Structure

Physi-Chem Properties

Molecular Weight:  200.08
Volume:  218.053
LogP:  2.652
LogD:  2.137
LogS:  -3.247
# Rotatable Bonds:  2
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.686
Synthetic Accessibility Score:  2.968
Fsp3:  0.154
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.574
MDCK Permeability:  1.8226292013423517e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.025
30% Bioavailability (F30%):  0.664

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.827
Plasma Protein Binding (PPB):  95.09435272216797%
Volume Distribution (VD):  0.779
Pgp-substrate:  4.225221633911133%

ADMET: Metabolism

CYP1A2-inhibitor:  0.977
CYP1A2-substrate:  0.121
CYP2C19-inhibitor:  0.911
CYP2C19-substrate:  0.228
CYP2C9-inhibitor:  0.58
CYP2C9-substrate:  0.929
CYP2D6-inhibitor:  0.167
CYP2D6-substrate:  0.713
CYP3A4-inhibitor:  0.545
CYP3A4-substrate:  0.239

ADMET: Excretion

Clearance (CL):  4.198
Half-life (T1/2):  0.769

ADMET: Toxicity

hERG Blockers:  0.049
Human Hepatotoxicity (H-HT):  0.902
Drug-inuced Liver Injury (DILI):  0.35
AMES Toxicity:  0.682
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.917
Skin Sensitization:  0.958
Carcinogencity:  0.284
Eye Corrosion:  0.481
Eye Irritation:  0.973
Respiratory Toxicity:  0.907

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  Natural Product: NPC127491

Natural Product ID:  NPC127491
Common Name*:   Goniothalamin
IUPAC Name:   (2R)-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one
Synonyms:   (R)-(+)-Goniothalamin; (R)-Goniothalamin; Goniothalamin
Standard InCHIKey:  RLGHFVLWYYVMQZ-BZYZDCJZSA-N
Standard InCHI:  InChI=1S/C13H12O2/c14-13-8-4-7-12(15-13)10-9-11-5-2-1-3-6-11/h1-6,8-10,12H,7H2/b10-9+/t12-/m1/s1
SMILES:  c1ccc(cc1)/C=C/[C@H]1CC=CC(=O)O1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464443
PubChem CID:   6440856
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000037] Styrenes

