Structure

Physi-Chem Properties

Molecular Weight:  438.05
Volume:  411.323
LogP:  6.04
LogD:  2.427
LogS:  -3.677
# Rotatable Bonds:  1
TPSA:  116.45
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.142
Synthetic Accessibility Score:  3.465
Fsp3:  0.087
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:  -5.377
MDCK Permeability:  1.3749656318395864e-05
Pgp-inhibitor:  0.112
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.46
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  93.07952880859375%
Volume Distribution (VD):  0.454
Pgp-substrate:  12.17451286315918%

ADMET: Metabolism

CYP1A2-inhibitor:  0.549
CYP1A2-substrate:  0.299
CYP2C19-inhibitor:  0.112
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.716
CYP2C9-substrate:  0.454
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.147
CYP3A4-inhibitor:  0.049
CYP3A4-substrate:  0.045

ADMET: Excretion

Clearance (CL):  3.067
Half-life (T1/2):  0.329

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.022
Drug-inuced Liver Injury (DILI):  0.944
AMES Toxicity:  0.35
Rat Oral Acute Toxicity:  0.161
Maximum Recommended Daily Dose:  0.945
Skin Sensitization:  0.915
Carcinogencity:  0.094
Eye Corrosion:  0.004
Eye Irritation:  0.915
Respiratory Toxicity:  0.272

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  Natural Product: NPC313386

Natural Product ID:  NPC313386
Common Name*:   Chlorocyclinone D
IUPAC Name:   n.a.
Synonyms:   chlorocyclinone D
Standard InCHIKey:  RSSUHOCYQSARQQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C23H15ClO7/c1-7-4-9-5-12(25)16-17(14(9)22(30-3)18(7)24)19(26)10-6-11-13(8(2)31-23(11)29)20(27)15(10)21(16)28/h4-6,8,25,27H,1-3H3
SMILES:  COc1c(Cl)c(C)cc2c1c1C(=O)c3cc4C(=O)OC(c4c(c3C(=O)c1c(c2)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL400132
PubChem CID:   24762578
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. 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
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens IC50 = 320.0 nM PMID[518716]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens EC50 = 260.0 nM PMID[518716]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens IC50 = 4400.0 nM PMID[518716]

