Structure

Physi-Chem Properties

Molecular Weight:  758.19
Volume:  674.192
LogP:  -1.331
LogD:  -0.715
LogS:  -3.4
# Rotatable Bonds:  9
TPSA:  348.58
# H-Bond Aceptor:  21
# H-Bond Donor:  13
# Rings:  6
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.098
Synthetic Accessibility Score:  5.357
Fsp3:  0.531
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.612
MDCK Permeability:  5.2160346967866644e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.958
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.292
Plasma Protein Binding (PPB):  75.68065643310547%
Volume Distribution (VD):  0.594
Pgp-substrate:  22.07932472229004%

ADMET: Metabolism

CYP1A2-inhibitor:  0.037
CYP1A2-substrate:  0.011
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.048
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.055
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.101
CYP3A4-inhibitor:  0.008
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  0.965
Half-life (T1/2):  0.824

ADMET: Toxicity

hERG Blockers:  0.507
Human Hepatotoxicity (H-HT):  0.102
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.508
Rat Oral Acute Toxicity:  0.01
Maximum Recommended Daily Dose:  0.0
Skin Sensitization:  0.567
Carcinogencity:  0.033
Eye Corrosion:  0.003
Eye Irritation:  0.032
Respiratory Toxicity:  0.004

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

  Natural Product: NPC219043

Natural Product ID:  NPC219043
Common Name*:   3-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(Hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-Trihydroxyoxan-2-Yl]Oxyoxan-2-Yl]Oxy-5,7-Dihydroxy-2-[4-Hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyphenyl]Chromen-4-One
IUPAC Name:   3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms:  
Standard InCHIKey:  PNRUTIKOCMXSIP-JYVKGLRRSA-N
Standard InCHI:  InChI=1S/C32H38O21/c33-6-16-20(40)23(43)26(46)31(50-16)49-14-3-9(1-2-11(14)36)27-28(22(42)18-12(37)4-10(35)5-15(18)48-27)52-32-29(24(44)21(41)17(7-34)51-32)53-30-25(45)19(39)13(38)8-47-30/h1-5,13,16-17,19-21,23-26,29-41,43-46H,6-8H2/t13-,16-,17-,19+,20-,21-,23+,24+,25-,26-,29-,30+,31-,32+/m1/s1
SMILES:  c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL474596
PubChem CID:   44566719
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 = 215.0 ug.mL-1 PMID[480849]
NPT70 Organism Respiratory syncytial virus Respiratory syncytial virus IC50 = 26.9 ug.mL-1 PMID[480849]
NPT2 Others Unspecified Ratio CC50/IC50 = 8.0 n.a. PMID[480849]
NPT336 Organism Human parainfluenza virus 3 Human parainfluenza virus 3 IC50 = 53.8 ug.mL-1 PMID[480849]
NPT2 Others Unspecified Ratio CC50/IC50 = 4.0 n.a. PMID[480849]
NPT742 Organism Influenza A virus Influenza A virus IC50 > 500.0 ug.mL-1 PMID[480849]
NPT336 Organism Human parainfluenza virus 3 Human parainfluenza virus 3 CC50 = 215.0 ug.mL-1 PMID[480849]
NPT742 Organism Influenza A virus Influenza A virus CC50 > 322.5 ug.mL-1 PMID[480849]

