Structure

Physi-Chem Properties

Molecular Weight:  344.16
Volume:  356.939
LogP:  2.791
LogD:  3.108
LogS:  -4.068
# Rotatable Bonds:  6
TPSA:  68.15
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.842
Synthetic Accessibility Score:  3.155
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.664
MDCK Permeability:  2.5225164790754206e-05
Pgp-inhibitor:  0.03
Pgp-substrate:  0.236
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.02
30% Bioavailability (F30%):  0.105

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.06
Plasma Protein Binding (PPB):  97.88227081298828%
Volume Distribution (VD):  0.846
Pgp-substrate:  2.234368085861206%

ADMET: Metabolism

CYP1A2-inhibitor:  0.47
CYP1A2-substrate:  0.944
CYP2C19-inhibitor:  0.772
CYP2C19-substrate:  0.729
CYP2C9-inhibitor:  0.793
CYP2C9-substrate:  0.749
CYP2D6-inhibitor:  0.772
CYP2D6-substrate:  0.926
CYP3A4-inhibitor:  0.699
CYP3A4-substrate:  0.771

ADMET: Excretion

Clearance (CL):  14.069
Half-life (T1/2):  0.84

ADMET: Toxicity

hERG Blockers:  0.229
Human Hepatotoxicity (H-HT):  0.191
Drug-inuced Liver Injury (DILI):  0.23
AMES Toxicity:  0.098
Rat Oral Acute Toxicity:  0.031
Maximum Recommended Daily Dose:  0.71
Skin Sensitization:  0.931
Carcinogencity:  0.386
Eye Corrosion:  0.004
Eye Irritation:  0.871
Respiratory Toxicity:  0.574

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

  Natural Product: NPC317769

Natural Product ID:  NPC317769
Common Name*:   3,4-Divanillyltetrahydrofuran
IUPAC Name:   4-[[4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl]-2-methoxyphenol
Synonyms:   3,4-Divanillyltetrahydrofuran
Standard InCHIKey:  ROGUIJKVZZROIQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3
SMILES:  COC1=C(C=CC(=C1)CC2COCC2CC3=CC(=C(C=C3)O)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL405043
PubChem CID:   182210
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans
        • [CHEMONTID:0001604] Tetrahydrofuran lignans
          • [CHEMONTID:0003424] 9,9'-epoxylignans

*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
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. seed n.a. DOI[10.1016/S0031-9422(00)97029-8]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. aerial part n.a. PMID[15577228]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. fruit n.a. PMID[16417304]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. branch n.a. PMID[17202693]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota seeds n.a. n.a. PMID[18603435]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota Seeds n.a. n.a. PMID[20469887]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. PMID[22085682]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae 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
NPT895 Individual Protein Testis-specific androgen-binding protein Homo sapiens Kd = 309.03 nM PMID[482906]

