Structure

Physi-Chem Properties

Molecular Weight:  302.22
Volume:  344.398
LogP:  3.755
LogD:  3.488
LogS:  -4.241
# Rotatable Bonds:  4
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.559
Synthetic Accessibility Score:  4.288
Fsp3:  0.65
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.023
MDCK Permeability:  3.448763891356066e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.203
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.163
Plasma Protein Binding (PPB):  90.18402862548828%
Volume Distribution (VD):  0.364
Pgp-substrate:  8.656021118164062%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.54
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.772
CYP2C9-inhibitor:  0.119
CYP2C9-substrate:  0.838
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.576
CYP3A4-inhibitor:  0.131
CYP3A4-substrate:  0.211

ADMET: Excretion

Clearance (CL):  1.099
Half-life (T1/2):  0.577

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.145
Drug-inuced Liver Injury (DILI):  0.04
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.174
Maximum Recommended Daily Dose:  0.897
Skin Sensitization:  0.771
Carcinogencity:  0.241
Eye Corrosion:  0.913
Eye Irritation:  0.963
Respiratory Toxicity:  0.962

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  Natural Product: NPC3753

Natural Product ID:  NPC3753
Common Name*:   (4R,5R,9S,10R)-8(17),12,14-Labdatrien-18-Oic Acid
IUPAC Name:   (1R,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:  
Standard InCHIKey:  YGBZFOQXPOGACY-ONIUZDBUSA-N
Standard InCHI:  InChI=1S/C20H30O2/c1-6-14(2)8-10-16-15(3)9-11-17-19(16,4)12-7-13-20(17,5)18(21)22/h6,8,16-17H,1,3,7,9-13H2,2,4-5H3,(H,21,22)/b14-8+/t16-,17+,19+,20+/m0/s1
SMILES:  C=C/C(=C/C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3402737
PubChem CID:   12303810
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
NPO17839 Machaerium mucronulatum Species Dolichopodidae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)94598-9]
NPO25454 Plumbago europaea Species Plumbaginaceae Eukaryota n.a. root n.a. DOI[10.2225/vol5-issue3-fulltext-4]
NPO21302 Cladosporium herbarum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. PMID[11325242]
NPO7174 Callyspongia truncata Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[12088440]
NPO7174 Callyspongia truncata Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[12713420]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15009205]
NPO21302 Cladosporium herbarum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. PMID[16038560]
NPO1994 Panax stipuleanatus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[20951582]
NPO1338 Arcangelisia gusanlung Species Menispermaceae Eukaryota n.a. stem n.a. PMID[21500777]
NPO9604 Amycolatopsis lurida Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. PMID[25323720]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota rhizomes Liaoning province, China 2011-SEP PMID[25927664]
NPO16966 Leptospermum scoparium Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[26731565]
NPO18983 Cleidion brevipetiolatum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31419126]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16293 Babylonia japonica Species Buccinidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25454 Plumbago europaea Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18306 Juniperus thurifera Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13963 Laurencia elata Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25454 Plumbago europaea Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17831 Millettia racemosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18306 Juniperus thurifera Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13963 Laurencia elata Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16293 Babylonia japonica Species Buccinidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5764 Ophioglossum vulgatum Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15358 Entandrophragma cylindricum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18173 Pyrocystis lunula Species Pyrocystaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17831 