Structure

Physi-Chem Properties

Molecular Weight:  1050.29
Volume:  956.078
LogP:  0.025
LogD:  -0.14
LogS:  -3.558
# Rotatable Bonds:  15
TPSA:  433.8
# H-Bond Aceptor:  27
# H-Bond Donor:  15
# Rings:  8
# Heavy Atoms:  27

MedChem Properties

QED Drug-Likeness Score:  0.033
Synthetic Accessibility Score:  6.26
Fsp3:  0.489
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.717
MDCK Permeability:  4.307888593757525e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.992
20% Bioavailability (F20%):  0.065
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.163
Plasma Protein Binding (PPB):  92.6612777709961%
Volume Distribution (VD):  0.298
Pgp-substrate:  13.073793411254883%

ADMET: Metabolism

CYP1A2-inhibitor:  0.022
CYP1A2-substrate:  0.005
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.037
CYP2C9-inhibitor:  0.012
CYP2C9-substrate:  0.048
CYP2D6-inhibitor:  0.027
CYP2D6-substrate:  0.088
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  0.149
Half-life (T1/2):  0.755

ADMET: Toxicity

hERG Blockers:  0.273
Human Hepatotoxicity (H-HT):  0.099
Drug-inuced Liver Injury (DILI):  0.986
AMES Toxicity:  0.419
Rat Oral Acute Toxicity:  0.025
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.949
Carcinogencity:  0.05
Eye Corrosion:  0.003
Eye Irritation:  0.029
Respiratory Toxicity:  0.005

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

  Natural Product: NPC33083

Natural Product ID:  NPC33083
Common Name*:   Camelliquercetiside A
IUPAC Name:   [(2S,3R,4S,5R,6R)-6-[[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:   Camelliquercetiside A
Standard InCHIKey:  YDPDTPHAIHAETR-RJHHWURMSA-N
Standard InCHI:  InChI=1S/C47H54O27/c1-16-30(56)40(72-46-37(63)35(61)32(58)26(13-48)69-46)38(64)45(67-16)66-15-27-33(59)41(73-44-36(62)31(57)24(54)14-65-44)43(71-28(55)9-4-17-2-6-19(49)7-3-17)47(70-27)74-42-34(60)29-23(53)11-20(50)12-25(29)68-39(42)18-5-8-21(51)22(52)10-18/h2-12,16,24,26-27,30-33,35-38,40-41,43-54,56-59,61-64H,13-15H2,1H3/b9-4+/t16-,24-,26+,27+,30-,31-,32+,33+,35-,36+,37+,38+,40+,41-,43+,44-,45+,46-,47-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)O)O)O)O)OC(=O)/C=C/c2ccc(cc2)O)O[C@H]2[C@@H]([C@H]([C@H](CO2)O)O)O)O)O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1957046
PubChem CID:   57401809
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
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.foodchem.2013.08.121]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Flowers n.a. n.a. PMID[16180814]
NPO8258 Camellia sinensis Species Theaceae Eukaryota seeds Shizuoka prefecture, Japan n.a. PMID[16499314]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[18068204]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[21434603]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. flower n.a. PMID[21922925]
NPO8258 Camellia sinensis Species Theaceae Eukaryota flower buds n.a. n.a. PMID[21925888]
NPO8258 Camellia sinensis Species Theaceae Eukaryota leaves n.a. n.a. PMID[22377672]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. leaf n.a. PMID[23265489]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaves Bandung, West Java, Indonesia PMID[23621359]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Cotyledon n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8258 Camellia sinensis Species Theaceae 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
NPT2 Others Unspecified IC50 = 17300.0 nM PMID[463120]
NPT1 Others Radical scavenging activity IC50 = 19800.0 nM PMID[463120]

