Structure

Physi-Chem Properties

Molecular Weight:  888.23
Volume:  816.908
LogP:  1.297
LogD:  0.247
LogS:  -4.181
# Rotatable Bonds:  12
TPSA:  354.65
# H-Bond Aceptor:  22
# H-Bond Donor:  12
# Rings:  7
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.048
Synthetic Accessibility Score:  5.659
Fsp3:  0.415
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:  -6.606
MDCK Permeability:  2.3133412469178438e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.942
20% Bioavailability (F20%):  0.029
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.05
Plasma Protein Binding (PPB):  95.73480224609375%
Volume Distribution (VD):  0.506
Pgp-substrate:  10.073742866516113%

ADMET: Metabolism

CYP1A2-inhibitor:  0.072
CYP1A2-substrate:  0.01
CYP2C19-inhibitor:  0.066
CYP2C19-substrate:  0.04
CYP2C9-inhibitor:  0.149
CYP2C9-substrate:  0.097
CYP2D6-inhibitor:  0.147
CYP2D6-substrate:  0.115
CYP3A4-inhibitor:  0.079
CYP3A4-substrate:  0.003

ADMET: Excretion

Clearance (CL):  0.526
Half-life (T1/2):  0.657

ADMET: Toxicity

hERG Blockers:  0.158
Human Hepatotoxicity (H-HT):  0.111
Drug-inuced Liver Injury (DILI):  0.985
AMES Toxicity:  0.745
Rat Oral Acute Toxicity:  0.045
Maximum Recommended Daily Dose:  0.01
Skin Sensitization:  0.958
Carcinogencity:  0.064
Eye Corrosion:  0.003
Eye Irritation:  0.144
Respiratory Toxicity:  0.012

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

  Natural Product: NPC275977

Natural Product ID:  NPC275977
Common Name*:   Camelliquercetiside C
IUPAC Name:   [(2S,3R,4S,5R,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-5-hydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:   Camelliquercetiside C
Standard InCHIKey:  WJNXAFADOMWGIU-UFYQSDDJSA-N
Standard InCHI:  InChI=1S/C41H44O22/c1-15-28(49)32(53)34(55)39(58-15)57-14-25-30(51)36(62-40-33(54)29(50)23(47)13-56-40)38(61-26(48)9-4-16-2-6-18(42)7-3-16)41(60-25)63-37-31(52)27-22(46)11-19(43)12-24(27)59-35(37)17-5-8-20(44)21(45)10-17/h2-12,15,23,25,28-30,32-34,36,38-47,49-51,53-55H,13-14H2,1H3/b9-4+/t15-,23-,25+,28-,29-,30+,32+,33+,34+,36-,38+,39+,40-,41-/m0/s1
SMILES:  O=C(O[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O)CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1957048
PubChem CID:   57400005
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 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 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. 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 = 46700.0 nM PMID[474423]
NPT1 Others Radical scavenging activity IC50 = 31900.0 nM PMID[474423]

