Structure

Physi-Chem Properties

Molecular Weight:  800.18
Volume:  747.903
LogP:  2.181
LogD:  1.477
LogS:  -5.407
# Rotatable Bonds:  20
TPSA:  259.07
# H-Bond Aceptor:  20
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.145
Synthetic Accessibility Score:  4.661
Fsp3:  0.378
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.107
MDCK Permeability:  8.430313027929515e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.164
Human Intestinal Absorption (HIA):  0.948
20% Bioavailability (F20%):  0.082
30% Bioavailability (F30%):  0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.156
Plasma Protein Binding (PPB):  70.14058685302734%
Volume Distribution (VD):  0.491
Pgp-substrate:  18.465993881225586%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.003
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.167
CYP2C9-substrate:  0.105
CYP2D6-inhibitor:  0.797
CYP2D6-substrate:  0.073
CYP3A4-inhibitor:  0.242
CYP3A4-substrate:  0.144

ADMET: Excretion

Clearance (CL):  0.989
Half-life (T1/2):  0.887

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.532
Drug-inuced Liver Injury (DILI):  0.974
AMES Toxicity:  0.088
Rat Oral Acute Toxicity:  0.585
Maximum Recommended Daily Dose:  0.077
Skin Sensitization:  0.928
Carcinogencity:  0.036
Eye Corrosion:  0.003
Eye Irritation:  0.121
Respiratory Toxicity:  0.016

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

  Natural Product: NPC475214

Natural Product ID:  NPC475214
Common Name*:   Octa-O-Acetylhyperoside
IUPAC Name:   [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxochromen-3-yl]oxyoxan-2-yl]methyl acetate
Synonyms:   Octa-O-Acetylhyperoside; Quercetin-3-Galactoside Octaacetate
Standard InCHIKey:  TVRPKUGAMSRLJH-CHLLVNLZSA-N
Standard InCHI:  InChI=1S/C37H36O20/c1-15(38)47-14-29-33(52-20(6)43)35(53-21(7)44)36(54-22(8)45)37(56-29)57-34-31(46)30-27(51-19(5)42)12-24(48-16(2)39)13-28(30)55-32(34)23-9-10-25(49-17(3)40)26(11-23)50-18(4)41/h9-13,29,33,35-37H,14H2,1-8H3/t29-,33+,35+,36-,37+/m1/s1
SMILES:  CC(=O)OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(OC(=O)C)cc(c3)OC(=O)C)c2ccc(c(c2)OC(=O)C)OC(=O)C)[C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501162
PubChem CID:   14283880
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003531] Flavonoid-3-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
NPO28094 Consolida oliveriana Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[19489596]
NPO33118 Rhamnus Genus Rhamnaceae Eukaryota n.a. n.a. n.a. PMID[8350094]
NPO28094 Consolida oliveriana Species Ranunculaceae 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
NPT1597 Cell Line J774.2 IC50 = 122310.0 nM PMID[566406]
NPT1597 Cell Line J774.2 Ratio IC50 = 10.0 n.a. PMID[566406]
NPT20967 CELL-LINE Platelet n.a. Activity = 0.0 % PMID[566405]
NPT20967 CELL-LINE Platelet n.a. Activity = 78.5 % PMID[566405]
NPT20967 CELL-LINE Platelet n.a. MEC = 5.0 ug ml-1 PMID[566405]
NPT20967 CELL-LINE Platelet n.a. Activity = 100.0 ug ml-1 PMID[566405]
NPT1596 Organism Leishmania peruviana Leishmania peruviana IC50 = 7350.0 nM PMID[566406]
NPT1208 Organism Leishmania braziliensis Leishmania braziliensis IC50 = 6210.0 nM PMID[566406]
NPT1596 Organism Leishmania peruviana Leishmania peruviana Activity = 55.0 % PMID[566406]
NPT1208 Organism Leishmania braziliensis Leishmania braziliensis Activity = 46.0 % PMID[566406]
NPT1596 Organism Leishmania peruviana Leishmania peruviana Activity = 72.0 % PMID[566406]
NPT1208 Organism Leishmania braziliensis Leishmania braziliensis Activity = 60.0 % PMID[566406]
NPT1596 Organism Leishmania peruviana Leishmania peruviana Inhibition = 67.0 % PMID[566406]
NPT1596 Organism Leishmania peruviana Leishmania peruviana Inhibition = 30.0 % PMID[566406]

