Structure

Physi-Chem Properties

Molecular Weight:  290.22
Volume:  323.818
LogP:  4.419
LogD:  4.153
LogS:  -4.993
# Rotatable Bonds:  1
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.508
Synthetic Accessibility Score:  5.027
Fsp3:  0.842
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:  -4.654
MDCK Permeability:  2.535055136831943e-05
Pgp-inhibitor:  0.131
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.204
Plasma Protein Binding (PPB):  92.57276916503906%
Volume Distribution (VD):  1.457
Pgp-substrate:  5.496187210083008%

ADMET: Metabolism

CYP1A2-inhibitor:  0.195
CYP1A2-substrate:  0.509
CYP2C19-inhibitor:  0.547
CYP2C19-substrate:  0.922
CYP2C9-inhibitor:  0.485
CYP2C9-substrate:  0.695
CYP2D6-inhibitor:  0.078
CYP2D6-substrate:  0.721
CYP3A4-inhibitor:  0.713
CYP3A4-substrate:  0.31

ADMET: Excretion

Clearance (CL):  4.342
Half-life (T1/2):  0.121

ADMET: Toxicity

hERG Blockers:  0.127
Human Hepatotoxicity (H-HT):  0.558
Drug-inuced Liver Injury (DILI):  0.047
AMES Toxicity:  0.028
Rat Oral Acute Toxicity:  0.241
Maximum Recommended Daily Dose:  0.876
Skin Sensitization:  0.923
Carcinogencity:  0.833
Eye Corrosion:  0.345
Eye Irritation:  0.278
Respiratory Toxicity:  0.96

Download Data

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

  Natural Product: NPC219809

Natural Product ID:  NPC219809
Common Name*:   9,13-Epoxy-16-Norlabda-13E-En-15-Al
IUPAC Name:   (2E)-2-[(4aS,7R,8R,8aS)-4,4,7,8a-tetramethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,5'-oxolane]-2'-ylidene]acetaldehyde
Synonyms:  
Standard InCHIKey:  NUOORXQOTIGTCT-ZREGWRRISA-N
Standard InCHI:  InChI=1S/C19H30O2/c1-14-6-7-16-17(2,3)10-5-11-18(16,4)19(14)12-8-15(21-19)9-13-20/h9,13-14,16H,5-8,10-12H2,1-4H3/b15-9+/t14-,16+,18+,19-/m1/s1
SMILES:  O=C/C=C/1CC[C@@]2(O1)[C@H](C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2436605
PubChem CID:   11208535
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002648] Tetrahydrofurans

*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
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota Fruits n.a. n.a. PMID[10579867]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota subterranean part n.a. n.a. PMID[11374949]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. fruit n.a. PMID[11536386]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[11975496]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. fruit n.a. PMID[15577254]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[15621610]
NPO17785 Avrainvillea nigricans Species Udoteaceae Eukaryota n.a. n.a. n.a. PMID[16180830]
NPO22123 Disepalum plagioneurum Species Annonaceae Eukaryota leaves Tam Kim, Cao Bang Province, in North Vietnam 2000-JUN PMID[16989521]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota whole plant Cholistan desert near district Bahawalpur (Punjab), Pakistan 2003-Oct PMID[20542692]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[2082684]
NPO18212 Rhododendron ferrugineum Species Ericaceae Eukaryota n.a. leaf n.a. PMID[21443171]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[21922656]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[23327905]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[24035341]
NPO18530 Shigella flexneri Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26918643]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[28453270]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[3254039]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[3256207]
NPO17785 Avrainvillea nigricans Species Udoteaceae Eukaryota n.a. n.a. n.a. PMID[3668556]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22819 Rodgersia podophylla Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23178 Jasminum grandiflorum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22188 Piper aequale Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22819 Rodgersia podophylla Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23178 Jasminum grandiflorum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21875 Persea indica Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22188 Piper aequale Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14247 Melaleuca uncinata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21113 Coronophora gregaria Species Nitschkiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18212 Rhododendron ferrugineum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19921 Polyphaga sinensis Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22188 Piper aequale Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17785 Avrainvillea nigricans Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7080 Monascus purpureus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21998 Corydalis cornuta Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20043 Vallaris solanacea Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22940 Delphinium campylocentrum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23178 Jasminum grandiflorum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20360 Mentha pulegiformis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21247 Nephroma australe Species Nephromataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18530 Shigella flexneri Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22454 Picris radicata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18571 Drypetes roxburghii Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21298 Leucanthemum maximum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19074 Buddleja variabilis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20678 Grindelia nana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20808 Halopitys incurvus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO22819 Rodgersia podophylla Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16146 Osmundaria colensoi Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20184 Streptomyces misawanensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20536 Salvia nubicola Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21505 Calea megacephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21798 Dacrydium biforme Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21636 Didemnum inarmatum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22062 Leptothorax acervorum Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7865 Scapania nemorea Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17108 Lecanora lividocinerea Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21736 Abies nobilis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22582 Smenospongia echina Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21875 Persea indica Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22762 Eremophila serrulata Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22123 Disepalum plagioneurum Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14394 Hakea saligna Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22323 Pinus picea Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22994 Cordyline indivisa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5952 Phegopteris bukoensis Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22248 Alkanna hirsutissima Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12225 Amsinckia menziesii Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22710 Acrocomia sclerocarpa Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23057 Primula hirsuta Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23218 Viscum coloratum Species Viscaceae 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
NPT113 Cell Line RAW264.7 Mus musculus Activity > 90.0 % PMID[573889]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 41800.0 nM PMID[573889]

