Structure

Physi-Chem Properties

Molecular Weight:  506.11
Volume:  462.683
LogP:  1.077
LogD:  0.451
LogS:  -4.401
# Rotatable Bonds:  6
TPSA:  216.58
# H-Bond Aceptor:  13
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.18
Synthetic Accessibility Score:  4.079
Fsp3:  0.304
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:  -6.299
MDCK Permeability:  1.5928055290714838e-05
Pgp-inhibitor:  0.033
Pgp-substrate:  0.964
Human Intestinal Absorption (HIA):  0.481
20% Bioavailability (F20%):  0.017
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.02
Plasma Protein Binding (PPB):  87.37084197998047%
Volume Distribution (VD):  0.917
Pgp-substrate:  14.679455757141113%

ADMET: Metabolism

CYP1A2-inhibitor:  0.244
CYP1A2-substrate:  0.043
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.046
CYP2C9-inhibitor:  0.222
CYP2C9-substrate:  0.331
CYP2D6-inhibitor:  0.419
CYP2D6-substrate:  0.159
CYP3A4-inhibitor:  0.165
CYP3A4-substrate:  0.014

ADMET: Excretion

Clearance (CL):  2.98
Half-life (T1/2):  0.919

ADMET: Toxicity

hERG Blockers:  0.184
Human Hepatotoxicity (H-HT):  0.185
Drug-inuced Liver Injury (DILI):  0.98
AMES Toxicity:  0.825
Rat Oral Acute Toxicity:  0.049
Maximum Recommended Daily Dose:  0.015
Skin Sensitization:  0.85
Carcinogencity:  0.054
Eye Corrosion:  0.003
Eye Irritation:  0.732
Respiratory Toxicity:  0.021

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

  Natural Product: NPC116864

Natural Product ID:  NPC116864
Common Name*:   6''-O-Acetylhyperoside
IUPAC Name:   [(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
Synonyms:   6'-O-Acetylhyperoside
Standard InCHIKey:  IGLUNMMNDNWZOA-QZGPLKIZSA-N
Standard InCHI:  InChI=1S/C23H22O13/c1-8(24)33-7-15-17(29)19(31)20(32)23(35-15)36-22-18(30)16-13(28)5-10(25)6-14(16)34-21(22)9-2-3-11(26)12(27)4-9/h2-6,15,17,19-20,23,25-29,31-32H,7H2,1H3/t15-,17+,19+,20-,23+/m1/s1
SMILES:  CC(=O)OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL559041
PubChem CID:   25230434
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
NPO7485 Nymphaea odorata Species Nymphaeaceae Eukaryota n.a. n.a. n.a. PMID[12713413]
NPO15432 Sarcodon aspratus Species Thelephoraceae Eukaryota n.a. n.a. n.a. PMID[15665489]
NPO14224 Haloxylon recurvum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. PMID[16274989]
NPO14224 Haloxylon recurvum Species Chenopodiaceae Eukaryota n.a. whole plant n.a. PMID[16651755]
NPO4485 Lamellodysidea herbacea Species Dysideidae Eukaryota n.a. Indonesian n.a. PMID[17311456]
NPO28094 Consolida oliveriana Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[19489596]
NPO14752 Sinopodophyllum emodi Species Berberidaceae Eukaryota roots and rhizomes n.a. n.a. PMID[21570846]
NPO4485 Lamellodysidea herbacea Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[28841316]
NPO3860 Allium victorialis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5517 Rhododendron tomentosum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3860 Allium victorialis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3860 Allium victorialis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO890 Remijia pedunculata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7485 Nymphaea odorata Species Nymphaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO238 Lobelia st Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8834 Cellulomonas biazotea Species Cellulomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6569 Ranunculus fluitans Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28094 Consolida oliveriana Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11880 Latua pubiflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4485 Lamellodysidea herbacea Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15240 Saracha viscosa Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14224 Haloxylon recurvum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3200 Arthrophytum leptocladum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3860 Allium victorialis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12622 Rudbeckia hirta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6239 Corbicula fluminea Species Corbiculidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13289 Frullania brittoniae Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14271 Spongia australis Species Spongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11098 Stelletta inconspicua Species Ancorinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14752 Sinopodophyllum emodi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1458 Burkholderia gladioli Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27957.1 Pinus densiflora var. densiflora Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15150 Phebalium gracile Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14035 Cladosporium tenuissimum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14661 Blepharis sindica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14156 Fragaria indica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9283 Trichia favoginea Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15432 Sarcodon aspratus Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5517 Rhododendron tomentosum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15616 Solanum toxicarum 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
NPT1597 Cell Line J774.2 IC50 = 61320.0 nM PMID[483420]
NPT1596 Organism Leishmania peruviana Leishmania peruviana IC50 = 86950.0 nM PMID[483420]
NPT1208 Organism Leishmania braziliensis Leishmania braziliensis IC50 = 51600.0 nM PMID[483420]

