Structure

Physi-Chem Properties

Molecular Weight:  318.22
Volume:  347.268
LogP:  4.358
LogD:  3.385
LogS:  -3.98
# Rotatable Bonds:  2
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.621
Synthetic Accessibility Score:  4.68
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.529
MDCK Permeability:  3.0338203941937536e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.066
30% Bioavailability (F30%):  0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.828
Plasma Protein Binding (PPB):  59.721473693847656%
Volume Distribution (VD):  1.119
Pgp-substrate:  55.39369583129883%

ADMET: Metabolism

CYP1A2-inhibitor:  0.079
CYP1A2-substrate:  0.439
CYP2C19-inhibitor:  0.1
CYP2C19-substrate:  0.735
CYP2C9-inhibitor:  0.103
CYP2C9-substrate:  0.107
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.315
CYP3A4-inhibitor:  0.666
CYP3A4-substrate:  0.221

ADMET: Excretion

Clearance (CL):  12.746
Half-life (T1/2):  0.036

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.029
Drug-inuced Liver Injury (DILI):  0.162
AMES Toxicity:  0.113
Rat Oral Acute Toxicity:  0.636
Maximum Recommended Daily Dose:  0.701
Skin Sensitization:  0.147
Carcinogencity:  0.24
Eye Corrosion:  0.011
Eye Irritation:  0.05
Respiratory Toxicity:  0.941

Download Data

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Structure MOL file  
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  Natural Product: NPC79027

Natural Product ID:  NPC79027
Common Name*:   Isocoronarin D
IUPAC Name:   (3E,4R)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
Synonyms:   Isocoronarin D
Standard InCHIKey:  WCYYIFXENZTEHA-HBSPNOSKSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-13-6-9-17-19(2,3)10-5-11-20(17,4)15(13)8-7-14-16(21)12-23-18(14)22/h7,15-17,21H,1,5-6,8-12H2,2-4H3/b14-7+/t15-,16-,17-,20+/m0/s1
SMILES:  C=C1CC[C@@H]2[C@]([C@H]1C/C=C/1[C@@H](O)COC1=O)(C)CCCC2(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1099267
PubChem CID:   46871816
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np100392m]
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12027740]
NPO5033 Alpinia galanga Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[12951092]
NPO5033 Alpinia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[12951092]
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]
NPO5033 Alpinia galanga Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[15930771]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota rhizomes Kampaengsaen district, Nakhon Pathom province, Thailand n.a. PMID[18554915]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota aerial parts n.a. n.a. PMID[20196571]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[21106458]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23910596]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8176399]
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]
NPO15897 Hedychium forrestii 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]
NPO5033 Alpinia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25803 Strychnos elaeocarpa Species Loganiaceae 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]
NPO15897 Hedychium forrestii 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]
NPO5033 Alpinia galanga Species Zingiberaceae 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]
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]
NPO5033 Alpinia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5033 Alpinia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25582 Aquilegia viridiflora Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5033 Alpinia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26524 Chondria californica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19916 Phenax angustifolius Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25575 Streptomyces pseudovenezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26743 Lippia adoensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26816 Clinopodium gracile Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25086 Viburnum betulifolium Species Adoxaceae 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]
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]
NPO23589 Pecten irradians Species Pectinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24733 Celastrus dispermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24894 Parmelia tinctina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28819 Veronica liwanensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26643 Cichorium endivia Species Asteraceae 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]
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]
NPO10372 Kiggelaria africana Species Achariaceae 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]
NPO25768 Senecio ruwenzoriensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13072 Rhamnus formosana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26846 Guettarda noumeana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26554 Hexagonia speciosa Species Carabidae 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]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26676 Daphne arisanensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26208 Brombya platynema Species Rutaceae 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]
NPO25393 Coelogyne flavida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25732 Trichilia havanensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26357 Trachyrhamphus serratus Species Syngnathidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15897 Hedychium forrestii Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14283 Ponera metallica Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26481 Astragalus kabadianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22353 Lucilia caesar Species Calliphoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26392 Piptadenia colubrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15693 Guadua angustifolia Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26610 Spiraea formosana 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]
NPO23410 Potentilla candicans Species Rosaceae 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
NPT111 Cell Line K562 Homo sapiens FC = 1.6 n.a. PMID[506725]
NPT111 Cell Line K562 Homo sapiens Activity = 80.7 % PMID[506725]

