Structure

Physi-Chem Properties

Molecular Weight:  316.2
Volume:  350.552
LogP:  4.118
LogD:  3.565
LogS:  -4.373
# Rotatable Bonds:  2
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.474
Synthetic Accessibility Score:  4.703
Fsp3:  0.55
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.535
MDCK Permeability:  2.909245631599333e-05
Pgp-inhibitor:  0.015
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.038
30% Bioavailability (F30%):  0.263

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.303
Plasma Protein Binding (PPB):  89.1784439086914%
Volume Distribution (VD):  0.524
Pgp-substrate:  7.725088119506836%

ADMET: Metabolism

CYP1A2-inhibitor:  0.667
CYP1A2-substrate:  0.179
CYP2C19-inhibitor:  0.615
CYP2C19-substrate:  0.487
CYP2C9-inhibitor:  0.468
CYP2C9-substrate:  0.355
CYP2D6-inhibitor:  0.752
CYP2D6-substrate:  0.396
CYP3A4-inhibitor:  0.766
CYP3A4-substrate:  0.281

ADMET: Excretion

Clearance (CL):  7.299
Half-life (T1/2):  0.142

ADMET: Toxicity

hERG Blockers:  0.098
Human Hepatotoxicity (H-HT):  0.964
Drug-inuced Liver Injury (DILI):  0.283
AMES Toxicity:  0.126
Rat Oral Acute Toxicity:  0.201
Maximum Recommended Daily Dose:  0.95
Skin Sensitization:  0.928
Carcinogencity:  0.788
Eye Corrosion:  0.018
Eye Irritation:  0.172
Respiratory Toxicity:  0.95

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

  Natural Product: NPC196487

Natural Product ID:  NPC196487
Common Name*:   9-Deoxy-Isoxeniolide-A
IUPAC Name:   (4Z,4aS,7E,11aR)-4-[(E)-4-hydroxy-4-methylpent-2-enylidene]-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydro-1H-cyclonona[c]pyran-3-one
Synonyms:  
Standard InCHIKey:  PGYRSUFCGXKLPM-NRTVDCPFSA-N
Standard InCHI:  InChI=1S/C20H28O3/c1-14-7-5-8-15(2)18-13-23-19(21)17(16(18)11-10-14)9-6-12-20(3,4)22/h6-7,9,12,16,18,22H,2,5,8,10-11,13H2,1,3-4H3/b12-6+,14-7+,17-9-/t16-,18+/m1/s1
SMILES:  C/C/1=CCCC(=C)[C@@H]2COC(=O)/C(=CC=CC(C)(C)O)/[C@H]2CC1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL462887
PubChem CID:   11507961
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001244] Delta valerolactones

*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
NPO27036 Xenia blumi Species Xeniidae Eukaryota n.a. Green Island, Taiwan 2002-MAY PMID[16180809]
NPO27036 Xenia blumi Species Xeniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23536 Alsophila spinulosa Species Cyatheaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18067 Muehlenbeckia platyclada Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26130 Cordia latifolia Species Cordiaceae 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
NPT139 Cell Line HT-29 Homo sapiens ED50 = 8.7 ug ml-1 PMID[554487]
NPT168 Cell Line P388 Mus musculus ED50 > 20.0 ug ml-1 PMID[554487]

