Structure

Physi-Chem Properties

Molecular Weight:  390.28
Volume:  437.082
LogP:  7.337
LogD:  5.716
LogS:  -5.291
# Rotatable Bonds:  16
TPSA:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.343
Synthetic Accessibility Score:  3.007
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.694
MDCK Permeability:  1.622779200260993e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.981
30% Bioavailability (F30%):  0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.015
Plasma Protein Binding (PPB):  99.61510467529297%
Volume Distribution (VD):  1.427
Pgp-substrate:  1.10756254196167%

ADMET: Metabolism

CYP1A2-inhibitor:  0.208
CYP1A2-substrate:  0.305
CYP2C19-inhibitor:  0.749
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.277
CYP2C9-substrate:  0.161
CYP2D6-inhibitor:  0.788
CYP2D6-substrate:  0.12
CYP3A4-inhibitor:  0.733
CYP3A4-substrate:  0.106

ADMET: Excretion

Clearance (CL):  6.965
Half-life (T1/2):  0.13

ADMET: Toxicity

hERG Blockers:  0.204
Human Hepatotoxicity (H-HT):  0.019
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.002
Maximum Recommended Daily Dose:  0.078
Skin Sensitization:  0.943
Carcinogencity:  0.557
Eye Corrosion:  0.06
Eye Irritation:  0.968
Respiratory Toxicity:  0.105

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC305912

Natural Product ID:  NPC305912
Common Name*:   Bis(2-Ethylhexyl) Phthalate
IUPAC Name:   bis(2-ethylhexyl) benzene-1,2-dicarboxylate
Synonyms:   Di(2-Ethylhexyl)Phthalate
Standard InCHIKey:  BJQHLKABXJIVAM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C24H38O4/c1-5-9-13-19(7-3)17-27-23(25)21-15-11-12-16-22(21)24(26)28-18-20(8-4)14-10-6-2/h11-12,15-16,19-20H,5-10,13-14,17-18H2,1-4H3
SMILES:  CCCCC(COC(=O)c1ccccc1C(=O)OCC(CCCC)CC)CC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1242017
PubChem CID:   8343
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid 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
NPO40499 Dioscorea nipponica Makino subsp. rosthornii (Prain et Burkill) C. T. Ting Strain Dioscoreaceae Eukaryota Rhizomes n.a. n.a. PMID[28606759]
NPO11411 Gossypium herbaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11411 Gossypium herbaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8707.1 Pueraria montana var. lobata Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11518.1 Strophanthus sarmentosus var. senegambiae Varieties Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27472 Daiswa polyphylla Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8707.1 Pueraria montana var. lobata Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27472 Daiswa polyphylla Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27472 Daiswa polyphylla Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8707.1 Pueraria montana var. lobata Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11411 Gossypium herbaceum Species Malvaceae 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
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 7943.3 nM PMID[487802]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 15848.9 nM PMID[487802]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 50118.7 nM PMID[487803]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 31622.8 nM PMID[487803]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 50118.7 nM PMID[487803]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[487803]
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 223.9 nM PMID[487802]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 10000.0 nM PMID[487804]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 68589.6 nM PMID[487804]
NPT158 Individual Protein Nuclear receptor subfamily 1 group I member 2 Rattus norvegicus Potency n.a. 11220.2 nM PMID[487804]
NPT102 Individual Protein Interleukin-8 Homo sapiens Potency n.a. 84126.7 nM PMID[487802]
NPT103 Individual Protein Nuclear receptor ROR-gamma Homo sapiens Potency n.a. 74978.0 nM PMID[487802]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 > 50000.0 nM PMID[487806]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 5448.3 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 54941 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 3890 nM PubChem BioAssay data set
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 22387.2 nM PMID[487802]
NPT2 Others Unspecified Potency = 15.8 nM PMID[487802]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 11689.1 nM PMID[487803]
NPT2 Others Unspecified Potency n.a. 5623.4 nM PMID[487803]
NPT610 Others Molecular identity unknown Potency n.a. 14125.4 nM PMID[487804]
NPT2 Others Unspecified AC50 n.a. 3981.1 nM PMID[487805]
NPT2 Others Unspecified Ac50 n.a. 1.413 uM PMID[487805]
NPT2 Others Unspecified Ac50 n.a. 89.13 uM PMID[487805]
NPT2 Others Unspecified Ac50 n.a. 10.0 uM PMID[487805]
NPT2 Others Unspecified AC50 n.a. 10000.0 nM PMID[487805]
NPT2 Others Unspecified Potency n.a. 5495.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 389 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 8707.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1096.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 13800.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 13685.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27298.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3889.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34665.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24336.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30637.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12197.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4364.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6164.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12193.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2169 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19493.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2187.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 863.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2753.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 7695.9 nM PubChem BioAssay data set

