Structure

Physi-Chem Properties

Molecular Weight:  390.2
Volume:  397.038
LogP:  2.273
LogD:  1.661
LogS:  -3.682
# Rotatable Bonds:  3
TPSA:  104.06
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.488
Synthetic Accessibility Score:  4.988
Fsp3:  0.727
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:  -4.837
MDCK Permeability:  3.0421861083596013e-05
Pgp-inhibitor:  0.257
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.484
20% Bioavailability (F20%):  0.052
30% Bioavailability (F30%):  0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.823
Plasma Protein Binding (PPB):  33.862098693847656%
Volume Distribution (VD):  0.769
Pgp-substrate:  57.8818244934082%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.107
CYP2C19-inhibitor:  0.031
CYP2C19-substrate:  0.652
CYP2C9-inhibitor:  0.022
CYP2C9-substrate:  0.078
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.121
CYP3A4-inhibitor:  0.114
CYP3A4-substrate:  0.205

ADMET: Excretion

Clearance (CL):  1.765
Half-life (T1/2):  0.616

ADMET: Toxicity

hERG Blockers:  0.217
Human Hepatotoxicity (H-HT):  0.791
Drug-inuced Liver Injury (DILI):  0.577
AMES Toxicity:  0.044
Rat Oral Acute Toxicity:  0.976
Maximum Recommended Daily Dose:  0.983
Skin Sensitization:  0.808
Carcinogencity:  0.292
Eye Corrosion:  0.003
Eye Irritation:  0.02
Respiratory Toxicity:  0.973

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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  Natural Product: NPC153036

Natural Product ID:  NPC153036
Common Name*:   Prostratin
IUPAC Name:   n.a.
Synonyms:   12-Deoxyphorbol-13-Acetate; Prostratin
Standard InCHIKey:  BOJKFRKNLSCGHY-HXGSDTCMSA-N
Standard InCHI:  InChI=1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1
SMILES:  OCC1=C[C@H]2[C@H]3[C@@](C3(C)C)(OC(=O)C)C[C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL170518
PubChem CID:   454217
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0002875] Tigliane and ingenane diterpenoids
            • [CHEMONTID:0002906] Phorbol esters

*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
NPO32973 homoalanthus nutans Species n.a. n.a. n.a. Samoa n.a. PMID[11430019]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[16792421]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[17512094]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19376614]
NPO13882 Euphorbia grandicornis Species Euphorbiaceae Eukaryota n.a. aerial part n.a. PMID[21319774]
NPO19424 Trigonostemon howii Species Euphorbiaceae Eukaryota n.a. twig n.a. PMID[21520897]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota whole plants Panshi, Jilin Province, China 2009-JUN PMID[21534540]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. whole plant n.a. PMID[21534540]
NPO19424 Trigonostemon howii Species Euphorbiaceae Eukaryota Stems n.a. n.a. PMID[23148674]
NPO19424 Trigonostemon howii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[23215460]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[24660966]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[25453801]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[26702644]
NPO13882 Euphorbia grandicornis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[27731641]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[28383891]
NPO21274 Euphorbia semiperfoliata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[28925702]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[29148766]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31184480]
NPO19062 Euphorbia coerulescens Species Euphorbiaceae Eukaryota latices South African n.a. PMID[3236005]