☑ 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 NPC475214 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
0.9873 High Similarity NPC476180
0.9811 High Similarity NPC475434
0.9808 High Similarity NPC414831
0.9551 High Similarity NPC117478
0.9503 High Similarity NPC477165
0.943 High Similarity NPC321478
0.9371 High Similarity NPC473516
0.9333 High Similarity NPC473862
0.9308 High Similarity NPC477164
0.9299 High Similarity NPC471746
0.9277 High Similarity NPC173837
0.9268 High Similarity NPC153755
0.9231 High Similarity NPC474388
0.9231 High Similarity NPC474170
0.9231 High Similarity NPC472535
0.9217 High Similarity NPC89127
0.9217 High Similarity NPC471669
0.9217 High Similarity NPC48984
0.9212 High Similarity NPC4390
0.9207 High Similarity NPC244776
0.9207 High Similarity NPC116864
0.9172 High Similarity NPC470713
0.9172 High Similarity NPC460984
0.9172 High Similarity NPC470717
0.9172 High Similarity NPC21359
0.9172 High Similarity NPC25946
0.9172 High Similarity NPC470720
0.9172 High Similarity NPC470451
0.9172 High Similarity NPC470455
0.9167 High Similarity NPC177839
0.9162 High Similarity NPC251417
0.9162 High Similarity NPC89052
0.9162 High Similarity NPC477895
0.9157 High Similarity NPC294815
0.9157 High Similarity NPC264735
0.9157 High Similarity NPC16194
0.9157 High Similarity NPC220173
0.9157 High Similarity NPC19108
0.9157 High Similarity NPC476472
0.9157 High Similarity NPC473327
0.9152 High Similarity NPC190003
0.9152 High Similarity NPC175107
0.9146 High Similarity NPC120099
0.9146 High Similarity NPC219904
0.9146 High Similarity NPC223747
0.9146 High Similarity NPC225434
0.9146 High Similarity NPC203050
0.913 High Similarity NPC182045
0.9119 High Similarity NPC257277
0.9118 High Similarity NPC473554
0.9118 High Similarity NPC474093
0.9118 High Similarity NPC295625
0.9118 High Similarity NPC470719
0.9118 High Similarity NPC104910
0.9112 High Similarity NPC470718
0.9112 High Similarity NPC241781
0.9112 High Similarity NPC470447
0.9112 High Similarity NPC162394
0.9112 High Similarity NPC470445
0.9112 High Similarity NPC470449
0.9112 High Similarity NPC156785
0.9112 High Similarity NPC470446
0.9107 High Similarity NPC192539
0.9102 High Similarity NPC472385
0.9102 High Similarity NPC198324
0.9102 High Similarity NPC292019
0.9102 High Similarity NPC202908
0.9102 High Similarity NPC219043
0.9102 High Similarity NPC14187
0.9102 High Similarity NPC122467
0.9091 High Similarity NPC206123
0.9091 High Similarity NPC20505
0.9091 High Similarity NPC155763
0.9091 High Similarity NPC235260
0.9085 High Similarity NPC52550
0.9085 High Similarity NPC226304
0.9085 High Similarity NPC173637
0.9085 High Similarity NPC84362
0.9085 High Similarity NPC325555
0.9085 High Similarity NPC265530
0.9085 High Similarity NPC127546
0.9085 High Similarity NPC223424
0.9085 High Similarity NPC317489
0.908 High Similarity NPC15358
0.908 High Similarity NPC475366
0.908 High Similarity NPC475497
0.908 High Similarity NPC284277
0.9068 High Similarity NPC110349
0.9064 High Similarity NPC475179
0.9059 High Similarity NPC275977
0.9059 High Similarity NPC223860
0.9059 High Similarity NPC249560
0.9057 High Similarity NPC276059
0.9057 High Similarity NPC241774
0.9057 High Similarity NPC122623
0.9057 High Similarity NPC284353
0.9057 High Similarity NPC34725
0.9048 High Similarity NPC217520