*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
NPO2253 Illicium jiadifengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[11975494]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota Roots n.a. n.a. PMID[14510592]
NPO21404 Anagallis monelli Species Primulaceae Eukaryota n.a. aerial part n.a. PMID[17329877]
NPO2558 Ceratodictyon spongiosum Species Lomentariaceae Eukaryota n.a. n.a. n.a. PMID[19670881]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[3572418]
NPO7761 Laurencia majuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[8691206]
NPO26455 Merwilla natalensis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO7450 Sida acuta Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1536 Lindera triloba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7761 Laurencia majuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3409 Goniothalamus leiocarpus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1093 Plumeria obtusa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7450 Sida acuta Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4366 Hura crepitans Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2253 Illicium jiadifengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2182 Athyrium filix-femina Species Athyriaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7761 Laurencia majuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1536 Lindera triloba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3409 Goniothalamus leiocarpus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7607 Ophiorrhiza pumila Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3409 Goniothalamus leiocarpus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7450 Sida acuta Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1536 Lindera triloba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4805 Balanophora papuana Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8060 Lethariella cashmeriana Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4366 Hura crepitans Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20329 Gymnacranthera paniculata Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11236 Mycale mytilorum Species Mycalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7589 Baccharis spartioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO95 Streptomyces ambofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5379 Cortinarius sanguineus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10517 Aconitum vilmorini Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7761 Laurencia majuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2885 Erechtites quadridentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO274 Dendrobates viridis Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21404 Anagallis monelli Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1878 Kunzea baxteri Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27877 Eliokarmos thyrsoides Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2253 Illicium jiadifengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7607 Ophiorrhiza pumila Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1693 Gnomonia fragariae Species Sydowiellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2956 Echinometra oblonga Species Echinometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14597 Prociphilus tessellatus Species Pemphigidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11725 Cetonia aurata Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1093 Plumeria obtusa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7450 Sida acuta Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26455 Merwilla natalensis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3409 Goniothalamus leiocarpus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5796 Haplopappus foliosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4276 Cupressus lindleyi Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3114 Stylocheilus striatus Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13768 Swertia marginata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5262 Sargassum natans Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6838 Senecio grisebachii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9769 Mortonia palmeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1366 Piptothrix areolare n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15053 Menispermum cocculus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2558 Ceratodictyon spongiosum Species Lomentariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2182 Athyrium filix-femina Species Athyriaceae 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
