Structure

Physi-Chem Properties

Molecular Weight:  475.16
Volume:  476.509
LogP:  6.896
LogD:  3.981
LogS:  -4.772
# Rotatable Bonds:  2
TPSA:  82.28
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.217
Synthetic Accessibility Score:  5.313
Fsp3:  0.321
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.131
MDCK Permeability:  9.458202839596197e-06
Pgp-inhibitor:  0.082
Pgp-substrate:  0.096
Human Intestinal Absorption (HIA):  0.05
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.753

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  98.29764556884766%
Volume Distribution (VD):  0.326
Pgp-substrate:  2.334543466567993%

ADMET: Metabolism

CYP1A2-inhibitor:  0.94
CYP1A2-substrate:  0.206
CYP2C19-inhibitor:  0.889
CYP2C19-substrate:  0.093
CYP2C9-inhibitor:  0.923
CYP2C9-substrate:  0.814
CYP2D6-inhibitor:  0.687
CYP2D6-substrate:  0.189
CYP3A4-inhibitor:  0.158
CYP3A4-substrate:  0.359

ADMET: Excretion

Clearance (CL):  2.233
Half-life (T1/2):  0.058

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.694
Drug-inuced Liver Injury (DILI):  0.968
AMES Toxicity:  0.741
Rat Oral Acute Toxicity:  0.503
Maximum Recommended Daily Dose:  0.948
Skin Sensitization:  0.897
Carcinogencity:  0.89
Eye Corrosion:  0.003
Eye Irritation:  0.065
Respiratory Toxicity:  0.944

Download Data

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General Info & Identifiers & Properties  
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Similar NPs/Drugs  

  Natural Product: NPC477998

Natural Product ID:  NPC477998
Common Name*:   (1R,21S,22S,23R)-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.02,19.05,18.07,16.08,13]pentacosa-2(19),3,5(18),7(16),8(13),9,11,14-octaene-6,17-dione
IUPAC Name:   (1R,21S,22S,23R)-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.02,19.05,18.07,16.08,13]pentacosa-2(19),3,5(18),7(16),8(13),9,11,14-octaene-6,17-dione
Synonyms:  
Standard InCHIKey:  FRAARNLUWMVPMQ-VFEZHZOWSA-N
Standard InCHI:  InChI=1S/C28H27NO4/c1-4-11-28-13-21(33-15(3)27(28)32)18-9-10-20-23(24(18)29-28)26(31)19-8-6-16-12-14(2)5-7-17(16)22(19)25(20)30/h5-10,12,15,21,27,29,32H,4,11,13H2,1-3H3/t15-,21-,27-,28+/m1/s1
SMILES:  CCC[C@@]12C[C@H](C3=C(N1)C4=C(C=C3)C(=O)C5=C(C4=O)C=CC6=C5C=CC(=C6)C)O[C@@H]([C@H]2O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   44445374
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003415] Angucyclines

*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]
NPO30376 Streptomyces 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. n.a. n.a. PMID[18081255]
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[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
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[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
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 60.5 nM PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 4.4 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 2.9 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 48 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 41 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 7.3 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 0.8 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 6.9 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 4.1 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 50 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 39 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 4.5 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 1.9 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 5.8 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 2.4 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 55 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 35 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 8 % PMID[17844998]
NPT179 Cell Line A2780 Homo sapiens Activity = 0.6 % PMID[17844998]
NPT2 Others Unspecified IC50 = 22 nM PMID[17844998]

