Structure

Physi-Chem Properties

Molecular Weight:  314.19
Volume:  341.995
LogP:  4.68
LogD:  4.37
LogS:  -5.461
# Rotatable Bonds:  3
TPSA:  47.28
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.771
Synthetic Accessibility Score:  3.998
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.832
MDCK Permeability:  2.1577236111625098e-05
Pgp-inhibitor:  0.986
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.024
30% Bioavailability (F30%):  0.877

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.015
Plasma Protein Binding (PPB):  93.93981170654297%
Volume Distribution (VD):  2.187
Pgp-substrate:  1.673500657081604%

ADMET: Metabolism

CYP1A2-inhibitor:  0.608
CYP1A2-substrate:  0.673
CYP2C19-inhibitor:  0.889
CYP2C19-substrate:  0.592
CYP2C9-inhibitor:  0.92
CYP2C9-substrate:  0.201
CYP2D6-inhibitor:  0.879
CYP2D6-substrate:  0.109
CYP3A4-inhibitor:  0.835
CYP3A4-substrate:  0.394

ADMET: Excretion

Clearance (CL):  12.786
Half-life (T1/2):  0.091

ADMET: Toxicity

hERG Blockers:  0.018
Human Hepatotoxicity (H-HT):  0.227
Drug-inuced Liver Injury (DILI):  0.175
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.929
Maximum Recommended Daily Dose:  0.682
Skin Sensitization:  0.085
Carcinogencity:  0.887
Eye Corrosion:  0.029
Eye Irritation:  0.098
Respiratory Toxicity:  0.984

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  Natural Product: NPC246392

Natural Product ID:  NPC246392
Common Name*:   7-Hydroxy Hedychenone
IUPAC Name:   (4R,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-2-hydroxy-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-4H-naphthalen-1-one
Synonyms:   7-Hydroxy Hedychenone
Standard InCHIKey:  JPMIIVCZMUYZRA-MMZWZMGNSA-N
Standard InCHI:  InChI=1S/C20H26O3/c1-13-15(7-6-14-8-11-23-12-14)20(4)10-5-9-19(2,3)18(20)17(22)16(13)21/h6-8,11-12,15,18,21H,5,9-10H2,1-4H3/b7-6+/t15-,18-,20+/m0/s1
SMILES:  CC1=C(O)C(=O)[C@@H]2[C@]([C@H]1/C=C/c1cocc1)(C)CCCC2(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL466121
PubChem CID:   12189408
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12027740]
NPO25854 Tripterospermum lanceolatum Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[1517742]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[19027298]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[19332371]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[19782567]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[21106458]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23422227]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota Leaves n.a. Database[FooDB]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26610 Spiraea formosana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26816 Clinopodium gracile Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25086 Viburnum betulifolium Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26743 Lippia adoensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26306 Pyrobaculum organotrophum Species Thermoproteaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO26079 Asterococcus muratae Species Cerococcidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24829 Gyrostroma missouriense n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24894 Parmelia tinctina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28819 Veronica liwanensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23589 Pecten irradians Species Pectinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22353 Lucilia caesar Species Calliphoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25906 Acacia linarioides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26175 Spongionella gracilis Species Dictyodendrillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26610 Spiraea formosana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7465 Vachellia leucophloea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13051 Perymenium jelskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10372 Kiggelaria africana Species Achariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13072 Rhamnus formosana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25768 Senecio ruwenzoriensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26846 Guettarda noumeana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24608 Gaertnera morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25854 Tripterospermum lanceolatum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21639 Prunus mahaleb Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26676 Daphne arisanensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17771 Senna didymobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29093 Homalium longifolium Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26208 Brombya platynema Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26357 Trachyrhamphus serratus Species Syngnathidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25732 Trichilia havanensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26481 Astragalus kabadianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14283 Ponera metallica Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24733 Celastrus dispermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15693 Guadua angustifolia Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26392 Piptadenia colubrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25996 Stenolobium stans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23410 Potentilla candicans Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26524 Chondria californica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25582 Aquilegia viridiflora Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26554 Hexagonia speciosa Species Carabidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19916 Phenax angustifolius Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25393 Coelogyne flavida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25575 Streptomyces pseudovenezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]