☑ 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 NPC317769 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 NPC31344
0.9655 High Similarity NPC117780
0.9655 High Similarity NPC56214
0.9655 High Similarity NPC232316
0.9655 High Similarity NPC95614
0.9655 High Similarity NPC165133
0.9655 High Similarity NPC227217
0.9655 High Similarity NPC242885
0.9587 High Similarity NPC129570
0.9587 High Similarity NPC184733
0.9587 High Similarity NPC21867
0.9587 High Similarity NPC282703
0.9587 High Similarity NPC128208
0.9587 High Similarity NPC45774
0.9587 High Similarity NPC11258
0.9576 High Similarity NPC85488
0.9569 High Similarity NPC310338
0.9569 High Similarity NPC281298
0.9508 High Similarity NPC475875
0.9496 High Similarity NPC280704
0.9492 High Similarity NPC38996
0.9492 High Similarity NPC160380
0.9483 High Similarity NPC470626
0.9431 High Similarity NPC187998
0.9431 High Similarity NPC181079
0.9431 High Similarity NPC64201
0.9431 High Similarity NPC257582
0.9431 High Similarity NPC77040
0.9431 High Similarity NPC173308
0.9431 High Similarity NPC174495
0.9431 High Similarity NPC242807
0.9431 High Similarity NPC42300
0.9431 High Similarity NPC153739
0.9431 High Similarity NPC241522
0.9431 High Similarity NPC92164
0.9431 High Similarity NPC145305
0.9431 High Similarity NPC275950
0.9421 High Similarity NPC274356
0.9407 High Similarity NPC207613
0.9397 High Similarity NPC293619
0.9355 High Similarity NPC277804
0.9355 High Similarity NPC476345
0.9355 High Similarity NPC228346
0.9355 High Similarity NPC7171
0.9355 High Similarity NPC161557
0.9355 High Similarity NPC27843
0.9355 High Similarity NPC115207
0.9355 High Similarity NPC158079
0.9355 High Similarity NPC40432
0.9339 High Similarity NPC148627
0.9328 High Similarity NPC343720
0.9328 High Similarity NPC113865
0.9328 High Similarity NPC312675
0.9328 High Similarity NPC473853
0.9328 High Similarity NPC184651
0.9328 High Similarity NPC470212
0.9328 High Similarity NPC54872
0.9328 High Similarity NPC262156
0.9328 High Similarity NPC324571
0.9316 High Similarity NPC474040
0.928 High Similarity NPC181049
0.928 High Similarity NPC207400
0.9268 High Similarity NPC470084
0.9206 High Similarity NPC169973
0.9206 High Similarity NPC158331
0.9187 High Similarity NPC165045
0.9187 High Similarity NPC118533
0.9187 High Similarity NPC5428
0.918 High Similarity NPC29008
0.918 High Similarity NPC228771
0.918 High Similarity NPC9067
0.918 High Similarity NPC266705
0.9174 High Similarity NPC471693
0.9174 High Similarity NPC249788
0.9167 High Similarity NPC127389
0.9167 High Similarity NPC290451
0.9134 High Similarity NPC471942
0.9134 High Similarity NPC49603
0.9134 High Similarity NPC176814
0.9134 High Similarity NPC187616
0.9134 High Similarity NPC67247
0.9134 High Similarity NPC4982
0.9134 High Similarity NPC193026
0.9134 High Similarity NPC5310
0.9134 High Similarity NPC287745
0.9134 High Similarity NPC300776
0.9134 High Similarity NPC68779
0.9127 High Similarity NPC175067
0.9127 High Similarity NPC106739
0.9127 High Similarity NPC4940
0.9127 High Similarity NPC204215
0.9127 High Similarity NPC471505
0.9113 High Similarity NPC307050
0.9113 High Similarity NPC277458
0.9106 High Similarity NPC206882
0.9076 High Similarity NPC311595
0.9076 High Similarity NPC24474
0.9068 High Similarity NPC164386
