Structure

Physi-Chem Properties

Molecular Weight:  368.13
Volume:  375.116
LogP:  4.646
LogD:  2.876
LogS:  -3.258
# Rotatable Bonds:  4
TPSA:  100.13
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.6
Synthetic Accessibility Score:  2.819
Fsp3:  0.19
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.781
MDCK Permeability:  1.1039288438041694e-05
Pgp-inhibitor:  0.023
Pgp-substrate:  0.663
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.859
30% Bioavailability (F30%):  0.218

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  94.5105209350586%
Volume Distribution (VD):  0.599
Pgp-substrate:  5.53145170211792%

ADMET: Metabolism

CYP1A2-inhibitor:  0.809
CYP1A2-substrate:  0.605
CYP2C19-inhibitor:  0.904
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.866
CYP2C9-substrate:  0.926
CYP2D6-inhibitor:  0.845
CYP2D6-substrate:  0.466
CYP3A4-inhibitor:  0.434
CYP3A4-substrate:  0.104

ADMET: Excretion

Clearance (CL):  7.729
Half-life (T1/2):  0.707

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.443
Drug-inuced Liver Injury (DILI):  0.486
AMES Toxicity:  0.045
Rat Oral Acute Toxicity:  0.32
Maximum Recommended Daily Dose:  0.149
Skin Sensitization:  0.888
Carcinogencity:  0.095
Eye Corrosion:  0.003
Eye Irritation:  0.716
Respiratory Toxicity:  0.182

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

  Natural Product: NPC26051

Natural Product ID:  NPC26051
Common Name*:   7-O-Methylluteone
IUPAC Name:   3-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:  
Standard InCHIKey:  AZPLXDBZIQMMMT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H20O6/c1-11(2)4-6-14-17(26-3)9-18-19(20(14)24)21(25)15(10-27-18)13-7-5-12(22)8-16(13)23/h4-5,7-10,22-24H,6H2,1-3H3
SMILES:  COc1cc2occ(c(=O)c2c(c1CC=C(C)C)O)c1ccc(cc1O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3809337
PubChem CID:   441251
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0001612] Isoflavans
          • [CHEMONTID:0001827] Isoflavanones
            • [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1016/S0031-9422(01)00459-9]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. stem n.a. PMID[12770595]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae 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
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Inhibition = 83.0 % PMID[544261]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 9900.0 nM PMID[544261]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 2.36 n.a. PMID[544262]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 5300.0 nM PMID[544263]

