Structure

Physi-Chem Properties

Molecular Weight:  722.21
Volume:  668.401
LogP:  1.371
LogD:  0.969
LogS:  -5.266
# Rotatable Bonds:  12
TPSA:  263.5
# H-Bond Aceptor:  18
# H-Bond Donor:  6
# Rings:  5
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.15
Synthetic Accessibility Score:  5.131
Fsp3:  0.515
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.374
MDCK Permeability:  7.941130024846643e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.934
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.147
Plasma Protein Binding (PPB):  52.812713623046875%
Volume Distribution (VD):  0.337
Pgp-substrate:  43.94987106323242%

ADMET: Metabolism

CYP1A2-inhibitor:  0.023
CYP1A2-substrate:  0.022
CYP2C19-inhibitor:  0.036
CYP2C19-substrate:  0.054
CYP2C9-inhibitor:  0.055
CYP2C9-substrate:  0.188
CYP2D6-inhibitor:  0.774
CYP2D6-substrate:  0.106
CYP3A4-inhibitor:  0.654
CYP3A4-substrate:  0.172

ADMET: Excretion

Clearance (CL):  1.366
Half-life (T1/2):  0.923

ADMET: Toxicity

hERG Blockers:  0.141
Human Hepatotoxicity (H-HT):  0.944
Drug-inuced Liver Injury (DILI):  0.977
AMES Toxicity:  0.198
Rat Oral Acute Toxicity:  0.131
Maximum Recommended Daily Dose:  0.018
Skin Sensitization:  0.143
Carcinogencity:  0.188
Eye Corrosion:  0.003
Eye Irritation:  0.048
Respiratory Toxicity:  0.171

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

  Natural Product: NPC257011

Natural Product ID:  NPC257011
Common Name*:   (2S)-5,7,5'-Trihydroxyflavanone 2'-O-Beta-D-2,6-Di-O-Acetylglucopyranosyl-(1->3)-Alpha-L-2-O-Acetylrhamnopyanoside
IUPAC Name:   [(2R,3S,4S,5R,6S)-5-acetyloxy-6-[(2S,3R,4R,5S,6S)-3-acetyloxy-2-[2-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-hydroxyphenoxy]-5-hydroxy-6-methyloxan-4-yl]oxy-3,4-dihydroxyoxan-2-yl]methyl acetate
Synonyms:  
Standard InCHIKey:  ICNDFIPHAKXPNB-DREMMWLKSA-N
Standard InCHI:  InChI=1S/C33H38O18/c1-12-26(41)29(51-32-30(46-14(3)35)28(43)27(42)24(50-32)11-44-13(2)34)31(47-15(4)36)33(45-12)49-21-6-5-16(37)7-18(21)22-10-20(40)25-19(39)8-17(38)9-23(25)48-22/h5-9,12,22,24,26-33,37-39,41-43H,10-11H2,1-4H3/t12-,22-,24+,26-,27+,28-,29+,30+,31+,32-,33-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1ccc(cc1[C@@H]1CC(=O)c2c(cc(cc2O1)O)O)O)OC(=O)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)C)O1)O)O)OC(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL443432
PubChem CID:   11995179
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0001632] Flavanones

*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
NPO26960 Cyclosorus acuminatus Species Thelypteridaceae Eukaryota rhizomes n.a. n.a. PMID[17125239]
NPO26960 Cyclosorus acuminatus Species Thelypteridaceae 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 128.0 ug.mL-1 PMID[459848]
NPT19 Organism Escherichia coli Escherichia coli MIC = 64.0 ug.mL-1 PMID[459848]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae MIC = 32.0 ug.mL-1 PMID[459848]
NPT1122 Organism Haemophilus influenzae Haemophilus influenzae MIC = 32.0 ug.mL-1 PMID[459848]