☑ 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 NPC79027 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
0.9121 High Similarity NPC124512
0.9121 High Similarity NPC159763
0.9121 High Similarity NPC278386
0.8804 High Similarity NPC73911
0.8652 High Similarity NPC474396
0.8652 High Similarity NPC50488
0.8462 Intermediate Similarity NPC72845
0.8462 Intermediate Similarity NPC472814
0.8462 Intermediate Similarity NPC177037
0.8409 Intermediate Similarity NPC217394
0.8391 Intermediate Similarity NPC42476
0.8315 Intermediate Similarity NPC329692
0.828 Intermediate Similarity NPC57117
0.8214 Intermediate Similarity NPC301207
0.8182 Intermediate Similarity NPC311070
0.8172 Intermediate Similarity NPC115021
0.8118 Intermediate Similarity NPC474818
0.8118 Intermediate Similarity NPC51809
0.8118 Intermediate Similarity NPC176329
0.8118 Intermediate Similarity NPC49302
0.8118 Intermediate Similarity NPC125365
0.8105 Intermediate Similarity NPC242848
0.8081 Intermediate Similarity NPC296950
0.8081 Intermediate Similarity NPC146731
0.8068 Intermediate Similarity NPC16321
0.8023 Intermediate Similarity NPC221095
0.8023 Intermediate Similarity NPC279214
0.8023 Intermediate Similarity NPC473471
0.8021 Intermediate Similarity NPC474343
0.8021 Intermediate Similarity NPC475709
0.8 Intermediate Similarity NPC127118
0.8 Intermediate Similarity NPC209113
0.7981 Intermediate Similarity NPC264153
0.7979 Intermediate Similarity NPC53555
0.7959 Intermediate Similarity NPC303559
0.7957 Intermediate Similarity NPC51486
0.7957 Intermediate Similarity NPC182136
0.7935 Intermediate Similarity NPC474629
0.7917 Intermediate Similarity NPC473153
0.7872 Intermediate Similarity NPC303697
0.7864 Intermediate Similarity NPC235014
0.7826 Intermediate Similarity NPC473891
0.7812 Intermediate Similarity NPC209355
0.7802 Intermediate Similarity NPC86316
0.7802 Intermediate Similarity NPC106416
0.7789 Intermediate Similarity NPC156553
0.7789 Intermediate Similarity NPC152778
0.7789 Intermediate Similarity NPC469645
0.7789 Intermediate Similarity NPC469692
0.7789 Intermediate Similarity NPC139692
0.7789 Intermediate Similarity NPC162615
0.7789 Intermediate Similarity NPC205034
0.7778 Intermediate Similarity NPC161045
0.7778 Intermediate Similarity NPC469
0.7766 Intermediate Similarity NPC78973
0.7766 Intermediate Similarity NPC310479
0.7766 Intermediate Similarity NPC15059
0.7755 Intermediate Similarity NPC316598
0.7755 Intermediate Similarity NPC473154
0.7753 Intermediate Similarity NPC150502
0.7745 Intermediate Similarity NPC67321
0.7745 Intermediate Similarity NPC187435
0.7742 Intermediate Similarity NPC472810
0.7742 Intermediate Similarity NPC476803
0.7742 Intermediate Similarity NPC472809
0.7732 Intermediate Similarity NPC234993
0.7732 Intermediate Similarity NPC134072
0.7717 Intermediate Similarity NPC131813
0.7714 Intermediate Similarity NPC269530
0.7708 Intermediate Similarity NPC121825
0.7701 Intermediate Similarity NPC262747
0.7692 Intermediate Similarity NPC5103
0.7692 Intermediate Similarity NPC474865
0.7692 Intermediate Similarity NPC29133
0.7677 Intermediate Similarity NPC38855
0.7677 Intermediate Similarity NPC476299
0.7677 Intermediate Similarity NPC474012
0.767 Intermediate Similarity NPC306265
0.7667 Intermediate Similarity NPC474959
0.7667 Intermediate Similarity NPC475046
0.7667 Intermediate Similarity NPC11383
0.7667 Intermediate Similarity NPC310450
0.766 Intermediate Similarity NPC168131
0.766 Intermediate Similarity NPC174342
0.7647 Intermediate Similarity NPC477125
0.7634 Intermediate Similarity NPC312561
0.7629 Intermediate Similarity NPC183012
0.7624 Intermediate Similarity NPC159533
0.7619 Intermediate Similarity NPC470961
0.7614 Intermediate Similarity NPC279532
0.7614 Intermediate Similarity NPC209135
0.7614 Intermediate Similarity NPC474816
0.7609 Intermediate Similarity NPC476602
0.7609 Intermediate Similarity NPC30984
0.7609 Intermediate Similarity NPC329738
0.7609 Intermediate Similarity NPC11804
0.7609 Intermediate Similarity NPC65661
0.7604 Intermediate Similarity NPC472812
0.76 Intermediate Similarity NPC469657