☑ 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 NPC275977 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 NPC223860
1.0 High Similarity NPC249560
0.9941 High Similarity NPC470719
0.9941 High Similarity NPC295625
0.9941 High Similarity NPC33083
0.9941 High Similarity NPC473554
0.994 High Similarity NPC241781
0.994 High Similarity NPC162394
0.994 High Similarity NPC156785
0.9882 High Similarity NPC21359
0.9882 High Similarity NPC30011
0.9882 High Similarity NPC97817
0.9882 High Similarity NPC470713
0.9882 High Similarity NPC72554
0.9882 High Similarity NPC25946
0.9882 High Similarity NPC460984
0.9882 High Similarity NPC470720
0.9882 High Similarity NPC470717
0.9822 High Similarity NPC470718
0.9708 High Similarity NPC104910
0.9708 High Similarity NPC474093
0.9702 High Similarity NPC292019
0.9702 High Similarity NPC89127
0.9702 High Similarity NPC473862
0.9702 High Similarity NPC122467
0.9702 High Similarity NPC14187
0.9702 High Similarity NPC471669
0.9702 High Similarity NPC202908
0.9651 High Similarity NPC475179
0.9645 High Similarity NPC37668
0.9645 High Similarity NPC139571
0.9645 High Similarity NPC251417
0.9645 High Similarity NPC35167
0.9645 High Similarity NPC267680
0.9645 High Similarity NPC217387
0.9645 High Similarity NPC173837
0.9645 High Similarity NPC217520
0.9645 High Similarity NPC89052
0.9645 High Similarity NPC258044
0.9645 High Similarity NPC293626
0.9645 High Similarity NPC113836
0.9645 High Similarity NPC196127
0.9645 High Similarity NPC477895
0.9645 High Similarity NPC253521
0.9643 High Similarity NPC34267
0.9643 High Similarity NPC214621
0.9643 High Similarity NPC223426
0.9643 High Similarity NPC81042
0.9591 High Similarity NPC297503
0.9591 High Similarity NPC97119
0.9591 High Similarity NPC135831
0.9588 High Similarity NPC192539
0.9586 High Similarity NPC219043
0.9586 High Similarity NPC61904
0.9586 High Similarity NPC48984
0.9586 High Similarity NPC144097
0.9535 High Similarity NPC470455
0.9535 High Similarity NPC470451
0.9535 High Similarity NPC470416
0.9529 High Similarity NPC120952
0.9527 High Similarity NPC476472
0.9527 High Similarity NPC19108
0.9527 High Similarity NPC253685
0.9527 High Similarity NPC220173
0.9527 High Similarity NPC294815
0.9527 High Similarity NPC473327
0.9527 High Similarity NPC16194
0.9524 High Similarity NPC203259
0.9524 High Similarity NPC33054
0.9524 High Similarity NPC176740
0.9524 High Similarity NPC470714
0.9524 High Similarity NPC470716
0.9524 High Similarity NPC474522
0.9524 High Similarity NPC155877
0.9524 High Similarity NPC471748
0.9524 High Similarity NPC470715
0.9524 High Similarity NPC471725
0.9524 High Similarity NPC134532
0.9477 High Similarity NPC470445
0.9477 High Similarity NPC35924
0.9477 High Similarity NPC470446
0.9477 High Similarity NPC36138
0.9477 High Similarity NPC199172
0.9477 High Similarity NPC470449
0.9477 High Similarity NPC470447
0.9474 High Similarity NPC471030
0.9471 High Similarity NPC231787
0.9467 High Similarity NPC472993
0.9464 High Similarity NPC164704
0.9464 High Similarity NPC67326
0.9464 High Similarity NPC255157
0.9464 High Similarity NPC254855
0.9464 High Similarity NPC67105
0.9464 High Similarity NPC156869
0.9464 High Similarity NPC244776
0.9464 High Similarity NPC470712
0.9464 High Similarity NPC29958
0.9464 High Similarity NPC116864
