Structure

Physi-Chem Properties

Molecular Weight:  450.12
Volume:  415.784
LogP:  0.894
LogD:  0.371
LogS:  -4.034
# Rotatable Bonds:  3
TPSA:  186.37
# H-Bond Aceptor:  11
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.313
Synthetic Accessibility Score:  4.35
Fsp3:  0.381
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.609
MDCK Permeability:  6.924437457200838e-06
Pgp-inhibitor:  0.021
Pgp-substrate:  0.873
Human Intestinal Absorption (HIA):  0.431
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  92.50383758544922%
Volume Distribution (VD):  0.585
Pgp-substrate:  10.76651668548584%

ADMET: Metabolism

CYP1A2-inhibitor:  0.088
CYP1A2-substrate:  0.067
CYP2C19-inhibitor:  0.046
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.213
CYP2C9-substrate:  0.586
CYP2D6-inhibitor:  0.261
CYP2D6-substrate:  0.199
CYP3A4-inhibitor:  0.53
CYP3A4-substrate:  0.081

ADMET: Excretion

Clearance (CL):  6.06
Half-life (T1/2):  0.547

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.162
Drug-inuced Liver Injury (DILI):  0.967
AMES Toxicity:  0.736
Rat Oral Acute Toxicity:  0.085
Maximum Recommended Daily Dose:  0.02
Skin Sensitization:  0.947
Carcinogencity:  0.162
Eye Corrosion:  0.003
Eye Irritation:  0.881
Respiratory Toxicity:  0.059

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC52382

Natural Product ID:  NPC52382
Common Name*:   (2S,3S)-2-(3,4-Dihydroxyphenyl)-5,7-Dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-Trihydroxy-6-Methyloxan-2-Yl]Oxy-2,3-Dihydrochromen-4-One
IUPAC Name:   (2S,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
Synonyms:  
Standard InCHIKey:  ZROGCCBNZBKLEL-MFSALPCASA-N
Standard InCHI:  InChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19-,20+,21-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1C(=O)c2c(cc(cc2O[C@H]1c1ccc(c(c1)O)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1314522
PubChem CID:   442437
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003531] Flavonoid-3-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
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. PMID[10993146]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. Tsukuba, Japan 1998-JUN PMID[12381108]
NPO19593 Placida dendritica Species Limapontiidae Eukaryota n.a. Mediterranean n.a. PMID[14575447]
NPO19593 Placida dendritica Species Limapontiidae Eukaryota n.a. n.a. n.a. PMID[14575447]
NPO25611 Smilax china Species Smilacaceae Eukaryota stems n.a. n.a. PMID[16252910]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota Whole plant n.a. n.a. PMID[16643038]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[20038159]
NPO18410 Cyclea racemosa Species Menispermaceae Eukaryota roots n.a. n.a. PMID[20593839]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. leaf n.a. PMID[24197199]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. PMID[24254087]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota aerial part n.a. n.a. PMID[25442304]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. PMID[31861466]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18410 Cyclea racemosa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO16399 Erythrina folkersii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17965 Helenium arizonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18410 Cyclea racemosa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18410 Cyclea racemosa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19652 Pittosporum phillyraeoides Species Pittosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19593 Placida dendritica Species Limapontiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17965 Helenium arizonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18904 Piper guayranum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5929 Neoscopelus microchir Species Neoscopelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18495 Corynocarpus laevigatus Species Corynocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18410 Cyclea racemosa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15713 Zalerion maritima Species Lulworthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16399 Erythrina folkersii Species Fabaceae 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
NPT1356 Individual Protein Protein disulfide-isomerase Homo sapiens AC50 = 10220.0 nM PMID[449857]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 22387.2 nM PMID[449857]
NPT477 Individual Protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 11220.2 nM PMID[449857]
NPT1356 Individual Protein Protein disulfide-isomerase Homo sapiens AC50 n.a. 10220.0 nM PMID[449857]
NPT1417 Individual Protein Transcriptional regulator ERG Homo sapiens Potency n.a. 39810.7 nM PMID[449857]
NPT2 Others Unspecified Potency = 2592.9 nM PMID[449857]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 11689.1 nM PMID[449857]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[449857]
NPT2 Others Unspecified Potency n.a. 501.2 nM PMID[449857]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 79432.8 nM PMID[449857]

