Structure

Physi-Chem Properties

Molecular Weight:  418.09
Volume:  387.061
LogP:  1.53
LogD:  1.048
LogS:  -3.899
# Rotatable Bonds:  3
TPSA:  170.05
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.35
Synthetic Accessibility Score:  3.804
Fsp3:  0.25
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.076
MDCK Permeability:  6.5183894548681565e-06
Pgp-inhibitor:  0.01
Pgp-substrate:  0.98
Human Intestinal Absorption (HIA):  0.164
20% Bioavailability (F20%):  0.167
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.024
Plasma Protein Binding (PPB):  91.5493392944336%
Volume Distribution (VD):  0.861
Pgp-substrate:  9.181879997253418%

ADMET: Metabolism

CYP1A2-inhibitor:  0.534
CYP1A2-substrate:  0.049
CYP2C19-inhibitor:  0.042
CYP2C19-substrate:  0.05
CYP2C9-inhibitor:  0.211
CYP2C9-substrate:  0.687
CYP2D6-inhibitor:  0.507
CYP2D6-substrate:  0.19
CYP3A4-inhibitor:  0.297
CYP3A4-substrate:  0.025

ADMET: Excretion

Clearance (CL):  5.23
Half-life (T1/2):  0.859

ADMET: Toxicity

hERG Blockers:  0.056
Human Hepatotoxicity (H-HT):  0.082
Drug-inuced Liver Injury (DILI):  0.974
AMES Toxicity:  0.804
Rat Oral Acute Toxicity:  0.125
Maximum Recommended Daily Dose:  0.024
Skin Sensitization:  0.756
Carcinogencity:  0.194
Eye Corrosion:  0.003
Eye Irritation:  0.567
Respiratory Toxicity:  0.033

Download Data

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

  Natural Product: NPC197304

Natural Product ID:  NPC197304
Common Name*:   Kaempferol-O3-Alpha-Arabinopyranoside
IUPAC Name:   5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
Synonyms:  
Standard InCHIKey:  RNVUDWOQYYWXBJ-KRLKJCFRSA-N
Standard InCHI:  InChI=1S/C20H18O10/c21-9-3-1-8(2-4-9)18-19(30-20-17(27)15(25)12(24)7-28-20)16(26)14-11(23)5-10(22)6-13(14)29-18/h1-6,12,15,17,20-25,27H,7H2/t12-,15-,17+,20-/m1/s1
SMILES:  Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@H]1OC[C@H]([C@H]([C@@H]1O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL477730
PubChem CID:   11625890
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
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota Leaves n.a. n.a. PMID[17637068]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. PMID[18302336]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[22432912]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. stem n.a. PMID[26724423]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. root n.a. PMID[26724423]
NPO40537 Koelreuteria henryi Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[8350096]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16807 Cyclamen purpurascens Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11430 Inula grantioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15329 Rhizoplaca baranowii Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16807 Cyclamen purpurascens Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13647 Calcarisporium thermophilum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1759 Alexandrium excavatum Species Gonyaulacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14947 Lathyrus tingitanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1109 Corydalis persica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6906 Atalantia wightii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3761 Plectosphaerella cucumerina Species Plectosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11105 Cacalia floridana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18873.2 Salmonella enterica subsp. enterica serovar bovismorbificans Subspecies Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18126 Pojarkovia stenocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15145 Rauvolfia salicifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3965 Corynanthe pachyceras Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14526 Plectranthus caninus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13848 Amomum daniellii Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5398 Peucedanum oroselinum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16801 Cota tinctoria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7521 Hygrophorus eburneus Species Hygrophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae 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
NPT2 Others Unspecified IC50 = 200.0 ug.mL-1 PMID[480039]
NPT2 Others Unspecified IC50 = 2050000.0 nM PMID[480040]

