Structure

Physi-Chem Properties

Molecular Weight:  234.13
Volume:  243.492
LogP:  1.876
LogD:  1.978
LogS:  -3.57
# Rotatable Bonds:  1
TPSA:  46.67
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.653
Synthetic Accessibility Score:  4.318
Fsp3:  0.714
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:  -4.728
MDCK Permeability:  2.1420453776954673e-05
Pgp-inhibitor:  0.054
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.435

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.666
Plasma Protein Binding (PPB):  65.42432403564453%
Volume Distribution (VD):  0.595
Pgp-substrate:  45.15620422363281%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.974
CYP2C19-inhibitor:  0.045
CYP2C19-substrate:  0.848
CYP2C9-inhibitor:  0.017
CYP2C9-substrate:  0.043
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.076
CYP3A4-inhibitor:  0.063
CYP3A4-substrate:  0.756

ADMET: Excretion

Clearance (CL):  15.479
Half-life (T1/2):  0.372

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.195
Drug-inuced Liver Injury (DILI):  0.144
AMES Toxicity:  0.738
Rat Oral Acute Toxicity:  0.196
Maximum Recommended Daily Dose:  0.275
Skin Sensitization:  0.336
Carcinogencity:  0.919
Eye Corrosion:  0.539
Eye Irritation:  0.154
Respiratory Toxicity:  0.952

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  Natural Product: NPC60951

Natural Product ID:  NPC60951
Common Name*:   Oxyphyllanene C
IUPAC Name:   (1aS,3aS,7bR)-1a-acetyl-3a,7-dimethyl-3,4,5,7b-tetrahydro-2H-naphtho[1,2-b]oxiren-6-one
Synonyms:   Oxyphyllanene C
Standard InCHIKey:  WEPFDGKIDPCING-MGPQQGTHSA-N
Standard InCHI:  InChI=1S/C14H18O3/c1-8-10(16)4-5-13(3)6-7-14(9(2)15)12(17-14)11(8)13/h12H,4-7H2,1-3H3/t12-,13-,14-/m1/s1
SMILES:  O=C1CC[C@]2(C(=C1C)[C@H]1O[C@]1(CC2)C(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1949796
PubChem CID:   57335616
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001729] Oxepanes

*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
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(81)85171-0]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota Whole plant n.a. n.a. PMID[11141121]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[11514174]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota fruit Hainan Island, China 1998 PMID[12398545]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[18057725]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. PMID[18293903]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. PMID[19432411]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[22277277]
NPO25106 Arnica parryi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[23583435]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. PMID[24669201]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[25757283]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[9157192]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota stem bark n.a. n.a. PMID[9157192]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23288 Justicia betonica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25130 Hylotrupes bajulus Species Cerambycidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23750 Escontria chiotilla Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25106 Arnica parryi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24659 Eremurus chinensis Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24688 Streptomyces ramocissimus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23149 Callistemon coccineus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13455 Hemiselmis virescens Species Hemiselmidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24813 Agardhiella tenera Species Solieriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24874 Croton geayi Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23657 Ophiocordyceps heteropoda Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24406 Rhizophora tagal Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27093 Kniphofia foliosa Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18875 Aconitum contortum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25226 Kalanchoe spathulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23837 Rubus laciniatus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24969 Ageratum mexicanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24268 Pteryxia terebinthina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21483 0nomuraea dietziae Species Streptosporangiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO23288 Justicia betonica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24118 Buxus hildebrandtii Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24589 Grindelia discoidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19716 Uvaria lucida Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21799 Bacillus litoralis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25031 Petunia nyctaginiflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24021 Eucryphia cordifolia Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22924 Bombus terrestris Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25068 Zebrina pendula Species Enidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17445 Streptomyces corchorusii Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO21242 Neolitsea villosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28259 Viguiera pinnatilobata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23660 Alpinia zerumbet Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23375 Hypericum reptans Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24191 Drypetes tessmanniana Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24493 Echinacea simulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27277 Stenocarpella maydis Species Diaporthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18045 Holothuria atra Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24754 Tsitsikamma favus Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24456 Salvia lavandulifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24937 Callicarpa acuminata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 11.01 ug.mL-1 PMID[483040]

