Structure

Physi-Chem Properties

Molecular Weight:  578.16
Volume:  534.737
LogP:  0.845
LogD:  -0.03
LogS:  -3.82
# Rotatable Bonds:  5
TPSA:  239.97
# H-Bond Aceptor:  14
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.175
Synthetic Accessibility Score:  4.733
Fsp3:  0.444
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.427
MDCK Permeability:  1.4651114724983927e-05
Pgp-inhibitor:  0.016
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.956
20% Bioavailability (F20%):  0.081
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.055
Plasma Protein Binding (PPB):  85.35285949707031%
Volume Distribution (VD):  0.659
Pgp-substrate:  15.131881713867188%

ADMET: Metabolism

CYP1A2-inhibitor:  0.063
CYP1A2-substrate:  0.036
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.012
CYP2C9-substrate:  0.252
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.143
CYP3A4-inhibitor:  0.031
CYP3A4-substrate:  0.009

ADMET: Excretion

Clearance (CL):  1.618
Half-life (T1/2):  0.666

ADMET: Toxicity

hERG Blockers:  0.234
Human Hepatotoxicity (H-HT):  0.209
Drug-inuced Liver Injury (DILI):  0.979
AMES Toxicity:  0.811
Rat Oral Acute Toxicity:  0.041
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.723
Carcinogencity:  0.077
Eye Corrosion:  0.003
Eye Irritation:  0.042
Respiratory Toxicity:  0.082

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

  Natural Product: NPC44947

Natural Product ID:  NPC44947
Common Name*:   Vitexin-2''-O-Rhamnoside
IUPAC Name:   8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:  
Standard InCHIKey:  LYGPBZVKGHHTIE-HUBYJIGHSA-N
Standard InCHI:  InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3/t9-,16+,19-,20+,21+,22-,23+,25-,26+,27-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1c1c(cc(c2c(=O)cc(c3ccc(cc3)O)oc12)O)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1685070
PubChem CID:   5282151
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001737] Flavonoid C-glycosides
            • [CHEMONTID:0003535] Flavonoid 8-C-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
NPO14602 Vitex negundo Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[12828478]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. root n.a. PMID[15520511]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[15620254]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. fruit n.a. PMID[15739361]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[1624939]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17027268]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19715321]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19931461]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23403897]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. seed n.a. PMID[23845552]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota seeds n.a. n.a. PMID[23999046]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24078 Pyrrosia petiolosa Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1639 Pyrrosia lingua Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24078 Pyrrosia petiolosa Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1639 Pyrrosia lingua Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1639 Pyrrosia lingua Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1639 Pyrrosia lingua Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16445 Pyrrosia tricuspis Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24078 Pyrrosia petiolosa Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12194 Grataegus pinnatifida n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1639 Pyrrosia lingua Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29331 Pyrrosia sheareri Species Polypodiaceae 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
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 25.95 % PMID[526695]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -3.3 % PMID[526695]