Millettia racemosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1338 Arcangelisia gusanlung Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3050 Cladonia pseudodidyma Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25454 Plumbago europaea Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18983 Cleidion brevipetiolatum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9535 Cortinarius basirubescens Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15608 Tanacetum santolina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18306 Juniperus thurifera Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12801 Aglaia meridionalis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21302 Cladosporium herbarum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18520 Helipterum strictum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18792 Crotalaria lechnaultii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7807 Polyporus sulphureus Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17275 Chamaemelum scariosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13963 Laurencia elata Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16966 Leptospermum scoparium Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17709 Timonius kaniensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7174 Callyspongia truncata Species Callyspongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17802 Simmondsia chinensis Species Simmondsiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18061 Anacystis cyanea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12282 Parmelia conspersa Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3746 Hesperocyparis nevadensis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9604 Amycolatopsis lurida Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18707 Allium ursinum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3881 Erucastrum gallicum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18847 Copaifera paupera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17190 Senecio erraticus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12072 Escallonia philippiana Species Escalloniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18242 Gleichenia glauca Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17068 Talaromyces wortmanni Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13594 Hippocratea indica Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17596 Ficus maxima Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11603 Lathyrus macrorrhizus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1994 Panax stipuleanatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5764 Ophioglossum vulgatum Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18377 Chaetomium retardatum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10712 Tabebuia rosea Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11677 Lactobacillus acidophilus Species Lactobacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15358 Entandrophragma cylindricum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17373 Cunninghamia lanceolata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21938 Coleus carnosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16829 Dunaliella acidophila Species Dunaliellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17839 Machaerium mucronulatum Species Dolichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16293 Babylonia japonica Species Buccinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17718 Artemisia schmidtiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19057 Lentinellus omphalodes Species Auriscalpiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19189 Brickellia pendula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18575 Ochtodes crockeri Species Rhizophyllidaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 > 100000.0 nM PMID[482593]

☑ 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 NPC3753 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 NPC237591
0.9855 High Similarity NPC476844
0.9429 High Similarity NPC103958
