Structure

Physi-Chem Properties

Molecular Weight:  594.16
Volume:  543.527
LogP:  0.096
LogD:  0.055
LogS:  -2.796
# Rotatable Bonds:  6
TPSA:  253.35
# H-Bond Aceptor:  15
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.149
Synthetic Accessibility Score:  5.228
Fsp3:  0.444
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.519
MDCK Permeability:  1.6216785297729075e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.857
20% Bioavailability (F20%):  0.016
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.043
Plasma Protein Binding (PPB):  91.30667114257812%
Volume Distribution (VD):  0.612
Pgp-substrate:  11.455769538879395%

ADMET: Metabolism

CYP1A2-inhibitor:  0.126
CYP1A2-substrate:  0.034
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.089
CYP2D6-inhibitor:  0.036
CYP2D6-substrate:  0.124
CYP3A4-inhibitor:  0.013
CYP3A4-substrate:  0.004

ADMET: Excretion

Clearance (CL):  1.482
Half-life (T1/2):  0.841

ADMET: Toxicity

hERG Blockers:  0.079
Human Hepatotoxicity (H-HT):  0.208
Drug-inuced Liver Injury (DILI):  0.968
AMES Toxicity:  0.788
Rat Oral Acute Toxicity:  0.085
Maximum Recommended Daily Dose:  0.033
Skin Sensitization:  0.921
Carcinogencity:  0.138
Eye Corrosion:  0.003
Eye Irritation:  0.453
Respiratory Toxicity:  0.043

Download Data

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

  Natural Product: NPC15538

Natural Product ID:  NPC15538
Common Name*:   Keracyanin Chloride
IUPAC Name:   (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol;chloride
Synonyms:   Keracyanin
Standard InCHIKey:  ADZHXBNWNZIHIX-XYGAWYNKSA-N
Standard InCHI:  InChI=1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+;/m0./s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc4c(cc(cc4[o+]c3c3ccc(c(c3)[O-])O)O)O)O2)O)O)O)O1)O)O)O.Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL592218
PubChem CID:   29231
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0001361] Anthocyanins
              • [CHEMONTID:0002996] Anthocyanidin-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
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. fruit n.a. DOI[10.1007/s00217-007-0799-1]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. flower n.a. DOI[10.1016/j.foodchem.2011.01.077]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO21349 Punica granatum Species Lythraceae Eukaryota Seeds n.a. n.a. PMID[15620261]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18341288]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO40677 Vitis vinifera Strain Vitaceae Eukaryota Seeds n.a. n.a. PMID[24157371]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Root Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Stem Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Twig n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Roots n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO21349 Punica granatum Species Lythraceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26422 Rubus chingii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16931 Cichorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26422 Rubus chingii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18930 Rubus coreanus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16931 Cichorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26422 Rubus chingii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18930 Rubus coreanus Species Rosaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 3.25 MU PMID[559616]
NPT2 Others Unspecified Inhibition = 54.0 % PMID[559617]