0.76 Intermediate Similarity NPC244456
0.7596 Intermediate Similarity NPC475065
0.7593 Intermediate Similarity NPC20302
0.7593 Intermediate Similarity NPC470492
0.7593 Intermediate Similarity NPC470493
0.7593 Intermediate Similarity NPC140055
0.7593 Intermediate Similarity NPC183580
0.7593 Intermediate Similarity NPC312824
0.7593 Intermediate Similarity NPC167606
0.7593 Intermediate Similarity NPC286528
0.7586 Intermediate Similarity NPC4509
0.7582 Intermediate Similarity NPC229799
0.7582 Intermediate Similarity NPC284472
0.7582 Intermediate Similarity NPC286770
0.7582 Intermediate Similarity NPC472377
0.7579 Intermediate Similarity NPC221111
0.7579 Intermediate Similarity NPC280149
0.7579 Intermediate Similarity NPC253186
0.7576 Intermediate Similarity NPC23364
0.7573 Intermediate Similarity NPC91034
0.7573 Intermediate Similarity NPC329048
0.7573 Intermediate Similarity NPC330011
0.757 Intermediate Similarity NPC67259
0.757 Intermediate Similarity NPC147912
0.7558 Intermediate Similarity NPC168975
0.7558 Intermediate Similarity NPC75485
0.7553 Intermediate Similarity NPC476805
0.7551 Intermediate Similarity NPC16967
0.7547 Intermediate Similarity NPC191620
0.7528 Intermediate Similarity NPC99651
0.7527 Intermediate Similarity NPC478112
0.7527 Intermediate Similarity NPC469910
0.7526 Intermediate Similarity NPC469697
0.7526 Intermediate Similarity NPC53685
0.7526 Intermediate Similarity NPC191521
0.7525 Intermediate Similarity NPC472815
0.7523 Intermediate Similarity NPC709
0.7523 Intermediate Similarity NPC50774
0.75 Intermediate Similarity NPC475418
0.75 Intermediate Similarity NPC31086
0.75 Intermediate Similarity NPC233345
0.75 Intermediate Similarity NPC477783
0.75 Intermediate Similarity NPC318363
0.75 Intermediate Similarity NPC186363
0.75 Intermediate Similarity NPC47024
0.75 Intermediate Similarity NPC472811
0.75 Intermediate Similarity NPC473482
0.7477 Intermediate Similarity NPC469454
0.7477 Intermediate Similarity NPC469496
0.7477 Intermediate Similarity NPC469463
0.7475 Intermediate Similarity NPC287668
0.7475 Intermediate Similarity NPC205143
0.7474 Intermediate Similarity NPC5509
0.7474 Intermediate Similarity NPC82876
0.7474 Intermediate Similarity NPC251528
0.7474 Intermediate Similarity NPC470734
0.7473 Intermediate Similarity NPC94200
0.7455 Intermediate Similarity NPC264954
0.7453 Intermediate Similarity NPC179798
0.7453 Intermediate Similarity NPC474315
0.7453 Intermediate Similarity NPC304180
0.7451 Intermediate Similarity NPC69171
0.7451 Intermediate Similarity NPC476237
0.7451 Intermediate Similarity NPC471938
0.7451 Intermediate Similarity NPC474165
0.7447 Intermediate Similarity NPC166857
0.7447 Intermediate Similarity NPC181103
0.7429 Intermediate Similarity NPC474243
0.7426 Intermediate Similarity NPC308824
0.7423 Intermediate Similarity NPC166346
0.7419 Intermediate Similarity NPC35933
0.7419 Intermediate Similarity NPC471795
0.7419 Intermediate Similarity NPC52628
0.7419 Intermediate Similarity NPC329630
0.7419 Intermediate Similarity NPC470755
0.7412 Intermediate Similarity NPC189745
0.7404 Intermediate Similarity NPC473284
0.74 Intermediate Similarity NPC278008
0.74 Intermediate Similarity NPC141191
0.74 Intermediate Similarity NPC474440
0.7396 Intermediate Similarity NPC477782
0.7396 Intermediate Similarity NPC158488
0.7396 Intermediate Similarity NPC232426
0.7396 Intermediate Similarity NPC474232
0.7396 Intermediate Similarity NPC469368
0.7396 Intermediate Similarity NPC281942
0.7396 Intermediate Similarity NPC472307
0.7391 Intermediate Similarity NPC79945
0.7391 Intermediate Similarity NPC49208
0.7391 Intermediate Similarity NPC22611
0.7391 Intermediate Similarity NPC23748
0.7391 Intermediate Similarity NPC44261
0.7387 Intermediate Similarity NPC474370
0.7386 Intermediate Similarity NPC203277
0.7379 Intermediate Similarity NPC471937
0.7379 Intermediate Similarity NPC258532
0.7379 Intermediate Similarity NPC203659
0.7374 Intermediate Similarity NPC162346
0.7368 Intermediate Similarity NPC472378
0.7368 Intermediate Similarity NPC104560
0.7368 Intermediate Similarity NPC226863

