Structure

Physi-Chem Properties

Molecular Weight:  420.14
Volume:  406.76
LogP:  1.254
LogD:  1.61
LogS:  -2.119
# Rotatable Bonds:  6
TPSA:  149.07
# H-Bond Aceptor:  9
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.366
Synthetic Accessibility Score:  3.744
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.233
MDCK Permeability:  7.747882591502275e-06
Pgp-inhibitor:  0.004
Pgp-substrate:  0.795
Human Intestinal Absorption (HIA):  0.704
20% Bioavailability (F20%):  0.082
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.135
Plasma Protein Binding (PPB):  98.28377532958984%
Volume Distribution (VD):  0.518
Pgp-substrate:  2.5118372440338135%

ADMET: Metabolism

CYP1A2-inhibitor:  0.297
CYP1A2-substrate:  0.102
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.113
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.55
CYP2D6-inhibitor:  0.06
CYP2D6-substrate:  0.76
CYP3A4-inhibitor:  0.088
CYP3A4-substrate:  0.051

ADMET: Excretion

Clearance (CL):  10.259
Half-life (T1/2):  0.874

ADMET: Toxicity

hERG Blockers:  0.287
Human Hepatotoxicity (H-HT):  0.282
Drug-inuced Liver Injury (DILI):  0.038
AMES Toxicity:  0.245
Rat Oral Acute Toxicity:  0.041
Maximum Recommended Daily Dose:  0.025
Skin Sensitization:  0.947
Carcinogencity:  0.16
Eye Corrosion:  0.003
Eye Irritation:  0.073
Respiratory Toxicity:  0.178

Download Data

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

  Natural Product: NPC212770

Natural Product ID:  NPC212770
Common Name*:   (2S,3R,4S,5S,6R)-2-[3-Hydroxy-5-[(E)-2-(4-Hydroxy-3-Methoxyphenyl)Ethenyl]Phenoxy]-6-(Hydroxymethyl)Oxane-3,4,5-Triol
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  KLPUXMNQDCUPNO-DXKBKAGUSA-N
Standard InCHI:  InChI=1S/C21H24O9/c1-28-16-8-11(4-5-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1
SMILES:  COc1cc(/C=C/c2cc(cc(c2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)ccc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL113339
PubChem CID:   5281716
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000253] Stilbenes
        • [CHEMONTID:0000142] Stilbene 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
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np50070a031]
NPO88 Rheum undulatum Species Polygonaceae Eukaryota rhizome n.a. n.a. PMID[10714491]
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[18636777]
NPO691 Tarchonanthus camphoratus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29244495]
NPO284 Albizia procera Species Fabaceae Eukaryota Bark n.a. n.a. PMID[30520635]
NPO16773 Picea abies Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16773 Picea abies Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19432 Millettia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO88 Rheum undulatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1539 Artemisia giraldii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4421 Penicillium cyclopium Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5981 Achlys triphylla Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6844 Bulbophyllum protractum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3963 Hortonia floribunda Species Monimiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3255 Lampranthus sociorum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2963 Diospyros glaucifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO284 Albizia procera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4952 Pertusaria amara Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16773 Picea abies Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3415 Perymenium mendezii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4117 Nauclea rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19432 Millettia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7616 Melanargia galathea Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3263 Thea sasanqua n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15597 Calystegia pubescens Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO691 Tarchonanthus camphoratus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29287 Alectoria ochroleuca Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7464 Uruparia lanosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO88 Rheum undulatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO855 Elymnias thryallis Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7770 Lactuca laciniata Species Asteraceae 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
NPT32 Organism Mus musculus Mus musculus IC50 > 100000.0 nM PMID[523568]
NPT32 Organism Mus musculus Mus musculus Inhibition = 5.0 % PMID[523568]

