Structure

Physi-Chem Properties

Molecular Weight:  594.16
Volume:  543.527
LogP:  1.072
LogD:  0.192
LogS:  -4.935
# Rotatable Bonds:  5
TPSA:  249.2
# H-Bond Aceptor:  15
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.166
Synthetic Accessibility Score:  4.77
Fsp3:  0.444
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.412
MDCK Permeability:  2.386800952081103e-05
Pgp-inhibitor:  0.017
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.812
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  88.75296020507812%
Volume Distribution (VD):  0.678
Pgp-substrate:  15.175369262695312%

ADMET: Metabolism

CYP1A2-inhibitor:  0.156
CYP1A2-substrate:  0.064
CYP2C19-inhibitor:  0.043
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.048
CYP2C9-substrate:  0.324
CYP2D6-inhibitor:  0.112
CYP2D6-substrate:  0.143
CYP3A4-inhibitor:  0.079
CYP3A4-substrate:  0.004

ADMET: Excretion

Clearance (CL):  1.8
Half-life (T1/2):  0.7

ADMET: Toxicity

hERG Blockers:  0.044
Human Hepatotoxicity (H-HT):  0.145
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.842
Rat Oral Acute Toxicity:  0.045
Maximum Recommended Daily Dose:  0.028
Skin Sensitization:  0.931
Carcinogencity:  0.036
Eye Corrosion:  0.003
Eye Irritation:  0.538
Respiratory Toxicity:  0.054

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

  Natural Product: NPC95866

Natural Product ID:  NPC95866
Common Name*:   Quercetin-3-O-Alpha-L-Rhamnosyl-(1->2)-O-Alpha-L-Rhamnoside
IUPAC Name:   3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:  
Standard InCHIKey:  SEEGVLYKLLCFTK-AQNZCLFOSA-N
Standard InCHI:  InChI=1S/C27H30O15/c1-8-17(32)20(35)22(37)26(38-8)42-25-21(36)18(33)9(2)39-27(25)41-24-19(34)16-14(31)6-11(28)7-15(16)40-23(24)10-3-4-12(29)13(30)5-10/h3-9,17-18,20-22,25-33,35-37H,1-2H3/t8-,9-,17-,18-,20+,21+,22+,25+,26-,27-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H]([C@H]([C@H](C)O[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL551120
PubChem CID:   10698716
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
NPO19975 Pycnandra acuminata Species Sapotaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2007.07.001]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota seeds n.a. n.a. PMID[12762787]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[12762809]
NPO6412 Echinacea pallida Species Asteraceae Eukaryota root n.a. n.a. PMID[15921428]
NPO594 Alpinia densespicata Species Staphylinidae Eukaryota n.a. n.a. n.a. PMID[19555124]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO633 Mesembryanthemum expansum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6856.1 Artemisia ludoviciana subsp. mexicana Subspecies Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO633 Mesembryanthemum expansum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10970 Osmorhiza aristata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6861 Galium dasypodum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8129 Inocybe geophylla Species Inocybaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO218 Acer carpinifolium Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7874 Helichrysum lepidissimum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11506 Stipa vaseyi Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26095 Hypericum revolutum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4322 Scabiosa succisa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO633 Mesembryanthemum expansum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5534 Alternaria kikuchiana Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6856.1 Artemisia ludoviciana subsp. mexicana Subspecies Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19975 Pycnandra acuminata Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8609 Hopea utilis Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1695 Monascus pilosus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10010 Evernia vulpina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6412 Echinacea pallida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12118 Cleistopholis staudtii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11339 Litsea salicifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12602 Leuzea centauroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO594 Alpinia densespicata Species Staphylinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO940 Vernonia anisochaetoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12828 Dysidea tupha Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4759 Helleborus multifidus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 32900.0 nM PMID[488715]
NPT113 Cell Line RAW264.7 Mus musculus Activity > 80.0 % PMID[488715]
NPT1 Others Radical scavenging activity ED50 = 16.6 uM PMID[488715]

