Structure

Physi-Chem Properties

Molecular Weight:  344.2
Volume:  374.001
LogP:  3.523
LogD:  3.229
LogS:  -5.285
# Rotatable Bonds:  10
TPSA:  58.92
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.694
Synthetic Accessibility Score:  2.626
Fsp3:  0.429
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:  -4.933
MDCK Permeability:  8.407370842178352e-06
Pgp-inhibitor:  0.997
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.105
30% Bioavailability (F30%):  0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.636
Plasma Protein Binding (PPB):  95.79944610595703%
Volume Distribution (VD):  0.842
Pgp-substrate:  0.8070578575134277%

ADMET: Metabolism

CYP1A2-inhibitor:  0.754
CYP1A2-substrate:  0.962
CYP2C19-inhibitor:  0.926
CYP2C19-substrate:  0.717
CYP2C9-inhibitor:  0.883
CYP2C9-substrate:  0.904
CYP2D6-inhibitor:  0.637
CYP2D6-substrate:  0.915
CYP3A4-inhibitor:  0.554
CYP3A4-substrate:  0.89

ADMET: Excretion

Clearance (CL):  12.11
Half-life (T1/2):  0.238

ADMET: Toxicity

hERG Blockers:  0.877
Human Hepatotoxicity (H-HT):  0.227
Drug-inuced Liver Injury (DILI):  0.038
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.006
Maximum Recommended Daily Dose:  0.974
Skin Sensitization:  0.954
Carcinogencity:  0.121
Eye Corrosion:  0.136
Eye Irritation:  0.927
Respiratory Toxicity:  0.053

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

  Natural Product: NPC474272

Natural Product ID:  NPC474272
Common Name*:   (3R,5R)-1,7-Bis(4-Methoxyphenyl)Heptane-3,5-Diol
IUPAC Name:   (3R,5R)-1,7-bis(4-methoxyphenyl)heptane-3,5-diol
Synonyms:  
Standard InCHIKey:  LABGDRVCJRMZIR-RTBURBONSA-N
Standard InCHI:  InChI=1S/C21H28O4/c1-24-20-11-5-16(6-12-20)3-9-18(22)15-19(23)10-4-17-7-13-21(25-2)14-8-17/h5-8,11-14,18-19,22-23H,3-4,9-10,15H2,1-2H3/t18-,19-/m1/s1
SMILES:  COc1ccc(cc1)CC[C@H](C[C@@H](CCc1ccc(cc1)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464572
PubChem CID:   10914910
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002650] Diarylheptanoids
        • [CHEMONTID:0002651] Linear diarylheptanoids
          • [CHEMONTID:0000356] Curcuminoids

*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
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota rhizomes SiMao City, Yunnan Province, China 1996-OCT PMID[11908966]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota Rhizomes n.a. n.a. PMID[12350150]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. PMID[20715765]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. PMID[33253561]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13332 Tacca chantrieri Species Taccaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 6.4 ug.mL-1 PMID[527241]
NPT924 Cell Line HSC-2 Homo sapiens IC50 = 23.0 ug.mL-1 PMID[527241]
NPT27 Others Unspecified IC50 = 173.0 ug.mL-1 PMID[527241]