☑ 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 NPC52382 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 NPC270578
0.9937 High Similarity NPC160156
0.9937 High Similarity NPC92565
0.9812 High Similarity NPC95866
0.9811 High Similarity NPC127546
0.9811 High Similarity NPC52550
0.9811 High Similarity NPC223424
0.9811 High Similarity NPC317489
0.9811 High Similarity NPC84362
0.9811 High Similarity NPC173637
0.9753 High Similarity NPC294629
0.9752 High Similarity NPC134532
0.9752 High Similarity NPC203259
0.9752 High Similarity NPC471748
0.9752 High Similarity NPC471725
0.9752 High Similarity NPC176740
0.9752 High Similarity NPC155877
0.9752 High Similarity NPC33054
0.975 High Similarity NPC223747
0.975 High Similarity NPC225434
0.975 High Similarity NPC219904
0.975 High Similarity NPC120099
0.975 High Similarity NPC203050
0.9748 High Similarity NPC5778
0.9748 High Similarity NPC118284
0.9748 High Similarity NPC281131
0.9748 High Similarity NPC88789
0.9748 High Similarity NPC145038
0.9748 High Similarity NPC236934
0.9748 High Similarity NPC274618
0.9748 High Similarity NPC276222
0.9748 High Similarity NPC253662
0.9748 High Similarity NPC135599
0.9748 High Similarity NPC179950
0.9748 High Similarity NPC56077
0.9748 High Similarity NPC113968
0.9748 High Similarity NPC308404
0.9748 High Similarity NPC277174
0.9748 High Similarity NPC73855
0.9748 High Similarity NPC328940
0.9747 High Similarity NPC29830
0.9689 High Similarity NPC244776
0.9689 High Similarity NPC116864
0.9689 High Similarity NPC67105
0.9689 High Similarity NPC259896
0.9689 High Similarity NPC156869
0.9689 High Similarity NPC255157
0.9689 High Similarity NPC254855
0.9689 High Similarity NPC136042
0.9689 High Similarity NPC206123
0.9689 High Similarity NPC29958
0.9689 High Similarity NPC67326
0.9688 High Similarity NPC265530
0.9688 High Similarity NPC226304
0.9688 High Similarity NPC325555
0.9686 High Similarity NPC240431
0.9686 High Similarity NPC55786
0.9686 High Similarity NPC277205
0.9686 High Similarity NPC19388
0.9684 High Similarity NPC127782
0.9684 High Similarity NPC300537
0.9632 High Similarity NPC294815
0.9632 High Similarity NPC16194
0.9632 High Similarity NPC476472
0.9632 High Similarity NPC19108
0.9632 High Similarity NPC473327
0.9632 High Similarity NPC220173
0.963 High Similarity NPC153755
0.963 High Similarity NPC245452
0.963 High Similarity NPC60735
0.963 High Similarity NPC26230
0.963 High Similarity NPC175107
0.963 High Similarity NPC190003
0.9627 High Similarity NPC229687
0.9627 High Similarity NPC227508
0.9627 High Similarity NPC43587
0.9625 High Similarity NPC210073
0.9625 High Similarity NPC197285
0.9625 High Similarity NPC115674
0.9625 High Similarity NPC21100
0.9623 High Similarity NPC19709
0.9573 High Similarity NPC470949
0.9573 High Similarity NPC292019
0.9573 High Similarity NPC268533
0.9573 High Similarity NPC202908
0.9573 High Similarity NPC122467
0.9573 High Similarity NPC89127
0.9573 High Similarity NPC472382
0.9573 High Similarity NPC65563
0.9573 High Similarity NPC472380
0.9573 High Similarity NPC471669
0.9573 High Similarity NPC472384
0.9573 High Similarity NPC14187
0.9571 High Similarity NPC42773
0.9571 High Similarity NPC101026
0.9571 High Similarity NPC21666
0.9571 High Similarity NPC45522
0.9571 High Similarity NPC24043