NPO25960 Euphorbia triangularis Species Euphorbiaceae Eukaryota latices South African n.a. PMID[3236005]
NPO32447 euphorbia ledienii Species Euphorbiaceae Eukaryota latices South African n.a. PMID[3236005]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21274 Euphorbia semiperfoliata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19062 Euphorbia coerulescens Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19424 Trigonostemon howii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13882 Euphorbia grandicornis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25960 Euphorbia triangularis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae 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
NPT517 Cell Line Panel NCI-60 (60 carcinoma cell lines) Homo sapiens GI50 = 7000.0 nM PMID[522445]
NPT407 Cell Line COLO 205 Homo sapiens GI50 = 1900.0 nM PMID[522445]
NPT4629 Individual Protein Protein kinase C alpha Bos taurus Ki = 4.8 nM PMID[522446]
NPT1556 Individual Protein Epidermal growth factor receptor erbB1 Mus musculus Effective concentration = 220.0 nM PMID[522447]
NPT4727 Cell Line C3H 10T1/2 Mus musculus Effective concentration = 1100.0 nM PMID[522447]
NPT517 Cell Line Panel NCI-60 (60 carcinoma cell lines) Homo sapiens Log 1/GI50 = 3.0 n.a. PMID[522448]
NPT91 Cell Line KB Homo sapiens IC50 = 1000.0 ug.mL-1 PMID[522450]
NPT4651 Cell Line Ramos Homo sapiens IC50 = 0.056 ug.mL-1 PMID[522452]
NPT1452 Cell Line C8166 Homo sapiens CC50 > 510.0 nM PMID[522453]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = -10.45 % PMID[522454]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 79000.0 nM PMID[522455]
NPT460 Cell Line MT2 Homo sapiens CC50 > 50000.0 nM PMID[522459]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 79000.0 nM PMID[522459]
NPT2 Others Unspecified GI50 = 790.0 nM PMID[522445]
NPT27 Others Unspecified GI50 = 10000.0 nM PMID[522445]
NPT35 Others n.a. LogP = 1.9 n.a. PMID[522446]
NPT2 Others Unspecified Ki = 12.5 nM PMID[522447]
NPT727 Protein Family Protein kinase C, PKC; classical/novel Homo sapiens Ki = 210.0 nM PMID[522447]
NPT727 Protein Family Protein kinase C, PKC; classical/novel Homo sapiens Ki = 190.0 nM PMID[522447]
NPT32 Organism Mus musculus Mus musculus Activity > 7.0 nmol PMID[522449]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 <= 132.0 nM PMID[522451]
NPT27 Others Unspecified EC50 = 250.0 n.a. PMID[522451]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 0.06 nM PMID[522453]
NPT27 Others Unspecified Ratio CC50/EC50 > 8500.0 n.a. PMID[522453]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 3.93 % PMID[522454]
NPT856 Organism Semliki forest virus Semliki forest virus EC50 > 256000.0 nM PMID[522455]
NPT338 Organism Sindbis virus Sindbis virus EC50 > 256000.0 nM PMID[522455]
NPT2 Others Unspecified Ratio CC50/EC50 = 30.3 n.a. PMID[522455]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 2600.0 nM PMID[522455]
NPT2 Others Unspecified Ratio CC50/EC50 = 171.0 n.a. PMID[522456]
NPT2 Others Unspecified Ratio CC50/EC50 = 22.8 n.a. PMID[522456]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 2700.0 nM PMID[522456]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 1900.0 nM PMID[522456]
NPT332 Organism Human immunodeficiency virus type 2 (ISOLATE ROD) Human immunodeficiency virus type 2 (ISOLATE ROD) EC50 = 900.0 nM PMID[522456]
NPT2 Others Unspecified Ratio CC50/EC50 > 370.0 n.a. PMID[522456]
