Structure

Physi-Chem Properties

Molecular Weight:  302.22
Volume:  344.398
LogP:  4.602
LogD:  3.927
LogS:  -4.882
# Rotatable Bonds:  1
TPSA:  29.6
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.495
Synthetic Accessibility Score:  4.795
Fsp3:  0.65
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:  -4.649
MDCK Permeability:  2.5243811251129955e-05
Pgp-inhibitor:  0.977
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.876
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.539
Plasma Protein Binding (PPB):  89.2786636352539%
Volume Distribution (VD):  1.842
Pgp-substrate:  2.549098491668701%

ADMET: Metabolism

CYP1A2-inhibitor:  0.061
CYP1A2-substrate:  0.119
CYP2C19-inhibitor:  0.394
CYP2C19-substrate:  0.386
CYP2C9-inhibitor:  0.45
CYP2C9-substrate:  0.397
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.305
CYP3A4-inhibitor:  0.557
CYP3A4-substrate:  0.261

ADMET: Excretion

Clearance (CL):  6.673
Half-life (T1/2):  0.715

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.926
Drug-inuced Liver Injury (DILI):  0.428
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.007
Maximum Recommended Daily Dose:  0.914
Skin Sensitization:  0.961
Carcinogencity:  0.28
Eye Corrosion:  0.984
Eye Irritation:  0.985
Respiratory Toxicity:  0.966

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

  Natural Product: NPC477449

Natural Product ID:  NPC477449
Common Name*:   leptodienone B
IUPAC Name:   (1R,4E,8E,12R,14R)-1,5,9-trimethyl-12-prop-1-en-2-yl-15-oxabicyclo[12.1.0]pentadeca-4,8-dien-3-one
Synonyms:  
Standard InCHIKey:  UCOLQSNNKIYDRU-QCUFSLSGSA-N
Standard InCHI:  InChI=1S/C20H30O2/c1-14(2)17-10-9-15(3)7-6-8-16(4)11-18(21)13-20(5)19(12-17)22-20/h7,11,17,19H,1,6,8-10,12-13H2,2-5H3/b15-7+,16-11+/t17-,19-,20-/m1/s1
SMILES:  C/C/1=C\CC/C(=C/C(=O)C[C@@]2([C@H](O2)C[C@@H](CC1)C(=C)C)C)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   25110933
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
NPO33583 Leptogorgia laxa Species Gorgoniidae Eukaryota n.a. Bay of Ohuira (Gulf of California, Mexico) n.a. PMID[18698819]

☑ 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
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 = 6300 nM PMID[18698819]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 10900 nM PMID[18698819]
NPT81 Cell Line A549 Homo sapiens GI50 = 5600 nM PMID[18698819]

