Structure

Physi-Chem Properties

Molecular Weight:  272.1
Volume:  278.965
LogP:  3.343
LogD:  3.362
LogS:  -3.257
# Rotatable Bonds:  2
TPSA:  58.92
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.882
Synthetic Accessibility Score:  2.754
Fsp3:  0.25
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.797
MDCK Permeability:  1.55546822497854e-05
Pgp-inhibitor:  0.009
Pgp-substrate:  0.984
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.984
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.057
Plasma Protein Binding (PPB):  97.32714080810547%
Volume Distribution (VD):  0.883
Pgp-substrate:  3.258021831512451%

ADMET: Metabolism

CYP1A2-inhibitor:  0.973
CYP1A2-substrate:  0.956
CYP2C19-inhibitor:  0.925
CYP2C19-substrate:  0.382
CYP2C9-inhibitor:  0.766
CYP2C9-substrate:  0.963
CYP2D6-inhibitor:  0.91
CYP2D6-substrate:  0.941
CYP3A4-inhibitor:  0.628
CYP3A4-substrate:  0.525

ADMET: Excretion

Clearance (CL):  14.911
Half-life (T1/2):  0.677

ADMET: Toxicity

hERG Blockers:  0.084
Human Hepatotoxicity (H-HT):  0.237
Drug-inuced Liver Injury (DILI):  0.18
AMES Toxicity:  0.359
Rat Oral Acute Toxicity:  0.193
Maximum Recommended Daily Dose:  0.939
Skin Sensitization:  0.928
Carcinogencity:  0.856
Eye Corrosion:  0.004
Eye Irritation:  0.923
Respiratory Toxicity:  0.683

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

  Natural Product: NPC230479

Natural Product ID:  NPC230479
Common Name*:   (3S)-Vestitol
IUPAC Name:   (3S)-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
Synonyms:   (3S)-Vestitol
Standard InCHIKey:  XRVFNNUXNVWYTI-LLVKDONJSA-N
Standard InCHI:  InChI=1S/C16H16O4/c1-19-13-4-5-14(15(18)8-13)11-6-10-2-3-12(17)7-16(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3/t11-/m1/s1
SMILES:  COc1ccc(c(c1)O)[C@H]1COc2c(C1)ccc(c2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL252913
PubChem CID:   177149
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002586] O-methylated isoflavonoids
          • [CHEMONTID:0002606] 4'-O-methylated isoflavonoids

*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
NPO15003 Streptomyces lydicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. DOI[10.1021/ja107190w]
NPO33288 Brazilian Red Propolis Strain n.a. n.a. n.a. Brazilian n.a. PMID[17950610]
NPO33288 Brazilian Red Propolis Strain n.a. n.a. n.a. Brazilian n.a. PMID[18440233]
NPO16422 Teclea gerrardii Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO33288 Brazilian Red Propolis Strain n.a. n.a. n.a. n.a. n.a. PMID[26938776]
NPO33288 Brazilian Red Propolis Strain n.a. n.a. n.a. n.a. n.a. PMID[32525315]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. PMID[6705789]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Hay n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Hull Husk n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2611 Dalbergia variabilis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8300 Apis mellifera ligustica Species Apidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17351 Tropicoporus linteus Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2611 Dalbergia variabilis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2611 Dalbergia variabilis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2611 Dalbergia variabilis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16422 Teclea gerrardii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9125 Haemanthus amarylloides Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14851 Lantana montevidensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4216 Dalbergia assamica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15502 Muscari botryoides Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7988.1 Fraxinus angustifolia subsp. oxycarpa Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8435 Hedysarum theinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15260 Senecio suaveolens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15384 Olearia pimeleoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2318 Stellaria holostea Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17351 Tropicoporus linteus Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13700 Streptomyces nobilis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15003 Streptomyces lydicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14543 Mycena sanguinolenta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13210 Echinops transiliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22207 Polyporus pini Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15639 Dasycladus vermicularis Species Dasycladaceae 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
NPT461 Cell Line PANC-1 Homo sapiens CD100 > 100.0 uM PMID[549449]
NPT81 Cell Line A549 Homo sapiens IC50 > 100000.0 nM PMID[549450]
NPT165 Cell Line HeLa Homo sapiens IC50 = 72600.0 nM PMID[549450]
NPT453 Cell Line HT-1080 Homo sapiens IC50 > 100000.0 nM PMID[549450]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 67000.0 nM PMID[549450]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 57400.0 nM PMID[549450]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 92300.0 nM PMID[549450]
NPT2 Others Unspecified Activity = 0.546 % PMID[549451]
NPT2 Others Unspecified Activity = 2.72 % PMID[549451]
NPT2 Others Unspecified Activity = 2.93 % PMID[549451]
NPT2 Others Unspecified Activity = 93.8 % PMID[549451]
NPT2 Others Unspecified Activity = 1.03 % PMID[549451]
NPT2 Others Unspecified Activity = 3.35 % PMID[549451]
NPT2 Others Unspecified Activity = 6.62 % PMID[549451]
NPT2 Others Unspecified Activity = 89.0 % PMID[549451]