☑ 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 NPC196487 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 NPC14575
0.975 High Similarity NPC234038
0.9167 High Similarity NPC106040
0.9167 High Similarity NPC115179
0.9167 High Similarity NPC212598
0.9103 High Similarity NPC107668
0.907 High Similarity NPC476049
0.8916 High Similarity NPC474369
0.881 High Similarity NPC116575
0.8734 High Similarity NPC110461
0.8734 High Similarity NPC12740
0.8652 High Similarity NPC272050
0.8642 High Similarity NPC469617
0.859 High Similarity NPC135703
0.8588 High Similarity NPC198314
0.8519 High Similarity NPC474341
0.85 High Similarity NPC61863
0.8452 Intermediate Similarity NPC53867
0.8434 Intermediate Similarity NPC325031
0.828 Intermediate Similarity NPC475053
0.8161 Intermediate Similarity NPC122502
0.814 Intermediate Similarity NPC70424
0.814 Intermediate Similarity NPC243618
0.8118 Intermediate Similarity NPC85772
0.8095 Intermediate Similarity NPC233377
0.8072 Intermediate Similarity NPC267231
0.7955 Intermediate Similarity NPC315395
0.7955 Intermediate Similarity NPC316426
0.7952 Intermediate Similarity NPC316324
0.7931 Intermediate Similarity NPC474776
0.7907 Intermediate Similarity NPC475936
0.7865 Intermediate Similarity NPC475678
0.7857 Intermediate Similarity NPC108816
0.7857 Intermediate Similarity NPC93763
0.7841 Intermediate Similarity NPC261380
0.7816 Intermediate Similarity NPC250315
0.7816 Intermediate Similarity NPC170377
0.7816 Intermediate Similarity NPC16488
0.7791 Intermediate Similarity NPC42470
0.7789 Intermediate Similarity NPC64742
0.7778 Intermediate Similarity NPC26078
0.7778 Intermediate Similarity NPC473658
0.7766 Intermediate Similarity NPC9812
0.7765 Intermediate Similarity NPC63649
0.7765 Intermediate Similarity NPC264227
0.7765 Intermediate Similarity NPC472965
0.7755 Intermediate Similarity NPC309190
0.7753 Intermediate Similarity NPC164393
0.7738 Intermediate Similarity NPC7563
0.7738 Intermediate Similarity NPC41780
0.7738 Intermediate Similarity NPC116177
0.7738 Intermediate Similarity NPC180290
0.7738 Intermediate Similarity NPC187568
0.7738 Intermediate Similarity NPC320630
0.7727 Intermediate Similarity NPC9868
0.7727 Intermediate Similarity NPC72464
0.7717 Intermediate Similarity NPC261607
0.7717 Intermediate Similarity NPC219874
0.7717 Intermediate Similarity NPC300312
0.7717 Intermediate Similarity NPC472705
0.7717 Intermediate Similarity NPC303697
0.7717 Intermediate Similarity NPC111114
0.7717 Intermediate Similarity NPC45579
0.7711 Intermediate Similarity NPC329852
0.7711 Intermediate Similarity NPC475861
0.7701 Intermediate Similarity NPC471326
0.7701 Intermediate Similarity NPC474291
0.7701 Intermediate Similarity NPC221231
0.7692 Intermediate Similarity NPC83423
0.7692 Intermediate Similarity NPC284561
0.7692 Intermediate Similarity NPC307092
0.7692 Intermediate Similarity NPC51358
0.7674 Intermediate Similarity NPC474510
0.7667 Intermediate Similarity NPC86005
0.7667 Intermediate Similarity NPC160138
0.7667 Intermediate Similarity NPC312561
0.766 Intermediate Similarity NPC209355
0.7654 Intermediate Similarity NPC316029
0.7647 Intermediate Similarity NPC4436
0.7647 Intermediate Similarity NPC128276
0.7647 Intermediate Similarity NPC471220
0.764 Intermediate Similarity NPC474547
0.764 Intermediate Similarity NPC197903
0.764 Intermediate Similarity NPC99395
0.7629 Intermediate Similarity NPC116139
0.7629 Intermediate Similarity NPC206079
0.7614 Intermediate Similarity NPC52609
0.7614 Intermediate Similarity NPC1761
0.7609 Intermediate Similarity NPC473448
0.7609 Intermediate Similarity NPC77337
0.7604 Intermediate Similarity NPC244411
0.7595 Intermediate Similarity NPC308294
0.7595 Intermediate Similarity NPC142423
0.759 Intermediate Similarity NPC476355
0.7586 Intermediate Similarity NPC471325
0.7561 Intermediate Similarity NPC163003
0.7561 Intermediate Similarity NPC288667
0.7558 Intermediate Similarity NPC178277
0.7556 Intermediate Similarity NPC475461
0.7556 Intermediate Similarity NPC305475