☑ 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 NPC95866 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 NPC176740
0.9938 High Similarity NPC33054
0.9938 High Similarity NPC471748
0.9938 High Similarity NPC471725
0.9938 High Similarity NPC155877
0.9938 High Similarity NPC134532
0.9938 High Similarity NPC203259
0.9875 High Similarity NPC156869
0.9875 High Similarity NPC136042
0.9875 High Similarity NPC254855
0.9875 High Similarity NPC259896
0.9875 High Similarity NPC255157
0.9875 High Similarity NPC67326
0.9875 High Similarity NPC67105
0.9875 High Similarity NPC29958
0.9874 High Similarity NPC52550
0.9874 High Similarity NPC127546
0.9874 High Similarity NPC223424
0.9874 High Similarity NPC317489
0.9874 High Similarity NPC173637
0.9874 High Similarity NPC84362
0.9815 High Similarity NPC16194
0.9815 High Similarity NPC476472
0.9815 High Similarity NPC294629
0.9815 High Similarity NPC220173
0.9815 High Similarity NPC473327
0.9815 High Similarity NPC294815
0.9815 High Similarity NPC19108
0.9814 High Similarity NPC26230
0.9814 High Similarity NPC60735
0.9812 High Similarity NPC52382
0.9812 High Similarity NPC120099
0.9812 High Similarity NPC219904
0.9812 High Similarity NPC227508
0.9812 High Similarity NPC203050
0.9812 High Similarity NPC223747
0.9812 High Similarity NPC270578
0.9812 High Similarity NPC225434
0.9811 High Similarity NPC88789
0.9811 High Similarity NPC56077
0.9811 High Similarity NPC277174
0.9811 High Similarity NPC115674
0.9811 High Similarity NPC73855
0.9811 High Similarity NPC179950
0.9811 High Similarity NPC145038
0.9811 High Similarity NPC253662
0.9811 High Similarity NPC281131
0.9811 High Similarity NPC135599
0.9811 High Similarity NPC276222
0.9811 High Similarity NPC274618
0.9811 High Similarity NPC118284
0.9811 High Similarity NPC308404
0.9811 High Similarity NPC210073
0.9811 High Similarity NPC113968
0.9811 High Similarity NPC328940
0.9755 High Similarity NPC89127
0.9755 High Similarity NPC122467
0.9755 High Similarity NPC470949
0.9755 High Similarity NPC14187
0.9755 High Similarity NPC202908
0.9755 High Similarity NPC292019
0.9755 High Similarity NPC471669
0.9755 High Similarity NPC65563
0.9752 High Similarity NPC206123
0.9752 High Similarity NPC285197
0.9752 High Similarity NPC116864
0.9752 High Similarity NPC244776
0.975 High Similarity NPC275454
0.975 High Similarity NPC92565
0.975 High Similarity NPC265530
0.975 High Similarity NPC160156
0.975 High Similarity NPC226304
0.975 High Similarity NPC325555
0.9748 High Similarity NPC19388
0.9748 High Similarity NPC277205
0.9748 High Similarity NPC55786
0.9748 High Similarity NPC240431
0.9695 High Similarity NPC89052
0.9695 High Similarity NPC173837
0.9695 High Similarity NPC251417
0.9693 High Similarity NPC253685
0.9691 High Similarity NPC245452
0.9691 High Similarity NPC175107
0.9691 High Similarity NPC153755
0.9691 High Similarity NPC190003
0.9689 High Similarity NPC209296
0.9689 High Similarity NPC195257
0.9688 High Similarity NPC21100
0.9688 High Similarity NPC197285
0.9688 High Similarity NPC8856
0.9686 High Similarity NPC19709
0.9636 High Similarity NPC241423
0.9636 High Similarity NPC192539
0.9636 High Similarity NPC473682
0.9636 High Similarity NPC470444
0.9636 High Similarity NPC470443
0.9636 High Similarity NPC110941
0.9636 High Similarity NPC473571
