Structure

Physi-Chem Properties

Molecular Weight:  974.29
Volume:  879.91
LogP:  -0.501
LogD:  -0.487
LogS:  -2.414
# Rotatable Bonds:  15
TPSA:  402.57
# H-Bond Aceptor:  26
# H-Bond Donor:  13
# Rings:  7
# Heavy Atoms:  26

MedChem Properties

QED Drug-Likeness Score:  0.067
Synthetic Accessibility Score:  6.014
Fsp3:  0.619
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.589
MDCK Permeability:  0.00019120895012747496
Pgp-inhibitor:  0.0
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.999
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.349
Plasma Protein Binding (PPB):  60.61479187011719%
Volume Distribution (VD):  0.505
Pgp-substrate:  17.719789505004883%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.031
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.022
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.077
CYP3A4-inhibitor:  0.019
CYP3A4-substrate:  0.002

ADMET: Excretion

Clearance (CL):  0.663
Half-life (T1/2):  0.751

ADMET: Toxicity

hERG Blockers:  0.591
Human Hepatotoxicity (H-HT):  0.102
Drug-inuced Liver Injury (DILI):  0.963
AMES Toxicity:  0.166
Rat Oral Acute Toxicity:  0.017
Maximum Recommended Daily Dose:  0.0
Skin Sensitization:  0.689
Carcinogencity:  0.079
Eye Corrosion:  0.003
Eye Irritation:  0.049
Respiratory Toxicity:  0.014

Download Data

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

  Natural Product: NPC120952

Natural Product ID:  NPC120952
Common Name*:   Diosmetin-7-O-Beta-D-Glucopyranosyl-(1->2)-6-O-Acetyl-Beta-D-Glucopyranosyl-(1->2)-[Alpha-Lrhamnopyranosyl-(1->6)]-Beta-D-Glucopyranoside
IUPAC Name:   [(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
Synonyms:  
Standard InCHIKey:  BHUVDLGITGTMAI-KOZHEFPZSA-N
Standard InCHI:  InChI=1S/C42H54O26/c1-13-27(48)31(52)35(56)39(61-13)60-12-25-30(51)33(54)37(41(65-25)62-16-7-18(46)26-19(47)9-21(63-22(26)8-16)15-4-5-20(58-3)17(45)6-15)68-42-38(34(55)29(50)24(66-42)11-59-14(2)44)67-40-36(57)32(53)28(49)23(10-43)64-40/h4-9,13,23-25,27-43,45-46,48-57H,10-12H2,1-3H3/t13-,23+,24+,25+,27-,28+,29+,30+,31+,32-,33-,34-,35+,36+,37+,38+,39+,40-,41+,42-/m0/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2[C@H](O[C@H]3[C@H](Oc4cc(O)c5c(c4)oc(cc5=O)c4ccc(c(c4)O)OC)O[C@@H]([C@H]([C@@H]3O)O)CO[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)O[C@@H]([C@H]([C@@H]2O)O)COC(=O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2336743
PubChem CID:   71717056
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003533] Flavonoid-7-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
NPO32535 dracocephalum ruyschiana Species Lamiaceae Eukaryota aerial parts Mongolian n.a. PMID[23356964]

☑ 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
NPT1 Others Radical scavenging activity IC50 > 200.0 ug.mL-1 PMID[506900]