0.9048 High Similarity NPC139571
0.9048 High Similarity NPC120952
0.9042 High Similarity NPC477848
0.9042 High Similarity NPC253685
0.9042 High Similarity NPC237435
0.9042 High Similarity NPC49344
0.9042 High Similarity NPC135277
0.9042 High Similarity NPC115760
0.9042 High Similarity NPC43211
0.9042 High Similarity NPC101191
0.9042 High Similarity NPC210094
0.9036 High Similarity NPC155877
0.9036 High Similarity NPC134532
0.9036 High Similarity NPC60735
0.9036 High Similarity NPC33054
0.9036 High Similarity NPC26230
0.9036 High Similarity NPC471725
0.9036 High Similarity NPC203259
0.9036 High Similarity NPC176740
0.9036 High Similarity NPC471748
0.903 High Similarity NPC138927
0.9024 High Similarity NPC253662
0.9024 High Similarity NPC56077
0.9024 High Similarity NPC88789
0.9024 High Similarity NPC113968
0.9024 High Similarity NPC118284
0.9024 High Similarity NPC308404
0.9024 High Similarity NPC277174
0.9024 High Similarity NPC73855
0.9024 High Similarity NPC197285
0.9024 High Similarity NPC145038
0.9024 High Similarity NPC135599
0.9024 High Similarity NPC276222
0.9024 High Similarity NPC281131
0.9024 High Similarity NPC179950
0.9024 High Similarity NPC21100
0.9024 High Similarity NPC328940
0.9024 High Similarity NPC274618
0.9018 High Similarity NPC88023
0.9018 High Similarity NPC309025
0.9018 High Similarity NPC243930
0.9006 High Similarity NPC104677
0.9006 High Similarity NPC257914
0.9006 High Similarity NPC238405
0.9006 High Similarity NPC33083
0.9006 High Similarity NPC104459
0.8994 High Similarity NPC470443
0.8994 High Similarity NPC279930
0.8994 High Similarity NPC126784
0.8994 High Similarity NPC241423
0.8994 High Similarity NPC110941
0.8994 High Similarity NPC473571
0.8994 High Similarity NPC470444
0.8994 High Similarity NPC473682
0.8988 High Similarity NPC211532
0.8988 High Similarity NPC472384
0.8988 High Similarity NPC472382
0.8988 High Similarity NPC233994
0.8988 High Similarity NPC472380
0.8982 High Similarity NPC21666
0.8982 High Similarity NPC169977
0.8982 High Similarity NPC101026
0.8982 High Similarity NPC42773
0.8982 High Similarity NPC24043
0.8982 High Similarity NPC45522
0.8976 High Similarity NPC156869
0.8976 High Similarity NPC67105
0.8976 High Similarity NPC95866
0.8976 High Similarity NPC259896
0.8976 High Similarity NPC136042
0.8976 High Similarity NPC285197
0.8976 High Similarity NPC29958
0.8976 High Similarity NPC254855
0.8976 High Similarity NPC255157
0.8976 High Similarity NPC67326
0.8963 High Similarity NPC22832
0.8963 High Similarity NPC19388
0.8963 High Similarity NPC55786
0.8963 High Similarity NPC311830
0.8963 High Similarity NPC277205
0.8963 High Similarity NPC240431
0.8953 High Similarity NPC30011
0.8953 High Similarity NPC72554
0.8953 High Similarity NPC97817
0.8947 High Similarity NPC470416
0.8935 High Similarity NPC258044
0.8935 High Similarity NPC37668
0.8935 High Similarity NPC113836
0.8935 High Similarity NPC267680
0.8935 High Similarity NPC35167
0.8935 High Similarity NPC217387
0.8935 High Similarity NPC253521
0.8935 High Similarity NPC293626
0.8935 High Similarity NPC196127
0.8929 High Similarity NPC214621
0.8929 High Similarity NPC198199
0.8929 High Similarity NPC223426
0.8929 High Similarity NPC81042
0.8929 High Similarity NPC34267
0.8922 High Similarity NPC254540
0.8922 High Similarity NPC476405
0.8922 High Similarity NPC245452