☑ 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 NPC305912 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC1082
0.9903 High Similarity NPC270699
0.9903 High Similarity NPC82899
0.9902 High Similarity NPC196246
0.9902 High Similarity NPC214067
0.9902 High Similarity NPC251854
0.9902 High Similarity NPC93084
0.9804 High Similarity NPC17417
0.9804 High Similarity NPC10251
0.9706 High Similarity NPC56493
0.9608 High Similarity NPC119271
0.9528 High Similarity NPC153053
0.9519 High Similarity NPC174099
0.9412 High Similarity NPC31786
0.934 High Similarity NPC321852
0.9245 High Similarity NPC260818
0.9167 High Similarity NPC307651
0.9057 High Similarity NPC85493
0.902 High Similarity NPC146351
0.8942 High Similarity NPC474365
0.8942 High Similarity NPC89886
0.8942 High Similarity NPC301943
0.8922 High Similarity NPC78701
0.8922 High Similarity NPC35448
0.8922 High Similarity NPC225060
0.8909 High Similarity NPC210092
0.8879 High Similarity NPC469636
0.8879 High Similarity NPC265407
0.8879 High Similarity NPC83628
0.8846 High Similarity NPC45613
0.8824 High Similarity NPC276775
0.8824 High Similarity NPC92754
0.8824 High Similarity NPC249912
0.8716 High Similarity NPC474157
0.8692 High Similarity NPC37622
0.8692 High Similarity NPC30594
0.8654 High Similarity NPC325497
0.8627 High Similarity NPC130398
0.8598 High Similarity NPC269457
0.8598 High Similarity NPC209632
0.8585 High Similarity NPC60679
0.8571 High Similarity NPC42211
0.8571 High Similarity NPC70624
0.8559 High Similarity NPC128368
0.8545 High Similarity NPC210089
0.8505 High Similarity NPC114594
0.8496 Intermediate Similarity NPC149691
0.8476 Intermediate Similarity NPC203925
0.8476 Intermediate Similarity NPC118343
0.8448 Intermediate Similarity NPC473243
0.8396 Intermediate Similarity NPC282895
0.8393 Intermediate Similarity NPC272524
0.8378 Intermediate Similarity NPC167504
0.8376 Intermediate Similarity NPC50872
0.8364 Intermediate Similarity NPC474364
0.8364 Intermediate Similarity NPC269023
0.8364 Intermediate Similarity NPC99846
0.8319 Intermediate Similarity NPC308744
0.8319 Intermediate Similarity NPC237366
0.8318 Intermediate Similarity NPC188895
0.8304 Intermediate Similarity NPC79496
0.8264 Intermediate Similarity NPC169913
0.825 Intermediate Similarity NPC246166
0.8246 Intermediate Similarity NPC474685
0.823 Intermediate Similarity NPC161611
0.8214 Intermediate Similarity NPC476003
0.8208 Intermediate Similarity NPC229242
0.8182 Intermediate Similarity NPC275576
0.8182 Intermediate Similarity NPC476599
0.8158 Intermediate Similarity NPC474363
0.8137 Intermediate Similarity NPC220893
0.8137 Intermediate Similarity NPC173443
0.8099 Intermediate Similarity NPC295664
0.8087 Intermediate Similarity NPC474095
0.8087 Intermediate Similarity NPC306740
0.8051 Intermediate Similarity NPC204784
0.8049 Intermediate Similarity NPC51448
0.8049 Intermediate Similarity NPC115797
0.8033 Intermediate Similarity NPC121272
0.8017 Intermediate Similarity NPC100353
0.8 Intermediate Similarity NPC477411
0.8 Intermediate Similarity NPC196075
0.7982 Intermediate Similarity NPC284477
0.7967 Intermediate Similarity NPC51292
0.7946 Intermediate Similarity NPC470391
0.7944 Intermediate Similarity NPC270654
0.7941 Intermediate Similarity NPC89377
0.7937 Intermediate Similarity NPC472394
0.7931 Intermediate Similarity NPC228936
0.792 Intermediate Similarity NPC42234
0.792 Intermediate Similarity NPC272946
0.792 Intermediate Similarity NPC147561
0.7913 Intermediate Similarity NPC474176
0.7895 Intermediate Similarity NPC243355
0.789 Intermediate Similarity NPC473325
0.7886 Intermediate Similarity NPC470765
0.7881 Intermediate Similarity NPC469574
0.7863 Intermediate Similarity NPC135730
0.7863 Intermediate Similarity NPC226093
0.7857 Intermediate Similarity NPC470278
0.7843 Intermediate Similarity NPC318107
0.783 Intermediate Similarity NPC261181
0.7826 Intermediate Similarity NPC158282
