Structure

Physi-Chem Properties

Molecular Weight:  318.22
Volume:  353.188
LogP:  4.427
LogD:  2.947
LogS:  -4.051
# Rotatable Bonds:  5
TPSA:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.451
Synthetic Accessibility Score:  4.257
Fsp3:  0.7
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.036
MDCK Permeability:  2.798456080199685e-05
Pgp-inhibitor:  0.009
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.133
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  68.86865997314453%
Volume Distribution (VD):  0.304
Pgp-substrate:  23.208066940307617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.164
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.459
CYP2C9-inhibitor:  0.095
CYP2C9-substrate:  0.938
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.553
CYP3A4-inhibitor:  0.055
CYP3A4-substrate:  0.178

ADMET: Excretion

Clearance (CL):  3.841
Half-life (T1/2):  0.71

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.352
Drug-inuced Liver Injury (DILI):  0.09
AMES Toxicity:  0.041
Rat Oral Acute Toxicity:  0.749
Maximum Recommended Daily Dose:  0.854
Skin Sensitization:  0.918
Carcinogencity:  0.843
Eye Corrosion:  0.978
Eye Irritation:  0.835
Respiratory Toxicity:  0.983

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  Natural Product: NPC75485

Natural Product ID:  NPC75485
Common Name*:   Zerumin A
IUPAC Name:   (Z)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-formylpent-3-enoic acid
Synonyms:   Zerumin A
Standard InCHIKey:  ZAWWSYIDZKWRAI-DTFKRFDDSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-14-6-9-17-19(2,3)10-5-11-20(17,4)16(14)8-7-15(13-21)12-18(22)23/h7,13,16-17H,1,5-6,8-12H2,2-4H3,(H,22,23)/b15-7-/t16-,17-,20+/m0/s1
SMILES:  O=C/C(=CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)/CC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2332435
PubChem CID:   11723433
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

*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
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12027740]
NPO25854 Tripterospermum lanceolatum Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[1517742]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[21106458]
NPO17780 Curcuma heyneana Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23387824]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota Leaves n.a. Database[FooDB]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26610 Spiraea formosana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25768 Senecio ruwenzoriensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26610 Spiraea formosana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13072 Rhamnus formosana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26846 Guettarda noumeana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24608 Gaertnera morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25854 Tripterospermum lanceolatum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21639 Prunus mahaleb Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26676 Daphne arisanensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17771 Senna didymobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29093 Homalium longifolium Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26208 Brombya platynema Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26357 Trachyrhamphus serratus Species Syngnathidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25732 Trichilia havanensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26481 Astragalus kabadianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14283 Ponera metallica Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24733 Celastrus dispermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15693 Guadua angustifolia Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26392 