0.9068 High Similarity NPC86947
0.9062 High Similarity NPC126409
0.9062 High Similarity NPC142547
0.9062 High Similarity NPC99572
0.9062 High Similarity NPC101624
0.9062 High Similarity NPC135777
0.9062 High Similarity NPC184938
0.9052 High Similarity NPC165106
0.9032 High Similarity NPC127587
0.9032 High Similarity NPC106511
0.9024 High Similarity NPC194519
0.9008 High Similarity NPC65933
0.9008 High Similarity NPC172676
0.9008 High Similarity NPC216929
0.9008 High Similarity NPC312713
0.9008 High Similarity NPC57268
0.9008 High Similarity NPC126935
0.8992 High Similarity NPC177160
0.8992 High Similarity NPC474214
0.8992 High Similarity NPC77861
0.8992 High Similarity NPC263367
0.8992 High Similarity NPC29799
0.8992 High Similarity NPC10737
0.8992 High Similarity NPC209985
0.8992 High Similarity NPC471988
0.8992 High Similarity NPC54743
0.8992 High Similarity NPC477939
0.8992 High Similarity NPC156502
0.8984 High Similarity NPC244983
0.8984 High Similarity NPC326095
0.8983 High Similarity NPC81067
0.8983 High Similarity NPC9341
0.8976 High Similarity NPC227002
0.896 High Similarity NPC245826
0.896 High Similarity NPC252307
0.896 High Similarity NPC474178
0.8952 High Similarity NPC213552
0.8952 High Similarity NPC120225
0.8952 High Similarity NPC76451
0.8952 High Similarity NPC178284
0.8952 High Similarity NPC58607
0.8952 High Similarity NPC304630
0.8952 High Similarity NPC17837
0.8952 High Similarity NPC191037
0.8943 High Similarity NPC293701
0.8943 High Similarity NPC48990
0.8943 High Similarity NPC114901
0.8934 High Similarity NPC30462
0.8923 High Similarity NPC281780
0.8917 High Similarity NPC474320
0.8915 High Similarity NPC24490
0.8915 High Similarity NPC141765
0.8915 High Similarity NPC165155
0.8915 High Similarity NPC34103
0.8898 High Similarity NPC473264
0.8898 High Similarity NPC474017
0.8898 High Similarity NPC47194
0.8898 High Similarity NPC475815
0.888 High Similarity NPC292056
0.888 High Similarity NPC21563
0.888 High Similarity NPC41706
0.888 High Similarity NPC118787
0.888 High Similarity NPC163332
0.888 High Similarity NPC147821
0.888 High Similarity NPC183181
0.888 High Similarity NPC319625
0.888 High Similarity NPC111247
0.8879 High Similarity NPC8547
0.8879 High Similarity NPC257124
0.8879 High Similarity NPC156840
0.8879 High Similarity NPC173746
0.8871 High Similarity NPC251855
0.8871 High Similarity NPC17943
0.8871 High Similarity NPC208950
0.8871 High Similarity NPC475169
0.8871 High Similarity NPC233410
0.8871 High Similarity NPC53305
0.8871 High Similarity NPC472093
0.8871 High Similarity NPC221077
0.8871 High Similarity NPC116907
0.8871 High Similarity NPC298757
0.8871 High Similarity NPC257589
0.8871 High Similarity NPC117214
0.8871 High Similarity NPC57490
0.8871 High Similarity NPC193544
0.8871 High Similarity NPC289459
0.8871 High Similarity NPC203133
0.8862 High Similarity NPC197757
0.8862 High Similarity NPC228922
0.8862 High Similarity NPC473451
0.8855 High Similarity NPC193666
0.8855 High Similarity NPC88640
0.8855 High Similarity NPC123526
0.8852 High Similarity NPC476343
0.8846 High Similarity NPC90431
0.8843 High Similarity NPC344161
0.8837 High Similarity NPC478085
0.8819 High Similarity NPC143483
0.881 High Similarity NPC206615
0.881 High Similarity NPC186843
0.881 High Similarity NPC98631
0.881 High Similarity NPC470213

