Structure

Physi-Chem Properties

Molecular Weight:  742.2
Volume:  665.402
LogP:  -1.118
LogD:  -0.594
LogS:  -3.01
# Rotatable Bonds:  9
TPSA:  328.35
# H-Bond Aceptor:  20
# H-Bond Donor:  12
# Rings:  6
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.099
Synthetic Accessibility Score:  5.283
Fsp3:  0.531
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:  -6.528
MDCK Permeability:  3.052464307984337e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.965
20% Bioavailability (F20%):  0.064
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.223
Plasma Protein Binding (PPB):  78.02108001708984%
Volume Distribution (VD):  0.544
Pgp-substrate:  23.464506149291992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.023
CYP1A2-substrate:  0.014
CYP2C19-inhibitor:  0.018
CYP2C19-substrate:  0.045
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.049
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.095
CYP3A4-inhibitor:  0.015
CYP3A4-substrate:  0.002

ADMET: Excretion

Clearance (CL):  0.81
Half-life (T1/2):  0.805

ADMET: Toxicity

hERG Blockers:  0.521
Human Hepatotoxicity (H-HT):  0.067
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.578
Rat Oral Acute Toxicity:  0.039
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.881
Carcinogencity:  0.069
Eye Corrosion:  0.003
Eye Irritation:  0.078
Respiratory Toxicity:  0.005

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

  Natural Product: NPC292929

Natural Product ID:  NPC292929
Common Name*:   3-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-Trihydroxyoxan-2-Yl]Oxyoxan-2-Yl]Oxy-5,7-Dihydroxy-2-(4-Hydroxyphenyl)Chromen-4-One
IUPAC Name:   3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:  
Standard InCHIKey:  GGLXKKCZDMEVSA-JWDIMEDGSA-N
Standard InCHI:  InChI=1S/C32H38O20/c33-7-16-20(39)23(42)26(45)30(49-16)47-9-17-21(40)24(43)29(52-31-25(44)19(38)14(37)8-46-31)32(50-17)51-28-22(41)18-13(36)5-12(35)6-15(18)48-27(28)10-1-3-11(34)4-2-10/h1-6,14,16-17,19-21,23-26,29-40,42-45H,7-9H2/t14-,16-,17-,19+,20-,21-,23+,24+,25-,26-,29-,30-,31+,32+/m1/s1
SMILES:  OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(cc3)O)[C@@H]([C@H]([C@@H]2O)O)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL447471
PubChem CID:   44566721
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
NPO29234 Aesculus chinensis Species Sapindaceae Eukaryota seeds n.a. n.a. PMID[10579862]
NPO29234 Aesculus chinensis Species Sapindaceae Eukaryota seeds n.a. n.a. PMID[15104496]
NPO29234 Aesculus chinensis Species Sapindaceae Eukaryota seeds n.a. n.a. PMID[25442304]
NPO29234 Aesculus chinensis Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29234 Aesculus chinensis Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29234 Aesculus chinensis Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29234 Aesculus chinensis Species Sapindaceae 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
NPT616 Cell Line MDCK Canis lupus familiaris IC50 = 53.4 ug.mL-1 PMID[458191]
NPT70 Organism Respiratory syncytial virus Respiratory syncytial virus IC50 = 13.4 ug.mL-1 PMID[458191]
NPT2 Others Unspecified Ratio CC50/IC50 = 4.0 n.a. PMID[458191]
NPT336 Organism Human parainfluenza virus 3 Human parainfluenza virus 3 IC50 = 26.7 ug.mL-1 PMID[458191]
NPT2 Others Unspecified Ratio CC50/IC50 = 2.0 n.a. PMID[458191]
NPT742 Organism Influenza A virus Influenza A virus IC50 > 100.0 ug.mL-1 PMID[458191]
NPT2 Others Unspecified Ratio CC50/IC50 < 1.1 n.a. PMID[458191]
NPT336 Organism Human parainfluenza virus 3 Human parainfluenza virus 3 CC50 = 53.4 ug.mL-1 PMID[458191]
NPT742 Organism Influenza A virus Influenza A virus CC50 = 106.9 ug.mL-1 PMID[458191]