☑ 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 NPC219809 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
0.8765 High Similarity NPC264546
0.8462 Intermediate Similarity NPC283789
0.8 Intermediate Similarity NPC106332
0.7975 Intermediate Similarity NPC470428
0.7907 Intermediate Similarity NPC170633
0.7875 Intermediate Similarity NPC476949
0.7821 Intermediate Similarity NPC22134
0.7821 Intermediate Similarity NPC78527
0.7778 Intermediate Similarity NPC470429
0.7711 Intermediate Similarity NPC470813
0.7619 Intermediate Similarity NPC476927
0.7614 Intermediate Similarity NPC38952
0.7529 Intermediate Similarity NPC96055
0.7529 Intermediate Similarity NPC306951
0.75 Intermediate Similarity NPC142683
0.7471 Intermediate Similarity NPC89747
0.7467 Intermediate Similarity NPC474768
0.7444 Intermediate Similarity NPC474185
0.7442 Intermediate Similarity NPC474013
0.7442 Intermediate Similarity NPC133652
0.7439 Intermediate Similarity NPC253561
0.7439 Intermediate Similarity NPC80088
0.7416 Intermediate Similarity NPC223093
0.7416 Intermediate Similarity NPC328141
0.7386 Intermediate Similarity NPC93411
0.7381 Intermediate Similarity NPC170303
0.7381 Intermediate Similarity NPC475665
0.7363 Intermediate Similarity NPC471040
0.7342 Intermediate Similarity NPC167706
0.7333 Intermediate Similarity NPC52449
0.7333 Intermediate Similarity NPC169275
0.7317 Intermediate Similarity NPC132542
0.7303 Intermediate Similarity NPC82876
0.7294 Intermediate Similarity NPC155521
0.7294 Intermediate Similarity NPC2524
0.7294 Intermediate Similarity NPC256112
0.7273 Intermediate Similarity NPC38885
0.7273 Intermediate Similarity NPC166857
0.7273 Intermediate Similarity NPC475772
0.7262 Intermediate Similarity NPC472301
0.7241 Intermediate Similarity NPC22133
0.7241 Intermediate Similarity NPC300985
0.7241 Intermediate Similarity NPC2709
0.7229 Intermediate Similarity NPC59436
0.7222 Intermediate Similarity NPC474842
0.7222 Intermediate Similarity NPC475965
0.7222 Intermediate Similarity NPC302280
0.7222 Intermediate Similarity NPC212369
0.7209 Intermediate Similarity NPC139206
0.7204 Intermediate Similarity NPC122324
0.7204 Intermediate Similarity NPC106425
0.7204 Intermediate Similarity NPC151725
0.7204 Intermediate Similarity NPC471039
0.7191 Intermediate Similarity NPC215831
0.7191 Intermediate Similarity NPC291665
0.7191 Intermediate Similarity NPC206060
0.7176 Intermediate Similarity NPC474085
0.7176 Intermediate Similarity NPC90055
0.7176 Intermediate Similarity NPC119229
0.7176 Intermediate Similarity NPC6434
0.7176 Intermediate Similarity NPC476101
0.7176 Intermediate Similarity NPC290495
0.7176 Intermediate Similarity NPC195334
0.7176 Intermediate Similarity NPC70927
0.7176 Intermediate Similarity NPC473217
0.7174 Intermediate Similarity NPC269729
0.716 Intermediate Similarity NPC201048
0.716 Intermediate Similarity NPC476366
0.7159 Intermediate Similarity NPC471219
0.7159 Intermediate Similarity NPC131813
0.7158 Intermediate Similarity NPC470906
0.7143 Intermediate Similarity NPC170394
0.7143 Intermediate Similarity NPC44083
0.7143 Intermediate Similarity NPC476177
0.7143 Intermediate Similarity NPC72845
0.7143 Intermediate Similarity NPC153987
0.7126 Intermediate Similarity NPC318515
0.7126 Intermediate Similarity NPC139566
0.7126 Intermediate Similarity NPC470812
0.7111 Intermediate Similarity NPC73995
0.7111 Intermediate Similarity NPC50488
0.7111 Intermediate Similarity NPC50070
0.7111 Intermediate Similarity NPC474396
0.7108 Intermediate Similarity NPC189206
0.7108 Intermediate Similarity NPC470751
0.7108 Intermediate Similarity NPC283619
0.7108 Intermediate Similarity NPC472300
0.7108 Intermediate Similarity NPC470750
0.7097 Intermediate Similarity NPC274417
0.7093 Intermediate Similarity NPC286786
0.7093 Intermediate Similarity NPC471218
0.7093 Intermediate Similarity NPC200513
0.7093 Intermediate Similarity NPC70479
0.7079 Intermediate Similarity NPC30421