☑ 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 NPC230479 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 NPC283049
1.0 High Similarity NPC26879
1.0 High Similarity NPC50315
0.9835 High Similarity NPC53986
0.9835 High Similarity NPC38664
0.9754 High Similarity NPC93962
0.9672 High Similarity NPC39064
0.9672 High Similarity NPC47283
0.9597 High Similarity NPC118683
0.9597 High Similarity NPC12875
0.9597 High Similarity NPC207892
0.9597 High Similarity NPC17343
0.9597 High Similarity NPC244888
0.9597 High Similarity NPC150011
0.9597 High Similarity NPC164804
0.9597 High Similarity NPC236014
0.9597 High Similarity NPC129106
0.9597 High Similarity NPC293203
0.9597 High Similarity NPC268917
0.9597 High Similarity NPC129784
0.9597 High Similarity NPC211413
0.9597 High Similarity NPC280653
0.9597 High Similarity NPC164574
0.9597 High Similarity NPC118114
0.9597 High Similarity NPC68205
0.9597 High Similarity NPC196765
0.9597 High Similarity NPC228369
0.9597 High Similarity NPC206224
0.9597 High Similarity NPC476166
0.9597 High Similarity NPC300875
0.9583 High Similarity NPC76465
0.9583 High Similarity NPC38761
0.958 High Similarity NPC193364
0.958 High Similarity NPC54972
0.952 High Similarity NPC13005
0.9516 High Similarity NPC27187
0.9516 High Similarity NPC470225
0.9512 High Similarity NPC274717
0.9508 High Similarity NPC262573
0.9508 High Similarity NPC471215
0.95 High Similarity NPC100099
0.95 High Similarity NPC36016
0.9444 High Similarity NPC77196
0.944 High Similarity NPC162801
0.944 High Similarity NPC181497
0.944 High Similarity NPC271945
0.9426 High Similarity NPC102540
0.9426 High Similarity NPC17809
0.9426 High Similarity NPC188022
0.9426 High Similarity NPC103420
0.9426 High Similarity NPC285040
0.937 High Similarity NPC223008
0.937 High Similarity NPC296915
0.937 High Similarity NPC225696
0.937 High Similarity NPC198154
0.937 High Similarity NPC97834
0.937 High Similarity NPC115335
0.9355 High Similarity NPC87224
0.9355 High Similarity NPC222572
0.935 High Similarity NPC276212
0.9344 High Similarity NPC86502
0.9344 High Similarity NPC197351
0.9344 High Similarity NPC246648
0.9344 High Similarity NPC294156
0.9344 High Similarity NPC134195
0.9344 High Similarity NPC106914
0.9344 High Similarity NPC256015
0.9291 High Similarity NPC92805
0.9291 High Similarity NPC85435
0.9286 High Similarity NPC103799
0.928 High Similarity NPC134360
0.925 High Similarity NPC93398
0.925 High Similarity NPC258979
0.925 High Similarity NPC8283
0.9225 High Similarity NPC270456
0.9225 High Similarity NPC173660
0.9225 High Similarity NPC162659
0.9225 High Similarity NPC265433
0.9225 High Similarity NPC248727
0.9219 High Similarity NPC476616
0.9219 High Similarity NPC476617
0.9219 High Similarity NPC476615
0.9219 High Similarity NPC117048
0.9219 High Similarity NPC473107
0.9219 High Similarity NPC124085
0.9167 High Similarity NPC59561
0.9167 High Similarity NPC172253
0.9167 High Similarity NPC295259
0.9154 High Similarity NPC474687
0.9147 High Similarity NPC195022
0.9141 High Similarity NPC11060
0.9134 High Similarity NPC472590
0.912 High Similarity NPC149796
0.9113 High Similarity NPC207179
0.9113 High Similarity NPC278552
0.9113 High Similarity NPC167571
0.9106 High Similarity NPC474160
0.9098 High Similarity NPC190454