0.7826 Intermediate Similarity NPC212415
0.7826 Intermediate Similarity NPC474314
0.7823 Intermediate Similarity NPC473220
0.7823 Intermediate Similarity NPC470753
0.7818 Intermediate Similarity NPC304873
0.7815 Intermediate Similarity NPC254233
0.7812 Intermediate Similarity NPC329913
0.781 Intermediate Similarity NPC119631
0.7795 Intermediate Similarity NPC238370
0.7795 Intermediate Similarity NPC477360
0.7787 Intermediate Similarity NPC472703
0.7787 Intermediate Similarity NPC223351
0.7778 Intermediate Similarity NPC475508
0.7769 Intermediate Similarity NPC144547
0.7759 Intermediate Similarity NPC13784
0.7752 Intermediate Similarity NPC477893
0.7752 Intermediate Similarity NPC477896
0.775 Intermediate Similarity NPC202015
0.7748 Intermediate Similarity NPC255676
0.7745 Intermediate Similarity NPC58616
0.7745 Intermediate Similarity NPC294134
0.7734 Intermediate Similarity NPC477364
0.7731 Intermediate Similarity NPC228318
0.7731 Intermediate Similarity NPC45794
0.7724 Intermediate Similarity NPC472704
0.7724 Intermediate Similarity NPC471466
0.7724 Intermediate Similarity NPC51079
0.7717 Intermediate Similarity NPC475478
0.7714 Intermediate Similarity NPC240108
0.7714 Intermediate Similarity NPC213156
0.7692 Intermediate Similarity NPC304760
0.7686 Intermediate Similarity NPC77000
0.7686 Intermediate Similarity NPC289432
0.7686 Intermediate Similarity NPC238861
0.7686 Intermediate Similarity NPC988
0.7679 Intermediate Similarity NPC329282
0.7674 Intermediate Similarity NPC472591
0.7674 Intermediate Similarity NPC126516
0.7674 Intermediate Similarity NPC48929
0.7674 Intermediate Similarity NPC477368
0.7674 Intermediate Similarity NPC477359
0.7674 Intermediate Similarity NPC474608
0.7674 Intermediate Similarity NPC203486
0.7672 Intermediate Similarity NPC66208
0.7667 Intermediate Similarity NPC293424
0.7656 Intermediate Similarity NPC475569
0.7656 Intermediate Similarity NPC233692
0.7656 Intermediate Similarity NPC239358
0.7656 Intermediate Similarity NPC233860
0.7642 Intermediate Similarity NPC46634
0.7638 Intermediate Similarity NPC473247
0.7638 Intermediate Similarity NPC471832
0.7636 Intermediate Similarity NPC217621
0.7627 Intermediate Similarity NPC81808
0.7627 Intermediate Similarity NPC474408
0.7619 Intermediate Similarity NPC9822
0.7615 Intermediate Similarity NPC473216
0.7615 Intermediate Similarity NPC473399
0.7615 Intermediate Similarity NPC265459
0.7615 Intermediate Similarity NPC291638
0.7615 Intermediate Similarity NPC232888
0.7615 Intermediate Similarity NPC290833
0.7615 Intermediate Similarity NPC17877
0.7615 Intermediate Similarity NPC253423
0.7615 Intermediate Similarity NPC472577
0.7615 Intermediate Similarity NPC475262
0.7615 Intermediate Similarity NPC270364
0.7615 Intermediate Similarity NPC477367
0.7615 Intermediate Similarity NPC195647
0.7615 Intermediate Similarity NPC311339
0.7615 Intermediate Similarity NPC66761
0.76 Intermediate Similarity NPC100402
0.76 Intermediate Similarity NPC9180
0.7597 Intermediate Similarity NPC472656
0.7597 Intermediate Similarity NPC472248
0.7583 Intermediate Similarity NPC152812
0.7581 Intermediate Similarity NPC328107
0.7581 Intermediate Similarity NPC228739
0.7581 Intermediate Similarity NPC318067
0.7578 Intermediate Similarity NPC469519
0.7576 Intermediate Similarity NPC472371
0.7576 Intermediate Similarity NPC472395
0.757 Intermediate Similarity NPC77273
0.7557 Intermediate Similarity NPC472374
0.7557 Intermediate Similarity NPC477358
0.7557 Intermediate Similarity NPC472372
0.7557 Intermediate Similarity NPC194769
0.7557 Intermediate Similarity NPC285221
0.7549 Intermediate Similarity NPC288903
0.7549 Intermediate Similarity NPC270507
0.7547 Intermediate Similarity NPC62765
0.7541 Intermediate Similarity NPC72977
0.7541 Intermediate Similarity NPC232958
0.754 Intermediate Similarity NPC472706
0.754 Intermediate Similarity NPC204579
0.7538 Intermediate Similarity NPC298547
0.7538 Intermediate Similarity NPC28836