☑ 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 NPC313386 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
0.9769 High Similarity NPC316091
0.9535 High Similarity NPC306240
0.9441 High Similarity NPC313541
0.8857 High Similarity NPC470562
0.8807 High Similarity NPC470560
0.875 High Similarity NPC470565
0.8708 High Similarity NPC264922
0.8701 High Similarity NPC474857
0.8644 High Similarity NPC277865
0.8571 High Similarity NPC470563
0.8547 High Similarity NPC470422
0.8514 High Similarity NPC470561
0.8427 Intermediate Similarity NPC472032
0.8391 Intermediate Similarity NPC197326
0.8378 Intermediate Similarity NPC191606
0.8315 Intermediate Similarity NPC151292
0.8239 Intermediate Similarity NPC470559
0.8167 Intermediate Similarity NPC477835
0.8156 Intermediate Similarity NPC470081
0.8152 Intermediate Similarity NPC45072
0.8146 Intermediate Similarity NPC298401
0.8125 Intermediate Similarity NPC470564
0.8111 Intermediate Similarity NPC58653
0.8111 Intermediate Similarity NPC173352
0.8101 Intermediate Similarity NPC474096
0.8101 Intermediate Similarity NPC473696
0.8087 Intermediate Similarity NPC477836
0.8081 Intermediate Similarity NPC119767
0.8079 Intermediate Similarity NPC263483
0.8066 Intermediate Similarity NPC28669
0.8063 Intermediate Similarity NPC220369
0.8063 Intermediate Similarity NPC221185
0.8046 Intermediate Similarity NPC119929
0.8046 Intermediate Similarity NPC205766
0.8041 Intermediate Similarity NPC154720
0.8034 Intermediate Similarity NPC324736
0.8021 Intermediate Similarity NPC214901
0.8021 Intermediate Similarity NPC247104
0.8 Intermediate Similarity NPC477568
0.7989 Intermediate Similarity NPC473113
0.7978 Intermediate Similarity NPC472404
0.7967 Intermediate Similarity NPC474061
0.7966 Intermediate Similarity NPC66508
0.7966 Intermediate Similarity NPC66029
0.7966 Intermediate Similarity NPC226656
0.7958 Intermediate Similarity NPC470100
0.7958 Intermediate Similarity NPC470099
0.7947 Intermediate Similarity NPC474499
0.7946 Intermediate Similarity NPC472054
0.7944 Intermediate Similarity NPC24761
0.7943 Intermediate Similarity NPC470568
0.7943 Intermediate Similarity NPC147735
0.7937 Intermediate Similarity NPC99937
0.7921 Intermediate Similarity NPC474360
0.7919 Intermediate Similarity NPC147250
0.7914 Intermediate Similarity NPC472606
0.7912 Intermediate Similarity NPC68850
0.791 Intermediate Similarity NPC208806
0.791 Intermediate Similarity NPC214632
0.7898 Intermediate Similarity NPC470569
0.7889 Intermediate Similarity NPC472060
0.7889 Intermediate Similarity NPC470342
0.7889 Intermediate Similarity NPC472052
0.7874 Intermediate Similarity NPC118027
0.7874 Intermediate Similarity NPC289042
0.7874 Intermediate Similarity NPC245584
0.7874 Intermediate Similarity NPC312929
0.7874 Intermediate Similarity NPC56433
0.7874 Intermediate Similarity NPC190648
0.7874 Intermediate Similarity NPC126767
0.7853 Intermediate Similarity NPC40356
0.7853 Intermediate Similarity NPC175978
0.7853 Intermediate Similarity NPC154683
0.7849 Intermediate Similarity NPC66593
0.7846 Intermediate Similarity NPC198163
0.7845 Intermediate Similarity NPC472261
0.7845 Intermediate Similarity NPC472405
0.7841 Intermediate Similarity NPC294646
0.7841 Intermediate Similarity NPC255641
0.7841 Intermediate Similarity NPC290954
0.7829 Intermediate Similarity NPC172329
0.7829 Intermediate Similarity NPC2569
0.7826 Intermediate Similarity NPC473094
0.7826 Intermediate Similarity NPC105414
0.7826 Intermediate Similarity NPC324522
0.7826 Intermediate Similarity NPC76647
0.7826 Intermediate Similarity NPC472058
0.7826 Intermediate Similarity NPC470341
0.7826 Intermediate Similarity NPC234497
0.7821 Intermediate Similarity NPC146211
0.7821 Intermediate Similarity NPC180924
0.7819 Intermediate Similarity NPC471802
0.7817 Intermediate Similarity NPC108744
0.7795 Intermediate Similarity NPC48822
0.7791 Intermediate Similarity NPC69755
0.779 Intermediate Similarity NPC470810
0.779 Intermediate Similarity NPC284495
0.7784 Intermediate Similarity NPC148480
0.7784 Intermediate Similarity NPC473095