☑ 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 NPC212770 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 NPC98777
0.9924 High Similarity NPC65530
0.9924 High Similarity NPC59324
0.9847 High Similarity NPC203230
0.9847 High Similarity NPC242028
0.9776 High Similarity NPC189115
0.9776 High Similarity NPC475084
0.9776 High Similarity NPC469559
0.9701 High Similarity NPC469661
0.9632 High Similarity NPC473045
0.9632 High Similarity NPC25292
0.9618 High Similarity NPC294166
0.9618 High Similarity NPC115022
0.9618 High Similarity NPC49074
0.9618 High Similarity NPC132895
0.9562 High Similarity NPC475096
0.9559 High Similarity NPC252169
0.9559 High Similarity NPC473044
0.9549 High Similarity NPC164857
0.9542 High Similarity NPC26080
0.9542 High Similarity NPC85799
0.9542 High Similarity NPC303422
0.9542 High Similarity NPC165686
0.9542 High Similarity NPC162093
0.9493 High Similarity NPC99515
0.9493 High Similarity NPC125755
0.9493 High Similarity NPC190714
0.9478 High Similarity NPC470413
0.9478 High Similarity NPC138738
0.9474 High Similarity NPC470236
0.9474 High Similarity NPC238243
0.9466 High Similarity NPC121376
0.9424 High Similarity NPC227902
0.9424 High Similarity NPC39657
0.942 High Similarity NPC277867
0.942 High Similarity NPC161700
0.9403 High Similarity NPC3293
0.9403 High Similarity NPC40664
0.9403 High Similarity NPC138350
0.9403 High Similarity NPC197723
0.9403 High Similarity NPC165482
0.9398 High Similarity NPC48863
0.9398 High Similarity NPC130496
0.9398 High Similarity NPC188555
0.9398 High Similarity NPC107478
0.9398 High Similarity NPC13745
0.9398 High Similarity NPC170694
0.9398 High Similarity NPC251981
0.9394 High Similarity NPC299144
0.9394 High Similarity NPC470270
0.9357 High Similarity NPC478237
0.9357 High Similarity NPC175976
0.9348 High Similarity NPC76176
0.9348 High Similarity NPC138227
0.9348 High Similarity NPC469313
0.9348 High Similarity NPC168579
0.9343 High Similarity NPC5262
0.9343 High Similarity NPC472714
0.9333 High Similarity NPC124149
0.9333 High Similarity NPC195196
0.9323 High Similarity NPC215833
0.9323 High Similarity NPC69513
0.9318 High Similarity NPC469698
0.9318 High Similarity NPC473412
0.9313 High Similarity NPC218003
0.9313 High Similarity NPC307110
0.9313 High Similarity NPC248355
0.9291 High Similarity NPC286235
0.9291 High Similarity NPC51328
0.9291 High Similarity NPC55158
0.9291 High Similarity NPC106138
0.9286 High Similarity NPC15538
0.9286 High Similarity NPC473480
0.9275 High Similarity NPC37793
0.9259 High Similarity NPC25695
0.9259 High Similarity NPC172818
0.9259 High Similarity NPC199459
0.9259 High Similarity NPC177035
0.9259 High Similarity NPC52277
0.9254 High Similarity NPC187194
0.9248 High Similarity NPC184447
0.9248 High Similarity NPC7903
0.9248 High Similarity NPC16208
0.9248 High Similarity NPC35932
0.9248 High Similarity NPC160991
0.9237 High Similarity NPC302378
0.922 High Similarity NPC130449
0.922 High Similarity NPC248132
0.9209 High Similarity NPC473046
0.9209 High Similarity NPC472712
0.9209 High Similarity NPC118385
0.9209 High Similarity NPC472713
0.9209 High Similarity NPC187774
0.9203 High Similarity NPC157816
0.9197 High Similarity NPC106944
0.9173 High Similarity NPC65942
0.9173 High Similarity NPC472597
0.9173 High Similarity NPC248307
