Structure

Physi-Chem Properties

Molecular Weight:  698.27
Volume:  708.839
LogP:  5.669
LogD:  3.912
LogS:  -4.448
# Rotatable Bonds:  14
TPSA:  140.73
# H-Bond Aceptor:  11
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.199
Synthetic Accessibility Score:  5.791
Fsp3:  0.425
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
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:  -5.253
MDCK Permeability:  2.4978799046948552e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.994
30% Bioavailability (F30%):  0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  99.47856140136719%
Volume Distribution (VD):  2.129
Pgp-substrate:  5.918274402618408%

ADMET: Metabolism

CYP1A2-inhibitor:  0.074
CYP1A2-substrate:  0.02
CYP2C19-inhibitor:  0.378
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.436
CYP2C9-substrate:  0.051
CYP2D6-inhibitor:  0.585
CYP2D6-substrate:  0.032
CYP3A4-inhibitor:  0.64
CYP3A4-substrate:  0.313

ADMET: Excretion

Clearance (CL):  5.677
Half-life (T1/2):  0.717

ADMET: Toxicity

hERG Blockers:  0.664
Human Hepatotoxicity (H-HT):  0.961
Drug-inuced Liver Injury (DILI):  0.992
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.023
Maximum Recommended Daily Dose:  0.05
Skin Sensitization:  0.63
Carcinogencity:  0.203
Eye Corrosion:  0.003
Eye Irritation:  0.6
Respiratory Toxicity:  0.262

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Similar NPs/Drugs  

  Natural Product: NPC139060

Natural Product ID:  NPC139060
Common Name*:   Kaempferol 7-O-(2-E-P-Coumaroyl-Alpha-L-Rhamnoside)
IUPAC Name:   [(2S,3R,4R,5R,6S)-2-[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  XUUODWXANHZAFB-OKOXDJDNSA-N
Standard InCHI:  InChI=1S/C30H26O12/c1-14-24(35)26(37)29(42-22(34)11-4-15-2-7-17(31)8-3-15)30(39-14)40-19-12-20(33)23-21(13-19)41-28(27(38)25(23)36)16-5-9-18(32)10-6-16/h2-14,24,26,29-33,35,37-38H,1H3/b11-4+/t14-,24-,26+,29+,30-/m0/s1
SMILES:  Oc1ccc(cc1)/C=C/C(=O)O[C@H]1[C@H](Oc2cc(O)c3c(c2)oc(c(c3=O)O)c2ccc(cc2)O)O[C@H]([C@@H]([C@H]1O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501872
PubChem CID:   11678667
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
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[10843584]
NPO27252 Iochroma australe Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12027740]
NPO26782 Dendrilla membranosa Species Darwinellidae Eukaryota n.a. antarctic n.a. PMID[15270575]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[15497934]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. fruit n.a. PMID[16378372]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. flower n.a. PMID[16378372]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[30407007]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29051 Ranunculus acris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25997 Senecio rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14466 Penicillium olsonii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19823 Vicia benghalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25952 Lastrea thelypteris n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26980 Halocarpus biformis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25926 Tephrosia pumila Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25873 Thaminophyllum multiflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26109 Pilocarpus spicatus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26727 Eremocarpus setiger n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26625 Stichopus chloronotus Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24378 Osmanthus heterophyllus Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26408 Melanophryniscus moreirae Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26352 Heuchera cylindrica Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26678 Calea pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3346 Piper sanctum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26535 Balanus glandula Species Balanidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11845 Petrorhagia dubia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25849 Streptomyces lomondensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18292 Guarea trichilioides Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25793 Gremmeniella abietina Species Helotiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29051 Ranunculus acris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26289 Lecidella chodati Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26952 Cineraria geifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26053 Pluchea suaveolens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26377 Amelanchier vulgaris Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26453 Prunus lusitanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27377 Diaporthe helianthi Species Diaporthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26186 Stereocaulon leprocauloides Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26563 Alectoria japonica Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26884 Helichrysum davenportii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26026 Vitis silvestris Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25741 Aster ageratoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13781 Eremostachys moluccelloides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26430 Aplysina laevis Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7214 Bufotes viridis Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27252 Iochroma australe Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26782 Dendrilla membranosa Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26754 Stevia connata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26078 Mussaenda parviflora Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2344 Carlina acanthifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26244 Panax papyrifer Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO137 Nepeta multifida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26135 Walsura tubulata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26213 Tephrosia vogelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26903 Plectranthus purpuratus Species Lamiaceae 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
NPT140 Organism Artemia Artemia LC50 = 570000.0 nM PMID[509389]

