Structure

Physi-Chem Properties

Molecular Weight:  624.15
Volume:  590.739
LogP:  2.879
LogD:  2.158
LogS:  -4.54
# Rotatable Bonds:  9
TPSA:  225.81
# H-Bond Aceptor:  14
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.11
Synthetic Accessibility Score:  4.228
Fsp3:  0.226
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.221
MDCK Permeability:  1.854605034168344e-05
Pgp-inhibitor:  0.05
Pgp-substrate:  0.917
Human Intestinal Absorption (HIA):  0.185
20% Bioavailability (F20%):  0.064
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  98.5715560913086%
Volume Distribution (VD):  0.555
Pgp-substrate:  6.128877639770508%

ADMET: Metabolism

CYP1A2-inhibitor:  0.533
CYP1A2-substrate:  0.065
CYP2C19-inhibitor:  0.259
CYP2C19-substrate:  0.049
CYP2C9-inhibitor:  0.813
CYP2C9-substrate:  0.89
CYP2D6-inhibitor:  0.664
CYP2D6-substrate:  0.262
CYP3A4-inhibitor:  0.42
CYP3A4-substrate:  0.05

ADMET: Excretion

Clearance (CL):  5.137
Half-life (T1/2):  0.915

ADMET: Toxicity

hERG Blockers:  0.143
Human Hepatotoxicity (H-HT):  0.159
Drug-inuced Liver Injury (DILI):  0.973
AMES Toxicity:  0.767
Rat Oral Acute Toxicity:  0.061
Maximum Recommended Daily Dose:  0.054
Skin Sensitization:  0.934
Carcinogencity:  0.127
Eye Corrosion:  0.003
Eye Irritation:  0.496
Respiratory Toxicity:  0.017

Download Data

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

  Natural Product: NPC217520

Natural Product ID:  NPC217520
Common Name*:   [(2R,3S,4S,5R,6S)-6-[5,7-Dihydroxy-2-(4-Hydroxy-3-Methoxyphenyl)-4-Oxochromen-3-Yl]Oxy-3,4,5-Trihydroxyoxan-2-Yl]Methyl (E)-3-(4-Hydroxyphenyl)Prop-2-Enoate
IUPAC Name:   [(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  TVMGLJJYKIHJNJ-SETHOQODSA-N
Standard InCHI:  InChI=1S/C31H28O14/c1-41-20-10-15(5-8-18(20)34)29-30(26(38)24-19(35)11-17(33)12-21(24)43-29)45-31-28(40)27(39)25(37)22(44-31)13-42-23(36)9-4-14-2-6-16(32)7-3-14/h2-12,22,25,27-28,31-35,37,39-40H,13H2,1H3/b9-4+/t22-,25-,27+,28-,31+/m1/s1
SMILES:  COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@@H]([C@H]1O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL233903
PubChem CID:   44429737
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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
NPO22304 Morinda morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12542353]
NPO28919 Calendula officinalis Species Asteraceae Eukaryota flowers n.a. n.a. PMID[17190444]
NPO6536 Marrubium velutinum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17287127]
NPO2687 Baphia bancoensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[19007285]
NPO22304 Morinda morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[20149652]
NPO28919 Calendula officinalis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23327299]
NPO22304 Morinda morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[7775983]
NPO15308 Stigma croci n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO28919 Calendula officinalis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21263 Fructus kochiae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO21263 Fructus kochiae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO6536 Marrubium velutinum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15308 Stigma croci n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO28919 Calendula officinalis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22176 Lasiosiphon kraussianus Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9855 Oricia gabonensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5429 Vachellia pennatula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10254 Melaleuca cuticularis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6536 Marrubium velutinum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21409 Populus angustifolia Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22434 Cryptosporium pinicola n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21276 Sedum forsteri Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18291 Idea leuconoe Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2687 Baphia bancoensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28919 Calendula officinalis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22304 Morinda morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21028 Sasa paniculata Species Poaceae 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
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 21.1 % PMID[538217]

