Structure

Physi-Chem Properties

Molecular Weight:  262.17
Volume:  268.071
LogP:  0.608
LogD:  1.412
LogS:  -1.122
# Rotatable Bonds:  0
TPSA:  43.78
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.696
Synthetic Accessibility Score:  4.477
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.876
MDCK Permeability:  1.004311070573749e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.939
Human Intestinal Absorption (HIA):  0.058
20% Bioavailability (F20%):  0.915
30% Bioavailability (F30%):  0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.264
Plasma Protein Binding (PPB):  29.940521240234375%
Volume Distribution (VD):  1.51
Pgp-substrate:  64.7577133178711%

ADMET: Metabolism

CYP1A2-inhibitor:  0.037
CYP1A2-substrate:  0.097
CYP2C19-inhibitor:  0.034
CYP2C19-substrate:  0.834
CYP2C9-inhibitor:  0.015
CYP2C9-substrate:  0.084
CYP2D6-inhibitor:  0.035
CYP2D6-substrate:  0.569
CYP3A4-inhibitor:  0.011
CYP3A4-substrate:  0.412

ADMET: Excretion

Clearance (CL):  4.684
Half-life (T1/2):  0.819

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.663
Drug-inuced Liver Injury (DILI):  0.254
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.284
Maximum Recommended Daily Dose:  0.363
Skin Sensitization:  0.94
Carcinogencity:  0.746
Eye Corrosion:  0.679
Eye Irritation:  0.661
Respiratory Toxicity:  0.952

Download Data

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  Natural Product: NPC91036

Natural Product ID:  NPC91036
Common Name*:   HAPHBHKQJIPUEP-WHPHWUKISA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  HAPHBHKQJIPUEP-WHPHWUKISA-N
Standard InCHI:  InChI=1S/C15H22N2O2/c18-11-7-12-13-4-1-5-14(19)17(13)8-10-3-2-6-16(9-11)15(10)12/h1,5,10-13,15,18H,2-4,6-9H2/p+1/t10-,11-,12+,13+,15-/m0/s1
SMILES:  C1=CC(=O)N2C[C@@H]3CCC[NH+]4C[C@H](C[C@H]([C@H]2C1)[C@H]34)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL382625
PubChem CID:   12133310
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002719] Lupin alkaloids
        • [CHEMONTID:0002720] Matrine alkaloids

*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
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[11054840]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota twigs n.a. n.a. PMID[1453182]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. leaf n.a. PMID[15165152]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota leaves n.a. n.a. PMID[15165152]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. PMID[15911254]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18348535]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[19407970]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. bark n.a. PMID[21553897]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO7715 Sophora tonkinensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24345512]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[24459770]
NPO7715 Sophora tonkinensis Species Fabaceae Eukaryota root n.a. n.a. PMID[24959987]
NPO7715 Sophora tonkinensis Species Fabaceae Eukaryota Rhizomes Nanning, Guangxi Province, China 2012-Dec PMID[26132528]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO7715 Sophora tonkinensis Species Fabaceae Eukaryota Roots; Rhizomes n.a. n.a. PMID[30698432]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7715 Sophora tonkinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30647 Sophora vicllfolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[Title]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7715 Sophora tonkinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20084 Atraphaxis spinosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18143 Dendronephthya griffini Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20421 Aplophyllum alberti-regelii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO19912 Vellozia nanuzae Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16569 Gymnocalycium schickendantzii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19995 Baccharis neglecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11523 Erysimum leptophyllum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17849 Centaurea maculosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22937 Vernonia fagifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28072 Theonella conica Species Theonellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4051 Tricholoma columbetta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7715 Sophora tonkinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12313 Haplophyllum obtusifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21243 Siphonaria capensis Species Siphonariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21562 Diospyros assimilis Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13449 Syzygium polycephaloides Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21108 Eria anomala Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14241 Planchonia grandis Species Asterolecaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16141 Piper regnellii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9968 Shigella dysenteriae Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18866 Pteridium esculentum Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17560 Pancratium sickenbergeri Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21495 Abelia chinensis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19810 Myxococcus stipitatus Species Myxococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19511 Dolabella californica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17258 Rhinella marina Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27367 Latrunculia magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18473 Plathymenia reticulata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20843 Monsonia senegalensis Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5903 Conus mus Species Conidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22961 Cordia leucocephala Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21631 Faramea salicifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19036 Esenbeckia leiocarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21038 Lemaireocereus longispinus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28202 Helichrysum tenuifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20624 Simarouba glauca Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