☑ 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 NPC26051 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 NPC52789
1.0 High Similarity NPC55832
1.0 High Similarity NPC268204
0.9926 High Similarity NPC48624
0.9926 High Similarity NPC80962
0.9926 High Similarity NPC253822
0.9926 High Similarity NPC219917
0.9926 High Similarity NPC215311
0.9926 High Similarity NPC101366
0.9926 High Similarity NPC259166
0.9926 High Similarity NPC213659
0.9926 High Similarity NPC326109
0.9926 High Similarity NPC172250
0.9926 High Similarity NPC144118
0.9926 High Similarity NPC204985
0.9853 High Similarity NPC469404
0.9852 High Similarity NPC283429
0.9852 High Similarity NPC295384
0.9783 High Similarity NPC476055
0.9778 High Similarity NPC12175
0.9778 High Similarity NPC279668
0.9778 High Similarity NPC90665
0.9778 High Similarity NPC55162
0.9778 High Similarity NPC309154
0.9778 High Similarity NPC278323
0.971 High Similarity NPC475705
0.971 High Similarity NPC476178
0.971 High Similarity NPC51887
0.971 High Similarity NPC117836
0.9706 High Similarity NPC477956
0.9704 High Similarity NPC7013
0.9704 High Similarity NPC294409
0.9704 High Similarity NPC472419
0.9704 High Similarity NPC303644
0.9704 High Similarity NPC181124
0.9704 High Similarity NPC116632
0.9704 High Similarity NPC209560
0.9704 High Similarity NPC162680
0.964 High Similarity NPC311741
0.964 High Similarity NPC234629
0.9632 High Similarity NPC21350
0.963 High Similarity NPC41461
0.963 High Similarity NPC87545
0.963 High Similarity NPC66349
0.963 High Similarity NPC477243
0.963 High Similarity NPC477244
0.963 High Similarity NPC186838
0.963 High Similarity NPC25287
0.963 High Similarity NPC12165
0.963 High Similarity NPC98115
0.963 High Similarity NPC249606
0.963 High Similarity NPC235428
0.963 High Similarity NPC150399
0.963 High Similarity NPC168105
0.963 High Similarity NPC1486
0.963 High Similarity NPC477242
0.963 High Similarity NPC274109
0.9574 High Similarity NPC266572
0.9565 High Similarity NPC470089
0.9565 High Similarity NPC321980
0.9565 High Similarity NPC470087
0.9565 High Similarity NPC110969
0.9562 High Similarity NPC470211
0.9559 High Similarity NPC317119
0.9559 High Similarity NPC153979
0.9556 High Similarity NPC39426
0.9556 High Similarity NPC234560
0.9556 High Similarity NPC156092
0.9556 High Similarity NPC13575
0.9556 High Similarity NPC131039
0.9507 High Similarity NPC317492
0.9504 High Similarity NPC222298
0.9504 High Similarity NPC51070
0.9504 High Similarity NPC201731
0.9504 High Similarity NPC24673
0.9504 High Similarity NPC97716
0.9504 High Similarity NPC79469
0.9504 High Similarity NPC104406
0.9504 High Similarity NPC237635
0.9496 High Similarity NPC11561
0.9496 High Similarity NPC226636
0.9493 High Similarity NPC159275
0.9493 High Similarity NPC172986
0.9493 High Similarity NPC270883
0.9493 High Similarity NPC261227
0.9493 High Similarity NPC241100
0.9493 High Similarity NPC11056
0.9489 High Similarity NPC243528
0.9489 High Similarity NPC471620
0.9489 High Similarity NPC251681
0.9481 High Similarity NPC103842
0.9481 High Similarity NPC286336
0.9437 High Similarity NPC39195
0.9437 High Similarity NPC6511
0.9437 High Similarity NPC168085
0.9429 High Similarity NPC301751
0.9429 High Similarity NPC149026
0.9429 High Similarity NPC143896
0.9429 High Similarity NPC91560