0.9167 High Similarity NPC166040
0.9137 High Similarity NPC46092
0.9137 High Similarity NPC185307
0.9137 High Similarity NPC478239
0.9137 High Similarity NPC81638
0.9137 High Similarity NPC470950
0.913 High Similarity NPC89686
0.913 High Similarity NPC273932
0.913 High Similarity NPC257095
0.913 High Similarity NPC210192
0.9118 High Similarity NPC16435
0.9118 High Similarity NPC306441
0.9118 High Similarity NPC104167
0.9111 High Similarity NPC310854
0.9111 High Similarity NPC476411
0.9111 High Similarity NPC87696
0.9111 High Similarity NPC35731
0.9104 High Similarity NPC253105
0.9104 High Similarity NPC201587
0.9104 High Similarity NPC252833
0.9098 High Similarity NPC472024
0.9098 High Similarity NPC80600
0.9098 High Similarity NPC472338
0.9097 High Similarity NPC21902
0.9091 High Similarity NPC472710
0.9091 High Similarity NPC472709
0.9085 High Similarity NPC280945
0.9078 High Similarity NPC199928
0.9071 High Similarity NPC129417
0.9071 High Similarity NPC283995
0.9071 High Similarity NPC470235
0.9065 High Similarity NPC476356
0.9058 High Similarity NPC210478
0.9044 High Similarity NPC47398
0.9044 High Similarity NPC470356
0.9044 High Similarity NPC94750
0.9044 High Similarity NPC474206
0.9044 High Similarity NPC112246
0.9044 High Similarity NPC121812
0.9044 High Similarity NPC260898
0.9044 High Similarity NPC234333
0.9044 High Similarity NPC61946
0.9044 High Similarity NPC112939
0.9037 High Similarity NPC25821
0.9037 High Similarity NPC6836
0.9034 High Similarity NPC78809
0.9034 High Similarity NPC150442
0.903 High Similarity NPC30043
0.903 High Similarity NPC469613
0.903 High Similarity NPC470095
0.903 High Similarity NPC166168
0.903 High Similarity NPC470096
0.903 High Similarity NPC469625
0.903 High Similarity NPC9912
0.903 High Similarity NPC475067
0.9028 High Similarity NPC473621
0.9023 High Similarity NPC218856
0.9023 High Similarity NPC470633
0.9023 High Similarity NPC210623
0.9023 High Similarity NPC190629
0.9023 High Similarity NPC228769
0.9023 High Similarity NPC273295
0.9023 High Similarity NPC3439
0.9023 High Similarity NPC222004
0.9023 High Similarity NPC86030
0.9023 High Similarity NPC226788
0.9023 High Similarity NPC26653
0.9023 High Similarity NPC470258
0.9023 High Similarity NPC270849
0.9023 High Similarity NPC202582
0.9023 High Similarity NPC5851
0.9023 High Similarity NPC285339
0.9021 High Similarity NPC283839
0.9021 High Similarity NPC90896
0.9008 High Similarity NPC12308
0.9007 High Similarity NPC38041
0.9007 High Similarity NPC22150
0.9007 High Similarity NPC18979
0.9007 High Similarity NPC279298
0.8993 High Similarity NPC472711
0.8993 High Similarity NPC186406
0.8986 High Similarity NPC22517
0.8986 High Similarity NPC100389
0.8986 High Similarity NPC292487
0.8978 High Similarity NPC302701
0.8978 High Similarity NPC227503
0.8978 High Similarity NPC269091
0.8978 High Similarity NPC474639
0.8978 High Similarity NPC230734
0.8971 High Similarity NPC470881
0.8966 High Similarity NPC169404
0.8966 High Similarity NPC53587
0.8966 High Similarity NPC176186
0.8963 High Similarity NPC470752
0.8955 High Similarity NPC469612
0.8955 High Similarity NPC469614
0.8951 High Similarity NPC270751
0.8951 High Similarity NPC93924
0.8947 High Similarity NPC72529
0.8944 High Similarity NPC112861
0.8944 High Similarity NPC476865
0.8936 High Similarity NPC292443