☑ 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 NPC60951 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
0.8556 High Similarity NPC94337
0.837 Intermediate Similarity NPC264378
0.8256 Intermediate Similarity NPC476678
0.8191 Intermediate Similarity NPC112613
0.8191 Intermediate Similarity NPC207885
0.8065 Intermediate Similarity NPC471916
0.8 Intermediate Similarity NPC113393
0.7978 Intermediate Similarity NPC307298
0.7935 Intermediate Similarity NPC38830
0.7841 Intermediate Similarity NPC96621
0.7826 Intermediate Similarity NPC271652
0.7791 Intermediate Similarity NPC282293
0.7742 Intermediate Similarity NPC470697
0.77 Intermediate Similarity NPC322903
0.7692 Intermediate Similarity NPC280833
0.7653 Intermediate Similarity NPC131366
0.7647 Intermediate Similarity NPC178852
0.7614 Intermediate Similarity NPC222358
0.7609 Intermediate Similarity NPC161638
0.7582 Intermediate Similarity NPC241507
0.7558 Intermediate Similarity NPC281138
0.7558 Intermediate Similarity NPC150646
0.7551 Intermediate Similarity NPC478176
0.7551 Intermediate Similarity NPC80781
0.7527 Intermediate Similarity NPC49420
0.7526 Intermediate Similarity NPC469551
0.75 Intermediate Similarity NPC73995
0.75 Intermediate Similarity NPC151488
0.7476 Intermediate Similarity NPC317107
0.7473 Intermediate Similarity NPC272039
0.7473 Intermediate Similarity NPC220930
0.7451 Intermediate Similarity NPC87335
0.7444 Intermediate Similarity NPC177932
0.7439 Intermediate Similarity NPC173321
0.7419 Intermediate Similarity NPC474209
0.7419 Intermediate Similarity NPC152467
0.7419 Intermediate Similarity NPC477684
0.7419 Intermediate Similarity NPC475823
0.7419 Intermediate Similarity NPC8062
0.7416 Intermediate Similarity NPC251475
0.7416 Intermediate Similarity NPC169941
0.7404 Intermediate Similarity NPC317687
0.7391 Intermediate Similarity NPC475001
0.7391 Intermediate Similarity NPC215831
0.7391 Intermediate Similarity NPC185059
0.7368 Intermediate Similarity NPC477439
0.7363 Intermediate Similarity NPC250981
0.734 Intermediate Similarity NPC248913
0.734 Intermediate Similarity NPC472953
0.734 Intermediate Similarity NPC73457
0.7333 Intermediate Similarity NPC159333
0.7333 Intermediate Similarity NPC40687
0.7333 Intermediate Similarity NPC33360
0.7333 Intermediate Similarity NPC30486
0.7326 Intermediate Similarity NPC316500
0.732 Intermediate Similarity NPC38530
0.732 Intermediate Similarity NPC84335
0.7292 Intermediate Similarity NPC477437
0.7292 Intermediate Similarity NPC316215
0.7292 Intermediate Similarity NPC477438
0.729 Intermediate Similarity NPC243065
0.7263 Intermediate Similarity NPC477435
0.7263 Intermediate Similarity NPC477436
0.7245 Intermediate Similarity NPC316598
0.7234 Intermediate Similarity NPC38952
0.7222 Intermediate Similarity NPC193198
0.7216 Intermediate Similarity NPC272411
0.7204 Intermediate Similarity NPC53454
0.7204 Intermediate Similarity NPC277771
0.7188 Intermediate Similarity NPC212812
0.7188 Intermediate Similarity NPC84893
0.7174 Intermediate Similarity NPC220478
0.7172 Intermediate Similarity NPC476299
0.7172 Intermediate Similarity NPC474012
0.7159 Intermediate Similarity NPC476177
0.7159 Intermediate Similarity NPC622
0.7159 Intermediate Similarity NPC276647
0.7158 Intermediate Similarity NPC166110
0.7158 Intermediate Similarity NPC473944
0.7158 Intermediate Similarity NPC472975
0.7158 Intermediate Similarity NPC26865
0.7157 Intermediate Similarity NPC1679
0.7157 Intermediate Similarity NPC472645
0.7156 Intermediate Similarity NPC470495
0.7143 Intermediate Similarity NPC2049
0.7143 Intermediate Similarity NPC84790
0.7143 Intermediate Similarity NPC474359
0.7129 Intermediate Similarity NPC320154
0.7128 Intermediate Similarity NPC142159
0.7128 Intermediate Similarity NPC95364
0.7126 Intermediate Similarity NPC197659
0.7113 Intermediate Similarity NPC476519
0.7113 Intermediate Similarity NPC183012
0.7113 Intermediate Similarity NPC227494
0.7111 Intermediate Similarity NPC93590
