Structure

Physi-Chem Properties

Molecular Weight:  626.15
Volume:  561.108
LogP:  -0.647
LogD:  -0.497
LogS:  -3.045
# Rotatable Bonds:  7
TPSA:  289.66
# H-Bond Aceptor:  17
# H-Bond Donor:  11
# Rings:  5
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.124
Synthetic Accessibility Score:  4.782
Fsp3:  0.444
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.614
MDCK Permeability:  3.735605423571542e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.987
Human Intestinal Absorption (HIA):  0.88
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.096
Plasma Protein Binding (PPB):  78.14692687988281%
Volume Distribution (VD):  0.69
Pgp-substrate:  14.502286911010742%

ADMET: Metabolism

CYP1A2-inhibitor:  0.121
CYP1A2-substrate:  0.016
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.058
CYP2D6-inhibitor:  0.024
CYP2D6-substrate:  0.125
CYP3A4-inhibitor:  0.013
CYP3A4-substrate:  0.002

ADMET: Excretion

Clearance (CL):  1.202
Half-life (T1/2):  0.82

ADMET: Toxicity

hERG Blockers:  0.418
Human Hepatotoxicity (H-HT):  0.072
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.826
Rat Oral Acute Toxicity:  0.007
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.172
Carcinogencity:  0.052
Eye Corrosion:  0.003
Eye Irritation:  0.036
Respiratory Toxicity:  0.009

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

  Natural Product: NPC285197

Natural Product ID:  NPC285197
Common Name*:   Quercetin 7,4'-Di-O-Beta-D-Glucopyranoside
IUPAC Name:   3,5-dihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:  
Standard InCHIKey:  QZXHFNCQMMUANB-UINLEYECSA-N
Standard InCHI:  InChI=1S/C27H30O17/c28-6-14-17(32)20(35)23(38)26(43-14)40-9-4-11(31)16-13(5-9)41-25(22(37)19(16)34)8-1-2-12(10(30)3-8)42-27-24(39)21(36)18(33)15(7-29)44-27/h1-5,14-15,17-18,20-21,23-24,26-33,35-39H,6-7H2/t14-,15-,17-,18-,20+,21+,23-,24-,26-,27-/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)O)c2ccc(c(c2)O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2206210
PubChem CID:   11968881
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003533] Flavonoid-7-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]
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]
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]
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]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[25466012]
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]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[28245113]
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]
NPO10331 Allium ascalonicum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17086 Hibiscus rosa-sinensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10331 Allium ascalonicum Species Amaryllidaceae 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]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21080 Solanum lycopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10331 Allium ascalonicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17086 Hibiscus rosa-sinensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10331 Allium ascalonicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17086 Hibiscus rosa-sinensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17086 Hibiscus rosa-sinensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10331 Allium ascalonicum 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]
NPO23230 Allium cepa Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae 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

☑ 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 = 105.3 % PMID[523560]
NPT34 Cell Line BV-2 Mus musculus IC50 = 51730.0 nM PMID[523560]