☑ 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 NPC477998 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
0.9126 High Similarity NPC477999
0.7513 Intermediate Similarity NPC49184
0.7389 Intermediate Similarity NPC25961
0.7326 Intermediate Similarity NPC471743
0.73 Intermediate Similarity NPC475223
0.7268 Intermediate Similarity NPC313293
0.7264 Intermediate Similarity NPC246983
0.7264 Intermediate Similarity NPC475448
0.7246 Intermediate Similarity NPC298449
0.7225 Intermediate Similarity NPC470317
0.7186 Intermediate Similarity NPC311054
0.7186 Intermediate Similarity NPC112752
0.7157 Intermediate Similarity NPC222561
0.7121 Intermediate Similarity NPC21483
0.7121 Intermediate Similarity NPC198205
0.71 Intermediate Similarity NPC17677
0.7079 Intermediate Similarity NPC136573
0.7079 Intermediate Similarity NPC176371
0.7065 Intermediate Similarity NPC107828
0.7065 Intermediate Similarity NPC90358
0.705 Intermediate Similarity NPC198390
0.7005 Intermediate Similarity NPC182131
0.699 Remote Similarity NPC478075
0.6934 Remote Similarity NPC473837
0.6927 Remote Similarity NPC470579
0.6912 Remote Similarity NPC471489
0.6891 Remote Similarity NPC475094
0.6869 Remote Similarity NPC223590
0.6842 Remote Similarity NPC469915
0.6837 Remote Similarity NPC471742
0.6833 Remote Similarity NPC473486
0.6833 Remote Similarity NPC475316
0.6827 Remote Similarity NPC308943
0.6794 Remote Similarity NPC90185
0.6787 Remote Similarity NPC35390
0.6787 Remote Similarity NPC470631
0.6787 Remote Similarity NPC473781
0.6765 Remote Similarity NPC23080
0.6765 Remote Similarity NPC193906
0.6757 Remote Similarity NPC114808
0.6754 Remote Similarity NPC472118
0.6743 Remote Similarity NPC173295
0.6735 Remote Similarity NPC472163
0.6719 Remote Similarity NPC469671
0.6719 Remote Similarity NPC126676
0.6714 Remote Similarity NPC306644
0.6714 Remote Similarity NPC217903
0.6714 Remote Similarity NPC236424
0.6714 Remote Similarity NPC207873
0.6714 Remote Similarity NPC100573
0.6702 Remote Similarity NPC470971
0.6701 Remote Similarity NPC129624
0.67 Remote Similarity NPC329790
0.67 Remote Similarity NPC316405
0.6682 Remote Similarity NPC274842
0.6667 Remote Similarity NPC116178
0.6667 Remote Similarity NPC473667
0.6667 Remote Similarity NPC244856
0.6651 Remote Similarity NPC301292
0.6651 Remote Similarity NPC313112
0.6651 Remote Similarity NPC474366
0.665 Remote Similarity NPC241263
0.6648 Remote Similarity NPC43477
0.6635 Remote Similarity NPC288759
0.6621 Remote Similarity NPC251071
0.662 Remote Similarity NPC218303
0.6616 Remote Similarity NPC477159
0.6609 Remote Similarity NPC208522
0.6606 Remote Similarity NPC140311
0.6606 Remote Similarity NPC285254
0.6605 Remote Similarity NPC176113
0.6605 Remote Similarity NPC55470
0.6599 Remote Similarity NPC283810
0.6599 Remote Similarity NPC475685
0.6598 Remote Similarity NPC307640
0.6591 Remote Similarity NPC253476
0.659 Remote Similarity NPC122235
0.6588 Remote Similarity NPC315545
0.6588 Remote Similarity NPC314297
0.6585 Remote Similarity NPC476218
0.6585 Remote Similarity NPC108804
0.6558 Remote Similarity NPC321166
0.6558 Remote Similarity NPC232225
0.655 Remote Similarity NPC475844
0.6548 Remote Similarity NPC474041
0.6545 Remote Similarity NPC106593
0.6542 Remote Similarity NPC132385
0.654 Remote Similarity NPC313345
0.654 Remote Similarity NPC313796
0.654 Remote Similarity NPC315638
0.654 Remote Similarity NPC314855
0.6537 Remote Similarity NPC476212
0.6537 Remote Similarity NPC476129
0.6537 Remote Similarity NPC476257
0.6537 Remote Similarity NPC259791
0.6537 Remote Similarity NPC476206
