Structure

Physi-Chem Properties

Molecular Weight:  258.05
Volume:  250.527
LogP:  2.762
LogD:  2.739
LogS:  -3.378
# Rotatable Bonds:  0
TPSA:  90.9
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.425
Synthetic Accessibility Score:  2.583
Fsp3:  0.071
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:  -5.005
MDCK Permeability:  6.337159902614076e-06
Pgp-inhibitor:  0.002
Pgp-substrate:  0.973
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.837
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.018
Plasma Protein Binding (PPB):  94.77648162841797%
Volume Distribution (VD):  0.648
Pgp-substrate:  7.861469745635986%

ADMET: Metabolism

CYP1A2-inhibitor:  0.986
CYP1A2-substrate:  0.653
CYP2C19-inhibitor:  0.154
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.558
CYP2C9-substrate:  0.948
CYP2D6-inhibitor:  0.729
CYP2D6-substrate:  0.62
CYP3A4-inhibitor:  0.506
CYP3A4-substrate:  0.075

ADMET: Excretion

Clearance (CL):  8.535
Half-life (T1/2):  0.851

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.098
Drug-inuced Liver Injury (DILI):  0.954
AMES Toxicity:  0.302
Rat Oral Acute Toxicity:  0.045
Maximum Recommended Daily Dose:  0.93
Skin Sensitization:  0.92
Carcinogencity:  0.03
Eye Corrosion:  0.448
Eye Irritation:  0.965
Respiratory Toxicity:  0.236

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

  Natural Product: NPC32470

Natural Product ID:  NPC32470
Common Name*:   Alternariol
IUPAC Name:   3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one
Synonyms:   Alternariol
Standard InCHIKey:  CEBXXEKPIIDJHL-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3
SMILES:  Cc1cc(cc2c1c1cc(cc(c1c(=O)o2)O)O)O
Synthetic Gene Cluster:   BGC0000013;
ChEMBL Identifier:   CHEMBL519982
PubChem CID:   5359485
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[18494522]
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[22276679]
NPO41350 Alternaria tenuissima + Nigrospora sphaerica Species n.a. n.a. n.a. n.a. n.a. PMID[24114180]
NPO41500 Streptomyces fradiae 007 + Penicillium sp. WC-29-5 Strain n.a. n.a. n.a. n.a. n.a. PMID[24714124]
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[25265160]
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[26841051]
NPO40417 Rhizopycnis vagum Nitaf22 Strain Morosphaeriaceae Eukaryota n.a. n.a. n.a. PMID[27441892]
NPO40268 Penicillium concentricum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[28409637]
NPO11132 Alangium longiflorum Species Cornaceae Eukaryota n.a. n.a. n.a. PMID[30106296]
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[30794407]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15125.1 Taxus wallichiana var. chinensis Varieties Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10084 Equisetum hyemale Species Equisetaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27451 Ophiocordyceps sinensis Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31311 Citrus reticulate Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27451 Ophiocordyceps sinensis Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10084 Equisetum hyemale Species Equisetaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27451 Ophiocordyceps sinensis Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3362 Dictyostelium mucoroides Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15125.1 Taxus wallichiana var. chinensis Varieties Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO563 Leucopaxillus cerealis Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10084 Equisetum hyemale Species Equisetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11132 Alangium longiflorum Species Cornaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10487 Rosa americana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10953 Papaver strigosum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22296 Rheum tataricum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11819 Trichophyton megnini Species Arthrodermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7785 Boletus fomentarius Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12272 Calceolaria petiolaris Species Calceolariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21703 Maianthemum atropurpureum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12615 Athrotaxis selaginoides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11936 Ptilocaulis walpersi Species Axinellidae 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