  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 NPC475214 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
0.9273 High Similarity NPD7808 Phase 3
0.9096 High Similarity NPD7251 Discontinued
0.9057 High Similarity NPD3817 Phase 2
0.9042 High Similarity NPD4338 Clinical (unspecified phase)
0.9036 High Similarity NPD6797 Phase 2
0.8976 High Similarity NPD7472 Approved
0.8916 High Similarity NPD7054 Approved
0.875 High Similarity NPD7074 Phase 3
0.869 High Similarity NPD7804 Clinical (unspecified phase)
0.8521 High Similarity NPD3818 Discontinued
0.8485 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD6166 Phase 2
0.8373 Intermediate Similarity NPD7075 Discontinued
0.8354 Intermediate Similarity NPD1934 Approved
0.8323 Intermediate Similarity NPD919 Approved
0.8313 Intermediate Similarity NPD6799 Approved
0.8274 Intermediate Similarity NPD5494 Approved
0.8272 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8253 Intermediate Similarity NPD5402 Approved
0.8242 Intermediate Similarity NPD6801 Discontinued
0.8204 Intermediate Similarity NPD3882 Suspended
0.8193 Intermediate Similarity NPD2801 Approved
0.8193 Intermediate Similarity NPD7819 Suspended
0.8193 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD5403 Approved
0.8148 Intermediate Similarity NPD5401 Approved
0.8101 Intermediate Similarity NPD2796 Approved
0.8098 Intermediate Similarity NPD1512 Approved
0.8095 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8057 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD6599 Discontinued
0.7975 Intermediate Similarity NPD1511 Approved
0.7962 Intermediate Similarity NPD1933 Approved
0.7943 Intermediate Similarity NPD5844 Phase 1
0.7927 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7912 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD6559 Discontinued
0.7907 Intermediate Similarity NPD1247 Approved
0.7904 Intermediate Similarity NPD4380 Phase 2
0.7857 Intermediate Similarity NPD7411 Suspended
0.7829 Intermediate Similarity NPD7473 Discontinued
0.7824 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD3926 Phase 2
0.7784 Intermediate Similarity NPD1653 Approved
0.7771 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD6232 Discontinued
0.7716 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD7685 Pre-registration
0.7701 Intermediate Similarity NPD7199 Phase 2
0.7669 Intermediate Similarity NPD1549 Phase 2
0.7661 Intermediate Similarity NPD1465 Phase 2
0.7657 Intermediate Similarity NPD3787 Discontinued
0.7643 Intermediate Similarity NPD6832 Phase 2
0.7637 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD8313 Approved
0.7624 Intermediate Similarity NPD8312 Approved
0.7619 Intermediate Similarity NPD920 Approved
0.7609 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD3748 Approved
0.7584 Intermediate Similarity NPD3751 Discontinued
0.7571 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD8455 Phase 2
0.7547 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD1243 Approved
0.75 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD37 Approved
0.75 Intermediate Similarity NPD6959 Discontinued
0.7486 Intermediate Similarity NPD7228 Approved
0.7485 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1510 Phase 2
0.7471 Intermediate Similarity NPD4965 Approved
0.7471 Intermediate Similarity NPD4966 Approved
0.7471 Intermediate Similarity NPD4967 Phase 2
0.7471 Intermediate Similarity NPD7768 Phase 2
0.7455 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7418 Intermediate Similarity NPD7240 Approved
0.7414 Intermediate Similarity NPD5353 Approved
0.7409 Intermediate Similarity NPD7435 Discontinued
0.7407 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD447 Suspended
0.7398 Intermediate Similarity NPD8151 Discontinued
0.7386 Intermediate Similarity NPD6234 Discontinued
0.7368 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD3750 Approved
0.733 Intermediate Similarity NPD3749 Approved
0.7289 Intermediate Similarity NPD7266 Discontinued
0.7273 Intermediate Similarity NPD7874 Approved
0.7273 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD6385 Approved
0.7241 Intermediate Similarity NPD6386 Approved
0.7239 Intermediate Similarity NPD1240 Approved
0.7236 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD7783 Phase 2
0.7231 Intermediate Similarity NPD7697 Approved
0.7231 Intermediate Similarity NPD7696 Phase 3
0.7231 Intermediate Similarity NPD7698 Approved
0.7229 Intermediate Similarity NPD1551 Phase 2