0.9571 High Similarity NPC4390
0.9571 High Similarity NPC169977
0.9568 High Similarity NPC235260
0.9568 High Similarity NPC20505
0.9568 High Similarity NPC155763
0.9568 High Similarity NPC177731
0.9568 High Similarity NPC285197
0.9568 High Similarity NPC21190
0.9568 High Similarity NPC231194
0.9568 High Similarity NPC79056
0.9568 High Similarity NPC150767
0.9568 High Similarity NPC183357
0.9568 High Similarity NPC78734
0.9568 High Similarity NPC51326
0.9568 High Similarity NPC105095
0.9568 High Similarity NPC22195
0.9568 High Similarity NPC44328
0.9565 High Similarity NPC477502
0.9565 High Similarity NPC149244
0.9565 High Similarity NPC229729
0.9565 High Similarity NPC48640
0.9565 High Similarity NPC275454
0.9565 High Similarity NPC45400
0.9563 High Similarity NPC311830
0.9563 High Similarity NPC22832
0.956 High Similarity NPC77660
0.956 High Similarity NPC189142
0.956 High Similarity NPC473043
0.9557 High Similarity NPC153342
0.9515 High Similarity NPC251417
0.9515 High Similarity NPC168584
0.9515 High Similarity NPC89052
0.9515 High Similarity NPC173837
0.9512 High Similarity NPC253685
0.9512 High Similarity NPC108202
0.9509 High Similarity NPC117260
0.9509 High Similarity NPC256760
0.9509 High Similarity NPC476405
0.9509 High Similarity NPC261254
0.9509 High Similarity NPC301683
0.9506 High Similarity NPC293629
0.9506 High Similarity NPC95855
0.9506 High Similarity NPC170675
0.9506 High Similarity NPC209296
0.9506 High Similarity NPC210042
0.9506 High Similarity NPC472381
0.9506 High Similarity NPC138927
0.9506 High Similarity NPC105283
0.9506 High Similarity NPC471457
0.9506 High Similarity NPC472383
0.9506 High Similarity NPC195257
0.9506 High Similarity NPC112755
0.9503 High Similarity NPC255615
0.9503 High Similarity NPC67037
0.9503 High Similarity NPC8856
0.95 High Similarity NPC191306
0.95 High Similarity NPC270335
0.95 High Similarity NPC222936
0.95 High Similarity NPC284960
0.95 High Similarity NPC168822
0.95 High Similarity NPC309025
0.95 High Similarity NPC243930
0.95 High Similarity NPC88023
0.9458 High Similarity NPC470443
0.9458 High Similarity NPC470444
0.9458 High Similarity NPC110941
0.9458 High Similarity NPC241423
0.9458 High Similarity NPC473571
0.9458 High Similarity NPC192539
0.9458 High Similarity NPC473682
0.9458 High Similarity NPC126784
0.9455 High Similarity NPC473862
0.9455 High Similarity NPC48984
0.9455 High Similarity NPC8573
0.9455 High Similarity NPC219043
0.9455 High Similarity NPC169733
0.9455 High Similarity NPC472385
0.9455 High Similarity NPC198324
0.9451 High Similarity NPC51774
0.9451 High Similarity NPC239549
0.9451 High Similarity NPC236191
0.9451 High Similarity NPC208668
0.9448 High Similarity NPC245014
0.9448 High Similarity NPC282987
0.9448 High Similarity NPC471416
0.9448 High Similarity NPC44558
0.9448 High Similarity NPC72249
0.9448 High Similarity NPC474434
0.9448 High Similarity NPC218488
0.9448 High Similarity NPC34287
0.9448 High Similarity NPC84265
0.9444 High Similarity NPC93099
0.9441 High Similarity NPC165720
0.9441 High Similarity NPC34531
0.9437 High Similarity NPC259834
0.9405 High Similarity NPC148710
0.9401 High Similarity NPC473071
0.9401 High Similarity NPC473073
0.9398 High Similarity NPC35167
0.9398 High Similarity NPC217520
0.9398 High Similarity NPC139571
0.9394 High Similarity NPC264735