NPT1864 Cell Line L5178Y Mus musculus EC50 = 1.7 ug.mL-1 PMID[553389]
NPT1864 Cell Line L5178Y Mus musculus Activity = 3.7 % PMID[553389]
NPT1660 Individual Protein NUAK family SNF1-like kinase 1 Homo sapiens IC50 = 0.95 ug.mL-1 PMID[553389]
NPT1432 Individual Protein Serine/threonine-protein kinase Aurora-A Homo sapiens IC50 = 0.73 ug.mL-1 PMID[553389]
NPT1433 Individual Protein Serine/threonine-protein kinase Aurora-B Homo sapiens IC50 = 0.42 ug.mL-1 PMID[553389]
NPT1434 Individual Protein Serine/threonine-protein kinase B-raf Homo sapiens IC50 = 1.6 ug.mL-1 PMID[553389]
NPT1371 Individual Protein Cyclin-dependent kinase 2 Homo sapiens IC50 = 3.3 ug.mL-1 PMID[553389]
NPT2571 Individual Protein Mitogen-activated protein kinase kinase kinase 8 Homo sapiens IC50 = 8.0 ug.mL-1 PMID[553389]
NPT285 Individual Protein Epidermal growth factor receptor erbB1 Homo sapiens IC50 = 5.5 ug.mL-1 PMID[553389]
NPT2572 Individual Protein Ephrin type-B receptor 4 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[553389]
NPT286 Individual Protein Receptor protein-tyrosine kinase erbB-2 Homo sapiens IC50 = 9.4 ug.mL-1 PMID[553389]
NPT1436 Individual Protein Focal adhesion kinase 1 Homo sapiens IC50 = 2.4 ug.mL-1 PMID[553389]
NPT1438 Individual Protein Insulin-like growth factor I receptor Homo sapiens IC50 = 3.4 ug.mL-1 PMID[553389]
NPT36 Individual Protein Tyrosine-protein kinase SRC Homo sapiens IC50 = 4.4 ug.mL-1 PMID[553389]
NPT1478 Individual Protein Vascular endothelial growth factor receptor 2 Homo sapiens IC50 = 0.92 ug.mL-1 PMID[553389]
NPT2573 Individual Protein Vascular endothelial growth factor receptor 3 Homo sapiens IC50 = 1.3 ug.mL-1 PMID[553389]
NPT1650 Individual Protein Tyrosine-protein kinase receptor FLT3 Homo sapiens IC50 = 0.43 ug.mL-1 PMID[553389]
NPT2574 Individual Protein Insulin receptor Homo sapiens IC50 = 2.1 ug.mL-1 PMID[553389]
NPT1337 Individual Protein Hepatocyte growth factor receptor Homo sapiens IC50 = 5.4 ug.mL-1 PMID[553389]
NPT2575 Individual Protein Platelet-derived growth factor receptor beta Homo sapiens IC50 = 0.89 ug.mL-1 PMID[553389]
NPT1598 Individual Protein Casein kinase II alpha Homo sapiens IC50 = 2.0 ug.mL-1 PMID[553389]
NPT1702 Individual Protein Serine/threonine-protein kinase PLK4 Homo sapiens IC50 = 0.96 ug.mL-1 PMID[553389]
NPT2576 Individual Protein Tyrosine-protein kinase TIE-2 Homo sapiens IC50 = 7.0 ug.mL-1 PMID[553389]
NPT1433 Individual Protein Serine/threonine-protein kinase Aurora-B Homo sapiens IC50 = 1.0 ug.mL-1 PMID[553389]
NPT1438 Individual Protein Insulin-like growth factor I receptor Homo sapiens IC50 = 1.0 ug.mL-1 PMID[553389]
NPT1478 Individual Protein Vascular endothelial growth factor receptor 2 Homo sapiens IC50 = 1.0 ug.mL-1 PMID[553389]
NPT1650 Individual Protein Tyrosine-protein kinase receptor FLT3 Homo sapiens IC50 = 1.0 ug.mL-1 PMID[553389]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 50466.13 nM PMID[553391]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 20701.41 nM PMID[553391]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 14060.48 nM PMID[553391]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 34593.94 nM PMID[553391]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 30478.95 nM PMID[553391]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 16368.17 nM PMID[553391]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 16982.44 nM PMID[553391]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 18450.15 nM PMID[553391]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 40271.7 nM PMID[553391]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 36643.76 nM PMID[553391]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 40086.67 nM PMID[553391]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 