Structure

Physi-Chem Properties

Molecular Weight:  196.05
Volume:  206.86
LogP:  3.317
LogD:  2.893
LogS:  -4.005
# Rotatable Bonds:  0
TPSA:  30.21
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.517
Synthetic Accessibility Score:  1.595
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.733
MDCK Permeability:  1.982170761039015e-05
Pgp-inhibitor:  0.166
Pgp-substrate:  0.425
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.959
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  92.23009490966797%
Volume Distribution (VD):  0.5
Pgp-substrate:  5.733322620391846%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.717
CYP2C19-inhibitor:  0.751
CYP2C19-substrate:  0.28
CYP2C9-inhibitor:  0.436
CYP2C9-substrate:  0.871
CYP2D6-inhibitor:  0.172
CYP2D6-substrate:  0.815
CYP3A4-inhibitor:  0.052
CYP3A4-substrate:  0.265

ADMET: Excretion

Clearance (CL):  1.96
Half-life (T1/2):  0.224

ADMET: Toxicity

hERG Blockers:  0.148
Human Hepatotoxicity (H-HT):  0.126
Drug-inuced Liver Injury (DILI):  0.936
AMES Toxicity:  0.768
Rat Oral Acute Toxicity:  0.222
Maximum Recommended Daily Dose:  0.068
Skin Sensitization:  0.907
Carcinogencity:  0.874
Eye Corrosion:  0.35
Eye Irritation:  0.992
Respiratory Toxicity:  0.782

Download Data

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

  Natural Product: NPC35744

Natural Product ID:  NPC35744
Common Name*:   Xanthone
IUPAC Name:   xanthen-9-one
Synonyms:   Xanthone
Standard InCHIKey:  JNELGWHKGNBSMD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
SMILES:  O=c1c2ccccc2oc2c1cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL186784
PubChem CID:   7020
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes
              • [CHEMONTID:0000204] Xanthones