☑ 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 NPC44947 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
0.9935 High Similarity NPC124155
0.9935 High Similarity NPC257566
0.9935 High Similarity NPC47923
0.9805 High Similarity NPC303913
0.9742 High Similarity NPC190450
0.9742 High Similarity NPC131745
0.9742 High Similarity NPC259834
0.974 High Similarity NPC472320
0.9739 High Similarity NPC473512
0.9739 High Similarity NPC129827
0.9739 High Similarity NPC65003
0.9739 High Similarity NPC44931
0.9684 High Similarity NPC5319
0.9679 High Similarity NPC179198
0.9679 High Similarity NPC66087
0.9679 High Similarity NPC278419
0.9679 High Similarity NPC183672
0.9675 High Similarity NPC473634
0.9675 High Similarity NPC22062
0.9675 High Similarity NPC73511
0.9675 High Similarity NPC138811
0.9673 High Similarity NPC206378
0.9623 High Similarity NPC78734
0.9623 High Similarity NPC150767
0.9613 High Similarity NPC187379
0.9613 High Similarity NPC473623
0.9613 High Similarity NPC97285
0.9613 High Similarity NPC246469
0.9613 High Similarity NPC142860
0.9613 High Similarity NPC271270
0.961 High Similarity NPC23817
0.961 High Similarity NPC313163
0.961 High Similarity NPC161749
0.961 High Similarity NPC258035
0.961 High Similarity NPC197896
0.961 High Similarity NPC156457
0.9608 High Similarity NPC470604
0.9608 High Similarity NPC97052
0.9608 High Similarity NPC470603
0.9608 High Similarity NPC26195
0.9608 High Similarity NPC95090
0.9608 High Similarity NPC72649
0.9608 High Similarity NPC27408
0.9608 High Similarity NPC169248
0.9608 High Similarity NPC470605
0.9608 High Similarity NPC39351
0.9563 High Similarity NPC256760
0.9551 High Similarity NPC276377
0.9551 High Similarity NPC163242
0.9551 High Similarity NPC215710
0.9551 High Similarity NPC181465
0.9551 High Similarity NPC473438
0.9551 High Similarity NPC265885
0.9551 High Similarity NPC249281
0.9551 High Similarity NPC476215
0.9551 High Similarity NPC101636
0.9551 High Similarity NPC116458
0.9551 High Similarity NPC246943
0.9551 High Similarity NPC253788
0.9551 High Similarity NPC139320
0.9551 High Similarity NPC173582
0.9548 High Similarity NPC308265
0.9545 High Similarity NPC45165
0.9545 High Similarity NPC473657
0.9545 High Similarity NPC170475
0.9545 High Similarity NPC295613
0.9542 High Similarity NPC83283
0.9542 High Similarity NPC109594
0.9542 High Similarity NPC78021
0.9542 High Similarity NPC326592
0.9542 High Similarity NPC87304
0.9542 High Similarity NPC29763
0.9542 High Similarity NPC143851
0.9542 High Similarity NPC268950
0.9542 High Similarity NPC112701
0.9542 High Similarity NPC210003
0.9542 High Similarity NPC211158
0.9542 High Similarity NPC39360
0.9542 High Similarity NPC108706
0.9542 High Similarity NPC106625
0.9503 High Similarity NPC208668
0.95 High Similarity NPC218488
0.95 High Similarity NPC76047
0.949 High Similarity NPC475382
0.949 High Similarity NPC240306
0.949 High Similarity NPC298171
0.9487 High Similarity NPC271479
0.9487 High Similarity NPC304741
0.9487 High Similarity NPC471079
0.9487 High Similarity NPC136761
0.9487 High Similarity NPC470405
0.9487 High Similarity NPC153342
0.9484 High Similarity NPC108831
0.9484 High Similarity NPC182634
0.9484 High Similarity NPC470606
0.9484 High Similarity NPC60966
0.9481 High Similarity NPC99233
0.9477 High Similarity NPC56232