23014.42 nM PMID[553391]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 7585.78 nM PMID[553391]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 20653.8 nM PMID[553391]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 28510.18 nM PMID[553391]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 69183.1 nM PMID[553391]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 43151.91 nM PMID[553391]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 23014.42 nM PMID[553391]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 20044.72 nM PMID[553391]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 3689.78 nM PMID[553391]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 44463.13 nM PMID[553391]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 58613.82 nM PMID[553391]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 16180.8 nM PMID[553391]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 13396.77 nM PMID[553391]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 26791.68 nM PMID[553391]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 27101.92 nM PMID[553391]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 59979.11 nM PMID[553391]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 27101.92 nM PMID[553391]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 65313.06 nM PMID[553391]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 16143.59 nM PMID[553391]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 37583.74 nM PMID[553391]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 16143.59 nM PMID[553391]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 27669.42 nM PMID[553391]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 12705.74 nM PMID[553391]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 18535.32 nM PMID[553391]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 18155.16 nM PMID[553391]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 27415.74 nM PMID[553391]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 17619.76 nM PMID[553391]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 6714.29 nM PMID[553391]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 34434.99 nM PMID[553391]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 59566.21 nM PMID[553391]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 18535.32 nM PMID[553391]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 13122.0 nM PMID[553391]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 24043.63 nM PMID[553391]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 20989.4 nM PMID[553391]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 26302.68 nM PMID[553391]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 19724.23 nM PMID[553391]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 23067.47 nM PMID[553391]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[553391]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 34514.37 nM PMID[553391]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 28641.78 nM PMID[553391]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 30690.22 nM PMID[553391]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 23442.29 nM PMID[553391]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 19543.39 nM PMID[553391]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 39264.49 nM PMID[553391]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[553391]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 23334.58 nM PMID[553391]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 27415.74 nM PMID[553391]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 26791.68 nM PMID[553391]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 20000.0 nM PMID[553393]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 20000.0 nM PMID[553393]
NPT65 Cell Line HepG2 Homo sapiens %max = 15.2 % PMID[553394]
NPT728 Individual Protein Serine/threonine-protein kinase AKT Homo sapiens IC50 > 10.0 ug.mL-1 PMID[553389]
