Structure

Physi-Chem Properties

Molecular Weight:  208.02
Volume:  196.101
LogP:  0.637
LogD:  0.308
LogS:  -2.466
# Rotatable Bonds:  1
TPSA:  53.27
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.527
Synthetic Accessibility Score:  3.707
Fsp3:  0.1
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:  -4.699
MDCK Permeability:  5.421124296844937e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.882
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.044
Plasma Protein Binding (PPB):  84.71121978759766%
Volume Distribution (VD):  1.012
Pgp-substrate:  19.299274444580078%

ADMET: Metabolism

CYP1A2-inhibitor:  0.972
CYP1A2-substrate:  0.917
CYP2C19-inhibitor:  0.122
CYP2C19-substrate:  0.279
CYP2C9-inhibitor:  0.016
CYP2C9-substrate:  0.327
CYP2D6-inhibitor:  0.044
CYP2D6-substrate:  0.558
CYP3A4-inhibitor:  0.025
CYP3A4-substrate:  0.329

ADMET: Excretion

Clearance (CL):  8.821
Half-life (T1/2):  0.749

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.86
Drug-inuced Liver Injury (DILI):  0.946
AMES Toxicity:  0.873
Rat Oral Acute Toxicity:  0.423
Maximum Recommended Daily Dose:  0.244
Skin Sensitization:  0.434
Carcinogencity:  0.98
Eye Corrosion:  0.05
Eye Irritation:  0.071
Respiratory Toxicity:  0.942

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

  Natural Product: NPC470008

Natural Product ID:  NPC470008
Common Name*:   Sulfimarine
IUPAC Name:   8-methylsulfinylchromen-2-one
Synonyms:   Sulfimarine
Standard InCHIKey:  QCJKGBMZDGWKPO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H8O3S/c1-14(12)8-4-2-3-7-5-6-9(11)13-10(7)8/h2-6H,1H3
SMILES:  CS(=O)C1=CC=CC2=C1OC(=O)C=C2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1643640
PubChem CID:   53316704
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
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10479323]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12350167]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[14640527]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota Axinella verrucosa Mediterranean n.a. PMID[14738391]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15043411]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Sussex Inlet, New South Wales, Australia n.a. PMID[15104517]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15332862]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Berkeley Pit lake n.a. PMID[17970594]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. New Zealand n.a. PMID[19323568]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19326880]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20452770]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. North Sea n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Limonium tubiflorum n.a. PMID[21146414]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21916432]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22148349]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22458669]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23360521]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23477451]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23603293]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23972215]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24437979]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31433188]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[9392888]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]

☑ 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
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei MIC > 100000.0 nM PMID[505601]

