Structure

Physi-Chem Properties

Molecular Weight:  278.22
Volume:  320.999
LogP:  3.426
LogD:  3.59
LogS:  -3.788
# Rotatable Bonds:  6
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.722
Synthetic Accessibility Score:  3.533
Fsp3:  0.722
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:  -4.679
MDCK Permeability:  2.0291445252951235e-05
Pgp-inhibitor:  0.869
Pgp-substrate:  0.801
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.963
30% Bioavailability (F30%):  0.276

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.887
Plasma Protein Binding (PPB):  94.20577239990234%
Volume Distribution (VD):  1.55
Pgp-substrate:  2.7156102657318115%

ADMET: Metabolism

CYP1A2-inhibitor:  0.123
CYP1A2-substrate:  0.525
CYP2C19-inhibitor:  0.141
CYP2C19-substrate:  0.584
CYP2C9-inhibitor:  0.095
CYP2C9-substrate:  0.926
CYP2D6-inhibitor:  0.029
CYP2D6-substrate:  0.819
CYP3A4-inhibitor:  0.031
CYP3A4-substrate:  0.197

ADMET: Excretion

Clearance (CL):  9.498
Half-life (T1/2):  0.382

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.095
Drug-inuced Liver Injury (DILI):  0.026
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.039
Maximum Recommended Daily Dose:  0.95
Skin Sensitization:  0.628
Carcinogencity:  0.073
Eye Corrosion:  0.343
Eye Irritation:  0.545
Respiratory Toxicity:  0.652

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

  Natural Product: NPC96962

Natural Product ID:  NPC96962
Common Name*:   (S,E)-8-(5-Hydroxy-2,6,6-Trimethylcyclohex-1-Enyl)-6-Methyloct-5-En-2-One
IUPAC Name:   (E)-8-[(5S)-5-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-6-methyloct-5-en-2-one
Synonyms:  
Standard InCHIKey:  BOCJMIRVDOHYKS-BNXPMYBGSA-N
Standard InCHI:  InChI=1S/C18H30O2/c1-13(7-6-8-15(3)19)9-11-16-14(2)10-12-17(20)18(16,4)5/h7,17,20H,6,8-12H2,1-5H3/b13-7+/t17-/m0/s1
SMILES:  CC(=O)CC/C=C(/CCC1=C(C)CC[C@@H](C1(C)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL450502
PubChem CID:   23426351
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO15949 Cystophora moniliformis Species Sargassaceae Eukaryota n.a. southern Australian n.a. PMID[18687007]
NPO15949 Cystophora moniliformis Species Sargassaceae 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
NPT168 Cell Line P388 Mus musculus IC50 > 40000.0 nM PMID[465976]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes IZ = 1.0 mm PMID[465976]