NPT1560 Protein Complex Cyclin-dependent kinase 4/cyclin D1 Homo sapiens IC50 = 2.4 ug.mL-1 PMID[553389]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens IC50 = 6.9 ug.mL-1 PMID[553389]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7.0 ug.mL-1 PMID[553392]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 50.0 ug.mL-1 PMID[553392]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 11.4 ug.mL-1 PMID[553392]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 25.0 ug.mL-1 PMID[553392]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3.5 ug.mL-1 PMID[553392]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 5.5 ug.mL-1 PMID[553392]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7.9 ug.mL-1 PMID[553392]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4.9 ug.mL-1 PMID[553392]
NPT610 Others Molecular identity unknown IC50 > 200.0 ug.mL-1 PMID[553392]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[553392]

☑ 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 NPC32470 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
0.9928 High Similarity NPC267509
0.971 High Similarity NPC220106
0.965 High Similarity NPC194379
0.964 High Similarity NPC105648
0.9583 High Similarity NPC227166
0.9574 High Similarity NPC29577
0.9574 High Similarity NPC134621
0.9568 High Similarity NPC275734
0.9507 High Similarity NPC237208
0.9504 High Similarity NPC95123
0.9504 High Similarity NPC66404
0.9441 High Similarity NPC12305
0.9437 High Similarity NPC131766
0.9433 High Similarity NPC310340
0.9388 High Similarity NPC20541
0.9384 High Similarity NPC217447
0.9379 High Similarity NPC309979
0.9379 High Similarity NPC307780
0.9379 High Similarity NPC470107
0.9375 High Similarity NPC105415
0.9357 High Similarity NPC254994
0.931 High Similarity NPC6923
0.931 High Similarity NPC233267
0.931 High Similarity NPC291049
0.9247 High Similarity NPC325983
0.9247 High Similarity NPC60413
0.9225 High Similarity NPC250755
0.9184 High Similarity NPC133856
0.9172 High Similarity NPC7943
0.9172 High Similarity NPC22005
0.9172 High Similarity NPC123202
0.9161 High Similarity NPC469542
0.9143 High Similarity NPC135837
0.9137 High Similarity NPC180905
0.9137 High Similarity NPC182496
0.9122 High Similarity NPC273483
0.9116 High Similarity NPC295036
0.9116 High Similarity NPC150928
0.911 High Similarity NPC256672
0.911 High Similarity NPC27221
0.911 High Similarity NPC7025
0.9103 High Similarity NPC138978
0.9085 High Similarity NPC155205
0.9073 High Similarity NPC474373
0.9071 High Similarity NPC242712
0.9067 High Similarity NPC146211
0.9065 High Similarity NPC175943
0.9054 High Similarity NPC232645
0.9054 High Similarity NPC72958
0.9048 High Similarity NPC97028
0.9048 High Similarity NPC288036
0.9048 High Similarity NPC100985
0.9048 High Similarity NPC158338
0.9048 High Similarity NPC473978
0.9048 High Similarity NPC97029
0.9048 High Similarity NPC65589
0.9034 High Similarity NPC312789
0.9028 High Similarity NPC73028
0.9021 High Similarity NPC182421
0.9021 High Similarity NPC67650
0.9021 High Similarity NPC1704
0.9014 High Similarity NPC57380
0.9 High Similarity NPC89625
0.9 High Similarity NPC149618
0.8993 High Similarity NPC175978
0.8993 High Similarity NPC87708
0.8986 High Similarity NPC227122
0.8986 High Similarity NPC119929
0.8986 High Similarity NPC151473
0.8986 High Similarity NPC202595
0.898 High Similarity NPC37139
0.8973 High Similarity NPC473927
0.8973 High Similarity NPC154217
0.8973 High Similarity NPC225173
0.8973 High Similarity NPC163846
0.8958 High Similarity NPC94076
0.8958 High Similarity NPC182255
0.8958 High Similarity NPC469579
0.8951 High Similarity NPC316480
0.8951 High Similarity NPC165172
0.894 High Similarity NPC4547
0.8936 High Similarity NPC50455
0.8936 High Similarity NPC235115
0.8936 High Similarity NPC239495
0.8936 High Similarity NPC9985
0.8933 High Similarity NPC472799
0.8926 High Similarity NPC204350
0.8926 High Similarity NPC202157
0.8926 High Similarity NPC258249
0.8926 High Similarity NPC149526
0.8926 High Similarity NPC474417
0.8919 High Similarity NPC10027
0.8919 High Similarity NPC270160
0.8919 High Similarity NPC65775
0.8919 High Similarity NPC237440
0.8919 High Similarity NPC70764