0.9636 High Similarity NPC126784
0.9634 High Similarity NPC473862
0.9634 High Similarity NPC219043
0.9634 High Similarity NPC48984
0.9634 High Similarity NPC169733
0.9634 High Similarity NPC8573
0.9632 High Similarity NPC21666
0.9632 High Similarity NPC42773
0.9632 High Similarity NPC169977
0.9632 High Similarity NPC45522
0.9632 High Similarity NPC24043
0.9632 High Similarity NPC4390
0.9632 High Similarity NPC101026
0.963 High Similarity NPC51326
0.963 High Similarity NPC150767
0.963 High Similarity NPC235260
0.963 High Similarity NPC231194
0.963 High Similarity NPC20505
0.963 High Similarity NPC155763
0.963 High Similarity NPC78734
0.9625 High Similarity NPC311830
0.9625 High Similarity NPC22832
0.9623 High Similarity NPC77660
0.9623 High Similarity NPC189142
0.9623 High Similarity NPC473043
0.9578 High Similarity NPC473073
0.9578 High Similarity NPC473071
0.9576 High Similarity NPC217520
0.9576 High Similarity NPC139571
0.9576 High Similarity NPC35167
0.9573 High Similarity NPC223426
0.9573 High Similarity NPC81042
0.9573 High Similarity NPC214621
0.9573 High Similarity NPC34267
0.9571 High Similarity NPC117260
0.9571 High Similarity NPC476405
0.9571 High Similarity NPC256760
0.9568 High Similarity NPC86008
0.9568 High Similarity NPC138927
0.9568 High Similarity NPC43587
0.9565 High Similarity NPC67037
0.9565 High Similarity NPC236934
0.9565 High Similarity NPC5778
0.9565 High Similarity NPC255615
0.9563 High Similarity NPC222936
0.9563 High Similarity NPC270335
0.9563 High Similarity NPC284960
0.9563 High Similarity NPC88023
0.9563 High Similarity NPC243930
0.9563 High Similarity NPC168822
0.9563 High Similarity NPC309025
0.9563 High Similarity NPC29830
0.9563 High Similarity NPC191306
0.956 High Similarity NPC163242
0.956 High Similarity NPC253788
0.956 High Similarity NPC276377
0.956 High Similarity NPC173582
0.956 High Similarity NPC473438
0.956 High Similarity NPC476215
0.956 High Similarity NPC246943
0.956 High Similarity NPC215710
0.956 High Similarity NPC265885
0.956 High Similarity NPC139320
0.956 High Similarity NPC116458
0.956 High Similarity NPC249281
0.956 High Similarity NPC181465
0.9521 High Similarity NPC241781
0.9521 High Similarity NPC162394
0.9521 High Similarity NPC470445
0.9521 High Similarity NPC470449
0.9521 High Similarity NPC470447
0.9521 High Similarity NPC470446
0.9521 High Similarity NPC156785
0.9521 High Similarity NPC473072
0.9515 High Similarity NPC198324
0.9515 High Similarity NPC144097
0.9515 High Similarity NPC61904
0.9515 High Similarity NPC472385
0.9512 High Similarity NPC204693
0.9512 High Similarity NPC208668
0.9509 High Similarity NPC245014
0.9509 High Similarity NPC177731
0.9509 High Similarity NPC84265
0.9509 High Similarity NPC79056
0.9509 High Similarity NPC105095
0.9509 High Similarity NPC282987
0.9509 High Similarity NPC218488
0.9509 High Similarity NPC44328
0.9506 High Similarity NPC48640
0.9506 High Similarity NPC149244
0.9506 High Similarity NPC229729
0.9503 High Similarity NPC475366
0.9503 High Similarity NPC475497
0.9503 High Similarity NPC284277
0.9503 High Similarity NPC34531
0.95 High Similarity NPC300537
0.95 High Similarity NPC240306
0.95 High Similarity NPC127782
0.9497 High Similarity NPC187379
0.9497 High Similarity NPC304741
0.9497 High Similarity NPC470405
0.9497 High Similarity NPC471079

