Structure

Physi-Chem Properties

Molecular Weight:  522.14
Volume:  482.616
LogP:  0.535
LogD:  0.98
LogS:  -3.977
# Rotatable Bonds:  7
TPSA:  197.74
# H-Bond Aceptor:  13
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.244
Synthetic Accessibility Score:  4.145
Fsp3:  0.375
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.278
MDCK Permeability:  2.513688559702132e-05
Pgp-inhibitor:  0.1
Pgp-substrate:  0.94
Human Intestinal Absorption (HIA):  0.444
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.22

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.099
Plasma Protein Binding (PPB):  75.92240905761719%
Volume Distribution (VD):  0.678
Pgp-substrate:  29.54513168334961%

ADMET: Metabolism

CYP1A2-inhibitor:  0.044
CYP1A2-substrate:  0.95
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.094
CYP2C9-inhibitor:  0.016
CYP2C9-substrate:  0.246
CYP2D6-inhibitor:  0.081
CYP2D6-substrate:  0.199
CYP3A4-inhibitor:  0.089
CYP3A4-substrate:  0.033

ADMET: Excretion

Clearance (CL):  5.293
Half-life (T1/2):  0.857

ADMET: Toxicity

hERG Blockers:  0.37
Human Hepatotoxicity (H-HT):  0.221
Drug-inuced Liver Injury (DILI):  0.413
AMES Toxicity:  0.284
Rat Oral Acute Toxicity:  0.058
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.64
Carcinogencity:  0.028
Eye Corrosion:  0.003
Eye Irritation:  0.031
Respiratory Toxicity:  0.016

Download Data

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

  Natural Product: NPC224462

Natural Product ID:  NPC224462
Common Name*:   Iridin
IUPAC Name:   5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:   Iridin
Standard InCHIKey:  LNQCUTNLHUQZLR-OZJWLQQPSA-N
Standard InCHI:  InChI=1S/C24H26O13/c1-32-13-5-9(4-11(26)22(13)33-2)10-8-35-12-6-14(23(34-3)19(29)16(12)17(10)27)36-24-21(31)20(30)18(28)15(7-25)37-24/h4-6,8,15,18,20-21,24-26,28-31H,7H2,1-3H3/t15-,18-,20+,21-,24-/m1/s1
SMILES:  COc1cc(cc(c1OC)O)c1coc2cc(c(c(c2c1=O)O)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL487014
PubChem CID:   5281777
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0000507] Isoflavonoid 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
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[10075762]
NPO1859 Lantana camara Species Verbenaceae Eukaryota aerial parts n.a. n.a. PMID[10869197]
NPO3165 Cochlospermum tinctorium Species Bixaceae Eukaryota n.a. n.a. n.a. PMID[12350157]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. PMID[1812212]
NPO7478 Iris germanica Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19829679]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. root n.a. PMID[21087019]
NPO7528 Belamcanda chinensis Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[21465599]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[22314230]
NPO7478 Iris germanica Species Iridaceae Eukaryota n.a. rhizome n.a. PMID[22388969]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23521110]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[24433009]
NPO7528 Belamcanda chinensis Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[25036154]
NPO7478 Iris germanica Species Iridaceae Eukaryota n.a. rhizome n.a. PMID[25204177]
NPO3165 Cochlospermum tinctorium Species Bixaceae Eukaryota n.a. n.a. n.a. PMID[2553872]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[28032759]
NPO7528 Belamcanda chinensis Species Iridaceae Eukaryota Rhizomes n.a. n.a. PMID[31246464]
NPO1859 Lantana camara Species Verbenaceae Eukaryota leaves n.a. n.a. PMID[9834145]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[9834167]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7478 Iris germanica Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13012 Iris dichotoma Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13012 Iris dichotoma Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7478 Iris germanica Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2781 Iris kumaonensis Species Tarachodidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7528 Belamcanda chinensis Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7478 Iris germanica Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13012 Iris dichotoma Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7528 Belamcanda chinensis Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13012 Iris dichotoma Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2566 0cardiopsaceae Species 0cardiopsaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7528 Belamcanda chinensis Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2781 Iris kumaonensis Species Tarachodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3165 Cochlospermum tinctorium Species Bixaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6516 Aspidosperma megalocarpon Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO942 Perophora namei Species Perophoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3733 Senecio triangularis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5561 Thenea muricata Species Theneidae 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
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Inhibition = 0.0 % PMID[499850]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 90.79 % PMID[499852]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 114.51 % PMID[499852]