0.8919 High Similarity NPC4423
0.8919 High Similarity NPC77325
0.8912 High Similarity NPC140120
0.8912 High Similarity NPC125801
0.8912 High Similarity NPC259632
0.8912 High Similarity NPC142863
0.8904 High Similarity NPC473692
0.8904 High Similarity NPC196137
0.8904 High Similarity NPC1886
0.8897 High Similarity NPC159855
0.8897 High Similarity NPC202981
0.8897 High Similarity NPC51106
0.8897 High Similarity NPC169479
0.8897 High Similarity NPC36181
0.8897 High Similarity NPC472006
0.8897 High Similarity NPC84266
0.8889 High Similarity NPC90411
0.8889 High Similarity NPC53649
0.8874 High Similarity NPC471800
0.8873 High Similarity NPC301915
0.8873 High Similarity NPC261292
0.8867 High Similarity NPC41326
0.8867 High Similarity NPC167903
0.8867 High Similarity NPC474843
0.8859 High Similarity NPC158866
0.8857 High Similarity NPC153783
0.8851 High Similarity NPC172329
0.8851 High Similarity NPC106328
0.8851 High Similarity NPC240622
0.8851 High Similarity NPC471641
0.8851 High Similarity NPC2569
0.8851 High Similarity NPC471642
0.8851 High Similarity NPC35150
0.8851 High Similarity NPC240253
0.8849 High Similarity NPC219892
0.8849 High Similarity NPC189823
0.8844 High Similarity NPC470322
0.8844 High Similarity NPC196114
0.8844 High Similarity NPC181388
0.8844 High Similarity NPC24136
0.8844 High Similarity NPC187282
0.8844 High Similarity NPC290133
0.8844 High Similarity NPC260946
0.8839 High Similarity NPC474350
0.8836 High Similarity NPC113770
0.8836 High Similarity NPC87609
0.8836 High Similarity NPC94794
0.8836 High Similarity NPC112791
0.8836 High Similarity NPC470296
0.8836 High Similarity NPC188632
0.8836 High Similarity NPC19896
0.8836 High Similarity NPC196459
0.8828 High Similarity NPC49108
0.8828 High Similarity NPC474385
0.8819 High Similarity NPC225153
0.8819 High Similarity NPC222342
0.8819 High Similarity NPC265871
0.8819 High Similarity NPC20709
0.8819 High Similarity NPC274784
0.8819 High Similarity NPC140890
0.8819 High Similarity NPC150648
0.8819 High Similarity NPC310135
0.8819 High Similarity NPC329203
0.8816 High Similarity NPC227062
0.8816 High Similarity NPC54928
0.8811 High Similarity NPC13768
0.8811 High Similarity NPC32441
0.8811 High Similarity NPC287246
0.8811 High Similarity NPC12296
0.8811 High Similarity NPC79943
0.8811 High Similarity NPC228661
0.8811 High Similarity NPC296490
0.8811 High Similarity NPC243083
0.8811 High Similarity NPC103001
0.8811 High Similarity NPC295261
0.8811 High Similarity NPC472602
0.8811 High Similarity NPC107586
0.8808 High Similarity NPC329844
0.8808 High Similarity NPC169990
0.8808 High Similarity NPC280530
0.8808 High Similarity NPC178964
0.8808 High Similarity NPC210942
0.8808 High Similarity NPC89474
0.8808 High Similarity NPC95842
0.88 High Similarity NPC39819
0.88 High Similarity NPC106372
0.88 High Similarity NPC209142
0.88 High Similarity NPC478148
0.88 High Similarity NPC23668
0.88 High Similarity NPC115324
0.88 High Similarity NPC193976
0.88 High Similarity NPC58668
0.88 High Similarity NPC312549
0.8794 High Similarity NPC274121
0.8794 High Similarity NPC50898
0.8794 High Similarity NPC213216
0.8794 High Similarity NPC78540
0.8792 High Similarity NPC476684
0.8784 High Similarity NPC34802
0.8782 High Similarity NPC7752
0.8776 High Similarity NPC178627
0.8776 High Similarity NPC271288
0.8776 High Similarity NPC470674
0.8776 High Similarity NPC311144

  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 NPC32470 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
0.9149 High Similarity NPD970 Clinical (unspecified phase)
0.8933 High Similarity NPD7819 Suspended
0.8882 High Similarity NPD3749 Approved
0.8811 High Similarity NPD1550 Clinical (unspecified phase)
0.8811 High Similarity NPD1552 Clinical (unspecified phase)
0.8759 High Similarity NPD3750 Approved
0.875 High Similarity NPD1549 Phase 2
0.8684 High Similarity NPD1465 Phase 2
0.8581 High Similarity NPD1511 Approved
0.8542 High Similarity NPD1510 Phase 2
0.8523 High Similarity NPD4378 Clinical (unspecified phase)
0.8521 High Similarity NPD1240 Approved
0.8497 Intermediate Similarity NPD1934 Approved