☑ 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 NPC470008 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
0.8136 Intermediate Similarity NPC139891
0.7869 Intermediate Similarity NPC149545
0.784 Intermediate Similarity NPC87563
0.7717 Intermediate Similarity NPC128633
0.768 Intermediate Similarity NPC266116
0.7661 Intermediate Similarity NPC141068
0.7652 Intermediate Similarity NPC472888
0.7597 Intermediate Similarity NPC152306
0.7597 Intermediate Similarity NPC265547
0.7578 Intermediate Similarity NPC33717
0.7541 Intermediate Similarity NPC227255
0.7541 Intermediate Similarity NPC128730
0.7538 Intermediate Similarity NPC298796
0.7538 Intermediate Similarity NPC281356
0.7519 Intermediate Similarity NPC183154
0.7519 Intermediate Similarity NPC263754
0.75 Intermediate Similarity NPC107101
0.7481 Intermediate Similarity NPC14177
0.748 Intermediate Similarity NPC176971
0.7462 Intermediate Similarity NPC96705
0.7459 Intermediate Similarity NPC109637
0.7442 Intermediate Similarity NPC163398
0.7438 Intermediate Similarity NPC307425
0.7424 Intermediate Similarity NPC235190
0.7424 Intermediate Similarity NPC163200
0.7424 Intermediate Similarity NPC180006
0.7419 Intermediate Similarity NPC151530
0.7419 Intermediate Similarity NPC157473
0.7377 Intermediate Similarity NPC179686
0.7348 Intermediate Similarity NPC193193
0.7348 Intermediate Similarity NPC31314
0.7348 Intermediate Similarity NPC474874
0.7344 Intermediate Similarity NPC90903
0.7323 Intermediate Similarity NPC233238
0.7317 Intermediate Similarity NPC283546
0.7313 Intermediate Similarity NPC96286
0.7313 Intermediate Similarity NPC257188
0.7313 Intermediate Similarity NPC13007
0.7313 Intermediate Similarity NPC248429
0.7295 Intermediate Similarity NPC84325
0.7293 Intermediate Similarity NPC319378
0.7273 Intermediate Similarity NPC98748
0.7266 Intermediate Similarity NPC280760
0.7259 Intermediate Similarity NPC273772
0.7259 Intermediate Similarity NPC472518
0.7259 Intermediate Similarity NPC109675
0.7258 Intermediate Similarity NPC473393
0.7258 Intermediate Similarity NPC473855
0.7244 Intermediate Similarity NPC473809
0.7239 Intermediate Similarity NPC52247
0.7239 Intermediate Similarity NPC144418
0.7222 Intermediate Similarity NPC291837
0.7218 Intermediate Similarity NPC247553
0.7218 Intermediate Similarity NPC230951
0.7206 Intermediate Similarity NPC111347
0.7206 Intermediate Similarity NPC291899
0.7206 Intermediate Similarity NPC27671
0.7206 Intermediate Similarity NPC73413
0.7206 Intermediate Similarity NPC201667
0.72 Intermediate Similarity NPC326447
0.7177 Intermediate Similarity NPC2518
0.7165 Intermediate Similarity NPC259554
0.7164 Intermediate Similarity NPC307253
0.7164 Intermediate Similarity NPC302107
0.7164 Intermediate Similarity NPC322569
0.7163 Intermediate Similarity NPC472882
0.7153 Intermediate Similarity NPC244495
0.7153 Intermediate Similarity NPC93219
0.7132 Intermediate Similarity NPC290605
0.7132 Intermediate Similarity NPC315807
0.7132 Intermediate Similarity NPC199462
0.7132 Intermediate Similarity NPC173350
0.7132 Intermediate Similarity NPC154176
0.7121 Intermediate Similarity NPC45104
0.712 Intermediate Similarity NPC475269
0.712 Intermediate Similarity NPC288760
0.7111 Intermediate Similarity NPC187868
0.7109 Intermediate Similarity NPC25067
0.7109 Intermediate Similarity NPC88868
0.7109 Intermediate Similarity NPC231251
0.7101 Intermediate Similarity NPC188327
0.7101 Intermediate Similarity NPC234109
0.708 Intermediate Similarity NPC89630
0.7059 Intermediate Similarity NPC27198
0.7059 Intermediate Similarity NPC151237
0.7059 Intermediate Similarity NPC311219
0.705 Intermediate Similarity NPC224774
0.705 Intermediate Similarity NPC243688
0.705 Intermediate Similarity NPC121740
0.705 Intermediate Similarity NPC258567
0.7049 Intermediate Similarity NPC175298
