Structure

Physi-Chem Properties

Molecular Weight:  498.37
Volume:  546.497
LogP:  6.559
LogD:  5.636
LogS:  -5.137
# Rotatable Bonds:  3
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.313
Synthetic Accessibility Score:  4.868
Fsp3:  0.875
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.28
MDCK Permeability:  3.1071009289007634e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.457
30% Bioavailability (F30%):  0.721

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.016
Plasma Protein Binding (PPB):  95.9332046508789%
Volume Distribution (VD):  0.783
Pgp-substrate:  2.049679756164551%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.201
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.928
CYP2C9-inhibitor:  0.197
CYP2C9-substrate:  0.883
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.187
CYP3A4-inhibitor:  0.315
CYP3A4-substrate:  0.542

ADMET: Excretion

Clearance (CL):  2.229
Half-life (T1/2):  0.126

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.143
Drug-inuced Liver Injury (DILI):  0.024
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.028
Maximum Recommended Daily Dose:  0.295
Skin Sensitization:  0.079
Carcinogencity:  0.01
Eye Corrosion:  0.781
Eye Irritation:  0.933
Respiratory Toxicity:  0.947

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

  Natural Product: NPC60735

Natural Product ID:  NPC60735
Common Name*:   Quercetin-3,4'-Diglucoside
IUPAC Name:   5,7-dihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:   Quercetin-3,4'-Diglucoside
Standard InCHIKey:  RPVIQWDFJPYNJM-DEFKTLOSSA-N
Standard InCHI:  InChI=1S/C27H30O17/c28-6-14-17(33)20(36)22(38)26(42-14)41-12-2-1-8(3-10(12)31)24-25(19(35)16-11(32)4-9(30)5-13(16)40-24)44-27-23(39)21(37)18(34)15(7-29)43-27/h1-5,14-15,17-18,20-23,26-34,36-39H,6-7H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2ccc(cc2O)c2oc3cc(O)cc(c3c(=O)c2O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1098352
PubChem CID:   5320835
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
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. fruit n.a. DOI[10.1007/s11306-014-0728-9]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(01)00320-X]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. DOI[10.1038/sdata.2014.29]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[11171227]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. leaf n.a. PMID[11738417]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[12576668]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[16748484]
NPO3862 Solanum habrochaites Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[19155349]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[20597533]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. fruit n.a. PMID[21462031]
NPO3860.1 Allium victorialis Under-species n.a. n.a. Leaves Taeback, GangWon province, Korea 2011-Jan PMID[23149227]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[23656415]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[25650289]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. seed n.a. PMID[25891114]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[8987503]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota Bulb n.a. n.a. Database[FooDB]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3862 Solanum habrochaites Species Solanaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. fruit n.a. Database[MetaboLights]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3862 Solanum habrochaites Species Solanaceae 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
NPO23230.2 NPC60735 n.a. n.a. 3.125 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]
NPO23230.2 NPC60735 n.a. n.a. 26.57548 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]
NPO23230.2 NPC60735 n.a. n.a. 77.07696 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]
NPO23230.2 NPC60735 n.a. n.a. 74.62 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]

☑ 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
NPT34 Cell Line BV-2 Mus musculus Activity = 100.5 % PMID[468398]
NPT34 Cell Line BV-2 Mus musculus IC50 = 45470.0 nM PMID[468398]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Activity = 101.2 % PMID[468399]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Activity = 98.8 % PMID[468399]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Activity = 94.3 % PMID[468399]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Activity = 101.5 % PMID[468399]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Activity = 99.3 % PMID[468399]
NPT169 Cell Line B16-F10 Mus musculus Activity = 107.3 % PMID[468399]
NPT169 Cell Line B16-F10 Mus musculus Activity = 104.1 % PMID[468399]
NPT169 Cell Line B16-F10 Mus musculus Activity = 77.4 % PMID[468399]
NPT169 Cell Line B16-F10 Mus musculus Activity = 89.7 % PMID[468399]
NPT169 Cell Line B16-F10 Mus musculus Activity = 90.4 % PMID[468399]
NPT169 Cell Line B16-F10 Mus musculus Activity = 92.6 % PMID[468399]
NPT35 Others n.a. Daq = 6.1 10'-6cm2/s PMID[468397]
NPT35 Others n.a. LogP = 3.24 n.a. PMID[468397]
NPT27 Others Unspecified permeability = 8.9 10'-4 cm/s PMID[468397]
NPT605 Organism Homo sapiens Homo sapiens F = 60.0 % PMID[468397]
NPT35 Others n.a. pKa = 6.9 n.a. PMID[468397]