☑ 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 NPC139060 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
0.9935 High Similarity NPC80068
0.9872 High Similarity NPC85751
0.9872 High Similarity NPC19240
0.9872 High Similarity NPC205824
0.9872 High Similarity NPC129264
0.9806 High Similarity NPC477628
0.9806 High Similarity NPC210961
0.9806 High Similarity NPC477629
0.9806 High Similarity NPC472994
0.9806 High Similarity NPC270675
0.9806 High Similarity NPC195685
0.9748 High Similarity NPC188815
0.9688 High Similarity NPC101399
0.9688 High Similarity NPC217822
0.9688 High Similarity NPC221288
0.9688 High Similarity NPC474522
0.9688 High Similarity NPC11847
0.9679 High Similarity NPC470125
0.9679 High Similarity NPC129217
0.9679 High Similarity NPC259957
0.9679 High Similarity NPC224530
0.9679 High Similarity NPC48093
0.9679 High Similarity NPC216496
0.9679 High Similarity NPC159579
0.9679 High Similarity NPC85707
0.9625 High Similarity NPC470712
0.9625 High Similarity NPC218161
0.9625 High Similarity NPC469344
0.9625 High Similarity NPC280642
0.9625 High Similarity NPC164704
0.9625 High Similarity NPC96605
0.9618 High Similarity NPC472876
0.9618 High Similarity NPC27942
0.9615 High Similarity NPC187379
0.9613 High Similarity NPC182634
0.9613 High Similarity NPC108831
0.9565 High Similarity NPC470714
0.9565 High Similarity NPC470716
0.9565 High Similarity NPC470715
0.956 High Similarity NPC64425
0.956 High Similarity NPC260504
0.956 High Similarity NPC473278
0.956 High Similarity NPC89809
0.9557 High Similarity NPC121703
0.9554 High Similarity NPC276377
0.9554 High Similarity NPC215710
0.9554 High Similarity NPC181465
0.9554 High Similarity NPC473438
0.9554 High Similarity NPC163242
0.9554 High Similarity NPC265885
0.9554 High Similarity NPC249281
0.9554 High Similarity NPC476215
0.9554 High Similarity NPC101636
0.9554 High Similarity NPC246943
0.9554 High Similarity NPC116458
0.9554 High Similarity NPC253788
0.9554 High Similarity NPC139320
0.9554 High Similarity NPC282169
0.9554 High Similarity NPC173582
0.9551 High Similarity NPC104677
0.9551 High Similarity NPC320283
0.9551 High Similarity NPC111929
0.9551 High Similarity NPC41121
0.9551 High Similarity NPC472459
0.9548 High Similarity NPC307938
0.9548 High Similarity NPC323593
0.9548 High Similarity NPC203500
0.9509 High Similarity NPC231787
0.9503 High Similarity NPC76047
0.9503 High Similarity NPC92815
0.9497 High Similarity NPC72016
0.9494 High Similarity NPC240306
0.9494 High Similarity NPC298171
0.949 High Similarity NPC470405
0.949 High Similarity NPC471079
0.949 High Similarity NPC136761
0.949 High Similarity NPC304741
0.9487 High Similarity NPC44931
0.9487 High Similarity NPC473512
0.9487 High Similarity NPC133671
0.9487 High Similarity NPC54802
0.9487 High Similarity NPC78263
0.9487 High Similarity NPC197304
0.9487 High Similarity NPC43638
0.9487 High Similarity NPC129827
0.9487 High Similarity NPC77672
0.9487 High Similarity NPC65003
0.9487 High Similarity NPC135391
0.9484 High Similarity NPC95090
0.9484 High Similarity NPC27408
0.9451 High Similarity NPC139571
0.9451 High Similarity NPC35167
0.9451 High Similarity NPC477895
0.9451 High Similarity NPC217520
0.9448 High Similarity NPC214621
0.9448 High Similarity NPC223426
0.9448 High Similarity NPC81042
0.9448 High Similarity NPC34267