☑ 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 NPC477449 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 NPC477448
0.8592 High Similarity NPC167049
0.8592 High Similarity NPC469691
0.8551 High Similarity NPC261398
0.8472 Intermediate Similarity NPC469669
0.8472 Intermediate Similarity NPC475771
0.8472 Intermediate Similarity NPC469678
0.8289 Intermediate Similarity NPC286229
0.8267 Intermediate Similarity NPC471740
0.8194 Intermediate Similarity NPC107783
0.8194 Intermediate Similarity NPC92909
0.8169 Intermediate Similarity NPC475310
0.8108 Intermediate Similarity NPC226242
0.8026 Intermediate Similarity NPC622
0.8026 Intermediate Similarity NPC276647
0.7975 Intermediate Similarity NPC475796
0.7895 Intermediate Similarity NPC474056
0.7875 Intermediate Similarity NPC96621
0.7867 Intermediate Similarity NPC271070
0.7848 Intermediate Similarity NPC475989
0.7805 Intermediate Similarity NPC476707
0.7805 Intermediate Similarity NPC476706
0.7794 Intermediate Similarity NPC294304
0.7794 Intermediate Similarity NPC228574
0.7792 Intermediate Similarity NPC617
0.7778 Intermediate Similarity NPC296522
0.7778 Intermediate Similarity NPC144511
0.7733 Intermediate Similarity NPC475861
0.7722 Intermediate Similarity NPC145963
0.7722 Intermediate Similarity NPC85772
0.7714 Intermediate Similarity NPC474304
0.7714 Intermediate Similarity NPC474329
0.7692 Intermediate Similarity NPC223604
0.7692 Intermediate Similarity NPC472948
0.7683 Intermediate Similarity NPC471739
0.7662 Intermediate Similarity NPC128276
0.7662 Intermediate Similarity NPC207186
0.7632 Intermediate Similarity NPC472967
0.7632 Intermediate Similarity NPC266119
0.7632 Intermediate Similarity NPC266159
0.7625 Intermediate Similarity NPC108045
0.7625 Intermediate Similarity NPC475622
0.76 Intermediate Similarity NPC474551
0.7595 Intermediate Similarity NPC141810
0.7595 Intermediate Similarity NPC79277
0.7595 Intermediate Similarity NPC475481
0.7564 Intermediate Similarity NPC476177
0.7561 Intermediate Similarity NPC38576
0.7561 Intermediate Similarity NPC279859
0.7532 Intermediate Similarity NPC57744
0.7532 Intermediate Similarity NPC476264
0.7532 Intermediate Similarity NPC15975
0.7532 Intermediate Similarity NPC195785
0.7532 Intermediate Similarity NPC476325
0.7529 Intermediate Similarity NPC476705
0.75 Intermediate Similarity NPC193351
0.75 Intermediate Similarity NPC226669
0.75 Intermediate Similarity NPC138408
0.75 Intermediate Similarity NPC155587
0.747 Intermediate Similarity NPC471738
0.747 Intermediate Similarity NPC72513
0.7468 Intermediate Similarity NPC223904
0.7467 Intermediate Similarity NPC472018
0.7467 Intermediate Similarity NPC275098
0.7467 Intermediate Similarity NPC238425
0.7467 Intermediate Similarity NPC472956
0.7467 Intermediate Similarity NPC167145
0.7467 Intermediate Similarity NPC474543
0.7439 Intermediate Similarity NPC261380
0.7439 Intermediate Similarity NPC125290
0.7436 Intermediate Similarity NPC474341
0.7432 Intermediate Similarity NPC69462
0.7432 Intermediate Similarity NPC472955
0.7407 Intermediate Similarity NPC318468
0.7407 Intermediate Similarity NPC53867
0.7407 Intermediate Similarity NPC475947
0.7407 Intermediate Similarity NPC272814
0.7407 Intermediate Similarity NPC170377
0.7403 Intermediate Similarity NPC471726
0.7403 Intermediate Similarity NPC472959
0.7403 Intermediate Similarity NPC474447
0.7403 Intermediate Similarity NPC474527
0.7397 Intermediate Similarity NPC276290
0.7381 Intermediate Similarity NPC475902
0.7381 Intermediate Similarity NPC476708
0.7375 Intermediate Similarity NPC471325
0.7375 Intermediate Similarity NPC255580
0.7375 Intermediate Similarity NPC39411
0.7368 Intermediate Similarity NPC476355
0.7368 Intermediate Similarity NPC330016
0.7349 Intermediate Similarity NPC261253
0.7349 Intermediate Similarity NPC474045
0.7342 Intermediate Similarity NPC63649
0.7342 Intermediate Similarity NPC264227
0.7342 Intermediate Similarity NPC469690
0.7342 Intermediate Similarity NPC469608
0.7342 Intermediate Similarity NPC472965
0.7342 Intermediate Similarity NPC136033
0.7342 Intermediate Similarity NPC178277