☑ 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 NPC60735 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 NPC26230
0.9938 High Similarity NPC285197
0.9938 High Similarity NPC156869
0.9938 High Similarity NPC67326
0.9938 High Similarity NPC254855
0.9938 High Similarity NPC259896
0.9938 High Similarity NPC255157
0.9938 High Similarity NPC136042
0.9938 High Similarity NPC29958
0.9877 High Similarity NPC16194
0.9877 High Similarity NPC294815
0.9877 High Similarity NPC19108
0.9877 High Similarity NPC473327
0.9877 High Similarity NPC220173
0.9877 High Similarity NPC476472
0.9876 High Similarity NPC471748
0.9876 High Similarity NPC134532
0.9876 High Similarity NPC471725
0.9876 High Similarity NPC203259
0.9876 High Similarity NPC33054
0.9876 High Similarity NPC176740
0.9876 High Similarity NPC155877
0.9816 High Similarity NPC8573
0.9816 High Similarity NPC219043
0.9814 High Similarity NPC67105
0.9814 High Similarity NPC95866
0.9812 High Similarity NPC275454
0.9756 High Similarity NPC173837
0.9756 High Similarity NPC251417
0.9756 High Similarity NPC89052
0.9755 High Similarity NPC253685
0.9752 High Similarity NPC223747
0.9752 High Similarity NPC86008
0.9752 High Similarity NPC225434
0.9752 High Similarity NPC203050
0.9752 High Similarity NPC120099
0.9752 High Similarity NPC219904
0.9752 High Similarity NPC227508
0.975 High Similarity NPC274618
0.975 High Similarity NPC8856
0.975 High Similarity NPC56077
0.975 High Similarity NPC118284
0.975 High Similarity NPC145038
0.975 High Similarity NPC21100
0.975 High Similarity NPC179950
0.975 High Similarity NPC281131
0.975 High Similarity NPC253662
0.975 High Similarity NPC88789
0.975 High Similarity NPC308404
0.975 High Similarity NPC197285
0.975 High Similarity NPC276222
0.9697 High Similarity NPC241423
0.9697 High Similarity NPC473571
0.9697 High Similarity NPC473682
0.9697 High Similarity NPC110941
0.9697 High Similarity NPC470443
0.9697 High Similarity NPC126784
0.9697 High Similarity NPC192539
0.9697 High Similarity NPC470444
0.9695 High Similarity NPC169733
0.9695 High Similarity NPC202908
0.9695 High Similarity NPC122467
0.9695 High Similarity NPC89127
0.9695 High Similarity NPC471669
0.9695 High Similarity NPC65563
0.9695 High Similarity NPC470949
0.9695 High Similarity NPC14187
0.9695 High Similarity NPC292019
0.9695 High Similarity NPC48984
0.9691 High Similarity NPC206123
0.9689 High Similarity NPC265530
0.9689 High Similarity NPC226304
0.9689 High Similarity NPC127546
0.9689 High Similarity NPC92565
0.9689 High Similarity NPC52550
0.9689 High Similarity NPC173637
0.9689 High Similarity NPC160156
0.9689 High Similarity NPC325555
0.9689 High Similarity NPC84362
0.9689 High Similarity NPC223424
0.9689 High Similarity NPC317489
0.9688 High Similarity NPC240431
0.9688 High Similarity NPC277205
0.9688 High Similarity NPC55786
0.9688 High Similarity NPC19388
0.9639 High Similarity NPC473073
0.9639 High Similarity NPC473071
0.9634 High Similarity NPC294629
0.9632 High Similarity NPC3583
0.9632 High Similarity NPC153755
0.9632 High Similarity NPC180918
0.9632 High Similarity NPC259152
0.963 High Similarity NPC195257
0.963 High Similarity NPC270578
0.963 High Similarity NPC52382
0.963 High Similarity NPC209296
0.9627 High Similarity NPC210073
0.9627 High Similarity NPC115674
0.9627 High Similarity NPC135599