0.8471 Intermediate Similarity NPD6959 Discontinued
0.8467 Intermediate Similarity NPD1512 Approved
0.8442 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8435 Intermediate Similarity NPD1243 Approved
0.8431 Intermediate Similarity NPD7411 Suspended
0.8418 Intermediate Similarity NPD6232 Discontinued
0.8414 Intermediate Similarity NPD3748 Approved
0.8403 Intermediate Similarity NPD1607 Approved
0.84 Intermediate Similarity NPD2532 Approved
0.84 Intermediate Similarity NPD2534 Approved
0.84 Intermediate Similarity NPD2533 Approved
0.8397 Intermediate Similarity NPD7075 Discontinued
0.8356 Intermediate Similarity NPD1551 Phase 2
0.8333 Intermediate Similarity NPD7768 Phase 2
0.8323 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8301 Intermediate Similarity NPD3226 Approved
0.8286 Intermediate Similarity NPD1203 Approved
0.8278 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8272 Intermediate Similarity NPD5844 Phase 1
0.8269 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD7473 Discontinued
0.8231 Intermediate Similarity NPD2796 Approved
0.8217 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8212 Intermediate Similarity NPD6799 Approved
0.8205 Intermediate Similarity NPD2801 Approved
0.8176 Intermediate Similarity NPD2346 Discontinued
0.8163 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8153 Intermediate Similarity NPD3817 Phase 2
0.8133 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD6599 Discontinued
0.8125 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8108 Intermediate Similarity NPD6099 Approved
0.8108 Intermediate Similarity NPD6100 Approved
0.8108 Intermediate Similarity NPD2935 Discontinued
0.8071 Intermediate Similarity NPD1608 Approved
0.8071 Intermediate Similarity NPD9717 Approved
0.8067 Intermediate Similarity NPD2800 Approved
0.8052 Intermediate Similarity NPD920 Approved
0.805 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD6801 Discontinued
0.8013 Intermediate Similarity NPD4380 Phase 2
0.8 Intermediate Similarity NPD422 Phase 1
0.7987 Intermediate Similarity NPD3882 Suspended
0.7975 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD6166 Phase 2
0.7975 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7947 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD2344 Approved
0.7922 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD2799 Discontinued
0.7902 Intermediate Similarity NPD2797 Approved
0.7892 Intermediate Similarity NPD7074 Phase 3
0.7888 Intermediate Similarity NPD919 Approved
0.7877 Intermediate Similarity NPD411 Approved
0.7877 Intermediate Similarity NPD3268 Approved
0.7857 Intermediate Similarity NPD17 Approved
0.7857 Intermediate Similarity NPD7390 Discontinued
0.7853 Intermediate Similarity NPD5711 Approved
0.7853 Intermediate Similarity NPD5710 Approved
0.7838 Intermediate Similarity NPD447 Suspended
0.7831 Intermediate Similarity NPD7054 Approved
0.7812 Intermediate Similarity NPD4288 Approved
0.7808 Intermediate Similarity NPD4625 Phase 3
0.7806 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.78 Intermediate Similarity NPD4308 Phase 3
0.7798 Intermediate Similarity NPD6559 Discontinued
0.7791 Intermediate Similarity NPD4287 Approved
0.7784 Intermediate Similarity NPD7472 Approved
0.7778 Intermediate Similarity NPD4628 Phase 3
0.7778 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD3818 Discontinued
0.777 Intermediate Similarity NPD943 Approved
0.7755 Intermediate Similarity NPD3764 Approved
0.7755 Intermediate Similarity NPD2313 Discontinued
0.7751 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD5404 Approved
0.7748 Intermediate Similarity NPD5408 Approved
0.7748 Intermediate Similarity NPD5405 Approved
0.7748 Intermediate Similarity NPD5406 Approved
0.7746 Intermediate Similarity NPD1610 Phase 2
0.774 Intermediate Similarity NPD6832 Phase 2
0.7738 Intermediate Similarity NPD6797 Phase 2
0.773 Intermediate Similarity NPD5494 Approved
0.7727 Intermediate Similarity NPD2309 Approved
0.7725 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD230 Phase 1
0.7718 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD3225 Approved