☑ 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 NPC33083 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
0.9941 High Similarity NPC275977
0.9941 High Similarity NPC249560
0.9941 High Similarity NPC223860
0.9882 High Similarity NPC241781
0.9882 High Similarity NPC295625
0.9882 High Similarity NPC473554
0.9882 High Similarity NPC470719
0.9882 High Similarity NPC162394
0.9882 High Similarity NPC156785
0.9825 High Similarity NPC30011
0.9825 High Similarity NPC72554
0.9825 High Similarity NPC97817
0.9824 High Similarity NPC21359
0.9824 High Similarity NPC470717
0.9824 High Similarity NPC470713
0.9824 High Similarity NPC25946
0.9824 High Similarity NPC460984
0.9824 High Similarity NPC470720
0.9765 High Similarity NPC470718
0.9651 High Similarity NPC104910
0.9651 High Similarity NPC474093
0.9647 High Similarity NPC192539
0.9645 High Similarity NPC14187
0.9645 High Similarity NPC471669
0.9645 High Similarity NPC473862
0.9645 High Similarity NPC292019
0.9645 High Similarity NPC122467
0.9645 High Similarity NPC202908
0.9645 High Similarity NPC89127
0.9595 High Similarity NPC475179
0.9588 High Similarity NPC120952
0.9588 High Similarity NPC477895
0.9588 High Similarity NPC113836
0.9588 High Similarity NPC139571
0.9588 High Similarity NPC253521
0.9588 High Similarity NPC293626
0.9588 High Similarity NPC217520
0.9588 High Similarity NPC217387
0.9588 High Similarity NPC196127
0.9588 High Similarity NPC37668
0.9588 High Similarity NPC173837
0.9588 High Similarity NPC89052
0.9588 High Similarity NPC258044
0.9588 High Similarity NPC267680
0.9588 High Similarity NPC35167
0.9588 High Similarity NPC251417
0.9586 High Similarity NPC214621
0.9586 High Similarity NPC223426
0.9586 High Similarity NPC81042
0.9586 High Similarity NPC34267
0.9535 High Similarity NPC97119
0.9535 High Similarity NPC135831
0.9535 High Similarity NPC297503
0.9529 High Similarity NPC219043
0.9529 High Similarity NPC61904
0.9529 High Similarity NPC48984
0.9529 High Similarity NPC144097
0.948 High Similarity NPC470455
0.948 High Similarity NPC470451
0.948 High Similarity NPC470416
0.9471 High Similarity NPC294815
0.9471 High Similarity NPC473327
0.9471 High Similarity NPC253685
0.9471 High Similarity NPC220173
0.9471 High Similarity NPC19108
0.9471 High Similarity NPC16194
0.9471 High Similarity NPC198199
0.9471 High Similarity NPC476472
0.9467 High Similarity NPC134532
0.9467 High Similarity NPC203259
0.9467 High Similarity NPC33054
0.9467 High Similarity NPC471748
0.9467 High Similarity NPC176740
0.9467 High Similarity NPC470716
0.9467 High Similarity NPC474522
0.9467 High Similarity NPC470714
0.9467 High Similarity NPC471725
0.9467 High Similarity NPC470715
0.9467 High Similarity NPC155877
0.9422 High Similarity NPC470446
0.9422 High Similarity NPC470449
0.9422 High Similarity NPC470447
0.9422 High Similarity NPC36138
0.9422 High Similarity NPC199172
0.9422 High Similarity NPC470445
0.9422 High Similarity NPC35924
0.9419 High Similarity NPC471030
0.9415 High Similarity NPC231787
0.9412 High Similarity NPC472993
0.9408 High Similarity NPC164704
0.9408 High Similarity NPC67326
0.9408 High Similarity NPC255157
0.9408 High Similarity NPC470712
0.9408 High Similarity NPC244776
0.9408 High Similarity NPC67105
0.9408 High Similarity NPC156869
0.9408 High Similarity NPC254855
0.9408 High Similarity NPC136042