0.9429 High Similarity NPC245482
0.9429 High Similarity NPC106985
0.9429 High Similarity NPC75049
0.9429 High Similarity NPC18585
0.9429 High Similarity NPC39329
0.9429 High Similarity NPC310130
0.9429 High Similarity NPC169591
0.9429 High Similarity NPC175504
0.9429 High Similarity NPC257097
0.9429 High Similarity NPC68104
0.9429 High Similarity NPC166138
0.9429 High Similarity NPC150408
0.9429 High Similarity NPC164980
0.9429 High Similarity NPC221432
0.9424 High Similarity NPC205006
0.9424 High Similarity NPC147688
0.9424 High Similarity NPC3188
0.9424 High Similarity NPC64908
0.9424 High Similarity NPC282300
0.9424 High Similarity NPC156590
0.9424 High Similarity NPC103362
0.9424 High Similarity NPC118840
0.942 High Similarity NPC53181
0.942 High Similarity NPC220062
0.942 High Similarity NPC217186
0.942 High Similarity NPC18260
0.942 High Similarity NPC216978
0.942 High Similarity NPC472366
0.942 High Similarity NPC55018
0.942 High Similarity NPC303633
0.942 High Similarity NPC78913
0.942 High Similarity NPC96565
0.942 High Similarity NPC301217
0.9416 High Similarity NPC212767
0.9407 High Similarity NPC312318
0.9407 High Similarity NPC159623
0.9407 High Similarity NPC337373
0.9407 High Similarity NPC144051
0.9407 High Similarity NPC82225
0.9407 High Similarity NPC28753
0.9407 High Similarity NPC175098
0.9407 High Similarity NPC56031
0.9407 High Similarity NPC263670
0.9407 High Similarity NPC223354
0.9407 High Similarity NPC188646
0.9407 High Similarity NPC204960
0.9407 High Similarity NPC18877
0.9407 High Similarity NPC192304
0.9407 High Similarity NPC472365
0.9407 High Similarity NPC20560
0.9407 High Similarity NPC139813
0.9407 High Similarity NPC294593
0.9407 High Similarity NPC242294
0.9407 High Similarity NPC27643
0.9371 High Similarity NPC38545
0.9371 High Similarity NPC171916
0.9366 High Similarity NPC110303
0.9366 High Similarity NPC308200
0.9366 High Similarity NPC296998
0.9366 High Similarity NPC473077
0.9366 High Similarity NPC23728
0.9362 High Similarity NPC216538
0.9362 High Similarity NPC319752
0.9362 High Similarity NPC271288
0.9362 High Similarity NPC273538
0.9362 High Similarity NPC224714
0.9362 High Similarity NPC197252
0.9362 High Similarity NPC209040
0.9362 High Similarity NPC473013
0.9362 High Similarity NPC236766
0.9362 High Similarity NPC473015
0.9357 High Similarity NPC182852
0.9357 High Similarity NPC37496
0.9357 High Similarity NPC167624
0.9357 High Similarity NPC40833
0.9357 High Similarity NPC107572
0.9357 High Similarity NPC227579
0.9357 High Similarity NPC76338
0.9357 High Similarity NPC223500
0.9357 High Similarity NPC1089
0.9357 High Similarity NPC265040
0.9357 High Similarity NPC78
0.9357 High Similarity NPC297600
0.9357 High Similarity NPC66515
0.9357 High Similarity NPC76372
0.9357 High Similarity NPC32739
0.9357 High Similarity NPC324436
0.9357 High Similarity NPC161506
0.9357 High Similarity NPC148545
0.9357 High Similarity NPC177354
0.9357 High Similarity NPC64915
0.9357 High Similarity NPC328164
0.9357 High Similarity NPC306829
0.9357 High Similarity NPC194432
0.9357 High Similarity NPC144499
0.9357 High Similarity NPC10937
0.9357 High Similarity NPC148757
0.9357 High Similarity NPC125855
0.9357 High Similarity NPC166482
0.9357 High Similarity NPC296917
0.9357 High Similarity NPC324134