0.7707 Intermediate Similarity NPD5403 Approved
0.7702 Intermediate Similarity NPD5402 Approved
0.7692 Intermediate Similarity NPD5401 Approved
0.7692 Intermediate Similarity NPD7251 Discontinued
0.7671 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD3266 Approved
0.7655 Intermediate Similarity NPD3267 Approved
0.7647 Intermediate Similarity NPD7808 Phase 3
0.7636 Intermediate Similarity NPD7229 Phase 3
0.7635 Intermediate Similarity NPD1296 Phase 2
0.7633 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD5953 Discontinued
0.7622 Intermediate Similarity NPD1201 Approved
0.7619 Intermediate Similarity NPD4908 Phase 1
0.7619 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD1283 Approved
0.7576 Intermediate Similarity NPD7199 Phase 2
0.7566 Intermediate Similarity NPD7033 Discontinued
0.755 Intermediate Similarity NPD6651 Approved
0.7534 Intermediate Similarity NPD1164 Approved
0.7534 Intermediate Similarity NPD1470 Approved
0.7533 Intermediate Similarity NPD4307 Phase 2
0.7517 Intermediate Similarity NPD4749 Approved
0.7517 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD7286 Phase 2
0.75 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD3926 Phase 2
0.7485 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1933 Approved
0.7483 Intermediate Similarity NPD2798 Approved
0.7465 Intermediate Similarity NPD9545 Approved
0.7465 Intermediate Similarity NPD1548 Phase 1
0.7456 Intermediate Similarity NPD3751 Discontinued
0.7451 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD9493 Approved
0.7442 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7003 Approved
0.7421 Intermediate Similarity NPD6273 Approved
0.7417 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD1613 Approved
0.7405 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD1281 Approved
0.7368 Intermediate Similarity NPD5124 Phase 1
0.7368 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1019 Discontinued
0.7365 Intermediate Similarity NPD1247 Approved
0.7362 Intermediate Similarity NPD37 Approved
0.7355 Intermediate Similarity NPD1471 Phase 3
0.7353 Intermediate Similarity NPD7177 Discontinued
0.7349 Intermediate Similarity NPD6234 Discontinued
0.7333 Intermediate Similarity NPD4965 Approved
0.7333 Intermediate Similarity NPD4967 Phase 2
0.7333 Intermediate Similarity NPD4966 Approved
0.7329 Intermediate Similarity NPD1481 Phase 2
0.7321 Intermediate Similarity NPD3787 Discontinued
0.7303 Intermediate Similarity NPD4060 Phase 1
0.7301 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD8313 Approved
0.7299 Intermediate Similarity NPD8312 Approved
0.7288 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD1535 Discovery
0.726 Intermediate Similarity NPD1611 Approved
0.7213 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD9269 Phase 2
0.7196 Intermediate Similarity NPD7783 Phase 2
0.7196 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD6971 Discontinued
0.7181 Intermediate Similarity NPD8151 Discontinued
0.7179 Intermediate Similarity NPD4476 Approved
0.7179 Intermediate Similarity NPD4477 Approved
0.7172 Intermediate Similarity NPD9268 Approved
0.7171 Intermediate Similarity NPD6798 Discontinued
0.7171 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD2296 Approved
0.7152 Intermediate Similarity NPD2654 Approved
0.7152 Intermediate Similarity NPD1652 Phase 2
0.7151 Intermediate Similarity NPD7228 Approved
0.7143 Intermediate Similarity NPD6355 Discontinued
0.7134 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD4360 Phase 2
0.7127 Intermediate Similarity NPD4363 Phase 3
0.7124 Intermediate Similarity NPD8032 Phase 2
0.7123 Intermediate Similarity NPD1778 Approved
0.7123 Intermediate Similarity NPD4626 Approved
0.7117 Intermediate Similarity NPD1653 Approved
0.7105 Intermediate Similarity NPD7095 Approved
0.7086 Intermediate Similarity NPD2861 Phase 2
0.7083 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD2979 Phase 3
0.7073 Intermediate Similarity NPD7458 Discontinued
0.7063 Intermediate Similarity NPD2354 Approved
0.7055 Intermediate Similarity NPD1651 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