Structure

Physi-Chem Properties

Molecular Weight:  682.25
Volume:  635.514
LogP:  -0.369
LogD:  0.136
LogS:  -3.592
# Rotatable Bonds:  10
TPSA:  235.68
# H-Bond Aceptor:  16
# H-Bond Donor:  8
# Rings:  6
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.137
Synthetic Accessibility Score:  5.058
Fsp3:  0.625
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.54
MDCK Permeability:  7.945526158437133e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.991
Human Intestinal Absorption (HIA):  0.938
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.074
Plasma Protein Binding (PPB):  48.12436294555664%
Volume Distribution (VD):  0.52
Pgp-substrate:  14.863536834716797%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.082
CYP2C19-inhibitor:  0.006
CYP2C19-substrate:  0.279
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.083
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.172
CYP3A4-inhibitor:  0.026
CYP3A4-substrate:  0.045

ADMET: Excretion

Clearance (CL):  1.131
Half-life (T1/2):  0.478

ADMET: Toxicity

hERG Blockers:  0.538
Human Hepatotoxicity (H-HT):  0.152
Drug-inuced Liver Injury (DILI):  0.116
AMES Toxicity:  0.103
Rat Oral Acute Toxicity:  0.018
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.193
Carcinogencity:  0.134
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.013

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

  Natural Product: NPC205796

Natural Product ID:  NPC205796
Common Name*:   (-)-Pinoresinol-4,4'-Di-O-Beta-D-Glucopyranoside
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[4-[(3R,3aS,6R,6aS)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  ZJSJQWDXAYNLNS-PETZUENDSA-N
Standard InCHI:  InChI=1S/C32H42O16/c1-41-19-7-13(3-5-17(19)45-31-27(39)25(37)23(35)21(9-33)47-31)29-15-11-44-30(16(15)12-43-29)14-4-6-18(20(8-14)42-2)46-32-28(40)26(38)24(36)22(10-34)48-32/h3-8,15-16,21-40H,9-12H2,1-2H3/t15-,16-,21-,22-,23-,24-,25+,26+,27-,28-,29+,30+,31-,32-/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2ccc(cc2OC)[C@@H]2OC[C@@H]3[C@H]2CO[C@H]3c2ccc(c(c2)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL573785
PubChem CID:   45482330
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001511] Lignan 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
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[18636777]
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota stem bark Kunming, Yunnan Province, China n.a. PMID[18986199]
NPO691 Tarchonanthus camphoratus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29244495]
NPO284 Albizia procera Species Fabaceae Eukaryota Bark n.a. n.a. PMID[30520635]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23754 Solanum aculeatissimum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19432 Millettia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7616 Melanargia galathea Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3263 Thea sasanqua n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15597 Calystegia pubescens Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29287 Alectoria ochroleuca Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO691 Tarchonanthus camphoratus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO855 Elymnias thryallis Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7464 Uruparia lanosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10211 Pajanelia multijuga n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21329 Ilyonectria destructans Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1539 Artemisia giraldii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4421 Penicillium cyclopium Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5981 Achlys triphylla Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6844 Bulbophyllum protractum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3963 Hortonia floribunda Species Monimiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO284 Albizia procera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3255 Lampranthus sociorum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23754 Solanum aculeatissimum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2963 Diospyros glaucifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4952 Pertusaria amara Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3415 Perymenium mendezii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19432 Millettia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4117 Nauclea rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

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

  NP Quantity Composition/Concentration

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

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

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 300000.0 nM PMID[574193]