0.7045 Intermediate Similarity NPC470860
0.7029 Intermediate Similarity NPC471828
0.7029 Intermediate Similarity NPC471827
0.7029 Intermediate Similarity NPC165556
0.7015 Intermediate Similarity NPC264976
0.7007 Intermediate Similarity NPC50720
0.7007 Intermediate Similarity NPC248786
0.7 Intermediate Similarity NPC157212
0.7 Intermediate Similarity NPC469453
0.7 Intermediate Similarity NPC185066
0.7 Intermediate Similarity NPC472519
0.7 Intermediate Similarity NPC199204
0.6992 Remote Similarity NPC217423
0.6984 Remote Similarity NPC238115
0.6978 Remote Similarity NPC471826
0.697 Remote Similarity NPC188907
0.6966 Remote Similarity NPC472881
0.6957 Remote Similarity NPC107846
0.6957 Remote Similarity NPC229113
0.695 Remote Similarity NPC474289
0.695 Remote Similarity NPC168710
0.695 Remote Similarity NPC238309
0.6947 Remote Similarity NPC303522
0.694 Remote Similarity NPC32298
0.694 Remote Similarity NPC124916
0.694 Remote Similarity NPC152159
0.6935 Remote Similarity NPC13755
0.6934 Remote Similarity NPC150214
0.6929 Remote Similarity NPC95034
0.6929 Remote Similarity NPC142087
0.6929 Remote Similarity NPC37512
0.6923 Remote Similarity NPC245552
0.6918 Remote Similarity NPC472883
0.6911 Remote Similarity NPC95755
0.6906 Remote Similarity NPC168259
0.6901 Remote Similarity NPC240722
0.6901 Remote Similarity NPC80170
0.6901 Remote Similarity NPC244799
0.6901 Remote Similarity NPC19242
0.6901 Remote Similarity NPC113098
0.6894 Remote Similarity NPC235250
0.6889 Remote Similarity NPC54243
0.6889 Remote Similarity NPC43435
0.6884 Remote Similarity NPC143725
0.6879 Remote Similarity NPC2401
0.6879 Remote Similarity NPC81261
0.6861 Remote Similarity NPC476165
0.6857 Remote Similarity NPC101894
0.6857 Remote Similarity NPC329272
0.6853 Remote Similarity NPC29734
0.6853 Remote Similarity NPC272650
0.6853 Remote Similarity NPC267336
0.685 Remote Similarity NPC127676
0.6846 Remote Similarity NPC106141
0.6842 Remote Similarity NPC296526
0.6838 Remote Similarity NPC168050
0.6831 Remote Similarity NPC27239
0.6831 Remote Similarity NPC123127
0.6815 Remote Similarity NPC293424
0.6812 Remote Similarity NPC473464
0.6812 Remote Similarity NPC476332
0.6809 Remote Similarity NPC473993
0.6809 Remote Similarity NPC161322
0.6806 Remote Similarity NPC123954
0.6806 Remote Similarity NPC175159
0.6806 Remote Similarity NPC137669
0.6806 Remote Similarity NPC14248
0.6806 Remote Similarity NPC19157
0.6806 Remote Similarity NPC194277
0.6797 Remote Similarity NPC1065
0.6786 Remote Similarity NPC202594
0.6786 Remote Similarity NPC232692
0.6786 Remote Similarity NPC88403
0.6783 Remote Similarity NPC86774
0.6783 Remote Similarity NPC2989
0.6783 Remote Similarity NPC32463
0.6783 Remote Similarity NPC327457
0.6767 Remote Similarity NPC114144
0.6765 Remote Similarity NPC37858
0.6765 Remote Similarity NPC35744
0.6759 Remote Similarity NPC318400
0.6759 Remote Similarity NPC207002
0.6759 Remote Similarity NPC471910
0.6759 Remote Similarity NPC2363
0.6759 Remote Similarity NPC7526
0.6759 Remote Similarity NPC222036
0.6759 Remote Similarity NPC36437
0.6759 Remote Similarity NPC472524
0.6759 Remote Similarity NPC233018
0.6759 Remote Similarity NPC241341
0.6759 Remote Similarity NPC133956
0.6759 Remote Similarity NPC296624
0.6759 Remote Similarity NPC469449
0.6759 Remote Similarity NPC55147
0.6759 Remote Similarity NPC31849
0.6759 Remote Similarity NPC163557
0.6759 Remote Similarity NPC167111
0.6748 Remote Similarity NPC246679
0.6744 Remote Similarity NPC194034
0.6742 Remote Similarity NPC474920
0.6741 Remote Similarity NPC471503
0.6741 Remote Similarity NPC471498
0.6738 Remote Similarity NPC163248
0.6736 Remote Similarity NPC472517
0.6716 Remote Similarity NPC51345
0.6716 Remote Similarity NPC220540
0.6715 Remote Similarity NPC470092
0.6713 Remote Similarity NPC473019
0.6712 Remote Similarity NPC309953