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

  NP Quantity Composition/Concentration

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

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

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens Activity >= 25.0 % PMID[549716]
NPT189 Cell Line Vero Chlorocebus aethiops TC50 > 762.34 uM PMID[549717]
NPT91 Cell Line KB Homo sapiens IC50 > 40000.0 nM PMID[549718]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 40000.0 nM PMID[549718]
NPT81 Cell Line A549 Homo sapiens IC50 > 40000.0 nM PMID[549718]
NPT963 Organism Hepatitis B virus Hepatitis B virus Activity = 24.5 % PMID[549716]
NPT963 Organism Hepatitis B virus Hepatitis B virus Activity = 0.0 % PMID[549716]
NPT963 Organism Hepatitis B virus Hepatitis B virus Activity = 5.7 % PMID[549716]
NPT3119 Organism Human coxsackievirus B3 Human coxsackievirus B3 IC50 = 197220.0 nM PMID[549717]
NPT2 Others Unspecified Selectivity Index > 3.9 n.a. PMID[549717]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 40000.0 nM PMID[549718]

☑ 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 NPC91036 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
0.9677 High Similarity NPC144714
0.9677 High Similarity NPC100810
0.9278 High Similarity NPC472856
0.9231 High Similarity NPC145707
0.8111 Intermediate Similarity NPC120699
0.8111 Intermediate Similarity NPC127430
0.7872 Intermediate Similarity NPC207048
0.7692 Intermediate Similarity NPC308050
0.7684 Intermediate Similarity NPC143344
0.7684 Intermediate Similarity NPC78058
0.7684 Intermediate Similarity NPC135639
0.7684 Intermediate Similarity NPC234822
0.7684 Intermediate Similarity NPC61321
0.7447 Intermediate Similarity NPC209232
0.7282 Intermediate Similarity NPC25033
0.7282 Intermediate Similarity NPC476261
0.7282 Intermediate Similarity NPC470382
0.7282 Intermediate Similarity NPC471635
0.7282 Intermediate Similarity NPC119225
0.7273 Intermediate Similarity NPC168017
0.7129 Intermediate Similarity NPC178632
0.6915 Remote Similarity NPC34672
0.6804 Remote Similarity NPC268580
0.6771 Remote Similarity NPC244256
0.6771 Remote Similarity NPC86452
0.6737 Remote Similarity NPC63284
0.67 Remote Similarity NPC124359
0.6667 Remote Similarity NPC214125
0.6667 Remote Similarity NPC320667
0.646 Remote Similarity NPC477000
0.646 Remote Similarity NPC477001
0.64 Remote Similarity NPC476560
0.6372 Remote Similarity NPC473254
0.6364 Remote Similarity NPC473695
0.6364 Remote Similarity NPC473446
0.6311 Remote Similarity NPC475975
0.63 Remote Similarity NPC132858
0.63 Remote Similarity NPC267203
0.63 Remote Similarity NPC77890
0.6286 Remote Similarity NPC324506
0.6283 Remote Similarity NPC473289
0.6277 Remote Similarity NPC23721
0.6275 Remote Similarity NPC255430
0.622 Remote Similarity NPC247902
0.622 Remote Similarity NPC262880
0.6195 Remote Similarity NPC77703
0.6167 Remote Similarity NPC478137
0.6161 Remote Similarity NPC270813
0.6154 Remote Similarity NPC476276
0.6154 Remote Similarity NPC207820
0.6139 Remote Similarity NPC90839
0.6126 Remote Similarity NPC289140
0.6122 Remote Similarity NPC470992
0.6122 Remote Similarity NPC470993
0.6111 Remote Similarity NPC17143
0.6111 Remote Similarity NPC47230
0.6106 Remote Similarity NPC316730
0.6102 Remote Similarity NPC274895
0.6066 Remote Similarity NPC288629
0.6034 Remote Similarity NPC75523
0.6034 Remote Similarity NPC475239
0.6017 Remote Similarity NPC159367
0.6 Remote Similarity NPC116881