NPT306 Cell Line PC-3 Homo sapiens IC50 = 4000.0 nM PMID[523003]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 19000.0 nM PMID[523003]
NPT858 Cell Line LNCaP Homo sapiens IC50 = 12000.0 nM PMID[523003]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 28000.0 nM PMID[523003]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 1460.0 nM PMID[523004]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 4500.0 nM PMID[523005]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 1600.0 nM PMID[523005]
NPT168 Cell Line P388 Mus musculus IC50 = 3800.0 nM PMID[523005]
NPT3470 Cell Line WEHI-164 Mus musculus IC50 = 8500.0 nM PMID[523005]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 5400.0 nM PMID[523005]
NPT398 Cell Line UACC-62 Homo sapiens TGI = 21560.0 nM PMID[523006]
NPT83 Cell Line MCF7 Homo sapiens TGI = 21680.0 nM PMID[523006]
NPT401 Cell Line 786-0 Homo sapiens TGI = 18570.0 nM PMID[523006]
NPT397 Cell Line NCI-H460 Homo sapiens TGI = 32360.0 nM PMID[523006]
NPT377 Cell Line OVCAR-3 Homo sapiens TGI = 8310.0 nM PMID[523006]
NPT139 Cell Line HT-29 Homo sapiens TGI = 21980.0 nM PMID[523006]
NPT380 Cell Line U-251 Homo sapiens TGI = 13370.0 nM PMID[523006]
NPT380 Cell Line U-251 Homo sapiens GI = 13.7 uM PMID[523007]
NPT83 Cell Line MCF7 Homo sapiens GI = 12.7 uM PMID[523007]
NPT401 Cell Line 786-0 Homo sapiens GI = 14.8 uM PMID[523007]
NPT397 Cell Line NCI-H460 Homo sapiens GI = 13.6 uM PMID[523007]
NPT377 Cell Line OVCAR-3 Homo sapiens GI = 14.2 uM PMID[523007]
NPT139 Cell Line HT-29 Homo sapiens GI = 13.9 uM PMID[523007]
NPT941 Cell Line HaCaT Homo sapiens GI = 27.7 uM PMID[523007]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 34200.0 nM PMID[523008]
NPT111 Cell Line K562 Homo sapiens TGI = 926800.0 nM PMID[523009]
NPT398 Cell Line UACC-62 Homo sapiens TGI = 17400.0 nM PMID[523009]
NPT401 Cell Line 786-0 Homo sapiens TGI = 13900.0 nM PMID[523009]
NPT941 Cell Line HaCaT Homo sapiens TGI = 13400.0 nM PMID[523009]
NPT83 Cell Line MCF7 Homo sapiens TGI = 11200.0 nM PMID[523009]
NPT139 Cell Line HT-29 Homo sapiens TGI = 10000.0 nM PMID[523009]
NPT380 Cell Line U-251 Homo sapiens TGI = 9800.0 nM PMID[523009]
NPT306 Cell Line PC-3 Homo sapiens TGI = 9600.0 nM PMID[523009]
NPT941 Cell Line HaCaT Homo sapiens IC50 = 28600.0 nM PMID[523011]
NPT81 Cell Line A549 Homo sapiens IC50 = 5700.0 nM PMID[523012]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 55500.0 nM PMID[523012]
NPT1723 Cell Line HBL-100 Homo sapiens IC50 = 20900.0 nM PMID[523012]
NPT4115 Individual Protein Exportin-1 Homo sapiens Inhibition = 50.0 % PMID[523013]
NPT4115 Individual Protein Exportin-1 Homo sapiens Inhibition = 100.0 % PMID[523013]
NPT4115 Individual Protein Exportin-1 Homo sapiens Inhibition = 0.0 % PMID[523013]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 1600.0 nM PMID[523014]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 625.0 nM PMID[523014]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 5400.0 nM PMID[523005]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TGI = 1200.0 nM PMID[523006]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TGI = 13470.0 nM PMID[523006]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 37.4 % PMID[523006]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 21.9 % PMID[523006]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 25.3 % PMID[523006]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI = 8.0 uM PMID[523007]
NPT2 Others Unspecified IC50 = 27400.0 nM PMID[523008]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TGI = 14500.0 nM PMID[523009]
NPT983 Protein Complex Nuclear factor NF-kappa-B complex Homo sapiens IC50 = 7000.0 nM PMID[523010]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 65000.0 nM PMID[523011]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 70.0 % PMID[523011]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 50.0 % PMID[523011]
NPT27 Others Unspecified Ratio IC50 = 0.44 n.a. PMID[523011]
NPT2 Others Unspecified Activity = 24.3 % PMID[523012]
NPT2 Others Unspecified Activity = 30.0 % PMID[523012]
NPT2 Others Unspecified Activity = 71.7 % PMID[523012]
NPT2 Others Unspecified Activity = -2.0 % PMID[523012]
NPT2 Others Unspecified Activity = 10.0 % PMID[523012]
NPT2 Others Unspecified Activity = 60.0 % PMID[523012]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens IC50 = 5400.0 nM PMID[523014]