0.7553 Intermediate Similarity NPC475572
0.7551 Intermediate Similarity NPC66110
0.7531 Intermediate Similarity NPC265574
0.7531 Intermediate Similarity NPC151481
0.7529 Intermediate Similarity NPC315394
0.7529 Intermediate Similarity NPC57744
0.7528 Intermediate Similarity NPC149869
0.7528 Intermediate Similarity NPC476804
0.7528 Intermediate Similarity NPC82297
0.75 Intermediate Similarity NPC228978
0.75 Intermediate Similarity NPC295312
0.75 Intermediate Similarity NPC68624
0.75 Intermediate Similarity NPC145963
0.75 Intermediate Similarity NPC118011
0.75 Intermediate Similarity NPC36668
0.75 Intermediate Similarity NPC173609
0.75 Intermediate Similarity NPC94200
0.75 Intermediate Similarity NPC244166
0.75 Intermediate Similarity NPC208094
0.7474 Intermediate Similarity NPC295347
0.7474 Intermediate Similarity NPC304886
0.7474 Intermediate Similarity NPC107476
0.7473 Intermediate Similarity NPC313658
0.7473 Intermediate Similarity NPC72513
0.7473 Intermediate Similarity NPC316138
0.7473 Intermediate Similarity NPC474765
0.7471 Intermediate Similarity NPC190008
0.7471 Intermediate Similarity NPC47747
0.7449 Intermediate Similarity NPC469851
0.7449 Intermediate Similarity NPC62670
0.7444 Intermediate Similarity NPC86316
0.7444 Intermediate Similarity NPC215364
0.7444 Intermediate Similarity NPC106416
0.7444 Intermediate Similarity NPC470177
0.7444 Intermediate Similarity NPC125290
0.7444 Intermediate Similarity NPC28887
0.7444 Intermediate Similarity NPC137033
0.7444 Intermediate Similarity NPC65661
0.7444 Intermediate Similarity NPC255307
0.7442 Intermediate Similarity NPC63445
0.7442 Intermediate Similarity NPC222210
0.7442 Intermediate Similarity NPC192006
0.7442 Intermediate Similarity NPC169095
0.7442 Intermediate Similarity NPC471465
0.7442 Intermediate Similarity NPC196653
0.7439 Intermediate Similarity NPC475310
0.7439 Intermediate Similarity NPC67183
0.7423 Intermediate Similarity NPC316598
0.7419 Intermediate Similarity NPC182136
0.7419 Intermediate Similarity NPC232426
0.7419 Intermediate Similarity NPC469372
0.7419 Intermediate Similarity NPC475855
0.7419 Intermediate Similarity NPC281942
0.7419 Intermediate Similarity NPC179394
0.7419 Intermediate Similarity NPC474761
0.7419 Intermediate Similarity NPC144133
0.7419 Intermediate Similarity NPC476004
0.7416 Intermediate Similarity NPC40746
0.7416 Intermediate Similarity NPC475842
0.7416 Intermediate Similarity NPC193198
0.7416 Intermediate Similarity NPC39588
0.7416 Intermediate Similarity NPC118423
0.7416 Intermediate Similarity NPC44261
0.7416 Intermediate Similarity NPC169575
0.7412 Intermediate Similarity NPC266159
0.7412 Intermediate Similarity NPC472967
0.7412 Intermediate Similarity NPC235906
0.7412 Intermediate Similarity NPC271070
0.7412 Intermediate Similarity NPC123360
0.7412 Intermediate Similarity NPC473223
0.7412 Intermediate Similarity NPC40353
0.7407 Intermediate Similarity NPC218477
0.7407 Intermediate Similarity NPC313444
0.7391 Intermediate Similarity NPC227379
0.7391 Intermediate Similarity NPC474471
0.7391 Intermediate Similarity NPC153805
0.7391 Intermediate Similarity NPC476805
0.7386 Intermediate Similarity NPC475481
0.7386 Intermediate Similarity NPC141810
0.7386 Intermediate Similarity NPC112868
0.7386 Intermediate Similarity NPC315731
0.7386 Intermediate Similarity NPC79277
0.7381 Intermediate Similarity NPC140287
0.7381 Intermediate Similarity NPC474758
0.7374 Intermediate Similarity NPC473596
0.7368 Intermediate Similarity NPC477129
0.7368 Intermediate Similarity NPC167219
0.7368 Intermediate Similarity NPC476415
0.7368 Intermediate Similarity NPC477130
0.7368 Intermediate Similarity NPC38830
0.7368 Intermediate Similarity NPC474338
0.7363 Intermediate Similarity NPC261721
0.7363 Intermediate Similarity NPC220478
0.7363 Intermediate Similarity NPC284902
0.7356 Intermediate Similarity NPC617
0.7356 Intermediate Similarity NPC89128
0.7356 Intermediate Similarity NPC471537
0.7356 Intermediate Similarity NPC470239
0.7356 Intermediate Similarity NPC469690
0.7356 Intermediate Similarity NPC470244