0.7111 Intermediate Similarity NPC70479
0.7111 Intermediate Similarity NPC178676
0.71 Intermediate Similarity NPC472643
0.7087 Intermediate Similarity NPC474716
0.7083 Intermediate Similarity NPC476597
0.7083 Intermediate Similarity NPC248193
0.7083 Intermediate Similarity NPC476598
0.7079 Intermediate Similarity NPC104120
0.7079 Intermediate Similarity NPC157895
0.7079 Intermediate Similarity NPC172013
0.7079 Intermediate Similarity NPC148685
0.7065 Intermediate Similarity NPC478245
0.7065 Intermediate Similarity NPC133652
0.7065 Intermediate Similarity NPC70685
0.7065 Intermediate Similarity NPC15807
0.7065 Intermediate Similarity NPC79573
0.7065 Intermediate Similarity NPC189311
0.7065 Intermediate Similarity NPC110405
0.7064 Intermediate Similarity NPC240509
0.7059 Intermediate Similarity NPC247586
0.7053 Intermediate Similarity NPC223093
0.7045 Intermediate Similarity NPC207772
0.7045 Intermediate Similarity NPC476808
0.7045 Intermediate Similarity NPC23778
0.7041 Intermediate Similarity NPC476797
0.7041 Intermediate Similarity NPC472363
0.7041 Intermediate Similarity NPC154526
0.7041 Intermediate Similarity NPC472362
0.7037 Intermediate Similarity NPC270478
0.7033 Intermediate Similarity NPC66764
0.7033 Intermediate Similarity NPC110150
0.7033 Intermediate Similarity NPC64600
0.7033 Intermediate Similarity NPC194637
0.7033 Intermediate Similarity NPC22611
0.703 Intermediate Similarity NPC39996
0.7021 Intermediate Similarity NPC475902
0.7021 Intermediate Similarity NPC58271
0.7021 Intermediate Similarity NPC230387
0.7021 Intermediate Similarity NPC80335
0.7021 Intermediate Similarity NPC477128
0.7019 Intermediate Similarity NPC469916
0.7019 Intermediate Similarity NPC472439
0.701 Intermediate Similarity NPC148463
0.701 Intermediate Similarity NPC474555
0.701 Intermediate Similarity NPC477130
0.701 Intermediate Similarity NPC477129
0.701 Intermediate Similarity NPC476596
0.7009 Intermediate Similarity NPC122056
0.7 Intermediate Similarity NPC117685
0.7 Intermediate Similarity NPC472644
0.7 Intermediate Similarity NPC46761
0.7 Intermediate Similarity NPC474085
0.7 Intermediate Similarity NPC472972
0.7 Intermediate Similarity NPC475665
0.7 Intermediate Similarity NPC174314
0.699 Remote Similarity NPC32006
0.699 Remote Similarity NPC85529
0.6989 Remote Similarity NPC196381
0.6989 Remote Similarity NPC202394
0.6989 Remote Similarity NPC472974
0.6981 Remote Similarity NPC470960
0.6979 Remote Similarity NPC116726
0.6979 Remote Similarity NPC193396
0.6979 Remote Similarity NPC32944
0.6979 Remote Similarity NPC478243
0.6979 Remote Similarity NPC233345
0.6979 Remote Similarity NPC478244
0.6979 Remote Similarity NPC186363
0.6979 Remote Similarity NPC190442
0.6977 Remote Similarity NPC470299
0.697 Remote Similarity NPC151681
0.697 Remote Similarity NPC110937
0.697 Remote Similarity NPC175351
0.697 Remote Similarity NPC121402
0.697 Remote Similarity NPC224356
0.697 Remote Similarity NPC132753
0.6966 Remote Similarity NPC308038
0.6966 Remote Similarity NPC471740
0.6966 Remote Similarity NPC268502
0.6966 Remote Similarity NPC254996
0.6961 Remote Similarity NPC473283
0.6961 Remote Similarity NPC473624
0.6961 Remote Similarity NPC475526
0.6961 Remote Similarity NPC159533
0.6961 Remote Similarity NPC329345
0.6957 Remote Similarity NPC120158
0.6957 Remote Similarity NPC475193
0.6957 Remote Similarity NPC219011
0.6952 Remote Similarity NPC20192
0.6947 Remote Similarity NPC469323
0.6947 Remote Similarity NPC284561
0.6947 Remote Similarity NPC173042
0.6944 Remote Similarity NPC238667
0.6939 Remote Similarity NPC476245
0.6939 Remote Similarity NPC295347
0.6932 Remote Similarity NPC257666
0.6932 Remote Similarity NPC266193
0.6932 Remote Similarity NPC189206
0.6931 Remote Similarity NPC476478
0.6931 Remote Similarity NPC93744
0.6931 Remote Similarity NPC472637
0.6931 Remote Similarity NPC470184
0.6931 Remote Similarity NPC476888
0.6923 Remote Similarity NPC475510
0.6923 Remote Similarity NPC473165