0.9429 High Similarity NPC183503
0.9429 High Similarity NPC161923
0.9429 High Similarity NPC283908
0.9296 High Similarity NPC279666
0.9296 High Similarity NPC192540
0.9167 High Similarity NPC69143
0.9167 High Similarity NPC309399
0.9155 High Similarity NPC241854
0.9155 High Similarity NPC301065
0.9155 High Similarity NPC251970
0.9155 High Similarity NPC476046
0.8873 High Similarity NPC160817
0.8831 High Similarity NPC312480
0.8816 High Similarity NPC142244
0.8784 High Similarity NPC471899
0.8784 High Similarity NPC107039
0.8784 High Similarity NPC61952
0.8784 High Similarity NPC471897
0.8784 High Similarity NPC165711
0.8767 High Similarity NPC201027
0.8714 High Similarity NPC36616
0.8714 High Similarity NPC290445
0.8667 High Similarity NPC198240
0.8667 High Similarity NPC260385
0.8667 High Similarity NPC59436
0.8667 High Similarity NPC239098
0.8667 High Similarity NPC110094
0.8667 High Similarity NPC179028
0.8667 High Similarity NPC280654
0.8649 High Similarity NPC89294
0.863 High Similarity NPC18819
0.863 High Similarity NPC46610
0.863 High Similarity NPC166797
0.859 High Similarity NPC102197
0.859 High Similarity NPC70834
0.8553 High Similarity NPC199595
0.8553 High Similarity NPC231431
0.8553 High Similarity NPC16394
0.8553 High Similarity NPC158846
0.8514 High Similarity NPC476795
0.8472 Intermediate Similarity NPC91369
0.8462 Intermediate Similarity NPC302661
0.8462 Intermediate Similarity NPC238991
0.8442 Intermediate Similarity NPC37038
0.8442 Intermediate Similarity NPC104545
0.8421 Intermediate Similarity NPC321514
0.8421 Intermediate Similarity NPC247783
0.8421 Intermediate Similarity NPC269543
0.84 Intermediate Similarity NPC180886
0.84 Intermediate Similarity NPC899
0.8378 Intermediate Similarity NPC255168
0.8378 Intermediate Similarity NPC306928
0.8378 Intermediate Similarity NPC213223
0.8375 Intermediate Similarity NPC76333
0.8356 Intermediate Similarity NPC72343
0.8354 Intermediate Similarity NPC83569
0.8354 Intermediate Similarity NPC167103
0.8354 Intermediate Similarity NPC69279
0.8333 Intermediate Similarity NPC274050
0.8333 Intermediate Similarity NPC162632
0.8333 Intermediate Similarity NPC229584
0.8333 Intermediate Similarity NPC267691
0.8333 Intermediate Similarity NPC263272
0.8333 Intermediate Similarity NPC147066
0.8333 Intermediate Similarity NPC278459
0.8333 Intermediate Similarity NPC40228
0.8333 Intermediate Similarity NPC221647
0.8333 Intermediate Similarity NPC14203
0.8333 Intermediate Similarity NPC90055
0.8333 Intermediate Similarity NPC471898
0.8312 Intermediate Similarity NPC196827
0.8312 Intermediate Similarity NPC477371
0.8312 Intermediate Similarity NPC274996
0.8312 Intermediate Similarity NPC327674
0.8312 Intermediate Similarity NPC474113
0.8289 Intermediate Similarity NPC97377
0.8243 Intermediate Similarity NPC330659
0.8243 Intermediate Similarity NPC36310
0.8243 Intermediate Similarity NPC244708
0.8243 Intermediate Similarity NPC35656
0.8243 Intermediate Similarity NPC161187
0.8243 Intermediate Similarity NPC177826
0.8228 Intermediate Similarity NPC69101
0.8228 Intermediate Similarity NPC251779
0.8219 Intermediate Similarity NPC235586
0.8205 Intermediate Similarity NPC477057
0.8182 Intermediate Similarity NPC4827
0.8182 Intermediate Similarity NPC74410
0.8148 Intermediate Similarity NPC29447
0.8148 Intermediate Similarity NPC269638
0.8148 Intermediate Similarity NPC474537
0.8143 Intermediate Similarity NPC234767
0.8125 Intermediate Similarity NPC477852
0.8125 Intermediate Similarity NPC215893
0.8125 Intermediate Similarity NPC200752
0.8101 Intermediate Similarity NPC121984
0.8101 Intermediate Similarity NPC201912
0.8101 Intermediate Similarity NPC473420
0.8101 Intermediate Similarity NPC474955
0.8101 Intermediate Similarity NPC477372
0.8101 Intermediate Similarity NPC38350
0.8101 Intermediate Similarity NPC327002
0.8101 Intermediate Similarity NPC225515
0.8052 Intermediate Similarity NPC472300
0.8049 Intermediate Similarity NPC82979
0.8049 Intermediate Similarity NPC6247
0.8025 Intermediate Similarity NPC194937
0.8025 Intermediate Similarity NPC248758
0.8025 Intermediate Similarity NPC156981
0.8025 Intermediate Similarity NPC19849