☑ 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
NPT2 Others Unspecified Inhibition = 13.5 % PMID[537956]

☑ 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 NPC246392 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
0.9917 High Similarity NPC26532
0.9669 High Similarity NPC290955
0.9431 High Similarity NPC279877
0.9355 High Similarity NPC208389
0.9244 High Similarity NPC87466
0.896 High Similarity NPC23086
0.888 High Similarity NPC300098
0.888 High Similarity NPC290193
0.8837 High Similarity NPC473982
0.8819 High Similarity NPC112706
0.8819 High Similarity NPC207294
0.876 High Similarity NPC61788
0.875 High Similarity NPC59502
0.874 High Similarity NPC83178
0.8672 High Similarity NPC329707
0.8661 High Similarity NPC138139
0.8661 High Similarity NPC46536
0.8657 High Similarity NPC202260
0.864 High Similarity NPC477967
0.8636 High Similarity NPC158525
0.8626 High Similarity NPC218838
0.8618 High Similarity NPC243704
0.8593 High Similarity NPC148374
0.8583 High Similarity NPC471074
0.8583 High Similarity NPC473885
0.856 High Similarity NPC97566
0.8527 High Similarity NPC477123
0.8527 High Similarity NPC477966
0.8504 High Similarity NPC118853
0.85 High Similarity NPC277525
0.8467 Intermediate Similarity NPC263337
0.8456 Intermediate Similarity NPC90296
0.8433 Intermediate Similarity NPC46896
0.8425 Intermediate Similarity NPC16922
0.8409 Intermediate Similarity NPC471995
0.8385 Intermediate Similarity NPC477040
0.8385 Intermediate Similarity NPC477039
0.8382 Intermediate Similarity NPC474722
0.8374 Intermediate Similarity NPC150895
0.837 Intermediate Similarity NPC307401
0.8358 Intermediate Similarity NPC476947
0.8346 Intermediate Similarity NPC471006
0.8333 Intermediate Similarity NPC89133
0.8321 Intermediate Similarity NPC473983
0.8321 Intermediate Similarity NPC201370
0.8309 Intermediate Similarity NPC472376
0.8295 Intermediate Similarity NPC179354
0.8281 Intermediate Similarity NPC272899
0.8273 Intermediate Similarity NPC243577
0.8264 Intermediate Similarity NPC246164
0.8258 Intermediate Similarity NPC476925
0.8248 Intermediate Similarity NPC90953
0.8244 Intermediate Similarity NPC476917
0.8244 Intermediate Similarity NPC327527
0.8231 Intermediate Similarity NPC74612
0.8217 Intermediate Similarity NPC477038
0.8217 Intermediate Similarity NPC243269
0.8217 Intermediate Similarity NPC178382
0.8217 Intermediate Similarity NPC477965
0.8217 Intermediate Similarity NPC130275
0.8209 Intermediate Similarity NPC470740
0.8203 Intermediate Similarity NPC317217
0.8195 Intermediate Similarity NPC298190
0.8162 Intermediate Similarity NPC146872
0.8154 Intermediate Similarity NPC303010
0.8134 Intermediate Similarity NPC471817
0.8102 Intermediate Similarity NPC170604
0.8102 Intermediate Similarity NPC215109
0.8095 Intermediate Similarity NPC212918
0.808 Intermediate Similarity NPC205523
0.8077 Intermediate Similarity NPC65735
0.8077 Intermediate Similarity NPC188377
0.8074 Intermediate Similarity NPC293253
0.8071 Intermediate Similarity NPC52412
0.8071 Intermediate Similarity NPC473152
0.8058 Intermediate Similarity NPC67003
0.8043 Intermediate Similarity NPC471996
0.8028 Intermediate Similarity NPC185456
0.8015 Intermediate Similarity NPC474829
0.8014 Intermediate Similarity NPC267632
0.8 Intermediate Similarity NPC205765
0.8 Intermediate Similarity NPC228842
0.8 Intermediate Similarity NPC212257
0.7986 Intermediate Similarity NPC93666
0.7971 Intermediate Similarity NPC310830
0.7956 Intermediate Similarity NPC92941
0.7953 Intermediate Similarity NPC217180
0.7953 Intermediate Similarity NPC312525
0.7953 Intermediate Similarity NPC144745
0.7953 Intermediate Similarity NPC208906
0.7945 Intermediate Similarity NPC272590
0.7943 Intermediate Similarity NPC475519
0.7943 Intermediate Similarity NPC121158
0.7929 Intermediate Similarity NPC56197
0.7926 Intermediate Similarity NPC477645
0.7923 Intermediate Similarity NPC36255
0.7917 Intermediate Similarity NPC302987
0.7917 Intermediate Similarity NPC471174
0.7914 Intermediate Similarity NPC177262
0.7914 Intermediate Similarity NPC220094