  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 NPC60951 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
0.7444 Intermediate Similarity NPD1694 Approved
0.6818 Remote Similarity NPD7115 Discovery
0.6804 Remote Similarity NPD5693 Phase 1
0.6762 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6702 Remote Similarity NPD1696 Phase 3
0.6667 Remote Similarity NPD5737 Approved
0.6667 Remote Similarity NPD6672 Approved
0.6636 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6632 Remote Similarity NPD3618 Phase 1
0.6574 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6562 Remote Similarity NPD3573 Approved
0.6559 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6509 Remote Similarity NPD6675 Approved
0.6509 Remote Similarity NPD6402 Approved
0.6509 Remote Similarity NPD7128 Approved
0.6509 Remote Similarity NPD6008 Approved
0.6509 Remote Similarity NPD5739 Approved
0.65 Remote Similarity NPD7901 Clinical (unspecified phase)
0.65 Remote Similarity NPD7900 Approved
0.65 Remote Similarity NPD7748 Approved
0.6484 Remote Similarity NPD3617 Approved
0.6471 Remote Similarity NPD4755 Approved
0.6458 Remote Similarity NPD7521 Approved
0.6458 Remote Similarity NPD7334 Approved
0.6458 Remote Similarity NPD6409 Approved
0.6458 Remote Similarity NPD6684 Approved
0.6458 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6458 Remote Similarity NPD7146 Approved
0.6458 Remote Similarity NPD5330 Approved
0.6449 Remote Similarity NPD5697 Approved
0.6449 Remote Similarity NPD5701 Approved
0.6436 Remote Similarity NPD5695 Phase 3
0.6429 Remote Similarity NPD6904 Approved
0.6429 Remote Similarity NPD6673 Approved
0.6429 Remote Similarity NPD5328 Approved
0.6429 Remote Similarity NPD6080 Approved
0.6408 Remote Similarity NPD4225 Approved
0.64 Remote Similarity NPD4202 Approved
0.6389 Remote Similarity NPD7320 Approved
0.6389 Remote Similarity NPD6899 Approved
0.6389 Remote Similarity NPD6881 Approved
0.6389 Remote Similarity NPD6011 Approved
0.6383 Remote Similarity NPD3667 Approved
0.6381 Remote Similarity NPD5211 Phase 2
0.6373 Remote Similarity NPD5222 Approved
0.6373 Remote Similarity NPD5221 Approved
0.6373 Remote Similarity NPD4697 Phase 3
0.6373 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5692 Phase 3
0.6346 Remote Similarity NPD4696 Approved
0.6346 Remote Similarity NPD5285 Approved
0.6346 Remote Similarity NPD5286 Approved
0.6346 Remote Similarity NPD4700 Approved
0.6344 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6344 Remote Similarity NPD4695 Discontinued
0.6333 Remote Similarity NPD8039 Approved
0.633 Remote Similarity NPD6373 Approved
0.633 Remote Similarity NPD6012 Approved
0.633 Remote Similarity NPD6014 Approved
0.633 Remote Similarity NPD6372 Approved
0.633 Remote Similarity NPD6013 Approved
0.6327 Remote Similarity NPD6903 Approved
0.6327 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6311 Remote Similarity NPD5173 Approved