  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 NPC212770 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
0.8881 High Similarity NPD3027 Phase 3
0.8824 High Similarity NPD1613 Approved
0.8824 High Similarity NPD1612 Clinical (unspecified phase)
0.8759 High Similarity NPD1653 Approved
0.8529 High Similarity NPD1529 Clinical (unspecified phase)
0.8456 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD7266 Discontinued
0.8291 Intermediate Similarity NPD7054 Approved
0.8284 Intermediate Similarity NPD1091 Approved
0.8239 Intermediate Similarity NPD7074 Phase 3
0.8239 Intermediate Similarity NPD7472 Approved
0.8113 Intermediate Similarity NPD3818 Discontinued
0.8075 Intermediate Similarity NPD6797 Phase 2
0.8029 Intermediate Similarity NPD2983 Phase 2
0.8029 Intermediate Similarity NPD2982 Phase 2
0.8025 Intermediate Similarity NPD7251 Discontinued
0.8013 Intermediate Similarity NPD6234 Discontinued
0.8 Intermediate Similarity NPD7228 Approved
0.7975 Intermediate Similarity NPD7808 Phase 3
0.7975 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD6674 Discontinued
0.7956 Intermediate Similarity NPD2981 Phase 2
0.7926 Intermediate Similarity NPD1357 Approved
0.7922 Intermediate Similarity NPD1934 Approved
0.7922 Intermediate Similarity NPD37 Approved
0.7885 Intermediate Similarity NPD4967 Phase 2
0.7885 Intermediate Similarity NPD4965 Approved
0.7885 Intermediate Similarity NPD4966 Approved
0.7872 Intermediate Similarity NPD4908 Phase 1
0.7834 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD3018 Phase 2
0.7799 Intermediate Similarity NPD7199 Phase 2
0.7771 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD6166 Phase 2
0.7764 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD1610 Phase 2
0.7754 Intermediate Similarity NPD3705 Approved
0.7721 Intermediate Similarity NPD1548 Phase 1
0.7643 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD2801 Approved
0.7594 Intermediate Similarity NPD228 Approved
0.7593 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD6559 Discontinued
0.7566 Intermediate Similarity NPD5058 Phase 3
0.7552 Intermediate Similarity NPD2861 Phase 2
0.7515 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7240 Approved
0.7485 Intermediate Similarity NPD7685 Pre-registration
0.7484 Intermediate Similarity NPD3817 Phase 2
0.7452 Intermediate Similarity NPD4675 Approved
0.7452 Intermediate Similarity NPD4678 Approved
0.7448 Intermediate Similarity NPD4625 Phase 3
0.7438 Intermediate Similarity NPD3882 Suspended
0.7421 Intermediate Similarity NPD2978 Approved
0.7421 Intermediate Similarity NPD2977 Approved
0.7415 Intermediate Similarity NPD1558 Phase 1
0.7403 Intermediate Similarity NPD1511 Approved
0.7403 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD4749 Approved
0.7391 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6190 Approved
0.7383 Intermediate Similarity NPD4538 Approved
0.7383 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD4536 Approved
0.7372 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD1652 Phase 2
0.7353 Intermediate Similarity NPD5283 Phase 1
0.7321 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD8455 Phase 2
0.7308 Intermediate Similarity NPD1512 Approved
0.7305 Intermediate Similarity NPD5844 Phase 1
0.7297 Intermediate Similarity NPD3620 Phase 2
0.7297 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD7843 Approved
0.7279 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7157 Approved
0.7239 Intermediate Similarity NPD2684 Approved
0.7237 Intermediate Similarity NPD3540 Phase 1
0.7233 Intermediate Similarity NPD4380 Phase 2
0.7219 Intermediate Similarity NPD5588 Approved
0.7219 Intermediate Similarity NPD5960 Phase 3
0.7212 Intermediate Similarity NPD3787 Discontinued
0.7205 Intermediate Similarity NPD1465 Phase 2
0.7181 Intermediate Similarity NPD4060 Phase 1
0.7179 Intermediate Similarity NPD4357 Discontinued
0.7178 Intermediate Similarity NPD7075 Discontinued
0.7176 Intermediate Similarity NPD291 Approved
0.7171 Intermediate Similarity NPD3539 Phase 1
0.717 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD290 Approved
0.7161 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5536 Phase 2
0.7143 Intermediate Similarity NPD3060 Approved
0.7134 Intermediate Similarity NPD4123 Phase 3
0.7133 Intermediate Similarity NPD422 Phase 1
0.7133 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD230 Phase 1