0.7079 Intermediate Similarity NPC471728
0.7073 Intermediate Similarity NPC32832
0.7065 Intermediate Similarity NPC38232
0.7065 Intermediate Similarity NPC7349
0.7059 Intermediate Similarity NPC281880
0.7059 Intermediate Similarity NPC474956
0.7059 Intermediate Similarity NPC469637
0.7059 Intermediate Similarity NPC269791
0.7059 Intermediate Similarity NPC476809
0.7053 Intermediate Similarity NPC278673
0.7051 Intermediate Similarity NPC474477
0.7045 Intermediate Similarity NPC241512
0.7045 Intermediate Similarity NPC323765
0.7045 Intermediate Similarity NPC280203
0.7045 Intermediate Similarity NPC476602
0.7045 Intermediate Similarity NPC6185
0.7045 Intermediate Similarity NPC189311
0.7045 Intermediate Similarity NPC472442
0.7041 Intermediate Similarity NPC165969
0.7037 Intermediate Similarity NPC144947
0.7033 Intermediate Similarity NPC152467
0.7033 Intermediate Similarity NPC475823
0.7033 Intermediate Similarity NPC8062
0.7033 Intermediate Similarity NPC474209
0.7033 Intermediate Similarity NPC78973
0.7033 Intermediate Similarity NPC191684
0.7033 Intermediate Similarity NPC310479
0.7024 Intermediate Similarity NPC285761
0.7024 Intermediate Similarity NPC184737
0.7021 Intermediate Similarity NPC29952
0.7021 Intermediate Similarity NPC209297
0.7021 Intermediate Similarity NPC260796
0.7021 Intermediate Similarity NPC16967
0.7021 Intermediate Similarity NPC475380
0.7021 Intermediate Similarity NPC73858
0.7011 Intermediate Similarity NPC79945
0.7011 Intermediate Similarity NPC311070
0.7011 Intermediate Similarity NPC132386
0.7011 Intermediate Similarity NPC307258
0.7011 Intermediate Similarity NPC22611
0.7 Intermediate Similarity NPC80335
0.7 Intermediate Similarity NPC224145
0.7 Intermediate Similarity NPC226863
0.7 Intermediate Similarity NPC473229
0.7 Intermediate Similarity NPC472302
0.7 Intermediate Similarity NPC474845
0.7 Intermediate Similarity NPC474925
0.6989 Remote Similarity NPC57117
0.6989 Remote Similarity NPC477130
0.6989 Remote Similarity NPC140277
0.6989 Remote Similarity NPC477129
0.6989 Remote Similarity NPC201725
0.6989 Remote Similarity NPC105490
0.6989 Remote Similarity NPC191521
0.6988 Remote Similarity NPC470749
0.6988 Remote Similarity NPC41017
0.6988 Remote Similarity NPC92489
0.6988 Remote Similarity NPC469796
0.6988 Remote Similarity NPC250621
0.6988 Remote Similarity NPC469793
0.6979 Remote Similarity NPC35751
0.6977 Remote Similarity NPC108476
0.6977 Remote Similarity NPC149237
0.6977 Remote Similarity NPC159148
0.6977 Remote Similarity NPC142163
0.6966 Remote Similarity NPC195640
0.6966 Remote Similarity NPC286153
0.6966 Remote Similarity NPC179591
0.6966 Remote Similarity NPC474970
0.6966 Remote Similarity NPC470345
0.6966 Remote Similarity NPC475069
0.6966 Remote Similarity NPC175145
0.6962 Remote Similarity NPC155198
0.6962 Remote Similarity NPC476945
0.6962 Remote Similarity NPC94192
0.6957 Remote Similarity NPC473675
0.6957 Remote Similarity NPC49420
0.6957 Remote Similarity NPC329842
0.6957 Remote Similarity NPC252433
0.6951 Remote Similarity NPC71152
0.6951 Remote Similarity NPC238146
0.6947 Remote Similarity NPC311241
0.6947 Remote Similarity NPC475446
0.6941 Remote Similarity NPC273410
0.6941 Remote Similarity NPC80530
0.6941 Remote Similarity NPC100906
0.6939 Remote Similarity NPC176883
0.6932 Remote Similarity NPC33913
0.6932 Remote Similarity NPC472265
0.6932 Remote Similarity NPC251170
0.6932 Remote Similarity NPC15534
0.6923 Remote Similarity NPC262858
0.6923 Remote Similarity NPC472983
0.6923 Remote Similarity NPC119416
0.6923 Remote Similarity NPC327815
0.6923 Remote Similarity NPC472240
0.6923 Remote Similarity NPC469546
0.6923 Remote Similarity NPC177141
0.6915 Remote Similarity NPC13924
0.6915 Remote Similarity NPC276110
0.6915 Remote Similarity NPC472441
0.6914 Remote Similarity NPC5734
0.6914 Remote Similarity NPC164022
0.6907 Remote Similarity NPC168319
0.6907 Remote Similarity NPC475767
0.6907 Remote Similarity NPC119467