0.9464 High Similarity NPC136042
0.9464 High Similarity NPC95866
0.9464 High Similarity NPC259896
0.9425 High Similarity NPC64755
0.9419 High Similarity NPC469371
0.9412 High Similarity NPC198199
0.9408 High Similarity NPC60735
0.9408 High Similarity NPC153755
0.9408 High Similarity NPC175107
0.9408 High Similarity NPC26230
0.9408 High Similarity NPC67134
0.9408 High Similarity NPC47140
0.9408 High Similarity NPC180918
0.9408 High Similarity NPC190003
0.9405 High Similarity NPC227508
0.936 High Similarity NPC473682
0.936 High Similarity NPC110941
0.936 High Similarity NPC241423
0.936 High Similarity NPC473571
0.936 High Similarity NPC126784
0.936 High Similarity NPC470443
0.936 High Similarity NPC470444
0.9357 High Similarity NPC470949
0.9357 High Similarity NPC65563
0.9357 High Similarity NPC296018
0.9357 High Similarity NPC154741
0.9353 High Similarity NPC4390
0.9353 High Similarity NPC172033
0.9353 High Similarity NPC88560
0.9353 High Similarity NPC175230
0.9349 High Similarity NPC20505
0.9349 High Similarity NPC155763
0.9349 High Similarity NPC206123
0.9349 High Similarity NPC235260
0.9349 High Similarity NPC285197
0.9345 High Similarity NPC84362
0.9345 High Similarity NPC275454
0.9345 High Similarity NPC223424
0.9345 High Similarity NPC173637
0.9345 High Similarity NPC127546
0.9345 High Similarity NPC317489
0.9345 High Similarity NPC52550
0.9302 High Similarity NPC476773
0.9298 High Similarity NPC294629
0.9294 High Similarity NPC221288
0.9294 High Similarity NPC101399
0.9294 High Similarity NPC11847
0.9294 High Similarity NPC217822
0.929 High Similarity NPC195257
0.929 High Similarity NPC52382
0.929 High Similarity NPC223747
0.929 High Similarity NPC203050
0.929 High Similarity NPC138927
0.929 High Similarity NPC43587
0.929 High Similarity NPC86008
0.929 High Similarity NPC219904
0.929 High Similarity NPC209296
0.929 High Similarity NPC105283
0.929 High Similarity NPC270578
0.929 High Similarity NPC225434
0.929 High Similarity NPC120099
0.9286 High Similarity NPC73855
0.9286 High Similarity NPC256188
0.9286 High Similarity NPC328940
0.9286 High Similarity NPC56077
0.9286 High Similarity NPC8856
0.9286 High Similarity NPC32641
0.9286 High Similarity NPC476470
0.9286 High Similarity NPC281131
0.9286 High Similarity NPC253662
0.9286 High Similarity NPC142142
0.9286 High Similarity NPC88789
0.9286 High Similarity NPC12013
0.9286 High Similarity NPC477613
0.9286 High Similarity NPC118284
0.9286 High Similarity NPC210073
0.9286 High Similarity NPC221342
0.9286 High Similarity NPC308404
0.9286 High Similarity NPC11432
0.9286 High Similarity NPC64425
0.9286 High Similarity NPC186816
0.9286 High Similarity NPC145038
0.9286 High Similarity NPC113968
0.9286 High Similarity NPC115674
0.9286 High Similarity NPC274618
0.9286 High Similarity NPC135599
0.9286 High Similarity NPC276222
0.9286 High Similarity NPC277174
0.9286 High Similarity NPC203145
0.9286 High Similarity NPC189564
0.9286 High Similarity NPC179950
0.9253 High Similarity NPC473072
0.9244 High Similarity NPC472991
0.9244 High Similarity NPC255799
0.9244 High Similarity NPC169733
0.9244 High Similarity NPC472992
0.9244 High Similarity NPC472385
0.9244 High Similarity NPC8573
0.9244 High Similarity NPC198324
0.924 High Similarity NPC25724
0.9235 High Similarity NPC51326
0.9235 High Similarity NPC209550