0.7333 Intermediate Similarity NPC163003
0.7326 Intermediate Similarity NPC20713
0.7317 Intermediate Similarity NPC90446
0.7317 Intermediate Similarity NPC120726
0.7317 Intermediate Similarity NPC32565
0.7308 Intermediate Similarity NPC474760
0.7308 Intermediate Similarity NPC187568
0.7308 Intermediate Similarity NPC476794
0.7308 Intermediate Similarity NPC41780
0.7308 Intermediate Similarity NPC65603
0.7308 Intermediate Similarity NPC470240
0.7297 Intermediate Similarity NPC199557
0.7297 Intermediate Similarity NPC107130
0.7297 Intermediate Similarity NPC469914
0.7284 Intermediate Similarity NPC173609
0.7273 Intermediate Similarity NPC255060
0.7273 Intermediate Similarity NPC324762
0.7273 Intermediate Similarity NPC474011
0.7273 Intermediate Similarity NPC474419
0.7273 Intermediate Similarity NPC244166
0.7262 Intermediate Similarity NPC38885
0.7262 Intermediate Similarity NPC475703
0.725 Intermediate Similarity NPC302426
0.725 Intermediate Similarity NPC474510
0.725 Intermediate Similarity NPC304795
0.7237 Intermediate Similarity NPC470237
0.7229 Intermediate Similarity NPC21471
0.7229 Intermediate Similarity NPC474547
0.7229 Intermediate Similarity NPC33570
0.7215 Intermediate Similarity NPC471220
0.7215 Intermediate Similarity NPC478247
0.7215 Intermediate Similarity NPC11796
0.7215 Intermediate Similarity NPC478122
0.7215 Intermediate Similarity NPC218817
0.7215 Intermediate Similarity NPC478246
0.7215 Intermediate Similarity NPC299235
0.7215 Intermediate Similarity NPC253749
0.7209 Intermediate Similarity NPC477684
0.7209 Intermediate Similarity NPC469464
0.7195 Intermediate Similarity NPC215294
0.7191 Intermediate Similarity NPC476275
0.7183 Intermediate Similarity NPC217940
0.7179 Intermediate Similarity NPC469646
0.7179 Intermediate Similarity NPC239127
0.7179 Intermediate Similarity NPC123360
0.7179 Intermediate Similarity NPC235906
0.7176 Intermediate Similarity NPC469653
0.7176 Intermediate Similarity NPC469628
0.7176 Intermediate Similarity NPC475906
0.7176 Intermediate Similarity NPC469631
0.7176 Intermediate Similarity NPC471047
0.7164 Intermediate Similarity NPC275472
0.7162 Intermediate Similarity NPC469688
0.716 Intermediate Similarity NPC474353
0.716 Intermediate Similarity NPC42470
0.716 Intermediate Similarity NPC301477
0.716 Intermediate Similarity NPC207188
0.716 Intermediate Similarity NPC25684
0.716 Intermediate Similarity NPC475665
0.716 Intermediate Similarity NPC281949
0.7159 Intermediate Similarity NPC140543
0.7159 Intermediate Similarity NPC476267
0.7143 Intermediate Similarity NPC469641
0.7143 Intermediate Similarity NPC70422
0.7143 Intermediate Similarity NPC259599
0.7143 Intermediate Similarity NPC70555
0.7143 Intermediate Similarity NPC469483
0.7143 Intermediate Similarity NPC143857
0.7143 Intermediate Similarity NPC104961
0.7143 Intermediate Similarity NPC472966
0.7143 Intermediate Similarity NPC261721
0.7143 Intermediate Similarity NPC229252
0.7143 Intermediate Similarity NPC140287
0.7143 Intermediate Similarity NPC117746
0.7143 Intermediate Similarity NPC50637
0.7143 Intermediate Similarity NPC469643
0.7143 Intermediate Similarity NPC122502
0.7143 Intermediate Similarity NPC469676
0.7143 Intermediate Similarity NPC15499
0.7143 Intermediate Similarity NPC294434
0.7143 Intermediate Similarity NPC144995
0.7143 Intermediate Similarity NPC227814
0.7125 Intermediate Similarity NPC308545
0.7125 Intermediate Similarity NPC254996
0.7125 Intermediate Similarity NPC270126
0.7125 Intermediate Similarity NPC82488
0.7125 Intermediate Similarity NPC268502
0.7125 Intermediate Similarity NPC469620
0.7125 Intermediate Similarity NPC113363
0.7125 Intermediate Similarity NPC80999
0.7123 Intermediate Similarity NPC197089
0.7121 Intermediate Similarity NPC474141
0.7108 Intermediate Similarity NPC115786
0.7108 Intermediate Similarity NPC72464
0.7105 Intermediate Similarity NPC129665
0.7093 Intermediate Similarity NPC475971
0.7093 Intermediate Similarity NPC166919
0.7089 Intermediate Similarity NPC471061
0.7089 Intermediate Similarity NPC180290
0.7089 Intermediate Similarity NPC122847
0.7073 Intermediate Similarity NPC474291