☑ 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 NPC127491 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 NPC308619
1.0 High Similarity NPC324835
0.9487 High Similarity NPC89950
0.9351 High Similarity NPC176228
0.9268 High Similarity NPC169050
0.9268 High Similarity NPC286608
0.9241 High Similarity NPC71795
0.9231 High Similarity NPC78517
0.9231 High Similarity NPC167577
0.9125 High Similarity NPC99240
0.9059 High Similarity NPC472319
0.9012 High Similarity NPC208183
0.9012 High Similarity NPC243289
0.9 High Similarity NPC303245
0.8974 High Similarity NPC287790
0.8974 High Similarity NPC3672
0.8953 High Similarity NPC77273
0.8846 High Similarity NPC175393
0.8795 High Similarity NPC53299
0.8636 High Similarity NPC23453
0.8588 High Similarity NPC96625
0.8506 High Similarity NPC240108
0.8506 High Similarity NPC213156
0.8409 Intermediate Similarity NPC119631
0.8391 Intermediate Similarity NPC173443
0.837 Intermediate Similarity NPC98911
0.837 Intermediate Similarity NPC472318
0.8276 Intermediate Similarity NPC304760
0.825 Intermediate Similarity NPC32203
0.825 Intermediate Similarity NPC206800
0.814 Intermediate Similarity NPC58616
0.8105 Intermediate Similarity NPC234305
0.8021 Intermediate Similarity NPC171831
0.8021 Intermediate Similarity NPC85977
0.8021 Intermediate Similarity NPC280616
0.8021 Intermediate Similarity NPC242913
0.7955 Intermediate Similarity NPC89377
0.7952 Intermediate Similarity NPC50192
0.7889 Intermediate Similarity NPC185501
0.7872 Intermediate Similarity NPC135951
0.7872 Intermediate Similarity NPC154517
0.7857 Intermediate Similarity NPC472316
0.7857 Intermediate Similarity NPC472315
0.7857 Intermediate Similarity NPC475203
0.7857 Intermediate Similarity NPC474376
0.7857 Intermediate Similarity NPC136962
0.7857 Intermediate Similarity NPC37115
0.7857 Intermediate Similarity NPC170484
0.7848 Intermediate Similarity NPC16190
0.7848 Intermediate Similarity NPC235059
0.7848 Intermediate Similarity NPC169222
0.7789 Intermediate Similarity NPC80115
0.7789 Intermediate Similarity NPC118343
0.7778 Intermediate Similarity NPC220893
0.7778 Intermediate Similarity NPC20485
0.7778 Intermediate Similarity NPC475465
0.7778 Intermediate Similarity NPC472314
0.7778 Intermediate Similarity NPC277788
0.7778 Intermediate Similarity NPC47536
0.7766 Intermediate Similarity NPC270654
0.7766 Intermediate Similarity NPC276775
0.7766 Intermediate Similarity NPC92754
0.7766 Intermediate Similarity NPC249912
0.7765 Intermediate Similarity NPC121800
0.7732 Intermediate Similarity NPC82426
0.7732 Intermediate Similarity NPC91820
0.7727 Intermediate Similarity NPC475710
0.7722 Intermediate Similarity NPC311343
0.7708 Intermediate Similarity NPC42211
0.77 Intermediate Similarity NPC40178
0.7684 Intermediate Similarity NPC78701
0.7684 Intermediate Similarity NPC35448
0.7684 Intermediate Similarity NPC225060
0.7677 Intermediate Similarity NPC51174
0.7677 Intermediate Similarity NPC477251
0.766 Intermediate Similarity NPC30361
0.7654 Intermediate Similarity NPC155429
0.7654 Intermediate Similarity NPC326200
0.7625 Intermediate Similarity NPC98880
0.7614 Intermediate Similarity NPC44546
0.7604 Intermediate Similarity NPC146351
0.7586 Intermediate Similarity NPC103387
0.7586 Intermediate Similarity NPC323103
0.7579 Intermediate Similarity NPC325499
0.7553 Intermediate Similarity NPC5472
0.7553 Intermediate Similarity NPC130398
0.7551 Intermediate Similarity NPC301943
0.7551 Intermediate Similarity NPC179686
0.7551 Intermediate Similarity NPC304638
0.7551 Intermediate Similarity NPC474365
0.7549 Intermediate Similarity NPC474157
0.7531 Intermediate Similarity NPC95289
0.7526 Intermediate Similarity NPC70624
0.75 Intermediate Similarity NPC270507
0.7476 Intermediate Similarity NPC234376
0.7475 Intermediate Similarity NPC109637
0.7475 Intermediate Similarity NPC114594
0.7471 Intermediate Similarity NPC165212
0.7426 Intermediate Similarity NPC260952
0.7423 Intermediate Similarity NPC325497
0.7412 Intermediate Similarity NPC179726