Piptadenia colubrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25996 Stenolobium stans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23410 Potentilla candicans Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17780 Curcuma heyneana Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26524 Chondria californica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25582 Aquilegia viridiflora Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26554 Hexagonia speciosa Species Carabidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19916 Phenax angustifolius Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26816 Clinopodium gracile Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25575 Streptomyces pseudovenezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26306 Pyrobaculum organotrophum Species Thermoproteaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO25086 Viburnum betulifolium Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26743 Lippia adoensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26079 Asterococcus muratae Species Cerococcidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24829 Gyrostroma missouriense n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24894 Parmelia tinctina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28819 Veronica liwanensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23589 Pecten irradians Species Pectinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25393 Coelogyne flavida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25906 Acacia linarioides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26175 Spongionella gracilis Species Dictyodendrillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10372 Kiggelaria africana Species Achariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22353 Lucilia caesar Species Calliphoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7465 Vachellia leucophloea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13051 Perymenium jelskii Species Asteraceae 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
NPT1210 Individual Protein T-cell protein-tyrosine phosphatase Homo sapiens IC50 = 7400.0 nM PMID[465739]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 10400.0 nM PMID[465739]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 96.7 % PMID[465739]

☑ 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 NPC75485 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
1.0 High Similarity NPC168975
0.9286 High Similarity NPC144947
0.8676 High Similarity NPC52449
0.8676 High Similarity NPC169275
0.8667 High Similarity NPC59436
0.8378 Intermediate Similarity NPC238146
0.8333 Intermediate Similarity NPC90055
0.8158 Intermediate Similarity NPC19907
0.7927 Intermediate Similarity NPC217394
0.7857 Intermediate Similarity NPC473229
0.7848 Intermediate Similarity NPC470429
0.7821 Intermediate Similarity NPC470428
0.7808 Intermediate Similarity NPC290350
0.7808 Intermediate Similarity NPC4370
0.7778 Intermediate Similarity NPC107258
0.7765 Intermediate Similarity NPC477973
0.7763 Intermediate Similarity NPC472813
0.7722 Intermediate Similarity NPC476949
0.7722 Intermediate Similarity NPC198240
0.7711 Intermediate Similarity NPC30984
0.7703 Intermediate Similarity NPC155198
0.7701 Intermediate Similarity NPC151722
0.7683 Intermediate Similarity NPC307258
0.7662 Intermediate Similarity NPC211641
0.7662 Intermediate Similarity NPC128346
0.7662 Intermediate Similarity NPC219232
0.7632 Intermediate Similarity NPC133253
0.7632 Intermediate Similarity NPC21944
0.7632 Intermediate Similarity NPC72343
0.7595 Intermediate Similarity NPC165711
0.7595 Intermediate Similarity NPC61952
0.7586 Intermediate Similarity NPC230064
0.7561 Intermediate Similarity NPC142683
0.7558 Intermediate Similarity NPC79027
0.7558 Intermediate Similarity NPC50488