0.9477 High Similarity NPC150123
0.9477 High Similarity NPC121001
0.9477 High Similarity NPC244583
0.9477 High Similarity NPC161881
0.9477 High Similarity NPC10807
0.9477 High Similarity NPC259182
0.9444 High Similarity NPC294629
0.9434 High Similarity NPC115674
0.9434 High Similarity NPC210073
0.9434 High Similarity NPC70441
0.943 High Similarity NPC311850
0.943 High Similarity NPC473644
0.9427 High Similarity NPC297987
0.9427 High Similarity NPC135846
0.9427 High Similarity NPC64305
0.9427 High Similarity NPC170052
0.9423 High Similarity NPC43761
0.9423 High Similarity NPC41121
0.9423 High Similarity NPC320283
0.9423 High Similarity NPC472459
0.9423 High Similarity NPC470607
0.9423 High Similarity NPC111929
0.9419 High Similarity NPC203500
0.9419 High Similarity NPC261866
0.9419 High Similarity NPC323593
0.9419 High Similarity NPC127406
0.9419 High Similarity NPC307938
0.9412 High Similarity NPC209846
0.9412 High Similarity NPC328740
0.9412 High Similarity NPC289774
0.9412 High Similarity NPC477897
0.9383 High Similarity NPC25724
0.9383 High Similarity NPC213052
0.9379 High Similarity NPC231194
0.9379 High Similarity NPC51326
0.9375 High Similarity NPC477502
0.9371 High Similarity NPC287889
0.9371 High Similarity NPC135358
0.9367 High Similarity NPC472876
0.9363 High Similarity NPC200708
0.9359 High Similarity NPC135391
0.9359 High Similarity NPC6985
0.9359 High Similarity NPC43638
0.9359 High Similarity NPC77672
0.9359 High Similarity NPC122809
0.9359 High Similarity NPC78263
0.9359 High Similarity NPC197304
0.9359 High Similarity NPC54802
0.9359 High Similarity NPC133671
0.9355 High Similarity NPC87404
0.9355 High Similarity NPC92395
0.9355 High Similarity NPC304745
0.9355 High Similarity NPC111341
0.9351 High Similarity NPC166067
0.9351 High Similarity NPC259767
0.9351 High Similarity NPC475790
0.9351 High Similarity NPC88484
0.9346 High Similarity NPC191154
0.9346 High Similarity NPC38775
0.9317 High Similarity NPC209296
0.9317 High Similarity NPC259905
0.9317 High Similarity NPC293629
0.9317 High Similarity NPC195257
0.9317 High Similarity NPC43587
0.9313 High Similarity NPC64425
0.9313 High Similarity NPC221342
0.9313 High Similarity NPC203145
0.9313 High Similarity NPC189564
0.9313 High Similarity NPC236934
0.9313 High Similarity NPC142142
0.9313 High Similarity NPC477613
0.9313 High Similarity NPC186816
0.9313 High Similarity NPC5778
0.9313 High Similarity NPC11432
0.9313 High Similarity NPC8856
0.9313 High Similarity NPC262222
0.9313 High Similarity NPC476470
0.9313 High Similarity NPC68592
0.9313 High Similarity NPC256188
0.9313 High Similarity NPC12013
0.9313 High Similarity NPC298666
0.9313 High Similarity NPC32641
0.9308 High Similarity NPC88023
0.9308 High Similarity NPC19709
0.9308 High Similarity NPC309025
0.9308 High Similarity NPC243930
0.9308 High Similarity NPC29830
0.9304 High Similarity NPC224530
0.9304 High Similarity NPC210961
0.9304 High Similarity NPC216496
0.9304 High Similarity NPC477629
0.9304 High Similarity NPC472994
0.9304 High Similarity NPC470125
0.9304 High Similarity NPC259957
0.9304 High Similarity NPC270675
0.9304 High Similarity NPC48093
0.9304 High Similarity NPC85707
0.9304 High Similarity NPC159579
0.9304 High Similarity NPC477628
0.9304 High Similarity NPC129217
0.9304 High Similarity NPC195685
0.9295 High Similarity NPC17521

