Structure

Physi-Chem Properties

Molecular Weight:  314.08
Volume:  308.569
LogP:  3.08
LogD:  2.77
LogS:  -3.566
# Rotatable Bonds:  3
TPSA:  89.13
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.772
Synthetic Accessibility Score:  2.327
Fsp3:  0.118
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.785
MDCK Permeability:  1.2895844520244282e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.949
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.018
Plasma Protein Binding (PPB):  94.70122528076172%
Volume Distribution (VD):  0.57
Pgp-substrate:  5.799776554107666%

ADMET: Metabolism

CYP1A2-inhibitor:  0.965
CYP1A2-substrate:  0.931
CYP2C19-inhibitor:  0.847
CYP2C19-substrate:  0.062
CYP2C9-inhibitor:  0.743
CYP2C9-substrate:  0.949
CYP2D6-inhibitor:  0.901
CYP2D6-substrate:  0.917
CYP3A4-inhibitor:  0.821
CYP3A4-substrate:  0.152

ADMET: Excretion

Clearance (CL):  7.995
Half-life (T1/2):  0.753

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.135
Drug-inuced Liver Injury (DILI):  0.627
AMES Toxicity:  0.223
Rat Oral Acute Toxicity:  0.198
Maximum Recommended Daily Dose:  0.618
Skin Sensitization:  0.672
Carcinogencity:  0.076
Eye Corrosion:  0.018
Eye Irritation:  0.922
Respiratory Toxicity:  0.318

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

  Natural Product: NPC278323

Natural Product ID:  NPC278323
Common Name*:   2'-Methoxybiochanin A
IUPAC Name:   3-(2,4-dimethoxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:   2'-Methoxybiochanin A
Standard InCHIKey:  PBUHDEMRGWYORH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C17H14O6/c1-21-10-3-4-11(14(7-10)22-2)12-8-23-15-6-9(18)5-13(19)16(15)17(12)20/h3-8,18-19H,1-2H3
SMILES:  COc1ccc(c2coc3cc(cc(c3c2=O)O)O)c(c1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1088580
PubChem CID:   44257324
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002586] O-methylated isoflavonoids
          • [CHEMONTID:0002606] 4'-O-methylated isoflavonoids
            • [CHEMONTID:0002687] 4'-O-methylisoflavones

*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
NPO14114 Dalbergia parviflora Species Fabaceae Eukaryota heartwood n.a. n.a. PMID[19928832]
NPO14114 Dalbergia parviflora 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
NPT396 Cell Line T47D Homo sapiens Activity = 3.1 uM PMID[473676]
NPT396 Cell Line T47D Homo sapiens Activity = 1.8 uM PMID[473676]
NPT83 Cell Line MCF7 Homo sapiens Activity > 100.0 uM PMID[473676]
NPT396 Cell Line T47D Homo sapiens Activity > 100.0 uM PMID[473676]
NPT396 Cell Line T47D Homo sapiens Activity = 0.4 uM PMID[473676]
NPT83 Cell Line MCF7 Homo sapiens Activity = 19.6 uM PMID[473676]
NPT83 Cell Line MCF7 Homo sapiens Activity = 3.2 uM PMID[473676]