0.7914 Intermediate Similarity NPC476943
0.7914 Intermediate Similarity NPC236532
0.791 Intermediate Similarity NPC223063
0.791 Intermediate Similarity NPC120836
0.7902 Intermediate Similarity NPC245522
0.7902 Intermediate Similarity NPC114513
0.7895 Intermediate Similarity NPC474830
0.7891 Intermediate Similarity NPC294511
0.7891 Intermediate Similarity NPC121615
0.7887 Intermediate Similarity NPC476946
0.7883 Intermediate Similarity NPC106247
0.7874 Intermediate Similarity NPC79202
0.7874 Intermediate Similarity NPC59035
0.7867 Intermediate Similarity NPC116639
0.7867 Intermediate Similarity NPC472823
0.7847 Intermediate Similarity NPC346
0.7847 Intermediate Similarity NPC478166
0.7842 Intermediate Similarity NPC42400
0.7842 Intermediate Similarity NPC470742
0.7832 Intermediate Similarity NPC251865
0.7832 Intermediate Similarity NPC476944
0.7829 Intermediate Similarity NPC137710
0.7826 Intermediate Similarity NPC265793
0.7826 Intermediate Similarity NPC209858
0.7808 Intermediate Similarity NPC234494
0.7808 Intermediate Similarity NPC470998
0.7803 Intermediate Similarity NPC83115
0.7801 Intermediate Similarity NPC473681
0.7801 Intermediate Similarity NPC61157
0.7801 Intermediate Similarity NPC218204
0.7795 Intermediate Similarity NPC28054
0.7793 Intermediate Similarity NPC250228
0.7793 Intermediate Similarity NPC216755
0.7793 Intermediate Similarity NPC71821
0.7786 Intermediate Similarity NPC130976
0.7785 Intermediate Similarity NPC88958
0.7785 Intermediate Similarity NPC281258
0.7778 Intermediate Similarity NPC56731
0.7778 Intermediate Similarity NPC247221
0.7778 Intermediate Similarity NPC5676
0.7778 Intermediate Similarity NPC290038
0.7755 Intermediate Similarity NPC470997
0.7755 Intermediate Similarity NPC196846
0.7752 Intermediate Similarity NPC187547
0.7752 Intermediate Similarity NPC21831
0.7744 Intermediate Similarity NPC230979
0.774 Intermediate Similarity NPC476941
0.774 Intermediate Similarity NPC476942
0.7733 Intermediate Similarity NPC41880
0.7733 Intermediate Similarity NPC104736
0.773 Intermediate Similarity NPC233707
0.7724 Intermediate Similarity NPC233763
0.7724 Intermediate Similarity NPC262198
0.7718 Intermediate Similarity NPC44606
0.7718 Intermediate Similarity NPC282793
0.7714 Intermediate Similarity NPC471670
0.7714 Intermediate Similarity NPC64157
0.7714 Intermediate Similarity NPC473268
0.7714 Intermediate Similarity NPC278832
0.771 Intermediate Similarity NPC79557
0.7708 Intermediate Similarity NPC199044
0.7708 Intermediate Similarity NPC238843
0.7708 Intermediate Similarity NPC158871
0.7708 Intermediate Similarity NPC142113
0.7704 Intermediate Similarity NPC474438
0.7704 Intermediate Similarity NPC474279
0.7703 Intermediate Similarity NPC472787
0.7698 Intermediate Similarity NPC324117
0.7692 Intermediate Similarity NPC473969
0.7687 Intermediate Similarity NPC474260
0.7687 Intermediate Similarity NPC329694
0.7687 Intermediate Similarity NPC211625
0.7687 Intermediate Similarity NPC329922
0.7687 Intermediate Similarity NPC81912
0.7682 Intermediate Similarity NPC194499
0.7682 Intermediate Similarity NPC195954
0.7682 Intermediate Similarity NPC88007
0.7682 Intermediate Similarity NPC304692
0.7682 Intermediate Similarity NPC7059
0.7681 Intermediate Similarity NPC474407
0.7681 Intermediate Similarity NPC474425
0.7681 Intermediate Similarity NPC474426
0.7676 Intermediate Similarity NPC18904
0.7671 Intermediate Similarity NPC255414
0.7671 Intermediate Similarity NPC476938
0.7671 Intermediate Similarity NPC476937
0.7667 Intermediate Similarity NPC214541
0.7667 Intermediate Similarity NPC44675
0.7667 Intermediate Similarity NPC75310
0.7667 Intermediate Similarity NPC469966
0.7662 Intermediate Similarity NPC261184
0.7652 Intermediate Similarity NPC471549
0.7652 Intermediate Similarity NPC473379
0.7651 Intermediate Similarity NPC44577
0.7651 Intermediate Similarity NPC470996
0.7651 Intermediate Similarity NPC33938
0.7651 Intermediate Similarity NPC145830
0.7647 Intermediate Similarity NPC198904
0.7639 Intermediate Similarity NPC64568
0.7635 Intermediate Similarity NPC46551