  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 NPC305912 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
0.9804 High Similarity NPD2182 Approved
0.9412 High Similarity NPD164 Approved
0.9065 High Similarity NPD2181 Clinical (unspecified phase)
0.8476 Intermediate Similarity NPD1238 Approved
0.7876 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD9257 Approved
0.7843 Intermediate Similarity NPD9259 Approved
0.783 Intermediate Similarity NPD1202 Approved
0.7826 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7807 Intermediate Similarity NPD2067 Discontinued
0.7705 Intermediate Similarity NPD518 Clinical (unspecified phase)
0.7686 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7638 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD6647 Phase 2
0.7561 Intermediate Similarity NPD6287 Discontinued
0.7547 Intermediate Similarity NPD9256 Approved
0.7547 Intermediate Similarity NPD3673 Approved
0.7547 Intermediate Similarity NPD9258 Approved
0.7547 Intermediate Similarity NPD3672 Approved
0.7523 Intermediate Similarity NPD1989 Approved
0.7479 Intermediate Similarity NPD5951 Approved
0.7479 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD1087 Approved
0.7422 Intermediate Similarity NPD6832 Phase 2
0.7377 Intermediate Similarity NPD9545 Approved
0.7368 Intermediate Similarity NPD5909 Discontinued
0.7364 Intermediate Similarity NPD7008 Discontinued
0.7321 Intermediate Similarity NPD2066 Phase 3
0.7281 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7281 Intermediate Similarity NPD1929 Approved
0.7281 Intermediate Similarity NPD1930 Approved
0.7273 Intermediate Similarity NPD9260 Approved
0.7266 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD7631 Approved
0.7244 Intermediate Similarity NPD2199 Approved
0.7244 Intermediate Similarity NPD1876 Approved
0.7244 Intermediate Similarity NPD2198 Approved
0.7241 Intermediate Similarity NPD3134 Approved
0.7222 Intermediate Similarity NPD1090 Approved
0.7222 Intermediate Similarity NPD6637 Approved
0.7222 Intermediate Similarity NPD1089 Approved
0.7222 Intermediate Similarity NPD1086 Approved
0.7213 Intermediate Similarity NPD9493 Approved
0.7182 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD3764 Approved
0.7157 Intermediate Similarity NPD9490 Approved
0.7156 Intermediate Similarity NPD7609 Phase 3
0.7132 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD1019 Discontinued
0.713 Intermediate Similarity NPD800 Approved
0.7122 Intermediate Similarity NPD7236 Approved
0.712 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD1241 Discontinued
0.7091 Intermediate Similarity NPD1088 Approved
0.708 Intermediate Similarity NPD5926 Approved
0.708 Intermediate Similarity NPD9495 Approved
0.7069 Intermediate Similarity NPD1237 Approved
0.7068 Intermediate Similarity NPD2979 Phase 3
0.7063 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD2629 Approved
0.7048 Intermediate Similarity NPD9491 Approved
0.7043 Intermediate Similarity NPD1932 Approved
0.7037 Intermediate Similarity NPD2567 Approved
0.7037 Intermediate Similarity NPD2569 Approved
