Structure

Physi-Chem Properties

Molecular Weight:  594.16
Volume:  543.527
LogP:  0.599
LogD:  -0.116
LogS:  -3.516
# Rotatable Bonds:  6
TPSA:  249.2
# H-Bond Aceptor:  15
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.149
Synthetic Accessibility Score:  4.711
Fsp3:  0.444
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.473
MDCK Permeability:  2.8840127924922854e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.902
20% Bioavailability (F20%):  0.031
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.052
Plasma Protein Binding (PPB):  88.22504425048828%
Volume Distribution (VD):  0.651
Pgp-substrate:  11.4075345993042%

ADMET: Metabolism

CYP1A2-inhibitor:  0.162
CYP1A2-substrate:  0.054
CYP2C19-inhibitor:  0.061
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.016
CYP2C9-substrate:  0.117
CYP2D6-inhibitor:  0.049
CYP2D6-substrate:  0.145
CYP3A4-inhibitor:  0.037
CYP3A4-substrate:  0.005

ADMET: Excretion

Clearance (CL):  1.6
Half-life (T1/2):  0.588

ADMET: Toxicity

hERG Blockers:  0.235
Human Hepatotoxicity (H-HT):  0.061
Drug-inuced Liver Injury (DILI):  0.957
AMES Toxicity:  0.799
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.013
Skin Sensitization:  0.948
Carcinogencity:  0.219
Eye Corrosion:  0.003
Eye Irritation:  0.478
Respiratory Toxicity:  0.06

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

  Natural Product: NPC210073

Natural Product ID:  NPC210073
Common Name*:   2-(3,4-Dihydroxyphenyl)-5-Hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-Trihydroxy-6-Methyloxan-2-Yl]Oxymethyl]Oxan-2-Yl]Oxychromen-4-One
IUPAC Name:   2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms:  
Standard InCHIKey:  MGYBYJXAXUBTQF-FOBVWLSUSA-N
Standard InCHI:  InChI=1S/C27H30O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-7,9,18,20-30,32-37H,8H2,1H3/t9-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
SMILES:  O[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)Oc1cc(O)c2c(c1)oc(cc2=O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1714943
PubChem CID:   10461109
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO129 Biebersteinia orphanidis Species Biebersteiniaceae Eukaryota n.a. n.a. n.a. PMID[11198823]
NPO16297 Gentiana arisanensis Species Gentianaceae Eukaryota Whole Plant Yu Shieh, Chiayi Hsieh, Taiwan 1994-APR PMID[9287421]
NPO12948 Solanum dulcamara Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14834 Trachelospermum asiaticum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12948 Solanum dulcamara Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14834 Trachelospermum asiaticum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12948 Solanum dulcamara Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14834 Trachelospermum asiaticum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12948 Solanum dulcamara Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16297 Gentiana arisanensis Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5721 Psorothamnus spinosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15721 Derris reticulata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18861 Pyxine coccifera Species Caliciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO129 Biebersteinia orphanidis Species Biebersteiniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16918 Ballota lanata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18413 Eucalyptus ovata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18273 Merendera sobolifera Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16819 Preussia aemulans Species Sporormiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14834 Trachelospermum asiaticum Species Apocynaceae 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
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens AC50 = 2864.0 nM PMID[540472]
NPT2725 Individual Protein Lysine-specific demethylase 4C Homo sapiens AC50 = 2818.0 nM PMID[540472]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 9200.0 nM PMID[540472]
NPT1852 Individual Protein Rac GTPase-activating protein 1 Homo sapiens IC50 n.a. 42700.0 nM PMID[540472]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 35481.3 nM PMID[540472]
NPT5212 Individual Protein Sentrin-specific protease 1 Homo sapiens IC50 n.a. 14700.0 nM PMID[540472]
NPT5212 Individual Protein Sentrin-specific protease 1 Homo sapiens IC50 n.a. 6840.0 nM PMID[540472]
NPT84 Individual Protein Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus AC50 = 15803.0 nM PMID[540472]
NPT2 Others Unspecified IC50 n.a. 46010.0 nM PMID[540472]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 10000.0 nM PMID[540472]