NPT316 Protein Family Protein kinase C (PKC) Homo sapiens EC50 = 910.0 nM PMID[522457]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC > 400.0 ug.mL-1 PMID[522458]
NPT1114 Organism Human immunodeficiency virus Human immunodeficiency virus EC50 = 226.0 nM PMID[522459]
NPT2 Others Unspecified Ratio CC50/EC50 > 22.0 n.a. PMID[522459]
NPT20632 ORGANISM Chikungunya virus Chikungunya virus EC50 = 2600.0 nM PMID[522459]
NPT2 Others Unspecified Ratio CC50/EC50 = 30.0 n.a. PMID[522459]
NPT20632 ORGANISM Chikungunya virus Chikungunya virus EC50 = 500.0 nM PMID[522460]
NPT20632 ORGANISM Chikungunya virus Chikungunya virus EC50 = 200.0 nM PMID[522460]
NPT20632 ORGANISM Chikungunya virus Chikungunya virus EC50 = 400.0 nM PMID[522460]
NPT20632 ORGANISM Chikungunya virus Chikungunya virus EC50 = 300.0 nM PMID[522460]
NPT20632 ORGANISM Chikungunya virus Chikungunya virus EC50 = 7100.0 nM PMID[522460]
NPT20632 ORGANISM Chikungunya virus Chikungunya virus EC50 = 7600.0 nM PMID[522460]
NPT20632 ORGANISM Chikungunya virus Chikungunya virus EC50 = 8000.0 nM PMID[522460]

☑ 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 NPC153036 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
0.9902 High Similarity NPC158523
0.9902 High Similarity NPC475937
0.9712 High Similarity NPC71889
0.9619 High Similarity NPC474872
0.9519 High Similarity NPC474871
0.9519 High Similarity NPC260786
0.9519 High Similarity NPC96739
0.9519 High Similarity NPC174471
0.9439 High Similarity NPC153651
0.9439 High Similarity NPC156252
0.9429 High Similarity NPC101825
0.9429 High Similarity NPC475391
0.9429 High Similarity NPC89227
0.9429 High Similarity NPC265499
0.9429 High Similarity NPC17138
0.9429 High Similarity NPC151216
0.9429 High Similarity NPC221511
0.9429 High Similarity NPC170212
0.9429 High Similarity NPC215643
0.9352 High Similarity NPC171905
0.9352 High Similarity NPC472758
0.9352 High Similarity NPC472760
0.9352 High Similarity NPC472397
0.9352 High Similarity NPC471125
0.934 High Similarity NPC477091
0.934 High Similarity NPC474937
0.9266 High Similarity NPC255081
0.9266 High Similarity NPC5991
0.9266 High Similarity NPC275696
0.9266 High Similarity NPC180640
0.9266 High Similarity NPC471108
0.9266 High Similarity NPC5989
0.9266 High Similarity NPC22628
0.9182 High Similarity NPC471128
0.9182 High Similarity NPC157252
0.9182 High Similarity NPC145182
0.9182 High Similarity NPC185876
0.9182 High Similarity NPC19336
0.9182 High Similarity NPC471126
0.9159 High Similarity NPC472757
0.9099 High Similarity NPC52839
0.9099 High Similarity NPC472401
0.9074 High Similarity NPC472400
0.9018 High Similarity NPC19464
0.8991 High Similarity NPC471127
0.8991 High Similarity NPC234858
0.8991 High Similarity NPC154363
0.8962 High Similarity NPC163004
0.8938 High Similarity NPC472399
0.8909 High Similarity NPC10721
0.886 High Similarity NPC145238
0.885 High Similarity NPC162009
0.885 High Similarity NPC257017
0.875 High Similarity NPC236918
0.875 High Similarity NPC156745
0.8673 High Similarity NPC329080
0.8673 High Similarity NPC475885
0.8673 High Similarity NPC472759
0.8661 High Similarity NPC124676
0.8661 High Similarity NPC146280
0.8621 High Similarity NPC222307
0.8475 Intermediate Similarity NPC270109
0.8319 Intermediate Similarity NPC236999
0.822 Intermediate Similarity NPC473919
0.822 Intermediate Similarity NPC473709
0.8208 Intermediate Similarity NPC470074
0.8158 Intermediate Similarity NPC179626
0.8145 Intermediate Similarity NPC243902
0.8142 Intermediate Similarity NPC474271
0.8136 Intermediate Similarity NPC473802
0.8083 Intermediate Similarity NPC471940
0.8053 Intermediate Similarity NPC71348