  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 NPC246392 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
0.7857 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD6273 Approved
0.7364 Intermediate Similarity NPD1241 Discontinued
0.7361 Intermediate Similarity NPD1471 Phase 3
0.7333 Intermediate Similarity NPD3972 Approved
0.732 Intermediate Similarity NPD5761 Phase 2
0.732 Intermediate Similarity NPD5760 Phase 2
0.7284 Intermediate Similarity NPD6765 Approved
0.7284 Intermediate Similarity NPD6764 Approved
0.7241 Intermediate Similarity NPD2344 Approved
0.7239 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD1876 Approved
0.7222 Intermediate Similarity NPD2799 Discontinued
0.7211 Intermediate Similarity NPD4628 Phase 3
0.7169 Intermediate Similarity NPD8434 Phase 2
0.7161 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD2798 Approved
0.7108 Intermediate Similarity NPD6785 Approved
0.7108 Intermediate Similarity NPD6784 Approved
0.7095 Intermediate Similarity NPD7003 Approved
0.705 Intermediate Similarity NPD1049 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD2309 Approved
0.7014 Intermediate Similarity NPD6355 Discontinued
0.7007 Intermediate Similarity NPD2346 Discontinued
0.7007 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.6993 Remote Similarity NPD8032 Phase 2
0.6929 Remote Similarity NPD2797 Approved
0.6923 Remote Similarity NPD2313 Discontinued
0.6918 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6913 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6903 Remote Similarity NPD6599 Discontinued
0.6867 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6857 Remote Similarity NPD1283 Approved
0.6853 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6839 Remote Similarity NPD7458 Discontinued
0.6839 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6835 Remote Similarity NPD1608 Approved
0.6828 Remote Similarity NPD4140 Approved
0.6806 Remote Similarity NPD3268 Approved
0.6797 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6788 Remote Similarity NPD1651 Approved
0.6788 Remote Similarity NPD5585 Approved
0.6783 Remote Similarity NPD6832 Phase 2
0.6776 Remote Similarity NPD643 Clinical (unspecified phase)
0.6757 Remote Similarity NPD4308 Phase 3
0.6755 Remote Similarity NPD4110 Phase 3
0.6755 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6755 Remote Similarity NPD3750 Approved
0.6742 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6739 Remote Similarity NPD2932 Approved
0.6739 Remote Similarity NPD1778 Approved
0.6733 Remote Similarity NPD4534 Discontinued
0.6714 Remote Similarity NPD9717 Approved
0.6712 Remote Similarity NPD3142 Approved
0.6712 Remote Similarity NPD3140 Approved
0.6711 Remote Similarity NPD1551 Phase 2
0.6711 Remote Similarity NPD2796 Approved
0.6711 Remote Similarity NPD6100 Approved
0.6711 Remote Similarity NPD4476 Approved
0.6711 Remote Similarity NPD6099 Approved
0.6711 Remote Similarity NPD4477 Approved
0.671 Remote Similarity NPD920 Approved
0.671 Remote Similarity NPD3873 Phase 3
0.671 Remote Similarity NPD3869 Phase 3