☑ 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 NPC224462 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
0.9938 High Similarity NPC307518
0.9938 High Similarity NPC48773
0.9938 High Similarity NPC205076
0.9875 High Similarity NPC105511
0.9812 High Similarity NPC201292
0.9812 High Similarity NPC469931
0.9812 High Similarity NPC45638
0.9812 High Similarity NPC186807
0.9812 High Similarity NPC475942
0.9812 High Similarity NPC183036
0.9812 High Similarity NPC93337
0.9812 High Similarity NPC58053
0.9812 High Similarity NPC105025
0.9812 High Similarity NPC226294
0.9752 High Similarity NPC22195
0.9752 High Similarity NPC471416
0.9752 High Similarity NPC34287
0.9752 High Similarity NPC183357
0.9752 High Similarity NPC21190
0.9752 High Similarity NPC474434
0.9752 High Similarity NPC44558
0.975 High Similarity NPC45618
0.975 High Similarity NPC229729
0.975 High Similarity NPC58716
0.975 High Similarity NPC135345
0.975 High Similarity NPC146792
0.9691 High Similarity NPC476405
0.9691 High Similarity NPC172807
0.9691 High Similarity NPC211594
0.9691 High Similarity NPC117260
0.9691 High Similarity NPC254540
0.9689 High Similarity NPC472383
0.9689 High Similarity NPC229687
0.9689 High Similarity NPC112755
0.9689 High Similarity NPC170675
0.9689 High Similarity NPC95855
0.9689 High Similarity NPC210042
0.9689 High Similarity NPC472381
0.9689 High Similarity NPC471457
0.9688 High Similarity NPC181616
0.9688 High Similarity NPC99957
0.9686 High Similarity NPC284960
0.9686 High Similarity NPC222936
0.9686 High Similarity NPC94777
0.9634 High Similarity NPC257714
0.9632 High Similarity NPC21666
0.9632 High Similarity NPC42773
0.9632 High Similarity NPC51774
0.9632 High Similarity NPC236191
0.9632 High Similarity NPC204693
0.9632 High Similarity NPC169977
0.9632 High Similarity NPC45522
0.9632 High Similarity NPC24043
0.9632 High Similarity NPC101026
0.9632 High Similarity NPC239549
0.963 High Similarity NPC84265
0.963 High Similarity NPC245014
0.963 High Similarity NPC51326
0.963 High Similarity NPC231194
0.963 High Similarity NPC282987
0.9627 High Similarity NPC45400
0.9627 High Similarity NPC93099
0.9625 High Similarity NPC311830
0.9625 High Similarity NPC165720
0.9625 High Similarity NPC22832
0.9623 High Similarity NPC473043
0.9576 High Similarity NPC168584
0.9573 High Similarity NPC472607
0.9573 High Similarity NPC477848
0.9571 High Similarity NPC301683
0.9571 High Similarity NPC3583
0.9571 High Similarity NPC267254
0.9571 High Similarity NPC259152
0.9571 High Similarity NPC475155
0.9571 High Similarity NPC472386
0.9571 High Similarity NPC235575
0.9565 High Similarity NPC236934
0.9565 High Similarity NPC5778
0.9563 High Similarity NPC88023
0.9563 High Similarity NPC19709
0.9563 High Similarity NPC243930
0.9563 High Similarity NPC168822
0.9563 High Similarity NPC309025
0.9563 High Similarity NPC191306
0.9563 High Similarity NPC88043
0.9563 High Similarity NPC270335
0.9515 High Similarity NPC198324
0.9515 High Similarity NPC472991
0.9515 High Similarity NPC472992
0.9515 High Similarity NPC472385
0.9515 High Similarity NPC233994
0.9515 High Similarity NPC211532
0.9515 High Similarity NPC169733
0.9509 High Similarity NPC206123
0.9509 High Similarity NPC212748
0.9506 High Similarity NPC226304
0.9506 High Similarity NPC477502
0.9506 High Similarity NPC116745