☑ 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 NPC120952 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
0.9878 High Similarity NPC198199
0.9756 High Similarity NPC180918
0.9701 High Similarity NPC192539
0.9641 High Similarity NPC173837
0.9641 High Similarity NPC89052
0.9641 High Similarity NPC251417
0.9634 High Similarity NPC209296
0.9634 High Similarity NPC195257
0.9634 High Similarity NPC86008
0.9588 High Similarity NPC33083
0.9588 High Similarity NPC295625
0.9588 High Similarity NPC470719
0.9588 High Similarity NPC473554
0.9581 High Similarity NPC219043
0.9581 High Similarity NPC292019
0.9581 High Similarity NPC89127
0.9581 High Similarity NPC473862
0.9581 High Similarity NPC471669
0.9581 High Similarity NPC122467
0.9581 High Similarity NPC14187
0.9581 High Similarity NPC202908
0.9581 High Similarity NPC48984
0.9581 High Similarity NPC255799
0.9576 High Similarity NPC79056
0.9576 High Similarity NPC177731
0.9576 High Similarity NPC105095
0.9576 High Similarity NPC44328
0.9529 High Similarity NPC470451
0.9529 High Similarity NPC223860
0.9529 High Similarity NPC25946
0.9529 High Similarity NPC470720
0.9529 High Similarity NPC460984
0.9529 High Similarity NPC275977
0.9529 High Similarity NPC470455
0.9529 High Similarity NPC470713
0.9529 High Similarity NPC249560
0.9529 High Similarity NPC470717
0.9529 High Similarity NPC21359
0.9521 High Similarity NPC476472
0.9521 High Similarity NPC294815
0.9521 High Similarity NPC19108
0.9521 High Similarity NPC220173
0.9521 High Similarity NPC473327
0.9521 High Similarity NPC16194
0.9515 High Similarity NPC105283
0.9515 High Similarity NPC293629
0.9515 High Similarity NPC43587
0.9512 High Similarity NPC298666
0.9512 High Similarity NPC210073
0.9512 High Similarity NPC8856
0.9512 High Similarity NPC115674
0.9512 High Similarity NPC68592
0.9512 High Similarity NPC262222
0.9471 High Similarity NPC162394
0.9471 High Similarity NPC156785
0.9471 High Similarity NPC470445
0.9471 High Similarity NPC35924
0.9471 High Similarity NPC470446
0.9471 High Similarity NPC241781
0.9471 High Similarity NPC470718
0.9471 High Similarity NPC470449
0.9471 High Similarity NPC470447
0.9471 High Similarity NPC199172
0.9467 High Similarity NPC471030
0.9461 High Similarity NPC204693
0.9461 High Similarity NPC208668
0.9461 High Similarity NPC472993
0.9461 High Similarity NPC25724
0.9458 High Similarity NPC51326
0.9458 High Similarity NPC231194
0.9458 High Similarity NPC67105
0.9458 High Similarity NPC285197
0.9451 High Similarity NPC284277
0.9451 High Similarity NPC475366
0.9451 High Similarity NPC475497
0.9451 High Similarity NPC311830
0.9451 High Similarity NPC15358
0.9451 High Similarity NPC22832
0.9419 High Similarity NPC30011
0.9419 High Similarity NPC97817
0.9419 High Similarity NPC72554
0.9408 High Similarity NPC475261
0.9405 High Similarity NPC142996
0.9405 High Similarity NPC253685
0.9405 High Similarity NPC102028
0.9401 High Similarity NPC137871
0.9401 High Similarity NPC254540
0.9401 High Similarity NPC60735
0.9401 High Similarity NPC153755
0.9401 High Similarity NPC33054
0.9401 High Similarity NPC203259
0.9401 High Similarity NPC471748
0.9401 High Similarity NPC9002
0.9401 High Similarity NPC256760
0.9401 High Similarity NPC211594
0.9401 High Similarity NPC172807
0.9401 High Similarity NPC176740
0.9401 High Similarity NPC3583