☑ 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 NPC292929 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 NPC289667
1.0 High Similarity NPC76831
0.9936 High Similarity NPC32641
0.9936 High Similarity NPC189564
0.9936 High Similarity NPC11432
0.9936 High Similarity NPC12013
0.9936 High Similarity NPC476470
0.9936 High Similarity NPC477613
0.9936 High Similarity NPC186816
0.9936 High Similarity NPC256188
0.9936 High Similarity NPC203145
0.9936 High Similarity NPC221342
0.9936 High Similarity NPC142142
0.9872 High Similarity NPC287889
0.9872 High Similarity NPC135358
0.9806 High Similarity NPC64305
0.9806 High Similarity NPC170052
0.9806 High Similarity NPC135846
0.9806 High Similarity NPC297987
0.9744 High Similarity NPC240306
0.9744 High Similarity NPC475382
0.9744 High Similarity NPC244875
0.9742 High Similarity NPC471079
0.9742 High Similarity NPC136761
0.9742 High Similarity NPC470405
0.9742 High Similarity NPC304741
0.9688 High Similarity NPC470714
0.9688 High Similarity NPC470715
0.9688 High Similarity NPC470716
0.9684 High Similarity NPC64425
0.9682 High Similarity NPC311850
0.9682 High Similarity NPC473644
0.9679 High Similarity NPC473438
0.9679 High Similarity NPC276377
0.9679 High Similarity NPC476215
0.9679 High Similarity NPC249281
0.9679 High Similarity NPC265885
0.9679 High Similarity NPC163242
0.9679 High Similarity NPC215710
0.9679 High Similarity NPC116458
0.9679 High Similarity NPC139320
0.9679 High Similarity NPC246943
0.9679 High Similarity NPC253788
0.9679 High Similarity NPC181465
0.9679 High Similarity NPC173582
0.9625 High Similarity NPC209550
0.9625 High Similarity NPC470712
0.9625 High Similarity NPC277532
0.9625 High Similarity NPC164704
0.9625 High Similarity NPC175429
0.9625 High Similarity NPC138990
0.9615 High Similarity NPC187379
0.9613 High Similarity NPC133671
0.9613 High Similarity NPC77672
0.9613 High Similarity NPC135391
0.9613 High Similarity NPC54802
0.9613 High Similarity NPC78263
0.9613 High Similarity NPC197304
0.9565 High Similarity NPC474522
0.9563 High Similarity NPC5319
0.956 High Similarity NPC262222
0.956 High Similarity NPC298666
0.956 High Similarity NPC68592
0.9554 High Similarity NPC470125
0.9551 High Similarity NPC320283
0.9551 High Similarity NPC473634
0.9551 High Similarity NPC111929
0.9551 High Similarity NPC22062
0.9551 High Similarity NPC138811
0.9551 High Similarity NPC41121
0.9551 High Similarity NPC472459
0.9548 High Similarity NPC307938
0.9548 High Similarity NPC323593
0.9548 High Similarity NPC203500
0.9509 High Similarity NPC219043
0.9509 High Similarity NPC14187
0.9509 High Similarity NPC202908
0.9509 High Similarity NPC292019
0.9509 High Similarity NPC122467
0.9509 High Similarity NPC231787
0.9509 High Similarity NPC48984
0.9494 High Similarity NPC298171
0.949 High Similarity NPC153342
0.949 High Similarity NPC142860
0.949 High Similarity NPC271270
0.949 High Similarity NPC97285
0.949 High Similarity NPC246469
0.949 High Similarity NPC473623
0.9487 High Similarity NPC44931
0.9487 High Similarity NPC473512
0.9487 High Similarity NPC108831
0.9487 High Similarity NPC182634
0.9487 High Similarity NPC129827
0.9487 High Similarity NPC65003
0.9451 High Similarity NPC251417
0.9451 High Similarity NPC89052
0.943 High Similarity NPC224530
0.943 High Similarity NPC85707