☑ 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 NPC474272 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
0.932 High Similarity NPC113457
0.9223 High Similarity NPC233396
0.9223 High Similarity NPC154899
0.9182 High Similarity NPC474214
0.9135 High Similarity NPC135464
0.9135 High Similarity NPC92623
0.9109 High Similarity NPC100870
0.9099 High Similarity NPC474320
0.9038 High Similarity NPC470393
0.8962 High Similarity NPC75440
0.8962 High Similarity NPC201959
0.8942 High Similarity NPC108875
0.8942 High Similarity NPC38079
0.8932 High Similarity NPC91461
0.8932 High Similarity NPC40258
0.8932 High Similarity NPC7686
0.886 High Similarity NPC262156
0.886 High Similarity NPC473853
0.886 High Similarity NPC184651
0.886 High Similarity NPC312675
0.886 High Similarity NPC113865
0.886 High Similarity NPC343720
0.886 High Similarity NPC54872
0.886 High Similarity NPC470212
0.886 High Similarity NPC324571
0.8839 High Similarity NPC474040
0.8835 High Similarity NPC213730
0.8807 High Similarity NPC153795
0.8807 High Similarity NPC290353
0.8807 High Similarity NPC42911
0.8772 High Similarity NPC207613
0.875 High Similarity NPC300166
0.8738 High Similarity NPC216468
0.8738 High Similarity NPC132078
0.8738 High Similarity NPC51333
0.8738 High Similarity NPC78119
0.8727 High Similarity NPC35344
0.8727 High Similarity NPC141003
0.8692 High Similarity NPC251306
0.8667 High Similarity NPC192596
0.8667 High Similarity NPC305205
0.8661 High Similarity NPC229147
0.8661 High Similarity NPC85292
0.8661 High Similarity NPC54507
0.8624 High Similarity NPC63345
0.8624 High Similarity NPC46844
0.8596 High Similarity NPC311595
0.8596 High Similarity NPC24474
0.8585 High Similarity NPC474603
0.8585 High Similarity NPC12987
0.8584 High Similarity NPC476266
0.8584 High Similarity NPC474933
0.8571 High Similarity NPC185541
0.8571 High Similarity NPC51633
0.8571 High Similarity NPC464
0.8547 High Similarity NPC471693
0.8547 High Similarity NPC76465
0.8547 High Similarity NPC38761
0.8547 High Similarity NPC474160
0.8547 High Similarity NPC280704
0.8532 High Similarity NPC306045
0.8532 High Similarity NPC265211
0.8515 High Similarity NPC321956
0.8509 High Similarity NPC470626
0.8509 High Similarity NPC131118
0.8496 Intermediate Similarity NPC141090
0.8496 Intermediate Similarity NPC473556
0.8496 Intermediate Similarity NPC301651
0.8487 Intermediate Similarity NPC276212
0.8487 Intermediate Similarity NPC206882
0.8475 Intermediate Similarity NPC48990
0.8475 Intermediate Similarity NPC114901
0.8475 Intermediate Similarity NPC293701
0.8462 Intermediate Similarity NPC100099
0.8462 Intermediate Similarity NPC36016
0.8462 Intermediate Similarity NPC85488
0.8462 Intermediate Similarity NPC71090
0.8455 Intermediate Similarity NPC475852
0.8455 Intermediate Similarity NPC137685
0.8447 Intermediate Similarity NPC26244
0.8435 Intermediate Similarity NPC163036
0.8435 Intermediate Similarity NPC59561
0.8435 Intermediate Similarity NPC172253
0.8421 Intermediate Similarity NPC470759
0.8421 Intermediate Similarity NPC15860
0.8421 Intermediate Similarity NPC293619
0.8421 Intermediate Similarity NPC164386
0.8421 Intermediate Similarity NPC219070
0.8421 Intermediate Similarity NPC127894
0.8417 Intermediate Similarity NPC165045
0.8417 Intermediate Similarity NPC242032
0.8417 Intermediate Similarity NPC118533
0.8416 Intermediate Similarity NPC71853
0.8407 Intermediate Similarity NPC296526
0.8407 Intermediate Similarity NPC53906
0.8403 Intermediate Similarity NPC102540
0.8403 Intermediate Similarity NPC81641
0.8403 Intermediate Similarity NPC148627
0.8403 Intermediate Similarity NPC285040
0.8403 Intermediate Similarity NPC188022
0.8403 Intermediate Similarity NPC103420
0.8403 Intermediate Similarity NPC17809
0.8393 Intermediate Similarity NPC165106
0.8393 Intermediate Similarity NPC123175
0.8393 Intermediate Similarity NPC176730