0.7404 Intermediate Similarity NPC272524
0.7404 Intermediate Similarity NPC265002
0.74 Intermediate Similarity NPC269457
0.74 Intermediate Similarity NPC127676
0.74 Intermediate Similarity NPC128730
0.74 Intermediate Similarity NPC209632
0.74 Intermediate Similarity NPC472919
0.7374 Intermediate Similarity NPC60679
0.7353 Intermediate Similarity NPC114741
0.7353 Intermediate Similarity NPC469636
0.7353 Intermediate Similarity NPC206341
0.7353 Intermediate Similarity NPC184633
0.7353 Intermediate Similarity NPC182549
0.7353 Intermediate Similarity NPC265407
0.7353 Intermediate Similarity NPC474364
0.7353 Intermediate Similarity NPC83628
0.7347 Intermediate Similarity NPC253746
0.7333 Intermediate Similarity NPC308744
0.7333 Intermediate Similarity NPC294134
0.7327 Intermediate Similarity NPC176971
0.7327 Intermediate Similarity NPC326447
0.7308 Intermediate Similarity NPC158282
0.7284 Intermediate Similarity NPC78954
0.7284 Intermediate Similarity NPC82770
0.7284 Intermediate Similarity NPC239931
0.7282 Intermediate Similarity NPC149545
0.7273 Intermediate Similarity NPC188895
0.7273 Intermediate Similarity NPC94343
0.7264 Intermediate Similarity NPC474685
0.7255 Intermediate Similarity NPC151530
0.7255 Intermediate Similarity NPC157473
0.7245 Intermediate Similarity NPC203925
0.7245 Intermediate Similarity NPC171843
0.7241 Intermediate Similarity NPC469894
0.7238 Intermediate Similarity NPC474176
0.7238 Intermediate Similarity NPC128368
0.7228 Intermediate Similarity NPC139891
0.7212 Intermediate Similarity NPC476003
0.7212 Intermediate Similarity NPC323007
0.7212 Intermediate Similarity NPC43584
0.7212 Intermediate Similarity NPC210089
0.7212 Intermediate Similarity NPC183700
0.7209 Intermediate Similarity NPC329318
0.7204 Intermediate Similarity NPC9822
0.72 Intermediate Similarity NPC89886
0.7196 Intermediate Similarity NPC473507
0.7196 Intermediate Similarity NPC149691
0.7191 Intermediate Similarity NPC106313
0.7184 Intermediate Similarity NPC99846
0.7184 Intermediate Similarity NPC269023
0.7174 Intermediate Similarity NPC194326
0.7157 Intermediate Similarity NPC119271
0.7143 Intermediate Similarity NPC179411
0.7143 Intermediate Similarity NPC470825
0.7143 Intermediate Similarity NPC139946
0.7143 Intermediate Similarity NPC474314
0.7143 Intermediate Similarity NPC185840
0.7129 Intermediate Similarity NPC269644
0.7129 Intermediate Similarity NPC2518
0.7128 Intermediate Similarity NPC108026
0.7128 Intermediate Similarity NPC26224
0.7126 Intermediate Similarity NPC76455
0.7126 Intermediate Similarity NPC137847
0.7115 Intermediate Similarity NPC273837
0.7111 Intermediate Similarity NPC288903
0.7103 Intermediate Similarity NPC210092
0.7087 Intermediate Similarity NPC56493
0.7083 Intermediate Similarity NPC261181
0.7079 Intermediate Similarity NPC73978
0.7075 Intermediate Similarity NPC161611
0.7065 Intermediate Similarity NPC318107
0.7059 Intermediate Similarity NPC288760
0.7059 Intermediate Similarity NPC227255
0.7053 Intermediate Similarity NPC475023
0.7053 Intermediate Similarity NPC475059
0.7048 Intermediate Similarity NPC167504
0.7045 Intermediate Similarity NPC300205
0.7045 Intermediate Similarity NPC139901
0.7045 Intermediate Similarity NPC151405
0.7041 Intermediate Similarity NPC289201
0.7037 Intermediate Similarity NPC476476
0.7037 Intermediate Similarity NPC100353
0.7019 Intermediate Similarity NPC10251
0.7019 Intermediate Similarity NPC281604
0.7019 Intermediate Similarity NPC17417
0.7011 Intermediate Similarity NPC245966
0.701 Intermediate Similarity NPC32977
0.701 Intermediate Similarity NPC473347
0.701 Intermediate Similarity NPC81010
0.7009 Intermediate Similarity NPC87069
0.7009 Intermediate Similarity NPC474363
0.7009 Intermediate Similarity NPC307651
0.7009 Intermediate Similarity NPC474641
0.7 Intermediate Similarity NPC13755
0.699 Remote Similarity NPC37622
0.699 Remote Similarity NPC30594
0.6981 Remote Similarity NPC79496
0.6981 Remote Similarity NPC477250
0.6979 Remote Similarity NPC475057