☑ 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 NPC278323 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 NPC279668
1.0 High Similarity NPC12175
1.0 High Similarity NPC309154
1.0 High Similarity NPC90665
1.0 High Similarity NPC55162
0.9924 High Similarity NPC162680
0.9924 High Similarity NPC209560
0.9924 High Similarity NPC7013
0.9924 High Similarity NPC294409
0.9924 High Similarity NPC303644
0.9924 High Similarity NPC116632
0.9924 High Similarity NPC181124
0.9851 High Similarity NPC101366
0.9848 High Similarity NPC87545
0.9848 High Similarity NPC235428
0.9778 High Similarity NPC52789
0.9778 High Similarity NPC26051
0.9778 High Similarity NPC55832
0.9778 High Similarity NPC268204
0.9776 High Similarity NPC295384
0.9773 High Similarity NPC234560
0.9773 High Similarity NPC39426
0.9704 High Similarity NPC80962
0.9704 High Similarity NPC326109
0.9704 High Similarity NPC172250
0.9704 High Similarity NPC48624
0.9704 High Similarity NPC213659
0.9704 High Similarity NPC259166
0.9704 High Similarity NPC144118
0.9704 High Similarity NPC204985
0.9704 High Similarity NPC219917
0.9704 High Similarity NPC253822
0.9704 High Similarity NPC215311
0.9632 High Similarity NPC469404
0.963 High Similarity NPC283429
0.9627 High Similarity NPC212767
0.9565 High Similarity NPC476055
0.9552 High Similarity NPC193792
0.9549 High Similarity NPC286336
0.9545 High Similarity NPC205468
0.9545 High Similarity NPC129132
0.9545 High Similarity NPC87231
0.9545 High Similarity NPC182428
0.9545 High Similarity NPC212631
0.9545 High Similarity NPC257756
0.9493 High Similarity NPC117836
0.9493 High Similarity NPC51887
0.9493 High Similarity NPC475705
0.9493 High Similarity NPC476178
0.9485 High Similarity NPC477956
0.9481 High Similarity NPC266597
0.9481 High Similarity NPC472419
0.9481 High Similarity NPC228661
0.9481 High Similarity NPC250266
0.9474 High Similarity NPC20560
0.9474 High Similarity NPC472365
0.9474 High Similarity NPC159623
0.9474 High Similarity NPC188646
0.9474 High Similarity NPC139813
0.9474 High Similarity NPC242294
0.9474 High Similarity NPC192304
0.9474 High Similarity NPC144051
0.9474 High Similarity NPC294593
0.9474 High Similarity NPC337373
0.9474 High Similarity NPC28753
0.9474 High Similarity NPC312318
0.9474 High Similarity NPC175098
0.9474 High Similarity NPC223354
0.9474 High Similarity NPC82225
0.9474 High Similarity NPC263670
0.9474 High Similarity NPC56031
0.9474 High Similarity NPC18877
0.9474 High Similarity NPC204960
0.947 High Similarity NPC262359
0.947 High Similarity NPC64359
0.947 High Similarity NPC308037
0.947 High Similarity NPC313618
0.9424 High Similarity NPC234629
0.9424 High Similarity NPC303185
0.9424 High Similarity NPC184649
0.9424 High Similarity NPC311741
0.942 High Similarity NPC202981
0.9412 High Similarity NPC21350
0.9412 High Similarity NPC99333
0.9412 High Similarity NPC188947
0.9412 High Similarity NPC124269
0.9412 High Similarity NPC280284
0.9407 High Similarity NPC213603
0.9407 High Similarity NPC41461
0.9407 High Similarity NPC477244
0.9407 High Similarity NPC234133
0.9407 High Similarity NPC274109
0.9407 High Similarity NPC150399
0.9407 High Similarity NPC98115
0.9407 High Similarity NPC47815
0.9407 High Similarity NPC477243
0.9407 High Similarity NPC473887
0.9407 High Similarity NPC186838
0.9407 High Similarity NPC29353