  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 NPC275977 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
0.9583 High Similarity NPD7251 Discontinued
0.9527 High Similarity NPD7808 Phase 3
0.9524 High Similarity NPD6797 Phase 2
0.9349 High Similarity NPD7472 Approved
0.929 High Similarity NPD7054 Approved
0.9235 High Similarity NPD7074 Phase 3
0.9186 High Similarity NPD4338 Clinical (unspecified phase)
0.9064 High Similarity NPD7804 Clinical (unspecified phase)
0.9 High Similarity NPD6166 Phase 2
0.9 High Similarity NPD6168 Clinical (unspecified phase)
0.9 High Similarity NPD6167 Clinical (unspecified phase)
0.8851 High Similarity NPD7993 Clinical (unspecified phase)
0.8786 High Similarity NPD3818 Discontinued
0.8757 High Similarity NPD4381 Clinical (unspecified phase)
0.8639 High Similarity NPD3817 Phase 2
0.8588 High Similarity NPD4868 Clinical (unspecified phase)
0.8538 High Similarity NPD7075 Discontinued
0.8412 Intermediate Similarity NPD1934 Approved
0.8372 Intermediate Similarity NPD3882 Suspended
0.837 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8363 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8363 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8314 Intermediate Similarity NPD5402 Approved
0.8304 Intermediate Similarity NPD6801 Discontinued
0.8287 Intermediate Similarity NPD8313 Approved
0.8287 Intermediate Similarity NPD8312 Approved
0.8278 Intermediate Similarity NPD6559 Discontinued
0.8274 Intermediate Similarity NPD1512 Approved
0.8256 Intermediate Similarity NPD2801 Approved
0.8225 Intermediate Similarity NPD5403 Approved
0.8187 Intermediate Similarity NPD4380 Phase 2
0.8155 Intermediate Similarity NPD1511 Approved
0.8155 Intermediate Similarity NPD6799 Approved
0.8107 Intermediate Similarity NPD5401 Approved
0.8046 Intermediate Similarity NPD7819 Suspended
0.8035 Intermediate Similarity NPD7411 Suspended
0.8011 Intermediate Similarity NPD5844 Phase 1
0.801 Intermediate Similarity NPD8151 Discontinued
0.8 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7978 Intermediate Similarity NPD7685 Pre-registration
0.7968 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7965 Intermediate Similarity NPD1653 Approved
0.7956 Intermediate Similarity NPD3751 Discontinued
0.7956 Intermediate Similarity NPD7228 Approved
0.7944 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD8455 Phase 2
0.7907 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7903 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD7473 Discontinued
0.7895 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7889 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD6959 Discontinued
0.7874 Intermediate Similarity NPD6599 Discontinued
0.7846 Intermediate Similarity NPD7435 Discontinued
0.7841 Intermediate Similarity NPD1465 Phase 2
0.7833 Intermediate Similarity NPD3787 Discontinued
0.7833 Intermediate Similarity NPD6232 Discontinued
0.7821 Intermediate Similarity NPD5494 Approved
0.7812 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD7266 Discontinued
0.7791 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7199 Phase 2
0.7753 Intermediate Similarity NPD7768 Phase 2
0.7751 Intermediate Similarity NPD1549 Phase 2
0.775 Intermediate Similarity NPD7783 Phase 2
0.775 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD6190 Approved
0.7716 Intermediate Similarity NPD8320 Phase 1
0.7716 Intermediate Similarity NPD8319 Approved
0.77 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.77 Intermediate Similarity NPD7874 Approved
0.7692 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD919 Approved
0.7665 Intermediate Similarity NPD7696 Phase 3
0.7665 Intermediate Similarity NPD7697 Approved
0.7665 Intermediate Similarity NPD7698 Approved
0.7633 Intermediate Similarity NPD2796 Approved
0.7626 Intermediate Similarity NPD7871 Phase 2
0.7626 Intermediate Similarity NPD7870 Phase 2
0.7602 Intermediate Similarity NPD6777 Approved
0.7602 Intermediate Similarity NPD6778 Approved
0.7602 Intermediate Similarity NPD6779 Approved
0.7602 Intermediate Similarity NPD6780 Approved
0.7602 Intermediate Similarity NPD6776 Approved
0.7602 Intermediate Similarity NPD6782 Approved
0.7602 Intermediate Similarity NPD6781 Approved
0.76 Intermediate Similarity NPD7701 Phase 2
0.7594 Intermediate Similarity NPD7240 Approved
0.7574 Intermediate Similarity NPD1510 Phase 2
0.7569 Intermediate Similarity NPD6234 Discontinued
0.7558 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD3749 Approved
0.75 Intermediate Similarity NPD7699 Phase 2
0.75 Intermediate Similarity NPD7700 Phase 2