0.8051 Intermediate Similarity NPC222688
0.8037 Intermediate Similarity NPC306856
0.8036 Intermediate Similarity NPC5103
0.8018 Intermediate Similarity NPC322903
0.8 Intermediate Similarity NPC270958
0.8 Intermediate Similarity NPC471939
0.7982 Intermediate Similarity NPC202889
0.7982 Intermediate Similarity NPC478057
0.7967 Intermediate Similarity NPC189393
0.7967 Intermediate Similarity NPC90814
0.7963 Intermediate Similarity NPC81530
0.7949 Intermediate Similarity NPC472667
0.7949 Intermediate Similarity NPC472933
0.7946 Intermediate Similarity NPC273433
0.7909 Intermediate Similarity NPC72255
0.7905 Intermediate Similarity NPC181393
0.7905 Intermediate Similarity NPC217624
0.7903 Intermediate Similarity NPC476111
0.7895 Intermediate Similarity NPC472002
0.789 Intermediate Similarity NPC476081
0.789 Intermediate Similarity NPC162973
0.789 Intermediate Similarity NPC118405
0.789 Intermediate Similarity NPC136289
0.7881 Intermediate Similarity NPC143755
0.7876 Intermediate Similarity NPC257240
0.787 Intermediate Similarity NPC47024
0.787 Intermediate Similarity NPC474718
0.787 Intermediate Similarity NPC476274
0.787 Intermediate Similarity NPC472972
0.7863 Intermediate Similarity NPC251310
0.7863 Intermediate Similarity NPC118638
0.7857 Intermediate Similarity NPC29827
0.7857 Intermediate Similarity NPC476479
0.785 Intermediate Similarity NPC170131
0.7845 Intermediate Similarity NPC148458
0.7838 Intermediate Similarity NPC472645
0.7826 Intermediate Similarity NPC472926
0.7826 Intermediate Similarity NPC194100
0.7826 Intermediate Similarity NPC962
0.7826 Intermediate Similarity NPC25909
0.7826 Intermediate Similarity NPC469454
0.7826 Intermediate Similarity NPC469463
0.7826 Intermediate Similarity NPC469496
0.7807 Intermediate Similarity NPC304180
0.7807 Intermediate Similarity NPC179798
0.7807 Intermediate Similarity NPC214797
0.7807 Intermediate Similarity NPC118860
0.7807 Intermediate Similarity NPC231589
0.7807 Intermediate Similarity NPC317107
0.7798 Intermediate Similarity NPC471412
0.7798 Intermediate Similarity NPC476223
0.7798 Intermediate Similarity NPC476240
0.7798 Intermediate Similarity NPC115862
0.7798 Intermediate Similarity NPC237190
0.7798 Intermediate Similarity NPC224720
0.7797 Intermediate Similarity NPC268958
0.7788 Intermediate Similarity NPC241927
0.7788 Intermediate Similarity NPC141350
0.7788 Intermediate Similarity NPC258543
0.7787 Intermediate Similarity NPC473253
0.7778 Intermediate Similarity NPC222011
0.7778 Intermediate Similarity NPC472927
0.7778 Intermediate Similarity NPC216478
0.7778 Intermediate Similarity NPC472934
0.7778 Intermediate Similarity NPC471854
0.7768 Intermediate Similarity NPC44063
0.7768 Intermediate Similarity NPC472925
0.7768 Intermediate Similarity NPC67321
0.7768 Intermediate Similarity NPC187435
0.7768 Intermediate Similarity NPC3316
0.7768 Intermediate Similarity NPC144854
0.776 Intermediate Similarity NPC469674
0.776 Intermediate Similarity NPC469673
0.7757 Intermediate Similarity NPC202833
0.7757 Intermediate Similarity NPC234993
0.7757 Intermediate Similarity NPC284518
0.7757 Intermediate Similarity NPC134072
0.7748 Intermediate Similarity NPC118911
0.7748 Intermediate Similarity NPC258532
0.7742 Intermediate Similarity NPC220757
0.7742 Intermediate Similarity NPC196921
0.7739 Intermediate Similarity NPC317687
0.7739 Intermediate Similarity NPC152117
0.7739 Intermediate Similarity NPC76550
0.7739 Intermediate Similarity NPC170487
0.7739 Intermediate Similarity NPC474516
0.7739 Intermediate Similarity NPC234042
0.7739 Intermediate Similarity NPC123855