0.9098 High Similarity NPC97432
0.9084 High Similarity NPC127218
0.9084 High Similarity NPC70682
0.9084 High Similarity NPC245207
0.9084 High Similarity NPC475836
0.9084 High Similarity NPC260741
0.9084 High Similarity NPC471388
0.9084 High Similarity NPC319647
0.9084 High Similarity NPC25966
0.9083 High Similarity NPC74821
0.9077 High Similarity NPC262585
0.9077 High Similarity NPC471522
0.9077 High Similarity NPC3049
0.9077 High Similarity NPC234952
0.9077 High Similarity NPC18189
0.9077 High Similarity NPC20829
0.9076 High Similarity NPC85292
0.9076 High Similarity NPC229147
0.9076 High Similarity NPC54507
0.907 High Similarity NPC317380
0.9015 High Similarity NPC184797
0.9015 High Similarity NPC27495
0.9015 High Similarity NPC309124
0.9008 High Similarity NPC470307
0.9008 High Similarity NPC470308
0.9008 High Similarity NPC276490
0.9 High Similarity NPC151224
0.9 High Similarity NPC470356
0.9 High Similarity NPC473413
0.9 High Similarity NPC474206
0.9 High Similarity NPC112246
0.9 High Similarity NPC61946
0.9 High Similarity NPC121812
0.9 High Similarity NPC112939
0.9 High Similarity NPC94750
0.8992 High Similarity NPC215037
0.8992 High Similarity NPC469610
0.8992 High Similarity NPC185541
0.8992 High Similarity NPC464
0.8984 High Similarity NPC8899
0.8976 High Similarity NPC472797
0.8968 High Similarity NPC46978
0.896 High Similarity NPC81641
0.896 High Similarity NPC113495
0.8947 High Similarity NPC35216
0.8947 High Similarity NPC471389
0.8947 High Similarity NPC5155
0.8943 High Similarity NPC476633
0.8939 High Similarity NPC236306
0.8939 High Similarity NPC473739
0.8939 High Similarity NPC232164
0.8939 High Similarity NPC32630
0.8931 High Similarity NPC227503
0.8931 High Similarity NPC306441
0.8931 High Similarity NPC16435
0.8931 High Similarity NPC474639
0.8931 High Similarity NPC230734
0.8931 High Similarity NPC141717
0.8926 High Similarity NPC131118
0.8915 High Similarity NPC86655
0.8915 High Similarity NPC202762
0.8915 High Similarity NPC472798
0.8915 High Similarity NPC469611
0.8915 High Similarity NPC127624
0.8898 High Similarity NPC38604
0.8898 High Similarity NPC211179
0.8881 High Similarity NPC59841
0.8881 High Similarity NPC107161
0.8881 High Similarity NPC475891
0.8881 High Similarity NPC2613
0.8881 High Similarity NPC204347
0.888 High Similarity NPC270030
0.888 High Similarity NPC159132
0.8872 High Similarity NPC259519
0.8871 High Similarity NPC77789
0.8871 High Similarity NPC150026
0.8871 High Similarity NPC18128
0.8864 High Similarity NPC474282
0.8864 High Similarity NPC103976
0.8864 High Similarity NPC107551
0.8864 High Similarity NPC211549
0.8864 High Similarity NPC102904
0.8864 High Similarity NPC176051
0.8864 High Similarity NPC326797
0.8862 High Similarity NPC102639
0.8855 High Similarity NPC234333
0.8855 High Similarity NPC260898
0.8855 High Similarity NPC15109
0.8855 High Similarity NPC125579
0.8855 High Similarity NPC11727
0.8855 High Similarity NPC47398
0.8855 High Similarity NPC164787
0.8846 High Similarity NPC263064
0.8846 High Similarity NPC168059
0.8846 High Similarity NPC229442
0.8843 High Similarity NPC33270
0.8843 High Similarity NPC474933
0.8843 High Similarity NPC69261
0.8837 High Similarity NPC160623
0.8828 High Similarity NPC472795
0.8828 High Similarity NPC472796
0.8828 High Similarity NPC471518

