Structure

Physi-Chem Properties

Molecular Weight:  278.19
Volume:  298.017
LogP:  3.616
LogD:  3.585
LogS:  -4.244
# Rotatable Bonds:  2
TPSA:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.728
Synthetic Accessibility Score:  4.885
Fsp3:  0.824
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:  -4.586
MDCK Permeability:  2.1257994376355782e-05
Pgp-inhibitor:  0.948
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.105
30% Bioavailability (F30%):  0.723

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.834
Plasma Protein Binding (PPB):  76.0216293334961%
Volume Distribution (VD):  1.26
Pgp-substrate:  15.303732872009277%

ADMET: Metabolism

CYP1A2-inhibitor:  0.209
CYP1A2-substrate:  0.943
CYP2C19-inhibitor:  0.138
CYP2C19-substrate:  0.903
CYP2C9-inhibitor:  0.066
CYP2C9-substrate:  0.008
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.117
CYP3A4-inhibitor:  0.53
CYP3A4-substrate:  0.533

ADMET: Excretion

Clearance (CL):  14.778
Half-life (T1/2):  0.587

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.393
Drug-inuced Liver Injury (DILI):  0.39
AMES Toxicity:  0.418
Rat Oral Acute Toxicity:  0.321
Maximum Recommended Daily Dose:  0.759
Skin Sensitization:  0.867
Carcinogencity:  0.782
Eye Corrosion:  0.445
Eye Irritation:  0.948
Respiratory Toxicity:  0.961

Download Data

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

  Natural Product: NPC469569

Natural Product ID:  NPC469569
Common Name*:   Oblongolide Y
IUPAC Name:   1-[(1S,3aS,5aR,7S,9aS,9bR)-1-methoxy-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydrobenzo[g][2]benzofuran-1-yl]ethanone
Synonyms:   Oblongolide Y
Standard InCHIKey:  WPHPTEHUVDWFIT-MNMQIZOCSA-N
Standard InCHI:  InChI=1S/C17H26O3/c1-11-5-8-15-13(9-11)6-7-14-10-20-17(19-4,12(2)18)16(14,15)3/h6-7,11,13-15H,5,8-10H2,1-4H3/t11-,13-,14+,15-,16-,17+/m0/s1
SMILES:  CC1CCC2C(C1)C=CC3C2(C(OC3)(C(=O)C)OC)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1087677
PubChem CID:   44627608
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO33230 Phomopsis sp. BCC 9789 Species Valsaceae Eukaryota n.a. n.a. n.a. PMID[20038128]

☑ 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
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 180000.0 nM PMID[466555]
NPT91 Cell Line KB Homo sapiens IC50 > 72000.0 nM PMID[466555]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 > 72000.0 nM PMID[466555]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 48000.0 nM PMID[466555]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC > 180000.0 nM PMID[466555]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 MIC > 180000.0 nM PMID[466555]