0.6311 Remote Similarity NPD6083 Phase 2
0.6311 Remote Similarity NPD7902 Approved
0.6311 Remote Similarity NPD6084 Phase 2
0.63 Remote Similarity NPD6079 Approved
0.63 Remote Similarity NPD7515 Phase 2
0.63 Remote Similarity NPD6050 Approved
0.63 Remote Similarity NPD5694 Approved
0.6289 Remote Similarity NPD6098 Approved
0.6289 Remote Similarity NPD5279 Phase 3
0.6286 Remote Similarity NPD5223 Approved
0.6275 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6273 Remote Similarity NPD7102 Approved
0.6273 Remote Similarity NPD7290 Approved
0.6273 Remote Similarity NPD6883 Approved
0.6263 Remote Similarity NPD4753 Phase 2
0.6262 Remote Similarity NPD5141 Approved
0.625 Remote Similarity NPD3665 Phase 1
0.625 Remote Similarity NPD3666 Approved
0.625 Remote Similarity NPD5696 Approved
0.625 Remote Similarity NPD4786 Approved
0.625 Remote Similarity NPD7638 Approved
0.625 Remote Similarity NPD3668 Phase 3
0.625 Remote Similarity NPD4197 Approved
0.625 Remote Similarity NPD3133 Approved
0.6235 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6226 Remote Similarity NPD5224 Approved
0.6226 Remote Similarity NPD5226 Approved
0.6226 Remote Similarity NPD5225 Approved
0.6226 Remote Similarity NPD4633 Approved
0.6216 Remote Similarity NPD6649 Approved
0.6216 Remote Similarity NPD6869 Approved
0.6216 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6216 Remote Similarity NPD6847 Approved
0.6216 Remote Similarity NPD6650 Approved
0.6216 Remote Similarity NPD6617 Approved
0.6216 Remote Similarity NPD8130 Phase 1
0.619 Remote Similarity NPD7640 Approved
0.619 Remote Similarity NPD7639 Approved
0.6186 Remote Similarity NPD5329 Approved
0.6176 Remote Similarity NPD6001 Approved
0.6176 Remote Similarity NPD5282 Discontinued
0.6168 Remote Similarity NPD5175 Approved
0.6168 Remote Similarity NPD5174 Approved
0.6168 Remote Similarity NPD4754 Approved
0.6163 Remote Similarity NPD3704 Approved
0.6161 Remote Similarity NPD8297 Approved
0.6161 Remote Similarity NPD6882 Approved
0.6154 Remote Similarity NPD5959 Approved
0.6126 Remote Similarity NPD4634 Approved
0.6122 Remote Similarity NPD5690 Phase 2
0.6122 Remote Similarity NPD4694 Approved
0.6122 Remote Similarity NPD4623 Approved
0.6122 Remote Similarity NPD4519 Discontinued
0.6122 Remote Similarity NPD5280 Approved
0.6117 Remote Similarity NPD5654 Approved
0.6078 Remote Similarity NPD6399 Phase 3
0.6075 Remote Similarity NPD7632 Discontinued
0.6068 Remote Similarity NPD6054 Approved
0.6068 Remote Similarity NPD6319 Approved
0.6068 Remote Similarity NPD6059 Approved
0.6055 Remote Similarity NPD4768 Approved
0.6055 Remote Similarity NPD4767 Approved
0.6047 Remote Similarity NPD7341 Phase 2
0.6042 Remote Similarity NPD4221 Approved
0.6042 Remote Similarity NPD4223 Phase 3
0.6042 Remote Similarity NPD5209 Approved
0.6017 Remote Similarity NPD6016 Approved
0.6017 Remote Similarity NPD6015 Approved
0.6 Remote Similarity NPD5208 Approved
0.6 Remote Similarity NPD6274 Approved