  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 NPC127491 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
0.9268 High Similarity NPD1282 Approved
0.825 Intermediate Similarity NPD9716 Approved
0.8182 Intermediate Similarity NPD689 Discontinued
0.7789 Intermediate Similarity NPD1238 Approved
0.75 Intermediate Similarity NPD3971 Phase 1
0.75 Intermediate Similarity NPD5926 Approved
0.7327 Intermediate Similarity NPD3134 Approved
0.7255 Intermediate Similarity NPD1358 Approved
0.7228 Intermediate Similarity NPD9697 Approved
0.7212 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6647 Phase 2
0.7143 Intermediate Similarity NPD5734 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD5909 Discontinued
0.7115 Intermediate Similarity NPD2067 Discontinued
0.7083 Intermediate Similarity NPD1202 Approved
0.7065 Intermediate Similarity NPD9257 Approved
0.7065 Intermediate Similarity NPD9259 Approved
0.7019 Intermediate Similarity NPD2182 Approved
0.6981 Remote Similarity NPD969 Suspended
0.6961 Remote Similarity NPD164 Approved
0.6932 Remote Similarity NPD227 Approved
0.6932 Remote Similarity NPD225 Approved
0.6889 Remote Similarity NPD942 Approved
0.6854 Remote Similarity NPD9490 Approved
0.68 Remote Similarity NPD9495 Approved
0.6778 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6771 Remote Similarity NPD3672 Approved
0.6771 Remote Similarity NPD3673 Approved
0.6771 Remote Similarity NPD9258 Approved
0.6771 Remote Similarity NPD9256 Approved
0.6768 Remote Similarity NPD1989 Approved
0.6739 Remote Similarity NPD9491 Approved
0.6733 Remote Similarity NPD7798 Approved
0.6703 Remote Similarity NPD226 Approved
0.6667 Remote Similarity NPD6049 Phase 2
0.6667 Remote Similarity NPD694 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6048 Clinical (unspecified phase)
0.6635 Remote Similarity NPD1237 Approved
0.6632 Remote Similarity NPD650 Approved
0.6629 Remote Similarity NPD9294 Approved
0.6571 Remote Similarity NPD5048 Discontinued
0.6569 Remote Similarity NPD2066 Phase 3
0.6566 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6549 Remote Similarity NPD9545 Approved
0.6545 Remote Similarity NPD1241 Discontinued
0.6545 Remote Similarity NPD6010 Discontinued
0.6538 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6514 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6509 Remote Similarity NPD5705 Approved
0.6509 Remote Similarity NPD5704 Approved
0.6509 Remote Similarity NPD5706 Approved
0.6505 Remote Similarity NPD2555 Approved
0.6505 Remote Similarity NPD2550 Approved
0.6505 Remote Similarity NPD2549 Approved
0.6505 Remote Similarity NPD2558 Approved
0.6505 Remote Similarity NPD2553 Approved
0.6505 Remote Similarity NPD2552 Approved
0.65 Remote Similarity NPD9260 Approved
0.6486 Remote Similarity NPD690 Clinical (unspecified phase)
0.6481 Remote Similarity NPD5235 Approved
0.6481 Remote Similarity NPD5240 Approved
0.6481 Remote Similarity NPD5237 Approved
0.6481 Remote Similarity NPD5236 Approved
0.6481 Remote Similarity NPD5239 Approved
0.646 Remote Similarity NPD2347 Approved
0.6458 Remote Similarity NPD1087 Approved
0.6442 Remote Similarity NPD4188 Approved
0.6442 Remote Similarity NPD4189 Approved
0.6441 Remote Similarity NPD2198 Approved
0.6441 Remote Similarity NPD2199 Approved
0.6429 Remote Similarity NPD4198 Discontinued
0.6422 Remote Similarity NPD2201 Approved
0.641 Remote Similarity NPD6637 Approved
0.6386 Remote Similarity NPD675 Discontinued
0.6381 Remote Similarity NPD1929 Approved
0.6381 Remote Similarity NPD1930 Approved
0.6381 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6372 Remote Similarity NPD9493 Approved
0.6364 Remote Similarity NPD7609 Phase 3
0.6364 Remote Similarity NPD1239 Approved
0.6348 Remote Similarity NPD5691 Approved
0.6344 Remote Similarity NPD9250 Approved
0.6339 Remote Similarity NPD2629 Approved
0.6327 Remote Similarity NPD800 Approved
0.6325 Remote Similarity NPD6287 Discontinued
0.6321 Remote Similarity NPD3046 Approved
0.6321 Remote Similarity NPD3047 Approved
0.6321 Remote Similarity NPD3048 Approved
0.6311 Remote Similarity NPD5454 Clinical (unspecified phase)
0.6306 Remote Similarity NPD5535 Approved
0.6306 Remote Similarity NPD6858 Approved
0.6306 Remote Similarity NPD7094 Approved
0.63 Remote Similarity NPD1508 Approved
0.63 Remote Similarity NPD7631 Approved
0.6289 Remote Similarity NPD4793 Discontinued
0.6289 Remote Similarity NPD506 Clinical (unspecified phase)
0.6286 Remote Similarity NPD1932 Approved
0.6263 Remote Similarity NPD1086 Approved
0.6263 Remote Similarity NPD1089 Approved
0.6263 Remote Similarity NPD1090 Approved