☑ 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 NPC469569 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
0.8488 Intermediate Similarity NPC230016
0.8272 Intermediate Similarity NPC41017
0.8256 Intermediate Similarity NPC300985
0.8 Intermediate Similarity NPC149237
0.7889 Intermediate Similarity NPC174765
0.7857 Intermediate Similarity NPC35574
0.7849 Intermediate Similarity NPC248574
0.7841 Intermediate Similarity NPC133652
0.7812 Intermediate Similarity NPC473384
0.7791 Intermediate Similarity NPC474085
0.7778 Intermediate Similarity NPC477128
0.7753 Intermediate Similarity NPC244174
0.7717 Intermediate Similarity NPC65513
0.7692 Intermediate Similarity NPC284561
0.7684 Intermediate Similarity NPC76266
0.7674 Intermediate Similarity NPC195424
0.7653 Intermediate Similarity NPC471364
0.7653 Intermediate Similarity NPC132395
0.7653 Intermediate Similarity NPC471365
0.764 Intermediate Similarity NPC470223
0.7634 Intermediate Similarity NPC471571
0.7629 Intermediate Similarity NPC472643
0.7604 Intermediate Similarity NPC469565
0.7586 Intermediate Similarity NPC474955
0.7586 Intermediate Similarity NPC475665
0.7582 Intermediate Similarity NPC215831
0.7579 Intermediate Similarity NPC311166
0.7556 Intermediate Similarity NPC264127
0.7556 Intermediate Similarity NPC20688
0.7556 Intermediate Similarity NPC6979
0.7551 Intermediate Similarity NPC308351
0.7551 Intermediate Similarity NPC271266
0.7529 Intermediate Similarity NPC472300
0.7528 Intermediate Similarity NPC312660
0.7528 Intermediate Similarity NPC139566
0.7528 Intermediate Similarity NPC100391
0.7527 Intermediate Similarity NPC474631
0.75 Intermediate Similarity NPC187159
0.75 Intermediate Similarity NPC469547
0.75 Intermediate Similarity NPC73995
0.7474 Intermediate Similarity NPC295347
0.7474 Intermediate Similarity NPC473369
0.7473 Intermediate Similarity NPC38885
0.7471 Intermediate Similarity NPC473685
0.7447 Intermediate Similarity NPC277721
0.7447 Intermediate Similarity NPC267266
0.7444 Intermediate Similarity NPC132228
0.7444 Intermediate Similarity NPC110405
0.7444 Intermediate Similarity NPC6185
0.7444 Intermediate Similarity NPC263997
0.7444 Intermediate Similarity NPC323765
0.7444 Intermediate Similarity NPC8518
0.7444 Intermediate Similarity NPC241512
0.7444 Intermediate Similarity NPC189311
0.7442 Intermediate Similarity NPC23778
0.7442 Intermediate Similarity NPC4827
0.7423 Intermediate Similarity NPC241657
0.7419 Intermediate Similarity NPC152467
0.7419 Intermediate Similarity NPC328935
0.7419 Intermediate Similarity NPC223093
0.7419 Intermediate Similarity NPC327183
0.7416 Intermediate Similarity NPC470948
0.7416 Intermediate Similarity NPC222358
0.7416 Intermediate Similarity NPC193198
0.7416 Intermediate Similarity NPC22611
0.7396 Intermediate Similarity NPC112654
0.7396 Intermediate Similarity NPC469369
0.7396 Intermediate Similarity NPC469528
0.7391 Intermediate Similarity NPC474845
0.7391 Intermediate Similarity NPC472220
0.7391 Intermediate Similarity NPC97884
0.7391 Intermediate Similarity NPC28227
0.7386 Intermediate Similarity NPC327002
0.7386 Intermediate Similarity NPC474353
0.7381 Intermediate Similarity NPC166797
0.7368 Intermediate Similarity NPC477129
0.7368 Intermediate Similarity NPC88507
0.7368 Intermediate Similarity NPC56525
0.7368 Intermediate Similarity NPC477130
0.7368 Intermediate Similarity NPC472224
0.7368 Intermediate Similarity NPC472223
0.7363 Intermediate Similarity NPC470051
0.7363 Intermediate Similarity NPC51014
0.7363 Intermediate Similarity NPC220478
0.7363 Intermediate Similarity NPC195640
0.7363 Intermediate Similarity NPC327115
0.7363 Intermediate Similarity NPC94666
0.7363 Intermediate Similarity NPC470050
0.7356 Intermediate Similarity NPC476177
0.7356 Intermediate Similarity NPC327674
0.7347 Intermediate Similarity NPC472644
0.7347 Intermediate Similarity NPC474802