0.6537 Remote Similarity NPC476205
0.6537 Remote Similarity NPC476256
0.6537 Remote Similarity NPC476207
0.6529 Remote Similarity NPC268534
0.6525 Remote Similarity NPC478045
0.6514 Remote Similarity NPC313582
0.6509 Remote Similarity NPC198160
0.6509 Remote Similarity NPC212123
0.65 Remote Similarity NPC97584
0.6495 Remote Similarity NPC314834
0.6493 Remote Similarity NPC133156
0.649 Remote Similarity NPC317727
0.6486 Remote Similarity NPC237649
0.6486 Remote Similarity NPC122886
0.6486 Remote Similarity NPC300596
0.6481 Remote Similarity NPC30749
0.6473 Remote Similarity NPC36607
0.6468 Remote Similarity NPC312645
0.646 Remote Similarity NPC30456
0.6458 Remote Similarity NPC313757
0.6453 Remote Similarity NPC226794
0.6447 Remote Similarity NPC475607
0.6441 Remote Similarity NPC471980
0.644 Remote Similarity NPC93653
0.644 Remote Similarity NPC320064
0.6435 Remote Similarity NPC305542
0.6432 Remote Similarity NPC329631
0.6429 Remote Similarity NPC96901
0.6429 Remote Similarity NPC211920
0.6429 Remote Similarity NPC177261
0.6425 Remote Similarity NPC215892
0.6425 Remote Similarity NPC329830
0.6425 Remote Similarity NPC242662
0.6425 Remote Similarity NPC299582
0.6425 Remote Similarity NPC170333
0.6425 Remote Similarity NPC7560
0.6425 Remote Similarity NPC191193
0.6425 Remote Similarity NPC321072
0.6422 Remote Similarity NPC474059
0.6416 Remote Similarity NPC475303
0.6416 Remote Similarity NPC475596
0.6416 Remote Similarity NPC474701
0.6415 Remote Similarity NPC314648
0.6415 Remote Similarity NPC268077
0.6414 Remote Similarity NPC474081
0.641 Remote Similarity NPC107836
0.6404 Remote Similarity NPC14994
0.6398 Remote Similarity NPC242000
0.6398 Remote Similarity NPC15987
0.6396 Remote Similarity NPC470548
0.6396 Remote Similarity NPC127026
0.6396 Remote Similarity NPC475594
0.6396 Remote Similarity NPC127720
0.6394 Remote Similarity NPC208553
0.6394 Remote Similarity NPC471606
0.6394 Remote Similarity NPC181964
0.6388 Remote Similarity NPC49547
0.6386 Remote Similarity NPC322621
0.6384 Remote Similarity NPC473506
0.6382 Remote Similarity NPC218594
0.6382 Remote Similarity NPC99043
0.6381 Remote Similarity NPC313274
0.638 Remote Similarity NPC170101
0.6373 Remote Similarity NPC139506
0.6373 Remote Similarity NPC204867
0.6373 Remote Similarity NPC284706
0.6373 Remote Similarity NPC327699
0.6373 Remote Similarity NPC292143
0.6372 Remote Similarity NPC477160
0.6368 Remote Similarity NPC207971
0.6364 Remote Similarity NPC144691
0.6364 Remote Similarity NPC316412
0.6364 Remote Similarity NPC234933
0.6364 Remote Similarity NPC84347
0.6364 Remote Similarity NPC315351
0.6364 Remote Similarity NPC473558
0.6358 Remote Similarity NPC285394
0.6358 Remote Similarity NPC192533
0.6356 Remote Similarity NPC13249
0.6356 Remote Similarity NPC124029
0.6355 Remote Similarity NPC90415
0.6355 Remote Similarity NPC276674
0.6355 Remote Similarity NPC33902
0.6355 Remote Similarity NPC262725
0.6354 Remote Similarity NPC27904
0.6351 Remote Similarity NPC316164
0.635 Remote Similarity NPC85613
0.6347 Remote Similarity NPC478048
0.6346 Remote Similarity NPC308895
0.6346 Remote Similarity NPC162653
0.6345 Remote Similarity NPC191310
0.6345 Remote Similarity NPC73280
0.6344 Remote Similarity NPC316841
0.6341 Remote Similarity NPC471623
0.6335 Remote Similarity NPC474533
0.6335 Remote Similarity NPC474534
0.6333 Remote Similarity NPC32200
0.6333 Remote Similarity NPC212163
0.6333 Remote Similarity NPC5374
0.6333 Remote Similarity NPC42286
0.6332 Remote Similarity NPC327769
0.633 Remote Similarity NPC114468
0.633 Remote Similarity NPC314223
0.633 Remote Similarity NPC89508