0.7731 Intermediate Similarity NPC109973
0.7727 Intermediate Similarity NPC119601
0.7727 Intermediate Similarity NPC22388
0.7727 Intermediate Similarity NPC308726
0.7727 Intermediate Similarity NPC109195
0.7727 Intermediate Similarity NPC470840
0.7727 Intermediate Similarity NPC39996
0.7727 Intermediate Similarity NPC475038
0.7719 Intermediate Similarity NPC473036
0.7719 Intermediate Similarity NPC477103
0.7719 Intermediate Similarity NPC272898
0.7714 Intermediate Similarity NPC473675
0.7706 Intermediate Similarity NPC471413
0.7706 Intermediate Similarity NPC327431
0.7706 Intermediate Similarity NPC471041
0.7705 Intermediate Similarity NPC15095
0.7699 Intermediate Similarity NPC275539
0.7699 Intermediate Similarity NPC189075
0.7699 Intermediate Similarity NPC154608
0.7699 Intermediate Similarity NPC102843
0.7699 Intermediate Similarity NPC192813
0.7699 Intermediate Similarity NPC277017
0.7698 Intermediate Similarity NPC476823
0.7692 Intermediate Similarity NPC266728
0.7692 Intermediate Similarity NPC49492
0.7692 Intermediate Similarity NPC270478
0.7692 Intermediate Similarity NPC176840
0.7686 Intermediate Similarity NPC469789
0.7685 Intermediate Similarity NPC69385
0.7685 Intermediate Similarity NPC473963
0.7685 Intermediate Similarity NPC474343
0.768 Intermediate Similarity NPC180902
0.768 Intermediate Similarity NPC475139
0.768 Intermediate Similarity NPC34963
0.7679 Intermediate Similarity NPC257353
0.7679 Intermediate Similarity NPC60315
0.7679 Intermediate Similarity NPC1679
0.7679 Intermediate Similarity NPC314244
0.7679 Intermediate Similarity NPC179891
0.7679 Intermediate Similarity NPC469607

  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 NPC153036 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
0.7876 Intermediate Similarity NPD6371 Approved
0.7768 Intermediate Similarity NPD5697 Approved
0.7699 Intermediate Similarity NPD6881 Approved
0.7699 Intermediate Similarity NPD6899 Approved
0.7679 Intermediate Similarity NPD5739 Approved
0.7679 Intermediate Similarity NPD6675 Approved
0.7679 Intermediate Similarity NPD7128 Approved
0.7679 Intermediate Similarity NPD6402 Approved
0.7652 Intermediate Similarity NPD6650 Approved
0.7652 Intermediate Similarity NPD6649 Approved
0.7632 Intermediate Similarity NPD6014 Approved
0.7632 Intermediate Similarity NPD6372 Approved
0.7632 Intermediate Similarity NPD6012 Approved
0.7632 Intermediate Similarity NPD6373 Approved
0.7632 Intermediate Similarity NPD6013 Approved
0.7611 Intermediate Similarity NPD5701 Approved
0.7568 Intermediate Similarity NPD5211 Phase 2
0.7565 Intermediate Similarity NPD7290 Approved
0.7565 Intermediate Similarity NPD6883 Approved
0.7565 Intermediate Similarity NPD7102 Approved
0.7544 Intermediate Similarity NPD6011 Approved
0.7544 Intermediate Similarity NPD7320 Approved
0.7522 Intermediate Similarity NPD6008 Approved
0.7521 Intermediate Similarity NPD4632 Approved
0.75 Intermediate Similarity NPD6617 Approved
0.75 Intermediate Similarity NPD8130 Phase 1
0.75 Intermediate Similarity NPD6847 Approved
0.75 Intermediate Similarity NPD6869 Approved
0.7438 Intermediate Similarity NPD6319 Approved
0.7436 Intermediate Similarity NPD6882 Approved
0.7436 Intermediate Similarity NPD8297 Approved
0.7434 Intermediate Similarity NPD5141 Approved
0.7398 Intermediate Similarity NPD7604 Phase 2
0.7387 Intermediate Similarity NPD4696 Approved
0.7387 Intermediate Similarity NPD7639 Approved
0.7387 Intermediate Similarity NPD7640 Approved
0.7387 Intermediate Similarity NPD5286 Approved
0.7387 Intermediate Similarity NPD5285 Approved