  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 NPC79027 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
0.9121 High Similarity NPD4225 Approved
0.7593 Intermediate Similarity NPD7115 Discovery
0.75 Intermediate Similarity NPD7637 Suspended
0.7333 Intermediate Similarity NPD6686 Approved
0.7312 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD5785 Approved
0.7157 Intermediate Similarity NPD7640 Approved
0.7157 Intermediate Similarity NPD7639 Approved
0.71 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7638 Approved
0.7037 Intermediate Similarity NPD6371 Approved
0.6875 Remote Similarity NPD1694 Approved
0.6869 Remote Similarity NPD6698 Approved
0.6869 Remote Similarity NPD46 Approved
0.6762 Remote Similarity NPD5344 Discontinued
0.6759 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6737 Remote Similarity NPD5209 Approved
0.6731 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6701 Remote Similarity NPD5363 Approved
0.67 Remote Similarity NPD7838 Discovery
0.6636 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6569 Remote Similarity NPD5779 Approved
0.6569 Remote Similarity NPD5778 Approved
0.6569 Remote Similarity NPD6399 Phase 3
0.6566 Remote Similarity NPD7524 Approved
0.6542 Remote Similarity NPD7632 Discontinued
0.6476 Remote Similarity NPD6083 Phase 2
0.6476 Remote Similarity NPD6084 Phase 2
0.6471 Remote Similarity NPD6411 Approved
0.6471 Remote Similarity NPD7983 Approved
0.6465 Remote Similarity NPD7146 Approved
0.6465 Remote Similarity NPD5330 Approved
0.6465 Remote Similarity NPD6684 Approved
0.6465 Remote Similarity NPD7521 Approved
0.6465 Remote Similarity NPD3618 Phase 1
0.6465 Remote Similarity NPD7334 Approved
0.6465 Remote Similarity NPD6409 Approved
0.6429 Remote Similarity NPD3665 Phase 1
0.6429 Remote Similarity NPD3666 Approved
0.6429 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3133 Approved
0.6415 Remote Similarity NPD5696 Approved
0.6392 Remote Similarity NPD3667 Approved
0.6392 Remote Similarity NPD4270 Approved
0.6392 Remote Similarity NPD4269 Approved
0.6383 Remote Similarity NPD5776 Phase 2
0.6383 Remote Similarity NPD6925 Approved
0.6364 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6356 Remote Similarity NPD6319 Approved
0.6355 Remote Similarity NPD6648 Approved
0.6354 Remote Similarity NPD7332 Phase 2
0.6354 Remote Similarity NPD7514 Phase 3
0.6354 Remote Similarity NPD4252 Approved
0.6354 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6346 Remote Similarity NPD7748 Approved
0.6341 Remote Similarity NPD7319 Approved
0.6337 Remote Similarity NPD6903 Approved
0.6337 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6327 Remote Similarity NPD7154 Phase 3
0.6327 Remote Similarity NPD6695 Phase 3
0.6325 Remote Similarity NPD7328 Approved
0.6325 Remote Similarity NPD7327 Approved
0.6321 Remote Similarity NPD7902 Approved
0.6316 Remote Similarity NPD8297 Approved