0.943 High Similarity NPC297987
0.943 High Similarity NPC64305
0.943 High Similarity NPC170052
0.943 High Similarity NPC135846
0.943 High Similarity NPC303913
0.9427 High Similarity NPC43761
0.9427 High Similarity NPC138811
0.9427 High Similarity NPC22062
0.9427 High Similarity NPC73511
0.9427 High Similarity NPC473634
0.9423 High Similarity NPC127406
0.9419 High Similarity NPC83283
0.9419 High Similarity NPC39360
0.9419 High Similarity NPC143851
0.9419 High Similarity NPC210003
0.9419 High Similarity NPC29763
0.939 High Similarity NPC144097
0.939 High Similarity NPC61904
0.9387 High Similarity NPC472993
0.9383 High Similarity NPC277532
0.9383 High Similarity NPC175429
0.9383 High Similarity NPC209550
0.9383 High Similarity NPC138990
0.9375 High Similarity NPC135358
0.9375 High Similarity NPC287889
0.9371 High Similarity NPC150164
0.9371 High Similarity NPC131745
0.9367 High Similarity NPC473623
0.9367 High Similarity NPC153342
0.9363 High Similarity NPC313163
0.9363 High Similarity NPC156457
0.9363 High Similarity NPC258035
0.9363 High Similarity NPC6985
0.9363 High Similarity NPC161749
0.9363 High Similarity NPC60966
0.9363 High Similarity NPC197896
0.9359 High Similarity NPC99233
0.9355 High Similarity NPC88484
0.9355 High Similarity NPC259767
0.9333 High Similarity NPC253521
0.9333 High Similarity NPC258044
0.9333 High Similarity NPC267680
0.9333 High Similarity NPC293626
0.9333 High Similarity NPC113836
0.9333 High Similarity NPC37668
0.9333 High Similarity NPC217387
0.9333 High Similarity NPC196127
0.9317 High Similarity NPC11432
0.9317 High Similarity NPC221342
0.9317 High Similarity NPC189564
0.9317 High Similarity NPC142142
0.9317 High Similarity NPC186816
0.9317 High Similarity NPC262222
0.9317 High Similarity NPC476470
0.9317 High Similarity NPC68592
0.9317 High Similarity NPC256188
0.9317 High Similarity NPC203145
0.9317 High Similarity NPC12013
0.9317 High Similarity NPC298666
0.9317 High Similarity NPC477613
0.9317 High Similarity NPC32641
0.9313 High Similarity NPC66087
0.9313 High Similarity NPC179198
0.9313 High Similarity NPC278419
0.9313 High Similarity NPC183672
0.9299 High Similarity NPC295613
0.9299 High Similarity NPC206378
0.9299 High Similarity NPC170475
0.9299 High Similarity NPC473657
0.9299 High Similarity NPC45165
0.9295 High Similarity NPC106625
0.9281 High Similarity NPC241781
0.9281 High Similarity NPC156785
0.9281 High Similarity NPC162394
0.9281 High Similarity NPC36138
0.9264 High Similarity NPC116864
0.9264 High Similarity NPC244776
0.9255 High Similarity NPC289667
0.9255 High Similarity NPC76831
0.9255 High Similarity NPC292929
0.925 High Similarity NPC259834
0.925 High Similarity NPC44947
0.925 High Similarity NPC244875
0.925 High Similarity NPC475382
0.9245 High Similarity NPC142860
0.9245 High Similarity NPC246469
0.9245 High Similarity NPC271270
0.9245 High Similarity NPC97285
0.9241 High Similarity NPC288084
0.9241 High Similarity NPC122809
0.9241 High Similarity NPC23817
0.9236 High Similarity NPC97052
0.9236 High Similarity NPC169248
0.9236 High Similarity NPC39351
0.9236 High Similarity NPC72649
0.9236 High Similarity NPC26195
0.9231 High Similarity NPC259182
0.9231 High Similarity NPC121001
0.9226 High Similarity NPC249560
0.9226 High Similarity NPC470713
0.9226 High Similarity NPC223860
0.9226 High Similarity NPC470416