0.7784 Intermediate Similarity NPC473096
0.7778 Intermediate Similarity NPC317580
0.7778 Intermediate Similarity NPC67197
0.7778 Intermediate Similarity NPC164110
0.7778 Intermediate Similarity NPC96342
0.7778 Intermediate Similarity NPC246647
0.7778 Intermediate Similarity NPC212967
0.7772 Intermediate Similarity NPC30027
0.7771 Intermediate Similarity NPC478018
0.7765 Intermediate Similarity NPC318270
0.7747 Intermediate Similarity NPC18380
0.7742 Intermediate Similarity NPC477571
0.7742 Intermediate Similarity NPC477573
0.7742 Intermediate Similarity NPC477572
0.7735 Intermediate Similarity NPC326084
0.7727 Intermediate Similarity NPC153417
0.7725 Intermediate Similarity NPC207467
0.7722 Intermediate Similarity NPC474861
0.7722 Intermediate Similarity NPC478223
0.772 Intermediate Similarity NPC471812
0.772 Intermediate Similarity NPC471803
0.772 Intermediate Similarity NPC471804
0.7717 Intermediate Similarity NPC469664
0.7714 Intermediate Similarity NPC470570
0.7714 Intermediate Similarity NPC314437
0.7714 Intermediate Similarity NPC300540
0.7713 Intermediate Similarity NPC68381
0.7709 Intermediate Similarity NPC477691
0.7705 Intermediate Similarity NPC245122
0.7705 Intermediate Similarity NPC15374
0.7705 Intermediate Similarity NPC478229
0.7701 Intermediate Similarity NPC48762
0.7701 Intermediate Similarity NPC471305
0.7701 Intermediate Similarity NPC19896
0.7697 Intermediate Similarity NPC474417
0.7697 Intermediate Similarity NPC149526
0.7697 Intermediate Similarity NPC72958
0.7697 Intermediate Similarity NPC232645
0.7696 Intermediate Similarity NPC470332
0.7692 Intermediate Similarity NPC186325
0.7692 Intermediate Similarity NPC475449
0.7692 Intermediate Similarity NPC292863
0.7692 Intermediate Similarity NPC184326
0.7692 Intermediate Similarity NPC476506
0.7692 Intermediate Similarity NPC47623
0.7684 Intermediate Similarity NPC299149
0.7684 Intermediate Similarity NPC114257
0.7684 Intermediate Similarity NPC471801
0.7684 Intermediate Similarity NPC473785
0.7684 Intermediate Similarity NPC70318
0.7684 Intermediate Similarity NPC153578
0.7684 Intermediate Similarity NPC277710
0.768 Intermediate Similarity NPC296044
0.768 Intermediate Similarity NPC167098
0.768 Intermediate Similarity NPC121100
0.768 Intermediate Similarity NPC201127
0.768 Intermediate Similarity NPC39409
0.768 Intermediate Similarity NPC143328
0.7676 Intermediate Similarity NPC29160
0.7676 Intermediate Similarity NPC125465
0.7672 Intermediate Similarity NPC324220
0.7672 Intermediate Similarity NPC475233
0.7672 Intermediate Similarity NPC312630
0.767 Intermediate Similarity NPC34802
0.767 Intermediate Similarity NPC8817
0.767 Intermediate Similarity NPC137296
0.7667 Intermediate Similarity NPC3898
0.7667 Intermediate Similarity NPC148938
0.7665 Intermediate Similarity NPC193676
0.7663 Intermediate Similarity NPC100849
0.766 Intermediate Similarity NPC98776
0.766 Intermediate Similarity NPC470333
0.766 Intermediate Similarity NPC85368
0.7657 Intermediate Similarity NPC75694
0.7657 Intermediate Similarity NPC478019
0.7657 Intermediate Similarity NPC34482
0.7654 Intermediate Similarity NPC217447
0.7654 Intermediate Similarity NPC273483
0.7654 Intermediate Similarity NPC87708
0.7654 Intermediate Similarity NPC477690
0.7654 Intermediate Similarity NPC271681
0.765 Intermediate Similarity NPC269117
0.765 Intermediate Similarity NPC472157
0.765 Intermediate Similarity NPC273467
0.765 Intermediate Similarity NPC137232
0.765 Intermediate Similarity NPC478134
0.765 Intermediate Similarity NPC189552
0.7647 Intermediate Similarity NPC107283
0.7647 Intermediate Similarity NPC474004
0.7644 Intermediate Similarity NPC315221
0.7644 Intermediate Similarity NPC53016
0.7641 Intermediate Similarity NPC471810
0.7641 Intermediate Similarity NPC471806
0.7641 Intermediate Similarity NPC471807
0.764 Intermediate Similarity NPC295036
0.764 Intermediate Similarity NPC202595
0.764 Intermediate Similarity NPC315520
0.764 Intermediate Similarity NPC477914
0.764 Intermediate Similarity NPC474660
0.764 Intermediate Similarity NPC470107
0.7637 Intermediate Similarity NPC472877