☑ 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 NPC116864 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 NPC244776
0.9938 High Similarity NPC153755
0.9938 High Similarity NPC190003
0.9938 High Similarity NPC175107
0.9876 High Similarity NPC4390
0.9875 High Similarity NPC20505
0.9875 High Similarity NPC155763
0.9875 High Similarity NPC235260
0.9874 High Similarity NPC317489
0.9874 High Similarity NPC127546
0.9874 High Similarity NPC52550
0.9874 High Similarity NPC223424
0.9874 High Similarity NPC173637
0.9874 High Similarity NPC84362
0.9812 High Similarity NPC120099
0.9812 High Similarity NPC219904
0.9812 High Similarity NPC225434
0.9812 High Similarity NPC203050
0.9812 High Similarity NPC223747
0.9812 High Similarity NPC138927
0.9811 High Similarity NPC56077
0.9811 High Similarity NPC277174
0.9811 High Similarity NPC88789
0.9811 High Similarity NPC113968
0.9811 High Similarity NPC73855
0.9811 High Similarity NPC145038
0.9811 High Similarity NPC253662
0.9811 High Similarity NPC118284
0.9811 High Similarity NPC135599
0.9811 High Similarity NPC276222
0.9811 High Similarity NPC274618
0.9811 High Similarity NPC308404
0.9811 High Similarity NPC179950
0.9811 High Similarity NPC281131
0.9811 High Similarity NPC328940
0.9755 High Similarity NPC472385
0.9755 High Similarity NPC471669
0.9755 High Similarity NPC89127
0.9755 High Similarity NPC198324
0.9752 High Similarity NPC206123
0.9752 High Similarity NPC95866
0.975 High Similarity NPC265530
0.975 High Similarity NPC226304
0.975 High Similarity NPC325555
0.9748 High Similarity NPC277205
0.9748 High Similarity NPC19388
0.9748 High Similarity NPC55786
0.9748 High Similarity NPC240431
0.9695 High Similarity NPC217520
0.9695 High Similarity NPC139571
0.9695 High Similarity NPC173837
0.9695 High Similarity NPC35167
0.9693 High Similarity NPC210094
0.9693 High Similarity NPC264735
0.9693 High Similarity NPC477848
0.9693 High Similarity NPC135277
0.9693 High Similarity NPC34267
0.9693 High Similarity NPC49344
0.9693 High Similarity NPC101191
0.9693 High Similarity NPC253685
0.9693 High Similarity NPC115760
0.9693 High Similarity NPC237435
0.9693 High Similarity NPC223426
0.9693 High Similarity NPC81042
0.9693 High Similarity NPC43211
0.9693 High Similarity NPC214621
0.9691 High Similarity NPC33054
0.9691 High Similarity NPC176740
0.9691 High Similarity NPC245452
0.9691 High Similarity NPC471748
0.9691 High Similarity NPC203259
0.9691 High Similarity NPC471725
0.9691 High Similarity NPC155877
0.9691 High Similarity NPC134532
0.9689 High Similarity NPC52382
0.9689 High Similarity NPC270578
0.9688 High Similarity NPC21100
0.9688 High Similarity NPC197285
0.9686 High Similarity NPC19709
0.9634 High Similarity NPC473862
0.9634 High Similarity NPC144097
0.9634 High Similarity NPC233994
0.9634 High Similarity NPC61904
0.9634 High Similarity NPC211532
0.9632 High Similarity NPC42773
0.9632 High Similarity NPC21666
0.9632 High Similarity NPC169977
0.9632 High Similarity NPC45522
0.9632 High Similarity NPC24043
0.9632 High Similarity NPC101026
0.963 High Similarity NPC156869
0.963 High Similarity NPC136042
0.963 High Similarity NPC255157
0.963 High Similarity NPC67326
0.963 High Similarity NPC259896
0.963 High Similarity NPC67105
0.963 High Similarity NPC29958
0.963 High Similarity NPC254855
0.9627 High Similarity NPC92565
0.9627 High Similarity NPC160156
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
0.9576 High Similarity NPC217387
0.9576 High Similarity NPC258044
0.9576 High Similarity NPC37668
0.9576 High Similarity NPC477895
0.9576 High Similarity NPC267680
0.9576 High Similarity NPC113836
0.9576 High Similarity NPC196127
0.9576 High Similarity NPC293626
0.9576 High Similarity NPC253521
0.9573 High Similarity NPC476472