  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 NPC219809 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 NPD4195 Approved
0.7093 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD3573 Approved
0.6966 Remote Similarity NPD7146 Approved
0.6966 Remote Similarity NPD7334 Approved
0.6966 Remote Similarity NPD3618 Phase 1
0.6966 Remote Similarity NPD6684 Approved
0.6966 Remote Similarity NPD5330 Approved
0.6966 Remote Similarity NPD7521 Approved
0.6966 Remote Similarity NPD6409 Approved
0.6915 Remote Similarity NPD6356 Clinical (unspecified phase)
0.686 Remote Similarity NPD7525 Registered
0.6854 Remote Similarity NPD1694 Approved
0.6813 Remote Similarity NPD5737 Approved
0.6813 Remote Similarity NPD6672 Approved
0.6813 Remote Similarity NPD6903 Approved
0.6813 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6809 Remote Similarity NPD6001 Approved
0.6778 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6079 Approved
0.6744 Remote Similarity NPD7645 Phase 2
0.6742 Remote Similarity NPD3133 Approved
0.6742 Remote Similarity NPD3666 Approved
0.6742 Remote Similarity NPD3665 Phase 1
0.6739 Remote Similarity NPD5328 Approved
0.6705 Remote Similarity NPD4223 Phase 3
0.6705 Remote Similarity NPD4221 Approved
0.6702 Remote Similarity NPD4202 Approved
0.6701 Remote Similarity NPD4225 Approved
0.6667 Remote Similarity NPD4695 Discontinued
0.6667 Remote Similarity NPD4697 Phase 3
0.6632 Remote Similarity NPD7748 Approved
0.6632 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6632 Remote Similarity NPD7900 Approved
0.663 Remote Similarity NPD5208 Approved
0.6588 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6585 Remote Similarity NPD4691 Approved
0.6559 Remote Similarity NPD6051 Approved
0.6559 Remote Similarity NPD6080 Approved
0.6559 Remote Similarity NPD4753 Phase 2
0.6559 Remote Similarity NPD6904 Approved
0.6559 Remote Similarity NPD6673 Approved
0.6556 Remote Similarity NPD4197 Approved
0.6548 Remote Similarity NPD6926 Approved
0.6548 Remote Similarity NPD6924 Approved
0.6531 Remote Similarity NPD7638 Approved
0.6517 Remote Similarity NPD3667 Approved
0.6506 Remote Similarity NPD4243 Approved
0.6495 Remote Similarity NPD5222 Approved
0.6495 Remote Similarity NPD5221 Approved
0.6495 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6489 Remote Similarity NPD5207 Approved
0.6484 Remote Similarity NPD5329 Approved
0.6471 Remote Similarity NPD7339 Approved
0.6471 Remote Similarity NPD6942 Approved
0.6471 Remote Similarity NPD6008 Approved
0.6465 Remote Similarity NPD7639 Approved
0.6465 Remote Similarity NPD5285 Approved
0.6465 Remote Similarity NPD4696 Approved
0.6465 Remote Similarity NPD5286 Approved
0.6465 Remote Similarity NPD7640 Approved
0.6463 Remote Similarity NPD4137 Phase 3
0.6444 Remote Similarity NPD4788 Approved
0.6437 Remote Similarity NPD3617 Approved
0.6429 Remote Similarity NPD6083 Phase 2