0.7034 Intermediate Similarity NPD1358 Approved
0.7025 Intermediate Similarity NPD5277 Phase 2
0.7016 Intermediate Similarity NPD2347 Approved
0.7007 Intermediate Similarity NPD2346 Discontinued
0.7007 Intermediate Similarity NPD7702 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6085 Phase 2
0.7 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5740 Clinical (unspecified phase)
0.6985 Remote Similarity NPD2799 Discontinued
0.6983 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6975 Remote Similarity NPD2329 Discontinued
0.6972 Remote Similarity NPD5346 Phase 2
0.6972 Remote Similarity NPD5347 Phase 2
0.697 Remote Similarity NPD6039 Approved
0.6964 Remote Similarity NPD1693 Approved
0.6953 Remote Similarity NPD3972 Approved
0.6953 Remote Similarity NPD9717 Approved
0.6944 Remote Similarity NPD650 Approved
0.694 Remote Similarity NPD3373 Approved
0.6923 Remote Similarity NPD552 Approved
0.6923 Remote Similarity NPD9567 Approved
0.6923 Remote Similarity NPD553 Approved
0.6917 Remote Similarity NPD5235 Approved
0.6917 Remote Similarity NPD1317 Discontinued
0.6917 Remote Similarity NPD2313 Discontinued
0.6917 Remote Similarity NPD5237 Approved
0.6917 Remote Similarity NPD5239 Approved
0.6917 Remote Similarity NPD5240 Approved
0.6917 Remote Similarity NPD5236 Approved
0.6905 Remote Similarity NPD5585 Approved
0.6905 Remote Similarity NPD5691 Approved
0.6893 Remote Similarity NPD225 Approved
0.6893 Remote Similarity NPD227 Approved
0.6889 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6885 Remote Similarity NPD6858 Approved
0.6885 Remote Similarity NPD7094 Approved
0.6875 Remote Similarity NPD7239 Suspended
0.6875 Remote Similarity NPD1563 Approved
0.6875 Remote Similarity NPD4806 Approved
0.6875 Remote Similarity NPD4807 Approved
0.6875 Remote Similarity NPD1281 Approved
0.687 Remote Similarity NPD7798 Approved
0.687 Remote Similarity NPD2798 Approved
0.6866 Remote Similarity NPD7961 Discontinued
0.6866 Remote Similarity NPD7713 Phase 3
0.686 Remote Similarity NPD2201 Approved
0.6855 Remote Similarity NPD4198 Discontinued
0.685 Remote Similarity NPD5306 Approved
0.685 Remote Similarity NPD5305 Approved
0.6846 Remote Similarity NPD5667 Approved
0.6838 Remote Similarity NPD9261 Approved
0.6815 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6814 Remote Similarity NPD688 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6685 Approved
0.6794 Remote Similarity NPD2797 Approved
0.6794 Remote Similarity NPD3266 Approved
0.6794 Remote Similarity NPD3267 Approved
0.6789 Remote Similarity NPD1282 Approved
0.6789 Remote Similarity NPD4793 Discontinued
0.6788 Remote Similarity NPD2670 Approved
0.6777 Remote Similarity NPD4233 Approved
0.6777 Remote Similarity NPD4234 Approved
0.6774 Remote Similarity NPD4766 Approved
0.6769 Remote Similarity NPD182 Clinical (unspecified phase)
0.6765 Remote Similarity NPD230 Phase 1
0.6765 Remote Similarity NPD4618 Approved
0.6765 Remote Similarity NPD4622 Approved
0.6746 Remote Similarity NPD6065 Approved