☑ 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 NPC257011 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 NPC9002
1.0 High Similarity NPC288152
1.0 High Similarity NPC137871
0.9938 High Similarity NPC210808
0.9938 High Similarity NPC199079
0.975 High Similarity NPC70441
0.9515 High Similarity NPC102028
0.9506 High Similarity NPC68592
0.9506 High Similarity NPC298666
0.9506 High Similarity NPC262222
0.9441 High Similarity NPC475382
0.9441 High Similarity NPC298171
0.9437 High Similarity NPC271270
0.9437 High Similarity NPC246469
0.9437 High Similarity NPC142860
0.9437 High Similarity NPC97285
0.9401 High Similarity NPC120952
0.9398 High Similarity NPC142996
0.9394 High Similarity NPC472386
0.9394 High Similarity NPC301683
0.9394 High Similarity NPC267254
0.9394 High Similarity NPC156977
0.939 High Similarity NPC105283
0.939 High Similarity NPC293629
0.939 High Similarity NPC43587
0.9383 High Similarity NPC311850
0.9383 High Similarity NPC473644
0.9379 High Similarity NPC101636
0.9337 High Similarity NPC51774
0.9337 High Similarity NPC239549
0.9337 High Similarity NPC236191
0.9333 High Similarity NPC105095
0.9333 High Similarity NPC194483
0.9333 High Similarity NPC44328
0.9333 High Similarity NPC52353
0.9333 High Similarity NPC79056
0.9333 High Similarity NPC293004
0.9333 High Similarity NPC177731
0.9329 High Similarity NPC249977
0.9325 High Similarity NPC287889
0.9325 High Similarity NPC135358
0.9325 High Similarity NPC99216
0.9321 High Similarity NPC190450
0.9294 High Similarity NPC470455
0.9294 High Similarity NPC470451
0.9286 High Similarity NPC475261
0.9286 High Similarity NPC472387
0.9281 High Similarity NPC198199
0.9277 High Similarity NPC180918
0.9273 High Similarity NPC472381
0.9273 High Similarity NPC472383
0.9268 High Similarity NPC477613
0.9268 High Similarity NPC32641
0.9268 High Similarity NPC221342
0.9268 High Similarity NPC142142
0.9268 High Similarity NPC64425
0.9268 High Similarity NPC186816
0.9268 High Similarity NPC12013
0.9268 High Similarity NPC189564
0.9268 High Similarity NPC476470
0.9268 High Similarity NPC203145
0.9268 High Similarity NPC11432
0.9268 High Similarity NPC256188
0.9264 High Similarity NPC257566
0.9264 High Similarity NPC124155
0.9259 High Similarity NPC303913
0.9255 High Similarity NPC138811
0.9255 High Similarity NPC473634
0.9255 High Similarity NPC22062
0.925 High Similarity NPC127406
0.925 High Similarity NPC206378
0.9235 High Similarity NPC470445
0.9235 High Similarity NPC470446
0.9235 High Similarity NPC470449
0.9235 High Similarity NPC470447
0.9231 High Similarity NPC473895
0.9226 High Similarity NPC122467
0.9226 High Similarity NPC255799
0.9226 High Similarity NPC292019
0.9226 High Similarity NPC472384
0.9226 High Similarity NPC48984
0.9226 High Similarity NPC471669
0.9226 High Similarity NPC14187
0.9226 High Similarity NPC202908
0.9226 High Similarity NPC473862
0.9226 High Similarity NPC89127
0.9226 High Similarity NPC472380
0.9226 High Similarity NPC472382
0.9222 High Similarity NPC25724
0.9222 High Similarity NPC204693
0.9217 High Similarity NPC183357
0.9217 High Similarity NPC209550
0.9217 High Similarity NPC22195
0.9217 High Similarity NPC277532
0.9217 High Similarity NPC175429
0.9217 High Similarity NPC44558
0.9217 High Similarity NPC76047
0.9217 High Similarity NPC21190
0.9217 High Similarity NPC138990