☑ 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 NPC210073 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 NPC115674
0.9873 High Similarity NPC8856
0.9873 High Similarity NPC209296
0.9873 High Similarity NPC195257
0.9872 High Similarity NPC19709
0.9811 High Similarity NPC67105
0.9811 High Similarity NPC150767
0.9811 High Similarity NPC231194
0.9811 High Similarity NPC95866
0.9811 High Similarity NPC51326
0.9811 High Similarity NPC78734
0.9809 High Similarity NPC22832
0.9809 High Similarity NPC311830
0.9808 High Similarity NPC77660
0.9808 High Similarity NPC189142
0.9808 High Similarity NPC473043
0.975 High Similarity NPC203259
0.975 High Similarity NPC256760
0.975 High Similarity NPC471725
0.975 High Similarity NPC471748
0.975 High Similarity NPC176740
0.975 High Similarity NPC33054
0.975 High Similarity NPC155877
0.975 High Similarity NPC134532
0.9748 High Similarity NPC43587
0.9748 High Similarity NPC227508
0.9748 High Similarity NPC86008
0.9747 High Similarity NPC5778
0.9747 High Similarity NPC236934
0.9745 High Similarity NPC309025
0.9745 High Similarity NPC222936
0.9745 High Similarity NPC270335
0.9745 High Similarity NPC243930
0.9745 High Similarity NPC29830
0.9745 High Similarity NPC168822
0.9745 High Similarity NPC284960
0.9745 High Similarity NPC88023
0.9745 High Similarity NPC191306
0.9689 High Similarity NPC204693
0.9689 High Similarity NPC208668
0.9688 High Similarity NPC105095
0.9688 High Similarity NPC44328
0.9688 High Similarity NPC259896
0.9688 High Similarity NPC156869
0.9688 High Similarity NPC177731
0.9688 High Similarity NPC255157
0.9688 High Similarity NPC218488
0.9688 High Similarity NPC254855
0.9688 High Similarity NPC285197
0.9688 High Similarity NPC136042
0.9688 High Similarity NPC29958
0.9688 High Similarity NPC79056
0.9688 High Similarity NPC67326
0.9686 High Similarity NPC173637
0.9686 High Similarity NPC229729
0.9686 High Similarity NPC127546
0.9686 High Similarity NPC52550
0.9686 High Similarity NPC275454
0.9686 High Similarity NPC84362
0.9686 High Similarity NPC223424
0.9686 High Similarity NPC317489
0.9684 High Similarity NPC277205
0.9684 High Similarity NPC284277
0.9684 High Similarity NPC475366
0.9684 High Similarity NPC475497
0.9682 High Similarity NPC127782
0.9682 High Similarity NPC300537
0.963 High Similarity NPC294815
0.963 High Similarity NPC198199
0.963 High Similarity NPC473327
0.963 High Similarity NPC220173
0.963 High Similarity NPC19108
0.963 High Similarity NPC294629
0.963 High Similarity NPC16194
0.963 High Similarity NPC476472
0.9627 High Similarity NPC26230
0.9627 High Similarity NPC180918
0.9627 High Similarity NPC259152
0.9627 High Similarity NPC60735
0.9627 High Similarity NPC3583
0.9627 High Similarity NPC301683
0.9625 High Similarity NPC52382
0.9625 High Similarity NPC219904
0.9625 High Similarity NPC229687
0.9625 High Similarity NPC223747
0.9625 High Similarity NPC226294
0.9625 High Similarity NPC120099
0.9625 High Similarity NPC201292
0.9625 High Similarity NPC58053
0.9625 High Similarity NPC270578
0.9625 High Similarity NPC475942
0.9625 High Similarity NPC45638
0.9625 High Similarity NPC293629
0.9625 High Similarity NPC105283
0.9625 High Similarity NPC186807
0.9625 High Similarity NPC93337
0.9625 High Similarity NPC225434
0.9625 High Similarity NPC469931
0.9625 High Similarity NPC203050