  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 NPC470008 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
0.8136 Intermediate Similarity NPD9697 Approved
0.7846 Intermediate Similarity NPD1244 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2862 Discontinued
0.7239 Intermediate Similarity NPD422 Phase 1
0.72 Intermediate Similarity NPD3134 Approved
0.7181 Intermediate Similarity NPD5049 Phase 3
0.7143 Intermediate Similarity NPD1358 Approved
0.7132 Intermediate Similarity NPD5535 Approved
0.7123 Intermediate Similarity NPD1652 Phase 2
0.7075 Intermediate Similarity NPD7976 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD9717 Approved
0.7055 Intermediate Similarity NPD7974 Phase 3
0.7029 Intermediate Similarity NPD3267 Approved
0.7029 Intermediate Similarity NPD3266 Approved
0.7029 Intermediate Similarity NPD2797 Approved
0.702 Intermediate Similarity NPD8012 Clinical (unspecified phase)
0.6993 Remote Similarity NPD4340 Discontinued
0.698 Remote Similarity NPD7440 Discontinued
0.6957 Remote Similarity NPD3225 Approved
0.6947 Remote Similarity NPD1241 Discontinued
0.6912 Remote Similarity NPD3496 Discontinued
0.6906 Remote Similarity NPD1203 Approved
0.6879 Remote Similarity NPD6832 Phase 2
0.6861 Remote Similarity NPD1611 Approved
0.6857 Remote Similarity NPD1019 Discontinued
0.6846 Remote Similarity NPD7835 Discontinued
0.6806 Remote Similarity NPD4307 Phase 2
0.6783 Remote Similarity NPD3268 Approved
0.6783 Remote Similarity NPD1296 Phase 2
0.6765 Remote Similarity NPD5691 Approved
0.6757 Remote Similarity NPD1803 Phase 3
0.6757 Remote Similarity NPD6800 Clinical (unspecified phase)
0.6744 Remote Similarity NPD290 Approved
0.6741 Remote Similarity NPD2347 Approved
0.6715 Remote Similarity NPD1778 Approved
0.6715 Remote Similarity NPD2107 Clinical (unspecified phase)
0.671 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2313 Discontinued
0.6644 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6642 Remote Similarity NPD5585 Approved
0.6622 Remote Similarity NPD4308 Phase 3
0.6621 Remote Similarity NPD4062 Phase 3
0.6619 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6594 Remote Similarity NPD17 Approved
0.6594 Remote Similarity NPD4626 Approved
0.6587 Remote Similarity NPD5953 Discontinued
0.6577 Remote Similarity NPD2531 Phase 2
0.6571 Remote Similarity NPD1877 Discontinued
0.6569 Remote Similarity NPD1894 Discontinued
0.6552 Remote Similarity NPD411 Approved
0.6538 Remote Similarity NPD968 Approved
0.6533 Remote Similarity NPD5085 Clinical (unspecified phase)
0.6531 Remote Similarity NPD1933 Approved
0.6531 Remote Similarity NPD447 Suspended
0.6507 Remote Similarity NPD4248 Discontinued
0.6503 Remote Similarity NPD1469 Clinical (unspecified phase)
0.65 Remote Similarity NPD6374 Clinical (unspecified phase)
0.649 Remote Similarity NPD2030 Discontinued
0.6471 Remote Similarity NPD6671 Approved
0.6454 Remote Similarity NPD1608 Approved
0.6449 Remote Similarity NPD7330 Discontinued
0.6439 Remote Similarity NPD2684 Approved
0.6423 Remote Similarity NPD9493 Approved