0.6 Remote Similarity NPC57163
0.6 Remote Similarity NPC13351
0.5984 Remote Similarity NPC474984
0.5983 Remote Similarity NPC476328
0.5981 Remote Similarity NPC473525
0.5968 Remote Similarity NPC474006
0.595 Remote Similarity NPC474995
0.5948 Remote Similarity NPC476877
0.5948 Remote Similarity NPC318544
0.5897 Remote Similarity NPC470596
0.5897 Remote Similarity NPC133420
0.5897 Remote Similarity NPC470073
0.5888 Remote Similarity NPC322672
0.5877 Remote Similarity NPC91604
0.5865 Remote Similarity NPC45906
0.5865 Remote Similarity NPC31313
0.5865 Remote Similarity NPC149908
0.5865 Remote Similarity NPC288415
0.5862 Remote Similarity NPC176012
0.5859 Remote Similarity NPC26932
0.5857 Remote Similarity NPC276822
0.5856 Remote Similarity NPC93027
0.5847 Remote Similarity NPC476876
0.5841 Remote Similarity NPC476903
0.5833 Remote Similarity NPC473578
0.5827 Remote Similarity NPC315188
0.5826 Remote Similarity NPC477964
0.5816 Remote Similarity NPC97614
0.5812 Remote Similarity NPC241879
0.581 Remote Similarity NPC93630
0.58 Remote Similarity NPC470994
0.5798 Remote Similarity NPC176773
0.5798 Remote Similarity NPC46981
0.5794 Remote Similarity NPC319913
0.5789 Remote Similarity NPC474164
0.5763 Remote Similarity NPC212874
0.575 Remote Similarity NPC470595
0.5738 Remote Similarity NPC143173
0.5736 Remote Similarity NPC314192
0.5728 Remote Similarity NPC473971
0.5728 Remote Similarity NPC475363
0.5728 Remote Similarity NPC473972
0.5726 Remote Similarity NPC247060
0.5726 Remote Similarity NPC50815
0.5726 Remote Similarity NPC272166
0.5714 Remote Similarity NPC41162
0.5714 Remote Similarity NPC81006
0.5714 Remote Similarity NPC471109
0.5714 Remote Similarity NPC277341
0.5714 Remote Similarity NPC226982
0.5704 Remote Similarity NPC313348
0.5704 Remote Similarity NPC475987
0.5699 Remote Similarity NPC112398
0.5691 Remote Similarity NPC469865
0.569 Remote Similarity NPC135799
0.5684 Remote Similarity NPC206660
0.5676 Remote Similarity NPC53240
0.5662 Remote Similarity NPC99864
0.566 Remote Similarity NPC473810
0.5656 Remote Similarity NPC63511
0.5652 Remote Similarity NPC475646
0.5652 Remote Similarity NPC140300
0.5648 Remote Similarity NPC76283
0.5645 Remote Similarity NPC469597
0.5638 Remote Similarity NPC477459
0.5638 Remote Similarity NPC477461
0.563 Remote Similarity NPC476921
0.5625 Remote Similarity NPC110875
0.5625 Remote Similarity NPC477143
0.5625 Remote Similarity NPC477140
0.5625 Remote Similarity NPC118844
0.5625 Remote Similarity NPC72183
0.5625 Remote Similarity NPC299808
0.561 Remote Similarity NPC476875
0.561 Remote Similarity NPC474431
0.561 Remote Similarity NPC474411
0.5606 Remote Similarity NPC96010
0.5606 Remote Similarity NPC317654
0.56 Remote Similarity NPC322372
0.56 Remote Similarity NPC327517
0.56 Remote Similarity NPC321485
0.56 Remote Similarity NPC319334
0.56 Remote Similarity NPC317377
0.56 Remote Similarity NPC145501

  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 NPC91036 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
0.63 Remote Similarity NPD529 Approved
0.5982 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5847 Remote Similarity NPD7333 Discontinued
0.5772 Remote Similarity NPD1376 Discontinued
0.5736 Remote Similarity NPD5576 Approved
0.5736 Remote Similarity NPD5579 Approved
0.5726 Remote Similarity NPD1000 Clinical (unspecified phase)
0.5669 Remote Similarity NPD7522 Discontinued
0.5662 Remote Similarity NPD8415 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