  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 NPC477449 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
0.7465 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD7331 Phase 2
0.716 Intermediate Similarity NPD5369 Approved
0.7024 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.6986 Remote Similarity NPD7341 Phase 2
0.6966 Remote Similarity NPD5282 Discontinued
0.6867 Remote Similarity NPD5209 Approved
0.6824 Remote Similarity NPD5363 Approved
0.6744 Remote Similarity NPD7146 Approved
0.6744 Remote Similarity NPD7521 Approved
0.6744 Remote Similarity NPD7334 Approved
0.6744 Remote Similarity NPD6409 Approved
0.6744 Remote Similarity NPD6684 Approved
0.6744 Remote Similarity NPD5330 Approved
0.6705 Remote Similarity NPD1695 Approved
0.6667 Remote Similarity NPD4270 Approved
0.6667 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4269 Approved
0.6629 Remote Similarity NPD5785 Approved
0.6629 Remote Similarity NPD6698 Approved
0.6629 Remote Similarity NPD46 Approved
0.6628 Remote Similarity NPD1694 Approved
0.6591 Remote Similarity NPD6903 Approved
0.6591 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6552 Remote Similarity NPD3618 Phase 1
0.6552 Remote Similarity NPD5786 Approved
0.6522 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6512 Remote Similarity NPD3666 Approved
0.6512 Remote Similarity NPD3665 Phase 1
0.6512 Remote Similarity NPD3133 Approved
0.6471 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6435 Approved
0.6429 Remote Similarity NPD4252 Approved
0.642 Remote Similarity NPD8039 Approved
0.6413 Remote Similarity NPD7900 Approved
0.6413 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6404 Remote Similarity NPD5737 Approved
0.6404 Remote Similarity NPD6672 Approved
0.6395 Remote Similarity NPD7154 Phase 3
0.6364 Remote Similarity NPD5279 Phase 3
0.6364 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6344 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6333 Remote Similarity NPD6101 Approved
0.6333 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6292 Remote Similarity NPD3573 Approved
0.6279 Remote Similarity NPD3667 Approved
0.6279 Remote Similarity NPD4223 Phase 3
0.6279 Remote Similarity NPD4221 Approved
0.6279 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6267 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6264 Remote Similarity NPD5207 Approved
0.6263 Remote Similarity NPD6008 Approved
0.6237 Remote Similarity NPD7748 Approved
0.6237 Remote Similarity NPD6001 Approved
0.6235 Remote Similarity NPD5368 Approved
0.6235 Remote Similarity NPD4695 Discontinued
0.6234 Remote Similarity NPD3704 Approved
0.6222 Remote Similarity NPD5208 Approved
0.6211 Remote Similarity NPD7902 Approved
0.6207 Remote Similarity NPD5362 Discontinued
0.6203 Remote Similarity NPD4137 Phase 3
0.6196 Remote Similarity NPD7983 Approved
0.6196 Remote Similarity NPD6411 Approved
0.619 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6176 Remote Similarity NPD6371 Approved
0.617 Remote Similarity NPD5695 Phase 3
0.6154 Remote Similarity NPD6673 Approved
0.6154 Remote Similarity NPD5328 Approved
0.6154 Remote Similarity NPD6904 Approved
0.6154 Remote Similarity NPD4753 Phase 2
0.6154 Remote Similarity NPD6080 Approved
0.6146 Remote Similarity NPD5696 Approved
0.6136 Remote Similarity NPD3668 Phase 3
0.6136 Remote Similarity NPD4197 Approved
0.6136 Remote Similarity NPD4786 Approved
0.6129 Remote Similarity NPD4202 Approved
0.6129 Remote Similarity NPD5778 Approved
0.6129 Remote Similarity NPD6399 Phase 3
0.6129 Remote Similarity NPD5779 Approved
0.6125 Remote Similarity NPD4691 Approved
0.6125 Remote Similarity NPD4747 Approved
0.6087 Remote Similarity NPD28 Approved
0.6087 Remote Similarity NPD5692 Phase 3
0.6087 Remote Similarity NPD29 Approved
0.6067 Remote Similarity NPD5329 Approved
0.6049 Remote Similarity NPD5276 Approved
0.6047 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6042 Remote Similarity NPD6083 Phase 2
0.6042 Remote Similarity NPD6084 Phase 2
0.604 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6022 Remote Similarity NPD6050 Approved
0.6022 Remote Similarity NPD6079 Approved
0.6022 Remote Similarity NPD5693 Phase 1
0.6022 Remote Similarity NPD7515 Phase 2