  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 NPC230479 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
0.9672 High Similarity NPD4908 Phase 1
0.958 High Similarity NPD1610 Phase 2
0.9516 High Similarity NPD4907 Clinical (unspecified phase)
0.9083 High Similarity NPD1548 Phase 1
0.8819 High Similarity NPD2861 Phase 2
0.88 High Similarity NPD4749 Approved
0.8769 High Similarity NPD1612 Clinical (unspecified phase)
0.8769 High Similarity NPD1613 Approved
0.875 High Similarity NPD1529 Clinical (unspecified phase)
0.8682 High Similarity NPD4625 Phase 3
0.8672 High Similarity NPD1530 Clinical (unspecified phase)
0.8615 High Similarity NPD6410 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD3027 Phase 3
0.8333 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8227 Intermediate Similarity NPD7447 Phase 1
0.8203 Intermediate Similarity NPD422 Phase 1
0.8156 Intermediate Similarity NPD7213 Phase 3
0.8156 Intermediate Similarity NPD7212 Phase 2
0.8148 Intermediate Similarity NPD5124 Phase 1
0.8148 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.8116 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8116 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8099 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.808 Intermediate Similarity NPD6671 Approved
0.8058 Intermediate Similarity NPD1549 Phase 2
0.8043 Intermediate Similarity NPD6099 Approved
0.8043 Intermediate Similarity NPD6100 Approved
0.803 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD3750 Approved
0.7943 Intermediate Similarity NPD7466 Approved
0.7941 Intermediate Similarity NPD4060 Phase 1
0.7939 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7934 Intermediate Similarity NPD968 Approved
0.7923 Intermediate Similarity NPD1091 Approved
0.7905 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7899 Intermediate Similarity NPD940 Approved
0.7899 Intermediate Similarity NPD846 Approved
0.7891 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD8651 Approved
0.7842 Intermediate Similarity NPD1510 Phase 2
0.7838 Intermediate Similarity NPD1934 Approved
0.782 Intermediate Similarity NPD2797 Approved
0.7817 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD3892 Phase 2
0.7805 Intermediate Similarity NPD2684 Approved
0.7803 Intermediate Similarity NPD6582 Phase 2
0.7803 Intermediate Similarity NPD6583 Phase 3
0.7795 Intermediate Similarity NPD7157 Approved
0.7786 Intermediate Similarity NPD2796 Approved
0.777 Intermediate Similarity NPD4536 Approved
0.777 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD4538 Approved
0.7761 Intermediate Similarity NPD6584 Phase 3
0.7746 Intermediate Similarity NPD1652 Phase 2
0.7742 Intermediate Similarity NPD4750 Phase 3
0.7731 Intermediate Similarity NPD3020 Approved
0.7704 Intermediate Similarity NPD3018 Phase 2
0.7703 Intermediate Similarity NPD4380 Phase 2
0.7698 Intermediate Similarity NPD7843 Approved
0.7698 Intermediate Similarity NPD5535 Approved
0.7682 Intermediate Similarity NPD7768 Phase 2
0.7681 Intermediate Similarity NPD1240 Approved
0.7667 Intermediate Similarity NPD7819 Suspended
0.7664 Intermediate Similarity NPD3268 Approved
0.7651 Intermediate Similarity NPD7411 Suspended
0.7643 Intermediate Similarity NPD2200 Suspended
0.7638 Intermediate Similarity NPD5283 Phase 1
0.7632 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD7075 Discontinued
0.7626 Intermediate Similarity NPD6355 Discontinued
0.7603 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD5588 Approved
0.7589 Intermediate Similarity NPD7033 Discontinued
0.7589 Intermediate Similarity NPD5960 Phase 3
0.7589 Intermediate Similarity NPD3748 Approved
0.7581 Intermediate Similarity NPD290 Approved
0.7571 Intermediate Similarity NPD1607 Approved
0.7566 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD2238 Phase 2
0.755 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD2801 Approved
0.7537 Intermediate Similarity NPD2982 Phase 2
0.7537 Intermediate Similarity NPD2983 Phase 2
0.7536 Intermediate Similarity NPD6798 Discontinued
0.7535 Intermediate Similarity NPD1551 Phase 2
0.7534 Intermediate Similarity NPD1511 Approved
0.7521 Intermediate Similarity NPD1242 Phase 1
0.75 Intermediate Similarity NPD5846 Approved
0.75 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6516 Phase 2
0.7484 Intermediate Similarity NPD6959 Discontinued
0.7481 Intermediate Similarity NPD3225 Approved
0.7481 Intermediate Similarity NPD6696 Suspended
0.7479 Intermediate Similarity NPD2860 Approved
0.7479 Intermediate Similarity NPD2859 Approved