0.7364 Intermediate Similarity NPD4755 Approved
0.7364 Intermediate Similarity NPD6084 Phase 2
0.7364 Intermediate Similarity NPD6083 Phase 2
0.7339 Intermediate Similarity NPD5695 Phase 3
0.7333 Intermediate Similarity NPD6009 Approved
0.7333 Intermediate Similarity NPD7115 Discovery
0.7308 Intermediate Similarity NPD1696 Phase 3
0.7297 Intermediate Similarity NPD7638 Approved
0.7297 Intermediate Similarity NPD5696 Approved
0.7257 Intermediate Similarity NPD5225 Approved
0.7257 Intermediate Similarity NPD5226 Approved
0.7257 Intermediate Similarity NPD4633 Approved
0.7257 Intermediate Similarity NPD5224 Approved
0.725 Intermediate Similarity NPD6274 Approved
0.7236 Intermediate Similarity NPD5983 Phase 2
0.7232 Intermediate Similarity NPD4700 Approved
0.7203 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7492 Approved
0.7193 Intermediate Similarity NPD5175 Approved
0.7193 Intermediate Similarity NPD5174 Approved
0.7179 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD5223 Approved
0.7154 Intermediate Similarity NPD6054 Approved
0.7143 Intermediate Similarity NPD4225 Approved
0.7143 Intermediate Similarity NPD6616 Approved
0.7119 Intermediate Similarity NPD4634 Approved
0.7119 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6015 Approved
0.7097 Intermediate Similarity NPD6016 Approved
0.7091 Intermediate Similarity NPD5282 Discontinued
0.7087 Intermediate Similarity NPD7078 Approved
0.7073 Intermediate Similarity NPD7101 Approved
0.7073 Intermediate Similarity NPD7100 Approved
0.7049 Intermediate Similarity NPD6317 Approved
0.704 Intermediate Similarity NPD5988 Approved
0.704 Intermediate Similarity NPD6370 Approved
0.7037 Intermediate Similarity NPD4753 Phase 2
0.7031 Intermediate Similarity NPD7736 Approved
0.7027 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD5210 Approved
0.7027 Intermediate Similarity NPD4629 Approved
0.7018 Intermediate Similarity NPD5344 Discontinued
0.7016 Intermediate Similarity NPD6059 Approved
0.7009 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD6336 Discontinued
0.7 Intermediate Similarity NPD6053 Discontinued
0.7 Intermediate Similarity NPD6399 Phase 3
0.6992 Remote Similarity NPD6314 Approved
0.6992 Remote Similarity NPD6313 Approved
0.6992 Remote Similarity NPD6335 Approved
0.6964 Remote Similarity NPD4697 Phase 3
0.6964 Remote Similarity NPD5222 Approved
0.6964 Remote Similarity NPD5221 Approved
0.6964 Remote Similarity NPD5220 Clinical (unspecified phase)
0.696 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6953 Remote Similarity NPD8293 Discontinued
0.6949 Remote Similarity NPD5128 Approved
0.6949 Remote Similarity NPD4729 Approved
0.6949 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6949 Remote Similarity NPD4730 Approved
0.6923 Remote Similarity NPD4768 Approved
0.6923 Remote Similarity NPD4767 Approved
0.6903 Remote Similarity NPD5173 Approved
0.6903 Remote Similarity NPD7902 Approved
0.6897 Remote Similarity NPD4754 Approved
0.6881 Remote Similarity NPD1695 Approved
0.6875 Remote Similarity NPD7507 Approved
0.6864 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6847 Remote Similarity NPD4202 Approved
0.6833 Remote Similarity NPD5251 Approved
0.6833 Remote Similarity NPD5250 Approved
0.6833 Remote Similarity NPD5247 Approved
0.6833 Remote Similarity NPD5249 Phase 3
0.6833 Remote Similarity NPD5248 Approved
0.6825 Remote Similarity NPD6909 Approved
0.6825 Remote Similarity NPD6908 Approved
0.681 Remote Similarity NPD7632 Discontinued
0.6807 Remote Similarity NPD6686 Approved