0.9573 High Similarity NPC220173
0.9573 High Similarity NPC16194
0.9573 High Similarity NPC473327
0.9573 High Similarity NPC294629
0.9573 High Similarity NPC294815
0.9573 High Similarity NPC19108
0.9571 High Similarity NPC172807
0.9571 High Similarity NPC26230
0.9571 High Similarity NPC211594
0.9571 High Similarity NPC60735
0.9571 High Similarity NPC117260
0.9571 High Similarity NPC254540
0.9571 High Similarity NPC476405
0.9568 High Similarity NPC227508
0.9565 High Similarity NPC115674
0.9565 High Similarity NPC67037
0.9565 High Similarity NPC255615
0.9565 High Similarity NPC210073
0.9563 High Similarity NPC222936
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 NPC191306
0.9563 High Similarity NPC270335
0.956 High Similarity NPC48093
0.956 High Similarity NPC159579
0.956 High Similarity NPC224530
0.956 High Similarity NPC85707
0.956 High Similarity NPC216496
0.956 High Similarity NPC129217
0.956 High Similarity NPC259957
0.9521 High Similarity NPC470449
0.9521 High Similarity NPC36138
0.9521 High Similarity NPC162394
0.9521 High Similarity NPC470447
0.9521 High Similarity NPC241781
0.9521 High Similarity NPC470446
0.9521 High Similarity NPC156785
0.9521 High Similarity NPC470445
0.9515 High Similarity NPC202908
0.9515 High Similarity NPC292019
0.9515 High Similarity NPC296018
0.9515 High Similarity NPC14187
0.9515 High Similarity NPC472382
0.9515 High Similarity NPC122467
0.9515 High Similarity NPC65563
0.9515 High Similarity NPC154741
0.9515 High Similarity NPC268533
0.9515 High Similarity NPC472380
0.9515 High Similarity NPC472384
0.9515 High Similarity NPC470949
0.9512 High Similarity NPC472993
0.9509 High Similarity NPC285197
0.9509 High Similarity NPC245014
0.9509 High Similarity NPC84265
0.9509 High Similarity NPC282987
0.9506 High Similarity NPC48640
0.9506 High Similarity NPC275454
0.9506 High Similarity NPC149244
0.9506 High Similarity NPC229729
0.9506 High Similarity NPC116745
0.9503 High Similarity NPC34531
0.95 High Similarity NPC300537
0.95 High Similarity NPC27942
0.95 High Similarity NPC127782
0.9464 High Similarity NPC249560
0.9464 High Similarity NPC470717
0.9464 High Similarity NPC470416
0.9464 High Similarity NPC25946
0.9464 High Similarity NPC460984
0.9464 High Similarity NPC470720
0.9464 High Similarity NPC223860
0.9464 High Similarity NPC470451
0.9464 High Similarity NPC275977
0.9464 High Similarity NPC21359
0.9464 High Similarity NPC470455
0.9464 High Similarity NPC470713
0.9461 High Similarity NPC222674
0.9458 High Similarity NPC476773
0.9458 High Similarity NPC89052
0.9458 High Similarity NPC251417
0.9458 High Similarity NPC168584
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 NPC116864 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
0.9693 High Similarity NPD4338 Clinical (unspecified phase)
0.9691 High Similarity NPD6797 Phase 2
0.9632 High Similarity NPD7251 Discontinued
0.9455 High Similarity NPD7808 Phase 3
0.9448 High Similarity NPD7054 Approved
0.939 High Similarity NPD7472 Approved
0.9273 High Similarity NPD7074 Phase 3
0.9152 High Similarity NPD3818 Discontinued
0.913 High Similarity NPD4381 Clinical (unspecified phase)
0.9125 High Similarity NPD3817 Phase 2
0.9096 High Similarity NPD7804 Clinical (unspecified phase)
0.903 High Similarity NPD6167 Clinical (unspecified phase)
0.903 High Similarity NPD6166 Phase 2
0.903 High Similarity NPD6168 Clinical (unspecified phase)
0.8882 High Similarity NPD1934 Approved
0.8827 High Similarity NPD2393 Clinical (unspecified phase)
0.878 High Similarity NPD7075 Discontinued
0.8742 High Similarity NPD1512 Approved
0.872 High Similarity NPD3882 Suspended
0.872 High Similarity NPD4868 Clinical (unspecified phase)
0.8712 High Similarity NPD2801 Approved
0.8659 High Similarity NPD5402 Approved