0.7558 Intermediate Similarity NPC474396
0.75 Intermediate Similarity NPC239098
0.75 Intermediate Similarity NPC2709
0.75 Intermediate Similarity NPC86316
0.75 Intermediate Similarity NPC106416
0.75 Intermediate Similarity NPC65661
0.7471 Intermediate Similarity NPC253186
0.747 Intermediate Similarity NPC470165
0.747 Intermediate Similarity NPC469
0.7468 Intermediate Similarity NPC4509
0.7468 Intermediate Similarity NPC69143
0.7468 Intermediate Similarity NPC180886
0.7439 Intermediate Similarity NPC278459
0.7439 Intermediate Similarity NPC159148
0.7439 Intermediate Similarity NPC40228
0.7436 Intermediate Similarity NPC237591
0.7436 Intermediate Similarity NPC183503
0.7436 Intermediate Similarity NPC251970
0.7436 Intermediate Similarity NPC78527
0.7436 Intermediate Similarity NPC20025
0.7436 Intermediate Similarity NPC3753
0.7436 Intermediate Similarity NPC476046
0.7436 Intermediate Similarity NPC103958
0.7436 Intermediate Similarity NPC283908
0.7436 Intermediate Similarity NPC241854
0.7436 Intermediate Similarity NPC161923
0.7432 Intermediate Similarity NPC259156
0.7432 Intermediate Similarity NPC242945
0.7432 Intermediate Similarity NPC185587
0.7407 Intermediate Similarity NPC283789
0.7403 Intermediate Similarity NPC160817
0.7403 Intermediate Similarity NPC474562
0.7386 Intermediate Similarity NPC476187
0.7386 Intermediate Similarity NPC72845
0.7381 Intermediate Similarity NPC470812
0.7375 Intermediate Similarity NPC97377
0.7356 Intermediate Similarity NPC168131
0.7349 Intermediate Similarity NPC302661
0.7349 Intermediate Similarity NPC15910
0.7349 Intermediate Similarity NPC238991
0.7342 Intermediate Similarity NPC279666
0.7342 Intermediate Similarity NPC476346
0.7342 Intermediate Similarity NPC476795
0.7342 Intermediate Similarity NPC192540
0.7342 Intermediate Similarity NPC476844
0.7317 Intermediate Similarity NPC281880
0.7317 Intermediate Similarity NPC2482
0.7317 Intermediate Similarity NPC471514
0.7308 Intermediate Similarity NPC109576
0.7308 Intermediate Similarity NPC180015
0.7308 Intermediate Similarity NPC56747
0.7308 Intermediate Similarity NPC130016
0.7303 Intermediate Similarity NPC476416
0.7297 Intermediate Similarity NPC268039
0.7294 Intermediate Similarity NPC329738
0.7294 Intermediate Similarity NPC474680
0.7294 Intermediate Similarity NPC476602
0.7284 Intermediate Similarity NPC115515
0.7284 Intermediate Similarity NPC74410
0.7283 Intermediate Similarity NPC194196
0.7273 Intermediate Similarity NPC91369
0.7273 Intermediate Similarity NPC101651
0.7273 Intermediate Similarity NPC159748
0.7262 Intermediate Similarity NPC102197
0.7262 Intermediate Similarity NPC79945
0.7262 Intermediate Similarity NPC105803
0.7262 Intermediate Similarity NPC312480
0.7262 Intermediate Similarity NPC42476
0.725 Intermediate Similarity NPC469796
0.725 Intermediate Similarity NPC474463
0.725 Intermediate Similarity NPC470525
0.725 Intermediate Similarity NPC26504
0.725 Intermediate Similarity NPC469793
0.7241 Intermediate Similarity NPC474474
0.7241 Intermediate Similarity NPC291665
0.7241 Intermediate Similarity NPC206060
0.7241 Intermediate Similarity NPC104560
0.7229 Intermediate Similarity NPC471898
0.7229 Intermediate Similarity NPC121984
0.7229 Intermediate Similarity NPC473420
0.7229 Intermediate Similarity NPC14203
0.7229 Intermediate Similarity NPC229584
0.7222 Intermediate Similarity NPC471040
0.7222 Intermediate Similarity NPC57117
0.7222 Intermediate Similarity NPC476415
0.7215 Intermediate Similarity NPC104644
0.7215 Intermediate Similarity NPC147438
0.7209 Intermediate Similarity NPC329692
0.72 Intermediate Similarity NPC81907
0.7195 Intermediate Similarity NPC199595
0.7195 Intermediate Similarity NPC100906
0.7195 Intermediate Similarity NPC327674
0.7195 Intermediate Similarity NPC192999
0.7195 Intermediate Similarity NPC476438
0.7183 Intermediate Similarity NPC60772