0.6789 Remote Similarity NPD6672 Approved
0.6789 Remote Similarity NPD5737 Approved
0.6786 Remote Similarity NPD6001 Approved
0.6786 Remote Similarity NPD7748 Approved
0.6783 Remote Similarity NPD6648 Approved
0.6777 Remote Similarity NPD5217 Approved
0.6777 Remote Similarity NPD5215 Approved
0.6777 Remote Similarity NPD5216 Approved
0.6759 Remote Similarity NPD3618 Phase 1
0.6757 Remote Similarity NPD6079 Approved
0.6757 Remote Similarity NPD5284 Approved
0.6757 Remote Similarity NPD5693 Phase 1
0.6757 Remote Similarity NPD7515 Phase 2
0.6757 Remote Similarity NPD5281 Approved
0.6727 Remote Similarity NPD6904 Approved
0.6727 Remote Similarity NPD6673 Approved
0.6727 Remote Similarity NPD6080 Approved
0.6727 Remote Similarity NPD5328 Approved
0.6719 Remote Similarity NPD8328 Phase 3
0.6718 Remote Similarity NPD7319 Approved
0.6698 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6697 Remote Similarity NPD3573 Approved
0.6696 Remote Similarity NPD5779 Approved
0.6696 Remote Similarity NPD5778 Approved
0.6694 Remote Similarity NPD6868 Approved
0.6694 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6694 Remote Similarity NPD5135 Approved
0.6694 Remote Similarity NPD5169 Approved
0.6667 Remote Similarity NPD46 Approved
0.6667 Remote Similarity NPD1694 Approved
0.6667 Remote Similarity NPD6698 Approved
0.6667 Remote Similarity NPD5692 Phase 3
0.6667 Remote Similarity NPD5785 Approved
0.6639 Remote Similarity NPD5127 Approved
0.6637 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7900 Approved
0.6607 Remote Similarity NPD6050 Approved
0.6607 Remote Similarity NPD5694 Approved
0.6606 Remote Similarity NPD5690 Phase 2
0.6587 Remote Similarity NPD7327 Approved
0.6587 Remote Similarity NPD7328 Approved
0.6583 Remote Similarity NPD6412 Phase 2
0.6574 Remote Similarity NPD4197 Approved
0.6535 Remote Similarity NPD7516 Approved
0.6515 Remote Similarity NPD6033 Approved
0.6514 Remote Similarity NPD5363 Approved
0.6514 Remote Similarity NPD5329 Approved
0.6509 Remote Similarity NPD4695 Discontinued
0.6481 Remote Similarity NPD7154 Phase 3
0.6481 Remote Similarity NPD5362 Discontinued
0.648 Remote Similarity NPD5167 Approved
0.6466 Remote Similarity NPD5959 Approved
0.646 Remote Similarity NPD8034 Phase 2
0.646 Remote Similarity NPD8035 Phase 2
0.646 Remote Similarity NPD7637 Suspended
0.6455 Remote Similarity NPD6409 Approved
0.6455 Remote Similarity NPD4519 Discontinued
0.6455 Remote Similarity NPD6684 Approved
0.6455 Remote Similarity NPD7334 Approved
0.6455 Remote Similarity NPD5330 Approved
0.6455 Remote Similarity NPD5280 Approved
0.6455 Remote Similarity NPD4694 Approved
0.6455 Remote Similarity NPD4623 Approved
0.6455 Remote Similarity NPD6098 Approved
0.6455 Remote Similarity NPD7146 Approved
0.6455 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6455 Remote Similarity NPD7521 Approved
0.6455 Remote Similarity NPD5279 Phase 3
0.6434 Remote Similarity NPD8033 Approved
0.6422 Remote Similarity NPD4786 Approved
0.6422 Remote Similarity NPD3666 Approved
0.6422 Remote Similarity NPD3665 Phase 1
0.6422 Remote Similarity NPD3133 Approved
0.6393 Remote Similarity NPD5168 Approved
0.6389 Remote Similarity NPD4223 Phase 3
0.6389 Remote Similarity NPD4221 Approved
0.6389 Remote Similarity NPD3667 Approved
0.6378 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6372 Remote Similarity NPD5207 Approved
0.637 Remote Similarity NPD7260 Phase 2
0.6357 Remote Similarity NPD8377 Approved
0.6357 Remote Similarity NPD8294 Approved
0.6341 Remote Similarity NPD8132 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