  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 NPC477998 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
0.7586 Intermediate Similarity NPD2737 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD2836 Approved
0.7405 Intermediate Similarity NPD5997 Discontinued
0.733 Intermediate Similarity NPD4888 Discontinued
0.7241 Intermediate Similarity NPD1625 Approved
0.7181 Intermediate Similarity NPD5919 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD5086 Approved
0.711 Intermediate Similarity NPD1626 Approved
0.7094 Intermediate Similarity NPD7597 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD6021 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD5498 Phase 2
0.7015 Intermediate Similarity NPD5196 Approved
0.7015 Intermediate Similarity NPD5197 Approved
0.7015 Intermediate Similarity NPD5194 Approved
0.6955 Remote Similarity NPD7922 Phase 1
0.6935 Remote Similarity NPD7569 Approved
0.6935 Remote Similarity NPD7570 Approved
0.6911 Remote Similarity NPD5466 Approved
0.6881 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6798 Remote Similarity NPD1189 Approved
0.6792 Remote Similarity NPD3794 Approved
0.6792 Remote Similarity NPD3795 Approved
0.6772 Remote Similarity NPD5430 Discontinued
0.6761 Remote Similarity NPD4562 Clinical (unspecified phase)
0.6751 Remote Similarity NPD7546 Discontinued
0.675 Remote Similarity NPD5896 Clinical (unspecified phase)
0.6742 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6734 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6733 Remote Similarity NPD6212 Phase 3
0.6733 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7262 Phase 1
0.6733 Remote Similarity NPD6213 Phase 3
0.6724 Remote Similarity NPD1874 Clinical (unspecified phase)
0.6705 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6703 Remote Similarity NPD8165 Discontinued
0.6684 Remote Similarity NPD7997 Clinical (unspecified phase)
0.6684 Remote Similarity NPD7854 Phase 2
0.6682 Remote Similarity NPD5433 Clinical (unspecified phase)
0.6651 Remote Similarity NPD8155 Clinical (unspecified phase)
0.665 Remote Similarity NPD6483 Approved
0.665 Remote Similarity NPD6484 Approved
0.6629 Remote Similarity NPD7713 Phase 3
0.6619 Remote Similarity NPD7010 Phase 3
0.6613 Remote Similarity NPD6591 Clinical (unspecified phase)
0.661 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6608 Remote Similarity NPD1574 Approved
0.6601 Remote Similarity NPD8146 Phase 2
0.6599 Remote Similarity NPD6293 Clinical (unspecified phase)
0.659 Remote Similarity NPD7395 Discontinued
0.6585 Remote Similarity NPD5411 Discontinued
0.6584 Remote Similarity NPD5928 Phase 1
0.658 Remote Similarity NPD5183 Approved
0.658 Remote Similarity NPD5186 Approved
0.658 Remote Similarity NPD2369 Discontinued
0.6574 Remote Similarity NPD8149 Discontinued
0.6561 Remote Similarity NPD3925 Approved
0.6557 Remote Similarity NPD7300 Phase 3
0.6557 Remote Similarity NPD7302 Phase 3
0.6557 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6545 Remote Similarity NPD6995 Phase 1
0.6543 Remote Similarity NPD2672 Discontinued
0.6542 Remote Similarity NPD1945 Phase 1
0.6542 Remote Similarity NPD5416 Discontinued