0.9408 High Similarity NPC29958
0.9408 High Similarity NPC116864
0.9408 High Similarity NPC95866
0.9408 High Similarity NPC259896
0.9371 High Similarity NPC64755
0.9364 High Similarity NPC469371
0.9353 High Similarity NPC67134
0.9353 High Similarity NPC180918
0.9353 High Similarity NPC26230
0.9353 High Similarity NPC60735
0.9353 High Similarity NPC190003
0.9353 High Similarity NPC153755
0.9353 High Similarity NPC175107
0.9353 High Similarity NPC47140
0.9349 High Similarity NPC227508
0.9306 High Similarity NPC473682
0.9306 High Similarity NPC470443
0.9306 High Similarity NPC126784
0.9306 High Similarity NPC110941
0.9306 High Similarity NPC241423
0.9306 High Similarity NPC473571
0.9306 High Similarity NPC470444
0.9302 High Similarity NPC296018
0.9302 High Similarity NPC154741
0.9302 High Similarity NPC470949
0.9302 High Similarity NPC65563
0.9298 High Similarity NPC175230
0.9298 High Similarity NPC172033
0.9298 High Similarity NPC88560
0.9298 High Similarity NPC4390
0.9294 High Similarity NPC285197
0.9294 High Similarity NPC155763
0.9294 High Similarity NPC206123
0.9294 High Similarity NPC20505
0.9294 High Similarity NPC235260
0.929 High Similarity NPC52550
0.929 High Similarity NPC317489
0.929 High Similarity NPC127546
0.929 High Similarity NPC223424
0.929 High Similarity NPC84362
0.929 High Similarity NPC173637
0.929 High Similarity NPC275454
0.9249 High Similarity NPC476773
0.9244 High Similarity NPC294629
0.924 High Similarity NPC11847
0.924 High Similarity NPC101399
0.924 High Similarity NPC217822
0.924 High Similarity NPC221288
0.9235 High Similarity NPC43587
0.9235 High Similarity NPC270578
0.9235 High Similarity NPC225434
0.9235 High Similarity NPC138927
0.9235 High Similarity NPC86008
0.9235 High Similarity NPC52382
0.9235 High Similarity NPC209296
0.9235 High Similarity NPC195257
0.9235 High Similarity NPC219904
0.9235 High Similarity NPC203050
0.9235 High Similarity NPC120099
0.9235 High Similarity NPC105283
0.9235 High Similarity NPC223747
0.9231 High Similarity NPC186816
0.9231 High Similarity NPC210073
0.9231 High Similarity NPC262222
0.9231 High Similarity NPC115674
0.9231 High Similarity NPC68592
0.9231 High Similarity NPC308404
0.9231 High Similarity NPC476470
0.9231 High Similarity NPC113968
0.9231 High Similarity NPC118284
0.9231 High Similarity NPC179950
0.9231 High Similarity NPC277174
0.9231 High Similarity NPC256188
0.9231 High Similarity NPC73855
0.9231 High Similarity NPC145038
0.9231 High Similarity NPC56077
0.9231 High Similarity NPC8856
0.9231 High Similarity NPC189564
0.9231 High Similarity NPC298666
0.9231 High Similarity NPC276222
0.9231 High Similarity NPC88789
0.9231 High Similarity NPC11432
0.9231 High Similarity NPC274618
0.9231 High Similarity NPC135599
0.9231 High Similarity NPC12013
0.9231 High Similarity NPC328940
0.9231 High Similarity NPC281131
0.9231 High Similarity NPC32641
0.9231 High Similarity NPC253662
0.9231 High Similarity NPC203145
0.9231 High Similarity NPC221342
0.9231 High Similarity NPC142142
0.9231 High Similarity NPC477613
0.9231 High Similarity NPC64425
0.92 High Similarity NPC473072
0.9191 High Similarity NPC472992
0.9191 High Similarity NPC255799
0.9191 High Similarity NPC169733
0.9191 High Similarity NPC198324
0.9191 High Similarity NPC8573
0.9191 High Similarity NPC472385
0.9191 High Similarity NPC472991