0.6316 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7145 Approved
0.6316 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6311 Remote Similarity NPD7515 Phase 2
0.6306 Remote Similarity NPD6412 Phase 2
0.6306 Remote Similarity NPD5697 Approved
0.6303 Remote Similarity NPD7503 Approved
0.6303 Remote Similarity NPD8033 Approved
0.63 Remote Similarity NPD5786 Approved
0.6289 Remote Similarity NPD6902 Approved
0.6286 Remote Similarity NPD5695 Phase 3
0.6277 Remote Similarity NPD6933 Approved
0.6275 Remote Similarity NPD6101 Approved
0.6275 Remote Similarity NPD6051 Approved
0.6275 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6271 Remote Similarity NPD7516 Approved
0.6263 Remote Similarity NPD4786 Approved
0.6263 Remote Similarity NPD7338 Clinical (unspecified phase)
0.625 Remote Similarity NPD6881 Approved
0.625 Remote Similarity NPD2685 Clinical (unspecified phase)
0.625 Remote Similarity NPD6929 Approved
0.625 Remote Similarity NPD5345 Clinical (unspecified phase)
0.625 Remote Similarity NPD6899 Approved
0.623 Remote Similarity NPD7507 Approved
0.6228 Remote Similarity NPD6650 Approved
0.6228 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6228 Remote Similarity NPD6649 Approved
0.6226 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6218 Remote Similarity NPD8377 Approved
0.6218 Remote Similarity NPD8294 Approved
0.6216 Remote Similarity NPD6675 Approved
0.6216 Remote Similarity NPD7128 Approved
0.6216 Remote Similarity NPD5739 Approved
0.6216 Remote Similarity NPD6402 Approved
0.6195 Remote Similarity NPD6372 Approved
0.6195 Remote Similarity NPD6013 Approved
0.6195 Remote Similarity NPD6014 Approved
0.6195 Remote Similarity NPD6373 Approved
0.6195 Remote Similarity NPD6012 Approved
0.619 Remote Similarity NPD5282 Discontinued
0.6186 Remote Similarity NPD4822 Approved
0.6186 Remote Similarity NPD6930 Phase 2
0.6186 Remote Similarity NPD6931 Approved
0.6186 Remote Similarity NPD4821 Approved
0.6186 Remote Similarity NPD4819 Approved
0.6186 Remote Similarity NPD4695 Discontinued
0.6186 Remote Similarity NPD4820 Approved
0.6176 Remote Similarity NPD6672 Approved
0.6176 Remote Similarity NPD5737 Approved
0.617 Remote Similarity NPD8264 Approved
0.6167 Remote Similarity NPD8379 Approved
0.6167 Remote Similarity NPD8378 Approved
0.6167 Remote Similarity NPD8335 Approved
0.6167 Remote Similarity NPD8380 Approved
0.6167 Remote Similarity NPD8516 Approved
0.6167 Remote Similarity NPD8513 Phase 3
0.6167 Remote Similarity NPD8517 Approved
0.6167 Remote Similarity NPD8296 Approved
0.6167 Remote Similarity NPD8515 Approved
0.6162 Remote Similarity NPD5362 Discontinued
0.6161 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6161 Remote Similarity NPD5701 Approved
0.6154 Remote Similarity NPD5693 Phase 1
0.6154 Remote Similarity NPD6923 Approved
0.6154 Remote Similarity NPD6079 Approved
0.6154 Remote Similarity NPD6922 Approved
0.6148 Remote Similarity NPD7492 Approved