0.598 Remote Similarity NPD6411 Approved
0.5977 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5966 Remote Similarity NPD6370 Approved
0.5966 Remote Similarity NPD5988 Approved
0.5962 Remote Similarity NPD5210 Approved
0.5962 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5962 Remote Similarity NPD4629 Approved
0.5948 Remote Similarity NPD6317 Approved
0.5946 Remote Similarity NPD5128 Approved
0.5946 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5946 Remote Similarity NPD4730 Approved
0.5946 Remote Similarity NPD4729 Approved
0.5941 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5922 Remote Similarity NPD5133 Approved
0.5922 Remote Similarity NPD5778 Approved
0.5922 Remote Similarity NPD5779 Approved
0.5897 Remote Similarity NPD6313 Approved
0.5897 Remote Similarity NPD6335 Approved
0.5897 Remote Similarity NPD6314 Approved
0.5882 Remote Similarity NPD5785 Approved
0.5882 Remote Similarity NPD46 Approved
0.5882 Remote Similarity NPD6698 Approved
0.5882 Remote Similarity NPD5207 Approved
0.5868 Remote Similarity NPD7492 Approved
0.5862 Remote Similarity NPD6868 Approved
0.5859 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5847 Remote Similarity NPD7100 Approved
0.5847 Remote Similarity NPD7101 Approved
0.5841 Remote Similarity NPD5248 Approved
0.5841 Remote Similarity NPD5169 Approved
0.5841 Remote Similarity NPD5251 Approved
0.5841 Remote Similarity NPD5135 Approved
0.5841 Remote Similarity NPD5250 Approved
0.5841 Remote Similarity NPD5249 Phase 3
0.5841 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5841 Remote Similarity NPD5247 Approved
0.5833 Remote Similarity NPD4159 Approved
0.5826 Remote Similarity NPD4632 Approved
0.582 Remote Similarity NPD6616 Approved
0.5812 Remote Similarity NPD6009 Approved
0.5812 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5804 Remote Similarity NPD5168 Approved
0.58 Remote Similarity NPD5205 Approved
0.58 Remote Similarity NPD4690 Approved
0.58 Remote Similarity NPD4693 Phase 3
0.58 Remote Similarity NPD4138 Approved
0.58 Remote Similarity NPD4689 Approved
0.58 Remote Similarity NPD4688 Approved
0.5795 Remote Similarity NPD7331 Phase 2
0.5789 Remote Similarity NPD5215 Approved
0.5789 Remote Similarity NPD5217 Approved
0.5789 Remote Similarity NPD5216 Approved
0.5789 Remote Similarity NPD5127 Approved
0.5785 Remote Similarity NPD7604 Phase 2
0.5785 Remote Similarity NPD8328 Phase 3
0.5784 Remote Similarity NPD1695 Approved
0.5784 Remote Similarity NPD6051 Approved
0.5784 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5784 Remote Similarity NPD6101 Approved
0.5778 Remote Similarity NPD4137 Phase 3
0.5773 Remote Similarity NPD4139 Approved
0.5773 Remote Similarity NPD4692 Approved
0.5772 Remote Similarity NPD7078 Approved
0.5772 Remote Similarity NPD8293 Discontinued
0.575 Remote Similarity NPD6908 Approved
0.575 Remote Similarity NPD5983 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