0.865 High Similarity NPD6801 Discontinued
0.8616 High Similarity NPD1511 Approved
0.8598 High Similarity NPD7096 Clinical (unspecified phase)
0.8571 High Similarity NPD5403 Approved
0.8547 High Similarity NPD7993 Clinical (unspecified phase)
0.8528 High Similarity NPD4380 Phase 2
0.85 High Similarity NPD6799 Approved
0.8497 Intermediate Similarity NPD6559 Discontinued
0.8447 Intermediate Similarity NPD5401 Approved
0.8333 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD1653 Approved
0.8278 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD6599 Discontinued
0.8155 Intermediate Similarity NPD7819 Suspended
0.8144 Intermediate Similarity NPD7411 Suspended
0.8125 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8114 Intermediate Similarity NPD5844 Phase 1
0.8092 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD7685 Pre-registration
0.8075 Intermediate Similarity NPD1549 Phase 2
0.8057 Intermediate Similarity NPD3751 Discontinued
0.8047 Intermediate Similarity NPD1465 Phase 2
0.8035 Intermediate Similarity NPD3787 Discontinued
0.8035 Intermediate Similarity NPD6232 Discontinued
0.8023 Intermediate Similarity NPD5494 Approved
0.8012 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7473 Discontinued
0.8 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7977 Intermediate Similarity NPD7199 Phase 2
0.7965 Intermediate Similarity NPD919 Approved
0.7955 Intermediate Similarity NPD7228 Approved
0.795 Intermediate Similarity NPD2796 Approved
0.7927 Intermediate Similarity NPD6190 Approved
0.7901 Intermediate Similarity NPD7266 Discontinued
0.7901 Intermediate Similarity NPD8055 Clinical (unspecified phase)
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
0.7874 Intermediate Similarity NPD6959 Discontinued
0.7866 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD6234 Discontinued
0.7853 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7842 Intermediate Similarity NPD7435 Discontinued
0.7841 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD37 Approved
0.7772 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD3750 Approved
0.775 Intermediate Similarity NPD1613 Approved
0.775 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD4966 Approved
0.7746 Intermediate Similarity NPD4967 Phase 2
0.7746 Intermediate Similarity NPD4965 Approved
0.7725 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD1933 Approved
0.7702 Intermediate Similarity NPD230 Phase 1
0.7684 Intermediate Similarity NPD6776 Approved
0.7684 Intermediate Similarity NPD6782 Approved
0.7684 Intermediate Similarity NPD6779 Approved
0.7684 Intermediate Similarity NPD6777 Approved
0.7684 Intermediate Similarity NPD6781 Approved
0.7684 Intermediate Similarity NPD6778 Approved
0.7684 Intermediate Similarity NPD6780 Approved
0.767 Intermediate Similarity NPD1247 Approved
0.7651 Intermediate Similarity NPD4628 Phase 3
0.7644 Intermediate Similarity NPD7768 Phase 2
0.7641 Intermediate Similarity NPD8151 Discontinued
0.764 Intermediate Similarity NPD1240 Approved
0.763 Intermediate Similarity NPD8455 Phase 2
0.7629 Intermediate Similarity NPD7584 Approved
0.7625 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1551 Phase 2
0.7602 Intermediate Similarity NPD7874 Approved
0.7602 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD3749 Approved
0.7584 Intermediate Similarity NPD3926 Phase 2
0.7546 Intermediate Similarity NPD1607 Approved
0.7531 Intermediate Similarity NPD943 Approved
0.7515 Intermediate Similarity NPD2935 Discontinued
0.75 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD7240 Approved
0.7485 Intermediate Similarity NPD447 Suspended
0.7485 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7783 Phase 2
0.7474 Intermediate Similarity NPD7697 Approved