0.8376 Intermediate Similarity NPC127389
0.8376 Intermediate Similarity NPC290451
0.8376 Intermediate Similarity NPC251259
0.8376 Intermediate Similarity NPC476633
0.8365 Intermediate Similarity NPC473388
0.8362 Intermediate Similarity NPC165133
0.8362 Intermediate Similarity NPC232316
0.8362 Intermediate Similarity NPC242885
0.8362 Intermediate Similarity NPC56214
0.8362 Intermediate Similarity NPC117780
0.8362 Intermediate Similarity NPC227217
0.8362 Intermediate Similarity NPC95614
0.835 Intermediate Similarity NPC151715
0.835 Intermediate Similarity NPC471581
0.8349 Intermediate Similarity NPC194034
0.8347 Intermediate Similarity NPC274717
0.8347 Intermediate Similarity NPC245826
0.8347 Intermediate Similarity NPC186843
0.8347 Intermediate Similarity NPC98631
0.8347 Intermediate Similarity NPC206615
0.8347 Intermediate Similarity NPC252307
0.8347 Intermediate Similarity NPC474178
0.8347 Intermediate Similarity NPC470084
0.8347 Intermediate Similarity NPC470213
0.8333 Intermediate Similarity NPC9341
0.8333 Intermediate Similarity NPC81067
0.8333 Intermediate Similarity NPC114064
0.8333 Intermediate Similarity NPC8302
0.8333 Intermediate Similarity NPC19290
0.8319 Intermediate Similarity NPC197351
0.8319 Intermediate Similarity NPC276737
0.8319 Intermediate Similarity NPC228287
0.8319 Intermediate Similarity NPC94276
0.8319 Intermediate Similarity NPC109822
0.8319 Intermediate Similarity NPC106914
0.8319 Intermediate Similarity NPC86502
0.8319 Intermediate Similarity NPC470837
0.8319 Intermediate Similarity NPC134195
0.8319 Intermediate Similarity NPC180508
0.8319 Intermediate Similarity NPC246648
0.8319 Intermediate Similarity NPC22610
0.8317 Intermediate Similarity NPC8002
0.8317 Intermediate Similarity NPC99886
0.8317 Intermediate Similarity NPC259134
0.8317 Intermediate Similarity NPC177844
0.8305 Intermediate Similarity NPC152946
0.8305 Intermediate Similarity NPC18128
0.8305 Intermediate Similarity NPC77789
0.8305 Intermediate Similarity NPC150026
0.8305 Intermediate Similarity NPC476142
0.8305 Intermediate Similarity NPC188997
0.8302 Intermediate Similarity NPC294741
0.8291 Intermediate Similarity NPC131868
0.8288 Intermediate Similarity NPC2682
0.8288 Intermediate Similarity NPC475018
0.8286 Intermediate Similarity NPC470161
0.8279 Intermediate Similarity NPC212015
0.8279 Intermediate Similarity NPC476968
0.8279 Intermediate Similarity NPC170844
0.8279 Intermediate Similarity NPC469951
0.8279 Intermediate Similarity NPC469963
0.8279 Intermediate Similarity NPC475875
0.8276 Intermediate Similarity NPC281298
0.8276 Intermediate Similarity NPC135961
0.8276 Intermediate Similarity NPC310338
0.8264 Intermediate Similarity NPC118787
0.8264 Intermediate Similarity NPC41706
0.8264 Intermediate Similarity NPC319625
0.8264 Intermediate Similarity NPC183181
0.8264 Intermediate Similarity NPC163332
0.8264 Intermediate Similarity NPC111247
0.8264 Intermediate Similarity NPC292056
0.8264 Intermediate Similarity NPC474119
0.8264 Intermediate Similarity NPC147821
0.8264 Intermediate Similarity NPC5428
0.8261 Intermediate Similarity NPC195466
0.8261 Intermediate Similarity NPC69261
0.8261 Intermediate Similarity NPC33270
0.8257 Intermediate Similarity NPC326801
0.8252 Intermediate Similarity NPC138117
0.8252 Intermediate Similarity NPC325292
0.825 Intermediate Similarity NPC194519
0.825 Intermediate Similarity NPC4286
0.825 Intermediate Similarity NPC76119
0.8246 Intermediate Similarity NPC475815
0.8246 Intermediate Similarity NPC47194
0.8246 Intermediate Similarity NPC808
0.8246 Intermediate Similarity NPC473264
0.8246 Intermediate Similarity NPC51345
0.8241 Intermediate Similarity NPC241224
0.8235 Intermediate Similarity NPC317769
0.8235 Intermediate Similarity NPC31344
0.8235 Intermediate Similarity NPC282496
0.8235 Intermediate Similarity NPC261992
0.8235 Intermediate Similarity NPC136319