☑ 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 NPC197304 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 NPC54802
1.0 High Similarity NPC135391
1.0 High Similarity NPC77672
1.0 High Similarity NPC78263
1.0 High Similarity NPC133671
0.9933 High Similarity NPC307938
0.9933 High Similarity NPC111929
0.9933 High Similarity NPC41121
0.9933 High Similarity NPC320283
0.9933 High Similarity NPC472459
0.9933 High Similarity NPC203500
0.9933 High Similarity NPC323593
0.9868 High Similarity NPC471079
0.9868 High Similarity NPC304741
0.9868 High Similarity NPC470405
0.9867 High Similarity NPC182634
0.9867 High Similarity NPC108831
0.9803 High Similarity NPC85707
0.9803 High Similarity NPC181465
0.9803 High Similarity NPC48093
0.9803 High Similarity NPC216496
0.9803 High Similarity NPC473438
0.9803 High Similarity NPC64305
0.9803 High Similarity NPC249281
0.9803 High Similarity NPC265885
0.9803 High Similarity NPC163242
0.9803 High Similarity NPC470125
0.9803 High Similarity NPC282169
0.9803 High Similarity NPC129217
0.9803 High Similarity NPC116458
0.9803 High Similarity NPC173582
0.9803 High Similarity NPC139320
0.9803 High Similarity NPC135846
0.9803 High Similarity NPC297987
0.9803 High Similarity NPC224530
0.9803 High Similarity NPC259957
0.9803 High Similarity NPC476215
0.9803 High Similarity NPC246943
0.9803 High Similarity NPC159579
0.9803 High Similarity NPC170052
0.9803 High Similarity NPC276377
0.9803 High Similarity NPC253788
0.9803 High Similarity NPC215710
0.9799 High Similarity NPC83283
0.9799 High Similarity NPC39360
0.9799 High Similarity NPC29763
0.9799 High Similarity NPC143851
0.9799 High Similarity NPC210003
0.9739 High Similarity NPC240306
0.9739 High Similarity NPC27942
0.9739 High Similarity NPC150164
0.9737 High Similarity NPC153342
0.9737 High Similarity NPC187379
0.9737 High Similarity NPC136761
0.9735 High Similarity NPC288084
0.9733 High Similarity NPC95090
0.9733 High Similarity NPC27408
0.9675 High Similarity NPC66087
0.9675 High Similarity NPC278419
0.9675 High Similarity NPC121703
0.9675 High Similarity NPC179198
0.9671 High Similarity NPC104677
0.9613 High Similarity NPC289667
0.9613 High Similarity NPC72016
0.9613 High Similarity NPC19240
0.9613 High Similarity NPC205824
0.9613 High Similarity NPC85751
0.9613 High Similarity NPC129264
0.9613 High Similarity NPC292929
0.9613 High Similarity NPC76831
0.961 High Similarity NPC131745
0.9605 High Similarity NPC65003
0.9605 High Similarity NPC156457
0.9605 High Similarity NPC44931
0.9605 High Similarity NPC313163
0.9605 High Similarity NPC473512
0.9605 High Similarity NPC129827
0.9605 High Similarity NPC197896
0.9605 High Similarity NPC60966
0.9605 High Similarity NPC161749
0.9605 High Similarity NPC6985
0.9605 High Similarity NPC258035
0.9605 High Similarity NPC122809
0.9603 High Similarity NPC97052
0.9603 High Similarity NPC72649
0.9603 High Similarity NPC169248
0.9603 High Similarity NPC26195
0.9603 High Similarity NPC39351
0.96 High Similarity NPC259767
0.96 High Similarity NPC259182
0.96 High Similarity NPC88484
0.96 High Similarity NPC121001
0.9551 High Similarity NPC12013
0.9551 High Similarity NPC64425
0.9551 High Similarity NPC32641
0.9551 High Similarity NPC256188
0.9551 High Similarity NPC221342
0.9551 High Similarity NPC142142
0.9551 High Similarity NPC11432