0.9401 High Similarity NPC26230
0.9401 High Similarity NPC471725
0.9401 High Similarity NPC257011
0.9401 High Similarity NPC155877
0.9401 High Similarity NPC134532
0.9401 High Similarity NPC259152
0.9401 High Similarity NPC288152
0.9398 High Similarity NPC227508
0.9394 High Similarity NPC5778
0.9394 High Similarity NPC236934
0.939 High Similarity NPC311850
0.939 High Similarity NPC222936
0.939 High Similarity NPC284960
0.939 High Similarity NPC309025
0.939 High Similarity NPC19709
0.939 High Similarity NPC270335
0.939 High Similarity NPC191306
0.939 High Similarity NPC88023
0.939 High Similarity NPC243930
0.936 High Similarity NPC474093
0.936 High Similarity NPC104910
0.9353 High Similarity NPC241423
0.9353 High Similarity NPC110941
0.9353 High Similarity NPC470444
0.9353 High Similarity NPC473571
0.9353 High Similarity NPC126784
0.9353 High Similarity NPC470443
0.9353 High Similarity NPC473895
0.9353 High Similarity NPC473682
0.9349 High Similarity NPC169733
0.9345 High Similarity NPC239549
0.9345 High Similarity NPC236191
0.9345 High Similarity NPC88560
0.9345 High Similarity NPC175230
0.9345 High Similarity NPC4390
0.9345 High Similarity NPC172033
0.9345 High Similarity NPC51774
0.9341 High Similarity NPC78734
0.9341 High Similarity NPC199079
0.9341 High Similarity NPC136042
0.9341 High Similarity NPC244776
0.9341 High Similarity NPC210808
0.9341 High Similarity NPC67326
0.9341 High Similarity NPC156869
0.9341 High Similarity NPC116864
0.9341 High Similarity NPC95866
0.9341 High Similarity NPC259896
0.9341 High Similarity NPC150767
0.9341 High Similarity NPC29958
0.9341 High Similarity NPC254855
0.9341 High Similarity NPC255157
0.9341 High Similarity NPC218488
0.9337 High Similarity NPC116745
0.9337 High Similarity NPC275454
0.9337 High Similarity NPC229729
0.9329 High Similarity NPC473043
0.9329 High Similarity NPC298171
0.9329 High Similarity NPC475382
0.9329 High Similarity NPC189142
0.9329 High Similarity NPC77660
0.9306 High Similarity NPC475179
0.9298 High Similarity NPC469371
0.9294 High Similarity NPC477895
0.9294 High Similarity NPC241196
0.9294 High Similarity NPC139571
0.9294 High Similarity NPC217520
0.929 High Similarity NPC477848
0.9286 High Similarity NPC47140
0.9286 High Similarity NPC301683
0.9286 High Similarity NPC190003
0.9286 High Similarity NPC472386
0.9286 High Similarity NPC67134
0.9286 High Similarity NPC156977
0.9286 High Similarity NPC175107
0.9286 High Similarity NPC261254
0.9286 High Similarity NPC267254
0.9281 High Similarity NPC469931
0.9281 High Similarity NPC120099
0.9281 High Similarity NPC45638
0.9281 High Similarity NPC203050
0.9281 High Similarity NPC226294
0.9281 High Similarity NPC61791
0.9281 High Similarity NPC186807
0.9281 High Similarity NPC223747
0.9281 High Similarity NPC93337
0.9281 High Similarity NPC225434
0.9281 High Similarity NPC105025
0.9281 High Similarity NPC219904
0.9281 High Similarity NPC201292
0.9281 High Similarity NPC58053
0.9281 High Similarity NPC229687
0.9281 High Similarity NPC475942
0.9277 High Similarity NPC197285
0.9277 High Similarity NPC21100
0.9273 High Similarity NPC29830
0.9273 High Similarity NPC473644
0.9273 High Similarity NPC168822
0.9268 High Similarity NPC182045
0.9268 High Similarity NPC101636
0.9244 High Similarity NPC473072
0.9235 High Similarity NPC472385
0.9235 High Similarity NPC198324