0.6429 Remote Similarity NPD7902 Approved
0.6429 Remote Similarity NPD4755 Approved
0.6429 Remote Similarity NPD5173 Approved
0.6429 Remote Similarity NPD6084 Phase 2
0.6421 Remote Similarity NPD7515 Phase 2
0.6421 Remote Similarity NPD5693 Phase 1
0.6413 Remote Similarity NPD6098 Approved
0.6413 Remote Similarity NPD4138 Approved
0.6413 Remote Similarity NPD4690 Approved
0.6413 Remote Similarity NPD4693 Phase 3
0.6413 Remote Similarity NPD4689 Approved
0.6413 Remote Similarity NPD4519 Discontinued
0.6413 Remote Similarity NPD5690 Phase 2
0.6413 Remote Similarity NPD5205 Approved
0.6413 Remote Similarity NPD4688 Approved
0.6413 Remote Similarity NPD4623 Approved
0.6408 Remote Similarity NPD5697 Approved
0.64 Remote Similarity NPD5223 Approved
0.6395 Remote Similarity NPD6933 Approved
0.6392 Remote Similarity NPD5695 Phase 3
0.6392 Remote Similarity NPD5210 Approved
0.6392 Remote Similarity NPD4629 Approved
0.6386 Remote Similarity NPD4747 Approved
0.6374 Remote Similarity NPD4786 Approved
0.6374 Remote Similarity NPD3668 Phase 3
0.6364 Remote Similarity NPD5290 Discontinued
0.6364 Remote Similarity NPD5696 Approved
0.6353 Remote Similarity NPD4784 Approved
0.6353 Remote Similarity NPD4785 Approved
0.6353 Remote Similarity NPD4058 Approved
0.6346 Remote Similarity NPD6899 Approved
0.6346 Remote Similarity NPD6011 Approved
0.6346 Remote Similarity NPD6881 Approved
0.6337 Remote Similarity NPD5224 Approved
0.6337 Remote Similarity NPD4633 Approved
0.6337 Remote Similarity NPD5226 Approved
0.6337 Remote Similarity NPD5211 Phase 2
0.6337 Remote Similarity NPD5225 Approved
0.6316 Remote Similarity NPD5692 Phase 3
0.6311 Remote Similarity NPD5739 Approved
0.6311 Remote Similarity NPD6402 Approved
0.6311 Remote Similarity NPD6675 Approved
0.6311 Remote Similarity NPD7128 Approved
0.63 Remote Similarity NPD4700 Approved
0.6292 Remote Similarity NPD7509 Discontinued
0.6286 Remote Similarity NPD6014 Approved
0.6286 Remote Similarity NPD6013 Approved
0.6286 Remote Similarity NPD6012 Approved
0.6279 Remote Similarity NPD4190 Phase 3
0.6279 Remote Similarity NPD5275 Approved
0.6275 Remote Similarity NPD5174 Approved
0.6275 Remote Similarity NPD5175 Approved
0.6264 Remote Similarity NPD6695 Phase 3
0.625 Remote Similarity NPD5701 Approved
0.625 Remote Similarity NPD5694 Approved
0.625 Remote Similarity NPD6050 Approved
0.6237 Remote Similarity NPD4694 Approved
0.6237 Remote Similarity NPD5280 Approved
0.6237 Remote Similarity NPD5279 Phase 3
0.6226 Remote Similarity NPD7290 Approved
0.6226 Remote Similarity NPD7102 Approved
0.6226 Remote Similarity NPD6883 Approved
0.6214 Remote Similarity NPD5141 Approved
0.6196 Remote Similarity NPD7338 Clinical (unspecified phase)
0.619 Remote Similarity NPD7320 Approved
0.6186 Remote Similarity NPD6399 Phase 3
0.6168 Remote Similarity NPD6617 Approved
0.6168 Remote Similarity NPD6649 Approved
0.6168 Remote Similarity NPD6869 Approved