*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
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. DOI[10.1078/0176-1617-00195]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[10757735]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[14735439]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. callus n.a. PMID[15715262]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[18220354]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18464091]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18558747]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota stem bark Pangradin village, Jasinga, West Java, Indonesia 2005-AUG PMID[19839614]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20817450]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. pericarp n.a. PMID[24555285]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[24717154]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[28445039]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota Roots n.a. n.a. PMID[30024167]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota fruit hulls Madras, Tamil Nadu, India 1993-MAR PMID[9213587]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4391 Hypericum perforatum Species Hypericaceae 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
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 840.0 nM PMID[565913]
NPT90 Cell Line DU-145 Homo sapiens IC50 > 500000.0 nM PMID[565915]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 500000.0 nM PMID[565915]
NPT165 Cell Line HeLa Homo sapiens IC50 > 500000.0 nM PMID[565915]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 25118.9 nM PMID[565916]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 28183.8 nM PMID[565916]
NPT1226 Individual Protein Caspase-7 Homo sapiens Potency = 25118.9 nM PMID[565916]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 22387.2 nM PMID[565916]
NPT442 Individual Protein Ferritin light chain Equus caballus Potency = 19952.6 nM PMID[565916]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 31622.8 nM PMID[565916]
NPT277 Individual Protein Caspase-1 Homo sapiens Potency = 25118.9 nM PMID[565916]
NPT501 Individual Protein Alpha-galactosidase A Homo sapiens Potency = 35481.3 nM PMID[565916]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 12589.3 nM PMID[565916]
NPT61 Individual Protein Beta-glucocerebrosidase Homo sapiens Potency n.a. 25118.9 nM PMID[565916]
NPT501 Individual Protein Alpha-galactosidase A Homo sapiens Potency n.a. 28183.8 nM PMID[565916]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 0.0 % PMID[565922]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2646 Organism Alternaria tenuis Alternaria tenuis Inhibition = -43.0 % PMID[565914]
NPT2646 Organism Alternaria tenuis Alternaria tenuis Inhibition = 5.0 % PMID[565914]
NPT2646 Organism Alternaria tenuis Alternaria tenuis Inhibition = -6.0 % PMID[565914]
NPT2646 Organism Alternaria tenuis Alternaria tenuis Inhibition = -14.0 % PMID[565914]
NPT2647 Organism Drechslera Drechslera Inhibition = 19.0 % PMID[565914]
NPT2647 Organism Drechslera Drechslera Inhibition = 29.0 % PMID[565914]
NPT2647 Organism Drechslera Drechslera Inhibition = 34.0 % PMID[565914]
NPT2647 Organism Drechslera Drechslera Inhibition = 3.0 % PMID[565914]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum Inhibition = -2.0 % PMID[565914]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum Inhibition = 8.0 % PMID[565914]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum Inhibition = 1.0 % PMID[565914]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum Inhibition = 6.0 % PMID[565914]
NPT2 Others Unspecified Potency = 25118.9 nM PMID[565916]
NPT2 Others Unspecified Potency = 12589.3 nM PMID[565916]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 12589.3 nM PMID[565916]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 28183.8 nM PMID[565916]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 16800.0 nM PMID[565917]
NPT27 Others Unspecified Ratio > 2.0 n.a. PMID[565917]
NPT27 Others Unspecified TC50 > 40.0 uM PMID[565917]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Ratio = 0.686 n.a. PMID[565918]
NPT1192 Organism Spodoptera frugiperda Spodoptera frugiperda log10LT50 = 1.731 n.a. PMID[565919]
NPT1192 Organism Spodoptera frugiperda Spodoptera frugiperda LT50 = 53.78 hr PMID[565919]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 123.71 % PMID[565920]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 131.48 % PMID[565920]
NPT2 Others Unspecified Potency n.a. 3981.1 nM PMID[565916]
NPT2 Others Unspecified Potency n.a. 2511.9 nM PMID[565916]
NPT35 Others n.a. Solubility n.a. 20000.0 nM PMID[565921]
NPT2 Others Unspecified Potency n.a. 3162.3 nM PMID[565916]
NPT617 Organism Danio rerio Danio rerio Activity = 0.0 % PMID[565922]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -5.09 % PMID[565923]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -3.812 % PMID[565924]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.15 % PMID[565925]
NPT2 Others Unspecified Inhibition = 37.03 % PMID[565926]
NPT2 Others Unspecified Inhibition = 12.31 % PMID[565926]
NPT741 Individual Protein Tyrosinase Homo sapiens IC50 = 8840.0 nM PMID[565926]
NPT741 Individual Protein Tyrosinase Homo sapiens Inhibition = 84.9 % PMID[565926]
NPT22125 SINGLE PROTEIN Phosphoglycerate mutase 1 Homo sapiens IC50 = 500.0 nM PMID[565927]
NPT2 Others Unspecified Potency n.a. 48557.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34665.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1096.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15355.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 49 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21689.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 17373.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48966.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6113.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 769.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19331.2 nM PubChem BioAssay data set