☑ 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 NPC15538 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 NPC473480
0.9787 High Similarity NPC280945
0.9786 High Similarity NPC125755
0.9784 High Similarity NPC168579
0.9784 High Similarity NPC76176
0.9784 High Similarity NPC469313
0.9784 High Similarity NPC138227
0.972 High Similarity NPC473621
0.9714 High Similarity NPC277867
0.9714 High Similarity NPC161700
0.9712 High Similarity NPC37793
0.9574 High Similarity NPC475096
0.9507 High Similarity NPC99515
0.9507 High Similarity NPC190714
0.95 High Similarity NPC189115
0.95 High Similarity NPC475084
0.9441 High Similarity NPC227902
0.9433 High Similarity NPC473044
0.9429 High Similarity NPC469661
0.9375 High Similarity NPC175976
0.9366 High Similarity NPC25292
0.9366 High Similarity NPC473045
0.9362 High Similarity NPC469559
0.9353 High Similarity NPC262328
0.9353 High Similarity NPC87777
0.9296 High Similarity NPC252169
0.9291 High Similarity NPC210192
0.9286 High Similarity NPC212770
0.9286 High Similarity NPC98777
0.9281 High Similarity NPC203230
0.9281 High Similarity NPC242028
0.9252 High Similarity NPC176186
0.9252 High Similarity NPC169404
0.9252 High Similarity NPC21902
0.9252 High Similarity NPC322899
0.9252 High Similarity NPC226108
0.9252 High Similarity NPC46283
0.9252 High Similarity NPC53587
0.9252 High Similarity NPC44192
0.9252 High Similarity NPC134911
0.9252 High Similarity NPC272552
0.9252 High Similarity NPC469944
0.9231 High Similarity NPC225445
0.922 High Similarity NPC106944
0.9214 High Similarity NPC59324
0.9214 High Similarity NPC65530
0.9214 High Similarity NPC211549
0.9209 High Similarity NPC238243
0.9189 High Similarity NPC78809
0.9189 High Similarity NPC150442
0.9172 High Similarity NPC39657
0.9161 High Similarity NPC81638
0.9161 High Similarity NPC116922
0.9155 High Similarity NPC257095
0.9155 High Similarity NPC89686
0.9155 High Similarity NPC273932
0.9143 High Similarity NPC197723
0.9143 High Similarity NPC16435
0.9143 High Similarity NPC165482
0.9143 High Similarity NPC40664
0.9143 High Similarity NPC306441
0.9143 High Similarity NPC3293
0.9143 High Similarity NPC138350
0.9139 High Similarity NPC185231
0.9137 High Similarity NPC130496
0.9137 High Similarity NPC188555
0.9116 High Similarity NPC472710
0.9116 High Similarity NPC472709
0.9097 High Similarity NPC177597
0.9097 High Similarity NPC171932
0.9097 High Similarity NPC28440
0.9091 High Similarity NPC49542
0.9091 High Similarity NPC472714
0.9091 High Similarity NPC230718
0.9091 High Similarity NPC84207
0.9091 High Similarity NPC5253
0.9091 High Similarity NPC5262
0.9091 High Similarity NPC472353
0.9091 High Similarity NPC128337
0.9091 High Similarity NPC139976
0.9078 High Similarity NPC138738
0.9078 High Similarity NPC470413
0.9078 High Similarity NPC134260
0.9071 High Similarity NPC234333
0.9071 High Similarity NPC112939
0.9071 High Similarity NPC47398
0.9071 High Similarity NPC164787
0.9071 High Similarity NPC61946
0.9071 High Similarity NPC470356
0.9071 High Similarity NPC94750
0.9071 High Similarity NPC474206
0.9071 High Similarity NPC151224
0.9071 High Similarity NPC112246
0.9071 High Similarity NPC260898
0.9071 High Similarity NPC121812
0.9065 High Similarity NPC11060
0.9065 High Similarity NPC294166
0.9065 High Similarity NPC115022