  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 NPC474272 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
0.8785 High Similarity NPD2684 Approved
0.8636 High Similarity NPD7843 Approved
0.8532 High Similarity NPD5451 Approved
0.8447 Intermediate Similarity NPD2860 Approved
0.8447 Intermediate Similarity NPD2859 Approved
0.8407 Intermediate Similarity NPD7157 Approved
0.8393 Intermediate Similarity NPD5283 Phase 1
0.835 Intermediate Similarity NPD2934 Approved
0.835 Intermediate Similarity NPD2933 Approved
0.8349 Intermediate Similarity NPD290 Approved
0.8304 Intermediate Similarity NPD5535 Approved
0.8291 Intermediate Similarity NPD3847 Discontinued
0.8279 Intermediate Similarity NPD3027 Phase 3
0.8257 Intermediate Similarity NPD968 Approved
0.8208 Intermediate Similarity NPD3020 Approved
0.8205 Intermediate Similarity NPD5846 Approved
0.8205 Intermediate Similarity NPD6516 Phase 2
0.8142 Intermediate Similarity NPD821 Approved
0.8083 Intermediate Similarity NPD3685 Discontinued
0.8083 Intermediate Similarity NPD6582 Phase 2
0.8083 Intermediate Similarity NPD6583 Phase 3
0.8083 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.8051 Intermediate Similarity NPD2667 Approved
0.8051 Intermediate Similarity NPD2668 Approved
0.8049 Intermediate Similarity NPD4908 Phase 1
0.8034 Intermediate Similarity NPD1548 Phase 1
0.8017 Intermediate Similarity NPD3596 Phase 2
0.7928 Intermediate Similarity NPD3134 Approved
0.792 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.792 Intermediate Similarity NPD6798 Discontinued
0.7917 Intermediate Similarity NPD1610 Phase 2
0.7895 Intermediate Similarity NPD228 Approved
0.7891 Intermediate Similarity NPD4538 Approved
0.7891 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD4536 Approved
0.7886 Intermediate Similarity NPD6584 Phase 3
0.7881 Intermediate Similarity NPD1894 Discontinued
0.7881 Intermediate Similarity NPD6580 Approved
0.7881 Intermediate Similarity NPD6581 Approved
0.7857 Intermediate Similarity NPD6233 Phase 2
0.7857 Intermediate Similarity NPD1358 Approved
0.7823 Intermediate Similarity NPD2861 Phase 2
0.7815 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD3028 Approved
0.7778 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6671 Approved
0.7778 Intermediate Similarity NPD2557 Approved
0.7742 Intermediate Similarity NPD3691 Phase 2
0.7742 Intermediate Similarity NPD3690 Phase 2
0.7734 Intermediate Similarity NPD6355 Discontinued
0.7724 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD3021 Approved
0.7719 Intermediate Similarity NPD3022 Approved
0.7717 Intermediate Similarity NPD4062 Phase 3
0.7705 Intermediate Similarity NPD2231 Phase 2
0.7705 Intermediate Similarity NPD2235 Phase 2
0.7692 Intermediate Similarity NPD5588 Approved
0.7692 Intermediate Similarity NPD5960 Phase 3
0.7667 Intermediate Similarity NPD1651 Approved
0.7667 Intermediate Similarity NPD1357 Approved
0.7664 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD4140 Approved
0.7656 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD2238 Phase 2
0.7656 Intermediate Similarity NPD4060 Phase 1
0.7656 Intermediate Similarity NPD1613 Approved
0.7656 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD5536 Phase 2
0.7642 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7642 Intermediate Similarity NPD1669 Approved
0.7642 Intermediate Similarity NPD5327 Phase 3
0.7638 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD6387 Discontinued
0.7623 Intermediate Similarity NPD1091 Approved
0.7607 Intermediate Similarity NPD1241 Discontinued
0.7603 Intermediate Similarity NPD4626 Approved
0.76 Intermediate Similarity NPD4624 Approved
0.7597 Intermediate Similarity NPD5735 Approved
0.7594 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7581 Intermediate Similarity NPD1283 Approved
0.7581 Intermediate Similarity NPD8651 Approved
0.7568 Intermediate Similarity NPD291 Approved
0.7568 Intermediate Similarity NPD940 Approved
0.7568 Intermediate Similarity NPD846 Approved
0.7561 Intermediate Similarity NPD3972 Approved
0.7561 Intermediate Similarity NPD2232 Approved
0.7561 Intermediate Similarity NPD2230 Approved
0.7561 Intermediate Similarity NPD2233 Approved
0.7559 Intermediate Similarity NPD7095 Approved
0.7559 Intermediate Similarity NPD5163 Phase 2
0.7559 Intermediate Similarity NPD6179 Discontinued
0.7557 Intermediate Similarity NPD7033 Discontinued
0.7538 Intermediate Similarity NPD3054 Approved
0.7538 Intermediate Similarity NPD3052 Approved
0.7537 Intermediate Similarity NPD4535 Phase 3
0.7521 Intermediate Similarity NPD1138 Approved
0.7521 Intermediate Similarity NPD3443 Approved
0.7521 Intermediate Similarity NPD5691 Approved