0.6168 Remote Similarity NPD6847 Approved
0.6168 Remote Similarity NPD6650 Approved
0.6168 Remote Similarity NPD8130 Phase 1
0.6132 Remote Similarity NPD6372 Approved
0.6132 Remote Similarity NPD6373 Approved
0.6122 Remote Similarity NPD5282 Discontinued
0.6117 Remote Similarity NPD4754 Approved
0.6111 Remote Similarity NPD6931 Approved
0.6111 Remote Similarity NPD6930 Phase 2
0.6111 Remote Similarity NPD6882 Approved
0.6111 Remote Similarity NPD8297 Approved
0.6076 Remote Similarity NPD1145 Discontinued
0.6071 Remote Similarity NPD6923 Approved
0.6071 Remote Similarity NPD6922 Approved
0.6038 Remote Similarity NPD4729 Approved
0.6038 Remote Similarity NPD4730 Approved
0.6038 Remote Similarity NPD5128 Approved
0.6019 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6 Remote Similarity NPD7144 Approved
0.6 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6 Remote Similarity NPD7750 Discontinued
0.6 Remote Similarity NPD4767 Approved
0.6 Remote Similarity NPD7524 Approved
0.6 Remote Similarity NPD7143 Approved
0.6 Remote Similarity NPD4768 Approved
0.6 Remote Similarity NPD6929 Approved
0.5977 Remote Similarity NPD4687 Approved
0.5977 Remote Similarity NPD5733 Approved
0.5976 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5965 Remote Similarity NPD7503 Approved
0.5962 Remote Similarity NPD6052 Approved
0.596 Remote Similarity NPD5707 Approved
0.5957 Remote Similarity NPD1696 Phase 3
0.5957 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5955 Remote Similarity NPD6932 Approved
0.5952 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5946 Remote Similarity NPD6274 Approved
0.5934 Remote Similarity NPD4748 Discontinued
0.593 Remote Similarity NPD7152 Approved
0.593 Remote Similarity NPD7151 Approved
0.593 Remote Similarity NPD5276 Approved
0.593 Remote Similarity NPD7150 Approved
0.5926 Remote Similarity NPD5169 Approved
0.5926 Remote Similarity NPD5248 Approved
0.5926 Remote Similarity NPD5249 Phase 3
0.5926 Remote Similarity NPD4634 Approved
0.5926 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5926 Remote Similarity NPD5250 Approved
0.5926 Remote Similarity NPD5247 Approved
0.5926 Remote Similarity NPD5135 Approved
0.5926 Remote Similarity NPD5251 Approved
0.5918 Remote Similarity NPD5284 Approved
0.5918 Remote Similarity NPD5281 Approved
0.5918 Remote Similarity NPD8034 Phase 2
0.5918 Remote Similarity NPD8035 Phase 2
0.5909 Remote Similarity NPD4632 Approved
0.59 Remote Similarity NPD5654 Approved
0.5893 Remote Similarity NPD7115 Discovery
0.5893 Remote Similarity NPD6317 Approved
0.5889 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5888 Remote Similarity NPD5168 Approved
0.5877 Remote Similarity NPD6054 Approved
0.5876 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5872 Remote Similarity NPD5127 Approved
0.5872 Remote Similarity NPD5215 Approved
0.5872 Remote Similarity NPD5217 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