☑ 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 NPC205796 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 NPC276753
0.9855 High Similarity NPC471063
0.9718 High Similarity NPC475224
0.971 High Similarity NPC246947
0.9648 High Similarity NPC35877
0.9648 High Similarity NPC55715
0.9648 High Similarity NPC95392
0.9504 High Similarity NPC279298
0.9504 High Similarity NPC22150
0.9504 High Similarity NPC38041
0.9493 High Similarity NPC156376
0.9437 High Similarity NPC112861
0.9366 High Similarity NPC18979
0.9362 High Similarity NPC185307
0.9362 High Similarity NPC477898
0.9362 High Similarity NPC113680
0.9362 High Similarity NPC470950
0.9362 High Similarity NPC278961
0.9357 High Similarity NPC471908
0.9301 High Similarity NPC241846
0.9301 High Similarity NPC93610
0.9296 High Similarity NPC217635
0.9296 High Similarity NPC84181
0.9296 High Similarity NPC471667
0.9296 High Similarity NPC470235
0.9296 High Similarity NPC283995
0.9296 High Similarity NPC79429
0.9296 High Similarity NPC129417
0.9291 High Similarity NPC302506
0.9291 High Similarity NPC476356
0.9241 High Similarity NPC55158
0.9241 High Similarity NPC51328
0.9241 High Similarity NPC286235
0.9231 High Similarity NPC43508
0.9231 High Similarity NPC476301
0.9225 High Similarity NPC46092
0.922 High Similarity NPC472711
0.9203 High Similarity NPC476411
0.9203 High Similarity NPC187194
0.9178 High Similarity NPC238140
0.9178 High Similarity NPC98624
0.9172 High Similarity NPC226153
0.9172 High Similarity NPC248132
0.9172 High Similarity NPC130449
0.9172 High Similarity NPC304048
0.9161 High Similarity NPC179521
0.9149 High Similarity NPC106944
0.9103 High Similarity NPC39657
0.9103 High Similarity NPC114505
0.9103 High Similarity NPC15956
0.9103 High Similarity NPC31325
0.9103 High Similarity NPC213074
0.9103 High Similarity NPC275284
0.9103 High Similarity NPC193473
0.9103 High Similarity NPC224674
0.9097 High Similarity NPC469586
0.9067 High Similarity NPC11411
0.9041 High Similarity NPC270751
0.9014 High Similarity NPC226547
0.9007 High Similarity NPC470413
0.9007 High Similarity NPC138738
0.8986 High Similarity NPC9912
0.8973 High Similarity NPC99183
0.8954 High Similarity NPC7191
0.8954 High Similarity NPC149873
0.8951 High Similarity NPC76871
0.8936 High Similarity NPC177035
0.8936 High Similarity NPC52277
0.8936 High Similarity NPC199459
0.8929 High Similarity NPC47181
0.8921 High Similarity NPC259742
0.8921 High Similarity NPC104077
0.8921 High Similarity NPC147616
0.8921 High Similarity NPC219671
0.8919 High Similarity NPC229882
0.8919 High Similarity NPC158635
0.8913 High Similarity NPC80600
0.8913 High Similarity NPC472024
0.8897 High Similarity NPC472712
0.8897 High Similarity NPC187774
0.8897 High Similarity NPC472713
0.8897 High Similarity NPC118385
0.8897 High Similarity NPC473046
0.8889 High Similarity NPC60249
0.8881 High Similarity NPC55793
0.8873 High Similarity NPC469981
0.8873 High Similarity NPC185908
0.8873 High Similarity NPC283949
0.8873 High Similarity NPC304152
0.8865 High Similarity NPC135777
0.8865 High Similarity NPC101624
0.8865 High Similarity NPC142547
0.8865 High Similarity NPC93783
0.8865 High Similarity NPC184938
0.8865 High Similarity NPC18576
0.8857 High Similarity NPC25821
0.8851 High Similarity NPC44452
0.8841 High Similarity NPC270849
0.8841 High Similarity NPC26653