0.6524 Remote Similarity NPD2790 Discontinued
0.6522 Remote Similarity NPD4668 Phase 2
0.6522 Remote Similarity NPD7794 Clinical (unspecified phase)
0.6517 Remote Similarity NPD3153 Approved
0.6517 Remote Similarity NPD3154 Approved
0.6513 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6498 Remote Similarity NPD7475 Clinical (unspecified phase)
0.6493 Remote Similarity NPD6250 Discontinued
0.649 Remote Similarity NPD5608 Approved
0.649 Remote Similarity NPD5609 Approved
0.6486 Remote Similarity NPD7528 Approved
0.6484 Remote Similarity NPD7404 Approved
0.6479 Remote Similarity NPD4859 Phase 1
0.6474 Remote Similarity NPD1593 Approved
0.6456 Remote Similarity NPD6534 Approved
0.6456 Remote Similarity NPD6535 Approved
0.6453 Remote Similarity NPD7693 Approved
0.6452 Remote Similarity NPD5417 Clinical (unspecified phase)
0.645 Remote Similarity NPD3253 Clinical (unspecified phase)
0.645 Remote Similarity NPD8281 Discontinued
0.6442 Remote Similarity NPD5071 Phase 2
0.6442 Remote Similarity NPD7699 Phase 2
0.6442 Remote Similarity NPD7700 Phase 2
0.6432 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6432 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6414 Clinical (unspecified phase)
0.6425 Remote Similarity NPD7793 Clinical (unspecified phase)
0.6425 Remote Similarity NPD7880 Clinical (unspecified phase)
0.6425 Remote Similarity NPD7036 Phase 3
0.6425 Remote Similarity NPD7035 Approved
0.6422 Remote Similarity NPD4258 Approved
0.6422 Remote Similarity NPD4259 Approved
0.6417 Remote Similarity NPD1230 Approved
0.6415 Remote Similarity NPD8115 Approved
0.6415 Remote Similarity NPD8114 Approved
0.6415 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6413 Remote Similarity NPD6622 Phase 1
0.641 Remote Similarity NPD7795 Phase 2
0.6406 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6404 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6396 Remote Similarity NPD5938 Phase 3
0.6396 Remote Similarity NPD7324 Discontinued
0.6394 Remote Similarity NPD8485 Approved
0.6394 Remote Similarity NPD5195 Discontinued
0.639 Remote Similarity NPD5504 Discontinued
0.639 Remote Similarity NPD5042 Phase 1
0.6389 Remote Similarity NPD6342 Discontinued
0.6389 Remote Similarity NPD5475 Discontinued
0.6386 Remote Similarity NPD6163 Clinical (unspecified phase)
0.6384 Remote Similarity NPD8289 Discontinued
0.638 Remote Similarity NPD3280 Approved
0.6377 Remote Similarity NPD7256 Discontinued
0.6373 Remote Similarity NPD7444 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6372 Remote Similarity NPD4506 Discontinued
0.6368 Remote Similarity NPD2920 Discontinued
0.6359 Remote Similarity NPD7301 Phase 3
0.6358 Remote Similarity NPD5159 Phase 2
0.6358 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6358 Remote Similarity NPD5157 Phase 1
0.6355 Remote Similarity NPD5429 Discontinued
0.635 Remote Similarity NPD6654 Clinical (unspecified phase)
0.6349 Remote Similarity NPD2651 Approved
0.6349 Remote Similarity NPD2649 Approved
0.6344 Remote Similarity NPD1801 Approved
0.6344 Remote Similarity NPD1802 Approved
0.6341 Remote Similarity NPD8360 Approved
0.6341 Remote Similarity NPD8435 Approved