0.7521 Intermediate Similarity NPD3444 Approved
0.7521 Intermediate Similarity NPD3445 Approved
0.7521 Intermediate Similarity NPD3049 Approved
0.752 Intermediate Similarity NPD2797 Approved
0.7519 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD3620 Phase 2
0.75 Intermediate Similarity NPD2982 Phase 2
0.75 Intermediate Similarity NPD6540 Phase 3
0.75 Intermediate Similarity NPD6542 Approved
0.75 Intermediate Similarity NPD2428 Approved
0.75 Intermediate Similarity NPD6543 Approved
0.75 Intermediate Similarity NPD6539 Approved
0.75 Intermediate Similarity NPD2983 Phase 2
0.75 Intermediate Similarity NPD2429 Approved
0.75 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD7097 Phase 1
0.748 Intermediate Similarity NPD1535 Discovery
0.7479 Intermediate Similarity NPD709 Approved
0.7476 Intermediate Similarity NPD111 Approved
0.746 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD2554 Approved
0.7459 Intermediate Similarity NPD2556 Approved
0.7459 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD3095 Discontinued
0.7442 Intermediate Similarity NPD7265 Discontinued
0.7442 Intermediate Similarity NPD3058 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD6538 Approved
0.744 Intermediate Similarity NPD6541 Approved
0.7438 Intermediate Similarity NPD3091 Approved
0.7438 Intermediate Similarity NPD1182 Approved
0.7436 Intermediate Similarity NPD1137 Approved
0.7436 Intermediate Similarity NPD1139 Approved
0.7426 Intermediate Similarity NPD5058 Phase 3
0.7424 Intermediate Similarity NPD4108 Discontinued
0.7419 Intermediate Similarity NPD2981 Phase 2
0.7419 Intermediate Similarity NPD1481 Phase 2
0.7407 Intermediate Similarity NPD4628 Phase 3
0.7405 Intermediate Similarity NPD6353 Approved
0.7402 Intermediate Similarity NPD3018 Phase 2
0.7398 Intermediate Similarity NPD3496 Discontinued
0.7388 Intermediate Similarity NPD2424 Discontinued
0.7385 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD9365 Approved
0.7381 Intermediate Similarity NPD1820 Approved
0.7381 Intermediate Similarity NPD1818 Approved
0.7381 Intermediate Similarity NPD6362 Approved
0.7381 Intermediate Similarity NPD1819 Approved
0.7381 Intermediate Similarity NPD1817 Approved
0.7377 Intermediate Similarity NPD5585 Approved
0.7368 Intermediate Similarity NPD2935 Discontinued
0.7364 Intermediate Similarity NPD3268 Approved
0.7358 Intermediate Similarity NPD9295 Approved
0.7344 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD422 Phase 1
0.7339 Intermediate Similarity NPD1281 Approved
0.7333 Intermediate Similarity NPD3060 Approved
0.7328 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD5124 Phase 1
0.7323 Intermediate Similarity NPD7018 Phase 2
0.7323 Intermediate Similarity NPD558 Phase 2
0.7321 Intermediate Similarity NPD1242 Phase 1
0.7308 Intermediate Similarity NPD7477 Discontinued
0.7302 Intermediate Similarity NPD1876 Approved
0.7293 Intermediate Similarity NPD3846 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD3164 Approved
0.7287 Intermediate Similarity NPD3167 Approved
0.7287 Intermediate Similarity NPD3179 Approved
0.7287 Intermediate Similarity NPD3180 Approved
0.7287 Intermediate Similarity NPD4625 Phase 3
0.7287 Intermediate Similarity NPD3165 Approved
0.7287 Intermediate Similarity NPD3166 Approved
0.728 Intermediate Similarity NPD1608 Approved
0.728 Intermediate Similarity NPD1840 Phase 2
0.7273 Intermediate Similarity NPD1809 Phase 2
0.7273 Intermediate Similarity NPD844 Approved
0.7273 Intermediate Similarity NPD4097 Suspended
0.7266 Intermediate Similarity NPD4993 Discontinued
0.7266 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD4534 Discontinued
0.7252 Intermediate Similarity NPD1240 Approved
0.7252 Intermediate Similarity NPD2979 Phase 3
0.7248 Intermediate Similarity NPD845 Approved
0.7246 Intermediate Similarity NPD7213 Phase 3
0.7246 Intermediate Similarity NPD7212 Phase 2
0.7246 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7041 Phase 2
0.7244 Intermediate Similarity NPD4098 Discontinued
0.7244 Intermediate Similarity NPD3094 Phase 2
0.7239 Intermediate Similarity NPD4477 Approved
0.7239 Intermediate Similarity NPD2438 Suspended
0.7239 Intermediate Similarity NPD6032 Approved
0.7239 Intermediate Similarity NPD4476 Approved
0.7236 Intermediate Similarity NPD6382 Discontinued
0.7231 Intermediate Similarity NPD5109 Approved
0.7231 Intermediate Similarity NPD5111 Phase 2
0.7231 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD5110 Phase 2
0.7231 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4659 Approved
0.7222 Intermediate Similarity NPD4749 Approved
0.7209 Intermediate Similarity NPD600 Approved
0.7209 Intermediate Similarity NPD6832 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