0.9506 High Similarity NPC265530
0.9506 High Similarity NPC325555
0.95 High Similarity NPC300537
0.95 High Similarity NPC77660
0.95 High Similarity NPC189142
0.95 High Similarity NPC127782
0.9497 High Similarity NPC110349
0.9458 High Similarity NPC476620
0.9458 High Similarity NPC476618
0.9458 High Similarity NPC472387
0.9458 High Similarity NPC476619
0.9458 High Similarity NPC476622
0.9458 High Similarity NPC476621
0.9458 High Similarity NPC476623
0.9455 High Similarity NPC142996
0.9455 High Similarity NPC264735
0.9455 High Similarity NPC102028
0.9455 High Similarity NPC49344
0.9455 High Similarity NPC43211
0.9455 High Similarity NPC101191
0.9455 High Similarity NPC210094
0.9455 High Similarity NPC237435
0.9455 High Similarity NPC135277
0.9455 High Similarity NPC115760
0.9451 High Similarity NPC156977
0.9451 High Similarity NPC256760
0.9448 High Similarity NPC120099
0.9448 High Similarity NPC203050
0.9448 High Similarity NPC195257
0.9448 High Similarity NPC219904
0.9448 High Similarity NPC471287
0.9448 High Similarity NPC225434
0.9448 High Similarity NPC223747
0.9448 High Similarity NPC209296
0.9444 High Similarity NPC210073
0.9444 High Similarity NPC197285
0.9444 High Similarity NPC21100
0.9444 High Similarity NPC328940
0.9444 High Similarity NPC135599
0.9444 High Similarity NPC113968
0.9444 High Similarity NPC277174
0.9444 High Similarity NPC73855
0.9444 High Similarity NPC115674
0.9441 High Similarity NPC127415
0.9441 High Similarity NPC29830
0.9437 High Similarity NPC182045
0.9405 High Similarity NPC36138
0.9401 High Similarity NPC473682
0.9401 High Similarity NPC470444
0.9401 High Similarity NPC470443
0.9401 High Similarity NPC110941
0.9401 High Similarity NPC241423
0.9401 High Similarity NPC473571
0.9401 High Similarity NPC126784
0.9398 High Similarity NPC470949
0.9398 High Similarity NPC472380
0.9398 High Similarity NPC472382
0.9398 High Similarity NPC472384
0.9398 High Similarity NPC268533
0.9398 High Similarity NPC8573
0.9398 High Similarity NPC65563
0.9394 High Similarity NPC175230
0.9394 High Similarity NPC4390
0.9394 High Similarity NPC172033
0.9394 High Similarity NPC88560
0.9394 High Similarity NPC208668
0.9394 High Similarity NPC472993
0.939 High Similarity NPC150767
0.939 High Similarity NPC79056
0.939 High Similarity NPC105095
0.939 High Similarity NPC293004
0.939 High Similarity NPC177731
0.939 High Similarity NPC78734
0.939 High Similarity NPC204937
0.939 High Similarity NPC52353
0.939 High Similarity NPC149011
0.939 High Similarity NPC44328
0.9387 High Similarity NPC173637
0.9387 High Similarity NPC84362
0.9387 High Similarity NPC471288
0.9387 High Similarity NPC223424
0.9387 High Similarity NPC243877
0.9387 High Similarity NPC127546
0.9387 High Similarity NPC317489
0.9387 High Similarity NPC52550
0.9383 High Similarity NPC277205
0.9383 High Similarity NPC19388
0.9383 High Similarity NPC55786
0.9383 High Similarity NPC240431
0.9349 High Similarity NPC470416
0.9349 High Similarity NPC148710
0.9345 High Similarity NPC473071
0.9345 High Similarity NPC473073
0.9341 High Similarity NPC475261
0.9333 High Similarity NPC190003
0.9333 High Similarity NPC153755
0.9333 High Similarity NPC175107
0.9333 High Similarity NPC261254
0.9329 High Similarity NPC293629
0.9329 High Similarity NPC270578
0.9329 High Similarity NPC43587
0.9329 High Similarity NPC61791