☑ 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 NPC96962 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
0.8406 Intermediate Similarity NPC173321
0.8333 Intermediate Similarity NPC167873
0.8333 Intermediate Similarity NPC1973
0.8333 Intermediate Similarity NPC290367
0.8308 Intermediate Similarity NPC475251
0.8108 Intermediate Similarity NPC178852
0.8108 Intermediate Similarity NPC475994
0.8082 Intermediate Similarity NPC250621
0.8026 Intermediate Similarity NPC14151
0.8026 Intermediate Similarity NPC136150
0.8026 Intermediate Similarity NPC473420
0.7973 Intermediate Similarity NPC203403
0.7973 Intermediate Similarity NPC197659
0.7971 Intermediate Similarity NPC45782
0.7945 Intermediate Similarity NPC114236
0.7922 Intermediate Similarity NPC48362
0.7922 Intermediate Similarity NPC151519
0.791 Intermediate Similarity NPC83200
0.7895 Intermediate Similarity NPC74086
0.7887 Intermediate Similarity NPC92801
0.7857 Intermediate Similarity NPC208999
0.7857 Intermediate Similarity NPC45264
0.7838 Intermediate Similarity NPC470525
0.7821 Intermediate Similarity NPC105173
0.7821 Intermediate Similarity NPC278648
0.7821 Intermediate Similarity NPC476082
0.7808 Intermediate Similarity NPC477138
0.7808 Intermediate Similarity NPC243342
0.7794 Intermediate Similarity NPC225415
0.7778 Intermediate Similarity NPC242001
0.7763 Intermediate Similarity NPC281138
0.7763 Intermediate Similarity NPC308038
0.7763 Intermediate Similarity NPC470429
0.7746 Intermediate Similarity NPC10758
0.7746 Intermediate Similarity NPC250928
0.7733 Intermediate Similarity NPC74995
0.7733 Intermediate Similarity NPC283619
0.7733 Intermediate Similarity NPC470428
0.7733 Intermediate Similarity NPC325946
0.7727 Intermediate Similarity NPC278202
0.7722 Intermediate Similarity NPC180834
0.7722 Intermediate Similarity NPC59453
0.7722 Intermediate Similarity NPC472265
0.7722 Intermediate Similarity NPC221758
0.7714 Intermediate Similarity NPC114651
0.7703 Intermediate Similarity NPC477923
0.7703 Intermediate Similarity NPC291503
0.7703 Intermediate Similarity NPC66566
0.7692 Intermediate Similarity NPC212083
0.7692 Intermediate Similarity NPC93590
0.7692 Intermediate Similarity NPC73882
0.7681 Intermediate Similarity NPC287339
0.7671 Intermediate Similarity NPC186042
0.7671 Intermediate Similarity NPC471799
0.7662 Intermediate Similarity NPC2482
0.7662 Intermediate Similarity NPC157895
0.7662 Intermediate Similarity NPC172013
0.7662 Intermediate Similarity NPC148685
0.7662 Intermediate Similarity NPC471514
0.7662 Intermediate Similarity NPC104120
0.7654 Intermediate Similarity NPC73064
0.7654 Intermediate Similarity NPC298904
0.7639 Intermediate Similarity NPC145498
0.7632 Intermediate Similarity NPC476949
0.7625 Intermediate Similarity NPC133954
0.7625 Intermediate Similarity NPC15807
0.7625 Intermediate Similarity NPC202868
0.7625 Intermediate Similarity NPC470574
0.7606 Intermediate Similarity NPC96484
0.76 Intermediate Similarity NPC477925
0.76 Intermediate Similarity NPC263582
0.76 Intermediate Similarity NPC265588
0.76 Intermediate Similarity NPC274079
0.7595 Intermediate Similarity NPC251475
0.7595 Intermediate Similarity NPC64600
0.7595 Intermediate Similarity NPC169941
0.7571 Intermediate Similarity NPC137163
0.7568 Intermediate Similarity NPC471797
0.7568 Intermediate Similarity NPC215050
0.7568 Intermediate Similarity NPC91858
0.7568 Intermediate Similarity NPC78527
0.7564 Intermediate Similarity NPC6663
0.7564 Intermediate Similarity NPC121984
0.7564 Intermediate Similarity NPC142163
0.7561 Intermediate Similarity NPC471722
0.7534 Intermediate Similarity NPC164022
0.7534 Intermediate Similarity NPC469343
0.7534 Intermediate Similarity NPC84790
0.7534 Intermediate Similarity NPC477792
0.7534 Intermediate Similarity NPC167706
0.7532 Intermediate Similarity NPC152061
0.7532 Intermediate Similarity NPC229204
0.7532 Intermediate Similarity NPC100906
0.7531 Intermediate Similarity NPC202394
0.7531 Intermediate Similarity NPC475022
0.7531 Intermediate Similarity NPC474778
0.7531 Intermediate Similarity NPC222613
0.7531 Intermediate Similarity NPC474733