☑ 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 NPC285197 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
0.9938 High Similarity NPC26230
0.9938 High Similarity NPC60735
0.9875 High Similarity NPC156869
0.9875 High Similarity NPC136042
0.9875 High Similarity NPC67105
0.9875 High Similarity NPC254855
0.9875 High Similarity NPC259896
0.9875 High Similarity NPC255157
0.9875 High Similarity NPC67326
0.9875 High Similarity NPC29958
0.9874 High Similarity NPC275454
0.9815 High Similarity NPC16194
0.9815 High Similarity NPC476472
0.9815 High Similarity NPC220173
0.9815 High Similarity NPC473327
0.9815 High Similarity NPC294815
0.9815 High Similarity NPC19108
0.9814 High Similarity NPC471725
0.9814 High Similarity NPC203259
0.9814 High Similarity NPC134532
0.9814 High Similarity NPC176740
0.9814 High Similarity NPC33054
0.9814 High Similarity NPC155877
0.9814 High Similarity NPC471748
0.9812 High Similarity NPC86008
0.9812 High Similarity NPC227508
0.9811 High Similarity NPC197285
0.9811 High Similarity NPC8856
0.9811 High Similarity NPC21100
0.9755 High Similarity NPC8573
0.9755 High Similarity NPC219043
0.9755 High Similarity NPC169733
0.9752 High Similarity NPC95866
0.9748 High Similarity NPC277205
0.9695 High Similarity NPC89052
0.9695 High Similarity NPC251417
0.9695 High Similarity NPC173837
0.9693 High Similarity NPC253685
0.9691 High Similarity NPC3583
0.9691 High Similarity NPC180918
0.9691 High Similarity NPC259152
0.9689 High Similarity NPC225434
0.9689 High Similarity NPC209296
0.9689 High Similarity NPC120099
0.9689 High Similarity NPC219904
0.9689 High Similarity NPC203050
0.9689 High Similarity NPC195257
0.9689 High Similarity NPC223747
0.9688 High Similarity NPC253662
0.9688 High Similarity NPC145038
0.9688 High Similarity NPC88789
0.9688 High Similarity NPC274618
0.9688 High Similarity NPC210073
0.9688 High Similarity NPC115674
0.9688 High Similarity NPC118284
0.9688 High Similarity NPC179950
0.9688 High Similarity NPC281131
0.9688 High Similarity NPC56077
0.9688 High Similarity NPC276222
0.9688 High Similarity NPC308404
0.9686 High Similarity NPC270335
0.9686 High Similarity NPC191306
0.9636 High Similarity NPC241423
0.9636 High Similarity NPC192539
0.9636 High Similarity NPC473682
0.9636 High Similarity NPC470444
0.9636 High Similarity NPC110941
0.9636 High Similarity NPC470443
0.9636 High Similarity NPC126784
0.9636 High Similarity NPC473571
0.9634 High Similarity NPC65563
0.9634 High Similarity NPC14187
0.9634 High Similarity NPC122467
0.9634 High Similarity NPC470949
0.9634 High Similarity NPC471669
0.9634 High Similarity NPC202908
0.9634 High Similarity NPC292019
0.9634 High Similarity NPC48984
0.9634 High Similarity NPC89127
0.963 High Similarity NPC245014
0.963 High Similarity NPC218488
0.963 High Similarity NPC206123
0.963 High Similarity NPC231194
0.963 High Similarity NPC84265
0.963 High Similarity NPC51326
0.963 High Similarity NPC282987
0.9627 High Similarity NPC325555
0.9627 High Similarity NPC127546
0.9627 High Similarity NPC84362
0.9627 High Similarity NPC92565
0.9627 High Similarity NPC265530
0.9627 High Similarity NPC226304
0.9627 High Similarity NPC52550
0.9627 High Similarity NPC223424
0.9627 High Similarity NPC317489
0.9627 High Similarity NPC160156
0.9627 High Similarity NPC173637
0.9625 High Similarity NPC55786