  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 NPC196487 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
0.75 Intermediate Similarity NPD8039 Approved
0.7303 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD5779 Approved
0.7263 Intermediate Similarity NPD5778 Approved
0.7245 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD5785 Approved
0.7234 Intermediate Similarity NPD46 Approved
0.7234 Intermediate Similarity NPD6698 Approved
0.7128 Intermediate Similarity NPD6101 Approved
0.7128 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD4756 Discovery
0.7111 Intermediate Similarity NPD5209 Approved
0.7065 Intermediate Similarity NPD5363 Approved
0.7065 Intermediate Similarity NPD1694 Approved
0.7041 Intermediate Similarity NPD7839 Suspended
0.7037 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD5362 Discontinued
0.7033 Intermediate Similarity NPD7154 Phase 3
0.6979 Remote Similarity NPD6411 Approved
0.6979 Remote Similarity NPD7983 Approved
0.6939 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6882 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7838 Discovery
0.6832 Remote Similarity NPD6648 Approved
0.6809 Remote Similarity NPD5786 Approved
0.6747 Remote Similarity NPD7331 Phase 2
0.6739 Remote Similarity NPD4269 Approved
0.6739 Remote Similarity NPD4270 Approved
0.6737 Remote Similarity NPD3573 Approved
0.6703 Remote Similarity NPD4820 Approved
0.6703 Remote Similarity NPD4821 Approved
0.6703 Remote Similarity NPD4822 Approved
0.6703 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6703 Remote Similarity NPD4819 Approved
0.6667 Remote Similarity NPD5784 Clinical (unspecified phase)
0.663 Remote Similarity NPD5369 Approved
0.6598 Remote Similarity NPD1695 Approved
0.6571 Remote Similarity NPD5909 Discontinued
0.6569 Remote Similarity NPD4225 Approved
0.6559 Remote Similarity NPD6435 Approved
0.6526 Remote Similarity NPD1696 Phase 3
0.6522 Remote Similarity NPD4252 Approved
0.6506 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6489 Remote Similarity NPD5332 Approved
0.6489 Remote Similarity NPD5331 Approved
0.6484 Remote Similarity NPD4271 Approved
0.6484 Remote Similarity NPD4268 Approved
0.6465 Remote Similarity NPD7637 Suspended
0.6463 Remote Similarity NPD4192 Approved
0.6463 Remote Similarity NPD4193 Approved
0.6463 Remote Similarity NPD4191 Approved
0.6463 Remote Similarity NPD4194 Approved
0.6458 Remote Similarity NPD6422 Discontinued
0.6452 Remote Similarity NPD4790 Discontinued
0.6449 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6442 Remote Similarity NPD5344 Discontinued
0.6429 Remote Similarity NPD7341 Phase 2
0.6422 Remote Similarity NPD6371 Approved
0.6389 Remote Similarity NPD6686 Approved
0.6372 Remote Similarity NPD7115 Discovery
0.6364 Remote Similarity NPD5207 Approved
0.6354 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6346 Remote Similarity NPD7639 Approved
0.6346 Remote Similarity NPD7640 Approved
0.6344 Remote Similarity NPD5368 Approved
0.6341 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5282 Discontinued
0.6321 Remote Similarity NPD6647 Phase 2
0.6306 Remote Similarity NPD6053 Discontinued
0.63 Remote Similarity NPD5693 Phase 1
0.63 Remote Similarity NPD5284 Approved
0.63 Remote Similarity NPD5694 Approved
0.63 Remote Similarity NPD5281 Approved
0.6293 Remote Similarity NPD8515 Approved
0.6293 Remote Similarity NPD8516 Approved
0.6293 Remote Similarity NPD8517 Approved
0.6293 Remote Similarity NPD8513 Phase 3
0.6289 Remote Similarity NPD6409 Approved
0.6289 Remote Similarity NPD7334 Approved
0.6289 Remote Similarity NPD6684 Approved
0.6289 Remote Similarity NPD7146 Approved
0.6289 Remote Similarity NPD7521 Approved
0.6289 Remote Similarity NPD5330 Approved
0.6289 Remote Similarity NPD4249 Approved
0.6289 Remote Similarity NPD4519 Discontinued
0.6289 Remote Similarity NPD4623 Approved
0.6279 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6275 Remote Similarity NPD5695 Phase 3
0.625 Remote Similarity NPD7638 Approved
0.625 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6224 Remote Similarity NPD4250 Approved
0.6224 Remote Similarity NPD4251 Approved
0.6216 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6216 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6216 Remote Similarity NPD2181 Clinical (unspecified phase)
0.62 Remote Similarity NPD5692 Phase 3
0.6176 Remote Similarity NPD7748 Approved
0.617 Remote Similarity NPD4695 Discontinued