0.8025 Intermediate Similarity NPC476038
0.8025 Intermediate Similarity NPC96095
0.8025 Intermediate Similarity NPC477289
0.8025 Intermediate Similarity NPC139566
0.8025 Intermediate Similarity NPC472864
0.8 Intermediate Similarity NPC320514
0.8 Intermediate Similarity NPC472813
0.8 Intermediate Similarity NPC260956
0.8 Intermediate Similarity NPC301244
0.8 Intermediate Similarity NPC133391
0.8 Intermediate Similarity NPC73882
0.8 Intermediate Similarity NPC473986
0.8 Intermediate Similarity NPC474018
0.8 Intermediate Similarity NPC296367
0.7976 Intermediate Similarity NPC474972
0.7976 Intermediate Similarity NPC95246
0.7976 Intermediate Similarity NPC118011
0.7976 Intermediate Similarity NPC161751
0.7976 Intermediate Similarity NPC36668
0.7975 Intermediate Similarity NPC26139
0.7975 Intermediate Similarity NPC476809
0.7952 Intermediate Similarity NPC128644
0.7952 Intermediate Similarity NPC236618
0.7949 Intermediate Similarity NPC189485
0.7949 Intermediate Similarity NPC275494
0.7949 Intermediate Similarity NPC169095
0.7949 Intermediate Similarity NPC471409
0.7927 Intermediate Similarity NPC106416
0.7927 Intermediate Similarity NPC283733
0.7927 Intermediate Similarity NPC65661
0.7927 Intermediate Similarity NPC86316
0.7922 Intermediate Similarity NPC20466
0.7922 Intermediate Similarity NPC476601
0.7922 Intermediate Similarity NPC104806
0.7922 Intermediate Similarity NPC246445
0.7917 Intermediate Similarity NPC149680
0.7917 Intermediate Similarity NPC103734
0.7901 Intermediate Similarity NPC97913
0.7901 Intermediate Similarity NPC477373
0.7901 Intermediate Similarity NPC310470
0.7901 Intermediate Similarity NPC105803
0.7875 Intermediate Similarity NPC14151
0.7867 Intermediate Similarity NPC133253
0.7857 Intermediate Similarity NPC72397
0.7857 Intermediate Similarity NPC24816
0.7848 Intermediate Similarity NPC192329
0.7848 Intermediate Similarity NPC215843
0.7831 Intermediate Similarity NPC239685
0.7831 Intermediate Similarity NPC186975
0.7831 Intermediate Similarity NPC472869
0.7831 Intermediate Similarity NPC325594
0.7831 Intermediate Similarity NPC324063
0.7831 Intermediate Similarity NPC73038
0.7831 Intermediate Similarity NPC155011
0.7821 Intermediate Similarity NPC471035
0.7821 Intermediate Similarity NPC68828
0.7821 Intermediate Similarity NPC212661
0.7821 Intermediate Similarity NPC238227
0.7821 Intermediate Similarity NPC66105
0.7821 Intermediate Similarity NPC474433
0.7816 Intermediate Similarity NPC80365
0.7805 Intermediate Similarity NPC165064
0.7805 Intermediate Similarity NPC164577
0.7805 Intermediate Similarity NPC472865
0.7792 Intermediate Similarity NPC39362
0.7791 Intermediate Similarity NPC204341
0.7778 Intermediate Similarity NPC123880
0.7778 Intermediate Similarity NPC15910
0.7778 Intermediate Similarity NPC471159
0.7778 Intermediate Similarity NPC469806
0.7778 Intermediate Similarity NPC469799
0.7778 Intermediate Similarity NPC268039
0.7765 Intermediate Similarity NPC102414
0.7765 Intermediate Similarity NPC112454
0.7765 Intermediate Similarity NPC474686
0.7765 Intermediate Similarity NPC262043
0.7765 Intermediate Similarity NPC66344
0.7765 Intermediate Similarity NPC128496
0.7765 Intermediate Similarity NPC84271
0.7765 Intermediate Similarity NPC77168
0.775 Intermediate Similarity NPC2482
0.775 Intermediate Similarity NPC267517
0.7738 Intermediate Similarity NPC474684
0.7738 Intermediate Similarity NPC476409
0.7738 Intermediate Similarity NPC181327
0.7738 Intermediate Similarity NPC307426
0.7738 Intermediate Similarity NPC130577

  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 NPC3753 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
0.7791 Intermediate Similarity NPD5281 Approved
0.7791 Intermediate Similarity NPD5284 Approved
0.7765 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD4695 Discontinued
0.7561 Intermediate Similarity NPD4221 Approved
0.7561 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD3667 Approved
0.7561 Intermediate Similarity NPD4223 Phase 3
0.7412 Intermediate Similarity NPD4519 Discontinued
0.7412 Intermediate Similarity NPD5279 Phase 3
0.7412 Intermediate Similarity NPD5280 Approved
0.7412 Intermediate Similarity NPD4623 Approved