0.9551 High Similarity NPC145038
0.9551 High Similarity NPC118284
0.9551 High Similarity NPC281131
0.9551 High Similarity NPC179950
0.9551 High Similarity NPC88789
0.9551 High Similarity NPC276222
0.9551 High Similarity NPC56077
0.9551 High Similarity NPC189564
0.9551 High Similarity NPC274618
0.9551 High Similarity NPC476470
0.9551 High Similarity NPC477613
0.9551 High Similarity NPC253662
0.9551 High Similarity NPC186816
0.9551 High Similarity NPC203145
0.9551 High Similarity NPC308404
0.9548 High Similarity NPC183672
0.9548 High Similarity NPC80068
0.9542 High Similarity NPC22062
0.9542 High Similarity NPC138811
0.9542 High Similarity NPC473634
0.9542 High Similarity NPC73511
0.9539 High Similarity NPC206378
0.9539 High Similarity NPC261866
0.9539 High Similarity NPC170475
0.9536 High Similarity NPC106625
0.949 High Similarity NPC52550
0.949 High Similarity NPC317489
0.949 High Similarity NPC127546
0.949 High Similarity NPC223424
0.949 High Similarity NPC173637
0.949 High Similarity NPC84362
0.9487 High Similarity NPC277205
0.9487 High Similarity NPC55786
0.9487 High Similarity NPC139060
0.9487 High Similarity NPC135358
0.9487 High Similarity NPC240431
0.9487 High Similarity NPC19388
0.9487 High Similarity NPC287889
0.9484 High Similarity NPC259834
0.9481 High Similarity NPC473623
0.9474 High Similarity NPC99233
0.9467 High Similarity NPC191154
0.943 High Similarity NPC5319
0.943 High Similarity NPC203050
0.943 High Similarity NPC223747
0.943 High Similarity NPC219904
0.943 High Similarity NPC120099
0.943 High Similarity NPC225434
0.9427 High Similarity NPC21100
0.9427 High Similarity NPC328940
0.9427 High Similarity NPC197285
0.9427 High Similarity NPC277174
0.9427 High Similarity NPC73855
0.9427 High Similarity NPC113968
0.9427 High Similarity NPC135599
0.9419 High Similarity NPC472994
0.9419 High Similarity NPC270675
0.9419 High Similarity NPC477628
0.9419 High Similarity NPC210961
0.9419 High Similarity NPC47923
0.9419 High Similarity NPC303913
0.9419 High Similarity NPC477629
0.9419 High Similarity NPC101636
0.9419 High Similarity NPC195685
0.9416 High Similarity NPC308265
0.9412 High Similarity NPC295613
0.9412 High Similarity NPC149368
0.9412 High Similarity NPC45165
0.9412 High Similarity NPC473657
0.9412 High Similarity NPC127406
0.9412 High Similarity NPC265480
0.9404 High Similarity NPC134819
0.9371 High Similarity NPC470712
0.9371 High Similarity NPC209550
0.9371 High Similarity NPC155763
0.9371 High Similarity NPC277532
0.9371 High Similarity NPC156869
0.9371 High Similarity NPC116864
0.9371 High Similarity NPC259896
0.9371 High Similarity NPC138990
0.9371 High Similarity NPC235260
0.9371 High Similarity NPC280642
0.9371 High Similarity NPC96605
0.9371 High Similarity NPC29958
0.9371 High Similarity NPC254855
0.9371 High Similarity NPC255157
0.9371 High Similarity NPC175429
0.9371 High Similarity NPC164704
0.9371 High Similarity NPC218161
0.9371 High Similarity NPC136042
0.9371 High Similarity NPC20505
0.9371 High Similarity NPC95866
0.9371 High Similarity NPC67326
0.9371 High Similarity NPC244776
0.9371 High Similarity NPC206123
0.9367 High Similarity NPC92565
0.9367 High Similarity NPC160156
0.9367 High Similarity NPC325555
0.9367 High Similarity NPC265530
0.9367 High Similarity NPC226304
0.9359 High Similarity NPC244875