  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 NPC139060 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
0.9363 High Similarity NPD4381 Clinical (unspecified phase)
0.9202 High Similarity NPD7804 Clinical (unspecified phase)
0.9091 High Similarity NPD6797 Phase 2
0.9036 High Similarity NPD7251 Discontinued
0.8982 High Similarity NPD4338 Clinical (unspecified phase)
0.8982 High Similarity NPD7808 Phase 3
0.897 High Similarity NPD7054 Approved
0.8916 High Similarity NPD7472 Approved
0.8882 High Similarity NPD7075 Discontinued
0.8868 High Similarity NPD6801 Discontinued
0.8802 High Similarity NPD7074 Phase 3
0.879 High Similarity NPD5403 Approved
0.8788 High Similarity NPD6168 Clinical (unspecified phase)
0.8788 High Similarity NPD6167 Clinical (unspecified phase)
0.8788 High Similarity NPD6166 Phase 2
0.8742 High Similarity NPD4380 Phase 2
0.8718 High Similarity NPD6799 Approved
0.8696 High Similarity NPD7096 Clinical (unspecified phase)
0.8688 High Similarity NPD7411 Suspended
0.8683 High Similarity NPD3818 Discontinued
0.8662 High Similarity NPD5401 Approved
0.8588 High Similarity NPD6559 Discontinued
0.8528 High Similarity NPD3817 Phase 2
0.8528 High Similarity NPD5402 Approved
0.8476 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8428 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8428 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD1549 Phase 2
0.8395 Intermediate Similarity NPD6599 Discontinued
0.8362 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8343 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD1934 Approved
0.8242 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD8312 Approved
0.8171 Intermediate Similarity NPD8313 Approved
0.8153 Intermediate Similarity NPD2796 Approved
0.8148 Intermediate Similarity NPD1512 Approved
0.8144 Intermediate Similarity NPD3882 Suspended
0.8133 Intermediate Similarity NPD2801 Approved
0.8133 Intermediate Similarity NPD7819 Suspended
0.8089 Intermediate Similarity NPD1510 Phase 2
0.8077 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8059 Intermediate Similarity NPD6959 Discontinued
0.8036 Intermediate Similarity NPD7768 Phase 2
0.8035 Intermediate Similarity NPD3751 Discontinued
0.8025 Intermediate Similarity NPD1511 Approved
0.8024 Intermediate Similarity NPD8455 Phase 2
0.8 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD5844 Phase 1
0.7988 Intermediate Similarity NPD3749 Approved
0.795 Intermediate Similarity NPD3750 Approved
0.7949 Intermediate Similarity NPD1240 Approved
0.7914 Intermediate Similarity NPD7435 Discontinued
0.7907 Intermediate Similarity NPD3787 Discontinued
0.7879 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD6778 Approved
0.7849 Intermediate Similarity NPD6781 Approved
0.7849 Intermediate Similarity NPD6780 Approved
0.7849 Intermediate Similarity NPD6782 Approved
0.7849 Intermediate Similarity NPD6779 Approved
0.7849 Intermediate Similarity NPD6777 Approved
0.7849 Intermediate Similarity NPD6776 Approved
0.7848 Intermediate Similarity NPD1607 Approved
0.784 Intermediate Similarity NPD4628 Phase 3
0.7831 Intermediate Similarity NPD1653 Approved
0.7821 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD1551 Phase 2
0.7803 Intermediate Similarity NPD6232 Discontinued
0.7801 Intermediate Similarity NPD8151 Discontinued
0.7789 Intermediate Similarity NPD7584 Approved
0.7771 Intermediate Similarity NPD7473 Discontinued
0.7759 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD7199 Phase 2
0.7716 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD6798 Discontinued
0.7688 Intermediate Similarity NPD5494 Approved
0.7684 Intermediate Similarity NPD7871 Phase 2
0.7684 Intermediate Similarity NPD7870 Phase 2
0.7679 Intermediate Similarity NPD7458 Discontinued
0.7673 Intermediate Similarity NPD1933 Approved
0.7668 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7668 Intermediate Similarity NPD7874 Approved
0.7658 Intermediate Similarity NPD6233 Phase 2
0.7654 Intermediate Similarity NPD7685 Pre-registration
0.765 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD3748 Approved
0.7632 Intermediate Similarity NPD7697 Approved
0.7632 Intermediate Similarity NPD7696 Phase 3
0.7632 Intermediate Similarity NPD7698 Approved
0.7629 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7629 Intermediate Similarity NPD7783 Phase 2
0.7627 Intermediate Similarity NPD7228 Approved
0.7614 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD1465 Phase 2