0.7466 Intermediate Similarity NPD6666 Approved
0.7466 Intermediate Similarity NPD5058 Phase 3
0.7466 Intermediate Similarity NPD6667 Approved
0.7463 Intermediate Similarity NPD2981 Phase 2
0.7463 Intermediate Similarity NPD1608 Approved
0.746 Intermediate Similarity NPD5451 Approved
0.7452 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD6166 Phase 2
0.7452 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD1653 Approved
0.7444 Intermediate Similarity NPD3496 Discontinued
0.7436 Intermediate Similarity NPD7229 Phase 3
0.7432 Intermediate Similarity NPD1512 Approved
0.7431 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD3443 Approved
0.7424 Intermediate Similarity NPD3444 Approved
0.7424 Intermediate Similarity NPD3445 Approved
0.7422 Intermediate Similarity NPD821 Approved
0.7415 Intermediate Similarity NPD6799 Approved
0.7407 Intermediate Similarity NPD5327 Phase 3
0.7395 Intermediate Similarity NPD2933 Approved
0.7395 Intermediate Similarity NPD2934 Approved
0.7394 Intermediate Similarity NPD7097 Phase 1
0.7385 Intermediate Similarity NPD2557 Approved
0.7379 Intermediate Similarity NPD6674 Discontinued
0.7376 Intermediate Similarity NPD5735 Approved
0.7372 Intermediate Similarity NPD3690 Phase 2
0.7372 Intermediate Similarity NPD3691 Phase 2
0.7372 Intermediate Similarity NPD7199 Phase 2
0.7368 Intermediate Similarity NPD2667 Approved
0.7368 Intermediate Similarity NPD37 Approved
0.7368 Intermediate Similarity NPD2668 Approved
0.7361 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD6002 Phase 3
0.7361 Intermediate Similarity NPD6005 Phase 3
0.7361 Intermediate Similarity NPD6004 Phase 3
0.7357 Intermediate Similarity NPD6233 Phase 2
0.7355 Intermediate Similarity NPD6234 Discontinued
0.7351 Intermediate Similarity NPD6599 Discontinued
0.7348 Intermediate Similarity NPD6581 Approved
0.7348 Intermediate Similarity NPD6580 Approved
0.7338 Intermediate Similarity NPD4966 Approved
0.7338 Intermediate Similarity NPD7095 Approved
0.7338 Intermediate Similarity NPD4965 Approved
0.7338 Intermediate Similarity NPD3882 Suspended
0.7338 Intermediate Similarity NPD4967 Phase 2
0.7333 Intermediate Similarity NPD2232 Approved
0.7333 Intermediate Similarity NPD2235 Phase 2
0.7333 Intermediate Similarity NPD2233 Approved
0.7333 Intermediate Similarity NPD2231 Phase 2
0.7333 Intermediate Similarity NPD2230 Approved
0.7329 Intermediate Similarity NPD4628 Phase 3
0.7328 Intermediate Similarity NPD3596 Phase 2
0.7328 Intermediate Similarity NPD7340 Approved
0.7324 Intermediate Similarity NPD4097 Suspended
0.7323 Intermediate Similarity NPD3021 Approved
0.7323 Intermediate Similarity NPD3022 Approved
0.7312 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD5844 Phase 1
0.731 Intermediate Similarity NPD2424 Discontinued
0.7308 Intermediate Similarity NPD5494 Approved
0.7305 Intermediate Similarity NPD4140 Approved
0.7305 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD6072 Discontinued
0.7299 Intermediate Similarity NPD4098 Discontinued
0.7299 Intermediate Similarity NPD3266 Approved
0.7299 Intermediate Similarity NPD3267 Approved
0.7297 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7041 Phase 2
0.7293 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD5585 Approved
0.7292 Intermediate Similarity NPD2935 Discontinued
0.729 Intermediate Similarity NPD3749 Approved
0.7285 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD3685 Discontinued
0.7278 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3817 Phase 2
0.7267 Intermediate Similarity NPD7074 Phase 3
0.7266 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD2800 Approved
0.7259 Intermediate Similarity NPD1535 Discovery
0.7255 Intermediate Similarity NPD6801 Discontinued
0.7254 Intermediate Similarity NPD4340 Discontinued
0.7241 Intermediate Similarity NPD5763 Approved
0.7241 Intermediate Similarity NPD5762 Approved
0.7241 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD4626 Approved
0.7239 Intermediate Similarity NPD1778 Approved
0.7239 Intermediate Similarity NPD7549 Discontinued
0.7239 Intermediate Similarity NPD17 Approved
0.7237 Intermediate Similarity NPD4678 Approved
0.7237 Intermediate Similarity NPD4675 Approved
0.7234 Intermediate Similarity NPD7265 Discontinued
0.7234 Intermediate Similarity NPD7477 Discontinued
0.7231 Intermediate Similarity NPD1398 Phase 1
0.723 Intermediate Similarity NPD6815 Approved
0.7222 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4108 Discontinued

  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