0.8836 High Similarity NPC286245
0.8836 High Similarity NPC272619
0.8819 High Similarity NPC108674
0.8811 High Similarity NPC123526
0.8811 High Similarity NPC193666
0.8811 High Similarity NPC260842
0.8811 High Similarity NPC88640
0.88 High Similarity NPC478268
0.88 High Similarity NPC302610
0.8794 High Similarity NPC35731
0.8792 High Similarity NPC470934
0.8792 High Similarity NPC472710
0.8792 High Similarity NPC472709
0.8792 High Similarity NPC188393
0.8776 High Similarity NPC125755
0.8768 High Similarity NPC302378
0.8768 High Similarity NPC165128
0.8768 High Similarity NPC158471
0.8768 High Similarity NPC57119
0.8768 High Similarity NPC226862
0.8767 High Similarity NPC471065
0.8767 High Similarity NPC473045
0.8767 High Similarity NPC25292
0.8767 High Similarity NPC253015
0.8759 High Similarity NPC5262
0.8759 High Similarity NPC469559
0.8759 High Similarity NPC189115
0.8759 High Similarity NPC472714
0.8759 High Similarity NPC253878
0.875 High Similarity NPC56091
0.875 High Similarity NPC46591
0.875 High Similarity NPC186316
0.8742 High Similarity NPC115466
0.8742 High Similarity NPC61604
0.8742 High Similarity NPC245615
0.8742 High Similarity NPC299706
0.8741 High Similarity NPC101807
0.8733 High Similarity NPC473621
0.8732 High Similarity NPC150534
0.8732 High Similarity NPC470236
0.8732 High Similarity NPC236522
0.8732 High Similarity NPC174191
0.8726 High Similarity NPC59516
0.8725 High Similarity NPC470098
0.8725 High Similarity NPC473266
0.8725 High Similarity NPC470826
0.8723 High Similarity NPC169973
0.8714 High Similarity NPC82111
0.8714 High Similarity NPC227160
0.8707 High Similarity NPC277867
0.8707 High Similarity NPC161700
0.8707 High Similarity NPC475096
0.8705 High Similarity NPC248355
0.8705 High Similarity NPC166040
0.8701 High Similarity NPC478269
0.8699 High Similarity NPC473044
0.8693 High Similarity NPC478055
0.869 High Similarity NPC470372
0.869 High Similarity NPC469661
0.869 High Similarity NPC471414
0.8675 High Similarity NPC474442
0.8671 High Similarity NPC25695
0.8671 High Similarity NPC164857
0.8671 High Similarity NPC77861
0.8671 High Similarity NPC172818
0.8662 High Similarity NPC90083
0.8662 High Similarity NPC170779
0.8662 High Similarity NPC470881
0.8658 High Similarity NPC301961
0.8658 High Similarity NPC280945
0.8658 High Similarity NPC116229
0.8658 High Similarity NPC166584
0.8652 High Similarity NPC7744
0.8652 High Similarity NPC254275
0.8652 High Similarity NPC471505
0.8652 High Similarity NPC106739
0.8649 High Similarity NPC162193
0.8649 High Similarity NPC99515
0.8649 High Similarity NPC476865
0.8649 High Similarity NPC190714
0.8643 High Similarity NPC134764
0.8643 High Similarity NPC171550
0.8643 High Similarity NPC233224
0.8643 High Similarity NPC271208
0.8639 High Similarity NPC168579
0.8639 High Similarity NPC469313
0.8639 High Similarity NPC470097
0.8639 High Similarity NPC114119
0.8639 High Similarity NPC471415
0.8639 High Similarity NPC76176
0.8639 High Similarity NPC138227
0.8633 High Similarity NPC470084
0.863 High Similarity NPC473792
0.863 High Similarity NPC473873
0.863 High Similarity NPC287124
0.863 High Similarity NPC80326
0.863 High Similarity NPC48309
0.8623 High Similarity NPC213711
0.8623 High Similarity NPC206882
0.8623 High Similarity NPC40352
0.8621 High Similarity NPC177868