0.6707 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6692 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6691 Remote Similarity NPD7457 Clinical (unspecified phase)
0.669 Remote Similarity NPD6798 Discontinued
0.6689 Remote Similarity NPD2800 Approved
0.6688 Remote Similarity NPD642 Clinical (unspecified phase)
0.6688 Remote Similarity NPD7028 Phase 2
0.6667 Remote Similarity NPD7236 Approved
0.6667 Remote Similarity NPD5327 Phase 3
0.6667 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7819 Suspended
0.6645 Remote Similarity NPD8166 Discontinued
0.6644 Remote Similarity NPD3748 Approved
0.6643 Remote Similarity NPD1281 Approved
0.6642 Remote Similarity NPD9092 Discovery
0.6624 Remote Similarity NPD3226 Approved
0.6623 Remote Similarity NPD5958 Discontinued
0.6623 Remote Similarity NPD6799 Approved
0.6621 Remote Similarity NPD7095 Approved
0.6619 Remote Similarity NPD17 Approved
0.6619 Remote Similarity NPD3019 Approved
0.6618 Remote Similarity NPD7157 Approved
0.6605 Remote Similarity NPD919 Approved
0.6604 Remote Similarity NPD6279 Approved
0.6604 Remote Similarity NPD6280 Approved
0.6601 Remote Similarity NPD2354 Approved
0.6601 Remote Similarity NPD3887 Approved
0.66 Remote Similarity NPD2935 Discontinued
0.6599 Remote Similarity NPD4307 Phase 2
0.6599 Remote Similarity NPD2979 Phase 3
0.6599 Remote Similarity NPD4060 Phase 1
0.6597 Remote Similarity NPD9494 Approved
0.6594 Remote Similarity NPD1894 Discontinued
0.6584 Remote Similarity NPD3882 Suspended
0.6581 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6579 Remote Similarity NPD1243 Approved
0.6575 Remote Similarity NPD3764 Approved
0.6573 Remote Similarity NPD3266 Approved
0.6573 Remote Similarity NPD1203 Approved
0.6573 Remote Similarity NPD3267 Approved
0.6568 Remote Similarity NPD6559 Discontinued
0.6556 Remote Similarity NPD5763 Approved
0.6556 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6556 Remote Similarity NPD6005 Phase 3
0.6556 Remote Similarity NPD5762 Approved
0.6556 Remote Similarity NPD6004 Phase 3
0.6556 Remote Similarity NPD6002 Phase 3
0.6556 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6554 Remote Similarity NPD5735 Approved
0.6549 Remote Similarity NPD4359 Approved
0.6547 Remote Similarity NPD5691 Approved
0.6543 Remote Similarity NPD7075 Discontinued
0.6538 Remote Similarity NPD5049 Phase 3
0.6531 Remote Similarity NPD4062 Phase 3
0.6531 Remote Similarity NPD6233 Phase 2
0.6528 Remote Similarity NPD5647 Approved
0.6524 Remote Similarity NPD1247 Approved
0.6524 Remote Similarity NPD8127 Discontinued
0.6522 Remote Similarity NPD2296 Approved
0.6522 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6519 Remote Similarity NPD2649 Approved
0.6519 Remote Similarity NPD2651 Approved
0.6513 Remote Similarity NPD1549 Phase 2
0.651 Remote Similarity NPD6353 Approved
0.651 Remote Similarity NPD1607 Approved
0.6507 Remote Similarity NPD7008 Discontinued
0.65 Remote Similarity NPD7577 Discontinued
0.65 Remote Similarity NPD4626 Approved
0.6486 Remote Similarity NPD1240 Approved
0.6475 Remote Similarity NPD9545 Approved
0.6474 Remote Similarity NPD4661 Approved