0.943 High Similarity NPC216496
0.943 High Similarity NPC129217
0.943 High Similarity NPC159579
0.943 High Similarity NPC48093
0.943 High Similarity NPC282169
0.943 High Similarity NPC101636
0.943 High Similarity NPC259957
0.9423 High Similarity NPC295613
0.9423 High Similarity NPC473657
0.9419 High Similarity NPC83283
0.9419 High Similarity NPC39360
0.9419 High Similarity NPC143851
0.9419 High Similarity NPC210003
0.9419 High Similarity NPC29763
0.9394 High Similarity NPC192539
0.9383 High Similarity NPC255157
0.9383 High Similarity NPC96605
0.9383 High Similarity NPC254855
0.9383 High Similarity NPC280642
0.9383 High Similarity NPC218161
0.9383 High Similarity NPC136042
0.9383 High Similarity NPC67326
0.9383 High Similarity NPC259896
0.9383 High Similarity NPC156869
0.9383 High Similarity NPC29958
0.9375 High Similarity NPC129264
0.9375 High Similarity NPC19240
0.9375 High Similarity NPC85751
0.9375 High Similarity NPC205824
0.9371 High Similarity NPC150164
0.9371 High Similarity NPC190450
0.9371 High Similarity NPC27942
0.9363 High Similarity NPC288084
0.9359 High Similarity NPC95090
0.9359 High Similarity NPC27408
0.9359 High Similarity NPC26195
0.9359 High Similarity NPC169248
0.9359 High Similarity NPC39351
0.9359 High Similarity NPC97052
0.9359 High Similarity NPC72649
0.9329 High Similarity NPC19108
0.9329 High Similarity NPC473327
0.9329 High Similarity NPC476472
0.9329 High Similarity NPC16194
0.9329 High Similarity NPC220173
0.9329 High Similarity NPC294815
0.9325 High Similarity NPC471725
0.9325 High Similarity NPC11847
0.9325 High Similarity NPC471748
0.9325 High Similarity NPC221288
0.9325 High Similarity NPC176740
0.9325 High Similarity NPC101399
0.9325 High Similarity NPC180918
0.9325 High Similarity NPC217822
0.9325 High Similarity NPC33054
0.9325 High Similarity NPC26230
0.9325 High Similarity NPC134532
0.9325 High Similarity NPC203259
0.9325 High Similarity NPC155877
0.9325 High Similarity NPC60735
0.9313 High Similarity NPC257566
0.9313 High Similarity NPC80068
0.9313 High Similarity NPC66087
0.9313 High Similarity NPC121703
0.9313 High Similarity NPC124155
0.9313 High Similarity NPC278419
0.9313 High Similarity NPC179198
0.9308 High Similarity NPC47923
0.9308 High Similarity NPC473516
0.9308 High Similarity NPC303913
0.9304 High Similarity NPC104677
0.9299 High Similarity NPC170475
0.9299 High Similarity NPC206378
0.9273 High Similarity NPC473862
0.9273 High Similarity NPC89127
0.9273 High Similarity NPC471669
0.9264 High Similarity NPC188815
0.9264 High Similarity NPC92815
0.9264 High Similarity NPC469344
0.9264 High Similarity NPC285197
0.9264 High Similarity NPC67105
0.9264 High Similarity NPC95866
0.9259 High Similarity NPC275454
0.9255 High Similarity NPC139060
0.9255 High Similarity NPC72016
0.925 High Similarity NPC259834
0.925 High Similarity NPC44947
0.925 High Similarity NPC131745
0.9245 High Similarity NPC321478
0.9241 High Similarity NPC156457
0.9241 High Similarity NPC197896
0.9241 High Similarity NPC6985
0.9241 High Similarity NPC313163
0.9241 High Similarity NPC161749
0.9241 High Similarity NPC258035
0.9241 High Similarity NPC60966
0.9241 High Similarity NPC122809
0.9231 High Similarity NPC259182
0.9231 High Similarity NPC259767
0.9231 High Similarity NPC88484
0.9231 High Similarity NPC121001
0.9226 High Similarity NPC249560