0.7176 Intermediate Similarity NPC472864
0.7176 Intermediate Similarity NPC472265
0.7176 Intermediate Similarity NPC248758
0.7176 Intermediate Similarity NPC19849
0.716 Intermediate Similarity NPC472300
0.716 Intermediate Similarity NPC471899
0.716 Intermediate Similarity NPC107039
0.716 Intermediate Similarity NPC471897
0.716 Intermediate Similarity NPC283619
0.716 Intermediate Similarity NPC132542
0.7159 Intermediate Similarity NPC184663
0.7159 Intermediate Similarity NPC174342
0.7159 Intermediate Similarity NPC146554
0.7159 Intermediate Similarity NPC469546
0.7143 Intermediate Similarity NPC200513
0.7143 Intermediate Similarity NPC94200
0.7143 Intermediate Similarity NPC320514
0.7143 Intermediate Similarity NPC139459
0.7143 Intermediate Similarity NPC472867
0.7143 Intermediate Similarity NPC470813
0.7143 Intermediate Similarity NPC469799
0.7143 Intermediate Similarity NPC469806
0.7143 Intermediate Similarity NPC2524
0.7143 Intermediate Similarity NPC472239
0.7143 Intermediate Similarity NPC16321
0.7126 Intermediate Similarity NPC477926
0.7125 Intermediate Similarity NPC263698
0.7125 Intermediate Similarity NPC472256
0.7111 Intermediate Similarity NPC474185
0.7108 Intermediate Similarity NPC104545
0.7108 Intermediate Similarity NPC474956
0.7108 Intermediate Similarity NPC472478
0.7093 Intermediate Similarity NPC11711
0.7093 Intermediate Similarity NPC70685
0.7093 Intermediate Similarity NPC255174
0.7093 Intermediate Similarity NPC474537
0.7093 Intermediate Similarity NPC29447
0.7093 Intermediate Similarity NPC33881
0.7089 Intermediate Similarity NPC35656
0.7079 Intermediate Similarity NPC51486
0.7079 Intermediate Similarity NPC310479
0.7079 Intermediate Similarity NPC182136
0.7073 Intermediate Similarity NPC62336
0.7073 Intermediate Similarity NPC172066
0.7073 Intermediate Similarity NPC110094
0.7073 Intermediate Similarity NPC247783
0.7073 Intermediate Similarity NPC475994
0.7073 Intermediate Similarity NPC253561
0.7073 Intermediate Similarity NPC269543
0.7073 Intermediate Similarity NPC321514
0.7073 Intermediate Similarity NPC280654
0.7073 Intermediate Similarity NPC260385
0.7073 Intermediate Similarity NPC80088
0.7065 Intermediate Similarity NPC471039
0.7059 Intermediate Similarity NPC3856
0.7059 Intermediate Similarity NPC97913
0.7059 Intermediate Similarity NPC476927
0.7059 Intermediate Similarity NPC470948
0.7059 Intermediate Similarity NPC311070
0.7059 Intermediate Similarity NPC279639
0.7059 Intermediate Similarity NPC215893
0.7059 Intermediate Similarity NPC22611
0.7051 Intermediate Similarity NPC235586
0.7045 Intermediate Similarity NPC472870
0.7045 Intermediate Similarity NPC48107
0.7037 Intermediate Similarity NPC89294
0.7037 Intermediate Similarity NPC263582
0.7037 Intermediate Similarity NPC476601
0.7037 Intermediate Similarity NPC309399
0.7037 Intermediate Similarity NPC1254

  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 NPC75485 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
0.7143 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD4695 Discontinued
0.6923 Remote Similarity NPD6399 Phase 3
0.6915 Remote Similarity NPD4225 Approved
0.6835 Remote Similarity NPD4691 Approved
0.6818 Remote Similarity NPD3618 Phase 1
0.6813 Remote Similarity NPD7515 Phase 2
0.6809 Remote Similarity NPD7902 Approved
0.6782 Remote Similarity NPD3666 Approved
0.6782 Remote Similarity NPD3133 Approved
0.6782 Remote Similarity NPD3665 Phase 1
0.6744 Remote Similarity NPD3667 Approved
0.6709 Remote Similarity NPD4137 Phase 3
0.6702 Remote Similarity NPD4697 Phase 3
0.6667 Remote Similarity NPD4194 Approved
0.6667 Remote Similarity NPD4192 Approved
0.6667 Remote Similarity NPD4193 Approved
0.6667 Remote Similarity NPD4191 Approved
0.6667 Remote Similarity NPD7748 Approved
0.6629 Remote Similarity NPD7521 Approved
0.6629 Remote Similarity NPD7146 Approved