☑ 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 NPC219043 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
0.9939 High Similarity NPC89052
0.9939 High Similarity NPC251417
0.9879 High Similarity NPC192539
0.9878 High Similarity NPC48984
0.9878 High Similarity NPC14187
0.9878 High Similarity NPC292019
0.9878 High Similarity NPC122467
0.9878 High Similarity NPC202908
0.9817 High Similarity NPC16194
0.9817 High Similarity NPC19108
0.9817 High Similarity NPC476472
0.9817 High Similarity NPC220173
0.9817 High Similarity NPC294815
0.9817 High Similarity NPC473327
0.9816 High Similarity NPC180918
0.9816 High Similarity NPC26230
0.9816 High Similarity NPC60735
0.9755 High Similarity NPC29958
0.9755 High Similarity NPC285197
0.9755 High Similarity NPC136042
0.9755 High Similarity NPC67326
0.9755 High Similarity NPC259896
0.9755 High Similarity NPC156869
0.9755 High Similarity NPC254855
0.9755 High Similarity NPC255157
0.9699 High Similarity NPC173837
0.9697 High Similarity NPC198199
0.9695 High Similarity NPC33054
0.9695 High Similarity NPC203259
0.9695 High Similarity NPC471748
0.9695 High Similarity NPC471725
0.9695 High Similarity NPC155877
0.9695 High Similarity NPC134532
0.9695 High Similarity NPC176740
0.9693 High Similarity NPC86008
0.9645 High Similarity NPC295625
0.9645 High Similarity NPC470719
0.9645 High Similarity NPC473554
0.9643 High Similarity NPC470718
0.9641 High Similarity NPC110941
0.9641 High Similarity NPC470443
0.9641 High Similarity NPC126784
0.9641 High Similarity NPC473682
0.9641 High Similarity NPC473571
0.9641 High Similarity NPC241423
0.9641 High Similarity NPC470444
0.9639 High Similarity NPC8573
0.9639 High Similarity NPC473862
0.9639 High Similarity NPC471669
0.9639 High Similarity NPC89127
0.9634 High Similarity NPC67105
0.9634 High Similarity NPC95866
0.9632 High Similarity NPC275454
0.9586 High Similarity NPC223860
0.9586 High Similarity NPC470451
0.9586 High Similarity NPC470713
0.9586 High Similarity NPC470717
0.9586 High Similarity NPC460984
0.9586 High Similarity NPC25946
0.9586 High Similarity NPC470720
0.9586 High Similarity NPC275977
0.9586 High Similarity NPC470455
0.9586 High Similarity NPC21359
0.9586 High Similarity NPC249560
0.9581 High Similarity NPC120952
0.9578 High Similarity NPC253685
0.9573 High Similarity NPC120099
0.9573 High Similarity NPC105283
0.9573 High Similarity NPC195257
0.9573 High Similarity NPC227508
0.9573 High Similarity NPC225434
0.9573 High Similarity NPC219904
0.9573 High Similarity NPC209296
0.9573 High Similarity NPC203050
0.9573 High Similarity NPC223747
0.9571 High Similarity NPC308404
0.9571 High Similarity NPC197285
0.9571 High Similarity NPC179950
0.9571 High Similarity NPC274618
0.9571 High Similarity NPC145038
0.9571 High Similarity NPC88789
0.9571 High Similarity NPC118284
0.9571 High Similarity NPC281131
0.9571 High Similarity NPC8856
0.9571 High Similarity NPC56077
0.9571 High Similarity NPC276222
0.9571 High Similarity NPC21100
0.9571 High Similarity NPC253662
0.9529 High Similarity NPC33083
0.9527 High Similarity NPC162394
0.9527 High Similarity NPC470449
0.9527 High Similarity NPC470447
0.9527 High Similarity NPC241781
0.9527 High Similarity NPC470446
0.9527 High Similarity NPC156785
0.9527 High Similarity NPC473072
0.9527 High Similarity NPC470445
0.9521 High Similarity NPC470949