  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 NPC292929 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
0.9563 High Similarity NPD7804 Clinical (unspecified phase)
0.9448 High Similarity NPD7808 Phase 3
0.9387 High Similarity NPD7251 Discontinued
0.9325 High Similarity NPD6797 Phase 2
0.9241 High Similarity NPD4381 Clinical (unspecified phase)
0.9146 High Similarity NPD7472 Approved
0.9085 High Similarity NPD7054 Approved
0.903 High Similarity NPD7074 Phase 3
0.8869 High Similarity NPD4338 Clinical (unspecified phase)
0.865 High Similarity NPD7075 Discontinued
0.8625 High Similarity NPD4380 Phase 2
0.8571 High Similarity NPD3818 Discontinued
0.8563 High Similarity NPD6168 Clinical (unspecified phase)
0.8563 High Similarity NPD6166 Phase 2
0.8563 High Similarity NPD6167 Clinical (unspecified phase)
0.8553 High Similarity NPD5403 Approved
0.8519 High Similarity NPD6801 Discontinued
0.8466 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8428 Intermediate Similarity NPD5401 Approved
0.8365 Intermediate Similarity NPD6799 Approved
0.8333 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD3817 Phase 2
0.8303 Intermediate Similarity NPD5402 Approved
0.828 Intermediate Similarity NPD1549 Phase 2
0.8208 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1934 Approved
0.8161 Intermediate Similarity NPD6559 Discontinued
0.8156 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD1512 Approved
0.8133 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8068 Intermediate Similarity NPD8312 Approved
0.8068 Intermediate Similarity NPD8313 Approved
0.8061 Intermediate Similarity NPD6599 Discontinued
0.8036 Intermediate Similarity NPD3882 Suspended
0.8025 Intermediate Similarity NPD1511 Approved
0.8024 Intermediate Similarity NPD2801 Approved
0.8024 Intermediate Similarity NPD8455 Phase 2
0.8012 Intermediate Similarity NPD7411 Suspended
0.7975 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD1510 Phase 2
0.7931 Intermediate Similarity NPD3751 Discontinued
0.7929 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD2796 Approved
0.7917 Intermediate Similarity NPD7819 Suspended
0.7907 Intermediate Similarity NPD3787 Discontinued
0.7849 Intermediate Similarity NPD6959 Discontinued
0.7816 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD1240 Approved
0.7696 Intermediate Similarity NPD7584 Approved
0.7632 Intermediate Similarity NPD7696 Phase 3
0.7632 Intermediate Similarity NPD7698 Approved
0.7632 Intermediate Similarity NPD7697 Approved
0.7632 Intermediate Similarity NPD7435 Discontinued
0.7625 Intermediate Similarity NPD1607 Approved
0.7622 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD3750 Approved
0.7617 Intermediate Similarity NPD8151 Discontinued
0.7616 Intermediate Similarity NPD7768 Phase 2
0.7595 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD5494 Approved
0.7566 Intermediate Similarity NPD6782 Approved
0.7566 Intermediate Similarity NPD6776 Approved
0.7566 Intermediate Similarity NPD6778 Approved
0.7566 Intermediate Similarity NPD6781 Approved
0.7566 Intermediate Similarity NPD6780 Approved
0.7566 Intermediate Similarity NPD6779 Approved
0.7566 Intermediate Similarity NPD6777 Approved
0.7565 Intermediate Similarity NPD7701 Phase 2
0.7538 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD7783 Phase 2
0.7515 Intermediate Similarity NPD1653 Approved
0.7514 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7870 Phase 2
0.75 Intermediate Similarity NPD8319 Approved
0.75 Intermediate Similarity NPD8320 Phase 1
0.75 Intermediate Similarity NPD7871 Phase 2
0.7487 Intermediate Similarity NPD7874 Approved
0.7487 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1551 Phase 2
0.7471 Intermediate Similarity NPD3749 Approved
0.746 Intermediate Similarity NPD7700 Phase 2
0.746 Intermediate Similarity NPD7699 Phase 2
0.7459 Intermediate Similarity NPD7685 Pre-registration
0.743 Intermediate Similarity NPD7228 Approved
0.741 Intermediate Similarity NPD4628 Phase 3
0.7399 Intermediate Similarity NPD1465 Phase 2
0.7394 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5844 Phase 1
0.7374 Intermediate Similarity NPD7473 Discontinued
0.736 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD7801 Approved
0.7355 Intermediate Similarity NPD1091 Approved
0.7349 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD3748 Approved
0.7303 Intermediate Similarity NPD6232 Discontinued
0.7302 Intermediate Similarity NPD6535 Approved
0.7302 Intermediate Similarity NPD6534 Approved