☑ 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 NPC217520 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 NPC139571
0.9879 High Similarity NPC35167
0.9879 High Similarity NPC477895
0.9878 High Similarity NPC34267
0.9878 High Similarity NPC214621
0.9878 High Similarity NPC223426
0.9878 High Similarity NPC81042
0.982 High Similarity NPC36138
0.9818 High Similarity NPC144097
0.9818 High Similarity NPC61904
0.9817 High Similarity NPC472993
0.9762 High Similarity NPC470713
0.9762 High Similarity NPC460984
0.9762 High Similarity NPC21359
0.9762 High Similarity NPC470717
0.9762 High Similarity NPC470416
0.9762 High Similarity NPC25946
0.9762 High Similarity NPC470720
0.9759 High Similarity NPC258044
0.9759 High Similarity NPC37668
0.9759 High Similarity NPC267680
0.9759 High Similarity NPC293626
0.9759 High Similarity NPC113836
0.9759 High Similarity NPC196127
0.9759 High Similarity NPC253521
0.9759 High Similarity NPC217387
0.9756 High Similarity NPC153755
0.9704 High Similarity NPC104910
0.9704 High Similarity NPC473554
0.9704 High Similarity NPC474093
0.9704 High Similarity NPC470719
0.9704 High Similarity NPC295625
0.9702 High Similarity NPC162394
0.9702 High Similarity NPC470718
0.9702 High Similarity NPC241781
0.9702 High Similarity NPC156785
0.9697 High Similarity NPC4390
0.9695 High Similarity NPC206123
0.9695 High Similarity NPC244776
0.9695 High Similarity NPC116864
0.9647 High Similarity NPC475179
0.9645 High Similarity NPC275977
0.9645 High Similarity NPC249560
0.9645 High Similarity NPC223860
0.9641 High Similarity NPC173837
0.9636 High Similarity NPC175107
0.9636 High Similarity NPC190003
0.9634 High Similarity NPC225434
0.9634 High Similarity NPC223747
0.9634 High Similarity NPC203050
0.9634 High Similarity NPC219904
0.9634 High Similarity NPC120099
0.9588 High Similarity NPC33083
0.9586 High Similarity NPC297503
0.9586 High Similarity NPC97119
0.9586 High Similarity NPC135831
0.9583 High Similarity NPC471030
0.9581 High Similarity NPC472385
0.9581 High Similarity NPC89127
0.9581 High Similarity NPC296018
0.9581 High Similarity NPC198324
0.9581 High Similarity NPC471669
0.9581 High Similarity NPC154741
0.9581 High Similarity NPC472992
0.9581 High Similarity NPC472991
0.9578 High Similarity NPC172033
0.9578 High Similarity NPC88560
0.9578 High Similarity NPC175230
0.9576 High Similarity NPC95866
0.9576 High Similarity NPC149011
0.9576 High Similarity NPC235260
0.9576 High Similarity NPC20505
0.9576 High Similarity NPC155763
0.9576 High Similarity NPC204937
0.9573 High Similarity NPC127546
0.9573 High Similarity NPC317489
0.9573 High Similarity NPC173637
0.9573 High Similarity NPC325555
0.9573 High Similarity NPC223424
0.9573 High Similarity NPC265530
0.9573 High Similarity NPC84362
0.9573 High Similarity NPC52550
0.9573 High Similarity NPC226304
0.9532 High Similarity NPC30011
0.9532 High Similarity NPC72554
0.9532 High Similarity NPC97817
0.9524 High Similarity NPC476773
0.9521 High Similarity NPC49344
0.9521 High Similarity NPC210094
0.9521 High Similarity NPC476472
0.9521 High Similarity NPC101191
0.9521 High Similarity NPC294815
0.9521 High Similarity NPC264735
0.9521 High Similarity NPC19108
0.9521 High Similarity NPC477848
0.9521 High Similarity NPC253685
0.9521 High Similarity NPC220173
0.9521 High Similarity NPC115760