☑ 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 NPC35744 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
0.9737 High Similarity NPC314329
0.9732 High Similarity NPC32298
0.9646 High Similarity NPC54243
0.9304 High Similarity NPC201284
0.9237 High Similarity NPC93730
0.916 High Similarity NPC193805
0.9083 High Similarity NPC2771
0.9024 High Similarity NPC278787
0.9016 High Similarity NPC125887
0.8952 High Similarity NPC141549
0.8947 High Similarity NPC279916
0.8934 High Similarity NPC298884
0.8934 High Similarity NPC22783
0.8926 High Similarity NPC224657
0.8898 High Similarity NPC246214
0.8871 High Similarity NPC228184
0.8862 High Similarity NPC196034
0.8852 High Similarity NPC237868
0.8843 High Similarity NPC107846
0.881 High Similarity NPC287533
0.88 High Similarity NPC301717
0.878 High Similarity NPC41721
0.876 High Similarity NPC472888
0.8729 High Similarity NPC171023
0.872 High Similarity NPC7569
0.8699 High Similarity NPC474264
0.8689 High Similarity NPC56332
0.864 High Similarity NPC197425
0.864 High Similarity NPC473019
0.8621 High Similarity NPC53953
0.8605 High Similarity NPC9985
0.8605 High Similarity NPC239495
0.8594 High Similarity NPC292998
0.8583 High Similarity NPC284424
0.8583 High Similarity NPC470092
0.8583 High Similarity NPC230951
0.8571 High Similarity NPC115998
0.8571 High Similarity NPC39753
0.8527 High Similarity NPC125269
0.8504 High Similarity NPC137264
0.8504 High Similarity NPC11173
0.8487 Intermediate Similarity NPC217423
0.8487 Intermediate Similarity NPC45104
0.8487 Intermediate Similarity NPC469954
0.8475 Intermediate Similarity NPC188907
0.8473 Intermediate Similarity NPC84585
0.8473 Intermediate Similarity NPC476480
0.8462 Intermediate Similarity NPC99854
0.845 Intermediate Similarity NPC57601
0.8438 Intermediate Similarity NPC113006
0.8438 Intermediate Similarity NPC278556
0.8417 Intermediate Similarity NPC152159
0.8417 Intermediate Similarity NPC206007
0.8409 Intermediate Similarity NPC472460
0.8409 Intermediate Similarity NPC329225
0.8409 Intermediate Similarity NPC18457
0.8409 Intermediate Similarity NPC147686
0.8403 Intermediate Similarity NPC316062
0.8397 Intermediate Similarity NPC254741
0.8385 Intermediate Similarity NPC172262
0.8374 Intermediate Similarity NPC311219
0.8372 Intermediate Similarity NPC128216
0.8372 Intermediate Similarity NPC473655
0.8372 Intermediate Similarity NPC101294
0.8346 Intermediate Similarity NPC57552
0.8346 Intermediate Similarity NPC11566
0.8346 Intermediate Similarity NPC261234
0.8333 Intermediate Similarity NPC79943
0.8333 Intermediate Similarity NPC290291
0.8333 Intermediate Similarity NPC275055
0.8333 Intermediate Similarity NPC295261
0.8333 Intermediate Similarity NPC12296
0.8333 Intermediate Similarity NPC259685
0.8333 Intermediate Similarity NPC107586
0.8333 Intermediate Similarity NPC228661
0.8333 Intermediate Similarity NPC243083
0.8333 Intermediate Similarity NPC32441
0.8333 Intermediate Similarity NPC296490
0.8333 Intermediate Similarity NPC287246
0.8333 Intermediate Similarity NPC103001
0.8333 Intermediate Similarity NPC157855
0.8333 Intermediate Similarity NPC13768
0.8321 Intermediate Similarity NPC77955
0.832 Intermediate Similarity NPC4164
0.8308 Intermediate Similarity NPC50898
0.8308 Intermediate Similarity NPC213216
0.8308 Intermediate Similarity NPC274121
0.8308 Intermediate Similarity NPC78540
0.8306 Intermediate Similarity NPC182646
0.8306 Intermediate Similarity NPC11799
0.8306 Intermediate Similarity NPC141252
0.8295 Intermediate Similarity NPC118253
0.8295 Intermediate Similarity NPC474340
0.8291 Intermediate Similarity NPC233238
0.8291 Intermediate Similarity NPC23332
0.8284 Intermediate Similarity NPC472409
0.8284 Intermediate Similarity NPC171094
0.8284 Intermediate Similarity NPC145673
0.8284 Intermediate Similarity NPC69769
0.8279 Intermediate Similarity NPC168050
0.8271 Intermediate Similarity NPC188947
0.8271 Intermediate Similarity NPC280284
0.8271 Intermediate Similarity NPC118813