  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 NPC197304 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
0.9605 High Similarity NPD4381 Clinical (unspecified phase)
0.943 High Similarity NPD7804 Clinical (unspecified phase)
0.9313 High Similarity NPD6797 Phase 2
0.9255 High Similarity NPD7251 Discontinued
0.9198 High Similarity NPD7808 Phase 3
0.9198 High Similarity NPD4338 Clinical (unspecified phase)
0.9068 High Similarity NPD7054 Approved
0.9012 High Similarity NPD7472 Approved
0.8961 High Similarity NPD4380 Phase 2
0.8896 High Similarity NPD7074 Phase 3
0.8889 High Similarity NPD5403 Approved
0.8889 High Similarity NPD3818 Discontinued
0.8861 High Similarity NPD7075 Discontinued
0.8846 High Similarity NPD6801 Discontinued
0.8758 High Similarity NPD5401 Approved
0.8693 High Similarity NPD6799 Approved
0.8671 High Similarity NPD7096 Clinical (unspecified phase)
0.8667 High Similarity NPD1550 Clinical (unspecified phase)
0.8667 High Similarity NPD1552 Clinical (unspecified phase)
0.865 High Similarity NPD6168 Clinical (unspecified phase)
0.865 High Similarity NPD6166 Phase 2
0.865 High Similarity NPD6167 Clinical (unspecified phase)
0.8636 High Similarity NPD4378 Clinical (unspecified phase)
0.8616 High Similarity NPD3817 Phase 2
0.8616 High Similarity NPD5402 Approved
0.8609 High Similarity NPD1549 Phase 2
0.8491 Intermediate Similarity NPD1934 Approved
0.8462 Intermediate Similarity NPD1512 Approved
0.8452 Intermediate Similarity NPD6559 Discontinued
0.8438 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8365 Intermediate Similarity NPD6599 Discontinued
0.8333 Intermediate Similarity NPD3882 Suspended
0.8333 Intermediate Similarity NPD1511 Approved
0.8323 Intermediate Similarity NPD2801 Approved
0.8313 Intermediate Similarity NPD7411 Suspended
0.8289 Intermediate Similarity NPD1510 Phase 2
0.828 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8272 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD2796 Approved
0.8221 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8107 Intermediate Similarity NPD3751 Discontinued
0.8084 Intermediate Similarity NPD3787 Discontinued
0.807 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD1240 Approved
0.7988 Intermediate Similarity NPD7819 Suspended
0.7922 Intermediate Similarity NPD1607 Approved
0.7917 Intermediate Similarity NPD6959 Discontinued
0.7911 Intermediate Similarity NPD3750 Approved
0.7911 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD7584 Approved
0.7845 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD8312 Approved
0.7829 Intermediate Similarity NPD8313 Approved
0.7791 Intermediate Similarity NPD1653 Approved
0.7778 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD8455 Phase 2
0.7771 Intermediate Similarity NPD1551 Phase 2
0.7751 Intermediate Similarity NPD5494 Approved
0.7738 Intermediate Similarity NPD3749 Approved
0.7717 Intermediate Similarity NPD6776 Approved
0.7717 Intermediate Similarity NPD6779 Approved
0.7717 Intermediate Similarity NPD6780 Approved
0.7717 Intermediate Similarity NPD6781 Approved
0.7717 Intermediate Similarity NPD6782 Approved
0.7717 Intermediate Similarity NPD6777 Approved
0.7717 Intermediate Similarity NPD6778 Approved
0.7688 Intermediate Similarity NPD7435 Discontinued
0.7688 Intermediate Similarity NPD4628 Phase 3
0.7679 Intermediate Similarity NPD7768 Phase 2
0.7673 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD1091 Approved
0.7644 Intermediate Similarity NPD5844 Phase 1
0.7625 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD3748 Approved
0.7572 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD1465 Phase 2
0.7558 Intermediate Similarity NPD6232 Discontinued
0.7548 Intermediate Similarity NPD6798 Discontinued
0.7529 Intermediate Similarity NPD7473 Discontinued
0.7516 Intermediate Similarity NPD1933 Approved
0.7515 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7685 Pre-registration
0.75 Intermediate Similarity NPD7698 Approved
0.75 Intermediate Similarity NPD7199 Phase 2
0.75 Intermediate Similarity NPD6233 Phase 2
0.75 Intermediate Similarity NPD7697 Approved
0.75 Intermediate Similarity NPD7696 Phase 3
0.7485 Intermediate Similarity NPD919 Approved
0.7484 Intermediate Similarity NPD7033 Discontinued
0.746 Intermediate Similarity NPD7871 Phase 2
0.746 Intermediate Similarity NPD7870 Phase 2
0.7452 Intermediate Similarity NPD1613 Approved
0.7452 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD1203 Approved
0.7448 Intermediate Similarity NPD7874 Approved