0.9625 High Similarity NPC105025
0.9623 High Similarity NPC88789
0.9623 High Similarity NPC197285
0.9623 High Similarity NPC145038
0.9623 High Similarity NPC281131
0.9623 High Similarity NPC274618
0.9623 High Similarity NPC253662
0.9623 High Similarity NPC21100
0.9623 High Similarity NPC135599
0.9623 High Similarity NPC328940
0.9623 High Similarity NPC113968
0.9623 High Similarity NPC276222
0.9623 High Similarity NPC118284
0.9623 High Similarity NPC277174
0.9623 High Similarity NPC179950
0.9623 High Similarity NPC308404
0.9623 High Similarity NPC73855
0.9623 High Similarity NPC56077
0.9618 High Similarity NPC182045
0.9571 High Similarity NPC169733
0.9571 High Similarity NPC292019
0.9571 High Similarity NPC122467
0.9571 High Similarity NPC14187
0.9571 High Similarity NPC65563
0.9571 High Similarity NPC89127
0.9571 High Similarity NPC202908
0.9571 High Similarity NPC471669
0.9571 High Similarity NPC470949
0.9568 High Similarity NPC25724
0.9568 High Similarity NPC236191
0.9568 High Similarity NPC239549
0.9568 High Similarity NPC472993
0.9568 High Similarity NPC51774
0.9565 High Similarity NPC244776
0.9565 High Similarity NPC206123
0.9565 High Similarity NPC21190
0.9565 High Similarity NPC183357
0.9565 High Similarity NPC22195
0.9565 High Similarity NPC116864
0.9563 High Similarity NPC160156
0.9563 High Similarity NPC226304
0.9563 High Similarity NPC477502
0.9563 High Similarity NPC92565
0.9563 High Similarity NPC58716
0.9563 High Similarity NPC265530
0.9563 High Similarity NPC45400
0.9563 High Similarity NPC146792
0.9563 High Similarity NPC45618
0.9563 High Similarity NPC325555
0.956 High Similarity NPC55786
0.956 High Similarity NPC240431
0.956 High Similarity NPC19388
0.956 High Similarity NPC15358
0.9554 High Similarity NPC110349
0.9551 High Similarity NPC129827
0.9551 High Similarity NPC65003
0.9551 High Similarity NPC44931
0.9551 High Similarity NPC473512
0.9512 High Similarity NPC120952
0.9512 High Similarity NPC251417
0.9512 High Similarity NPC89052
0.9512 High Similarity NPC173837
0.9509 High Similarity NPC253685
0.9506 High Similarity NPC307518
0.9506 High Similarity NPC245452
0.9506 High Similarity NPC117260
0.9506 High Similarity NPC67134
0.9506 High Similarity NPC47140
0.9506 High Similarity NPC476405
0.9506 High Similarity NPC254540
0.9506 High Similarity NPC153755
0.9506 High Similarity NPC172807
0.9506 High Similarity NPC235575
0.9506 High Similarity NPC205076
0.9506 High Similarity NPC211594
0.9506 High Similarity NPC190003
0.9506 High Similarity NPC48773
0.9506 High Similarity NPC267254
0.9506 High Similarity NPC175107
0.9506 High Similarity NPC261254
0.9503 High Similarity NPC95855
0.9503 High Similarity NPC170675
0.9503 High Similarity NPC472381
0.9503 High Similarity NPC471457
0.9503 High Similarity NPC472383
0.9503 High Similarity NPC210042
0.9503 High Similarity NPC112755
0.95 High Similarity NPC99957
0.95 High Similarity NPC181616
0.9497 High Similarity NPC88043
0.9494 High Similarity NPC303913
0.949 High Similarity NPC473634
0.949 High Similarity NPC22062
0.949 High Similarity NPC138811
0.9487 High Similarity NPC261866
0.9455 High Similarity NPC470443
0.9455 High Similarity NPC470444
0.9455 High Similarity NPC110941
0.9455 High Similarity NPC241423
0.9455 High Similarity NPC473571
0.9455 High Similarity NPC192539