0.9627 High Similarity NPC113968
0.9627 High Similarity NPC277174
0.9627 High Similarity NPC328940
0.9627 High Similarity NPC73855
0.9625 High Similarity NPC191306
0.9625 High Similarity NPC270335
0.9581 High Similarity NPC470718
0.9581 High Similarity NPC470445
0.9581 High Similarity NPC470449
0.9581 High Similarity NPC473072
0.9581 High Similarity NPC470447
0.9581 High Similarity NPC470446
0.9576 High Similarity NPC473862
0.9573 High Similarity NPC42773
0.9573 High Similarity NPC101026
0.9573 High Similarity NPC21666
0.9573 High Similarity NPC4390
0.9573 High Similarity NPC45522
0.9573 High Similarity NPC24043
0.9573 High Similarity NPC169977
0.9571 High Similarity NPC282987
0.9571 High Similarity NPC244776
0.9571 High Similarity NPC51326
0.9571 High Similarity NPC218488
0.9571 High Similarity NPC231194
0.9571 High Similarity NPC116864
0.9571 High Similarity NPC235260
0.9571 High Similarity NPC20505
0.9571 High Similarity NPC155763
0.9571 High Similarity NPC245014
0.9571 High Similarity NPC84265
0.9565 High Similarity NPC311830
0.9565 High Similarity NPC22832
0.9563 High Similarity NPC189142
0.9563 High Similarity NPC77660
0.9524 High Similarity NPC470451
0.9524 High Similarity NPC25946
0.9524 High Similarity NPC470720
0.9524 High Similarity NPC470717
0.9524 High Similarity NPC148710
0.9524 High Similarity NPC460984
0.9524 High Similarity NPC470455
0.9524 High Similarity NPC470713
0.9524 High Similarity NPC21359
0.9518 High Similarity NPC37668
0.9518 High Similarity NPC113836
0.9518 High Similarity NPC217520
0.9518 High Similarity NPC139571
0.9518 High Similarity NPC253521
0.9515 High Similarity NPC223426
0.9515 High Similarity NPC81042
0.9515 High Similarity NPC210094
0.9515 High Similarity NPC49344
0.9515 High Similarity NPC135277
0.9515 High Similarity NPC198199
0.9515 High Similarity NPC115760
0.9515 High Similarity NPC43211
0.9515 High Similarity NPC237435
0.9515 High Similarity NPC34267
0.9515 High Similarity NPC214621
0.9515 High Similarity NPC101191
0.9512 High Similarity NPC190003
0.9512 High Similarity NPC245452
0.9512 High Similarity NPC117260
0.9512 High Similarity NPC256760
0.9512 High Similarity NPC175107
0.9512 High Similarity NPC476405
0.9509 High Similarity NPC138927
0.9509 High Similarity NPC105283
0.9506 High Similarity NPC255615
0.9506 High Similarity NPC67037
0.9506 High Similarity NPC254306
0.9506 High Similarity NPC236934
0.9506 High Similarity NPC5778
0.9503 High Similarity NPC243930
0.9503 High Similarity NPC284960
0.9503 High Similarity NPC168822
0.9503 High Similarity NPC88023
0.9503 High Similarity NPC309025
0.9503 High Similarity NPC222936
0.9503 High Similarity NPC29830
0.9503 High Similarity NPC19709
0.95 High Similarity NPC170052
0.95 High Similarity NPC64305
0.95 High Similarity NPC297987
0.95 High Similarity NPC135846
0.9467 High Similarity NPC470719
0.9467 High Similarity NPC473554
0.9467 High Similarity NPC295625
0.9464 High Similarity NPC241781
0.9464 High Similarity NPC162394
0.9464 High Similarity NPC156785
0.9458 High Similarity NPC144097
0.9458 High Similarity NPC61904
0.9458 High Similarity NPC268533
0.9458 High Similarity NPC472385
0.9458 High Similarity NPC198324
0.9455 High Similarity NPC208668
0.9455 High Similarity NPC204693
0.9451 High Similarity NPC79056
0.9451 High Similarity NPC105095