0.6163 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6162 Remote Similarity NPD6672 Approved
0.6162 Remote Similarity NPD4518 Approved
0.6162 Remote Similarity NPD5737 Approved
0.6162 Remote Similarity NPD6903 Approved
0.6162 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6083 Phase 2
0.6154 Remote Similarity NPD6084 Phase 2
0.6147 Remote Similarity NPD5697 Approved
0.6139 Remote Similarity NPD6050 Approved
0.6122 Remote Similarity NPD5279 Phase 3
0.61 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6095 Remote Similarity NPD5696 Approved
0.6091 Remote Similarity NPD6881 Approved
0.6091 Remote Similarity NPD6011 Approved
0.6091 Remote Similarity NPD6899 Approved
0.6078 Remote Similarity NPD6399 Phase 3
0.6076 Remote Similarity NPD3172 Approved
0.605 Remote Similarity NPD7830 Approved
0.605 Remote Similarity NPD7829 Approved
0.604 Remote Similarity NPD3673 Approved
0.604 Remote Similarity NPD3672 Approved
0.6038 Remote Similarity NPD6404 Discontinued
0.6038 Remote Similarity NPD2066 Phase 3
0.6036 Remote Similarity NPD6012 Approved
0.6036 Remote Similarity NPD6014 Approved
0.6036 Remote Similarity NPD2182 Approved
0.6036 Remote Similarity NPD6013 Approved
0.6033 Remote Similarity NPD8074 Phase 3
0.6019 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6 Remote Similarity NPD3194 Approved
0.6 Remote Similarity NPD7902 Approved
0.6 Remote Similarity NPD3196 Approved
0.6 Remote Similarity NPD3195 Phase 2
0.6 Remote Similarity NPD5208 Approved
0.6 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6 Remote Similarity NPD690 Clinical (unspecified phase)
0.6 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6 Remote Similarity NPD4266 Approved
0.5982 Remote Similarity NPD7102 Approved
0.5982 Remote Similarity NPD7290 Approved
0.5982 Remote Similarity NPD6883 Approved
0.5982 Remote Similarity NPD2067 Discontinued
0.598 Remote Similarity NPD4810 Clinical (unspecified phase)
0.598 Remote Similarity NPD6079 Approved
0.598 Remote Similarity NPD7515 Phase 2
0.5978 Remote Similarity NPD8264 Approved
0.5968 Remote Similarity NPD7260 Phase 2
0.596 Remote Similarity NPD5280 Approved
0.596 Remote Similarity NPD4694 Approved
0.596 Remote Similarity NPD5690 Phase 2
0.5957 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5948 Remote Similarity NPD7500 Approved
0.5941 Remote Similarity NPD6904 Approved
0.5941 Remote Similarity NPD6080 Approved
0.5941 Remote Similarity NPD6673 Approved
0.5941 Remote Similarity NPD5370 Suspended
0.593 Remote Similarity NPD3197 Phase 1
0.5929 Remote Similarity NPD6617 Approved
0.5929 Remote Similarity NPD6847 Approved
0.5929 Remote Similarity NPD8130 Phase 1
0.5929 Remote Similarity NPD6649 Approved
0.5929 Remote Similarity NPD6869 Approved
0.5929 Remote Similarity NPD6650 Approved
0.5926 Remote Similarity NPD5211 Phase 2
0.5918 Remote Similarity NPD3665 Phase 1
0.5918 Remote Similarity NPD3666 Approved
0.5918 Remote Similarity NPD3133 Approved
0.5909 Remote Similarity NPD5739 Approved
0.5909 Remote Similarity NPD7128 Approved
0.5909 Remote Similarity NPD6402 Approved
0.5909 Remote Similarity NPD6675 Approved
0.5897 Remote Similarity NPD7641 Discontinued
0.5882 Remote Similarity NPD368 Approved
0.5882 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5877 Remote Similarity NPD8297 Approved
0.5877 Remote Similarity NPD6882 Approved
0.5876 Remote Similarity NPD3667 Approved
0.5876 Remote Similarity NPD4223 Phase 3
0.5876 Remote Similarity NPD4221 Approved
0.587 Remote Similarity NPD4058 Approved
0.5865 Remote Similarity NPD7900 Approved
0.5865 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5856 Remote Similarity NPD5701 Approved
0.5833 Remote Similarity NPD7514 Phase 3
0.5833 Remote Similarity NPD7332 Phase 2
0.5823 Remote Similarity NPD28 Approved
0.5823 Remote Similarity NPD6927 Phase 3
0.5823 Remote Similarity NPD29 Approved
0.582 Remote Similarity NPD8273 Phase 1
0.582 Remote Similarity NPD6637 Approved
0.5818 Remote Similarity NPD5141 Approved
0.5816 Remote Similarity NPD6110 Phase 1
0.5816 Remote Similarity NPD6695 Phase 3
0.581 Remote Similarity NPD5654 Approved
0.581 Remote Similarity NPD6356 Clinical (unspecified phase)
0.581 Remote Similarity NPD4629 Approved
0.581 Remote Similarity NPD5210 Approved
0.5804 Remote Similarity NPD7320 Approved
0.58 Remote Similarity NPD3618 Phase 1
0.58 Remote Similarity NPD6098 Approved
0.5795 Remote Similarity NPD3704 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