0.9521 High Similarity NPC237435
0.9521 High Similarity NPC43211
0.9521 High Similarity NPC135277
0.9521 High Similarity NPC473327
0.9521 High Similarity NPC16194
0.9518 High Similarity NPC47140
0.9518 High Similarity NPC155877
0.9518 High Similarity NPC60735
0.9518 High Similarity NPC134532
0.9518 High Similarity NPC33054
0.9518 High Similarity NPC203259
0.9518 High Similarity NPC471748
0.9518 High Similarity NPC67134
0.9518 High Similarity NPC176740
0.9518 High Similarity NPC26230
0.9518 High Similarity NPC471725
0.9515 High Similarity NPC138927
0.9512 High Similarity NPC328940
0.9512 High Similarity NPC21100
0.9512 High Similarity NPC113968
0.9512 High Similarity NPC274618
0.9512 High Similarity NPC277174
0.9512 High Similarity NPC145038
0.9512 High Similarity NPC73855
0.9512 High Similarity NPC135599
0.9512 High Similarity NPC197285
0.9512 High Similarity NPC118284
0.9512 High Similarity NPC179950
0.9512 High Similarity NPC88789
0.9512 High Similarity NPC56077
0.9512 High Similarity NPC281131
0.9512 High Similarity NPC276222
0.9512 High Similarity NPC253662
0.9512 High Similarity NPC308404
0.9471 High Similarity NPC470445
0.9471 High Similarity NPC35924
0.9471 High Similarity NPC470446
0.9471 High Similarity NPC199172
0.9471 High Similarity NPC470449
0.9471 High Similarity NPC470447
0.9464 High Similarity NPC473862
0.9464 High Similarity NPC233994
0.9464 High Similarity NPC211532
0.9461 High Similarity NPC24043
0.9461 High Similarity NPC169977
0.9461 High Similarity NPC101026
0.9461 High Similarity NPC21666
0.9461 High Similarity NPC42773
0.9461 High Similarity NPC45522
0.9458 High Similarity NPC259896
0.9458 High Similarity NPC254855
0.9458 High Similarity NPC29958
0.9458 High Similarity NPC136042
0.9458 High Similarity NPC51326
0.9458 High Similarity NPC231194
0.9458 High Similarity NPC67326
0.9458 High Similarity NPC255157
0.9458 High Similarity NPC67105
0.9458 High Similarity NPC285197
0.9458 High Similarity NPC156869
0.9455 High Similarity NPC229729
0.9455 High Similarity NPC116745
0.9451 High Similarity NPC55786
0.9451 High Similarity NPC19240
0.9451 High Similarity NPC129264
0.9451 High Similarity NPC240431
0.9451 High Similarity NPC85751
0.9451 High Similarity NPC311830
0.9451 High Similarity NPC277205
0.9451 High Similarity NPC139060
0.9451 High Similarity NPC22832
0.9451 High Similarity NPC19388
0.9451 High Similarity NPC205824
0.9415 High Similarity NPC470455
0.9415 High Similarity NPC470451
0.9408 High Similarity NPC476619
0.9408 High Similarity NPC476622
0.9408 High Similarity NPC89052
0.9408 High Similarity NPC476621
0.9408 High Similarity NPC476620
0.9408 High Similarity NPC476623
0.9408 High Similarity NPC251417
0.9408 High Similarity NPC476618
0.9408 High Similarity NPC472387
0.9405 High Similarity NPC294629
0.9401 High Similarity NPC476405
0.9401 High Similarity NPC254540
0.9401 High Similarity NPC117260
0.9401 High Similarity NPC211594
0.9401 High Similarity NPC172807
0.9401 High Similarity NPC245452
0.9398 High Similarity NPC195257
0.9398 High Similarity NPC52382
0.9398 High Similarity NPC209296
0.9398 High Similarity NPC270578
0.9398 High Similarity NPC227508
0.9394 High Similarity NPC210073
0.9394 High Similarity NPC115674
0.939 High Similarity NPC222936
0.939 High Similarity NPC309025
0.939 High Similarity NPC19709
0.939 High Similarity NPC270335