0.7133 Intermediate Similarity NPD5124 Phase 1
0.7126 Intermediate Similarity NPD6841 Approved
0.7126 Intermediate Similarity NPD6843 Phase 3
0.7126 Intermediate Similarity NPD6842 Approved
0.7124 Intermediate Similarity NPD1375 Discontinued
0.7114 Intermediate Similarity NPD6233 Phase 2
0.711 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD1242 Phase 1
0.709 Intermediate Similarity NPD968 Approved
0.7088 Intermediate Similarity NPD7680 Approved
0.707 Intermediate Similarity NPD7213 Phase 3
0.707 Intermediate Similarity NPD7212 Phase 2
0.7063 Intermediate Similarity NPD4005 Discontinued
0.7059 Intermediate Similarity NPD3454 Phase 3
0.7059 Intermediate Similarity NPD3021 Approved
0.7059 Intermediate Similarity NPD3022 Approved
0.7059 Intermediate Similarity NPD556 Approved
0.7055 Intermediate Similarity NPD5402 Approved
0.7052 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD3751 Discontinued
0.7039 Intermediate Similarity NPD7097 Phase 1
0.7032 Intermediate Similarity NPD4237 Approved
0.7032 Intermediate Similarity NPD4236 Phase 3
0.7032 Intermediate Similarity NPD4162 Approved
0.7032 Intermediate Similarity NPD5177 Phase 3
0.7025 Intermediate Similarity NPD7447 Phase 1
0.7013 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD6584 Phase 3
0.7006 Intermediate Similarity NPD6232 Discontinued
0.7 Intermediate Similarity NPD3687 Approved
0.7 Intermediate Similarity NPD3686 Approved
0.7 Intermediate Similarity NPD6671 Approved
0.6994 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6993 Remote Similarity NPD4108 Discontinued
0.6993 Remote Similarity NPD5126 Approved
0.6993 Remote Similarity NPD6516 Phase 2
0.6993 Remote Similarity NPD5125 Phase 3
0.6993 Remote Similarity NPD5846 Approved
0.6988 Remote Similarity NPD5494 Approved
0.6987 Remote Similarity NPD4628 Phase 3
0.6986 Remote Similarity NPD8651 Approved
0.6981 Remote Similarity NPD1940 Clinical (unspecified phase)
0.698 Remote Similarity NPD7095 Approved
0.6968 Remote Similarity NPD1549 Phase 2
0.6943 Remote Similarity NPD2677 Approved
0.6943 Remote Similarity NPD2219 Phase 1
0.6937 Remote Similarity NPD5403 Approved
0.6936 Remote Similarity NPD7549 Discontinued
0.6933 Remote Similarity NPD6801 Discontinued
0.6933 Remote Similarity NPD3384 Approved
0.6933 Remote Similarity NPD3382 Approved
0.6933 Remote Similarity NPD6798 Discontinued
0.6933 Remote Similarity NPD3383 Approved
0.6918 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6913 Remote Similarity NPD3537 Clinical (unspecified phase)
0.6913 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6908 Remote Similarity NPD4340 Discontinued
0.6908 Remote Similarity NPD1933 Approved
0.6908 Remote Similarity NPD5735 Approved
0.6892 Remote Similarity NPD6917 Clinical (unspecified phase)
0.689 Remote Similarity NPD7819 Suspended
0.689 Remote Similarity NPD5773 Approved
0.689 Remote Similarity NPD5772 Approved
0.6887 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6886 Remote Similarity NPD5677 Discontinued
0.6882 Remote Similarity NPD7473 Discontinued
0.6879 Remote Similarity NPD6331 Phase 2
0.6879 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6879 Remote Similarity NPD4110 Phase 3
0.6879 Remote Similarity NPD4535 Phase 3
0.6871 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6863 Remote Similarity NPD6653 Approved
0.6857 Remote Similarity NPD8054 Approved
0.6857 Remote Similarity NPD8053 Approved
0.6855 Remote Similarity NPD6799 Approved
0.6855 Remote Similarity NPD1774 Approved
0.6849 Remote Similarity NPD2231 Phase 2
0.6849 Remote Similarity NPD2235 Phase 2
0.6848 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6846 Remote Similarity NPD9494 Approved
0.6839 Remote Similarity NPD6099 Approved
0.6839 Remote Similarity NPD6100 Approved
0.6832 Remote Similarity NPD2122 Discontinued
0.6829 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6821 Remote Similarity NPD3144 Approved
0.6821 Remote Similarity NPD3145 Approved
0.6818 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6813 Remote Similarity NPD5401 Approved
0.6813 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6803 Remote Similarity NPD3685 Discontinued
0.6803 Remote Similarity NPD6582 Phase 2
0.6803 Remote Similarity NPD6583 Phase 3
0.68 Remote Similarity NPD8313 Approved
0.68 Remote Similarity NPD8312 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