  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 NPC120952 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
0.9695 High Similarity NPD7472 Approved
0.9634 High Similarity NPD7054 Approved
0.9576 High Similarity NPD7074 Phase 3
0.9521 High Similarity NPD7808 Phase 3
0.9461 High Similarity NPD7251 Discontinued
0.9401 High Similarity NPD6797 Phase 2
0.9176 High Similarity NPD4338 Clinical (unspecified phase)
0.8994 High Similarity NPD3818 Discontinued
0.8941 High Similarity NPD7804 Clinical (unspecified phase)
0.8876 High Similarity NPD6166 Phase 2
0.8876 High Similarity NPD6167 Clinical (unspecified phase)
0.8876 High Similarity NPD6168 Clinical (unspecified phase)
0.8855 High Similarity NPD4381 Clinical (unspecified phase)
0.8727 High Similarity NPD1934 Approved
0.8623 High Similarity NPD3817 Phase 2
0.8563 High Similarity NPD2801 Approved
0.8563 High Similarity NPD2393 Clinical (unspecified phase)
0.8514 High Similarity NPD7993 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD1511 Approved
0.8304 Intermediate Similarity NPD7075 Discontinued
0.8274 Intermediate Similarity NPD4380 Phase 2
0.8258 Intermediate Similarity NPD6559 Discontinued
0.8253 Intermediate Similarity NPD1512 Approved
0.8246 Intermediate Similarity NPD3882 Suspended
0.8167 Intermediate Similarity NPD8312 Approved
0.8167 Intermediate Similarity NPD8313 Approved
0.8156 Intermediate Similarity NPD7685 Pre-registration
0.8155 Intermediate Similarity NPD1653 Approved
0.8136 Intermediate Similarity NPD7228 Approved
0.8129 Intermediate Similarity NPD7819 Suspended
0.8129 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8081 Intermediate Similarity NPD5402 Approved
0.807 Intermediate Similarity NPD6801 Discontinued
0.8054 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD1465 Phase 2
0.8 Intermediate Similarity NPD5494 Approved
0.7989 Intermediate Similarity NPD5844 Phase 1
0.7988 Intermediate Similarity NPD5403 Approved
0.7978 Intermediate Similarity NPD7473 Discontinued
0.7977 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7946 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD8455 Phase 2
0.7917 Intermediate Similarity NPD6799 Approved
0.791 Intermediate Similarity NPD6232 Discontinued
0.7907 Intermediate Similarity NPD7411 Suspended
0.7897 Intermediate Similarity NPD8151 Discontinued
0.7882 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD7266 Discontinued
0.7879 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD5401 Approved
0.787 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD6959 Discontinued
0.7853 Intermediate Similarity NPD7199 Phase 2
0.7831 Intermediate Similarity NPD1549 Phase 2
0.7821 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD7783 Phase 2
0.7817 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD7240 Approved
0.774 Intermediate Similarity NPD6234 Discontinued
0.7711 Intermediate Similarity NPD2796 Approved
0.7667 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD37 Approved
0.7651 Intermediate Similarity NPD1510 Phase 2
0.7644 Intermediate Similarity NPD6599 Discontinued
0.7637 Intermediate Similarity NPD3751 Discontinued
0.7633 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD4966 Approved
0.7627 Intermediate Similarity NPD4967 Phase 2
0.7627 Intermediate Similarity NPD7768 Phase 2
0.7627 Intermediate Similarity NPD4965 Approved
0.7619 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD3787 Discontinued
0.7602 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD1933 Approved
0.7551 Intermediate Similarity NPD7435 Discontinued
0.7542 Intermediate Similarity NPD919 Approved
0.7529 Intermediate Similarity NPD3750 Approved
0.7525 Intermediate Similarity NPD7584 Approved
0.7515 Intermediate Similarity NPD1613 Approved
0.7515 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD230 Phase 1
0.7462 Intermediate Similarity NPD7698 Approved
0.7462 Intermediate Similarity NPD7696 Phase 3
0.7462 Intermediate Similarity NPD7697 Approved
0.7427 Intermediate Similarity NPD4628 Phase 3
0.7424 Intermediate Similarity NPD8320 Phase 1
0.7424 Intermediate Similarity NPD8319 Approved
0.7423 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD7874 Approved
0.741 Intermediate Similarity NPD1240 Approved
0.74 Intermediate Similarity NPD7701 Phase 2
0.7398 Intermediate Similarity NPD6781 Approved
0.7398 Intermediate Similarity NPD6779 Approved