  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 NPC52382 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
0.9752 High Similarity NPD6797 Phase 2
0.9691 High Similarity NPD7251 Discontinued
0.9568 High Similarity NPD7074 Phase 3
0.9512 High Similarity NPD7808 Phase 3
0.9506 High Similarity NPD7054 Approved
0.9448 High Similarity NPD7472 Approved
0.9394 High Similarity NPD4338 Clinical (unspecified phase)
0.9321 High Similarity NPD6167 Clinical (unspecified phase)
0.9321 High Similarity NPD6168 Clinical (unspecified phase)
0.9321 High Similarity NPD6166 Phase 2
0.9268 High Similarity NPD7804 Clinical (unspecified phase)
0.9207 High Similarity NPD3818 Discontinued
0.9187 High Similarity NPD4381 Clinical (unspecified phase)
0.9057 High Similarity NPD1934 Approved
0.9 High Similarity NPD2393 Clinical (unspecified phase)
0.8827 High Similarity NPD3817 Phase 2
0.8773 High Similarity NPD3882 Suspended
0.872 High Similarity NPD7075 Discontinued
0.8679 High Similarity NPD1512 Approved
0.8659 High Similarity NPD4868 Clinical (unspecified phase)
0.865 High Similarity NPD2801 Approved
0.8596 High Similarity NPD7993 Clinical (unspecified phase)
0.858 High Similarity NPD4380 Phase 2
0.8553 High Similarity NPD1511 Approved
0.8547 High Similarity NPD6559 Discontinued
0.8537 High Similarity NPD7096 Clinical (unspecified phase)
0.8476 Intermediate Similarity NPD6801 Discontinued
0.8385 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD5402 Approved
0.8323 Intermediate Similarity NPD6799 Approved
0.8291 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8291 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD5494 Approved
0.8282 Intermediate Similarity NPD5403 Approved
0.8239 Intermediate Similarity NPD1549 Phase 2
0.8222 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD5401 Approved
0.8155 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD6599 Discontinued
0.8129 Intermediate Similarity NPD6959 Discontinued
0.8103 Intermediate Similarity NPD3751 Discontinued
0.8095 Intermediate Similarity NPD7819 Suspended
0.8095 Intermediate Similarity NPD1465 Phase 2
0.8084 Intermediate Similarity NPD7411 Suspended
0.8081 Intermediate Similarity NPD3787 Discontinued
0.8057 Intermediate Similarity NPD5844 Phase 1
0.8035 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD1653 Approved
0.8 Intermediate Similarity NPD2796 Approved
0.8 Intermediate Similarity NPD7228 Approved
0.7977 Intermediate Similarity NPD6232 Discontinued
0.7952 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD7473 Discontinued
0.7939 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD1510 Phase 2
0.7933 Intermediate Similarity NPD8313 Approved
0.7933 Intermediate Similarity NPD8312 Approved
0.7919 Intermediate Similarity NPD7199 Phase 2
0.7911 Intermediate Similarity NPD1613 Approved
0.7911 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7845 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD7266 Discontinued
0.7821 Intermediate Similarity NPD7685 Pre-registration
0.7819 Intermediate Similarity NPD6780 Approved
0.7819 Intermediate Similarity NPD6777 Approved
0.7819 Intermediate Similarity NPD6779 Approved
0.7819 Intermediate Similarity NPD6781 Approved
0.7819 Intermediate Similarity NPD6778 Approved
0.7819 Intermediate Similarity NPD6776 Approved
0.7819 Intermediate Similarity NPD6782 Approved
0.7803 Intermediate Similarity NPD919 Approved
0.7803 Intermediate Similarity NPD6234 Discontinued
0.7799 Intermediate Similarity NPD1240 Approved
0.7789 Intermediate Similarity NPD7435 Discontinued
0.7784 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD6190 Approved
0.7727 Intermediate Similarity NPD3926 Phase 2
0.7719 Intermediate Similarity NPD37 Approved
0.7717 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD1247 Approved
0.7702 Intermediate Similarity NPD1607 Approved
0.7696 Intermediate Similarity NPD7698 Approved
0.7696 Intermediate Similarity NPD7696 Phase 3
0.7696 Intermediate Similarity NPD7697 Approved
0.7688 Intermediate Similarity NPD4965 Approved
0.7688 Intermediate Similarity NPD4966 Approved
0.7688 Intermediate Similarity NPD943 Approved
0.7688 Intermediate Similarity NPD4967 Phase 2
0.768 Intermediate Similarity NPD8151 Discontinued
0.7674 Intermediate Similarity NPD8455 Phase 2
0.7668 Intermediate Similarity NPD7584 Approved
0.7665 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7629 Intermediate Similarity NPD7701 Phase 2