  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 NPC95866 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
0.9938 High Similarity NPD6797 Phase 2
0.9876 High Similarity NPD7251 Discontinued
0.9693 High Similarity NPD7808 Phase 3
0.9689 High Similarity NPD7054 Approved
0.963 High Similarity NPD7472 Approved
0.9509 High Similarity NPD7074 Phase 3
0.9455 High Similarity NPD4338 Clinical (unspecified phase)
0.9329 High Similarity NPD7804 Clinical (unspecified phase)
0.9264 High Similarity NPD6167 Clinical (unspecified phase)
0.9264 High Similarity NPD6166 Phase 2
0.9264 High Similarity NPD6168 Clinical (unspecified phase)
0.9152 High Similarity NPD3818 Discontinued
0.913 High Similarity NPD4381 Clinical (unspecified phase)
0.8889 High Similarity NPD3817 Phase 2
0.8882 High Similarity NPD1934 Approved
0.8827 High Similarity NPD2393 Clinical (unspecified phase)
0.8742 High Similarity NPD1512 Approved
0.872 High Similarity NPD3882 Suspended
0.8712 High Similarity NPD2801 Approved
0.8616 High Similarity NPD1511 Approved
0.8554 High Similarity NPD7075 Discontinued
0.8547 High Similarity NPD7993 Clinical (unspecified phase)
0.8528 High Similarity NPD4380 Phase 2
0.8494 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD5402 Approved
0.8424 Intermediate Similarity NPD6801 Discontinued
0.8391 Intermediate Similarity NPD6559 Discontinued
0.8373 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD5403 Approved
0.8333 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8272 Intermediate Similarity NPD6799 Approved
0.8221 Intermediate Similarity NPD5401 Approved
0.8177 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8161 Intermediate Similarity NPD3751 Discontinued
0.814 Intermediate Similarity NPD3787 Discontinued
0.8129 Intermediate Similarity NPD5494 Approved
0.8125 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8081 Intermediate Similarity NPD6959 Discontinued
0.8075 Intermediate Similarity NPD1549 Phase 2
0.8072 Intermediate Similarity NPD1653 Approved
0.8 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD6599 Discontinued
0.7955 Intermediate Similarity NPD7228 Approved
0.795 Intermediate Similarity NPD2796 Approved
0.7941 Intermediate Similarity NPD7819 Suspended
0.7941 Intermediate Similarity NPD1465 Phase 2
0.7929 Intermediate Similarity NPD7411 Suspended
0.791 Intermediate Similarity NPD5844 Phase 1
0.7892 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7889 Intermediate Similarity NPD8312 Approved
0.7889 Intermediate Similarity NPD8313 Approved
0.7888 Intermediate Similarity NPD1510 Phase 2
0.7886 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD7685 Pre-registration
0.7829 Intermediate Similarity NPD6232 Discontinued
0.7798 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD7473 Discontinued
0.7791 Intermediate Similarity NPD7266 Discontinued
0.7778 Intermediate Similarity NPD6777 Approved
0.7778 Intermediate Similarity NPD6779 Approved
0.7778 Intermediate Similarity NPD6778 Approved
0.7778 Intermediate Similarity NPD6776 Approved
0.7778 Intermediate Similarity NPD6781 Approved
0.7778 Intermediate Similarity NPD6782 Approved
0.7778 Intermediate Similarity NPD6780 Approved
0.7771 Intermediate Similarity NPD7199 Phase 2
0.7759 Intermediate Similarity NPD919 Approved
0.775 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD1613 Approved
0.7749 Intermediate Similarity NPD7435 Discontinued
0.774 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD6190 Approved
0.7705 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD1247 Approved
0.7657 Intermediate Similarity NPD6234 Discontinued
0.7656 Intermediate Similarity NPD7698 Approved
0.7656 Intermediate Similarity NPD7697 Approved
0.7656 Intermediate Similarity NPD7696 Phase 3
0.7651 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7641 Intermediate Similarity NPD8151 Discontinued
0.764 Intermediate Similarity NPD1240 Approved
0.7636 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD8455 Phase 2
0.7629 Intermediate Similarity NPD7584 Approved
0.759 Intermediate Similarity NPD7701 Phase 2
0.7584 Intermediate Similarity NPD3926 Phase 2
0.7572 Intermediate Similarity NPD37 Approved
0.7546 Intermediate Similarity NPD1607 Approved
0.7545 Intermediate Similarity NPD3750 Approved
0.7543 Intermediate Similarity NPD4965 Approved
0.7543 Intermediate Similarity NPD4966 Approved
0.7543 Intermediate Similarity NPD4967 Phase 2
0.7531 Intermediate Similarity NPD943 Approved
0.7526 Intermediate Similarity NPD7871 Phase 2
0.7526 Intermediate Similarity NPD7870 Phase 2