0.906 High Similarity NPC20050
0.906 High Similarity NPC306267
0.9048 High Similarity NPC55158
0.9048 High Similarity NPC286235
0.9048 High Similarity NPC51328
0.9021 High Similarity NPC108674
0.9021 High Similarity NPC178054
0.9014 High Similarity NPC292487
0.9007 High Similarity NPC52277
0.9007 High Similarity NPC269091
0.9007 High Similarity NPC199459
0.9007 High Similarity NPC164857
0.9007 High Similarity NPC227503
0.9007 High Similarity NPC470802
0.9007 High Similarity NPC177035
0.9007 High Similarity NPC302701
0.9007 High Similarity NPC230734
0.9007 High Similarity NPC474639
0.9 High Similarity NPC48863
0.9 High Similarity NPC170694
0.9 High Similarity NPC13745
0.9 High Similarity NPC87696
0.9 High Similarity NPC107478
0.9 High Similarity NPC251981
0.8993 High Similarity NPC61477
0.8993 High Similarity NPC126029
0.8993 High Similarity NPC165686
0.8993 High Similarity NPC476352
0.8993 High Similarity NPC15658
0.8993 High Similarity NPC219876
0.8993 High Similarity NPC78770
0.8993 High Similarity NPC26080
0.8993 High Similarity NPC261619
0.8993 High Similarity NPC185604
0.8993 High Similarity NPC85799
0.8993 High Similarity NPC215060
0.8993 High Similarity NPC303422
0.8986 High Similarity NPC214326
0.8986 High Similarity NPC469706
0.8986 High Similarity NPC9933
0.8986 High Similarity NPC218041
0.8986 High Similarity NPC182368
0.8986 High Similarity NPC238140
0.8986 High Similarity NPC260781
0.8986 High Similarity NPC469707
0.8986 High Similarity NPC145979
0.8986 High Similarity NPC185955
0.8986 High Similarity NPC225815
0.898 High Similarity NPC130449
0.898 High Similarity NPC270751
0.898 High Similarity NPC248132
0.8966 High Similarity NPC118385
0.8966 High Similarity NPC472712
0.8966 High Similarity NPC473046
0.8966 High Similarity NPC187774
0.8966 High Similarity NPC472713
0.8954 High Similarity NPC1253
0.8954 High Similarity NPC100936
0.8947 High Similarity NPC4809
0.8947 High Similarity NPC73517
0.8947 High Similarity NPC147743
0.8944 High Similarity NPC326797
0.8944 High Similarity NPC474282
0.8944 High Similarity NPC102904
0.8944 High Similarity NPC107551
0.8944 High Similarity NPC176051
0.8944 High Similarity NPC103976
0.8936 High Similarity NPC473413
0.8936 High Similarity NPC470236
0.8929 High Similarity NPC69513
0.8929 High Similarity NPC263064
0.8929 High Similarity NPC49074
0.8929 High Similarity NPC132895
0.8929 High Similarity NPC475840
0.8929 High Similarity NPC215833
0.8921 High Similarity NPC475067
0.8921 High Similarity NPC220825
0.8921 High Similarity NPC42760
0.8921 High Similarity NPC121376
0.8921 High Similarity NPC268266
0.8921 High Similarity NPC268342
0.8919 High Similarity NPC106138
0.8919 High Similarity NPC211561
0.8912 High Similarity NPC224674
0.8912 High Similarity NPC170103
0.8912 High Similarity NPC70409
0.8912 High Similarity NPC275284
0.8912 High Similarity NPC236202
0.8912 High Similarity NPC263940
0.8912 High Similarity NPC82917
0.8912 High Similarity NPC108811
0.8912 High Similarity NPC58190
0.8912 High Similarity NPC202742
0.8912 High Similarity NPC193473
0.8912 High Similarity NPC15956
0.8912 High Similarity NPC114505
0.8912 High Similarity NPC18185
0.8912 High Similarity NPC262911
0.8912 High Similarity NPC294558
0.8912 High Similarity NPC213074
0.8912 High Similarity NPC204770
0.8912 High Similarity NPC31325