0.761 Intermediate Similarity NPD3027 Phase 3
0.7595 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD3750 Approved
0.759 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD4628 Phase 3
0.7586 Intermediate Similarity NPD7768 Phase 2
0.7576 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD7870 Phase 2
0.7565 Intermediate Similarity NPD7871 Phase 2
0.7553 Intermediate Similarity NPD6535 Approved
0.7553 Intermediate Similarity NPD6534 Approved
0.7551 Intermediate Similarity NPD7874 Approved
0.7551 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD3749 Approved
0.7531 Intermediate Similarity NPD230 Phase 1
0.7531 Intermediate Similarity NPD1933 Approved
0.7527 Intermediate Similarity NPD7240 Approved
0.7526 Intermediate Similarity NPD7699 Phase 2
0.7526 Intermediate Similarity NPD7700 Phase 2
0.7513 Intermediate Similarity NPD7783 Phase 2
0.7513 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD8320 Phase 1
0.7474 Intermediate Similarity NPD8319 Approved
0.7455 Intermediate Similarity NPD2935 Discontinued
0.7455 Intermediate Similarity NPD1551 Phase 2
0.7453 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD7801 Approved
0.7412 Intermediate Similarity NPD2532 Approved
0.7412 Intermediate Similarity NPD2534 Approved
0.7412 Intermediate Similarity NPD2533 Approved
0.7394 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD6823 Phase 2
0.7346 Intermediate Similarity NPD6798 Discontinued
0.7326 Intermediate Similarity NPD8150 Discontinued
0.7326 Intermediate Similarity NPD8434 Phase 2
0.7321 Intermediate Similarity NPD2800 Approved
0.7317 Intermediate Similarity NPD447 Suspended
0.731 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD3748 Approved
0.7283 Intermediate Similarity NPD5953 Discontinued
0.7273 Intermediate Similarity NPD7585 Approved
0.7268 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6099 Approved
0.7246 Intermediate Similarity NPD6100 Approved
0.7241 Intermediate Similarity NPD7458 Discontinued
0.7241 Intermediate Similarity NPD3226 Approved
0.7225 Intermediate Similarity NPD920 Approved
0.7222 Intermediate Similarity NPD7583 Approved
0.7222 Intermediate Similarity NPD4908 Phase 1
0.7219 Intermediate Similarity NPD6674 Discontinued
0.7216 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD1091 Approved
0.7212 Intermediate Similarity NPD6355 Discontinued
0.7204 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD6233 Phase 2
0.7188 Intermediate Similarity NPD4363 Phase 3
0.7188 Intermediate Similarity NPD4360 Phase 2
0.7186 Intermediate Similarity NPD7033 Discontinued
0.7184 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD7286 Phase 2
0.7169 Intermediate Similarity NPD6651 Approved
0.7157 Intermediate Similarity NPD7680 Approved
0.7151 Intermediate Similarity NPD7390 Discontinued
0.7135 Intermediate Similarity NPD6213 Phase 3
0.7135 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6212 Phase 3
0.7134 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD1243 Approved
0.7117 Intermediate Similarity NPD6832 Phase 2
0.711 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD2346 Discontinued
0.7101 Intermediate Similarity NPD2344 Approved
0.7099 Intermediate Similarity NPD2798 Approved
0.7093 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2799 Discontinued
0.7076 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD9494 Approved
0.7048 Intermediate Similarity NPD4060 Phase 1
0.7045 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD1203 Approved
0.703 Intermediate Similarity NPD2313 Discontinued
0.7022 Intermediate Similarity NPD6844 Discontinued
0.7019 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD1652 Phase 2
0.7011 Intermediate Similarity NPD2403 Approved
0.7011 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5124 Phase 1
0.7 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1610 Phase 2
0.6995 Remote Similarity NPD5710 Approved
0.6995 Remote Similarity NPD5711 Approved
0.6982 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6976 Remote Similarity NPD7930 Approved
0.6966 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5242 Approved
0.6944 Remote Similarity NPD5353 Approved
0.694 Remote Similarity NPD8127 Discontinued
0.6936 Remote Similarity NPD3887 Approved
0.6936 Remote Similarity NPD2309 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