  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 NPC205796 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
0.8435 Intermediate Similarity NPD6674 Discontinued
0.821 Intermediate Similarity NPD7228 Approved
0.8176 Intermediate Similarity NPD7266 Discontinued
0.8121 Intermediate Similarity NPD7240 Approved
0.8 Intermediate Similarity NPD3705 Approved
0.7987 Intermediate Similarity NPD4967 Phase 2
0.7987 Intermediate Similarity NPD4966 Approved
0.7987 Intermediate Similarity NPD4965 Approved
0.7975 Intermediate Similarity NPD8455 Phase 2
0.7931 Intermediate Similarity NPD3027 Phase 3
0.7901 Intermediate Similarity NPD7199 Phase 2
0.7891 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD1613 Approved
0.7888 Intermediate Similarity NPD6234 Discontinued
0.7799 Intermediate Similarity NPD37 Approved
0.7792 Intermediate Similarity NPD5058 Phase 3
0.7784 Intermediate Similarity NPD7472 Approved
0.7784 Intermediate Similarity NPD7074 Phase 3
0.7751 Intermediate Similarity NPD7808 Phase 3
0.7746 Intermediate Similarity NPD1091 Approved
0.7725 Intermediate Similarity NPD7054 Approved
0.7697 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD2861 Phase 2
0.766 Intermediate Similarity NPD1357 Approved
0.7658 Intermediate Similarity NPD1653 Approved
0.7628 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD5283 Phase 1
0.7588 Intermediate Similarity NPD7251 Discontinued
0.7588 Intermediate Similarity NPD7685 Pre-registration
0.756 Intermediate Similarity NPD3818 Discontinued
0.7551 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD7843 Approved
0.7529 Intermediate Similarity NPD6797 Phase 2
0.7514 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7157 Approved
0.75 Intermediate Similarity NPD4908 Phase 1
0.7484 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD5735 Approved
0.7451 Intermediate Similarity NPD5588 Approved
0.74 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4538 Approved
0.7386 Intermediate Similarity NPD4536 Approved
0.7386 Intermediate Similarity NPD7097 Phase 1
0.7377 Intermediate Similarity NPD7680 Approved
0.7365 Intermediate Similarity NPD8127 Discontinued
0.7361 Intermediate Similarity NPD5125 Phase 3
0.7361 Intermediate Similarity NPD5126 Approved
0.7355 Intermediate Similarity NPD1375 Discontinued
0.7348 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD8651 Approved
0.731 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD3620 Phase 2
0.7303 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD8312 Approved
0.7299 Intermediate Similarity NPD8313 Approved
0.7289 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD1610 Phase 2
0.7255 Intermediate Similarity NPD6355 Discontinued
0.7246 Intermediate Similarity NPD2684 Approved
0.7244 Intermediate Similarity NPD5762 Approved
0.7244 Intermediate Similarity NPD5763 Approved
0.7241 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6166 Phase 2
0.7226 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD4108 Discontinued
0.7226 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD5960 Phase 3
0.7219 Intermediate Similarity NPD7095 Approved
0.7215 Intermediate Similarity NPD4110 Phase 3
0.7215 Intermediate Similarity NPD6331 Phase 2
0.7215 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD2978 Approved
0.7212 Intermediate Similarity NPD2977 Approved
0.7202 Intermediate Similarity NPD5494 Approved
0.719 Intermediate Similarity NPD4060 Phase 1
0.7184 Intermediate Similarity NPD6559 Discontinued
0.7169 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD2983 Phase 2
0.7162 Intermediate Similarity NPD2982 Phase 2
0.716 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD4237 Approved
0.7152 Intermediate Similarity NPD1934 Approved
0.7152 Intermediate Similarity NPD4236 Phase 3
0.7134 Intermediate Similarity NPD7028 Phase 2
0.7126 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD3051 Approved
0.7097 Intermediate Similarity NPD6653 Approved
0.7095 Intermediate Similarity NPD2981 Phase 2
0.7092 Intermediate Similarity NPD228 Approved
0.7086 Intermediate Similarity NPD3018 Phase 2
0.7078 Intermediate Similarity NPD4140 Approved
0.7076 Intermediate Similarity NPD2970 Approved