0.6629 Remote Similarity NPD6409 Approved
0.6629 Remote Similarity NPD7334 Approved
0.6629 Remote Similarity NPD6684 Approved
0.6629 Remote Similarity NPD5330 Approved
0.6625 Remote Similarity NPD4747 Approved
0.6593 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6591 Remote Similarity NPD4786 Approved
0.6588 Remote Similarity NPD4195 Approved
0.6585 Remote Similarity NPD4058 Approved
0.6562 Remote Similarity NPD5696 Approved
0.6552 Remote Similarity NPD4221 Approved
0.6552 Remote Similarity NPD4223 Phase 3
0.65 Remote Similarity NPD6922 Approved
0.65 Remote Similarity NPD6923 Approved
0.6489 Remote Similarity NPD7900 Approved
0.6489 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6484 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6484 Remote Similarity NPD6903 Approved
0.6484 Remote Similarity NPD5737 Approved
0.6484 Remote Similarity NPD6672 Approved
0.6458 Remote Similarity NPD6084 Phase 2
0.6458 Remote Similarity NPD6083 Phase 2
0.6452 Remote Similarity NPD6079 Approved
0.6452 Remote Similarity NPD5281 Approved
0.6452 Remote Similarity NPD5284 Approved
0.6452 Remote Similarity NPD7637 Suspended
0.6444 Remote Similarity NPD5279 Phase 3
0.6444 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6421 Remote Similarity NPD5695 Phase 3
0.6421 Remote Similarity NPD4629 Approved
0.6421 Remote Similarity NPD5210 Approved
0.642 Remote Similarity NPD7143 Approved
0.642 Remote Similarity NPD7144 Approved
0.6413 Remote Similarity NPD5328 Approved
0.6413 Remote Similarity NPD4753 Phase 2
0.6404 Remote Similarity NPD4197 Approved
0.6392 Remote Similarity NPD7638 Approved
0.6386 Remote Similarity NPD6926 Approved
0.6386 Remote Similarity NPD6924 Approved
0.6374 Remote Similarity NPD3573 Approved
0.6341 Remote Similarity NPD7152 Approved
0.6341 Remote Similarity NPD5276 Approved
0.6341 Remote Similarity NPD7151 Approved
0.6341 Remote Similarity NPD7150 Approved
0.6333 Remote Similarity NPD5329 Approved
0.6327 Remote Similarity NPD7640 Approved
0.6327 Remote Similarity NPD7639 Approved
0.6322 Remote Similarity NPD8259 Clinical (unspecified phase)
0.631 Remote Similarity NPD7339 Approved
0.631 Remote Similarity NPD6942 Approved
0.6279 Remote Similarity NPD3617 Approved
0.6264 Remote Similarity NPD4690 Approved
0.6264 Remote Similarity NPD5205 Approved
0.6264 Remote Similarity NPD4138 Approved
0.6264 Remote Similarity NPD4519 Discontinued
0.6264 Remote Similarity NPD4688 Approved
0.6264 Remote Similarity NPD4693 Phase 3
0.6264 Remote Similarity NPD4623 Approved
0.6264 Remote Similarity NPD4689 Approved
0.6264 Remote Similarity NPD5690 Phase 2
0.6235 Remote Similarity NPD6933 Approved
0.6222 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6222 Remote Similarity NPD3668 Phase 3
0.6211 Remote Similarity NPD4202 Approved
0.619 Remote Similarity NPD5733 Approved
0.619 Remote Similarity NPD6650 Approved
0.619 Remote Similarity NPD4687 Approved
0.619 Remote Similarity NPD6649 Approved
0.6186 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6186 Remote Similarity NPD7614 Phase 1
0.6186 Remote Similarity NPD5222 Approved
0.6186 Remote Similarity NPD5221 Approved
0.6173 Remote Similarity NPD3621 Clinical (unspecified phase)
0.617 Remote Similarity NPD5785 Approved
0.6163 Remote Similarity NPD6932 Approved
0.6163 Remote Similarity NPD5776 Phase 2
0.6163 Remote Similarity NPD6925 Approved
0.6154 Remote Similarity NPD1694 Approved
0.6154 Remote Similarity NPD6373 Approved
0.6154 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5363 Approved
0.6154 Remote Similarity NPD6372 Approved
0.6129 Remote Similarity NPD5208 Approved
0.6122 Remote Similarity NPD5173 Approved
0.6118 Remote Similarity NPD8264 Approved
0.6117 Remote Similarity NPD5697 Approved
0.6111 Remote Similarity NPD4788 Approved
0.6105 Remote Similarity NPD8034 Phase 2
0.6105 Remote Similarity NPD8035 Phase 2