0.9625 High Similarity NPC19388
0.9625 High Similarity NPC240431
0.9625 High Similarity NPC311830
0.9625 High Similarity NPC22832
0.9623 High Similarity NPC189142
0.9623 High Similarity NPC77660
0.9578 High Similarity NPC473073
0.9578 High Similarity NPC473071
0.9573 High Similarity NPC294629
0.9573 High Similarity NPC198199
0.9571 High Similarity NPC117260
0.9571 High Similarity NPC476405
0.9571 High Similarity NPC153755
0.9571 High Similarity NPC256760
0.9568 High Similarity NPC52382
0.9568 High Similarity NPC270578
0.9568 High Similarity NPC105283
0.9565 High Similarity NPC135599
0.9565 High Similarity NPC254306
0.9565 High Similarity NPC236934
0.9565 High Similarity NPC328940
0.9565 High Similarity NPC5778
0.9565 High Similarity NPC113968
0.9565 High Similarity NPC277174
0.9565 High Similarity NPC73855
0.9563 High Similarity NPC88023
0.9563 High Similarity NPC222936
0.9563 High Similarity NPC168822
0.9563 High Similarity NPC243930
0.9563 High Similarity NPC284960
0.9563 High Similarity NPC309025
0.9563 High Similarity NPC29830
0.9563 High Similarity NPC19709
0.9521 High Similarity NPC470446
0.9521 High Similarity NPC470445
0.9521 High Similarity NPC470449
0.9521 High Similarity NPC470447
0.9521 High Similarity NPC470718
0.9521 High Similarity NPC473072
0.9515 High Similarity NPC473862
0.9512 High Similarity NPC42773
0.9512 High Similarity NPC101026
0.9512 High Similarity NPC204693
0.9512 High Similarity NPC4390
0.9512 High Similarity NPC21666
0.9512 High Similarity NPC45522
0.9512 High Similarity NPC24043
0.9512 High Similarity NPC169977
0.9512 High Similarity NPC208668
0.9509 High Similarity NPC116864
0.9509 High Similarity NPC235260
0.9509 High Similarity NPC20505
0.9509 High Similarity NPC155763
0.9509 High Similarity NPC177731
0.9509 High Similarity NPC150767
0.9509 High Similarity NPC79056
0.9509 High Similarity NPC78734
0.9509 High Similarity NPC244776
0.9509 High Similarity NPC105095
0.9509 High Similarity NPC44328
0.9506 High Similarity NPC229729
0.9506 High Similarity NPC45400
0.9506 High Similarity NPC58716
0.9506 High Similarity NPC146792
0.9506 High Similarity NPC45618
0.9503 High Similarity NPC475497
0.9503 High Similarity NPC15358
0.9503 High Similarity NPC475366
0.9503 High Similarity NPC284277
0.95 High Similarity NPC473043
0.9497 High Similarity NPC136761
0.9464 High Similarity NPC470717
0.9464 High Similarity NPC148710
0.9464 High Similarity NPC25946
0.9464 High Similarity NPC460984
0.9464 High Similarity NPC470720
0.9464 High Similarity NPC470451
0.9464 High Similarity NPC21359
0.9464 High Similarity NPC470455
0.9464 High Similarity NPC470713
0.9458 High Similarity NPC139571
0.9458 High Similarity NPC217520
0.9458 High Similarity NPC113836
0.9458 High Similarity NPC253521
0.9458 High Similarity NPC120952
0.9458 High Similarity NPC37668
0.9455 High Similarity NPC135277
0.9455 High Similarity NPC49344
0.9455 High Similarity NPC43211
0.9455 High Similarity NPC223426
0.9455 High Similarity NPC81042
0.9455 High Similarity NPC101191
0.9455 High Similarity NPC214621
0.9455 High Similarity NPC210094
0.9455 High Similarity NPC34267
0.9455 High Similarity NPC477848
0.9455 High Similarity NPC237435
0.9455 High Similarity NPC115760
0.9451 High Similarity NPC245452
0.9451 High Similarity NPC190003
0.9451 High Similarity NPC175107
0.9448 High Similarity NPC226294