  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 NPC317769 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
0.9052 High Similarity NPD5283 Phase 1
0.8879 High Similarity NPD228 Approved
0.874 High Similarity NPD3027 Phase 3
0.8707 High Similarity NPD3022 Approved
0.8707 High Similarity NPD3021 Approved
0.856 High Similarity NPD4379 Clinical (unspecified phase)
0.8538 High Similarity NPD3619 Clinical (unspecified phase)
0.8538 High Similarity NPD3620 Phase 2
0.8258 Intermediate Similarity NPD4060 Phase 1
0.816 Intermediate Similarity NPD1357 Approved
0.8151 Intermediate Similarity NPD2684 Approved
0.813 Intermediate Similarity NPD7157 Approved
0.8125 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD1613 Approved
0.812 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.811 Intermediate Similarity NPD3705 Approved
0.8092 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8033 Intermediate Similarity NPD7843 Approved
0.8015 Intermediate Similarity NPD2861 Phase 2
0.8015 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5536 Phase 2
0.7931 Intermediate Similarity NPD3020 Approved
0.7857 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD6331 Phase 2
0.7857 Intermediate Similarity NPD4110 Phase 3
0.7852 Intermediate Similarity NPD1558 Phase 1
0.7836 Intermediate Similarity NPD5111 Phase 2
0.7836 Intermediate Similarity NPD5109 Approved
0.7836 Intermediate Similarity NPD5110 Phase 2
0.782 Intermediate Similarity NPD4908 Phase 1
0.7803 Intermediate Similarity NPD6584 Phase 3
0.7794 Intermediate Similarity NPD6355 Discontinued
0.7778 Intermediate Similarity NPD2674 Phase 3
0.7761 Intermediate Similarity NPD7095 Approved
0.771 Intermediate Similarity NPD2982 Phase 2
0.771 Intermediate Similarity NPD2983 Phase 2
0.7704 Intermediate Similarity NPD3144 Approved
0.7704 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7704 Intermediate Similarity NPD3145 Approved
0.7698 Intermediate Similarity NPD2161 Phase 2
0.7698 Intermediate Similarity NPD6671 Approved
0.7692 Intermediate Similarity NPD1610 Phase 2
0.7692 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7686 Intermediate Similarity NPD968 Approved
0.7674 Intermediate Similarity NPD6516 Phase 2
0.7674 Intermediate Similarity NPD5846 Approved
0.7672 Intermediate Similarity NPD2860 Approved
0.7672 Intermediate Similarity NPD2859 Approved
0.7664 Intermediate Similarity NPD3657 Discovery
0.7664 Intermediate Similarity NPD5735 Approved
0.766 Intermediate Similarity NPD4236 Phase 3
0.766 Intermediate Similarity NPD4237 Approved
0.766 Intermediate Similarity NPD3060 Approved
0.7634 Intermediate Similarity NPD2981 Phase 2
0.7626 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7626 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD6234 Discontinued
0.7612 Intermediate Similarity NPD9494 Approved
0.7612 Intermediate Similarity NPD3018 Phase 2
0.7586 Intermediate Similarity NPD2934 Approved
0.7586 Intermediate Similarity NPD9296 Approved
0.7586 Intermediate Similarity NPD2933 Approved
0.7576 Intermediate Similarity NPD6582 Phase 2
0.7576 Intermediate Similarity NPD6583 Phase 3
0.7576 Intermediate Similarity NPD5327 Phase 3
0.7554 Intermediate Similarity NPD6895 Approved
0.7554 Intermediate Similarity NPD6896 Approved
0.7538 Intermediate Similarity NPD2667 Approved
0.7538 Intermediate Similarity NPD2668 Approved
0.7537 Intermediate Similarity NPD4624 Approved
0.7535 Intermediate Similarity NPD4162 Approved
0.7518 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5451 Approved
0.75 Intermediate Similarity NPD2232 Approved
0.75 Intermediate Similarity NPD2230 Approved
0.75 Intermediate Similarity NPD2233 Approved
0.7483 Intermediate Similarity NPD3882 Suspended
0.748 Intermediate Similarity NPD290 Approved
0.7467 Intermediate Similarity NPD2977 Approved
0.7467 Intermediate Similarity NPD2978 Approved
0.7465 Intermediate Similarity NPD7037 Approved
0.7464 Intermediate Similarity NPD4140 Approved
0.7464 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.746 Intermediate Similarity NPD5535 Approved
0.7445 Intermediate Similarity NPD6798 Discontinued
0.7431 Intermediate Similarity NPD5241 Discontinued
0.7424 Intermediate Similarity NPD3092 Approved
0.7413 Intermediate Similarity NPD6674 Discontinued
0.7413 Intermediate Similarity NPD5177 Phase 3
0.7405 Intermediate Similarity NPD4626 Approved
0.74 Intermediate Similarity NPD37 Approved
0.74 Intermediate Similarity NPD1934 Approved
0.7397 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7266 Discontinued
0.7394 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD1375 Discontinued