0.9212 High Similarity NPC93099
0.9207 High Similarity NPC289667
0.9207 High Similarity NPC7752
0.9207 High Similarity NPC292929
0.9207 High Similarity NPC76831
0.9202 High Similarity NPC472876
0.9202 High Similarity NPC244875
0.9202 High Similarity NPC44947
0.9198 High Similarity NPC473623
0.9193 High Similarity NPC65003
0.9193 High Similarity NPC44931
0.9193 High Similarity NPC129827
0.9193 High Similarity NPC473512
0.9193 High Similarity NPC43638
0.9193 High Similarity NPC60966
0.9187 High Similarity NPC26195
0.9187 High Similarity NPC97052
0.9187 High Similarity NPC169248
0.9187 High Similarity NPC39351
0.9187 High Similarity NPC72649
0.9181 High Similarity NPC249560
0.9181 High Similarity NPC275977
0.9181 High Similarity NPC223860
0.9176 High Similarity NPC470448
0.9176 High Similarity NPC470453
0.9176 High Similarity NPC469371
0.9176 High Similarity NPC164047
0.9176 High Similarity NPC470452
0.9172 High Similarity NPC173837
0.9172 High Similarity NPC251417
0.9172 High Similarity NPC476622
0.9172 High Similarity NPC476623
0.9172 High Similarity NPC476621
0.9172 High Similarity NPC476620
0.9172 High Similarity NPC89052
0.9172 High Similarity NPC476618
0.9172 High Similarity NPC476619
0.9162 High Similarity NPC211594
0.9162 High Similarity NPC470715
0.9162 High Similarity NPC259152
0.9162 High Similarity NPC172807
0.9162 High Similarity NPC475155
0.9162 High Similarity NPC474522
0.9162 High Similarity NPC47140
0.9162 High Similarity NPC67134
0.9162 High Similarity NPC3583
0.9162 High Similarity NPC470714
0.9162 High Similarity NPC254540
0.9162 High Similarity NPC470716
0.9157 High Similarity NPC112755
0.9157 High Similarity NPC209296
0.9157 High Similarity NPC5319
0.9157 High Similarity NPC471457
0.9157 High Similarity NPC170675
0.9157 High Similarity NPC61791
0.9157 High Similarity NPC95855
0.9157 High Similarity NPC86008
0.9157 High Similarity NPC195257
0.9157 High Similarity NPC210042
0.9152 High Similarity NPC8856
0.9152 High Similarity NPC236934
0.9152 High Similarity NPC115674
0.9152 High Similarity NPC210073
0.9152 High Similarity NPC5778
0.9146 High Similarity NPC29830
0.9141 High Similarity NPC47923
0.9136 High Similarity NPC308265
0.9136 High Similarity NPC43761
0.9136 High Similarity NPC73511
0.913 High Similarity NPC473657
0.913 High Similarity NPC261866
0.913 High Similarity NPC170475
0.913 High Similarity NPC295613
0.9128 High Similarity NPC33083
0.9128 High Similarity NPC473554
0.9128 High Similarity NPC470719
0.9128 High Similarity NPC295625
0.9125 High Similarity NPC260604
0.9125 High Similarity NPC106625
0.9125 High Similarity NPC299435
0.9123 High Similarity NPC162394
0.9123 High Similarity NPC241781
0.9123 High Similarity NPC156785
0.9118 High Similarity NPC241423
0.9118 High Similarity NPC192539
0.9118 High Similarity NPC470444
0.9118 High Similarity NPC245059
0.9118 High Similarity NPC110941
0.9118 High Similarity NPC470443
0.9118 High Similarity NPC473571
0.9118 High Similarity NPC84494
0.9118 High Similarity NPC126784
0.9118 High Similarity NPC473682
0.9112 High Similarity NPC219043
0.9112 High Similarity NPC231787
0.9112 High Similarity NPC470949
0.9112 High Similarity NPC169733
0.9112 High Similarity NPC65563
0.9112 High Similarity NPC268533
0.9107 High Similarity NPC208668
0.9102 High Similarity NPC470712