  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 NPC26051 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
0.9556 High Similarity NPD1510 Phase 2
0.9362 High Similarity NPD4378 Clinical (unspecified phase)
0.9259 High Similarity NPD1240 Approved
0.9172 High Similarity NPD4380 Phase 2
0.9124 High Similarity NPD1607 Approved
0.9091 High Similarity NPD7410 Clinical (unspecified phase)
0.9071 High Similarity NPD1549 Phase 2
0.9065 High Similarity NPD2796 Approved
0.9 High Similarity NPD1550 Clinical (unspecified phase)
0.9 High Similarity NPD1552 Clinical (unspecified phase)
0.8859 High Similarity NPD2393 Clinical (unspecified phase)
0.8851 High Similarity NPD7411 Suspended
0.8808 High Similarity NPD7075 Discontinued
0.88 High Similarity NPD8443 Clinical (unspecified phase)
0.8733 High Similarity NPD7819 Suspended
0.8733 High Similarity NPD7096 Clinical (unspecified phase)
0.8667 High Similarity NPD6801 Discontinued
0.8609 High Similarity NPD2801 Approved
0.8562 High Similarity NPD4381 Clinical (unspecified phase)
0.8552 High Similarity NPD1878 Clinical (unspecified phase)
0.8543 High Similarity NPD1934 Approved
0.8531 High Similarity NPD2935 Discontinued
0.8503 High Similarity NPD1511 Approved
0.8503 High Similarity NPD6799 Approved
0.8497 Intermediate Similarity NPD3882 Suspended
0.8497 Intermediate Similarity NPD7768 Phase 2
0.8483 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8471 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8451 Intermediate Similarity NPD6651 Approved
0.8425 Intermediate Similarity NPD3750 Approved
0.8414 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8389 Intermediate Similarity NPD1512 Approved
0.8356 Intermediate Similarity NPD2800 Approved
0.8344 Intermediate Similarity NPD6232 Discontinued
0.8333 Intermediate Similarity NPD920 Approved
0.8333 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD2533 Approved
0.8322 Intermediate Similarity NPD2534 Approved
0.8322 Intermediate Similarity NPD2532 Approved
0.8313 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8302 Intermediate Similarity NPD7473 Discontinued
0.8289 Intermediate Similarity NPD6599 Discontinued
0.828 Intermediate Similarity NPD6959 Discontinued
0.8276 Intermediate Similarity NPD1551 Phase 2
0.825 Intermediate Similarity NPD3818 Discontinued
0.8231 Intermediate Similarity NPD1243 Approved
0.8217 Intermediate Similarity NPD5494 Approved
0.821 Intermediate Similarity NPD5953 Discontinued
0.8207 Intermediate Similarity NPD2799 Discontinued
0.8205 Intermediate Similarity NPD3749 Approved
0.82 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD3817 Phase 2
0.8188 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD943 Approved
0.8169 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8169 Intermediate Similarity NPD2313 Discontinued
0.8143 Intermediate Similarity NPD2798 Approved
0.8125 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD6166 Phase 2
0.811 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD2344 Approved
0.8092 Intermediate Similarity NPD5403 Approved
0.8086 Intermediate Similarity NPD7286 Phase 2
0.8082 Intermediate Similarity NPD3748 Approved
0.8025 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD7054 Approved
0.7962 Intermediate Similarity NPD5402 Approved
0.7961 Intermediate Similarity NPD5401 Approved
0.7939 Intermediate Similarity NPD6559 Discontinued
0.7927 Intermediate Similarity NPD7074 Phase 3
0.7927 Intermediate Similarity NPD7472 Approved
0.7917 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD7390 Discontinued
0.7881 Intermediate Similarity NPD2309 Approved
0.7879 Intermediate Similarity NPD6797 Phase 2
0.7871 Intermediate Similarity NPD3226 Approved
0.7831 Intermediate Similarity NPD7251 Discontinued
0.7826 Intermediate Similarity NPD1247 Approved
0.7817 Intermediate Similarity NPD1203 Approved
0.7815 Intermediate Similarity NPD4628 Phase 3
0.7812 Intermediate Similarity NPD919 Approved
0.7786 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7808 Phase 3
0.7784 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6832 Phase 2
0.7778 Intermediate Similarity NPD4908 Phase 1
0.7758 Intermediate Similarity NPD5844 Phase 1
0.7756 Intermediate Similarity NPD7458 Discontinued
0.7754 Intermediate Similarity NPD1548 Phase 1
0.7748 Intermediate Similarity NPD2654 Approved
0.7742 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD2346 Discontinued
0.773 Intermediate Similarity NPD3972 Approved