  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 NPC210073 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
0.9873 High Similarity NPD7054 Approved
0.9811 High Similarity NPD7472 Approved
0.975 High Similarity NPD6797 Phase 2
0.9689 High Similarity NPD7251 Discontinued
0.9688 High Similarity NPD7074 Phase 3
0.9509 High Similarity NPD7808 Phase 3
0.9321 High Similarity NPD3818 Discontinued
0.9304 High Similarity NPD4381 Clinical (unspecified phase)
0.9273 High Similarity NPD4338 Clinical (unspecified phase)
0.9198 High Similarity NPD6168 Clinical (unspecified phase)
0.9198 High Similarity NPD6167 Clinical (unspecified phase)
0.9198 High Similarity NPD6166 Phase 2
0.9146 High Similarity NPD7804 Clinical (unspecified phase)
0.9051 High Similarity NPD1934 Approved
0.8994 High Similarity NPD2393 Clinical (unspecified phase)
0.8875 High Similarity NPD2801 Approved
0.8782 High Similarity NPD1511 Approved
0.8704 High Similarity NPD3817 Phase 2
0.8688 High Similarity NPD4380 Phase 2
0.8671 High Similarity NPD1512 Approved
0.865 High Similarity NPD4868 Clinical (unspecified phase)
0.8538 High Similarity NPD6559 Discontinued
0.8537 High Similarity NPD3882 Suspended
0.848 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD7075 Discontinued
0.828 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD5494 Approved
0.8261 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8253 Intermediate Similarity NPD5402 Approved
0.8242 Intermediate Similarity NPD6801 Discontinued
0.8228 Intermediate Similarity NPD1549 Phase 2
0.8225 Intermediate Similarity NPD6959 Discontinued
0.8221 Intermediate Similarity NPD1653 Approved
0.8193 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD5403 Approved
0.8144 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8101 Intermediate Similarity NPD2796 Approved
0.8092 Intermediate Similarity NPD7228 Approved
0.8086 Intermediate Similarity NPD6799 Approved
0.8084 Intermediate Similarity NPD1465 Phase 2
0.8084 Intermediate Similarity NPD7819 Suspended
0.8072 Intermediate Similarity NPD7411 Suspended
0.8046 Intermediate Similarity NPD5844 Phase 1
0.8038 Intermediate Similarity NPD1510 Phase 2
0.8037 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD5401 Approved
0.8023 Intermediate Similarity NPD8312 Approved
0.8023 Intermediate Similarity NPD8313 Approved
0.8011 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD7685 Pre-registration
0.7989 Intermediate Similarity NPD3751 Discontinued
0.7965 Intermediate Similarity NPD6232 Discontinued
0.7965 Intermediate Similarity NPD3787 Discontinued
0.7939 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD7266 Discontinued
0.7931 Intermediate Similarity NPD7473 Discontinued
0.7907 Intermediate Similarity NPD7199 Phase 2
0.7898 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD1613 Approved
0.7874 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7802 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD6599 Discontinued
0.7791 Intermediate Similarity NPD6234 Discontinued
0.7791 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD1240 Approved
0.7778 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD8455 Phase 2
0.776 Intermediate Similarity NPD8151 Discontinued
0.7749 Intermediate Similarity NPD7584 Approved
0.7714 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD6776 Approved
0.7713 Intermediate Similarity NPD6779 Approved
0.7713 Intermediate Similarity NPD6780 Approved
0.7713 Intermediate Similarity NPD6781 Approved
0.7713 Intermediate Similarity NPD6777 Approved
0.7713 Intermediate Similarity NPD6782 Approved
0.7713 Intermediate Similarity NPD6778 Approved
0.7706 Intermediate Similarity NPD37 Approved
0.7688 Intermediate Similarity NPD1607 Approved
0.7683 Intermediate Similarity NPD3750 Approved
0.7674 Intermediate Similarity NPD4967 Phase 2
0.7674 Intermediate Similarity NPD4966 Approved
0.7674 Intermediate Similarity NPD4965 Approved
0.7673 Intermediate Similarity NPD943 Approved
0.7651 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7637 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD230 Phase 1
0.7625 Intermediate Similarity NPD1933 Approved
0.7611 Intermediate Similarity NPD7240 Approved
0.7595 Intermediate Similarity NPD3027 Phase 3
0.7592 Intermediate Similarity NPD7435 Discontinued
0.7592 Intermediate Similarity NPD7696 Phase 3
0.7592 Intermediate Similarity NPD7698 Approved