0.7487 Intermediate Similarity NPD8150 Discontinued
0.7486 Intermediate Similarity NPD37 Approved
0.7463 Intermediate Similarity NPD7584 Approved
0.7459 Intermediate Similarity NPD4967 Phase 2
0.7459 Intermediate Similarity NPD4966 Approved
0.7459 Intermediate Similarity NPD4965 Approved
0.7457 Intermediate Similarity NPD3750 Approved
0.7442 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD3926 Phase 2
0.7402 Intermediate Similarity NPD7801 Approved
0.7399 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD230 Phase 1
0.7396 Intermediate Similarity NPD8434 Phase 2
0.7396 Intermediate Similarity NPD1933 Approved
0.7391 Intermediate Similarity NPD1247 Approved
0.7366 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD4628 Phase 3
0.7347 Intermediate Similarity NPD6534 Approved
0.7347 Intermediate Similarity NPD6535 Approved
0.7337 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD1240 Approved
0.7337 Intermediate Similarity NPD1613 Approved
0.7326 Intermediate Similarity NPD1551 Phase 2
0.7321 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD7458 Discontinued
0.7313 Intermediate Similarity NPD7680 Approved
0.7264 Intermediate Similarity NPD6823 Phase 2
0.7255 Intermediate Similarity NPD7585 Approved
0.7251 Intermediate Similarity NPD1607 Approved
0.7235 Intermediate Similarity NPD943 Approved
0.7225 Intermediate Similarity NPD2935 Discontinued
0.7219 Intermediate Similarity NPD6798 Discontinued
0.7206 Intermediate Similarity NPD7583 Approved
0.72 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD447 Suspended
0.7191 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6233 Phase 2
0.7168 Intermediate Similarity NPD3748 Approved
0.7127 Intermediate Similarity NPD3226 Approved
0.7111 Intermediate Similarity NPD920 Approved
0.7103 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6832 Phase 2
0.7095 Intermediate Similarity NPD2533 Approved
0.7095 Intermediate Similarity NPD2532 Approved
0.7095 Intermediate Similarity NPD2534 Approved
0.7083 Intermediate Similarity NPD5953 Discontinued
0.7069 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD7286 Phase 2
0.7059 Intermediate Similarity NPD3027 Phase 3
0.7041 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD8127 Discontinued
0.7006 Intermediate Similarity NPD1243 Approved
0.7 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.6995 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6994 Remote Similarity NPD6355 Discontinued
0.6983 Remote Similarity NPD643 Clinical (unspecified phase)
0.6971 Remote Similarity NPD7033 Discontinued
0.6966 Remote Similarity NPD6398 Clinical (unspecified phase)
0.695 Remote Similarity NPD6214 Clinical (unspecified phase)
0.695 Remote Similarity NPD6212 Phase 3
0.695 Remote Similarity NPD6213 Phase 3
0.6944 Remote Similarity NPD7390 Discontinued
0.6935 Remote Similarity NPD5353 Approved
0.6923 Remote Similarity NPD1203 Approved
0.6923 Remote Similarity NPD7549 Discontinued
0.6919 Remote Similarity NPD2313 Discontinued
0.6919 Remote Similarity NPD6844 Discontinued
0.691 Remote Similarity NPD1652 Phase 2
0.691 Remote Similarity NPD6674 Discontinued
0.6901 Remote Similarity NPD4908 Phase 1
0.6897 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6893 Remote Similarity NPD2346 Discontinued
0.6887 Remote Similarity NPD7930 Approved
0.6875 Remote Similarity NPD2799 Discontinued
0.6872 Remote Similarity NPD7038 Approved
0.6872 Remote Similarity NPD8166 Discontinued
0.6872 Remote Similarity NPD7039 Approved
0.6839 Remote Similarity NPD7799 Discontinued
0.6837 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6836 Remote Similarity NPD6100 Approved
0.6836 Remote Similarity NPD6099 Approved
0.6832 Remote Similarity NPD4363 Phase 3
0.6832 Remote Similarity NPD4360 Phase 2
0.6827 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6821 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7097 Phase 1
0.6816 Remote Similarity NPD2800 Approved
0.6806 Remote Similarity NPD7229 Phase 3
0.68 Remote Similarity NPD5124 Phase 1
0.68 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6798 Remote Similarity NPD2344 Approved
0.6786 Remote Similarity NPD1091 Approved
0.6784 Remote Similarity NPD2798 Approved
0.678 Remote Similarity NPD8285 Discontinued
0.6774 Remote Similarity NPD6386 Approved
0.6774 Remote Similarity NPD6385 Approved
0.6774 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6773 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6773 Remote Similarity NPD8059 Phase 3
0.6771 Remote Similarity NPD5242 Approved
0.6768 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