Remote Similarity NPD9277 Approved
0.6033 Remote Similarity NPD75 Approved
0.6033 Remote Similarity NPD4168 Approved
0.6032 Remote Similarity NPD7523 Phase 3
0.6029 Remote Similarity NPD5946 Clinical (unspecified phase)
0.6027 Remote Similarity NPD6298 Discontinued
0.6023 Remote Similarity NPD701 Approved
0.6023 Remote Similarity NPD698 Approved
0.6022 Remote Similarity NPD5595 Clinical (unspecified phase)
0.602 Remote Similarity NPD6746 Phase 2
0.602 Remote Similarity NPD3251 Approved
0.6019 Remote Similarity NPD5558 Clinical (unspecified phase)
0.6019 Remote Similarity NPD53 Approved
0.6019 Remote Similarity NPD7777 Approved
0.6019 Remote Similarity NPD7778 Approved
0.6012 Remote Similarity NPD4806 Approved
0.6012 Remote Similarity NPD4807 Approved
0.6011 Remote Similarity NPD9570 Approved
0.601 Remote Similarity NPD2215 Approved
0.601 Remote Similarity NPD2216 Approved
0.601 Remote Similarity NPD7687 Clinical (unspecified phase)
0.601 Remote Similarity NPD4083 Discontinued
0.601 Remote Similarity NPD7599 Phase 2
0.601 Remote Similarity NPD5032 Approved
0.601 Remote Similarity NPD5968 Phase 3
0.6009 Remote Similarity NPD6604 Discontinued
0.6 Remote Similarity NPD826 Approved
0.6 Remote Similarity NPD6325 Discontinued
0.6 Remote Similarity NPD825 Approved
0.6 Remote Similarity NPD6346 Approved
0.6 Remote Similarity NPD8265 Approved
0.6 Remote Similarity NPD7891 Discontinued
0.599 Remote Similarity NPD2034 Discontinued
0.599 Remote Similarity NPD6833 Clinical (unspecified phase)

  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