  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 NPC60735 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
0.9876 High Similarity NPD6797 Phase 2
0.9815 High Similarity NPD7251 Discontinued
0.9755 High Similarity NPD7808 Phase 3
0.9691 High Similarity NPD7472 Approved
0.963 High Similarity NPD7054 Approved
0.9515 High Similarity NPD4338 Clinical (unspecified phase)
0.9451 High Similarity NPD7074 Phase 3
0.9212 High Similarity NPD3818 Discontinued
0.9207 High Similarity NPD6166 Phase 2
0.9207 High Similarity NPD6167 Clinical (unspecified phase)
0.9207 High Similarity NPD6168 Clinical (unspecified phase)
0.9157 High Similarity NPD7804 Clinical (unspecified phase)
0.9074 High Similarity NPD4381 Clinical (unspecified phase)
0.8834 High Similarity NPD3817 Phase 2
0.8827 High Similarity NPD1934 Approved
0.8688 High Similarity NPD1512 Approved
0.8667 High Similarity NPD3882 Suspended
0.8659 High Similarity NPD2801 Approved
0.8659 High Similarity NPD2393 Clinical (unspecified phase)
0.8605 High Similarity NPD7993 Clinical (unspecified phase)
0.8562 High Similarity NPD1511 Approved
0.8476 Intermediate Similarity NPD4380 Phase 2
0.8443 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8393 Intermediate Similarity NPD7075 Discontinued
0.8383 Intermediate Similarity NPD5402 Approved
0.8293 Intermediate Similarity NPD5403 Approved
0.8263 Intermediate Similarity NPD6801 Discontinued
0.8239 Intermediate Similarity NPD6559 Discontinued
0.8214 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD5401 Approved
0.8171 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD1653 Approved
0.8114 Intermediate Similarity NPD3751 Discontinued
0.811 Intermediate Similarity NPD6799 Approved
0.8092 Intermediate Similarity NPD3787 Discontinued
0.8081 Intermediate Similarity NPD5494 Approved
0.8075 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8033 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD1549 Phase 2
0.8 Intermediate Similarity NPD1465 Phase 2
0.7944 Intermediate Similarity NPD8312 Approved
0.7944 Intermediate Similarity NPD8313 Approved
0.7931 Intermediate Similarity NPD6959 Discontinued
0.791 Intermediate Similarity NPD7228 Approved
0.7865 Intermediate Similarity NPD5844 Phase 1
0.7849 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD1510 Phase 2
0.7833 Intermediate Similarity NPD7685 Pre-registration
0.7824 Intermediate Similarity NPD6599 Discontinued
0.7791 Intermediate Similarity NPD7819 Suspended
0.7791 Intermediate Similarity NPD2796 Approved
0.7784 Intermediate Similarity NPD6232 Discontinued
0.7778 Intermediate Similarity NPD7411 Suspended
0.7753 Intermediate Similarity NPD7473 Discontinued
0.7751 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7199 Phase 2
0.7714 Intermediate Similarity NPD919 Approved
0.7702 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD1613 Approved
0.7688 Intermediate Similarity NPD8455 Phase 2
0.7665 Intermediate Similarity NPD6190 Approved
0.7663 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD6781 Approved
0.7644 Intermediate Similarity NPD6778 Approved
0.7644 Intermediate Similarity NPD6776 Approved
0.7644 Intermediate Similarity NPD6779 Approved
0.7644 Intermediate Similarity NPD6782 Approved
0.7644 Intermediate Similarity NPD6780 Approved
0.7644 Intermediate Similarity NPD6777 Approved
0.7636 Intermediate Similarity NPD7266 Discontinued
0.7634 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD1247 Approved
0.7617 Intermediate Similarity NPD7435 Discontinued
0.7614 Intermediate Similarity NPD6234 Discontinued
0.7602 Intermediate Similarity NPD8151 Discontinued
0.7598 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD3926 Phase 2
0.7541 Intermediate Similarity NPD7240 Approved
0.7529 Intermediate Similarity NPD37 Approved
0.7526 Intermediate Similarity NPD7696 Phase 3
0.7526 Intermediate Similarity NPD7697 Approved
0.7526 Intermediate Similarity NPD7698 Approved
0.75 Intermediate Similarity NPD3750 Approved
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD4965 Approved
0.75 Intermediate Similarity NPD4967 Phase 2
0.75 Intermediate Similarity NPD7584 Approved
0.75 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD943 Approved
0.7485 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1240 Approved
0.7471 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD7701 Phase 2
0.7453 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD1933 Approved