0.7448 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7446 Intermediate Similarity NPD6534 Approved
0.7446 Intermediate Similarity NPD6535 Approved
0.7435 Intermediate Similarity NPD7585 Approved
0.7435 Intermediate Similarity NPD7701 Phase 2
0.7423 Intermediate Similarity NPD6190 Approved
0.7419 Intermediate Similarity NPD6832 Phase 2
0.7417 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD920 Approved
0.7407 Intermediate Similarity NPD1652 Phase 2
0.7407 Intermediate Similarity NPD2800 Approved
0.7399 Intermediate Similarity NPD1247 Approved
0.7396 Intermediate Similarity NPD8151 Discontinued
0.7394 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7228 Approved
0.7383 Intermediate Similarity NPD1548 Phase 1
0.7382 Intermediate Similarity NPD7583 Approved
0.7378 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD5953 Discontinued
0.7358 Intermediate Similarity NPD6651 Approved
0.7351 Intermediate Similarity NPD4360 Phase 2
0.7351 Intermediate Similarity NPD4363 Phase 3
0.7348 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7286 Phase 2
0.7329 Intermediate Similarity NPD2935 Discontinued
0.7326 Intermediate Similarity NPD7699 Phase 2
0.7326 Intermediate Similarity NPD7700 Phase 2
0.7325 Intermediate Similarity NPD2313 Discontinued
0.7321 Intermediate Similarity NPD7458 Discontinued
0.732 Intermediate Similarity NPD7801 Approved
0.732 Intermediate Similarity NPD7783 Phase 2
0.732 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD3926 Phase 2
0.7308 Intermediate Similarity NPD4908 Phase 1
0.7301 Intermediate Similarity NPD1243 Approved
0.7296 Intermediate Similarity NPD5124 Phase 1
0.7296 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD6355 Discontinued
0.7294 Intermediate Similarity NPD37 Approved
0.729 Intermediate Similarity NPD2798 Approved
0.7289 Intermediate Similarity NPD2532 Approved
0.7289 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD2534 Approved
0.7289 Intermediate Similarity NPD2533 Approved
0.7284 Intermediate Similarity NPD7266 Discontinued
0.7283 Intermediate Similarity NPD6234 Discontinued
0.7277 Intermediate Similarity NPD8320 Phase 1
0.7277 Intermediate Similarity NPD8319 Approved
0.7273 Intermediate Similarity NPD3225 Approved
0.7267 Intermediate Similarity NPD4965 Approved
0.7267 Intermediate Similarity NPD4967 Phase 2
0.7267 Intermediate Similarity NPD4966 Approved
0.7263 Intermediate Similarity NPD6823 Phase 2
0.7233 Intermediate Similarity NPD943 Approved
0.7229 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD3268 Approved
0.7215 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD8434 Phase 2
0.7197 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD422 Phase 1
0.719 Intermediate Similarity NPD1610 Phase 2
0.7188 Intermediate Similarity NPD4340 Discontinued
0.7178 Intermediate Similarity NPD2344 Approved
0.717 Intermediate Similarity NPD4062 Phase 3
0.716 Intermediate Similarity NPD2799 Discontinued
0.7143 Intermediate Similarity NPD9717 Approved
0.7135 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD8150 Discontinued
0.7118 Intermediate Similarity NPD3226 Approved
0.7117 Intermediate Similarity NPD6100 Approved
0.7117 Intermediate Similarity NPD6099 Approved
0.7115 Intermediate Similarity NPD2797 Approved
0.7108 Intermediate Similarity NPD3887 Approved
0.7108 Intermediate Similarity NPD2354 Approved
0.7093 Intermediate Similarity NPD6844 Discontinued
0.7081 Intermediate Similarity NPD230 Phase 1
0.7079 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD3027 Phase 3
0.7033 Intermediate Similarity NPD7240 Approved
0.7024 Intermediate Similarity NPD7390 Discontinued
0.7021 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD6212 Phase 3
0.7021 Intermediate Similarity NPD6213 Phase 3
0.7018 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD4288 Approved
0.7006 Intermediate Similarity NPD2309 Approved
0.6994 Remote Similarity NPD7097 Phase 1
0.6988 Remote Similarity NPD2654 Approved
0.6983 Remote Similarity NPD2403 Approved
0.6982 Remote Similarity NPD4662 Approved
0.6982 Remote Similarity NPD4661 Approved
0.6975 Remote Similarity NPD447 Suspended
0.6975 Remote Similarity NPD1899 Clinical (unspecified phase)
0.697 Remote Similarity NPD2346 Discontinued
0.6951 Remote Similarity NPD4308 Phase 3
0.6947 Remote Similarity NPD4361 Phase 2
0.6947 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6946 Remote Similarity NPD6398 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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