  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 NPC313386 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
0.7784 Intermediate Similarity NPD3226 Approved
0.7747 Intermediate Similarity NPD6959 Discontinued
0.7705 Intermediate Similarity NPD6232 Discontinued
0.7676 Intermediate Similarity NPD7473 Discontinued
0.7657 Intermediate Similarity NPD2534 Approved
0.7657 Intermediate Similarity NPD2532 Approved
0.7657 Intermediate Similarity NPD2533 Approved
0.7527 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7411 Suspended
0.7486 Intermediate Similarity NPD3749 Approved
0.7418 Intermediate Similarity NPD7819 Suspended
0.7407 Intermediate Similarity NPD5844 Phase 1
0.7398 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD2403 Approved
0.7337 Intermediate Similarity NPD7768 Phase 2
0.7299 Intermediate Similarity NPD5408 Approved
0.7299 Intermediate Similarity NPD5404 Approved
0.7299 Intermediate Similarity NPD5406 Approved
0.7299 Intermediate Similarity NPD5405 Approved
0.7283 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD2346 Discontinued
0.7241 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD8312 Approved
0.7216 Intermediate Similarity NPD8313 Approved
0.7207 Intermediate Similarity NPD7390 Discontinued
0.7202 Intermediate Similarity NPD6559 Discontinued
0.72 Intermediate Similarity NPD2935 Discontinued
0.7198 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD4380 Phase 2
0.7151 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5711 Approved
0.7143 Intermediate Similarity NPD2370 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5710 Approved
0.7135 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7003 Approved
0.7115 Intermediate Similarity NPD8151 Discontinued
0.7112 Intermediate Similarity NPD7075 Discontinued
0.7083 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD4363 Phase 3
0.7065 Intermediate Similarity NPD4360 Phase 2
0.7062 Intermediate Similarity NPD2344 Approved
0.7045 Intermediate Similarity NPD1510 Phase 2
0.7043 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD7435 Discontinued
0.7039 Intermediate Similarity NPD3750 Approved
0.7037 Intermediate Similarity NPD5494 Approved
0.7029 Intermediate Similarity NPD1607 Approved
0.7022 Intermediate Similarity NPD1549 Phase 2
0.6995 Remote Similarity NPD7177 Discontinued
0.6995 Remote Similarity NPD920 Approved
0.6994 Remote Similarity NPD3764 Approved
0.6989 Remote Similarity NPD1934 Approved
0.6976 Remote Similarity NPD6778 Approved
0.6976 Remote Similarity NPD6776 Approved
0.6976 Remote Similarity NPD6779 Approved
0.6976 Remote Similarity NPD6782 Approved
0.6976 Remote Similarity NPD6780 Approved
0.6976 Remote Similarity NPD6781 Approved
0.6976 Remote Similarity NPD6777 Approved
0.6966 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6946 Remote Similarity NPD4361 Phase 2
0.6946 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6935 Remote Similarity NPD8150 Discontinued
0.6923 Remote Similarity NPD7870 Phase 2
0.6923 Remote Similarity NPD7871 Phase 2
0.6919 Remote Similarity NPD7458 Discontinued
0.6914 Remote Similarity NPD1240 Approved
0.6907 Remote Similarity NPD3818 Discontinued
0.6906 Remote Similarity NPD2309 Approved
0.6898 Remote Similarity NPD6801 Discontinued
0.6891 Remote Similarity NPD6166 Phase 2
0.6891 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6891 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6889 Remote Similarity NPD1243 Approved
0.6889 Remote Similarity NPD2800 Approved
0.6888 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6885 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6885 Remote Similarity NPD1578 Phase 2
0.6885 Remote Similarity NPD642 Clinical (unspecified phase)
0.6882 Remote Similarity NPD6599 Discontinued
0.6878 Remote Similarity NPD3882 Suspended
0.6875 Remote Similarity NPD7697 Approved
0.6875 Remote Similarity NPD7229 Phase 3
0.6875 Remote Similarity NPD7696 Phase 3
0.6875 Remote Similarity NPD7698 Approved
0.6872 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6862 Remote Similarity NPD1465 Phase 2
0.6854 Remote Similarity NPD2799 Discontinued
0.6851 Remote Similarity NPD4628 Phase 3
0.6848 Remote Similarity NPD6273 Approved
0.6842 Remote Similarity NPD4381 Clinical (unspecified phase)
0.684 Remote Similarity NPD7875 Clinical (unspecified phase)
0.684 Remote Similarity NPD7874 Approved
0.6816 Remote Similarity NPD1551 Phase 2
0.6816 Remote Similarity NPD2796 Approved