  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 NPC285197 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
0.9814 High Similarity NPD6797 Phase 2
0.9753 High Similarity NPD7251 Discontinued
0.9752 High Similarity NPD7472 Approved
0.9693 High Similarity NPD7808 Phase 3
0.9689 High Similarity NPD7054 Approved
0.9509 High Similarity NPD7074 Phase 3
0.9455 High Similarity NPD4338 Clinical (unspecified phase)
0.9268 High Similarity NPD3818 Discontinued
0.9264 High Similarity NPD6168 Clinical (unspecified phase)
0.9264 High Similarity NPD6167 Clinical (unspecified phase)
0.9264 High Similarity NPD6166 Phase 2
0.913 High Similarity NPD4381 Clinical (unspecified phase)
0.9096 High Similarity NPD7804 Clinical (unspecified phase)
0.8882 High Similarity NPD1934 Approved
0.8773 High Similarity NPD3817 Phase 2
0.8742 High Similarity NPD1512 Approved
0.8712 High Similarity NPD2801 Approved
0.8712 High Similarity NPD2393 Clinical (unspecified phase)
0.8655 High Similarity NPD7993 Clinical (unspecified phase)
0.8616 High Similarity NPD1511 Approved
0.8606 High Similarity NPD3882 Suspended
0.8528 High Similarity NPD4380 Phase 2
0.8494 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD7075 Discontinued
0.8323 Intermediate Similarity NPD5402 Approved
0.8286 Intermediate Similarity NPD6559 Discontinued
0.8232 Intermediate Similarity NPD5403 Approved
0.8221 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD6801 Discontinued
0.8182 Intermediate Similarity NPD1653 Approved
0.8155 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD5494 Approved
0.8125 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.811 Intermediate Similarity NPD5401 Approved
0.8075 Intermediate Similarity NPD1549 Phase 2
0.8057 Intermediate Similarity NPD3751 Discontinued
0.8049 Intermediate Similarity NPD6799 Approved
0.8047 Intermediate Similarity NPD1465 Phase 2
0.8035 Intermediate Similarity NPD3787 Discontinued
0.7989 Intermediate Similarity NPD8313 Approved
0.7989 Intermediate Similarity NPD8312 Approved
0.7978 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7977 Intermediate Similarity NPD6959 Discontinued
0.7955 Intermediate Similarity NPD7228 Approved
0.791 Intermediate Similarity NPD5844 Phase 1
0.7895 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD1510 Phase 2
0.7877 Intermediate Similarity NPD7685 Pre-registration
0.784 Intermediate Similarity NPD2796 Approved
0.7836 Intermediate Similarity NPD7819 Suspended
0.7829 Intermediate Similarity NPD6232 Discontinued
0.7824 Intermediate Similarity NPD7411 Suspended
0.7798 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD7473 Discontinued
0.7784 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD7199 Phase 2
0.7765 Intermediate Similarity NPD6599 Discontinued
0.775 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD1613 Approved
0.7733 Intermediate Similarity NPD8455 Phase 2
0.7705 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD6776 Approved
0.7684 Intermediate Similarity NPD6782 Approved
0.7684 Intermediate Similarity NPD6781 Approved
0.7684 Intermediate Similarity NPD6778 Approved
0.7684 Intermediate Similarity NPD6777 Approved
0.7684 Intermediate Similarity NPD6779 Approved
0.7684 Intermediate Similarity NPD6780 Approved
0.7683 Intermediate Similarity NPD7266 Discontinued
0.7676 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD6234 Discontinued
0.7657 Intermediate Similarity NPD919 Approved
0.7641 Intermediate Similarity NPD8151 Discontinued
0.764 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD6190 Approved
0.7584 Intermediate Similarity NPD3926 Phase 2
0.7582 Intermediate Similarity NPD7240 Approved
0.7572 Intermediate Similarity NPD37 Approved
0.7571 Intermediate Similarity NPD1247 Approved
0.7565 Intermediate Similarity NPD7698 Approved
0.7565 Intermediate Similarity NPD7696 Phase 3
0.7565 Intermediate Similarity NPD7697 Approved
0.7565 Intermediate Similarity NPD7435 Discontinued
0.7545 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD3750 Approved
0.7543 Intermediate Similarity NPD4966 Approved
0.7543 Intermediate Similarity NPD4967 Phase 2
0.7543 Intermediate Similarity NPD4965 Approved
0.7538 Intermediate Similarity NPD7584 Approved
0.7531 Intermediate Similarity NPD1240 Approved
0.7531 Intermediate Similarity NPD943 Approved
0.753 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7701 Phase 2
0.7485 Intermediate Similarity NPD1933 Approved