0.6146 Remote Similarity NPD4268 Approved
0.6146 Remote Similarity NPD4271 Approved
0.614 Remote Similarity NPD6883 Approved
0.614 Remote Similarity NPD7290 Approved
0.614 Remote Similarity NPD7102 Approved
0.6139 Remote Similarity NPD4519 Discontinued
0.6139 Remote Similarity NPD4623 Approved
0.6139 Remote Similarity NPD4249 Approved
0.6139 Remote Similarity NPD5279 Phase 3
0.6139 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6136 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6132 Remote Similarity NPD5210 Approved
0.6132 Remote Similarity NPD4629 Approved
0.6122 Remote Similarity NPD5369 Approved
0.6122 Remote Similarity NPD6898 Phase 1
0.6121 Remote Similarity NPD4632 Approved
0.6117 Remote Similarity NPD4753 Phase 2
0.6117 Remote Similarity NPD5328 Approved
0.6106 Remote Similarity NPD6011 Approved
0.6106 Remote Similarity NPD7320 Approved
0.6105 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6098 Remote Similarity NPD6616 Approved
0.6092 Remote Similarity NPD4191 Approved
0.6092 Remote Similarity NPD4194 Approved
0.6092 Remote Similarity NPD4192 Approved
0.6092 Remote Similarity NPD4193 Approved
0.6091 Remote Similarity NPD5211 Phase 2
0.6087 Remote Similarity NPD7144 Approved
0.6087 Remote Similarity NPD4691 Approved
0.6087 Remote Similarity NPD6617 Approved
0.6087 Remote Similarity NPD8130 Phase 1
0.6087 Remote Similarity NPD6847 Approved
0.6087 Remote Similarity NPD6869 Approved
0.6087 Remote Similarity NPD7143 Approved
0.6083 Remote Similarity NPD6054 Approved
0.6078 Remote Similarity NPD7750 Discontinued
0.6078 Remote Similarity NPD4250 Approved
0.6078 Remote Similarity NPD4251 Approved
0.6071 Remote Similarity NPD6640 Phase 3
0.6066 Remote Similarity NPD8328 Phase 3
0.6064 Remote Similarity NPD6926 Approved
0.6064 Remote Similarity NPD6924 Approved
0.6048 Remote Similarity NPD7078 Approved
0.6042 Remote Similarity NPD6932 Approved
0.604 Remote Similarity NPD1696 Phase 3
0.6038 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6038 Remote Similarity NPD7900 Approved
0.6034 Remote Similarity NPD6053 Discontinued
0.6034 Remote Similarity NPD6882 Approved
0.6033 Remote Similarity NPD6016 Approved
0.6033 Remote Similarity NPD6015 Approved
0.6022 Remote Similarity NPD7150 Approved
0.6022 Remote Similarity NPD7151 Approved
0.6022 Remote Similarity NPD7152 Approved
0.6 Remote Similarity NPD4634 Approved
0.6 Remote Similarity NPD6110 Phase 1
0.6 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6 Remote Similarity NPD7736 Approved
0.6 Remote Similarity NPD5331 Approved
0.6 Remote Similarity NPD6942 Approved
0.6 Remote Similarity NPD5332 Approved
0.6 Remote Similarity NPD7339 Approved
0.6 Remote Similarity NPD8039 Approved
0.5984 Remote Similarity NPD5988 Approved
0.5984 Remote Similarity NPD6370 Approved
0.5982 Remote Similarity NPD5141 Approved
0.5981 Remote Similarity NPD6356 Clinical (unspecified phase)

  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