0.7398 Intermediate Similarity NPD6780 Approved
0.7398 Intermediate Similarity NPD6777 Approved
0.7398 Intermediate Similarity NPD6778 Approved
0.7398 Intermediate Similarity NPD6782 Approved
0.7398 Intermediate Similarity NPD6776 Approved
0.7396 Intermediate Similarity NPD1551 Phase 2
0.7389 Intermediate Similarity NPD3749 Approved
0.7384 Intermediate Similarity NPD6190 Approved
0.7374 Intermediate Similarity NPD7680 Approved
0.7365 Intermediate Similarity NPD447 Suspended
0.7347 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7870 Phase 2
0.7337 Intermediate Similarity NPD7871 Phase 2
0.7333 Intermediate Similarity NPD3027 Phase 3
0.7321 Intermediate Similarity NPD1607 Approved
0.7313 Intermediate Similarity NPD7585 Approved
0.7305 Intermediate Similarity NPD943 Approved
0.7296 Intermediate Similarity NPD7700 Phase 2
0.7296 Intermediate Similarity NPD7699 Phase 2
0.7294 Intermediate Similarity NPD2935 Discontinued
0.7288 Intermediate Similarity NPD7458 Discontinued
0.7283 Intermediate Similarity NPD3926 Phase 2
0.7277 Intermediate Similarity NPD8434 Phase 2
0.7277 Intermediate Similarity NPD8150 Discontinued
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD1247 Approved
0.7267 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD7583 Approved
0.7257 Intermediate Similarity NPD2533 Approved
0.7257 Intermediate Similarity NPD2532 Approved
0.7257 Intermediate Similarity NPD2534 Approved
0.7236 Intermediate Similarity NPD6823 Phase 2
0.7235 Intermediate Similarity NPD3748 Approved
0.7212 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD7801 Approved
0.7175 Intermediate Similarity NPD920 Approved
0.7169 Intermediate Similarity NPD6832 Phase 2
0.7159 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6534 Approved
0.7143 Intermediate Similarity NPD6535 Approved
0.7143 Intermediate Similarity NPD5953 Discontinued
0.7136 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7033 Discontinued
0.7128 Intermediate Similarity NPD7286 Phase 2
0.7095 Intermediate Similarity NPD3226 Approved
0.7088 Intermediate Similarity NPD5353 Approved
0.7081 Intermediate Similarity NPD8127 Discontinued
0.7069 Intermediate Similarity NPD6674 Discontinued
0.7069 Intermediate Similarity NPD1652 Phase 2
0.7069 Intermediate Similarity NPD1243 Approved
0.7062 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7930 Approved
0.6995 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6994 Remote Similarity NPD6100 Approved
0.6994 Remote Similarity NPD6099 Approved
0.6988 Remote Similarity NPD1203 Approved
0.6982 Remote Similarity NPD2313 Discontinued
0.6979 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6978 Remote Similarity NPD6844 Discontinued
0.6971 Remote Similarity NPD2800 Approved
0.697 Remote Similarity NPD4363 Phase 3
0.697 Remote Similarity NPD4360 Phase 2
0.6959 Remote Similarity NPD5124 Phase 1
0.6959 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2346 Discontinued
0.6951 Remote Similarity NPD1091 Approved
0.6936 Remote Similarity NPD651 Clinical (unspecified phase)
0.6936 Remote Similarity NPD2799 Discontinued
0.6923 Remote Similarity NPD6386 Approved
0.6923 Remote Similarity NPD6385 Approved
0.6923 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6651 Approved
0.6919 Remote Similarity NPD6212 Phase 3
0.6919 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6213 Phase 3
0.6915 Remote Similarity NPD5242 Approved
0.691 Remote Similarity NPD7390 Discontinued
0.6907 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6906 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6905 Remote Similarity NPD9494 Approved
0.6897 Remote Similarity NPD5006 Approved
0.6897 Remote Similarity NPD5005 Approved
0.6891 Remote Similarity NPD7549 Discontinued
0.6882 Remote Similarity NPD6798 Discontinued
0.6882 Remote Similarity NPD3268 Approved
0.6879 Remote Similarity NPD7097 Phase 1
0.6867 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6864 Remote Similarity NPD4908 Phase 1
0.6862 Remote Similarity NPD5711 Approved
0.6862 Remote Similarity NPD5710 Approved
0.686 Remote Similarity NPD6355 Discontinued
0.6848 Remote Similarity NPD422 Phase 1
0.6845 Remote Similarity NPD2798 Approved
0.6842 Remote Similarity NPD6233 Phase 2
0.6839 Remote Similarity NPD7038 Approved
0.6839 Remote Similarity NPD7039 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