0.7453 Intermediate Similarity NPD3027 Phase 3
0.7439 Intermediate Similarity NPD1607 Approved
0.7438 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7870 Phase 2
0.7436 Intermediate Similarity NPD7871 Phase 2
0.7421 Intermediate Similarity NPD6535 Approved
0.7421 Intermediate Similarity NPD6534 Approved
0.741 Intermediate Similarity NPD1551 Phase 2
0.7401 Intermediate Similarity NPD3749 Approved
0.7396 Intermediate Similarity NPD7700 Phase 2
0.7396 Intermediate Similarity NPD7699 Phase 2
0.7387 Intermediate Similarity NPD7783 Phase 2
0.7387 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD230 Phase 1
0.7349 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7768 Phase 2
0.7344 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7874 Approved
0.7337 Intermediate Similarity NPD4628 Phase 3
0.7301 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD7801 Approved
0.7273 Intermediate Similarity NPD447 Suspended
0.7259 Intermediate Similarity NPD8320 Phase 1
0.7259 Intermediate Similarity NPD8319 Approved
0.7246 Intermediate Similarity NPD3748 Approved
0.7245 Intermediate Similarity NPD6823 Phase 2
0.7202 Intermediate Similarity NPD2935 Discontinued
0.7196 Intermediate Similarity NPD8150 Discontinued
0.7196 Intermediate Similarity NPD8434 Phase 2
0.7179 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD1091 Approved
0.7168 Intermediate Similarity NPD2532 Approved
0.7168 Intermediate Similarity NPD2534 Approved
0.7168 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD2533 Approved
0.715 Intermediate Similarity NPD7585 Approved
0.7143 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD7680 Approved
0.7102 Intermediate Similarity NPD7458 Discontinued
0.71 Intermediate Similarity NPD7583 Approved
0.7086 Intermediate Similarity NPD920 Approved
0.7081 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD6674 Discontinued
0.7076 Intermediate Similarity NPD2800 Approved
0.7074 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD4363 Phase 3
0.7062 Intermediate Similarity NPD4360 Phase 2
0.7059 Intermediate Similarity NPD5953 Discontinued
0.7052 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7033 Discontinued
0.7012 Intermediate Similarity NPD9494 Approved
0.7011 Intermediate Similarity NPD7390 Discontinued
0.701 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD6213 Phase 3
0.701 Intermediate Similarity NPD6212 Phase 3
0.7006 Intermediate Similarity NPD3226 Approved
0.7 Intermediate Similarity NPD6099 Approved
0.7 Intermediate Similarity NPD6100 Approved
0.6994 Remote Similarity NPD1203 Approved
0.6988 Remote Similarity NPD6798 Discontinued
0.6988 Remote Similarity NPD2313 Discontinued
0.6986 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6983 Remote Similarity NPD6844 Discontinued
0.6977 Remote Similarity NPD1243 Approved
0.6977 Remote Similarity NPD1652 Phase 2
0.6975 Remote Similarity NPD4379 Clinical (unspecified phase)
0.697 Remote Similarity NPD4908 Phase 1
0.697 Remote Similarity NPD6832 Phase 2
0.6957 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6952 Remote Similarity NPD7286 Phase 2
0.6951 Remote Similarity NPD2798 Approved
0.6946 Remote Similarity NPD6233 Phase 2
0.6923 Remote Similarity NPD6651 Approved
0.6918 Remote Similarity NPD1548 Phase 1
0.691 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6906 Remote Similarity NPD5353 Approved
0.6886 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6881 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6864 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6355 Discontinued
0.6864 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6864 Remote Similarity NPD5124 Phase 1
0.686 Remote Similarity NPD2346 Discontinued
0.686 Remote Similarity NPD2344 Approved
0.6852 Remote Similarity NPD1610 Phase 2
0.6842 Remote Similarity NPD2799 Discontinued
0.6839 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6829 Remote Similarity NPD3225 Approved
0.6828 Remote Similarity NPD5242 Approved
0.6816 Remote Similarity NPD5006 Approved
0.6816 Remote Similarity NPD5005 Approved
0.6811 Remote Similarity NPD8127 Discontinued
0.681 Remote Similarity NPD9269 Phase 2
0.6809 Remote Similarity NPD2163 Approved
0.6806 Remote Similarity NPD7549 Discontinued
0.6804 Remote Similarity NPD6841 Approved
0.6804 Remote Similarity NPD6843 Phase 3
0.6804 Remote Similarity NPD6842 Approved

  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