0.9521 High Similarity NPC169733
0.9521 High Similarity NPC255799
0.9521 High Similarity NPC65563
0.9515 High Similarity NPC79056
0.9515 High Similarity NPC105095
0.9515 High Similarity NPC44328
0.9515 High Similarity NPC206123
0.9515 High Similarity NPC177731
0.9512 High Similarity NPC127546
0.9512 High Similarity NPC173637
0.9512 High Similarity NPC265530
0.9512 High Similarity NPC325555
0.9512 High Similarity NPC84362
0.9512 High Similarity NPC223424
0.9512 High Similarity NPC52550
0.9512 High Similarity NPC226304
0.9512 High Similarity NPC160156
0.9512 High Similarity NPC92565
0.9512 High Similarity NPC317489
0.9509 High Similarity NPC277205
0.9509 High Similarity NPC55786
0.9509 High Similarity NPC289667
0.9509 High Similarity NPC76831
0.9509 High Similarity NPC19388
0.9509 High Similarity NPC292929
0.9509 High Similarity NPC240431
0.9474 High Similarity NPC30011
0.9474 High Similarity NPC97817
0.9474 High Similarity NPC72554
0.9471 High Similarity NPC148710
0.9467 High Similarity NPC473071
0.9467 High Similarity NPC473073
0.9461 High Similarity NPC294629
0.9458 High Similarity NPC3583
0.9458 High Similarity NPC259152
0.9458 High Similarity NPC153755
0.9455 High Similarity NPC270578
0.9455 High Similarity NPC52382
0.9455 High Similarity NPC43587
0.9455 High Similarity NPC293629
0.9451 High Similarity NPC203145
0.9451 High Similarity NPC477613
0.9451 High Similarity NPC32641
0.9451 High Similarity NPC12013
0.9451 High Similarity NPC113968
0.9451 High Similarity NPC476470
0.9451 High Similarity NPC221342
0.9451 High Similarity NPC142142
0.9451 High Similarity NPC277174
0.9451 High Similarity NPC256188
0.9451 High Similarity NPC135599
0.9451 High Similarity NPC115674
0.9451 High Similarity NPC210073
0.9451 High Similarity NPC11432
0.9451 High Similarity NPC73855
0.9451 High Similarity NPC328940
0.9451 High Similarity NPC186816
0.9451 High Similarity NPC189564
0.9448 High Similarity NPC191306
0.9448 High Similarity NPC270335
0.9415 High Similarity NPC104910
0.9415 High Similarity NPC474093
0.9401 High Similarity NPC21666
0.9401 High Similarity NPC24043
0.9401 High Similarity NPC208668
0.9401 High Similarity NPC204693
0.9401 High Similarity NPC169977
0.9401 High Similarity NPC4390
0.9401 High Similarity NPC101026
0.9401 High Similarity NPC42773
0.9401 High Similarity NPC45522
0.9401 High Similarity NPC25724
0.9398 High Similarity NPC244776
0.9398 High Similarity NPC20505
0.9398 High Similarity NPC235260
0.9398 High Similarity NPC245014
0.9398 High Similarity NPC218488
0.9398 High Similarity NPC155763
0.9398 High Similarity NPC84265
0.9398 High Similarity NPC282987
0.9398 High Similarity NPC116864
0.9398 High Similarity NPC51326
0.9398 High Similarity NPC231194
0.939 High Similarity NPC475366
0.939 High Similarity NPC22832
0.939 High Similarity NPC284277
0.939 High Similarity NPC15358
0.939 High Similarity NPC287889
0.939 High Similarity NPC311830
0.939 High Similarity NPC135358
0.939 High Similarity NPC475497
0.9387 High Similarity NPC77660
0.9387 High Similarity NPC189142
0.936 High Similarity NPC475179
0.936 High Similarity NPC64755
0.9349 High Similarity NPC113836
0.9349 High Similarity NPC37668
0.9349 High Similarity NPC217520
0.9349 High Similarity NPC139571
0.9349 High Similarity NPC253521
0.9349 High Similarity NPC477895
0.9345 High Similarity NPC237435