  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 NPC44947 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
0.9684 High Similarity NPD7804 Clinical (unspecified phase)
0.961 High Similarity NPD4381 Clinical (unspecified phase)
0.9317 High Similarity NPD7054 Approved
0.9259 High Similarity NPD7472 Approved
0.9259 High Similarity NPD7074 Phase 3
0.9221 High Similarity NPD4380 Phase 2
0.9202 High Similarity NPD6797 Phase 2
0.9146 High Similarity NPD7251 Discontinued
0.9091 High Similarity NPD7808 Phase 3
0.8902 High Similarity NPD3818 Discontinued
0.8875 High Similarity NPD7075 Discontinued
0.8805 High Similarity NPD2393 Clinical (unspecified phase)
0.8802 High Similarity NPD6559 Discontinued
0.878 High Similarity NPD6167 Clinical (unspecified phase)
0.878 High Similarity NPD6168 Clinical (unspecified phase)
0.878 High Similarity NPD6166 Phase 2
0.8774 High Similarity NPD4378 Clinical (unspecified phase)
0.875 High Similarity NPD4338 Clinical (unspecified phase)
0.8742 High Similarity NPD6801 Discontinued
0.8688 High Similarity NPD7096 Clinical (unspecified phase)
0.8634 High Similarity NPD8443 Clinical (unspecified phase)
0.8625 High Similarity NPD1934 Approved
0.8562 High Similarity NPD7411 Suspended
0.8562 High Similarity NPD1550 Clinical (unspecified phase)
0.8562 High Similarity NPD1552 Clinical (unspecified phase)
0.8535 High Similarity NPD7410 Clinical (unspecified phase)
0.8506 High Similarity NPD1549 Phase 2
0.8485 Intermediate Similarity NPD6959 Discontinued
0.8377 Intermediate Similarity NPD2796 Approved
0.8344 Intermediate Similarity NPD7819 Suspended
0.8344 Intermediate Similarity NPD2801 Approved
0.8333 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD5403 Approved
0.8312 Intermediate Similarity NPD1510 Phase 2
0.8293 Intermediate Similarity NPD3817 Phase 2
0.8266 Intermediate Similarity NPD8313 Approved
0.8266 Intermediate Similarity NPD8312 Approved
0.8249 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD1511 Approved
0.8239 Intermediate Similarity NPD6799 Approved
0.8232 Intermediate Similarity NPD8455 Phase 2
0.8204 Intermediate Similarity NPD5494 Approved
0.8187 Intermediate Similarity NPD5401 Approved
0.8182 Intermediate Similarity NPD5402 Approved
0.8162 Intermediate Similarity NPD7584 Approved
0.8137 Intermediate Similarity NPD1512 Approved
0.8092 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD1240 Approved
0.8049 Intermediate Similarity NPD6599 Discontinued
0.8024 Intermediate Similarity NPD7768 Phase 2
0.8024 Intermediate Similarity NPD3882 Suspended
0.7977 Intermediate Similarity NPD5844 Phase 1
0.7949 Intermediate Similarity NPD1607 Approved
0.7937 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD3750 Approved
0.7935 Intermediate Similarity NPD6781 Approved
0.7935 Intermediate Similarity NPD6778 Approved
0.7935 Intermediate Similarity NPD6782 Approved
0.7935 Intermediate Similarity NPD6779 Approved
0.7935 Intermediate Similarity NPD6780 Approved
0.7935 Intermediate Similarity NPD6776 Approved
0.7935 Intermediate Similarity NPD6777 Approved
0.7895 Intermediate Similarity NPD6232 Discontinued
0.7884 Intermediate Similarity NPD8151 Discontinued
0.7875 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD7473 Discontinued
0.7826 Intermediate Similarity NPD4628 Phase 3
0.7816 Intermediate Similarity NPD7228 Approved
0.7816 Intermediate Similarity NPD3751 Discontinued
0.7807 Intermediate Similarity NPD7697 Approved
0.7807 Intermediate Similarity NPD7698 Approved
0.7807 Intermediate Similarity NPD7435 Discontinued
0.7807 Intermediate Similarity NPD7696 Phase 3
0.7801 Intermediate Similarity NPD7783 Phase 2
0.7801 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD3787 Discontinued
0.7772 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD7458 Discontinued
0.7765 Intermediate Similarity NPD3749 Approved
0.7764 Intermediate Similarity NPD2800 Approved
0.7758 Intermediate Similarity NPD920 Approved
0.7737 Intermediate Similarity NPD7701 Phase 2
0.7737 Intermediate Similarity NPD7585 Approved
0.7711 Intermediate Similarity NPD1653 Approved
0.7702 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1465 Phase 2
0.7692 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD2935 Discontinued
0.7688 Intermediate Similarity NPD1551 Phase 2
0.7684 Intermediate Similarity NPD7583 Approved
0.7684 Intermediate Similarity NPD5953 Discontinued
0.7672 Intermediate Similarity NPD7871 Phase 2
0.7672 Intermediate Similarity NPD7870 Phase 2