0.9407 High Similarity NPC477242
0.9407 High Similarity NPC124784
0.9407 High Similarity NPC168105
0.9407 High Similarity NPC66349
0.9407 High Similarity NPC1486
0.9407 High Similarity NPC25287
0.9407 High Similarity NPC473391
0.9407 High Similarity NPC231772
0.9407 High Similarity NPC249606
0.9407 High Similarity NPC472364
0.9407 High Similarity NPC127447
0.9407 High Similarity NPC12165
0.9407 High Similarity NPC194281
0.9362 High Similarity NPC266572
0.9357 High Similarity NPC12377
0.9357 High Similarity NPC299011
0.9353 High Similarity NPC113770
0.9348 High Similarity NPC3188
0.9348 High Similarity NPC110969
0.9348 High Similarity NPC321980
0.9348 High Similarity NPC49108
0.9348 High Similarity NPC470089
0.9348 High Similarity NPC470087
0.9343 High Similarity NPC78913
0.9343 High Similarity NPC261234
0.9343 High Similarity NPC222342
0.9343 High Similarity NPC49242
0.9343 High Similarity NPC150648
0.9343 High Similarity NPC225153
0.9343 High Similarity NPC470211
0.9343 High Similarity NPC329203
0.9343 High Similarity NPC310135
0.9343 High Similarity NPC274784
0.9343 High Similarity NPC18260
0.9343 High Similarity NPC265871
0.9343 High Similarity NPC20709
0.9338 High Similarity NPC275055
0.9338 High Similarity NPC317119
0.9338 High Similarity NPC153979
0.9338 High Similarity NPC290291
0.9338 High Similarity NPC188879
0.9333 High Similarity NPC156092
0.9333 High Similarity NPC131039
0.9333 High Similarity NPC13575
0.9323 High Similarity NPC128348
0.9323 High Similarity NPC309717
0.9323 High Similarity NPC66384
0.9323 High Similarity NPC164236
0.9323 High Similarity NPC475008
0.9323 High Similarity NPC112192
0.9323 High Similarity NPC186097
0.9323 High Similarity NPC189106
0.9323 High Similarity NPC475009
0.9318 High Similarity NPC185497
0.9318 High Similarity NPC247779
0.9296 High Similarity NPC317492
0.9296 High Similarity NPC264550
0.9296 High Similarity NPC195763
0.9296 High Similarity NPC139293
0.9296 High Similarity NPC69430
0.9296 High Similarity NPC200060
0.9296 High Similarity NPC333691
0.9296 High Similarity NPC142876
0.9296 High Similarity NPC40290
0.9296 High Similarity NPC264289
0.9291 High Similarity NPC104406
0.9291 High Similarity NPC97716
0.9291 High Similarity NPC79469
0.9291 High Similarity NPC201731
0.9291 High Similarity NPC222298
0.9291 High Similarity NPC24673
0.9291 High Similarity NPC237635
0.9291 High Similarity NPC51070
0.9286 High Similarity NPC311144
0.9281 High Similarity NPC11561
0.9281 High Similarity NPC226636
0.9275 High Similarity NPC129853
0.9275 High Similarity NPC188243
0.9275 High Similarity NPC110228
0.9275 High Similarity NPC269652
0.9275 High Similarity NPC6407
0.9275 High Similarity NPC76445
0.9275 High Similarity NPC270883
0.9275 High Similarity NPC159275
0.9275 High Similarity NPC284550
0.9275 High Similarity NPC241100
0.9275 High Similarity NPC281207
0.9275 High Similarity NPC172986
0.9275 High Similarity NPC261227
0.9275 High Similarity NPC265178
0.9275 High Similarity NPC11056
0.927 High Similarity NPC118813
0.927 High Similarity NPC251681
0.927 High Similarity NPC471620
0.927 High Similarity NPC25427
0.927 High Similarity NPC329225
0.927 High Similarity NPC201395
0.927 High Similarity NPC243528
0.927 High Similarity NPC472460
0.927 High Similarity NPC147686
0.927 High Similarity NPC472368