0.7394 Intermediate Similarity NPD5762 Approved
0.7394 Intermediate Similarity NPD5763 Approved
0.7388 Intermediate Similarity NPD8651 Approved
0.7388 Intermediate Similarity NPD1283 Approved
0.7388 Intermediate Similarity NPD2922 Phase 1
0.7385 Intermediate Similarity NPD1548 Phase 1
0.7385 Intermediate Similarity NPD1182 Approved
0.7385 Intermediate Similarity NPD3091 Approved
0.7376 Intermediate Similarity NPD5588 Approved
0.7368 Intermediate Similarity NPD2235 Phase 2
0.7368 Intermediate Similarity NPD2231 Phase 2
0.7368 Intermediate Similarity NPD4967 Phase 2
0.7368 Intermediate Similarity NPD1840 Phase 2
0.7368 Intermediate Similarity NPD4966 Approved
0.7368 Intermediate Similarity NPD4965 Approved
0.7361 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD8166 Discontinued
0.7357 Intermediate Similarity NPD6353 Approved
0.7357 Intermediate Similarity NPD6653 Approved
0.7355 Intermediate Similarity NPD291 Approved
0.7351 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD3847 Discontinued
0.7347 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD1358 Approved
0.7333 Intermediate Similarity NPD3094 Phase 2
0.7328 Intermediate Similarity NPD5585 Approved
0.7328 Intermediate Similarity NPD1651 Approved
0.7328 Intermediate Similarity NPD5691 Approved
0.7323 Intermediate Similarity NPD821 Approved
0.732 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD7831 Phase 2
0.732 Intermediate Similarity NPD7833 Phase 2
0.7319 Intermediate Similarity NPD5718 Phase 2
0.7313 Intermediate Similarity NPD4749 Approved
0.7313 Intermediate Similarity NPD1669 Approved
0.731 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD4538 Approved
0.7305 Intermediate Similarity NPD4536 Approved
0.7292 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD7199 Phase 2
0.7288 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD4123 Phase 3
0.7278 Intermediate Similarity NPD7228 Approved
0.7267 Intermediate Similarity NPD7028 Phase 2
0.7266 Intermediate Similarity NPD4062 Phase 3
0.7266 Intermediate Similarity NPD6233 Phase 2
0.7261 Intermediate Similarity NPD27 Approved
0.7261 Intermediate Similarity NPD2489 Approved
0.7258 Intermediate Similarity NPD3134 Approved
0.7254 Intermediate Similarity NPD4108 Discontinued
0.7246 Intermediate Similarity NPD4625 Phase 3
0.7241 Intermediate Similarity NPD4628 Phase 3
0.7239 Intermediate Similarity NPD1608 Approved
0.7237 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD2801 Approved
0.7234 Intermediate Similarity NPD2157 Approved
0.7234 Intermediate Similarity NPD4097 Suspended
0.7231 Intermediate Similarity NPD3596 Phase 2
0.723 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD52 Approved
0.723 Intermediate Similarity NPD7526 Approved
0.7226 Intermediate Similarity NPD1712 Approved
0.7222 Intermediate Similarity NPD5958 Discontinued
0.7222 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD3496 Discontinued
0.7214 Intermediate Similarity NPD2979 Phase 3
0.7214 Intermediate Similarity NPD2238 Phase 2
0.7203 Intermediate Similarity NPD2438 Suspended
0.7197 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD3685 Discontinued
0.7167 Intermediate Similarity NPD288 Approved
0.7164 Intermediate Similarity NPD1281 Approved
0.7154 Intermediate Similarity NPD709 Approved
0.7153 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5058 Phase 3
0.7143 Intermediate Similarity NPD7124 Phase 2
0.7143 Intermediate Similarity NPD3095 Discontinued
0.7133 Intermediate Similarity NPD5960 Phase 3
0.7132 Intermediate Similarity NPD6696 Suspended
0.7122 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD6580 Approved
0.7121 Intermediate Similarity NPD1894 Discontinued
0.7121 Intermediate Similarity NPD6581 Approved
0.7103 Intermediate Similarity NPD2808 Discontinued
0.7103 Intermediate Similarity NPD4534 Discontinued
0.7103 Intermediate Similarity NPD7153 Discontinued
0.7101 Intermediate Similarity NPD5736 Approved
0.7095 Intermediate Similarity NPD4357 Discontinued
0.7095 Intermediate Similarity NPD7041 Phase 2
0.7095 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD2970 Approved
0.7089 Intermediate Similarity NPD2969 Approved
0.7086 Intermediate Similarity NPD4005 Discontinued
0.7086 Intermediate Similarity NPD3866 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2935 Discontinued
0.7083 Intermediate Similarity NPD844 Approved
0.7083 Intermediate Similarity NPD6032 Approved
0.708 Intermediate Similarity NPD3053 Approved
0.708 Intermediate Similarity NPD3055 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