0.7592 Intermediate Similarity NPD7697 Approved
0.759 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7783 Phase 2
0.7586 Intermediate Similarity NPD919 Approved
0.758 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD4628 Phase 3
0.7572 Intermediate Similarity NPD7768 Phase 2
0.7547 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD1551 Phase 2
0.753 Intermediate Similarity NPD6190 Approved
0.7529 Intermediate Similarity NPD3749 Approved
0.7526 Intermediate Similarity NPD7701 Phase 2
0.7514 Intermediate Similarity NPD3926 Phase 2
0.75 Intermediate Similarity NPD1247 Approved
0.7461 Intermediate Similarity NPD7870 Phase 2
0.7461 Intermediate Similarity NPD7871 Phase 2
0.7448 Intermediate Similarity NPD6823 Phase 2
0.7447 Intermediate Similarity NPD6534 Approved
0.7447 Intermediate Similarity NPD6535 Approved
0.7439 Intermediate Similarity NPD2935 Discontinued
0.7421 Intermediate Similarity NPD7699 Phase 2
0.7421 Intermediate Similarity NPD7700 Phase 2
0.741 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD447 Suspended
0.7396 Intermediate Similarity NPD2533 Approved
0.7396 Intermediate Similarity NPD2532 Approved
0.7396 Intermediate Similarity NPD2534 Approved
0.7378 Intermediate Similarity NPD3748 Approved
0.7368 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD7874 Approved
0.7347 Intermediate Similarity NPD7585 Approved
0.7326 Intermediate Similarity NPD7458 Discontinued
0.7323 Intermediate Similarity NPD7801 Approved
0.731 Intermediate Similarity NPD920 Approved
0.7308 Intermediate Similarity NPD1091 Approved
0.7305 Intermediate Similarity NPD2800 Approved
0.7296 Intermediate Similarity NPD7583 Approved
0.7294 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD8320 Phase 1
0.7282 Intermediate Similarity NPD8319 Approved
0.7273 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7033 Discontinued
0.7268 Intermediate Similarity NPD5953 Discontinued
0.7263 Intermediate Similarity NPD4360 Phase 2
0.7263 Intermediate Similarity NPD4363 Phase 3
0.7254 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD7390 Discontinued
0.7231 Intermediate Similarity NPD7680 Approved
0.7229 Intermediate Similarity NPD6099 Approved
0.7229 Intermediate Similarity NPD6100 Approved
0.7225 Intermediate Similarity NPD3226 Approved
0.7219 Intermediate Similarity NPD8150 Discontinued
0.7211 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD6212 Phase 3
0.7211 Intermediate Similarity NPD6213 Phase 3
0.7205 Intermediate Similarity NPD6832 Phase 2
0.7205 Intermediate Similarity NPD4908 Phase 1
0.7202 Intermediate Similarity NPD6674 Discontinued
0.7202 Intermediate Similarity NPD1243 Approved
0.7202 Intermediate Similarity NPD1652 Phase 2
0.72 Intermediate Similarity NPD6844 Discontinued
0.7193 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD2798 Approved
0.7176 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7286 Phase 2
0.7152 Intermediate Similarity NPD6651 Approved
0.7143 Intermediate Similarity NPD9494 Approved
0.7128 Intermediate Similarity NPD8434 Phase 2
0.7125 Intermediate Similarity NPD1203 Approved
0.7117 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD2313 Discontinued
0.7107 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD5124 Phase 1
0.7091 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2346 Discontinued
0.7083 Intermediate Similarity NPD2344 Approved
0.7066 Intermediate Similarity NPD2799 Discontinued
0.7059 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD1548 Phase 1
0.7029 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD5353 Approved
0.7019 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD3268 Approved
0.7012 Intermediate Similarity NPD6798 Discontinued
0.7005 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6981 Remote Similarity NPD422 Phase 1
0.6981 Remote Similarity NPD1610 Phase 2
0.6978 Remote Similarity NPD5710 Approved
0.6978 Remote Similarity NPD5711 Approved
0.697 Remote Similarity NPD6233 Phase 2
0.6964 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7930 Approved
0.6957 Remote Similarity NPD3225 Approved
0.6949 Remote Similarity NPD7615 Clinical (unspecified phase)
0.694 Remote Similarity NPD5242 Approved
0.6937 Remote Similarity NPD9717 Approved
0.6937 Remote Similarity NPD9269 Phase 2
0.6923 Remote Similarity NPD8127 Discontinued

  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