0.8271 Intermediate Similarity NPC99333
0.8268 Intermediate Similarity NPC475017
0.8258 Intermediate Similarity NPC161196
0.825 Intermediate Similarity NPC470860
0.8244 Intermediate Similarity NPC248872
0.8244 Intermediate Similarity NPC66705
0.8231 Intermediate Similarity NPC229646
0.8231 Intermediate Similarity NPC182428
0.8222 Intermediate Similarity NPC3188
0.8217 Intermediate Similarity NPC324488
0.8209 Intermediate Similarity NPC265871
0.8209 Intermediate Similarity NPC310135
0.8209 Intermediate Similarity NPC329203
0.8209 Intermediate Similarity NPC225153
0.8209 Intermediate Similarity NPC274784
0.8209 Intermediate Similarity NPC136095
0.8209 Intermediate Similarity NPC20709
0.8209 Intermediate Similarity NPC222342
0.8209 Intermediate Similarity NPC316480
0.8209 Intermediate Similarity NPC150648
0.8205 Intermediate Similarity NPC183648
0.8203 Intermediate Similarity NPC211120
0.8203 Intermediate Similarity NPC187907
0.8195 Intermediate Similarity NPC250266
0.8195 Intermediate Similarity NPC266597
0.8195 Intermediate Similarity NPC299379
0.8189 Intermediate Similarity NPC49852
0.8189 Intermediate Similarity NPC475496
0.8175 Intermediate Similarity NPC470858
0.8168 Intermediate Similarity NPC1249
0.8168 Intermediate Similarity NPC223354
0.8162 Intermediate Similarity NPC144499
0.8162 Intermediate Similarity NPC169479
0.8162 Intermediate Similarity NPC202981
0.8162 Intermediate Similarity NPC147145
0.8162 Intermediate Similarity NPC159855
0.8154 Intermediate Similarity NPC313618
0.8154 Intermediate Similarity NPC472882
0.8148 Intermediate Similarity NPC129853
0.8148 Intermediate Similarity NPC188243
0.8148 Intermediate Similarity NPC305355
0.8148 Intermediate Similarity NPC172986
0.8148 Intermediate Similarity NPC270883
0.8148 Intermediate Similarity NPC284550
0.8148 Intermediate Similarity NPC261227
0.8148 Intermediate Similarity NPC6407
0.8148 Intermediate Similarity NPC475680
0.8148 Intermediate Similarity NPC110228
0.8148 Intermediate Similarity NPC76445
0.8148 Intermediate Similarity NPC235239
0.8134 Intermediate Similarity NPC201395
0.8134 Intermediate Similarity NPC124269
0.8134 Intermediate Similarity NPC17848
0.813 Intermediate Similarity NPC233282
0.8125 Intermediate Similarity NPC473907
0.812 Intermediate Similarity NPC240593
0.812 Intermediate Similarity NPC281917
0.812 Intermediate Similarity NPC13408
0.812 Intermediate Similarity NPC187432
0.812 Intermediate Similarity NPC61546
0.812 Intermediate Similarity NPC72452
0.812 Intermediate Similarity NPC473887
0.812 Intermediate Similarity NPC234133
0.812 Intermediate Similarity NPC127447
0.812 Intermediate Similarity NPC231772
0.812 Intermediate Similarity NPC194281
0.812 Intermediate Similarity NPC216361
0.812 Intermediate Similarity NPC29353
0.812 Intermediate Similarity NPC124784
0.812 Intermediate Similarity NPC47815
0.812 Intermediate Similarity NPC116775
0.812 Intermediate Similarity NPC256042
0.8103 Intermediate Similarity NPC141523
0.8102 Intermediate Similarity NPC149026
0.8102 Intermediate Similarity NPC38219
0.8102 Intermediate Similarity NPC91560
0.8102 Intermediate Similarity NPC59551
0.8102 Intermediate Similarity NPC18585
0.8102 Intermediate Similarity NPC75049
0.8102 Intermediate Similarity NPC164980
0.8102 Intermediate Similarity NPC39329
0.8102 Intermediate Similarity NPC169591
0.8102 Intermediate Similarity NPC68104
0.8102 Intermediate Similarity NPC166138
0.8102 Intermediate Similarity NPC221432
0.8102 Intermediate Similarity NPC257097
0.8102 Intermediate Similarity NPC59522
0.8102 Intermediate Similarity NPC106985
0.8102 Intermediate Similarity NPC150408
0.8102 Intermediate Similarity NPC175504
0.8102 Intermediate Similarity NPC310130
0.8102 Intermediate Similarity NPC143896
0.8095 Intermediate Similarity NPC89630
0.8088 Intermediate Similarity NPC103362
0.8088 Intermediate Similarity NPC205006
0.8088 Intermediate Similarity NPC156590
0.8088 Intermediate Similarity NPC147688