  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 NPC15538 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
0.8993 High Similarity NPD1612 Clinical (unspecified phase)
0.8993 High Similarity NPD1613 Approved
0.8742 High Similarity NPD7074 Phase 3
0.8705 High Similarity NPD1529 Clinical (unspecified phase)
0.8643 High Similarity NPD3027 Phase 3
0.8633 High Similarity NPD1530 Clinical (unspecified phase)
0.8562 High Similarity NPD7054 Approved
0.8543 High Similarity NPD1653 Approved
0.8509 High Similarity NPD7472 Approved
0.8457 Intermediate Similarity NPD6797 Phase 2
0.8405 Intermediate Similarity NPD7251 Discontinued
0.8367 Intermediate Similarity NPD7266 Discontinued
0.8272 Intermediate Similarity NPD7228 Approved
0.8242 Intermediate Similarity NPD7808 Phase 3
0.8201 Intermediate Similarity NPD1091 Approved
0.8182 Intermediate Similarity NPD4908 Phase 1
0.816 Intermediate Similarity NPD3818 Discontinued
0.8148 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD6166 Phase 2
0.8148 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD6674 Discontinued
0.8113 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8069 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.805 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD1934 Approved
0.795 Intermediate Similarity NPD6234 Discontinued
0.7943 Intermediate Similarity NPD1610 Phase 2
0.7925 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD37 Approved
0.7853 Intermediate Similarity NPD7199 Phase 2
0.7826 Intermediate Similarity NPD4966 Approved
0.7826 Intermediate Similarity NPD4967 Phase 2
0.7826 Intermediate Similarity NPD4965 Approved
0.7812 Intermediate Similarity NPD8455 Phase 2
0.7798 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD1548 Phase 1
0.7751 Intermediate Similarity NPD7240 Approved
0.7751 Intermediate Similarity NPD6559 Discontinued
0.774 Intermediate Similarity NPD2861 Phase 2
0.7651 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD4625 Phase 3
0.7619 Intermediate Similarity NPD3018 Phase 2
0.7593 Intermediate Similarity NPD2801 Approved
0.7586 Intermediate Similarity NPD4749 Approved
0.7584 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD5058 Phase 3
0.7516 Intermediate Similarity NPD4380 Phase 2
0.7485 Intermediate Similarity NPD1465 Phase 2
0.7485 Intermediate Similarity NPD3787 Discontinued
0.7471 Intermediate Similarity NPD5844 Phase 1
0.7468 Intermediate Similarity NPD7213 Phase 3
0.7468 Intermediate Similarity NPD1511 Approved
0.7468 Intermediate Similarity NPD7212 Phase 2
0.7466 Intermediate Similarity NPD2983 Phase 2
0.7466 Intermediate Similarity NPD2982 Phase 2
0.7455 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD3705 Approved
0.7439 Intermediate Similarity NPD3817 Phase 2
0.7436 Intermediate Similarity NPD1652 Phase 2
0.7434 Intermediate Similarity NPD5124 Phase 1
0.7434 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD7447 Phase 1
0.7403 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD2981 Phase 2
0.7394 Intermediate Similarity NPD3882 Suspended
0.7375 Intermediate Similarity NPD1512 Approved
0.7368 Intermediate Similarity NPD4060 Phase 1
0.7361 Intermediate Similarity NPD1357 Approved
0.7351 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD7075 Discontinued
0.7338 Intermediate Similarity NPD4536 Approved
0.7338 Intermediate Similarity NPD4538 Approved
0.7338 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD7097 Phase 1
0.7337 Intermediate Similarity NPD7680 Approved
0.731 Intermediate Similarity NPD3751 Discontinued
0.7286 Intermediate Similarity NPD228 Approved
0.7262 Intermediate Similarity NPD5494 Approved
0.7257 Intermediate Similarity NPD8312 Approved
0.7257 Intermediate Similarity NPD8313 Approved
0.725 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7685 Pre-registration
0.7234 Intermediate Similarity NPD7843 Approved
0.7229 Intermediate Similarity NPD5402 Approved
0.7222 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6959 Discontinued
0.7216 Intermediate Similarity NPD8053 Approved
0.7216 Intermediate Similarity NPD8054 Approved
0.7211 Intermediate Similarity NPD422 Phase 1
0.7203 Intermediate Similarity NPD6671 Approved
0.7203 Intermediate Similarity NPD7157 Approved
0.72 Intermediate Similarity NPD7549 Discontinued