  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 NPC217520 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
0.9521 High Similarity NPD4338 Clinical (unspecified phase)
0.9518 High Similarity NPD6797 Phase 2
0.9461 High Similarity NPD7251 Discontinued
0.9405 High Similarity NPD7808 Phase 3
0.9398 High Similarity NPD7054 Approved
0.9341 High Similarity NPD7472 Approved
0.9226 High Similarity NPD7074 Phase 3
0.9217 High Similarity NPD6168 Clinical (unspecified phase)
0.9217 High Similarity NPD6167 Clinical (unspecified phase)
0.9217 High Similarity NPD6166 Phase 2
0.9107 High Similarity NPD3818 Discontinued
0.897 High Similarity NPD4381 Clinical (unspecified phase)
0.8963 High Similarity NPD3817 Phase 2
0.8941 High Similarity NPD7804 Clinical (unspecified phase)
0.8795 High Similarity NPD4868 Clinical (unspecified phase)
0.8728 High Similarity NPD7993 Clinical (unspecified phase)
0.8727 High Similarity NPD1934 Approved
0.8683 High Similarity NPD3882 Suspended
0.8631 High Similarity NPD7075 Discontinued
0.8563 High Similarity NPD2801 Approved
0.8563 High Similarity NPD2393 Clinical (unspecified phase)
0.8512 High Similarity NPD5402 Approved
0.8503 High Similarity NPD6801 Discontinued
0.8476 Intermediate Similarity NPD1512 Approved
0.8466 Intermediate Similarity NPD6559 Discontinued
0.8452 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8424 Intermediate Similarity NPD5403 Approved
0.8383 Intermediate Similarity NPD4380 Phase 2
0.8354 Intermediate Similarity NPD6799 Approved
0.8354 Intermediate Similarity NPD1511 Approved
0.8352 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD5401 Approved
0.8295 Intermediate Similarity NPD5844 Phase 1
0.8263 Intermediate Similarity NPD1653 Approved
0.8225 Intermediate Similarity NPD7411 Suspended
0.8204 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8136 Intermediate Similarity NPD3751 Discontinued
0.8114 Intermediate Similarity NPD6232 Discontinued
0.8084 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD7473 Discontinued
0.8066 Intermediate Similarity NPD8312 Approved
0.8066 Intermediate Similarity NPD8313 Approved
0.8059 Intermediate Similarity NPD6599 Discontinued
0.8057 Intermediate Similarity NPD7199 Phase 2
0.8056 Intermediate Similarity NPD7685 Pre-registration
0.8043 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8034 Intermediate Similarity NPD7228 Approved
0.8023 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD7819 Suspended
0.8023 Intermediate Similarity NPD1465 Phase 2
0.8011 Intermediate Similarity NPD3787 Discontinued
0.8 Intermediate Similarity NPD5494 Approved
0.7978 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7977 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD6959 Discontinued
0.7943 Intermediate Similarity NPD919 Approved
0.7939 Intermediate Similarity NPD1549 Phase 2
0.7917 Intermediate Similarity NPD7435 Discontinued
0.7904 Intermediate Similarity NPD6190 Approved
0.7879 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD6234 Discontinued
0.7818 Intermediate Similarity NPD2796 Approved
0.7811 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD8151 Discontinued
0.7789 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD7266 Discontinued
0.776 Intermediate Similarity NPD6780 Approved
0.776 Intermediate Similarity NPD6777 Approved
0.776 Intermediate Similarity NPD6779 Approved
0.776 Intermediate Similarity NPD6781 Approved
0.776 Intermediate Similarity NPD6776 Approved
0.776 Intermediate Similarity NPD6778 Approved
0.776 Intermediate Similarity NPD6782 Approved
0.7759 Intermediate Similarity NPD37 Approved
0.7758 Intermediate Similarity NPD1510 Phase 2
0.7738 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD4965 Approved
0.7727 Intermediate Similarity NPD4966 Approved
0.7727 Intermediate Similarity NPD4967 Phase 2
0.7727 Intermediate Similarity NPD7768 Phase 2
0.7714 Intermediate Similarity NPD8455 Phase 2
0.7684 Intermediate Similarity NPD3749 Approved
0.7683 Intermediate Similarity NPD1933 Approved
0.7677 Intermediate Similarity NPD7874 Approved
0.7677 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD3926 Phase 2
0.7654 Intermediate Similarity NPD1247 Approved
0.7633 Intermediate Similarity NPD3750 Approved
0.7619 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7870 Phase 2
0.7602 Intermediate Similarity NPD7871 Phase 2
0.7576 Intermediate Similarity NPD230 Phase 1
0.7574 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD7240 Approved