  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 NPC219043 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
0.9817 High Similarity NPD7808 Phase 3
0.9756 High Similarity NPD7251 Discontinued
0.9695 High Similarity NPD6797 Phase 2
0.9634 High Similarity NPD7472 Approved
0.9573 High Similarity NPD7054 Approved
0.9515 High Similarity NPD7074 Phase 3
0.9345 High Similarity NPD4338 Clinical (unspecified phase)
0.9222 High Similarity NPD7804 Clinical (unspecified phase)
0.9048 High Similarity NPD3818 Discontinued
0.9042 High Similarity NPD6168 Clinical (unspecified phase)
0.9042 High Similarity NPD6166 Phase 2
0.9042 High Similarity NPD6167 Clinical (unspecified phase)
0.8909 High Similarity NPD4381 Clinical (unspecified phase)
0.8675 High Similarity NPD3817 Phase 2
0.8667 High Similarity NPD1934 Approved
0.8563 High Similarity NPD7993 Clinical (unspecified phase)
0.8528 High Similarity NPD1512 Approved
0.8512 High Similarity NPD3882 Suspended
0.8503 High Similarity NPD2393 Clinical (unspecified phase)
0.8503 High Similarity NPD2801 Approved
0.8405 Intermediate Similarity NPD1511 Approved
0.8353 Intermediate Similarity NPD7075 Discontinued
0.8323 Intermediate Similarity NPD4380 Phase 2
0.8294 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD5402 Approved
0.8176 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8144 Intermediate Similarity NPD5403 Approved
0.8118 Intermediate Similarity NPD6801 Discontinued
0.8101 Intermediate Similarity NPD6559 Discontinued
0.8098 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD5401 Approved
0.8024 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD8313 Approved
0.8011 Intermediate Similarity NPD8312 Approved
0.7988 Intermediate Similarity NPD1653 Approved
0.7978 Intermediate Similarity NPD3751 Discontinued
0.7964 Intermediate Similarity NPD6799 Approved
0.7955 Intermediate Similarity NPD3787 Discontinued
0.7943 Intermediate Similarity NPD5494 Approved
0.7927 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7927 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD7685 Pre-registration
0.7879 Intermediate Similarity NPD1549 Phase 2
0.7877 Intermediate Similarity NPD7228 Approved
0.7861 Intermediate Similarity NPD1465 Phase 2
0.7861 Intermediate Similarity NPD7819 Suspended
0.7797 Intermediate Similarity NPD6959 Discontinued
0.7759 Intermediate Similarity NPD8455 Phase 2
0.7735 Intermediate Similarity NPD5844 Phase 1
0.773 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD7473 Discontinued
0.7709 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD1510 Phase 2
0.7688 Intermediate Similarity NPD6599 Discontinued
0.7665 Intermediate Similarity NPD8151 Discontinued
0.7654 Intermediate Similarity NPD6232 Discontinued
0.7651 Intermediate Similarity NPD2796 Approved
0.7644 Intermediate Similarity NPD7411 Suspended
0.7616 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD7266 Discontinued
0.7602 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD7199 Phase 2
0.759 Intermediate Similarity NPD7697 Approved
0.759 Intermediate Similarity NPD7698 Approved
0.759 Intermediate Similarity NPD7696 Phase 3
0.759 Intermediate Similarity NPD7435 Discontinued
0.7584 Intermediate Similarity NPD919 Approved
0.7569 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD1613 Approved
0.7529 Intermediate Similarity NPD6190 Approved
0.7526 Intermediate Similarity NPD6779 Approved
0.7526 Intermediate Similarity NPD6778 Approved
0.7526 Intermediate Similarity NPD6776 Approved
0.7526 Intermediate Similarity NPD6782 Approved
0.7526 Intermediate Similarity NPD6777 Approved
0.7526 Intermediate Similarity NPD6781 Approved
0.7526 Intermediate Similarity NPD6780 Approved
0.7525 Intermediate Similarity NPD7701 Phase 2
0.7514 Intermediate Similarity NPD7240 Approved
0.75 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7783 Phase 2
0.75 Intermediate Similarity NPD1247 Approved
0.7486 Intermediate Similarity NPD6234 Discontinued
0.7475 Intermediate Similarity NPD7584 Approved
0.7462 Intermediate Similarity NPD8320 Phase 1
0.7462 Intermediate Similarity NPD8319 Approved
0.7462 Intermediate Similarity NPD7870 Phase 2
0.7462 Intermediate Similarity NPD7871 Phase 2
0.7461 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD7874 Approved
0.745 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7699 Phase 2
0.7423 Intermediate Similarity NPD7700 Phase 2
0.7418 Intermediate Similarity NPD3926 Phase 2
0.7401 Intermediate Similarity NPD37 Approved
0.7374 Intermediate Similarity NPD4966 Approved