0.7531 Intermediate Similarity NPC472974
0.7531 Intermediate Similarity NPC475862
0.7531 Intermediate Similarity NPC474732
0.7531 Intermediate Similarity NPC183736
0.7531 Intermediate Similarity NPC94666
0.7531 Intermediate Similarity NPC51014
0.7531 Intermediate Similarity NPC472986
0.7531 Intermediate Similarity NPC472985
0.7531 Intermediate Similarity NPC213412
0.7531 Intermediate Similarity NPC31564
0.7531 Intermediate Similarity NPC20688
0.7531 Intermediate Similarity NPC118648
0.7531 Intermediate Similarity NPC74363
0.7531 Intermediate Similarity NPC473226
0.7531 Intermediate Similarity NPC145879
0.75 Intermediate Similarity NPC40687
0.75 Intermediate Similarity NPC477924
0.75 Intermediate Similarity NPC64971
0.75 Intermediate Similarity NPC33913
0.75 Intermediate Similarity NPC471798
0.75 Intermediate Similarity NPC276769
0.75 Intermediate Similarity NPC260573
0.747 Intermediate Similarity NPC119416
0.7468 Intermediate Similarity NPC310989
0.7467 Intermediate Similarity NPC313179
0.7467 Intermediate Similarity NPC171148
0.7467 Intermediate Similarity NPC474011
0.7467 Intermediate Similarity NPC474885
0.7467 Intermediate Similarity NPC69383
0.7465 Intermediate Similarity NPC106613
0.7463 Intermediate Similarity NPC122239
0.7439 Intermediate Similarity NPC472324
0.7439 Intermediate Similarity NPC477926
0.7439 Intermediate Similarity NPC475740
0.7439 Intermediate Similarity NPC58063
0.7439 Intermediate Similarity NPC109900
0.7436 Intermediate Similarity NPC472478
0.7432 Intermediate Similarity NPC68443
0.7432 Intermediate Similarity NPC49737
0.7432 Intermediate Similarity NPC261316
0.7432 Intermediate Similarity NPC182717
0.7429 Intermediate Similarity NPC474304
0.7429 Intermediate Similarity NPC474329
0.7407 Intermediate Similarity NPC179006
0.7407 Intermediate Similarity NPC36350
0.7407 Intermediate Similarity NPC79573
0.7407 Intermediate Similarity NPC474853
0.7407 Intermediate Similarity NPC476602
0.7407 Intermediate Similarity NPC32037
0.7403 Intermediate Similarity NPC297996
0.7403 Intermediate Similarity NPC474989
0.7403 Intermediate Similarity NPC476314
0.7403 Intermediate Similarity NPC99168
0.7403 Intermediate Similarity NPC62336
0.7403 Intermediate Similarity NPC22955
0.7403 Intermediate Similarity NPC470396
0.7403 Intermediate Similarity NPC275910
0.7397 Intermediate Similarity NPC34834
0.7375 Intermediate Similarity NPC312480
0.7375 Intermediate Similarity NPC470948
0.7368 Intermediate Similarity NPC321381
0.7368 Intermediate Similarity NPC96319
0.7368 Intermediate Similarity NPC321016
0.7368 Intermediate Similarity NPC469646
0.7368 Intermediate Similarity NPC107059
0.7368 Intermediate Similarity NPC253190
0.7361 Intermediate Similarity NPC117804
0.7361 Intermediate Similarity NPC471238
0.7349 Intermediate Similarity NPC473242
0.7349 Intermediate Similarity NPC17733
0.7349 Intermediate Similarity NPC474512
0.7349 Intermediate Similarity NPC328313
0.7349 Intermediate Similarity NPC472802
0.7349 Intermediate Similarity NPC181225
0.7349 Intermediate Similarity NPC473229
0.7349 Intermediate Similarity NPC158778
0.7349 Intermediate Similarity NPC206060
0.7349 Intermediate Similarity NPC470629
0.7349 Intermediate Similarity NPC328539
0.7349 Intermediate Similarity NPC290690
0.7344 Intermediate Similarity NPC217188
0.7342 Intermediate Similarity NPC159148
0.7342 Intermediate Similarity NPC116797
0.7342 Intermediate Similarity NPC470298
0.7342 Intermediate Similarity NPC3915
0.7333 Intermediate Similarity NPC100334
0.7333 Intermediate Similarity NPC306727
0.7324 Intermediate Similarity NPC326310
0.7317 Intermediate Similarity NPC82979
0.7317 Intermediate Similarity NPC155011
0.7317 Intermediate Similarity NPC235341
0.7317 Intermediate Similarity NPC72133
0.7317 Intermediate Similarity NPC95594
0.7317 Intermediate Similarity NPC329692
0.7317 Intermediate Similarity NPC325594
0.7317 Intermediate Similarity NPC73038
0.7317 Intermediate Similarity NPC470955
0.7317 Intermediate Similarity NPC477579
0.7317 Intermediate Similarity NPC6979
0.7317 Intermediate Similarity NPC94755
0.7317 Intermediate Similarity NPC158393
0.7308 Intermediate Similarity NPC291379