0.7663 Intermediate Similarity NPD6535 Approved
0.7663 Intermediate Similarity NPD4363 Phase 3
0.7663 Intermediate Similarity NPD4360 Phase 2
0.7663 Intermediate Similarity NPD6534 Approved
0.766 Intermediate Similarity NPD6823 Phase 2
0.7654 Intermediate Similarity NPD1243 Approved
0.7651 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7637 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD2533 Approved
0.7636 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD2534 Approved
0.7636 Intermediate Similarity NPD2532 Approved
0.7634 Intermediate Similarity NPD7699 Phase 2
0.7634 Intermediate Similarity NPD7700 Phase 2
0.763 Intermediate Similarity NPD7199 Phase 2
0.7625 Intermediate Similarity NPD3748 Approved
0.7622 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD6651 Approved
0.758 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD2313 Discontinued
0.7571 Intermediate Similarity NPD7286 Phase 2
0.7565 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD7874 Approved
0.7547 Intermediate Similarity NPD5124 Phase 1
0.7547 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD7685 Pre-registration
0.7529 Intermediate Similarity NPD37 Approved
0.7526 Intermediate Similarity NPD7801 Approved
0.7516 Intermediate Similarity NPD7033 Discontinued
0.7516 Intermediate Similarity NPD2799 Discontinued
0.7514 Intermediate Similarity NPD6234 Discontinued
0.7514 Intermediate Similarity NPD919 Approved
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD4965 Approved
0.75 Intermediate Similarity NPD4967 Phase 2
0.7487 Intermediate Similarity NPD8320 Phase 1
0.7487 Intermediate Similarity NPD8319 Approved
0.7484 Intermediate Similarity NPD1613 Approved
0.7484 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7390 Discontinued
0.7456 Intermediate Similarity NPD3226 Approved
0.7452 Intermediate Similarity NPD4908 Phase 1
0.7451 Intermediate Similarity NPD1091 Approved
0.7444 Intermediate Similarity NPD7240 Approved
0.7443 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD1933 Approved
0.7436 Intermediate Similarity NPD2798 Approved
0.7429 Intermediate Similarity NPD1247 Approved
0.7423 Intermediate Similarity NPD7266 Discontinued
0.7419 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6212 Phase 3
0.7419 Intermediate Similarity NPD6213 Phase 3
0.7377 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD6832 Phase 2
0.7338 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD8150 Discontinued
0.7333 Intermediate Similarity NPD1652 Phase 2
0.7321 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD2346 Discontinued
0.7317 Intermediate Similarity NPD2344 Approved
0.7273 Intermediate Similarity NPD2424 Discontinued
0.7267 Intermediate Similarity NPD943 Approved
0.7261 Intermediate Similarity NPD1203 Approved
0.7256 Intermediate Similarity NPD6099 Approved
0.7256 Intermediate Similarity NPD6100 Approved
0.7251 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD6798 Discontinued
0.725 Intermediate Similarity NPD3268 Approved
0.7249 Intermediate Similarity NPD4361 Phase 2
0.7249 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD3926 Phase 2
0.7243 Intermediate Similarity NPD8434 Phase 2
0.7239 Intermediate Similarity NPD7097 Phase 1
0.7233 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD1610 Phase 2
0.7207 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD5710 Approved
0.7191 Intermediate Similarity NPD5711 Approved
0.719 Intermediate Similarity NPD1548 Phase 1
0.7188 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD3027 Phase 3
0.7186 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD2797 Approved
0.715 Intermediate Similarity NPD7930 Approved
0.7143 Intermediate Similarity NPD2309 Approved
0.7126 Intermediate Similarity NPD6844 Discontinued
0.7126 Intermediate Similarity NPD6674 Discontinued
0.7117 Intermediate Similarity NPD230 Phase 1
0.7117 Intermediate Similarity NPD6355 Discontinued
0.7115 Intermediate Similarity NPD422 Phase 1
0.7104 Intermediate Similarity NPD3823 Discontinued
0.7101 Intermediate Similarity NPD5058 Phase 3
0.7099 Intermediate Similarity NPD6233 Phase 2
0.7092 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD4308 Phase 3
0.7089 Intermediate Similarity NPD3225 Approved
0.707 Intermediate Similarity NPD9717 Approved
0.7069 Intermediate Similarity NPD5889 Approved
0.7069 Intermediate Similarity NPD5890 Approved
0.7047 Intermediate Similarity NPD7237 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