0.7374 Intermediate Similarity NPD4967 Phase 2
0.7374 Intermediate Similarity NPD4965 Approved
0.7374 Intermediate Similarity NPD7768 Phase 2
0.7368 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD3750 Approved
0.7353 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD1240 Approved
0.7349 Intermediate Similarity NPD943 Approved
0.7341 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD7801 Approved
0.7317 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD1933 Approved
0.7273 Intermediate Similarity NPD3027 Phase 3
0.7268 Intermediate Similarity NPD6534 Approved
0.7268 Intermediate Similarity NPD6535 Approved
0.7262 Intermediate Similarity NPD1607 Approved
0.7256 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD3749 Approved
0.7235 Intermediate Similarity NPD1551 Phase 2
0.7229 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD8434 Phase 2
0.7225 Intermediate Similarity NPD8150 Discontinued
0.7202 Intermediate Similarity NPD230 Phase 1
0.7189 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD6823 Phase 2
0.7176 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD4628 Phase 3
0.715 Intermediate Similarity NPD7680 Approved
0.7121 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD447 Suspended
0.7095 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD7585 Approved
0.7085 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD3748 Approved
0.7044 Intermediate Similarity NPD7583 Approved
0.7039 Intermediate Similarity NPD7458 Discontinued
0.7035 Intermediate Similarity NPD2935 Discontinued
0.7028 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6674 Discontinued
0.7006 Intermediate Similarity NPD2532 Approved
0.7006 Intermediate Similarity NPD2533 Approved
0.7006 Intermediate Similarity NPD2534 Approved
0.7006 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.6994 Remote Similarity NPD1091 Approved
0.6936 Remote Similarity NPD6099 Approved
0.6936 Remote Similarity NPD6100 Approved
0.6927 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6927 Remote Similarity NPD920 Approved
0.6923 Remote Similarity NPD6798 Discontinued
0.6923 Remote Similarity NPD6844 Discontinued
0.6919 Remote Similarity NPD4360 Phase 2
0.6919 Remote Similarity NPD4363 Phase 3
0.6914 Remote Similarity NPD2800 Approved
0.6911 Remote Similarity NPD5953 Discontinued
0.691 Remote Similarity NPD642 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6832 Phase 2
0.6901 Remote Similarity NPD6355 Discontinued
0.6895 Remote Similarity NPD7286 Phase 2
0.6893 Remote Similarity NPD643 Clinical (unspecified phase)
0.6882 Remote Similarity NPD6233 Phase 2
0.6879 Remote Similarity NPD7033 Discontinued
0.6869 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6869 Remote Similarity NPD6212 Phase 3
0.6869 Remote Similarity NPD6213 Phase 3
0.686 Remote Similarity NPD6651 Approved
0.6854 Remote Similarity NPD7390 Discontinued
0.6851 Remote Similarity NPD3226 Approved
0.6848 Remote Similarity NPD5353 Approved
0.6845 Remote Similarity NPD8127 Discontinued
0.6845 Remote Similarity NPD9494 Approved
0.6826 Remote Similarity NPD1203 Approved
0.6824 Remote Similarity NPD2313 Discontinued
0.6818 Remote Similarity NPD1652 Phase 2
0.6818 Remote Similarity NPD1243 Approved
0.681 Remote Similarity NPD7930 Approved
0.6807 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6805 Remote Similarity NPD4908 Phase 1
0.6788 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6786 Remote Similarity NPD2798 Approved
0.678 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6776 Remote Similarity NPD7907 Approved
0.6758 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6754 Remote Similarity NPD2163 Approved
0.6751 Remote Similarity NPD6841 Approved
0.6751 Remote Similarity NPD6843 Phase 3
0.6751 Remote Similarity NPD6842 Approved
0.6748 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6748 Remote Similarity NPD1548 Phase 1
0.6725 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6705 Remote Similarity NPD2344 Approved
0.6705 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6705 Remote Similarity NPD2346 Discontinued
0.6705 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6705 Remote Similarity NPD5124 Phase 1
0.6697 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6697 Remote Similarity NPD8059 Phase 3
0.6687 Remote Similarity NPD1610 Phase 2
0.6686 Remote Similarity NPD2799 Discontinued
0.6685 Remote Similarity NPD6385 Approved
0.6685 Remote Similarity NPD6386 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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