  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 NPC278323 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
0.9773 High Similarity NPD1510 Phase 2
0.947 High Similarity NPD1240 Approved
0.9328 High Similarity NPD1607 Approved
0.927 High Similarity NPD1549 Phase 2
0.9197 High Similarity NPD1552 Clinical (unspecified phase)
0.9197 High Similarity NPD1550 Clinical (unspecified phase)
0.9149 High Similarity NPD4378 Clinical (unspecified phase)
0.9124 High Similarity NPD2796 Approved
0.8966 High Similarity NPD4380 Phase 2
0.8881 High Similarity NPD7410 Clinical (unspecified phase)
0.8732 High Similarity NPD1878 Clinical (unspecified phase)
0.8716 High Similarity NPD1934 Approved
0.8681 High Similarity NPD1511 Approved
0.8658 High Similarity NPD2393 Clinical (unspecified phase)
0.8658 High Similarity NPD2801 Approved
0.8649 High Similarity NPD7411 Suspended
0.8609 High Similarity NPD7075 Discontinued
0.8609 High Similarity NPD4381 Clinical (unspecified phase)
0.8601 High Similarity NPD3750 Approved
0.86 High Similarity NPD8443 Clinical (unspecified phase)
0.8592 High Similarity NPD970 Clinical (unspecified phase)
0.8562 High Similarity NPD1512 Approved
0.8552 High Similarity NPD6799 Approved
0.8543 High Similarity NPD3882 Suspended
0.8533 High Similarity NPD7819 Suspended
0.8533 High Similarity NPD7096 Clinical (unspecified phase)
0.8467 Intermediate Similarity NPD6801 Discontinued
0.8451 Intermediate Similarity NPD1551 Phase 2
0.8366 Intermediate Similarity NPD3749 Approved
0.8357 Intermediate Similarity NPD943 Approved
0.8333 Intermediate Similarity NPD6599 Discontinued
0.8322 Intermediate Similarity NPD2935 Discontinued
0.8301 Intermediate Similarity NPD7768 Phase 2
0.8291 Intermediate Similarity NPD3818 Discontinued
0.828 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD2800 Approved
0.8264 Intermediate Similarity NPD2344 Approved
0.8255 Intermediate Similarity NPD920 Approved
0.8252 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8252 Intermediate Similarity NPD3748 Approved
0.8239 Intermediate Similarity NPD6651 Approved
0.8235 Intermediate Similarity NPD3817 Phase 2
0.8214 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8188 Intermediate Similarity NPD2798 Approved
0.8165 Intermediate Similarity NPD6166 Phase 2
0.8165 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8165 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8153 Intermediate Similarity NPD6232 Discontinued
0.8151 Intermediate Similarity NPD1243 Approved
0.8133 Intermediate Similarity NPD5403 Approved
0.8125 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD5401 Approved
0.8121 Intermediate Similarity NPD2533 Approved
0.8121 Intermediate Similarity NPD2532 Approved
0.8121 Intermediate Similarity NPD2534 Approved
0.8121 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD7473 Discontinued
0.8108 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD6959 Discontinued
0.8085 Intermediate Similarity NPD2313 Discontinued
0.8065 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD2309 Approved
0.8025 Intermediate Similarity NPD5494 Approved
0.8025 Intermediate Similarity NPD5953 Discontinued
0.8012 Intermediate Similarity NPD7054 Approved
0.8 Intermediate Similarity NPD2799 Discontinued
0.8 Intermediate Similarity NPD5402 Approved
0.7986 Intermediate Similarity NPD1203 Approved
0.7963 Intermediate Similarity NPD7074 Phase 3
0.7963 Intermediate Similarity NPD7472 Approved
0.7956 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7927 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7926 Intermediate Similarity NPD1548 Phase 1
0.7914 Intermediate Similarity NPD6797 Phase 2
0.7901 Intermediate Similarity NPD7286 Phase 2
0.7866 Intermediate Similarity NPD7251 Discontinued
0.7852 Intermediate Similarity NPD4628 Phase 3
0.7826 Intermediate Similarity NPD1610 Phase 2
0.7818 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD7808 Phase 3
0.7817 Intermediate Similarity NPD6832 Phase 2
0.7817 Intermediate Similarity NPD4908 Phase 1
0.7794 Intermediate Similarity NPD9545 Approved
0.7793 Intermediate Similarity NPD230 Phase 1
0.7792 Intermediate Similarity NPD3226 Approved
0.7785 Intermediate Similarity NPD2654 Approved
0.7778 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD9493 Approved
0.777 Intermediate Similarity NPD9717 Approved
0.777 Intermediate Similarity NPD3972 Approved
0.7758 Intermediate Similarity NPD6559 Discontinued
0.7755 Intermediate Similarity NPD4308 Phase 3
0.7755 Intermediate Similarity NPD7033 Discontinued