0.7526 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD7874 Approved
0.7513 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD6535 Approved
0.7513 Intermediate Similarity NPD6534 Approved
0.75 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7699 Phase 2
0.7487 Intermediate Similarity NPD7700 Phase 2
0.7486 Intermediate Similarity NPD7240 Approved
0.7485 Intermediate Similarity NPD230 Phase 1
0.7485 Intermediate Similarity NPD1933 Approved
0.7475 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7783 Phase 2
0.7453 Intermediate Similarity NPD3027 Phase 3
0.7443 Intermediate Similarity NPD7768 Phase 2
0.744 Intermediate Similarity NPD4628 Phase 3
0.7438 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD8319 Approved
0.7436 Intermediate Similarity NPD8320 Phase 1
0.741 Intermediate Similarity NPD1551 Phase 2
0.7407 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD3749 Approved
0.7387 Intermediate Similarity NPD7801 Approved
0.7349 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6823 Phase 2
0.7305 Intermediate Similarity NPD2935 Discontinued
0.7287 Intermediate Similarity NPD8150 Discontinued
0.7278 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD447 Suspended
0.7267 Intermediate Similarity NPD2534 Approved
0.7267 Intermediate Similarity NPD2532 Approved
0.7267 Intermediate Similarity NPD2533 Approved
0.7253 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD3748 Approved
0.7236 Intermediate Similarity NPD7585 Approved
0.72 Intermediate Similarity NPD7458 Discontinued
0.7196 Intermediate Similarity NPD8434 Phase 2
0.7195 Intermediate Similarity NPD6798 Discontinued
0.7186 Intermediate Similarity NPD7583 Approved
0.7184 Intermediate Similarity NPD920 Approved
0.7179 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD2800 Approved
0.717 Intermediate Similarity NPD1091 Approved
0.7168 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6233 Phase 2
0.7151 Intermediate Similarity NPD5953 Discontinued
0.715 Intermediate Similarity NPD4363 Phase 3
0.715 Intermediate Similarity NPD4360 Phase 2
0.715 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7033 Discontinued
0.7143 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD7680 Approved
0.711 Intermediate Similarity NPD7390 Discontinued
0.7102 Intermediate Similarity NPD3226 Approved
0.7101 Intermediate Similarity NPD6100 Approved
0.7101 Intermediate Similarity NPD6099 Approved
0.7098 Intermediate Similarity NPD6213 Phase 3
0.7098 Intermediate Similarity NPD6212 Phase 3
0.7098 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD6844 Discontinued
0.7076 Intermediate Similarity NPD6674 Discontinued
0.7076 Intermediate Similarity NPD1652 Phase 2
0.7076 Intermediate Similarity NPD1243 Approved
0.7073 Intermediate Similarity NPD4908 Phase 1
0.7073 Intermediate Similarity NPD6832 Phase 2
0.7069 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6355 Discontinued
0.7055 Intermediate Similarity NPD2798 Approved
0.7052 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD7286 Phase 2
0.7024 Intermediate Similarity NPD6651 Approved
0.7012 Intermediate Similarity NPD9494 Approved
0.6994 Remote Similarity NPD1203 Approved
0.6988 Remote Similarity NPD2313 Discontinued
0.6988 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6975 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6965 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6964 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6964 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6964 Remote Similarity NPD5124 Phase 1
0.6959 Remote Similarity NPD2346 Discontinued
0.6959 Remote Similarity NPD2344 Approved
0.6957 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6941 Remote Similarity NPD2799 Discontinued
0.6936 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6918 Remote Similarity NPD1548 Phase 1
0.691 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6906 Remote Similarity NPD5353 Approved
0.6905 Remote Similarity NPD4060 Phase 1
0.6898 Remote Similarity NPD2163 Approved
0.6886 Remote Similarity NPD3268 Approved
0.6882 Remote Similarity NPD2403 Approved
0.6875 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6865 Remote Similarity NPD5711 Approved
0.6865 Remote Similarity NPD5710 Approved
0.686 Remote Similarity NPD7930 Approved
0.6852 Remote Similarity NPD1610 Phase 2
0.6852 Remote Similarity NPD422 Phase 1
0.6845 Remote Similarity NPD4062 Phase 3
0.6842 Remote Similarity NPD1509 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