  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 NPC35744 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
0.9737 High Similarity NPD1547 Clinical (unspecified phase)
0.872 High Similarity NPD2313 Discontinued
0.8699 High Similarity NPD2798 Approved
0.8618 High Similarity NPD1203 Approved
0.856 High Similarity NPD6832 Phase 2
0.8462 Intermediate Similarity NPD1241 Discontinued
0.8409 Intermediate Similarity NPD1549 Phase 2
0.8397 Intermediate Similarity NPD2796 Approved
0.8374 Intermediate Similarity NPD9717 Approved
0.8372 Intermediate Similarity NPD1933 Approved
0.8333 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD2346 Discontinued
0.8333 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8321 Intermediate Similarity NPD2799 Discontinued
0.8195 Intermediate Similarity NPD2344 Approved
0.8175 Intermediate Similarity NPD3266 Approved
0.8175 Intermediate Similarity NPD3267 Approved
0.8154 Intermediate Similarity NPD4307 Phase 2
0.8154 Intermediate Similarity NPD1240 Approved
0.811 Intermediate Similarity NPD1019 Discontinued
0.8092 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.808 Intermediate Similarity NPD3972 Approved
0.8045 Intermediate Similarity NPD3748 Approved
0.8045 Intermediate Similarity NPD1510 Phase 2
0.8031 Intermediate Similarity NPD2797 Approved
0.803 Intermediate Similarity NPD1607 Approved
0.7956 Intermediate Similarity NPD2309 Approved
0.7953 Intermediate Similarity NPD1876 Approved
0.7931 Intermediate Similarity NPD9697 Approved
0.7926 Intermediate Similarity NPD1471 Phase 3
0.791 Intermediate Similarity NPD4308 Phase 3
0.7863 Intermediate Similarity NPD3268 Approved
0.7852 Intermediate Similarity NPD1551 Phase 2
0.784 Intermediate Similarity NPD17 Approved
0.7826 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.781 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.781 Intermediate Similarity NPD1243 Approved
0.7805 Intermediate Similarity NPD9493 Approved
0.7786 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD4662 Approved
0.7786 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD5401 Approved
0.7786 Intermediate Similarity NPD4661 Approved
0.7759 Intermediate Similarity NPD9261 Approved
0.7754 Intermediate Similarity NPD3750 Approved
0.7727 Intermediate Similarity NPD411 Approved
0.7721 Intermediate Similarity NPD2935 Discontinued
0.7717 Intermediate Similarity NPD1201 Approved
0.7714 Intermediate Similarity NPD1511 Approved
0.7714 Intermediate Similarity NPD6799 Approved
0.7708 Intermediate Similarity NPD7411 Suspended
0.7692 Intermediate Similarity NPD3226 Approved
0.7687 Intermediate Similarity NPD447 Suspended
0.7676 Intermediate Similarity NPD5403 Approved
0.7664 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD1608 Approved
0.7643 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD6585 Discontinued
0.7623 Intermediate Similarity NPD5535 Approved
0.7615 Intermediate Similarity NPD1470 Approved
0.7612 Intermediate Similarity NPD3140 Approved
0.7612 Intermediate Similarity NPD3142 Approved
0.7606 Intermediate Similarity NPD1512 Approved
0.7603 Intermediate Similarity NPD7819 Suspended
0.7603 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD5890 Approved
0.7586 Intermediate Similarity NPD5889 Approved
0.7556 Intermediate Similarity NPD4618 Approved
0.7556 Intermediate Similarity NPD4622 Approved
0.7541 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD1894 Discontinued
0.7538 Intermediate Similarity NPD3225 Approved
0.7536 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD2353 Approved
0.7535 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD6844 Discontinued
0.7534 Intermediate Similarity NPD1934 Approved
0.752 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD1481 Phase 2
0.7517 Intermediate Similarity NPD4380 Phase 2
0.7517 Intermediate Similarity NPD6599 Discontinued
0.75 Intermediate Similarity NPD9263 Approved
0.75 Intermediate Similarity NPD9264 Approved
0.75 Intermediate Similarity NPD9267 Approved
0.75 Intermediate Similarity NPD1238 Approved
0.7483 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD1651 Approved
0.7463 Intermediate Similarity NPD6798 Discontinued
0.745 Intermediate Similarity NPD7075 Discontinued
0.745 Intermediate Similarity NPD3749 Approved
0.745 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD5688 Approved
0.7445 Intermediate Similarity NPD5689 Approved
0.7442 Intermediate Similarity NPD1535 Discovery
0.7438 Intermediate Similarity NPD9266 Approved
0.7438 Intermediate Similarity NPD74 Approved
0.7432 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD920 Approved
0.7415 Intermediate Similarity NPD6279 Approved