0.7412 Intermediate Similarity NPD4694 Approved
0.7386 Intermediate Similarity NPD7515 Phase 2
0.7386 Intermediate Similarity NPD6411 Approved
0.7381 Intermediate Similarity NPD4197 Approved
0.7381 Intermediate Similarity NPD3133 Approved
0.7381 Intermediate Similarity NPD3666 Approved
0.7381 Intermediate Similarity NPD3665 Phase 1
0.7381 Intermediate Similarity NPD4786 Approved
0.7342 Intermediate Similarity NPD8039 Approved
0.7326 Intermediate Similarity NPD3573 Approved
0.7303 Intermediate Similarity NPD6399 Phase 3
0.7294 Intermediate Similarity NPD5329 Approved
0.7284 Intermediate Similarity NPD3617 Approved
0.7273 Intermediate Similarity NPD5207 Approved
0.7222 Intermediate Similarity NPD7748 Approved
0.7215 Intermediate Similarity NPD4058 Approved
0.7209 Intermediate Similarity NPD7521 Approved
0.7209 Intermediate Similarity NPD7334 Approved
0.7209 Intermediate Similarity NPD6684 Approved
0.7209 Intermediate Similarity NPD6098 Approved
0.7209 Intermediate Similarity NPD4138 Approved
0.7209 Intermediate Similarity NPD4690 Approved
0.7209 Intermediate Similarity NPD6409 Approved
0.7209 Intermediate Similarity NPD5205 Approved
0.7209 Intermediate Similarity NPD4693 Phase 3
0.7209 Intermediate Similarity NPD5690 Phase 2
0.7209 Intermediate Similarity NPD3618 Phase 1
0.7209 Intermediate Similarity NPD4689 Approved
0.7209 Intermediate Similarity NPD4688 Approved
0.7209 Intermediate Similarity NPD5330 Approved
0.7209 Intermediate Similarity NPD7146 Approved
0.7206 Intermediate Similarity NPD3172 Approved
0.7191 Intermediate Similarity NPD5694 Approved
0.7159 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD6101 Approved
0.7101 Intermediate Similarity NPD4266 Approved
0.7101 Intermediate Similarity NPD3195 Phase 2
0.7101 Intermediate Similarity NPD3196 Approved
0.7101 Intermediate Similarity NPD3194 Approved
0.7093 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD4096 Approved
0.7079 Intermediate Similarity NPD5692 Phase 3
0.7045 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD6903 Approved
0.7045 Intermediate Similarity NPD5737 Approved
0.7045 Intermediate Similarity NPD4518 Approved
0.7045 Intermediate Similarity NPD6672 Approved
0.7045 Intermediate Similarity NPD5208 Approved
0.7021 Intermediate Similarity NPD6404 Discontinued
0.7011 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6079 Approved
0.7 Intermediate Similarity NPD4687 Approved
0.7 Intermediate Similarity NPD6924 Approved
0.7 Intermediate Similarity NPD6926 Approved
0.7 Intermediate Similarity NPD6050 Approved
0.6989 Remote Similarity NPD6084 Phase 2
0.6989 Remote Similarity NPD7902 Approved
0.6989 Remote Similarity NPD6083 Phase 2
0.6988 Remote Similarity NPD4195 Approved
0.6977 Remote Similarity NPD3668 Phase 3
0.6974 Remote Similarity NPD4224 Phase 2
0.6966 Remote Similarity NPD4753 Phase 2
0.6966 Remote Similarity NPD5328 Approved
0.6966 Remote Similarity NPD6080 Approved
0.6966 Remote Similarity NPD6904 Approved
0.6966 Remote Similarity NPD6673 Approved
0.6962 Remote Similarity NPD5276 Approved
0.6957 Remote Similarity NPD5695 Phase 3
0.6923 Remote Similarity NPD5778 Approved
0.6923 Remote Similarity NPD5779 Approved
0.6923 Remote Similarity NPD4137 Phase 3
0.6915 Remote Similarity NPD5696 Approved
0.6892 Remote Similarity NPD4193 Approved
0.6892 Remote Similarity NPD4192 Approved
0.6892 Remote Similarity NPD4191 Approved
0.6892 Remote Similarity NPD4194 Approved
0.6882 Remote Similarity NPD7614 Phase 1
0.6867 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6835 Remote Similarity NPD4747 Approved
0.6835 Remote Similarity NPD7144 Approved
0.6835 Remote Similarity NPD7143 Approved
0.6835 Remote Similarity NPD4691 Approved
0.6829 Remote Similarity NPD6933 Approved
0.6824 Remote Similarity NPD4692 Approved
0.6824 Remote Similarity NPD4139 Approved
0.6824 Remote Similarity NPD857 Phase 3
0.6813 Remote Similarity NPD7637 Suspended
0.6813 Remote Similarity NPD5693 Phase 1
0.6795 Remote Similarity NPD3621 Clinical (unspecified phase)
0.679 Remote Similarity NPD4784 Approved
0.679 Remote Similarity NPD4785 Approved
0.679 Remote Similarity NPD5733 Approved
0.6774 Remote Similarity NPD4629 Approved