0.6419 Remote Similarity NPD5124 Phase 1
0.6419 Remote Similarity NPD9694 Discovery
0.6419 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6408 Remote Similarity NPD4359 Approved
0.64 Remote Similarity NPD3748 Approved
0.64 Remote Similarity NPD2799 Discontinued
0.6395 Remote Similarity NPD3058 Clinical (unspecified phase)
0.6389 Remote Similarity NPD2798 Approved
0.6383 Remote Similarity NPD1535 Discovery
0.6377 Remote Similarity NPD7644 Approved
0.637 Remote Similarity NPD5277 Phase 2
0.6364 Remote Similarity NPD1282 Approved
0.635 Remote Similarity NPD2557 Approved
0.635 Remote Similarity NPD6387 Discontinued
0.6345 Remote Similarity NPD2237 Approved
0.634 Remote Similarity NPD1243 Approved
0.6338 Remote Similarity NPD1481 Phase 2
0.6335 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6331 Remote Similarity NPD1548 Phase 1
0.6327 Remote Similarity NPD6798 Discontinued
0.6327 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6324 Remote Similarity NPD592 Approved
0.6324 Remote Similarity NPD594 Approved
0.6316 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6316 Remote Similarity NPD2346 Discontinued
0.6306 Remote Similarity NPD2236 Approved
0.6296 Remote Similarity NPD1137 Approved
0.6296 Remote Similarity NPD1139 Approved
0.6291 Remote Similarity NPD3846 Clinical (unspecified phase)
0.6272 Remote Similarity NPD7286 Phase 2
0.6259 Remote Similarity NPD5536 Phase 2
0.625 Remote Similarity NPD4179 Approved
0.625 Remote Similarity NPD3539 Phase 1
0.625 Remote Similarity NPD1551 Phase 2
0.625 Remote Similarity NPD4180 Approved
0.625 Remote Similarity NPD1138 Approved
0.625 Remote Similarity NPD7843 Approved
0.625 Remote Similarity NPD821 Approved
0.6242 Remote Similarity NPD4101 Phase 1
0.6242 Remote Similarity NPD4060 Phase 1
0.6234 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6232 Remote Similarity NPD709 Approved
0.6216 Remote Similarity NPD1048 Approved
0.6214 Remote Similarity NPD2486 Discontinued
0.6214 Remote Similarity NPD9545 Approved
0.6209 Remote Similarity NPD3540 Phase 1
0.6207 Remote Similarity NPD987 Approved
0.6202 Remote Similarity NPD1238 Approved
0.62 Remote Similarity NPD4618 Approved
0.62 Remote Similarity NPD4622 Approved
0.62 Remote Similarity NPD6355 Discontinued
0.6197 Remote Similarity NPD3847 Discontinued
0.6194 Remote Similarity NPD3750 Approved
0.619 Remote Similarity NPD682 Discontinued
0.619 Remote Similarity NPD1194 Discontinued
0.619 Remote Similarity NPD2614 Approved
0.6188 Remote Similarity NPD3111 Phase 1
0.6187 Remote Similarity NPD7636 Approved
0.6184 Remote Similarity NPD7033 Discontinued
0.6184 Remote Similarity NPD3152 Clinical (unspecified phase)
0.6183 Remote Similarity NPD9261 Approved
0.6174 Remote Similarity NPD8032 Phase 2
0.617 Remote Similarity NPD3049 Approved
0.617 Remote Similarity NPD3443 Approved
0.617 Remote Similarity NPD3444 Approved
0.617 Remote Similarity NPD3445 Approved
0.6168 Remote Similarity NPD7229 Phase 3
0.6164 Remote Similarity NPD2900 Approved
0.6164 Remote Similarity NPD2901 Approved