  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 NPC96962 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
0.7922 Intermediate Similarity NPD3667 Approved
0.7895 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD4786 Approved
0.7531 Intermediate Similarity NPD3618 Phase 1
0.7467 Intermediate Similarity NPD8264 Approved
0.7368 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD7331 Phase 2
0.7284 Intermediate Similarity NPD3665 Phase 1
0.7284 Intermediate Similarity NPD3133 Approved
0.7284 Intermediate Similarity NPD3666 Approved
0.7262 Intermediate Similarity NPD5328 Approved
0.7237 Intermediate Similarity NPD6942 Approved
0.7237 Intermediate Similarity NPD7339 Approved
0.7195 Intermediate Similarity NPD1696 Phase 3
0.7108 Intermediate Similarity NPD5279 Phase 3
0.7105 Intermediate Similarity NPD6926 Approved
0.7105 Intermediate Similarity NPD6924 Approved
0.7093 Intermediate Similarity NPD6079 Approved
0.7093 Intermediate Similarity NPD7515 Phase 2
0.7089 Intermediate Similarity NPD7645 Phase 2
0.7073 Intermediate Similarity NPD3668 Phase 3
0.7067 Intermediate Similarity NPD7150 Approved
0.7067 Intermediate Similarity NPD7151 Approved
0.7067 Intermediate Similarity NPD7152 Approved
0.7027 Intermediate Similarity NPD6922 Approved
0.7027 Intermediate Similarity NPD6923 Approved
0.7011 Intermediate Similarity NPD4202 Approved
0.7 Intermediate Similarity NPD4695 Discontinued
0.6933 Remote Similarity NPD7143 Approved
0.6933 Remote Similarity NPD7144 Approved
0.6923 Remote Similarity NPD6933 Approved
0.6897 Remote Similarity NPD6411 Approved
0.6818 Remote Similarity NPD6399 Phase 3
0.679 Remote Similarity NPD7525 Registered
0.679 Remote Similarity NPD7509 Discontinued
0.6778 Remote Similarity NPD4697 Phase 3
0.6778 Remote Similarity NPD5222 Approved
0.6778 Remote Similarity NPD5221 Approved
0.6778 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6765 Remote Similarity NPD4219 Approved
0.6761 Remote Similarity NPD368 Approved
0.675 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6742 Remote Similarity NPD7748 Approved
0.6712 Remote Similarity NPD7341 Phase 2
0.6703 Remote Similarity NPD4755 Approved
0.6703 Remote Similarity NPD5173 Approved
0.6667 Remote Similarity NPD6101 Approved
0.6667 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4753 Phase 2
0.6667 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6929 Approved
0.6627 Remote Similarity NPD4223 Phase 3
0.6627 Remote Similarity NPD4221 Approved
0.6625 Remote Similarity NPD6932 Approved
0.6625 Remote Similarity NPD6925 Approved
0.6625 Remote Similarity NPD5776 Phase 2
0.6622 Remote Similarity NPD3704 Approved
0.6618 Remote Similarity NPD342 Phase 1
0.6585 Remote Similarity NPD6931 Approved
0.6585 Remote Similarity NPD6930 Phase 2
0.6585 Remote Similarity NPD4748 Discontinued
0.6582 Remote Similarity NPD8039 Approved
0.6559 Remote Similarity NPD4700 Approved
0.6559 Remote Similarity NPD4696 Approved
0.6559 Remote Similarity NPD5285 Approved
0.6559 Remote Similarity NPD5286 Approved
0.6543 Remote Similarity NPD7145 Approved
0.6543 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7902 Approved
0.6506 Remote Similarity NPD5369 Approved
0.6489 Remote Similarity NPD5223 Approved
0.6471 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4197 Approved
0.6463 Remote Similarity NPD6683 Phase 2
0.6463 Remote Similarity NPD4195 Approved
0.6452 Remote Similarity NPD4225 Approved
0.6444 Remote Similarity NPD5778 Approved
0.6444 Remote Similarity NPD5779 Approved
0.6437 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4270 Approved
0.6429 Remote Similarity NPD4269 Approved
0.6421 Remote Similarity NPD5226 Approved
0.6421 Remote Similarity NPD5211 Phase 2
0.6421 Remote Similarity NPD4633 Approved
0.6421 Remote Similarity NPD5224 Approved
0.6421 Remote Similarity NPD5225 Approved
0.6395 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6395 Remote Similarity NPD5329 Approved
0.6386 Remote Similarity NPD5368 Approved
0.6386 Remote Similarity NPD4821 Approved
0.6386 Remote Similarity NPD7332 Phase 2
0.6386 Remote Similarity NPD4820 Approved
0.6386 Remote Similarity NPD4819 Approved
0.6386 Remote Similarity NPD4822 Approved
0.6386 Remote Similarity NPD7514 Phase 3
0.6364 Remote Similarity NPD4518 Approved
0.6364 Remote Similarity NPD15 Approved
0.6364 Remote Similarity NPD791 Approved
0.6354 Remote Similarity NPD4754 Approved
0.6354 Remote Similarity NPD5174 Approved