  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 NPC33083 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
0.9527 High Similarity NPD7251 Discontinued
0.9471 High Similarity NPD7808 Phase 3
0.9467 High Similarity NPD6797 Phase 2
0.9294 High Similarity NPD7472 Approved
0.9235 High Similarity NPD7054 Approved
0.9181 High Similarity NPD7074 Phase 3
0.9133 High Similarity NPD4338 Clinical (unspecified phase)
0.9012 High Similarity NPD7804 Clinical (unspecified phase)
0.8947 High Similarity NPD6166 Phase 2
0.8947 High Similarity NPD6168 Clinical (unspecified phase)
0.8947 High Similarity NPD6167 Clinical (unspecified phase)
0.88 High Similarity NPD7993 Clinical (unspecified phase)
0.8736 High Similarity NPD3818 Discontinued
0.8706 High Similarity NPD4381 Clinical (unspecified phase)
0.8588 High Similarity NPD3817 Phase 2
0.8538 High Similarity NPD4868 Clinical (unspecified phase)
0.8488 Intermediate Similarity NPD7075 Discontinued
0.8363 Intermediate Similarity NPD1934 Approved
0.8324 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8324 Intermediate Similarity NPD3882 Suspended
0.8314 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8314 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8266 Intermediate Similarity NPD5402 Approved
0.8256 Intermediate Similarity NPD6801 Discontinued
0.8242 Intermediate Similarity NPD8312 Approved
0.8242 Intermediate Similarity NPD8313 Approved
0.8232 Intermediate Similarity NPD6559 Discontinued
0.8225 Intermediate Similarity NPD1512 Approved
0.8208 Intermediate Similarity NPD2801 Approved
0.8176 Intermediate Similarity NPD5403 Approved
0.814 Intermediate Similarity NPD4380 Phase 2
0.8107 Intermediate Similarity NPD1511 Approved
0.8107 Intermediate Similarity NPD6799 Approved
0.8059 Intermediate Similarity NPD5401 Approved
0.8 Intermediate Similarity NPD7819 Suspended
0.7989 Intermediate Similarity NPD7411 Suspended
0.797 Intermediate Similarity NPD8151 Discontinued
0.7967 Intermediate Similarity NPD5844 Phase 1
0.7955 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD7685 Pre-registration
0.7926 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD1653 Approved
0.7912 Intermediate Similarity NPD7228 Approved
0.7912 Intermediate Similarity NPD3751 Discontinued
0.7901 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD8455 Phase 2
0.7861 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD7473 Discontinued
0.7849 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7845 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD6959 Discontinued
0.7829 Intermediate Similarity NPD6599 Discontinued
0.7806 Intermediate Similarity NPD7435 Discontinued
0.78 Intermediate Similarity NPD7783 Phase 2
0.78 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD1465 Phase 2
0.779 Intermediate Similarity NPD6232 Discontinued
0.779 Intermediate Similarity NPD3787 Discontinued
0.7778 Intermediate Similarity NPD5494 Approved
0.7772 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD7266 Discontinued
0.7746 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD7199 Phase 2
0.7709 Intermediate Similarity NPD7768 Phase 2
0.7706 Intermediate Similarity NPD1549 Phase 2
0.7677 Intermediate Similarity NPD8320 Phase 1
0.7677 Intermediate Similarity NPD8319 Approved
0.7674 Intermediate Similarity NPD6190 Approved
0.7662 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD7874 Approved
0.7647 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7626 Intermediate Similarity NPD7696 Phase 3
0.7626 Intermediate Similarity NPD7697 Approved
0.7626 Intermediate Similarity NPD7698 Approved
0.7624 Intermediate Similarity NPD919 Approved
0.7588 Intermediate Similarity NPD2796 Approved
0.7588 Intermediate Similarity NPD7871 Phase 2
0.7588 Intermediate Similarity NPD7870 Phase 2
0.7563 Intermediate Similarity NPD6782 Approved
0.7563 Intermediate Similarity NPD6776 Approved
0.7563 Intermediate Similarity NPD6778 Approved
0.7563 Intermediate Similarity NPD6777 Approved
0.7563 Intermediate Similarity NPD6781 Approved
0.7563 Intermediate Similarity NPD6780 Approved
0.7563 Intermediate Similarity NPD6779 Approved
0.7562 Intermediate Similarity NPD7701 Phase 2
0.7553 Intermediate Similarity NPD7240 Approved
0.7529 Intermediate Similarity NPD1510 Phase 2
0.7527 Intermediate Similarity NPD6234 Discontinued
0.7514 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD3749 Approved
0.7462 Intermediate Similarity NPD7700 Phase 2
0.7462 Intermediate Similarity NPD7699 Phase 2
0.7448 Intermediate Similarity NPD8150 Discontinued
0.7444 Intermediate Similarity NPD37 Approved