0.7297 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD7585 Approved
0.7273 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD7458 Discontinued
0.7267 Intermediate Similarity NPD6798 Discontinued
0.7258 Intermediate Similarity NPD8434 Phase 2
0.7251 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD6832 Phase 2
0.7247 Intermediate Similarity NPD7199 Phase 2
0.7245 Intermediate Similarity NPD7583 Approved
0.7239 Intermediate Similarity NPD1933 Approved
0.7232 Intermediate Similarity NPD919 Approved
0.7229 Intermediate Similarity NPD7266 Discontinued
0.7222 Intermediate Similarity NPD6233 Phase 2
0.7216 Intermediate Similarity NPD6823 Phase 2
0.7212 Intermediate Similarity NPD7033 Discontinued
0.7198 Intermediate Similarity NPD7286 Phase 2
0.7195 Intermediate Similarity NPD6651 Approved
0.7178 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1613 Approved
0.7174 Intermediate Similarity NPD7240 Approved
0.717 Intermediate Similarity NPD1203 Approved
0.7166 Intermediate Similarity NPD8150 Discontinued
0.716 Intermediate Similarity NPD6190 Approved
0.7151 Intermediate Similarity NPD1247 Approved
0.7151 Intermediate Similarity NPD920 Approved
0.7143 Intermediate Similarity NPD2800 Approved
0.7143 Intermediate Similarity NPD1652 Phase 2
0.7135 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6355 Discontinued
0.7134 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD4363 Phase 3
0.712 Intermediate Similarity NPD4360 Phase 2
0.712 Intermediate Similarity NPD5953 Discontinued
0.7118 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1548 Phase 1
0.7072 Intermediate Similarity NPD3926 Phase 2
0.7066 Intermediate Similarity NPD2935 Discontinued
0.7055 Intermediate Similarity NPD2313 Discontinued
0.7045 Intermediate Similarity NPD37 Approved
0.7041 Intermediate Similarity NPD1243 Approved
0.7039 Intermediate Similarity NPD6234 Discontinued
0.7037 Intermediate Similarity NPD4908 Phase 1
0.7035 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD2533 Approved
0.7035 Intermediate Similarity NPD2532 Approved
0.7035 Intermediate Similarity NPD2534 Approved
0.703 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD5124 Phase 1
0.7022 Intermediate Similarity NPD4966 Approved
0.7022 Intermediate Similarity NPD4967 Phase 2
0.7022 Intermediate Similarity NPD4965 Approved
0.7019 Intermediate Similarity NPD2798 Approved
0.7 Intermediate Similarity NPD3225 Approved
0.6989 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6977 Remote Similarity NPD6143 Clinical (unspecified phase)
0.697 Remote Similarity NPD943 Approved
0.6964 Remote Similarity NPD6099 Approved
0.6964 Remote Similarity NPD6100 Approved
0.6951 Remote Similarity NPD3268 Approved
0.6951 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6949 Remote Similarity NPD6844 Discontinued
0.6946 Remote Similarity NPD7097 Phase 1
0.6933 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6928 Remote Similarity NPD4340 Discontinued
0.6923 Remote Similarity NPD2344 Approved
0.6918 Remote Similarity NPD422 Phase 1
0.6918 Remote Similarity NPD1610 Phase 2
0.6909 Remote Similarity NPD4062 Phase 3
0.6905 Remote Similarity NPD2799 Discontinued
0.6891 Remote Similarity NPD6212 Phase 3
0.6891 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6891 Remote Similarity NPD6213 Phase 3
0.6879 Remote Similarity NPD7390 Discontinued
0.6875 Remote Similarity NPD3226 Approved
0.6875 Remote Similarity NPD9717 Approved
0.6871 Remote Similarity NPD1530 Clinical (unspecified phase)
0.686 Remote Similarity NPD3887 Approved
0.686 Remote Similarity NPD2354 Approved
0.6852 Remote Similarity NPD2797 Approved
0.6829 Remote Similarity NPD7930 Approved
0.6826 Remote Similarity NPD230 Phase 1
0.6805 Remote Similarity NPD651 Clinical (unspecified phase)
0.6802 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6788 Remote Similarity NPD3027 Phase 3
0.678 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6778 Remote Similarity NPD4288 Approved
0.6768 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6766 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6763 Remote Similarity NPD2309 Approved
0.6757 Remote Similarity NPD2403 Approved
0.675 Remote Similarity NPD7680 Approved
0.6744 Remote Similarity NPD2654 Approved
0.6743 Remote Similarity NPD4661 Approved
0.6743 Remote Similarity NPD4662 Approved
0.6735 Remote Similarity NPD4361 Phase 2
0.6735 Remote Similarity NPD4362 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