0.6744 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6739 Remote Similarity NPD3748 Approved
0.6738 Remote Similarity NPD4628 Phase 3
0.6738 Remote Similarity NPD7003 Approved
0.6736 Remote Similarity NPD6273 Approved
0.6729 Remote Similarity NPD3971 Phase 1
0.6719 Remote Similarity NPD17 Approved
0.6718 Remote Similarity NPD1283 Approved
0.6715 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6712 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6698 Remote Similarity NPD226 Approved
0.6696 Remote Similarity NPD1564 Approved
0.6696 Remote Similarity NPD1239 Approved
0.6696 Remote Similarity NPD3495 Discontinued
0.6696 Remote Similarity NPD1566 Phase 3
0.6696 Remote Similarity NPD1565 Approved
0.6694 Remote Similarity NPD2650 Approved
0.6694 Remote Similarity NPD2652 Approved
0.6693 Remote Similarity NPD1894 Discontinued
0.6692 Remote Similarity NPD4878 Approved
0.6691 Remote Similarity NPD4307 Phase 2
0.6691 Remote Similarity NPD2438 Suspended
0.6691 Remote Similarity NPD2935 Discontinued
0.6691 Remote Similarity NPD2531 Phase 2
0.6667 Remote Similarity NPD6362 Approved
0.6667 Remote Similarity NPD3496 Discontinued
0.6667 Remote Similarity NPD5688 Approved
0.6667 Remote Similarity NPD1203 Approved
0.6667 Remote Similarity NPD4136 Approved
0.6667 Remote Similarity NPD5689 Approved
0.6667 Remote Similarity NPD4106 Approved
0.6667 Remote Similarity NPD3268 Approved
0.6667 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4135 Approved
0.6667 Remote Similarity NPD9508 Approved
0.6667 Remote Similarity NPD405 Clinical (unspecified phase)
0.6667 Remote Similarity NPD969 Suspended
0.6643 Remote Similarity NPD7611 Approved
0.6643 Remote Similarity NPD7440 Discontinued
0.6642 Remote Similarity NPD447 Suspended
0.6642 Remote Similarity NPD6355 Discontinued
0.6642 Remote Similarity NPD1933 Approved
0.6641 Remote Similarity NPD4359 Approved
0.6639 Remote Similarity NPD3047 Approved
0.6639 Remote Similarity NPD3646 Clinical (unspecified phase)
0.6639 Remote Similarity NPD3046 Approved
0.6639 Remote Similarity NPD1752 Approved
0.6639 Remote Similarity NPD3048 Approved
0.6639 Remote Similarity NPD1756 Approved
0.6637 Remote Similarity NPD1508 Approved
0.662 Remote Similarity NPD8166 Discontinued
0.662 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6619 Remote Similarity NPD3170 Approved
0.6618 Remote Similarity NPD8032 Phase 2
0.6617 Remote Similarity NPD5647 Approved
0.6613 Remote Similarity NPD2607 Approved
0.6612 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6612 Remote Similarity NPD9267 Approved
0.6612 Remote Similarity NPD9263 Approved
0.6612 Remote Similarity NPD9264 Approved
0.6599 Remote Similarity NPD3226 Approved
0.6599 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6596 Remote Similarity NPD970 Clinical (unspecified phase)
0.6596 Remote Similarity NPD6414 Clinical (unspecified phase)
0.6589 Remote Similarity NPD4626 Approved
0.6589 Remote Similarity NPD1104 Approved
0.6573 Remote Similarity NPD3887 Approved
0.6569 Remote Similarity NPD3140 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data