0.775 Intermediate Similarity NPD1247 Approved
0.7736 Intermediate Similarity NPD919 Approved
0.773 Intermediate Similarity NPD1470 Approved
0.7708 Intermediate Similarity NPD3764 Approved
0.7708 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD3268 Approved
0.7703 Intermediate Similarity NPD6100 Approved
0.7703 Intermediate Similarity NPD6099 Approved
0.7698 Intermediate Similarity NPD422 Phase 1
0.7697 Intermediate Similarity NPD7390 Discontinued
0.7654 Intermediate Similarity NPD3926 Phase 2
0.7651 Intermediate Similarity NPD2346 Discontinued
0.7635 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD2797 Approved
0.7595 Intermediate Similarity NPD1465 Phase 2
0.759 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD5844 Phase 1
0.7571 Intermediate Similarity NPD1201 Approved
0.7564 Intermediate Similarity NPD7458 Discontinued
0.7551 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD4288 Approved
0.7535 Intermediate Similarity NPD3225 Approved
0.7535 Intermediate Similarity NPD1876 Approved
0.75 Intermediate Similarity NPD9494 Approved
0.75 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD5711 Approved
0.7485 Intermediate Similarity NPD5710 Approved
0.7483 Intermediate Similarity NPD4307 Phase 2
0.7483 Intermediate Similarity NPD3266 Approved
0.7483 Intermediate Similarity NPD3267 Approved
0.7483 Intermediate Similarity NPD1164 Approved
0.7471 Intermediate Similarity NPD4363 Phase 3
0.7471 Intermediate Similarity NPD4360 Phase 2
0.7438 Intermediate Similarity NPD2296 Approved
0.7432 Intermediate Similarity NPD1933 Approved
0.7432 Intermediate Similarity NPD447 Suspended
0.7429 Intermediate Similarity NPD4361 Phase 2
0.7429 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD1241 Discontinued
0.7397 Intermediate Similarity NPD3027 Phase 3
0.7394 Intermediate Similarity NPD1608 Approved
0.7386 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7003 Approved
0.7365 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1613 Approved
0.7358 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD5408 Approved
0.7351 Intermediate Similarity NPD5404 Approved
0.7351 Intermediate Similarity NPD5406 Approved
0.7351 Intermediate Similarity NPD5405 Approved
0.7347 Intermediate Similarity NPD411 Approved
0.7347 Intermediate Similarity NPD1296 Phase 2
0.7341 Intermediate Similarity NPD4287 Approved
0.7329 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD1729 Discontinued
0.7315 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD5124 Phase 1
0.7312 Intermediate Similarity NPD6844 Discontinued
0.731 Intermediate Similarity NPD1019 Discontinued
0.7308 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD3751 Discontinued
0.7303 Intermediate Similarity NPD1471 Phase 3
0.7303 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6104 Discontinued
0.723 Intermediate Similarity NPD6798 Discontinued
0.7222 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD6279 Approved
0.7205 Intermediate Similarity NPD6280 Approved
0.7205 Intermediate Similarity NPD37 Approved
0.7186 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD9266 Approved
0.7185 Intermediate Similarity NPD74 Approved
0.7183 Intermediate Similarity NPD17 Approved
0.7169 Intermediate Similarity NPD7229 Phase 3
0.7162 Intermediate Similarity NPD4625 Phase 3
0.7153 Intermediate Similarity NPD9269 Phase 2
0.7143 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5889 Approved
0.7143 Intermediate Similarity NPD5890 Approved
0.7126 Intermediate Similarity NPD5242 Approved
0.7125 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD7584 Approved
0.7115 Intermediate Similarity NPD2354 Approved
0.7115 Intermediate Similarity NPD6190 Approved
0.7113 Intermediate Similarity NPD9268 Approved
0.7113 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD9267 Approved
0.7111 Intermediate Similarity NPD9264 Approved
0.7111 Intermediate Similarity NPD9263 Approved
0.7111 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7199 Phase 2
0.7103 Intermediate Similarity NPD4749 Approved
0.7101 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6234 Discontinued
0.7089 Intermediate Similarity NPD7447 Phase 1
0.7089 Intermediate Similarity NPD4661 Approved
0.7089 Intermediate Similarity NPD4662 Approved
0.7086 Intermediate Similarity NPD6355 Discontinued
0.7083 Intermediate Similarity NPD2403 Approved
0.7073 Intermediate Similarity NPD4966 Approved
0.7073 Intermediate Similarity NPD4965 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