0.6354 Remote Similarity NPD5175 Approved
0.6353 Remote Similarity NPD7154 Phase 3
0.6353 Remote Similarity NPD5362 Discontinued
0.6353 Remote Similarity NPD6695 Phase 3
0.6353 Remote Similarity NPD5332 Approved
0.6353 Remote Similarity NPD5331 Approved
0.6351 Remote Similarity NPD3197 Phase 1
0.6341 Remote Similarity NPD4268 Approved
0.6341 Remote Similarity NPD4271 Approved
0.6341 Remote Similarity NPD3617 Approved
0.6333 Remote Similarity NPD7637 Suspended
0.6329 Remote Similarity NPD4732 Discontinued
0.6322 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6322 Remote Similarity NPD7521 Approved
0.6322 Remote Similarity NPD5690 Phase 2
0.6322 Remote Similarity NPD5330 Approved
0.6322 Remote Similarity NPD4694 Approved
0.6322 Remote Similarity NPD4689 Approved
0.6322 Remote Similarity NPD5205 Approved
0.6322 Remote Similarity NPD4519 Discontinued
0.6322 Remote Similarity NPD7334 Approved
0.6322 Remote Similarity NPD4623 Approved
0.6322 Remote Similarity NPD7146 Approved
0.6322 Remote Similarity NPD6684 Approved
0.6322 Remote Similarity NPD5280 Approved
0.6322 Remote Similarity NPD6409 Approved
0.6322 Remote Similarity NPD4690 Approved
0.6322 Remote Similarity NPD4688 Approved
0.6322 Remote Similarity NPD4693 Phase 3
0.6322 Remote Similarity NPD4138 Approved
0.631 Remote Similarity NPD6902 Approved
0.631 Remote Similarity NPD6898 Phase 1
0.631 Remote Similarity NPD4790 Discontinued
0.6304 Remote Similarity NPD4629 Approved
0.6304 Remote Similarity NPD5210 Approved
0.6301 Remote Similarity NPD4194 Approved
0.6301 Remote Similarity NPD4191 Approved
0.6301 Remote Similarity NPD4192 Approved
0.6301 Remote Similarity NPD4193 Approved
0.6289 Remote Similarity NPD5141 Approved
0.6279 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6277 Remote Similarity NPD7638 Approved
0.6277 Remote Similarity NPD5290 Discontinued
0.625 Remote Similarity NPD4784 Approved
0.625 Remote Similarity NPD4785 Approved
0.6235 Remote Similarity NPD6435 Approved
0.6224 Remote Similarity NPD6675 Approved
0.6224 Remote Similarity NPD4768 Approved
0.6224 Remote Similarity NPD4767 Approved
0.6224 Remote Similarity NPD5739 Approved
0.6224 Remote Similarity NPD6402 Approved
0.6224 Remote Similarity NPD7128 Approved
0.6222 Remote Similarity NPD5785 Approved
0.6211 Remote Similarity NPD7639 Approved
0.6211 Remote Similarity NPD7640 Approved
0.6207 Remote Similarity NPD6893 Approved
0.6207 Remote Similarity NPD5363 Approved
0.6203 Remote Similarity NPD4243 Approved
0.6196 Remote Similarity NPD5282 Discontinued
0.6196 Remote Similarity NPD7900 Approved
0.6196 Remote Similarity NPD7901 Clinical (unspecified phase)
0.619 Remote Similarity NPD5790 Clinical (unspecified phase)
0.619 Remote Similarity NPD4252 Approved
0.6184 Remote Similarity NPD6108 Clinical (unspecified phase)
0.618 Remote Similarity NPD6903 Approved
0.618 Remote Similarity NPD7513 Clinical (unspecified phase)
0.617 Remote Similarity NPD6083 Phase 2
0.617 Remote Similarity NPD6084 Phase 2
0.6164 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6163 Remote Similarity NPD4788 Approved
0.6162 Remote Similarity NPD5701 Approved
0.6162 Remote Similarity NPD5697 Approved
0.6154 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6154 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4137 Phase 3
0.6154 Remote Similarity NPD1082 Approved
0.6143 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6136 Remote Similarity NPD5786 Approved
0.6133 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6129 Remote Similarity NPD5695 Phase 3
0.6118 Remote Similarity NPD4692 Approved
0.6118 Remote Similarity NPD4139 Approved
0.6111 Remote Similarity NPD287 Approved
0.6111 Remote Similarity NPD7285 Clinical (unspecified phase)
0.61 Remote Similarity NPD4730 Approved
0.61 Remote Similarity NPD5168 Approved
0.61 Remote Similarity NPD4729 Approved
0.61 Remote Similarity NPD6011 Approved
0.61 Remote Similarity NPD6881 Approved
0.61 Remote Similarity NPD5128 Approved
0.61 Remote Similarity NPD6899 Approved
0.61 Remote Similarity NPD7320 Approved
0.6087 Remote Similarity NPD3172 Approved
0.6076 Remote Similarity NPD4747 Approved
0.6076 Remote Similarity NPD4691 Approved
0.6067 Remote Similarity NPD7524 Approved
0.6067 Remote Similarity NPD7750 Discontinued
0.6067 Remote Similarity NPD3573 Approved
0.6053 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6044 Remote Similarity NPD4096 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