0.7076 Intermediate Similarity NPD2969 Approved
0.7073 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD2161 Phase 2
0.7063 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD5327 Phase 3
0.7037 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD3787 Discontinued
0.7013 Intermediate Similarity NPD6233 Phase 2
0.7011 Intermediate Similarity NPD5844 Phase 1
0.7007 Intermediate Similarity NPD5846 Approved
0.7007 Intermediate Similarity NPD6516 Phase 2
0.7006 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5773 Approved
0.7006 Intermediate Similarity NPD5772 Approved
0.7 Intermediate Similarity NPD4628 Phase 3
0.6994 Remote Similarity NPD7526 Approved
0.6994 Remote Similarity NPD52 Approved
0.6994 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6987 Remote Similarity NPD6353 Approved
0.6968 Remote Similarity NPD1558 Phase 1
0.6964 Remote Similarity NPD3817 Phase 2
0.6957 Remote Similarity NPD2677 Approved
0.695 Remote Similarity NPD3021 Approved
0.695 Remote Similarity NPD3022 Approved
0.6948 Remote Similarity NPD6798 Discontinued
0.6946 Remote Similarity NPD3384 Approved
0.6946 Remote Similarity NPD3383 Approved
0.6946 Remote Similarity NPD3382 Approved
0.6944 Remote Similarity NPD7906 Approved
0.6944 Remote Similarity NPD6842 Approved
0.6944 Remote Similarity NPD6841 Approved
0.6944 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6843 Phase 3
0.6937 Remote Similarity NPD5177 Phase 3
0.6937 Remote Similarity NPD4162 Approved
0.6936 Remote Similarity NPD27 Approved
0.6936 Remote Similarity NPD2489 Approved
0.6933 Remote Similarity NPD4749 Approved
0.6933 Remote Similarity NPD3685 Discontinued
0.6933 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6929 Remote Similarity NPD290 Approved
0.6928 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6071 Discontinued
0.691 Remote Similarity NPD7313 Approved
0.691 Remote Similarity NPD7312 Approved
0.691 Remote Similarity NPD7311 Approved
0.691 Remote Similarity NPD7310 Approved
0.6909 Remote Similarity NPD4210 Discontinued
0.6905 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6903 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6671 Approved
0.6894 Remote Similarity NPD4535 Phase 3
0.6894 Remote Similarity NPD6658 Clinical (unspecified phase)
0.689 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6883 Remote Similarity NPD4625 Phase 3
0.6872 Remote Similarity NPD7309 Approved
0.6871 Remote Similarity NPD1548 Phase 1
0.6867 Remote Similarity NPD1608 Approved
0.6864 Remote Similarity NPD2560 Approved
0.6864 Remote Similarity NPD2563 Approved
0.6859 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6848 Remote Similarity NPD2122 Discontinued
0.6839 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6835 Remote Similarity NPD7119 Phase 2
0.6832 Remote Similarity NPD3060 Approved
0.6832 Remote Similarity NPD1652 Phase 2
0.6829 Remote Similarity NPD4123 Phase 3
0.6824 Remote Similarity NPD3882 Suspended
0.6815 Remote Similarity NPD3657 Discovery
0.6815 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5124 Phase 1
0.6813 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6005 Phase 3
0.6813 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6004 Phase 3
0.6813 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6002 Phase 3
0.6813 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6812 Remote Similarity NPD291 Approved
0.6807 Remote Similarity NPD3686 Approved
0.6807 Remote Similarity NPD3687 Approved
0.6806 Remote Similarity NPD5535 Approved
0.6805 Remote Similarity NPD2801 Approved
0.6805 Remote Similarity NPD1465 Phase 2
0.6805 Remote Similarity NPD7819 Suspended
0.6803 Remote Similarity NPD5536 Phase 2
0.6797 Remote Similarity NPD6584 Phase 3
0.6796 Remote Similarity NPD4663 Approved
0.6792 Remote Similarity NPD7033 Discontinued
0.679 Remote Similarity NPD7466 Approved
0.6788 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4773 Phase 2
0.6786 Remote Similarity NPD4772 Phase 2
0.6784 Remote Similarity NPD5604 Discontinued
0.6784 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6784 Remote Similarity NPD7833 Phase 2

  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