0.6261 Remote Similarity NPD1894 Discontinued
0.6239 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6239 Remote Similarity NPD3496 Discontinued
0.6238 Remote Similarity NPD1563 Approved
0.6238 Remote Similarity NPD1066 Discontinued
0.6226 Remote Similarity NPD9261 Approved
0.6224 Remote Similarity NPD531 Approved
0.6207 Remote Similarity NPD5585 Approved
0.6207 Remote Similarity NPD9497 Clinical (unspecified phase)
0.6204 Remote Similarity NPD2551 Approved
0.6204 Remote Similarity NPD2559 Approved
0.6204 Remote Similarity NPD811 Approved
0.6204 Remote Similarity NPD3526 Approved
0.6204 Remote Similarity NPD3524 Approved
0.6204 Remote Similarity NPD812 Approved
0.6204 Remote Similarity NPD6685 Approved
0.6204 Remote Similarity NPD810 Approved
0.6204 Remote Similarity NPD968 Approved
0.62 Remote Similarity NPD1007 Discontinued
0.6186 Remote Similarity NPD422 Phase 1
0.6186 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6176 Remote Similarity NPD688 Clinical (unspecified phase)
0.6176 Remote Similarity NPD1693 Approved
0.6162 Remote Similarity NPD5347 Phase 2
0.6162 Remote Similarity NPD5346 Phase 2
0.6147 Remote Similarity NPD290 Approved
0.6139 Remote Similarity NPD1088 Approved
0.6118 Remote Similarity NPD173 Clinical (unspecified phase)
0.6117 Remote Similarity NPD1843 Approved
0.6098 Remote Similarity NPD6832 Phase 2
0.6095 Remote Similarity NPD9712 Approved
0.6087 Remote Similarity NPD5291 Approved
0.6087 Remote Similarity NPD5292 Approved
0.6087 Remote Similarity NPD4431 Clinical (unspecified phase)
0.6075 Remote Similarity NPD5765 Approved
0.6066 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6066 Remote Similarity NPD1019 Discontinued
0.6058 Remote Similarity NPD1566 Phase 3
0.6058 Remote Similarity NPD1564 Approved
0.6058 Remote Similarity NPD3495 Discontinued
0.6058 Remote Similarity NPD1565 Approved
0.6048 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6048 Remote Similarity NPD7008 Discontinued
0.6036 Remote Similarity NPD1752 Approved
0.6036 Remote Similarity NPD1756 Approved
0.6036 Remote Similarity NPD551 Approved
0.6036 Remote Similarity NPD550 Approved
0.6036 Remote Similarity NPD3646 Clinical (unspecified phase)
0.6034 Remote Similarity NPD5536 Phase 2
0.6033 Remote Similarity NPD3225 Approved
0.6033 Remote Similarity NPD5667 Approved
0.6017 Remote Similarity NPD1778 Approved
0.6017 Remote Similarity NPD4626 Approved
0.6 Remote Similarity NPD9717 Approved
0.6 Remote Similarity NPD9267 Approved
0.6 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6 Remote Similarity NPD5979 Clinical (unspecified phase)
0.6 Remote Similarity NPD9263 Approved
0.6 Remote Similarity NPD9711 Approved
0.6 Remote Similarity NPD9710 Approved
0.6 Remote Similarity NPD9264 Approved
0.5984 Remote Similarity NPD2797 Approved
0.5984 Remote Similarity NPD3266 Approved
0.5984 Remote Similarity NPD9567 Approved
0.5984 Remote Similarity NPD553 Approved
0.5984 Remote Similarity NPD552 Approved
0.5984 Remote Similarity NPD1203 Approved
0.5984 Remote Similarity NPD3267 Approved
0.5966 Remote Similarity NPD7457 Clinical (unspecified phase)
0.5963 Remote Similarity NPD794 Clinical (unspecified phase)
0.5962 Remote Similarity NPD5206 Clinical (unspecified phase)
0.595 Remote Similarity NPD4359 Approved
0.5948 Remote Similarity NPD4576 Approved
0.5948 Remote Similarity NPD4574 Approved
0.5946 Remote Similarity NPD74 Approved
0.5946 Remote Similarity NPD2329 Discontinued
0.5946 Remote Similarity NPD9266 Approved
0.5946 Remote Similarity NPD2684 Approved
0.5932 Remote Similarity NPD3535 Clinical (unspecified phase)
0.5929 Remote Similarity NPD4572 Approved
0.5929 Remote Similarity NPD4571 Approved
0.5929 Remote Similarity NPD9508 Approved
0.5929 Remote Similarity NPD6912 Phase 3
0.5929 Remote Similarity NPD4573 Approved
0.5918 Remote Similarity NPD111 Approved
0.5917 Remote Similarity NPD518 Clinical (unspecified phase)
0.5917 Remote Similarity NPD4480 Approved
0.5913 Remote Similarity NPD5951 Approved
0.5909 Remote Similarity NPD467 Phase 1
0.5906 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5893 Remote Similarity NPD4233 Approved
0.5893 Remote Similarity NPD9713 Approved
0.5893 Remote Similarity NPD4234 Approved
0.5891 Remote Similarity NPD2569 Approved
0.5891 Remote Similarity NPD2567 Approved
0.5882 Remote Similarity NPD17 Approved
0.5882 Remote Similarity NPD5305 Approved
0.5882 Remote Similarity NPD3412 Clinical (unspecified phase)
0.5882 Remote Similarity NPD5306 Approved
0.5877 Remote Similarity NPD5277 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