0.7415 Intermediate Similarity NPD6801 Discontinued
0.7415 Intermediate Similarity NPD6280 Approved
0.7351 Intermediate Similarity NPD5494 Approved
0.7348 Intermediate Similarity NPD1164 Approved
0.7333 Intermediate Similarity NPD1296 Phase 2
0.7329 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD3887 Approved
0.7324 Intermediate Similarity NPD2354 Approved
0.7315 Intermediate Similarity NPD2296 Approved
0.7315 Intermediate Similarity NPD5402 Approved
0.7308 Intermediate Similarity NPD1281 Approved
0.7273 Intermediate Similarity NPD968 Approved
0.7267 Intermediate Similarity NPD7768 Phase 2
0.7266 Intermediate Similarity NPD7033 Discontinued
0.7254 Intermediate Similarity NPD7003 Approved
0.7254 Intermediate Similarity NPD4628 Phase 3
0.7254 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2801 Approved
0.7241 Intermediate Similarity NPD5049 Phase 3
0.7234 Intermediate Similarity NPD2897 Discontinued
0.7209 Intermediate Similarity NPD5585 Approved
0.7206 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD3764 Approved
0.72 Intermediate Similarity NPD3817 Phase 2
0.7188 Intermediate Similarity NPD5536 Phase 2
0.7176 Intermediate Similarity NPD1610 Phase 2
0.7176 Intermediate Similarity NPD1611 Approved
0.7174 Intermediate Similarity NPD6355 Discontinued
0.7174 Intermediate Similarity NPD1184 Approved
0.7165 Intermediate Similarity NPD6671 Approved
0.7165 Intermediate Similarity NPD2557 Approved
0.7161 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD7440 Discontinued
0.7153 Intermediate Similarity NPD8032 Phase 2
0.7152 Intermediate Similarity NPD3882 Suspended
0.7143 Intermediate Similarity NPD1283 Approved
0.7132 Intermediate Similarity NPD1548 Phase 1
0.7132 Intermediate Similarity NPD9545 Approved
0.7131 Intermediate Similarity NPD3134 Approved
0.7123 Intermediate Similarity NPD6273 Approved
0.7114 Intermediate Similarity NPD2366 Approved
0.7113 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD1237 Approved
0.7101 Intermediate Similarity NPD943 Approved
0.7097 Intermediate Similarity NPD5451 Approved
0.7092 Intermediate Similarity NPD6100 Approved
0.7092 Intermediate Similarity NPD4476 Approved
0.7092 Intermediate Similarity NPD6099 Approved
0.7092 Intermediate Similarity NPD4477 Approved
0.7087 Intermediate Similarity NPD9281 Approved
0.7086 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD3873 Phase 3
0.7075 Intermediate Similarity NPD3869 Phase 3
0.7075 Intermediate Similarity NPD5586 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1358 Approved
0.7073 Intermediate Similarity NPD290 Approved
0.7069 Intermediate Similarity NPD1202 Approved
0.7067 Intermediate Similarity NPD7577 Discontinued
0.7063 Intermediate Similarity NPD2800 Approved
0.7059 Intermediate Similarity NPD919 Approved
0.7051 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD6166 Phase 2
0.7051 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD422 Phase 1
0.7034 Intermediate Similarity NPD160 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD6808 Phase 2
0.7029 Intermediate Similarity NPD6233 Phase 2
0.7023 Intermediate Similarity NPD1778 Approved
0.7016 Intermediate Similarity NPD2684 Approved
0.7014 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.6987 Remote Similarity NPD3926 Phase 2
0.698 Remote Similarity NPD2651 Approved
0.698 Remote Similarity NPD7458 Discontinued
0.698 Remote Similarity NPD2649 Approved
0.6974 Remote Similarity NPD4288 Approved
0.697 Remote Similarity NPD3847 Discontinued
0.697 Remote Similarity NPD3496 Discontinued
0.6968 Remote Similarity NPD1247 Approved
0.6968 Remote Similarity NPD6959 Discontinued
0.6962 Remote Similarity NPD3818 Discontinued
0.6954 Remote Similarity NPD7317 Phase 3
0.6948 Remote Similarity NPD3252 Approved
0.6947 Remote Similarity NPD3443 Approved
0.6947 Remote Similarity NPD3445 Approved
0.6947 Remote Similarity NPD3444 Approved
0.6947 Remote Similarity NPD3049 Approved
0.6947 Remote Similarity NPD5691 Approved
0.6944 Remote Similarity NPD2654 Approved
0.6943 Remote Similarity NPD7784 Clinical (unspecified phase)
0.694 Remote Similarity NPD4359 Approved
0.6939 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6934 Remote Similarity NPD2614 Approved
0.6928 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6906 Remote Similarity NPD4062 Phase 3
0.6906 Remote Similarity NPD520 Approved
0.6905 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6901 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6894 Remote Similarity NPD6559 Discontinued
0.6894 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6894 Remote Similarity NPD6516 Phase 2

  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