0.7718 Intermediate Similarity NPD7033 Discontinued
0.7692 Intermediate Similarity NPD1470 Approved
0.7671 Intermediate Similarity NPD3268 Approved
0.7669 Intermediate Similarity NPD5710 Approved
0.7669 Intermediate Similarity NPD5711 Approved
0.7667 Intermediate Similarity NPD6100 Approved
0.7667 Intermediate Similarity NPD6099 Approved
0.766 Intermediate Similarity NPD1610 Phase 2
0.7644 Intermediate Similarity NPD4360 Phase 2
0.7644 Intermediate Similarity NPD4363 Phase 3
0.7635 Intermediate Similarity NPD230 Phase 1
0.7626 Intermediate Similarity NPD9545 Approved
0.7622 Intermediate Similarity NPD3926 Phase 2
0.7609 Intermediate Similarity NPD9493 Approved
0.7606 Intermediate Similarity NPD9717 Approved
0.76 Intermediate Similarity NPD4361 Phase 2
0.76 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD4308 Phase 3
0.7582 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD7003 Approved
0.7569 Intermediate Similarity NPD1164 Approved
0.7569 Intermediate Similarity NPD2797 Approved
0.756 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD3764 Approved
0.755 Intermediate Similarity NPD5406 Approved
0.755 Intermediate Similarity NPD5408 Approved
0.755 Intermediate Similarity NPD5405 Approved
0.755 Intermediate Similarity NPD5404 Approved
0.7547 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD422 Phase 1
0.7535 Intermediate Similarity NPD1201 Approved
0.7529 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD5124 Phase 1
0.7517 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1729 Discontinued
0.7483 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD1465 Phase 2
0.743 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4288 Approved
0.74 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD1876 Approved
0.7379 Intermediate Similarity NPD3225 Approved
0.7365 Intermediate Similarity NPD3027 Phase 3
0.7365 Intermediate Similarity NPD4625 Phase 3
0.7349 Intermediate Similarity NPD7229 Phase 3
0.7347 Intermediate Similarity NPD9494 Approved
0.7333 Intermediate Similarity NPD4307 Phase 2
0.7329 Intermediate Similarity NPD3266 Approved
0.7329 Intermediate Similarity NPD5890 Approved
0.7329 Intermediate Similarity NPD5889 Approved
0.7329 Intermediate Similarity NPD3267 Approved
0.7325 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD2296 Approved
0.7285 Intermediate Similarity NPD1933 Approved
0.7285 Intermediate Similarity NPD447 Suspended
0.7284 Intermediate Similarity NPD6844 Discontinued
0.7284 Intermediate Similarity NPD37 Approved
0.7283 Intermediate Similarity NPD7584 Approved
0.7278 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1471 Phase 3
0.7266 Intermediate Similarity NPD1241 Discontinued
0.7241 Intermediate Similarity NPD1608 Approved
0.7238 Intermediate Similarity NPD6782 Approved
0.7238 Intermediate Similarity NPD6776 Approved
0.7238 Intermediate Similarity NPD6780 Approved
0.7238 Intermediate Similarity NPD6777 Approved
0.7238 Intermediate Similarity NPD6781 Approved
0.7238 Intermediate Similarity NPD6778 Approved
0.7238 Intermediate Similarity NPD6779 Approved
0.7225 Intermediate Similarity NPD8313 Approved
0.7225 Intermediate Similarity NPD8312 Approved
0.7219 Intermediate Similarity NPD1613 Approved
0.7219 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD4287 Approved
0.7209 Intermediate Similarity NPD6104 Discontinued
0.7203 Intermediate Similarity NPD1651 Approved
0.72 Intermediate Similarity NPD411 Approved
0.72 Intermediate Similarity NPD1296 Phase 2
0.72 Intermediate Similarity NPD6798 Discontinued
0.7197 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6279 Approved
0.7178 Intermediate Similarity NPD6280 Approved
0.7176 Intermediate Similarity NPD3751 Discontinued
0.717 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD6234 Discontinued
0.7162 Intermediate Similarity NPD1019 Discontinued
0.716 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6585 Discontinued
0.7152 Intermediate Similarity NPD4965 Approved
0.7152 Intermediate Similarity NPD4967 Phase 2
0.7152 Intermediate Similarity NPD4966 Approved
0.7143 Intermediate Similarity NPD1283 Approved
0.7134 Intermediate Similarity NPD5761 Phase 2
0.7134 Intermediate Similarity NPD5760 Phase 2
0.712 Intermediate Similarity NPD7697 Approved
0.712 Intermediate Similarity NPD7698 Approved
0.712 Intermediate Similarity NPD7435 Discontinued
0.712 Intermediate Similarity NPD7696 Phase 3

  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