0.6474 Remote Similarity NPD4662 Approved
0.6466 Remote Similarity NPD2684 Approved
0.6466 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6464 Remote Similarity NPD3057 Approved
0.6463 Remote Similarity NPD411 Approved
0.6463 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6456 Remote Similarity NPD7239 Suspended
0.6454 Remote Similarity NPD3496 Discontinued
0.6447 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6447 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6447 Remote Similarity NPD2353 Approved
0.6447 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6443 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6442 Remote Similarity NPD3749 Approved
0.6439 Remote Similarity NPD3134 Approved
0.6438 Remote Similarity NPD7411 Suspended
0.6438 Remote Similarity NPD2614 Approved
0.6429 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6424 Remote Similarity NPD1510 Phase 2
0.6423 Remote Similarity NPD690 Clinical (unspecified phase)
0.6423 Remote Similarity NPD5951 Approved
0.6423 Remote Similarity NPD2629 Approved
0.6419 Remote Similarity NPD6663 Approved
0.6414 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6414 Remote Similarity NPD1019 Discontinued
0.6414 Remote Similarity NPD4624 Approved
0.6412 Remote Similarity NPD1237 Approved
0.6405 Remote Similarity NPD2424 Discontinued
0.6405 Remote Similarity NPD2897 Discontinued
0.6398 Remote Similarity NPD6801 Discontinued
0.6392 Remote Similarity NPD5403 Approved
0.6389 Remote Similarity NPD6696 Suspended
0.6382 Remote Similarity NPD2438 Suspended
0.6382 Remote Similarity NPD2531 Phase 2
0.638 Remote Similarity NPD4947 Clinical (unspecified phase)
0.638 Remote Similarity NPD7768 Phase 2
0.6374 Remote Similarity NPD2972 Approved
0.6374 Remote Similarity NPD3533 Approved
0.6374 Remote Similarity NPD2491 Approved
0.637 Remote Similarity NPD5736 Approved
0.637 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6369 Remote Similarity NPD2532 Approved
0.6369 Remote Similarity NPD2534 Approved
0.6369 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6369 Remote Similarity NPD2533 Approved
0.6369 Remote Similarity NPD5401 Approved
0.6364 Remote Similarity NPD5494 Approved
0.6358 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6351 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6347 Remote Similarity NPD3926 Phase 2
0.6346 Remote Similarity NPD7440 Discontinued
0.6345 Remote Similarity NPD6362 Approved
0.6343 Remote Similarity NPD2182 Approved
0.6338 Remote Similarity NPD3023 Approved
0.6338 Remote Similarity NPD3026 Approved
0.6333 Remote Similarity NPD4622 Approved
0.6333 Remote Similarity NPD4618 Approved
0.6333 Remote Similarity NPD447 Suspended
0.6331 Remote Similarity NPD9493 Approved
0.6331 Remote Similarity NPD405 Clinical (unspecified phase)
0.6331 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6323 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6312 Remote Similarity NPD3025 Approved
0.6312 Remote Similarity NPD3024 Approved
0.6309 Remote Similarity NPD4870 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