0.6022 Remote Similarity NPD5694 Approved
0.6 Remote Similarity NPD5210 Approved
0.6 Remote Similarity NPD4519 Discontinued
0.6 Remote Similarity NPD4138 Approved
0.6 Remote Similarity NPD6098 Approved
0.6 Remote Similarity NPD4694 Approved
0.6 Remote Similarity NPD4688 Approved
0.6 Remote Similarity NPD4629 Approved
0.6 Remote Similarity NPD5205 Approved
0.6 Remote Similarity NPD5280 Approved
0.6 Remote Similarity NPD4693 Phase 3
0.6 Remote Similarity NPD4690 Approved
0.6 Remote Similarity NPD4623 Approved
0.6 Remote Similarity NPD6422 Discontinued
0.6 Remote Similarity NPD4689 Approved
0.6 Remote Similarity NPD5690 Phase 2
0.5981 Remote Similarity NPD7115 Discovery
0.5978 Remote Similarity NPD5370 Suspended
0.5974 Remote Similarity NPD3197 Phase 1
0.5972 Remote Similarity NPD4627 Clinical (unspecified phase)
0.5946 Remote Similarity NPD287 Approved
0.5938 Remote Similarity NPD4697 Phase 3
0.5938 Remote Similarity NPD7839 Suspended
0.5915 Remote Similarity NPD3172 Approved
0.5914 Remote Similarity NPD7838 Discovery
0.5904 Remote Similarity NPD4687 Approved
0.5904 Remote Similarity NPD5733 Approved
0.5904 Remote Similarity NPD4058 Approved
0.5889 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5882 Remote Similarity NPD4756 Discovery
0.5876 Remote Similarity NPD4755 Approved
0.587 Remote Similarity NPD4518 Approved
0.5862 Remote Similarity NPD4820 Approved
0.5862 Remote Similarity NPD4821 Approved
0.5862 Remote Similarity NPD4819 Approved
0.5862 Remote Similarity NPD4822 Approved
0.5862 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5851 Remote Similarity NPD5284 Approved
0.5851 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5851 Remote Similarity NPD5281 Approved
0.5843 Remote Similarity NPD6110 Phase 1
0.5833 Remote Similarity NPD4266 Approved
0.5833 Remote Similarity NPD3196 Approved
0.5833 Remote Similarity NPD3194 Approved
0.5833 Remote Similarity NPD3195 Phase 2
0.5816 Remote Similarity NPD4225 Approved
0.5814 Remote Similarity NPD3617 Approved
0.5814 Remote Similarity NPD3732 Approved
0.5784 Remote Similarity NPD6402 Approved
0.5784 Remote Similarity NPD6675 Approved
0.5784 Remote Similarity NPD7128 Approved
0.5784 Remote Similarity NPD5739 Approved
0.5773 Remote Similarity NPD5221 Approved
0.5773 Remote Similarity NPD5222 Approved
0.5773 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5769 Remote Similarity NPD6373 Approved
0.5769 Remote Similarity NPD6372 Approved
0.5765 Remote Similarity NPD818 Approved
0.5765 Remote Similarity NPD819 Approved
0.5758 Remote Similarity NPD4700 Approved
0.5758 Remote Similarity NPD4696 Approved
0.5758 Remote Similarity NPD5285 Approved
0.5758 Remote Similarity NPD5286 Approved
0.5745 Remote Similarity NPD4096 Approved
0.5728 Remote Similarity NPD5697 Approved
0.5728 Remote Similarity NPD5701 Approved
0.5714 Remote Similarity NPD1696 Phase 3
0.5714 Remote Similarity NPD368 Approved
0.5714 Remote Similarity NPD5173 Approved
0.5714 Remote Similarity NPD5959 Approved
0.57 Remote Similarity NPD5223 Approved
0.5679 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5673 Remote Similarity NPD6881 Approved
0.5673 Remote Similarity NPD7320 Approved
0.5673 Remote Similarity NPD6899 Approved
0.5673 Remote Similarity NPD6011 Approved
0.567 Remote Similarity NPD5654 Approved
0.5667 Remote Similarity NPD5331 Approved
0.5667 Remote Similarity NPD4788 Approved
0.5667 Remote Similarity NPD5332 Approved
0.566 Remote Similarity NPD6650 Approved
0.566 Remote Similarity NPD6649 Approved
0.5657 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5652 Remote Similarity NPD5343 Approved
0.5644 Remote Similarity NPD5225 Approved
0.5644 Remote Similarity NPD5224 Approved
0.5644 Remote Similarity NPD5211 Phase 2
0.5644 Remote Similarity NPD5226 Approved
0.5644 Remote Similarity NPD4633 Approved
0.5632 Remote Similarity NPD4268 Approved
0.5632 Remote Similarity NPD4271 Approved
0.5625 Remote Similarity NPD5133 Approved
0.5619 Remote Similarity NPD6014 Approved
0.5619 Remote Similarity NPD6012 Approved
0.5619 Remote Similarity NPD6013 Approved
0.5618 Remote Similarity NPD4790 Discontinued
0.5612 Remote Similarity NPD5349 Clinical (unspecified phase)
0.56 Remote Similarity NPD8779 Phase 3

  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