0.6813 Remote Similarity NPD3887 Approved
0.6813 Remote Similarity NPD2354 Approved
0.6809 Remote Similarity NPD37 Approved
0.6806 Remote Similarity NPD6234 Discontinued
0.6802 Remote Similarity NPD1470 Approved
0.68 Remote Similarity NPD8055 Clinical (unspecified phase)
0.68 Remote Similarity NPD6785 Approved
0.68 Remote Similarity NPD6784 Approved
0.68 Remote Similarity NPD2313 Discontinued
0.6789 Remote Similarity NPD4967 Phase 2
0.6789 Remote Similarity NPD4965 Approved
0.6789 Remote Similarity NPD4966 Approved
0.6778 Remote Similarity NPD1471 Phase 3
0.6776 Remote Similarity NPD643 Clinical (unspecified phase)
0.6772 Remote Similarity NPD2801 Approved
0.6766 Remote Similarity NPD8434 Phase 2
0.676 Remote Similarity NPD3748 Approved
0.6758 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6755 Remote Similarity NPD958 Approved
0.6745 Remote Similarity NPD7701 Phase 2
0.6739 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6739 Remote Similarity NPD1511 Approved
0.6739 Remote Similarity NPD6799 Approved
0.6739 Remote Similarity NPD7041 Phase 2
0.6737 Remote Similarity NPD3817 Phase 2
0.6737 Remote Similarity NPD5402 Approved
0.6736 Remote Similarity NPD1247 Approved
0.6735 Remote Similarity NPD3751 Discontinued
0.6732 Remote Similarity NPD6535 Approved
0.6732 Remote Similarity NPD6534 Approved
0.6729 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6729 Remote Similarity NPD7783 Phase 2
0.6719 Remote Similarity NPD919 Approved
0.6717 Remote Similarity NPD5953 Discontinued
0.6701 Remote Similarity NPD6808 Phase 2
0.6701 Remote Similarity NPD7804 Clinical (unspecified phase)
0.67 Remote Similarity NPD4287 Approved
0.6685 Remote Similarity NPD2353 Approved
0.6685 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6684 Remote Similarity NPD957 Approved
0.6683 Remote Similarity NPD8285 Discontinued
0.6682 Remote Similarity NPD8320 Phase 1
0.6682 Remote Similarity NPD8319 Approved
0.6667 Remote Similarity NPD7074 Phase 3
0.6667 Remote Similarity NPD6823 Phase 2
0.6667 Remote Similarity NPD1512 Approved
0.6651 Remote Similarity NPD7801 Approved
0.665 Remote Similarity NPD7228 Approved
0.665 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6649 Remote Similarity NPD2379 Clinical (unspecified phase)
0.6649 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6647 Remote Similarity NPD1283 Approved
0.6635 Remote Similarity NPD7700 Phase 2
0.6635 Remote Similarity NPD7699 Phase 2
0.6631 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6629 Remote Similarity NPD454 Approved
0.6616 Remote Similarity NPD7054 Approved
0.6616 Remote Similarity NPD7286 Phase 2
0.661 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6606 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6602 Remote Similarity NPD6213 Phase 3
0.6602 Remote Similarity NPD6212 Phase 3
0.6602 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6595 Remote Similarity NPD5058 Phase 3
0.6583 Remote Similarity NPD7472 Approved
0.6582 Remote Similarity NPD3926 Phase 2
0.6578 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6576 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6575 Remote Similarity NPD5588 Approved
0.657 Remote Similarity NPD1201 Approved
0.655 Remote Similarity NPD6797 Phase 2
0.6546 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6543 Remote Similarity NPD5403 Approved
0.6536 Remote Similarity NPD2979 Phase 3
0.6531 Remote Similarity NPD3787 Discontinued
0.6524 Remote Similarity NPD5401 Approved
0.6519 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6519 Remote Similarity NPD4538 Approved
0.6519 Remote Similarity NPD4536 Approved
0.6519 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6517 Remote Similarity NPD7251 Discontinued
0.6517 Remote Similarity NPD3268 Approved
0.6514 Remote Similarity NPD1203 Approved
0.651 Remote Similarity NPD8455 Phase 2
0.651 Remote Similarity NPD5761 Phase 2
0.651 Remote Similarity NPD5760 Phase 2
0.6509 Remote Similarity NPD1852 Discontinued
0.65 Remote Similarity NPD1184 Approved
0.65 Remote Similarity NPD230 Phase 1
0.65 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6485 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6485 Remote Similarity NPD7808 Phase 3
0.6484 Remote Similarity NPD7033 Discontinued
0.6484 Remote Similarity NPD4308 Phase 3
0.648 Remote Similarity NPD7199 Phase 2
0.6477 Remote Similarity NPD2296 Approved
0.6474 Remote Similarity NPD1281 Approved

  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