0.6341 Remote Similarity NPD8361 Approved
0.6335 Remote Similarity NPD7011 Discontinued
0.6335 Remote Similarity NPD6770 Approved
0.6328 Remote Similarity NPD6039 Approved
0.6328 Remote Similarity NPD7008 Discontinued
0.6326 Remote Similarity NPD7701 Phase 2
0.6324 Remote Similarity NPD6793 Clinical (unspecified phase)
0.6324 Remote Similarity NPD4951 Discontinued
0.6321 Remote Similarity NPD1210 Approved
0.6316 Remote Similarity NPD6162 Approved
0.6316 Remote Similarity NPD6161 Approved
0.6313 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6313 Remote Similarity NPD7940 Phase 3
0.6313 Remote Similarity NPD6316 Clinical (unspecified phase)
0.6313 Remote Similarity NPD3423 Phase 2
0.6313 Remote Similarity NPD3422 Phase 3
0.6308 Remote Similarity NPD8003 Clinical (unspecified phase)
0.6308 Remote Similarity NPD8002 Clinical (unspecified phase)
0.6304 Remote Similarity NPD4430 Phase 2
0.6303 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6781 Approved
0.6303 Remote Similarity NPD6780 Approved
0.6303 Remote Similarity NPD6778 Approved
0.6303 Remote Similarity NPD6782 Approved
0.6303 Remote Similarity NPD6779 Approved
0.6303 Remote Similarity NPD6776 Approved
0.6303 Remote Similarity NPD6777 Approved
0.63 Remote Similarity NPD5398 Clinical (unspecified phase)
0.63 Remote Similarity NPD7881 Approved
0.63 Remote Similarity NPD5022 Discontinued
0.63 Remote Similarity NPD4981 Phase 2
0.63 Remote Similarity NPD7479 Phase 2
0.6294 Remote Similarity NPD3776 Discontinued
0.6284 Remote Similarity NPD7455 Approved
0.6284 Remote Similarity NPD7454 Approved
0.6281 Remote Similarity NPD5603 Clinical (unspecified phase)
0.628 Remote Similarity NPD5937 Approved
0.6279 Remote Similarity NPD5143 Clinical (unspecified phase)
0.6274 Remote Similarity NPD7476 Discontinued
0.6273 Remote Similarity NPD3394 Approved
0.6273 Remote Similarity NPD3389 Approved
0.6273 Remote Similarity NPD3393 Approved
0.6272 Remote Similarity NPD7688 Phase 1
0.6272 Remote Similarity NPD6962 Phase 2
0.627 Remote Similarity NPD2387 Approved
0.627 Remote Similarity NPD5918 Discontinued
0.6269 Remote Similarity NPD3823 Discontinued
0.6268 Remote Similarity NPD6722 Clinical (unspecified phase)
0.6267 Remote Similarity NPD6204 Clinical (unspecified phase)
0.6263 Remote Similarity NPD6607 Clinical (unspecified phase)
0.6262 Remote Similarity NPD8320 Phase 1
0.6262 Remote Similarity NPD8319 Approved
0.6262 Remote Similarity NPD2564 Approved
0.6262 Remote Similarity NPD2565 Phase 2
0.6262 Remote Similarity NPD1294 Discontinued
0.6261 Remote Similarity NPD2899 Discontinued
0.6257 Remote Similarity NPD6758 Approved
0.6257 Remote Similarity NPD1527 Phase 2
0.6256 Remote Similarity NPD4412 Phase 2
0.6256 Remote Similarity NPD7654 Discontinued
0.6256 Remote Similarity NPD5923 Phase 1
0.6255 Remote Similarity NPD7921 Approved
0.625 Remote Similarity NPD8311 Discontinued
0.6244 Remote Similarity NPD7683 Discontinued
0.6244 Remote Similarity NPD3949 Clinical (unspecified phase)
0.6238 Remote Similarity NPD5003 Discontinued
0.6238 Remote Similarity NPD5637 Discontinued

  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