  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 NPC224462 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
0.9506 High Similarity NPD3818 Discontinued
0.9455 High Similarity NPD4338 Clinical (unspecified phase)
0.9448 High Similarity NPD7054 Approved
0.939 High Similarity NPD7472 Approved
0.939 High Similarity NPD7074 Phase 3
0.925 High Similarity NPD4381 Clinical (unspecified phase)
0.9217 High Similarity NPD6797 Phase 2
0.9162 High Similarity NPD7251 Discontinued
0.9107 High Similarity NPD7808 Phase 3
0.9062 High Similarity NPD2801 Approved
0.9 High Similarity NPD1934 Approved
0.8916 High Similarity NPD6167 Clinical (unspecified phase)
0.8916 High Similarity NPD6166 Phase 2
0.8916 High Similarity NPD6168 Clinical (unspecified phase)
0.8834 High Similarity NPD4868 Clinical (unspecified phase)
0.8827 High Similarity NPD2393 Clinical (unspecified phase)
0.8757 High Similarity NPD7804 Clinical (unspecified phase)
0.8642 High Similarity NPD4380 Phase 2
0.8606 High Similarity NPD3882 Suspended
0.8563 High Similarity NPD5494 Approved
0.8545 High Similarity NPD3817 Phase 2
0.85 High Similarity NPD1511 Approved
0.8497 Intermediate Similarity NPD6559 Discontinued
0.8439 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD5402 Approved
0.8405 Intermediate Similarity NPD1653 Approved
0.8395 Intermediate Similarity NPD1512 Approved
0.8333 Intermediate Similarity NPD7075 Discontinued
0.8324 Intermediate Similarity NPD5844 Phase 1
0.8263 Intermediate Similarity NPD1465 Phase 2
0.8204 Intermediate Similarity NPD6801 Discontinued
0.8187 Intermediate Similarity NPD1549 Phase 2
0.8177 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.811 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD7685 Pre-registration
0.8066 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD2796 Approved
0.8057 Intermediate Similarity NPD7228 Approved
0.8047 Intermediate Similarity NPD7819 Suspended
0.8036 Intermediate Similarity NPD7411 Suspended
0.8035 Intermediate Similarity NPD6232 Discontinued
0.8012 Intermediate Similarity NPD5403 Approved
0.8012 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7473 Discontinued
0.8 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1510 Phase 2
0.7977 Intermediate Similarity NPD6959 Discontinued
0.7965 Intermediate Similarity NPD6234 Discontinued
0.7955 Intermediate Similarity NPD3751 Discontinued
0.7939 Intermediate Similarity NPD6799 Approved
0.7901 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD5401 Approved
0.7889 Intermediate Similarity NPD8312 Approved
0.7889 Intermediate Similarity NPD8313 Approved
0.7882 Intermediate Similarity NPD37 Approved
0.7874 Intermediate Similarity NPD7199 Phase 2
0.7874 Intermediate Similarity NPD1247 Approved
0.7872 Intermediate Similarity NPD6778 Approved
0.7872 Intermediate Similarity NPD6779 Approved
0.7872 Intermediate Similarity NPD6781 Approved
0.7872 Intermediate Similarity NPD6782 Approved
0.7872 Intermediate Similarity NPD6780 Approved
0.7872 Intermediate Similarity NPD6777 Approved
0.7872 Intermediate Similarity NPD6776 Approved
0.7849 Intermediate Similarity NPD4965 Approved
0.7849 Intermediate Similarity NPD4966 Approved
0.7849 Intermediate Similarity NPD4967 Phase 2
0.7829 Intermediate Similarity NPD3787 Discontinued
0.7765 Intermediate Similarity NPD6599 Discontinued
0.7758 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD1240 Approved
0.775 Intermediate Similarity NPD943 Approved
0.775 Intermediate Similarity NPD1613 Approved
0.7749 Intermediate Similarity NPD7435 Discontinued
0.774 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7732 Intermediate Similarity NPD8151 Discontinued
0.772 Intermediate Similarity NPD7584 Approved
0.7702 Intermediate Similarity NPD230 Phase 1
0.7684 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD3926 Phase 2
0.7683 Intermediate Similarity NPD7266 Discontinued
0.7657 Intermediate Similarity NPD919 Approved
0.7656 Intermediate Similarity NPD7698 Approved
0.7656 Intermediate Similarity NPD7697 Approved
0.7656 Intermediate Similarity NPD7696 Phase 3
0.7654 Intermediate Similarity NPD1607 Approved
0.7651 Intermediate Similarity NPD3750 Approved
0.7636 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD2935 Discontinued
0.7619 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7617 Intermediate Similarity NPD7871 Phase 2
0.7617 Intermediate Similarity NPD7870 Phase 2