0.7474 Intermediate Similarity NPD7698 Approved
0.7474 Intermediate Similarity NPD7696 Phase 3
0.7471 Intermediate Similarity NPD2532 Approved
0.7471 Intermediate Similarity NPD2533 Approved
0.7471 Intermediate Similarity NPD2534 Approved
0.7455 Intermediate Similarity NPD3748 Approved
0.7453 Intermediate Similarity NPD3027 Phase 3
0.7444 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD8319 Approved
0.7436 Intermediate Similarity NPD7871 Phase 2
0.7436 Intermediate Similarity NPD7870 Phase 2
0.7436 Intermediate Similarity NPD8320 Phase 1
0.7421 Intermediate Similarity NPD6535 Approved
0.7421 Intermediate Similarity NPD6534 Approved
0.7411 Intermediate Similarity NPD7585 Approved
0.7411 Intermediate Similarity NPD7701 Phase 2
0.7407 Intermediate Similarity NPD6798 Discontinued
0.7384 Intermediate Similarity NPD920 Approved
0.738 Intermediate Similarity NPD8150 Discontinued
0.738 Intermediate Similarity NPD8434 Phase 2
0.7368 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD6233 Phase 2
0.736 Intermediate Similarity NPD7583 Approved
0.7349 Intermediate Similarity NPD7033 Discontinued
0.7349 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD5953 Discontinued
0.7306 Intermediate Similarity NPD7700 Phase 2
0.7306 Intermediate Similarity NPD7699 Phase 2
0.73 Intermediate Similarity NPD7801 Approved
0.7299 Intermediate Similarity NPD3226 Approved
0.7299 Intermediate Similarity NPD7458 Discontinued
0.7284 Intermediate Similarity NPD6832 Phase 2
0.7278 Intermediate Similarity NPD1652 Phase 2
0.7278 Intermediate Similarity NPD1243 Approved
0.7273 Intermediate Similarity NPD6355 Discontinued
0.7267 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD6823 Phase 2
0.7233 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD7286 Phase 2
0.7205 Intermediate Similarity NPD1203 Approved
0.7195 Intermediate Similarity NPD2313 Discontinued
0.7179 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD2800 Approved
0.717 Intermediate Similarity NPD1091 Approved
0.7169 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD5124 Phase 1
0.7166 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2346 Discontinued
0.715 Intermediate Similarity NPD4363 Phase 3
0.715 Intermediate Similarity NPD4360 Phase 2
0.7143 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2799 Discontinued
0.7135 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD7680 Approved
0.7108 Intermediate Similarity NPD4060 Phase 1
0.7102 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6100 Approved
0.7101 Intermediate Similarity NPD6099 Approved
0.7095 Intermediate Similarity NPD5353 Approved
0.7091 Intermediate Similarity NPD3268 Approved
0.7079 Intermediate Similarity NPD6844 Discontinued
0.7076 Intermediate Similarity NPD6674 Discontinued
0.7073 Intermediate Similarity NPD4908 Phase 1
0.7063 Intermediate Similarity NPD422 Phase 1
0.7055 Intermediate Similarity NPD2798 Approved
0.7049 Intermediate Similarity NPD5710 Approved
0.7049 Intermediate Similarity NPD5711 Approved
0.7048 Intermediate Similarity NPD4062 Phase 3
0.7037 Intermediate Similarity NPD3225 Approved
0.7024 Intermediate Similarity NPD7930 Approved
0.7024 Intermediate Similarity NPD6651 Approved
0.7022 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD9717 Approved
0.7019 Intermediate Similarity NPD9269 Phase 2
0.7012 Intermediate Similarity NPD9494 Approved
0.7011 Intermediate Similarity NPD5242 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
0.6995 Remote Similarity NPD8127 Discontinued
0.6994 Remote Similarity NPD3887 Approved
0.6994 Remote Similarity NPD2354 Approved
0.6994 Remote Similarity NPD2797 Approved
0.6988 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6985 Remote Similarity NPD5006 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