0.7551 Intermediate Similarity NPD7696 Phase 3
0.7551 Intermediate Similarity NPD7698 Approved
0.7551 Intermediate Similarity NPD7697 Approved
0.755 Intermediate Similarity NPD7783 Phase 2
0.755 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD4628 Phase 3
0.7525 Intermediate Similarity NPD7584 Approved
0.7515 Intermediate Similarity NPD1240 Approved
0.7515 Intermediate Similarity NPD1613 Approved
0.7515 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD8320 Phase 1
0.7513 Intermediate Similarity NPD8319 Approved
0.75 Intermediate Similarity NPD1551 Phase 2
0.75 Intermediate Similarity NPD6535 Approved
0.75 Intermediate Similarity NPD6534 Approved
0.7487 Intermediate Similarity NPD7701 Phase 2
0.747 Intermediate Similarity NPD447 Suspended
0.746 Intermediate Similarity NPD8150 Discontinued
0.7425 Intermediate Similarity NPD1607 Approved
0.741 Intermediate Similarity NPD943 Approved
0.7396 Intermediate Similarity NPD2935 Discontinued
0.7394 Intermediate Similarity NPD6798 Discontinued
0.7394 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7458 Discontinued
0.7385 Intermediate Similarity NPD7699 Phase 2
0.7385 Intermediate Similarity NPD7700 Phase 2
0.7376 Intermediate Similarity NPD7801 Approved
0.7356 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD6233 Phase 2
0.7337 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD3748 Approved
0.7333 Intermediate Similarity NPD3027 Phase 3
0.7323 Intermediate Similarity NPD6823 Phase 2
0.7313 Intermediate Similarity NPD7585 Approved
0.7288 Intermediate Similarity NPD3226 Approved
0.7286 Intermediate Similarity NPD7680 Approved
0.7277 Intermediate Similarity NPD8434 Phase 2
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD920 Approved
0.7264 Intermediate Similarity NPD7583 Approved
0.7259 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD2533 Approved
0.7257 Intermediate Similarity NPD2532 Approved
0.7257 Intermediate Similarity NPD2534 Approved
0.7238 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD5953 Discontinued
0.7212 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD6832 Phase 2
0.7168 Intermediate Similarity NPD1243 Approved
0.7159 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7549 Discontinued
0.7143 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7033 Discontinued
0.7128 Intermediate Similarity NPD7286 Phase 2
0.7105 Intermediate Similarity NPD7039 Approved
0.7105 Intermediate Similarity NPD7038 Approved
0.7102 Intermediate Similarity NPD7390 Discontinued
0.7092 Intermediate Similarity NPD6212 Phase 3
0.7092 Intermediate Similarity NPD6213 Phase 3
0.7092 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD1203 Approved
0.7088 Intermediate Similarity NPD5353 Approved
0.7083 Intermediate Similarity NPD2313 Discontinued
0.7081 Intermediate Similarity NPD8127 Discontinued
0.7069 Intermediate Similarity NPD6674 Discontinued
0.7069 Intermediate Similarity NPD1652 Phase 2
0.7066 Intermediate Similarity NPD4908 Phase 1
0.7059 Intermediate Similarity NPD6355 Discontinued
0.7059 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD2346 Discontinued
0.7035 Intermediate Similarity NPD2799 Discontinued
0.7029 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD9494 Approved
0.7005 Intermediate Similarity NPD5242 Approved
0.6982 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6979 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6978 Remote Similarity NPD6844 Discontinued
0.6971 Remote Similarity NPD2800 Approved
0.697 Remote Similarity NPD4379 Clinical (unspecified phase)
0.697 Remote Similarity NPD4363 Phase 3
0.697 Remote Similarity NPD4360 Phase 2
0.6961 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5124 Phase 1
0.6959 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2344 Approved
0.6951 Remote Similarity NPD1091 Approved
0.6946 Remote Similarity NPD2798 Approved
0.6923 Remote Similarity NPD6386 Approved
0.6923 Remote Similarity NPD6385 Approved
0.6909 Remote Similarity NPD9269 Phase 2
0.6909 Remote Similarity NPD9717 Approved
0.6907 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6901 Remote Similarity NPD4060 Phase 1
0.6897 Remote Similarity NPD5006 Approved
0.6897 Remote Similarity NPD6099 Approved
0.6897 Remote Similarity NPD6100 Approved
0.6897 Remote Similarity NPD5005 Approved
0.6895 Remote Similarity NPD2163 Approved
0.6893 Remote Similarity NPD2354 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