0.7426 Intermediate Similarity NPD7584 Approved
0.7418 Intermediate Similarity NPD4965 Approved
0.7418 Intermediate Similarity NPD4967 Phase 2
0.7418 Intermediate Similarity NPD4966 Approved
0.7414 Intermediate Similarity NPD3750 Approved
0.7399 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD3926 Phase 2
0.7366 Intermediate Similarity NPD7801 Approved
0.7358 Intermediate Similarity NPD8434 Phase 2
0.7356 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD230 Phase 1
0.7353 Intermediate Similarity NPD1933 Approved
0.7351 Intermediate Similarity NPD1247 Approved
0.7326 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD4628 Phase 3
0.731 Intermediate Similarity NPD6534 Approved
0.731 Intermediate Similarity NPD6535 Approved
0.7294 Intermediate Similarity NPD1613 Approved
0.7294 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD1240 Approved
0.7283 Intermediate Similarity NPD1551 Phase 2
0.7278 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7458 Discontinued
0.7277 Intermediate Similarity NPD7680 Approved
0.7228 Intermediate Similarity NPD6823 Phase 2
0.722 Intermediate Similarity NPD7585 Approved
0.7209 Intermediate Similarity NPD1607 Approved
0.7193 Intermediate Similarity NPD943 Approved
0.7184 Intermediate Similarity NPD2935 Discontinued
0.7176 Intermediate Similarity NPD6798 Discontinued
0.7171 Intermediate Similarity NPD7583 Approved
0.7164 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD447 Suspended
0.7135 Intermediate Similarity NPD6233 Phase 2
0.7126 Intermediate Similarity NPD3748 Approved
0.7088 Intermediate Similarity NPD3226 Approved
0.7072 Intermediate Similarity NPD920 Approved
0.707 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6832 Phase 2
0.7059 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD2532 Approved
0.7056 Intermediate Similarity NPD2534 Approved
0.7056 Intermediate Similarity NPD2533 Approved
0.7047 Intermediate Similarity NPD5953 Discontinued
0.7031 Intermediate Similarity NPD7286 Phase 2
0.7029 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD3027 Phase 3
0.7 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.6995 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6984 Remote Similarity NPD8127 Discontinued
0.6966 Remote Similarity NPD1243 Approved
0.6961 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6961 Remote Similarity NPD642 Clinical (unspecified phase)
0.6954 Remote Similarity NPD6355 Discontinued
0.6944 Remote Similarity NPD643 Clinical (unspecified phase)
0.6932 Remote Similarity NPD7033 Discontinued
0.6927 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6915 Remote Similarity NPD6212 Phase 3
0.6915 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6915 Remote Similarity NPD6213 Phase 3
0.6906 Remote Similarity NPD7390 Discontinued
0.6898 Remote Similarity NPD5353 Approved
0.6888 Remote Similarity NPD7549 Discontinued
0.6882 Remote Similarity NPD6844 Discontinued
0.6882 Remote Similarity NPD1203 Approved
0.6879 Remote Similarity NPD2313 Discontinued
0.6872 Remote Similarity NPD1652 Phase 2
0.6872 Remote Similarity NPD6674 Discontinued
0.686 Remote Similarity NPD4908 Phase 1
0.6857 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6854 Remote Similarity NPD7930 Approved
0.6854 Remote Similarity NPD2346 Discontinued
0.6837 Remote Similarity NPD7039 Approved
0.6837 Remote Similarity NPD7038 Approved
0.6836 Remote Similarity NPD2799 Discontinued
0.6833 Remote Similarity NPD8166 Discontinued
0.6804 Remote Similarity NPD7799 Discontinued
0.6802 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6798 Remote Similarity NPD4360 Phase 2
0.6798 Remote Similarity NPD4363 Phase 3
0.6798 Remote Similarity NPD6100 Approved
0.6798 Remote Similarity NPD6099 Approved
0.6794 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4907 Clinical (unspecified phase)
0.678 Remote Similarity NPD7097 Phase 1
0.6778 Remote Similarity NPD2800 Approved
0.6771 Remote Similarity NPD7229 Phase 3
0.6761 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6761 Remote Similarity NPD5124 Phase 1
0.676 Remote Similarity NPD2344 Approved
0.6748 Remote Similarity NPD8285 Discontinued
0.6746 Remote Similarity NPD1091 Approved
0.6744 Remote Similarity NPD2798 Approved
0.6742 Remote Similarity NPD8059 Phase 3
0.6742 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6738 Remote Similarity NPD6386 Approved
0.6738 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6738 Remote Similarity NPD6385 Approved
0.6736 Remote Similarity NPD5242 Approved
0.6734 Remote Similarity NPD7090 Clinical (unspecified phase)

  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