0.6105 Remote Similarity NPD6411 Approved
0.6092 Remote Similarity NPD7145 Approved
0.6092 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6092 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6087 Remote Similarity NPD5280 Approved
0.6087 Remote Similarity NPD4694 Approved
0.6082 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6076 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6064 Remote Similarity NPD6080 Approved
0.6064 Remote Similarity NPD6904 Approved
0.6064 Remote Similarity NPD6673 Approved
0.6058 Remote Similarity NPD6881 Approved
0.6058 Remote Similarity NPD6899 Approved
0.6058 Remote Similarity NPD6686 Approved
0.6058 Remote Similarity NPD6011 Approved
0.6053 Remote Similarity NPD287 Approved
0.6023 Remote Similarity NPD7645 Phase 2
0.6023 Remote Similarity NPD6929 Approved
0.6023 Remote Similarity NPD6683 Phase 2
0.6019 Remote Similarity NPD5739 Approved
0.6019 Remote Similarity NPD6675 Approved
0.6019 Remote Similarity NPD7128 Approved
0.6019 Remote Similarity NPD6402 Approved
0.6 Remote Similarity NPD5207 Approved
0.6 Remote Similarity NPD6404 Discontinued
0.6 Remote Similarity NPD5286 Approved
0.6 Remote Similarity NPD4696 Approved
0.6 Remote Similarity NPD4784 Approved
0.6 Remote Similarity NPD6014 Approved
0.6 Remote Similarity NPD4785 Approved
0.6 Remote Similarity NPD6013 Approved
0.6 Remote Similarity NPD5285 Approved
0.6 Remote Similarity NPD6012 Approved
0.5979 Remote Similarity NPD6001 Approved
0.5978 Remote Similarity NPD1696 Phase 3
0.5962 Remote Similarity NPD5701 Approved
0.596 Remote Similarity NPD4755 Approved
0.5955 Remote Similarity NPD6931 Approved
0.5955 Remote Similarity NPD7514 Phase 3
0.5955 Remote Similarity NPD7509 Discontinued
0.5955 Remote Similarity NPD7525 Registered
0.5955 Remote Similarity NPD6930 Phase 2
0.5955 Remote Similarity NPD7332 Phase 2
0.5952 Remote Similarity NPD4243 Approved
0.5943 Remote Similarity NPD7102 Approved
0.5943 Remote Similarity NPD7290 Approved
0.5943 Remote Similarity NPD6883 Approved
0.5941 Remote Similarity NPD5223 Approved
0.5938 Remote Similarity NPD5693 Phase 1
0.593 Remote Similarity NPD8039 Approved
0.5926 Remote Similarity NPD7331 Phase 2
0.5918 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5914 Remote Similarity NPD6098 Approved
0.5909 Remote Similarity NPD7115 Discovery
0.5905 Remote Similarity NPD7320 Approved
0.59 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5895 Remote Similarity NPD6101 Approved
0.5895 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5889 Remote Similarity NPD6902 Approved
0.5889 Remote Similarity NPD6898 Phase 1
0.5889 Remote Similarity NPD5369 Approved
0.5889 Remote Similarity NPD8028 Phase 2
0.5888 Remote Similarity NPD6617 Approved
0.5888 Remote Similarity NPD8130 Phase 1
0.5888 Remote Similarity NPD6847 Approved
0.5888 Remote Similarity NPD6869 Approved
0.5882 Remote Similarity NPD5211 Phase 2
0.5882 Remote Similarity NPD5225 Approved
0.5882 Remote Similarity NPD5226 Approved
0.5882 Remote Similarity NPD5224 Approved
0.5882 Remote Similarity NPD4633 Approved
0.5865 Remote Similarity NPD6008 Approved
0.5859 Remote Similarity NPD7732 Phase 3
0.5842 Remote Similarity NPD4700 Approved
0.5833 Remote Similarity NPD8297 Approved
0.5833 Remote Similarity NPD4096 Approved
0.5833 Remote Similarity NPD6882 Approved
0.5833 Remote Similarity NPD5692 Phase 3
0.5825 Remote Similarity NPD5174 Approved
0.5825 Remote Similarity NPD5175 Approved
0.5824 Remote Similarity NPD5209 Approved
0.5824 Remote Similarity NPD4270 Approved
0.5824 Remote Similarity NPD4269 Approved
0.5802 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4219 Approved
0.5789 Remote Similarity NPD4518 Approved
0.578 Remote Similarity NPD4632 Approved
0.5778 Remote Similarity NPD4252 Approved
0.5778 Remote Similarity NPD4821 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