0.7606 Intermediate Similarity NPD6534 Approved
0.7606 Intermediate Similarity NPD6535 Approved
0.7605 Intermediate Similarity NPD6190 Approved
0.7604 Intermediate Similarity NPD6823 Phase 2
0.76 Intermediate Similarity NPD3749 Approved
0.7593 Intermediate Similarity NPD1933 Approved
0.759 Intermediate Similarity NPD7701 Phase 2
0.7582 Intermediate Similarity NPD7240 Approved
0.7563 Intermediate Similarity NPD7783 Phase 2
0.7563 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD3027 Phase 3
0.7547 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD4628 Phase 3
0.7543 Intermediate Similarity NPD7768 Phase 2
0.7513 Intermediate Similarity NPD7874 Approved
0.7513 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7699 Phase 2
0.7487 Intermediate Similarity NPD7700 Phase 2
0.7485 Intermediate Similarity NPD447 Suspended
0.7475 Intermediate Similarity NPD7801 Approved
0.7471 Intermediate Similarity NPD2532 Approved
0.7471 Intermediate Similarity NPD2533 Approved
0.7471 Intermediate Similarity NPD2534 Approved
0.7429 Intermediate Similarity NPD8455 Phase 2
0.741 Intermediate Similarity NPD1551 Phase 2
0.7409 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD920 Approved
0.7381 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD2800 Approved
0.7371 Intermediate Similarity NPD6844 Discontinued
0.7368 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6212 Phase 3
0.7368 Intermediate Similarity NPD6213 Phase 3
0.7349 Intermediate Similarity NPD3748 Approved
0.7344 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD5953 Discontinued
0.7323 Intermediate Similarity NPD7585 Approved
0.7301 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD3226 Approved
0.7287 Intermediate Similarity NPD8150 Discontinued
0.7287 Intermediate Similarity NPD8434 Phase 2
0.7278 Intermediate Similarity NPD6674 Discontinued
0.7278 Intermediate Similarity NPD1243 Approved
0.7273 Intermediate Similarity NPD7583 Approved
0.7268 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD7286 Phase 2
0.7222 Intermediate Similarity NPD9494 Approved
0.7202 Intermediate Similarity NPD6099 Approved
0.7202 Intermediate Similarity NPD6100 Approved
0.72 Intermediate Similarity NPD7458 Discontinued
0.7195 Intermediate Similarity NPD2313 Discontinued
0.7191 Intermediate Similarity NPD5353 Approved
0.7172 Intermediate Similarity NPD8320 Phase 1
0.7172 Intermediate Similarity NPD8319 Approved
0.7168 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2346 Discontinued
0.716 Intermediate Similarity NPD2798 Approved
0.716 Intermediate Similarity NPD2344 Approved
0.7151 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD4360 Phase 2
0.715 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD4363 Phase 3
0.7143 Intermediate Similarity NPD7033 Discontinued
0.7143 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2799 Discontinued
0.7135 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6651 Approved
0.7121 Intermediate Similarity NPD7680 Approved
0.711 Intermediate Similarity NPD7390 Discontinued
0.7104 Intermediate Similarity NPD5242 Approved
0.7081 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD7549 Discontinued
0.7073 Intermediate Similarity NPD4908 Phase 1
0.7073 Intermediate Similarity NPD6832 Phase 2
0.7069 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD6842 Approved
0.7068 Intermediate Similarity NPD6843 Phase 3
0.7068 Intermediate Similarity NPD6841 Approved
0.7063 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1091 Approved
0.705 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD5710 Approved
0.7049 Intermediate Similarity NPD5711 Approved
0.7019 Intermediate Similarity NPD9269 Phase 2
0.7006 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.6995 Remote Similarity NPD8127 Discontinued
0.6994 Remote Similarity NPD1203 Approved
0.6994 Remote Similarity NPD2309 Approved
0.6988 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6985 Remote Similarity NPD5006 Approved
0.6985 Remote Similarity NPD5005 Approved
0.6981 Remote Similarity NPD8059 Phase 3
0.6981 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6977 Remote Similarity NPD1652 Phase 2
0.6973 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6964 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6964 Remote Similarity NPD5124 Phase 1

  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