  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 NPC257011 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
0.9333 High Similarity NPD7074 Phase 3
0.9217 High Similarity NPD7472 Approved
0.9167 High Similarity NPD7808 Phase 3
0.9157 High Similarity NPD7804 Clinical (unspecified phase)
0.9157 High Similarity NPD7054 Approved
0.9107 High Similarity NPD7251 Discontinued
0.9074 High Similarity NPD4381 Clinical (unspecified phase)
0.9048 High Similarity NPD6797 Phase 2
0.8941 High Similarity NPD4338 Clinical (unspecified phase)
0.8647 High Similarity NPD3818 Discontinued
0.8639 High Similarity NPD6166 Phase 2
0.8639 High Similarity NPD6167 Clinical (unspecified phase)
0.8639 High Similarity NPD6168 Clinical (unspecified phase)
0.8614 High Similarity NPD7075 Discontinued
0.8555 High Similarity NPD6559 Discontinued
0.8539 High Similarity NPD7879 Clinical (unspecified phase)
0.8485 Intermediate Similarity NPD1934 Approved
0.8476 Intermediate Similarity NPD4380 Phase 2
0.8457 Intermediate Similarity NPD8312 Approved
0.8457 Intermediate Similarity NPD8313 Approved
0.8434 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD7819 Suspended
0.8391 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8383 Intermediate Similarity NPD5402 Approved
0.8333 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD2801 Approved
0.8274 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD3817 Phase 2
0.8263 Intermediate Similarity NPD6801 Discontinued
0.8214 Intermediate Similarity NPD8455 Phase 2
0.8204 Intermediate Similarity NPD7411 Suspended
0.8187 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8168 Intermediate Similarity NPD7783 Phase 2
0.8168 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.814 Intermediate Similarity NPD6959 Discontinued
0.8137 Intermediate Similarity NPD1549 Phase 2
0.811 Intermediate Similarity NPD6799 Approved
0.8103 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8081 Intermediate Similarity NPD5494 Approved
0.8072 Intermediate Similarity NPD5403 Approved
0.8068 Intermediate Similarity NPD5844 Phase 1
0.8063 Intermediate Similarity NPD8151 Discontinued
0.8061 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1511 Approved
0.7989 Intermediate Similarity NPD7435 Discontinued
0.7952 Intermediate Similarity NPD5401 Approved
0.7929 Intermediate Similarity NPD6599 Discontinued
0.7923 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD1653 Approved
0.791 Intermediate Similarity NPD7228 Approved
0.7907 Intermediate Similarity NPD3882 Suspended
0.7907 Intermediate Similarity NPD7768 Phase 2
0.7904 Intermediate Similarity NPD1512 Approved
0.7901 Intermediate Similarity NPD2796 Approved
0.7895 Intermediate Similarity NPD7698 Approved
0.7895 Intermediate Similarity NPD7696 Phase 3
0.7895 Intermediate Similarity NPD7697 Approved
0.7853 Intermediate Similarity NPD7473 Discontinued
0.7844 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD1510 Phase 2
0.7835 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7835 Intermediate Similarity NPD7874 Approved
0.7831 Intermediate Similarity NPD6781 Approved
0.7831 Intermediate Similarity NPD6782 Approved
0.7831 Intermediate Similarity NPD6778 Approved
0.7831 Intermediate Similarity NPD6780 Approved
0.7831 Intermediate Similarity NPD6777 Approved
0.7831 Intermediate Similarity NPD6776 Approved
0.7831 Intermediate Similarity NPD6779 Approved
0.7824 Intermediate Similarity NPD7701 Phase 2
0.7809 Intermediate Similarity NPD3751 Discontinued
0.7791 Intermediate Similarity NPD2935 Discontinued
0.7791 Intermediate Similarity NPD1465 Phase 2
0.7784 Intermediate Similarity NPD6232 Discontinued
0.7784 Intermediate Similarity NPD3787 Discontinued
0.776 Intermediate Similarity NPD7871 Phase 2
0.776 Intermediate Similarity NPD7870 Phase 2
0.7751 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD7685 Pre-registration
0.7727 Intermediate Similarity NPD7199 Phase 2
0.7725 Intermediate Similarity NPD7700 Phase 2
0.7725 Intermediate Similarity NPD7699 Phase 2
0.7711 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD3750 Approved
0.7711 Intermediate Similarity NPD4628 Phase 3
0.7702 Intermediate Similarity NPD1240 Approved
0.7697 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD7584 Approved
0.7668 Intermediate Similarity NPD8320 Phase 1
0.7668 Intermediate Similarity NPD8319 Approved