0.7222 Intermediate Similarity NPD5242 Approved
0.7219 Intermediate Similarity NPD8434 Phase 2
0.7219 Intermediate Similarity NPD6190 Approved
0.7208 Intermediate Similarity NPD7584 Approved
0.7202 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD7871 Phase 2
0.7194 Intermediate Similarity NPD7870 Phase 2
0.7179 Intermediate Similarity NPD5006 Approved
0.7179 Intermediate Similarity NPD5005 Approved
0.7165 Intermediate Similarity NPD6777 Approved
0.7165 Intermediate Similarity NPD6782 Approved
0.7165 Intermediate Similarity NPD6776 Approved
0.7165 Intermediate Similarity NPD6780 Approved
0.7165 Intermediate Similarity NPD6779 Approved
0.7165 Intermediate Similarity NPD6778 Approved
0.7165 Intermediate Similarity NPD6781 Approved
0.716 Intermediate Similarity NPD4628 Phase 3
0.7152 Intermediate Similarity NPD1607 Approved
0.7126 Intermediate Similarity NPD2935 Discontinued
0.7126 Intermediate Similarity NPD7458 Discontinued
0.7126 Intermediate Similarity NPD3226 Approved
0.7121 Intermediate Similarity NPD7583 Approved
0.7118 Intermediate Similarity NPD3887 Approved
0.7117 Intermediate Similarity NPD6798 Discontinued
0.7111 Intermediate Similarity NPD8127 Discontinued
0.7107 Intermediate Similarity NPD8320 Phase 1
0.7107 Intermediate Similarity NPD8319 Approved
0.7093 Intermediate Similarity NPD2533 Approved
0.7093 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD2532 Approved
0.7093 Intermediate Similarity NPD3146 Approved
0.7093 Intermediate Similarity NPD2534 Approved
0.7091 Intermediate Similarity NPD6355 Discontinued
0.7091 Intermediate Similarity NPD230 Phase 1
0.7089 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD7585 Approved
0.7085 Intermediate Similarity NPD7701 Phase 2
0.7073 Intermediate Similarity NPD6233 Phase 2
0.7062 Intermediate Similarity NPD4420 Approved
0.7037 Intermediate Similarity NPD8150 Discontinued
0.703 Intermediate Similarity NPD1613 Approved
0.703 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD8285 Discontinued
0.7019 Intermediate Similarity NPD3267 Approved
0.7019 Intermediate Similarity NPD3266 Approved
0.7012 Intermediate Similarity NPD2313 Discontinued
0.7 Intermediate Similarity NPD1652 Phase 2
0.6995 Remote Similarity NPD2403 Approved
0.6994 Remote Similarity NPD7004 Clinical (unspecified phase)
0.699 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6989 Remote Similarity NPD5953 Discontinued
0.6982 Remote Similarity NPD2346 Discontinued
0.698 Remote Similarity NPD7801 Approved
0.6975 Remote Similarity NPD2798 Approved
0.6975 Remote Similarity NPD1019 Discontinued
0.6974 Remote Similarity NPD7700 Phase 2
0.6974 Remote Similarity NPD7699 Phase 2
0.6973 Remote Similarity NPD7286 Phase 2
0.6964 Remote Similarity NPD2799 Discontinued
0.6964 Remote Similarity NPD7033 Discontinued
0.6928 Remote Similarity NPD943 Approved
0.6928 Remote Similarity NPD4307 Phase 2
0.6923 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1203 Approved
0.691 Remote Similarity NPD6844 Discontinued
0.6909 Remote Similarity NPD1296 Phase 2
0.6909 Remote Similarity NPD3268 Approved
0.6907 Remote Similarity NPD6534 Approved
0.6907 Remote Similarity NPD6535 Approved
0.6906 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6901 Remote Similarity NPD6674 Discontinued
0.689 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6886 Remote Similarity NPD5124 Phase 1
0.6886 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6882 Remote Similarity NPD2353 Approved
0.6882 Remote Similarity NPD2355 Clinical (unspecified phase)
0.686 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6857 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6855 Remote Similarity NPD17 Approved
0.6854 Remote Similarity NPD5889 Approved
0.6854 Remote Similarity NPD5890 Approved
0.6854 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6852 Remote Similarity NPD3225 Approved
0.6848 Remote Similarity NPD3027 Phase 3
0.6836 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6834 Remote Similarity NPD6823 Phase 2
0.6832 Remote Similarity NPD9717 Approved
0.6829 Remote Similarity NPD3018 Phase 2
0.6829 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6828 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6825 Remote Similarity NPD7549 Discontinued
0.6824 Remote Similarity NPD6100 Approved
0.6824 Remote Similarity NPD6099 Approved
0.681 Remote Similarity NPD2797 Approved
0.6805 Remote Similarity NPD7097 Phase 1

  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