0.7407 Intermediate Similarity NPD3027 Phase 3
0.7398 Intermediate Similarity NPD7870 Phase 2
0.7398 Intermediate Similarity NPD7871 Phase 2
0.7396 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD1607 Approved
0.7391 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD7874 Approved
0.7387 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7382 Intermediate Similarity NPD6534 Approved
0.7382 Intermediate Similarity NPD6535 Approved
0.7365 Intermediate Similarity NPD1551 Phase 2
0.736 Intermediate Similarity NPD3749 Approved
0.7358 Intermediate Similarity NPD7700 Phase 2
0.7358 Intermediate Similarity NPD7699 Phase 2
0.735 Intermediate Similarity NPD7783 Phase 2
0.735 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD230 Phase 1
0.731 Intermediate Similarity NPD8320 Phase 1
0.731 Intermediate Similarity NPD8319 Approved
0.7305 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD7768 Phase 2
0.7294 Intermediate Similarity NPD4628 Phase 3
0.7264 Intermediate Similarity NPD7801 Approved
0.7256 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD447 Suspended
0.7208 Intermediate Similarity NPD6823 Phase 2
0.7202 Intermediate Similarity NPD3748 Approved
0.716 Intermediate Similarity NPD2935 Discontinued
0.7158 Intermediate Similarity NPD8434 Phase 2
0.7158 Intermediate Similarity NPD8150 Discontinued
0.7143 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD2532 Approved
0.7126 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD2534 Approved
0.7126 Intermediate Similarity NPD2533 Approved
0.7125 Intermediate Similarity NPD1091 Approved
0.712 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD7585 Approved
0.7107 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD7680 Approved
0.7065 Intermediate Similarity NPD7583 Approved
0.7062 Intermediate Similarity NPD7458 Discontinued
0.7048 Intermediate Similarity NPD6798 Discontinued
0.7045 Intermediate Similarity NPD920 Approved
0.7037 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6674 Discontinued
0.7035 Intermediate Similarity NPD2800 Approved
0.7033 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD4360 Phase 2
0.7026 Intermediate Similarity NPD4363 Phase 3
0.7021 Intermediate Similarity NPD5953 Discontinued
0.7011 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6233 Phase 2
0.7 Intermediate Similarity NPD7033 Discontinued
0.6974 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6974 Remote Similarity NPD6212 Phase 3
0.6974 Remote Similarity NPD6213 Phase 3
0.6971 Remote Similarity NPD7390 Discontinued
0.697 Remote Similarity NPD9494 Approved
0.6966 Remote Similarity NPD3226 Approved
0.6959 Remote Similarity NPD6099 Approved
0.6959 Remote Similarity NPD6100 Approved
0.6951 Remote Similarity NPD1203 Approved
0.6946 Remote Similarity NPD2313 Discontinued
0.6944 Remote Similarity NPD6844 Discontinued
0.6936 Remote Similarity NPD1243 Approved
0.6936 Remote Similarity NPD1652 Phase 2
0.6933 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6928 Remote Similarity NPD4908 Phase 1
0.6928 Remote Similarity NPD6832 Phase 2
0.6923 Remote Similarity NPD6355 Discontinued
0.6915 Remote Similarity NPD7286 Phase 2
0.6914 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6909 Remote Similarity NPD2798 Approved
0.6882 Remote Similarity NPD6651 Approved
0.6875 Remote Similarity NPD1548 Phase 1
0.6872 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6868 Remote Similarity NPD5353 Approved
0.6862 Remote Similarity NPD2163 Approved
0.6847 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6845 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5124 Phase 1
0.6824 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6824 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6821 Remote Similarity NPD2344 Approved
0.6821 Remote Similarity NPD2346 Discontinued
0.681 Remote Similarity NPD1610 Phase 2
0.6802 Remote Similarity NPD2799 Discontinued
0.68 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6791 Remote Similarity NPD5242 Approved
0.6788 Remote Similarity NPD3225 Approved
0.6782 Remote Similarity NPD5005 Approved
0.6782 Remote Similarity NPD5006 Approved
0.6774 Remote Similarity NPD8127 Discontinued
0.6771 Remote Similarity NPD7549 Discontinued
0.6769 Remote Similarity NPD6842 Approved
0.6769 Remote Similarity NPD6841 Approved
0.6769 Remote Similarity NPD6843 Phase 3
0.6768 Remote Similarity NPD9269 Phase 2

  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