0.7582 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7581 Intermediate Similarity NPD6535 Approved
0.7581 Intermediate Similarity NPD6534 Approved
0.758 Intermediate Similarity NPD6832 Phase 2
0.7565 Intermediate Similarity NPD7585 Approved
0.7565 Intermediate Similarity NPD7701 Phase 2
0.756 Intermediate Similarity NPD920 Approved
0.7531 Intermediate Similarity NPD7033 Discontinued
0.7529 Intermediate Similarity NPD919 Approved
0.7513 Intermediate Similarity NPD7583 Approved
0.75 Intermediate Similarity NPD1203 Approved
0.75 Intermediate Similarity NPD8320 Phase 1
0.75 Intermediate Similarity NPD5953 Discontinued
0.75 Intermediate Similarity NPD8319 Approved
0.7486 Intermediate Similarity NPD7286 Phase 2
0.7485 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD2935 Discontinued
0.747 Intermediate Similarity NPD6190 Approved
0.746 Intermediate Similarity NPD7700 Phase 2
0.746 Intermediate Similarity NPD7699 Phase 2
0.7455 Intermediate Similarity NPD1243 Approved
0.7455 Intermediate Similarity NPD1652 Phase 2
0.7449 Intermediate Similarity NPD7801 Approved
0.7446 Intermediate Similarity NPD8150 Discontinued
0.7442 Intermediate Similarity NPD37 Approved
0.744 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD7266 Discontinued
0.7429 Intermediate Similarity NPD6234 Discontinued
0.7425 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD4967 Phase 2
0.7414 Intermediate Similarity NPD4966 Approved
0.7414 Intermediate Similarity NPD4965 Approved
0.7396 Intermediate Similarity NPD6823 Phase 2
0.7376 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD2313 Discontinued
0.7368 Intermediate Similarity NPD3226 Approved
0.736 Intermediate Similarity NPD3926 Phase 2
0.7358 Intermediate Similarity NPD4908 Phase 1
0.7355 Intermediate Similarity NPD1091 Approved
0.7351 Intermediate Similarity NPD8434 Phase 2
0.7346 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD5124 Phase 1
0.7337 Intermediate Similarity NPD2532 Approved
0.7337 Intermediate Similarity NPD2534 Approved
0.7337 Intermediate Similarity NPD2533 Approved
0.7317 Intermediate Similarity NPD2799 Discontinued
0.7308 Intermediate Similarity NPD9717 Approved
0.7268 Intermediate Similarity NPD7240 Approved
0.7267 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD3268 Approved
0.7267 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD7097 Phase 1
0.7247 Intermediate Similarity NPD1247 Approved
0.7246 Intermediate Similarity NPD2800 Approved
0.7244 Intermediate Similarity NPD422 Phase 1
0.7244 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD230 Phase 1
0.7239 Intermediate Similarity NPD6355 Discontinued
0.7233 Intermediate Similarity NPD2798 Approved
0.7229 Intermediate Similarity NPD2344 Approved
0.7228 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD3225 Approved
0.7211 Intermediate Similarity NPD4360 Phase 2
0.7211 Intermediate Similarity NPD4363 Phase 3
0.7195 Intermediate Similarity NPD6651 Approved
0.7184 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1613 Approved
0.7176 Intermediate Similarity NPD7390 Discontinued
0.717 Intermediate Similarity NPD2797 Approved
0.716 Intermediate Similarity NPD2354 Approved
0.716 Intermediate Similarity NPD3887 Approved
0.7158 Intermediate Similarity NPD6212 Phase 3
0.7158 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD6213 Phase 3
0.7134 Intermediate Similarity NPD447 Suspended
0.7134 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD2346 Discontinued
0.7117 Intermediate Similarity NPD4062 Phase 3
0.7108 Intermediate Similarity NPD4308 Phase 3
0.7101 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1548 Phase 1
0.7097 Intermediate Similarity NPD9545 Approved
0.709 Intermediate Similarity NPD4287 Approved
0.7073 Intermediate Similarity NPD943 Approved
0.7062 Intermediate Similarity NPD4288 Approved
0.7059 Intermediate Similarity NPD2309 Approved
0.7045 Intermediate Similarity NPD6844 Discontinued
0.703 Intermediate Similarity NPD4340 Discontinued
0.702 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1019 Discontinued
0.7018 Intermediate Similarity NPD7440 Discontinued
0.7 Intermediate Similarity NPD7003 Approved
0.6994 Remote Similarity NPD5049 Phase 3
0.6989 Remote Similarity NPD5890 Approved
0.6989 Remote Similarity NPD5889 Approved
0.6977 Remote Similarity NPD7212 Phase 2
0.6977 Remote Similarity NPD7213 Phase 3
0.6968 Remote Similarity NPD9493 Approved
0.6964 Remote Similarity NPD6099 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