0.6774 Remote Similarity NPD5210 Approved
0.6753 Remote Similarity NPD7331 Phase 2
0.675 Remote Similarity NPD7151 Approved
0.675 Remote Similarity NPD7152 Approved
0.675 Remote Similarity NPD4243 Approved
0.675 Remote Similarity NPD7150 Approved
0.6739 Remote Similarity NPD1088 Approved
0.6739 Remote Similarity NPD4202 Approved
0.6739 Remote Similarity NPD5133 Approved
0.6709 Remote Similarity NPD6923 Approved
0.6709 Remote Similarity NPD6922 Approved
0.6702 Remote Similarity NPD5221 Approved
0.6702 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6702 Remote Similarity NPD5222 Approved
0.6667 Remote Similarity NPD28 Approved
0.6667 Remote Similarity NPD4788 Approved
0.6667 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6667 Remote Similarity NPD29 Approved
0.6667 Remote Similarity NPD7900 Approved
0.6667 Remote Similarity NPD6001 Approved
0.6667 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5173 Approved
0.663 Remote Similarity NPD8034 Phase 2
0.663 Remote Similarity NPD8035 Phase 2
0.6627 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6623 Remote Similarity NPD7341 Phase 2
0.6618 Remote Similarity NPD3173 Approved
0.66 Remote Similarity NPD5697 Approved
0.6596 Remote Similarity NPD688 Clinical (unspecified phase)
0.6596 Remote Similarity NPD5654 Approved
0.6596 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6593 Remote Similarity NPD5347 Phase 2
0.6593 Remote Similarity NPD5346 Phase 2
0.6588 Remote Similarity NPD6929 Approved
0.6562 Remote Similarity NPD7638 Approved
0.6548 Remote Similarity NPD6932 Approved
0.6543 Remote Similarity NPD6081 Approved
0.6535 Remote Similarity NPD6011 Approved
0.6535 Remote Similarity NPD6899 Approved
0.6535 Remote Similarity NPD6881 Approved
0.6526 Remote Similarity NPD4697 Phase 3
0.6522 Remote Similarity NPD1090 Approved
0.6522 Remote Similarity NPD1086 Approved
0.6522 Remote Similarity NPD1089 Approved
0.6517 Remote Similarity NPD1694 Approved
0.6512 Remote Similarity NPD6931 Approved
0.6512 Remote Similarity NPD5368 Approved
0.6512 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6512 Remote Similarity NPD6930 Phase 2
0.6512 Remote Similarity NPD7509 Discontinued
0.6506 Remote Similarity NPD4190 Phase 3
0.6506 Remote Similarity NPD6942 Approved
0.6506 Remote Similarity NPD8264 Approved
0.6506 Remote Similarity NPD7339 Approved
0.6506 Remote Similarity NPD5275 Approved
0.65 Remote Similarity NPD6402 Approved
0.65 Remote Similarity NPD5739 Approved
0.65 Remote Similarity NPD7128 Approved
0.65 Remote Similarity NPD6675 Approved
0.6495 Remote Similarity NPD7640 Approved
0.6495 Remote Similarity NPD4696 Approved
0.6495 Remote Similarity NPD5285 Approved
0.6495 Remote Similarity NPD7639 Approved
0.6495 Remote Similarity NPD2066 Phase 3
0.6495 Remote Similarity NPD5286 Approved
0.6477 Remote Similarity NPD5362 Discontinued
0.6471 Remote Similarity NPD6014 Approved
0.6471 Remote Similarity NPD622 Approved
0.6471 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7145 Approved
0.6471 Remote Similarity NPD6012 Approved
0.6471 Remote Similarity NPD6013 Approved
0.6465 Remote Similarity NPD1930 Approved
0.6465 Remote Similarity NPD1929 Approved
0.6465 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6458 Remote Similarity NPD4755 Approved
0.6458 Remote Similarity NPD5959 Approved
0.6437 Remote Similarity NPD5369 Approved
0.6437 Remote Similarity NPD226 Approved
0.6436 Remote Similarity NPD5701 Approved
0.6429 Remote Similarity NPD5223 Approved
0.6413 Remote Similarity NPD800 Approved
0.641 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6408 Remote Similarity NPD7102 Approved
0.6408 Remote Similarity NPD6883 Approved
0.6408 Remote Similarity NPD7290 Approved
0.6395 Remote Similarity NPD7645 Phase 2
0.6392 Remote Similarity NPD4225 Approved
0.6386 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6374 Remote Similarity NPD4793 Discontinued
0.6373 Remote Similarity NPD6686 Approved
0.6373 Remote Similarity NPD7320 Approved
0.6364 Remote Similarity NPD5224 Approved
0.6364 Remote Similarity NPD4633 Approved
0.6364 Remote Similarity NPD5211 Phase 2

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data