0.7663 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD3749 Approved
0.7656 Intermediate Similarity NPD6823 Phase 2
0.7637 Intermediate Similarity NPD7240 Approved
0.7636 Intermediate Similarity NPD7266 Discontinued
0.7614 Intermediate Similarity NPD7801 Approved
0.7607 Intermediate Similarity NPD1607 Approved
0.7579 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD1551 Phase 2
0.7566 Intermediate Similarity NPD6534 Approved
0.7566 Intermediate Similarity NPD6535 Approved
0.7558 Intermediate Similarity NPD7458 Discontinued
0.7545 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD2533 Approved
0.7529 Intermediate Similarity NPD2534 Approved
0.7529 Intermediate Similarity NPD37 Approved
0.7529 Intermediate Similarity NPD2532 Approved
0.7527 Intermediate Similarity NPD8434 Phase 2
0.7527 Intermediate Similarity NPD8150 Discontinued
0.7514 Intermediate Similarity NPD6234 Discontinued
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD4967 Phase 2
0.75 Intermediate Similarity NPD4965 Approved
0.7471 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD7585 Approved
0.7451 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD7583 Approved
0.741 Intermediate Similarity NPD3748 Approved
0.7391 Intermediate Similarity NPD5953 Discontinued
0.7378 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD1613 Approved
0.7377 Intermediate Similarity NPD7286 Phase 2
0.7356 Intermediate Similarity NPD3226 Approved
0.7346 Intermediate Similarity NPD6832 Phase 2
0.7341 Intermediate Similarity NPD920 Approved
0.7333 Intermediate Similarity NPD1933 Approved
0.733 Intermediate Similarity NPD6212 Phase 3
0.733 Intermediate Similarity NPD6213 Phase 3
0.733 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD919 Approved
0.7305 Intermediate Similarity NPD7033 Discontinued
0.7294 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6100 Approved
0.7262 Intermediate Similarity NPD6099 Approved
0.7251 Intermediate Similarity NPD6190 Approved
0.7241 Intermediate Similarity NPD7930 Approved
0.7238 Intermediate Similarity NPD1247 Approved
0.7235 Intermediate Similarity NPD1243 Approved
0.7235 Intermediate Similarity NPD2800 Approved
0.7232 Intermediate Similarity NPD6844 Discontinued
0.7229 Intermediate Similarity NPD230 Phase 1
0.7225 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2346 Discontinued
0.7213 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6233 Phase 2
0.7209 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD2799 Discontinued
0.7186 Intermediate Similarity NPD6651 Approved
0.7175 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD7680 Approved
0.7169 Intermediate Similarity NPD943 Approved
0.7168 Intermediate Similarity NPD7390 Discontinued
0.716 Intermediate Similarity NPD1203 Approved
0.7159 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD3926 Phase 2
0.7152 Intermediate Similarity NPD2313 Discontinued
0.7152 Intermediate Similarity NPD6798 Discontinued
0.7143 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7097 Phase 1
0.7135 Intermediate Similarity NPD1652 Phase 2
0.7134 Intermediate Similarity NPD4908 Phase 1
0.7134 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD5124 Phase 1
0.7126 Intermediate Similarity NPD6355 Discontinued
0.7126 Intermediate Similarity NPD447 Suspended
0.7125 Intermediate Similarity NPD1091 Approved
0.7113 Intermediate Similarity NPD4360 Phase 2
0.7113 Intermediate Similarity NPD4363 Phase 3
0.7109 Intermediate Similarity NPD8059 Phase 3
0.7109 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD5710 Approved
0.7104 Intermediate Similarity NPD5711 Approved
0.7091 Intermediate Similarity NPD3027 Phase 3
0.7073 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD3268 Approved
0.702 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD2344 Approved
0.7015 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD2798 Approved
0.7011 Intermediate Similarity NPD7229 Phase 3
0.6975 Remote Similarity NPD9717 Approved
0.6975 Remote Similarity NPD1608 Approved
0.697 Remote Similarity NPD2861 Phase 2
0.6957 Remote Similarity NPD8127 Discontinued
0.6951 Remote Similarity NPD2797 Approved
0.6936 Remote Similarity NPD6674 Discontinued
0.6914 Remote Similarity NPD422 Phase 1
0.6914 Remote Similarity NPD1610 Phase 2
0.6901 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6901 Remote Similarity NPD4308 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