0.616 Remote Similarity NPD1007 Discontinued
0.6154 Remote Similarity NPD1281 Approved
0.6154 Remote Similarity NPD1091 Approved
0.6149 Remote Similarity NPD7095 Approved
0.6149 Remote Similarity NPD5163 Phase 2
0.6148 Remote Similarity NPD5451 Approved
0.6144 Remote Similarity NPD2796 Approved
0.6142 Remote Similarity NPD9260 Approved
0.6133 Remote Similarity NPD4140 Approved
0.6129 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6127 Remote Similarity NPD2554 Approved
0.6127 Remote Similarity NPD2423 Clinical (unspecified phase)
0.6127 Remote Similarity NPD2556 Approved
0.6121 Remote Similarity NPD6971 Discontinued
0.6118 Remote Similarity NPD5688 Approved
0.6118 Remote Similarity NPD5689 Approved
0.6115 Remote Similarity NPD643 Clinical (unspecified phase)
0.6115 Remote Similarity NPD6066 Clinical (unspecified phase)
0.6115 Remote Similarity NPD7157 Approved
0.6111 Remote Similarity NPD3972 Approved
0.6107 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6104 Remote Similarity NPD2353 Approved
0.6104 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6093 Remote Similarity NPD1184 Approved
0.609 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6084 Remote Similarity NPD3294 Phase 2
0.6076 Remote Similarity NPD6799 Approved
0.6071 Remote Similarity NPD3596 Phase 2
0.6071 Remote Similarity NPD5668 Clinical (unspecified phase)
0.6067 Remote Similarity NPD6233 Phase 2
0.6067 Remote Similarity NPD4870 Approved
0.6062 Remote Similarity NPD920 Approved
0.6054 Remote Similarity NPD2788 Approved
0.6042 Remote Similarity NPD1610 Phase 2
0.604 Remote Similarity NPD5746 Approved
0.6039 Remote Similarity NPD4477 Approved
0.6039 Remote Similarity NPD4476 Approved
0.6039 Remote Similarity NPD6032 Approved
0.6039 Remote Similarity NPD2935 Discontinued
0.6038 Remote Similarity NPD5401 Approved
0.6038 Remote Similarity NPD642 Clinical (unspecified phase)
0.6038 Remote Similarity NPD1578 Phase 2
0.6032 Remote Similarity NPD9365 Approved
0.6027 Remote Similarity NPD1283 Approved
0.6027 Remote Similarity NPD1876 Approved
0.6026 Remote Similarity NPD3142 Approved
0.6026 Remote Similarity NPD3140 Approved
0.6025 Remote Similarity NPD1653 Approved
0.6014 Remote Similarity NPD454 Approved
0.6014 Remote Similarity NPD769 Approved
0.6013 Remote Similarity NPD7097 Phase 1
0.6012 Remote Similarity NPD1757 Discontinued
0.6 Remote Similarity NPD9267 Approved
0.6 Remote Similarity NPD9263 Approved
0.6 Remote Similarity NPD5762 Approved
0.6 Remote Similarity NPD9264 Approved
0.6 Remote Similarity NPD5763 Approved
0.6 Remote Similarity NPD2344 Approved
0.5988 Remote Similarity NPD746 Clinical (unspecified phase)
0.5988 Remote Similarity NPD3226 Approved
0.5987 Remote Similarity NPD3367 Clinical (unspecified phase)
0.5987 Remote Similarity NPD4628 Phase 3
0.5987 Remote Similarity NPD3892 Phase 2
0.5987 Remote Similarity NPD1878 Clinical (unspecified phase)
0.5986 Remote Similarity NPD6580 Approved
0.5986 Remote Similarity NPD6581 Approved
0.5986 Remote Similarity NPD1182 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