0.7197 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD2684 Approved
0.7191 Intermediate Similarity NPD6842 Approved
0.7191 Intermediate Similarity NPD6841 Approved
0.7191 Intermediate Similarity NPD6843 Phase 3
0.7183 Intermediate Similarity NPD5283 Phase 1
0.7181 Intermediate Similarity NPD8651 Approved
0.7179 Intermediate Similarity NPD5588 Approved
0.7179 Intermediate Similarity NPD5960 Phase 3
0.7175 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD2978 Approved
0.7169 Intermediate Similarity NPD2977 Approved
0.7152 Intermediate Similarity NPD1549 Phase 2
0.7143 Intermediate Similarity NPD3620 Phase 2
0.7143 Intermediate Similarity NPD1558 Phase 1
0.7143 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD6190 Approved
0.7124 Intermediate Similarity NPD6798 Discontinued
0.7122 Intermediate Similarity NPD290 Approved
0.7117 Intermediate Similarity NPD5403 Approved
0.7114 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD6801 Discontinued
0.7107 Intermediate Similarity NPD5177 Phase 3
0.7099 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD4678 Approved
0.7091 Intermediate Similarity NPD4675 Approved
0.7089 Intermediate Similarity NPD3540 Phase 1
0.7086 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD6232 Discontinued
0.7072 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD7819 Suspended
0.7063 Intermediate Similarity NPD3750 Approved
0.7048 Intermediate Similarity NPD7411 Suspended
0.7048 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6100 Approved
0.7025 Intermediate Similarity NPD6099 Approved
0.7025 Intermediate Similarity NPD3539 Phase 1
0.7021 Intermediate Similarity NPD3022 Approved
0.7021 Intermediate Similarity NPD3021 Approved
0.7019 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD2677 Approved
0.7006 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.6994 Remote Similarity NPD5401 Approved
0.6994 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6987 Remote Similarity NPD6355 Discontinued
0.6981 Remote Similarity NPD5763 Approved
0.6981 Remote Similarity NPD5762 Approved
0.6981 Remote Similarity NPD1375 Discontinued
0.6974 Remote Similarity NPD6584 Phase 3
0.6968 Remote Similarity NPD6233 Phase 2
0.6962 Remote Similarity NPD7033 Discontinued
0.6962 Remote Similarity NPD4108 Discontinued
0.6961 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5126 Approved
0.6959 Remote Similarity NPD5846 Approved
0.6959 Remote Similarity NPD5125 Phase 3
0.6959 Remote Similarity NPD6516 Phase 2
0.6957 Remote Similarity NPD4628 Phase 3
0.6957 Remote Similarity NPD3892 Phase 2
0.6957 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7473 Discontinued
0.6951 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6948 Remote Similarity NPD7095 Approved
0.6937 Remote Similarity NPD2424 Discontinued
0.6933 Remote Similarity NPD6799 Approved
0.6928 Remote Similarity NPD4005 Discontinued
0.6927 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6918 Remote Similarity NPD2796 Approved
0.6906 Remote Similarity NPD7906 Approved
0.6897 Remote Similarity NPD2489 Approved
0.6897 Remote Similarity NPD27 Approved
0.6897 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6894 Remote Similarity NPD3060 Approved
0.6891 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6891 Remote Similarity NPD7783 Phase 2
0.689 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6887 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6882 Remote Similarity NPD7768 Phase 2
0.6879 Remote Similarity NPD230 Phase 1
0.6879 Remote Similarity NPD5735 Approved
0.6875 Remote Similarity NPD8151 Discontinued
0.6875 Remote Similarity NPD8156 Discontinued
0.6872 Remote Similarity NPD7310 Approved
0.6872 Remote Similarity NPD7312 Approved
0.6872 Remote Similarity NPD7313 Approved
0.6872 Remote Similarity NPD7311 Approved
0.6855 Remote Similarity NPD1510 Phase 2
0.6852 Remote Similarity NPD7466 Approved
0.6852 Remote Similarity NPD4535 Phase 3
0.6851 Remote Similarity NPD4663 Approved
0.6839 Remote Similarity NPD2970 Approved
0.6839 Remote Similarity NPD2969 Approved
0.6833 Remote Similarity NPD7309 Approved
0.6829 Remote Similarity NPD1774 Approved
0.6826 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6821 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