0.734 Intermediate Similarity NPC179517
0.734 Intermediate Similarity NPC26865
0.734 Intermediate Similarity NPC218301
0.734 Intermediate Similarity NPC165904
0.7333 Intermediate Similarity NPC237712
0.7327 Intermediate Similarity NPC470267
0.7326 Intermediate Similarity NPC283087
0.732 Intermediate Similarity NPC257726
0.732 Intermediate Similarity NPC204054
0.732 Intermediate Similarity NPC208094
0.7317 Intermediate Similarity NPC199557
0.7312 Intermediate Similarity NPC305039
0.7303 Intermediate Similarity NPC328351
0.7303 Intermediate Similarity NPC100297
0.7303 Intermediate Similarity NPC151519
0.7303 Intermediate Similarity NPC178676
0.7303 Intermediate Similarity NPC240302
0.7283 Intermediate Similarity NPC167877
0.7273 Intermediate Similarity NPC108955
0.7273 Intermediate Similarity NPC2482
0.7273 Intermediate Similarity NPC267517
0.7273 Intermediate Similarity NPC472702
0.7273 Intermediate Similarity NPC472685
0.7263 Intermediate Similarity NPC79117
0.7263 Intermediate Similarity NPC166346
0.7263 Intermediate Similarity NPC470656
0.7263 Intermediate Similarity NPC109414
0.7253 Intermediate Similarity NPC329738
0.7253 Intermediate Similarity NPC469948
0.7253 Intermediate Similarity NPC474680
0.7241 Intermediate Similarity NPC321514
0.7234 Intermediate Similarity NPC214844
0.7234 Intermediate Similarity NPC212679
0.7234 Intermediate Similarity NPC220454
0.7234 Intermediate Similarity NPC469595
0.7234 Intermediate Similarity NPC129913
0.7234 Intermediate Similarity NPC15059
0.7228 Intermediate Similarity NPC235889
0.7222 Intermediate Similarity NPC470046
0.7222 Intermediate Similarity NPC278648
0.7222 Intermediate Similarity NPC8091
0.7222 Intermediate Similarity NPC470047
0.7222 Intermediate Similarity NPC476082
0.7216 Intermediate Similarity NPC73858
0.7212 Intermediate Similarity NPC163314
0.7209 Intermediate Similarity NPC899
0.7209 Intermediate Similarity NPC69143
0.7204 Intermediate Similarity NPC196407
0.7204 Intermediate Similarity NPC226863
0.7191 Intermediate Similarity NPC225515
0.7191 Intermediate Similarity NPC121984
0.7191 Intermediate Similarity NPC475951
0.7191 Intermediate Similarity NPC55869
0.7191 Intermediate Similarity NPC14151
0.7191 Intermediate Similarity NPC473420
0.7191 Intermediate Similarity NPC475833
0.7188 Intermediate Similarity NPC293086
0.7188 Intermediate Similarity NPC477439
0.7184 Intermediate Similarity NPC470269
0.7176 Intermediate Similarity NPC306928
0.7174 Intermediate Similarity NPC118266
0.7174 Intermediate Similarity NPC202394
0.7172 Intermediate Similarity NPC472972
0.7159 Intermediate Similarity NPC477371
0.7159 Intermediate Similarity NPC28319
0.7159 Intermediate Similarity NPC474113
0.7158 Intermediate Similarity NPC141831
0.7158 Intermediate Similarity NPC49420
0.7158 Intermediate Similarity NPC186363
0.7158 Intermediate Similarity NPC190442
0.7158 Intermediate Similarity NPC233345
0.7157 Intermediate Similarity NPC472645
0.7157 Intermediate Similarity NPC470309
0.7157 Intermediate Similarity NPC475571
0.7157 Intermediate Similarity NPC181265
0.7157 Intermediate Similarity NPC127790
0.7143 Intermediate Similarity NPC201992
0.7143 Intermediate Similarity NPC469407
0.7143 Intermediate Similarity NPC221758
0.7143 Intermediate Similarity NPC25833
0.7143 Intermediate Similarity NPC474359
0.7143 Intermediate Similarity NPC38530
0.7143 Intermediate Similarity NPC109512
0.7143 Intermediate Similarity NPC226986
0.7143 Intermediate Similarity NPC59453
0.7143 Intermediate Similarity NPC472188
0.7143 Intermediate Similarity NPC84335
0.7143 Intermediate Similarity NPC292133
0.7143 Intermediate Similarity NPC71626
0.7128 Intermediate Similarity NPC76879
0.7128 Intermediate Similarity NPC474245
0.7128 Intermediate Similarity NPC293044
0.7128 Intermediate Similarity NPC11611
0.7128 Intermediate Similarity NPC471222
0.7128 Intermediate Similarity NPC474570
0.7128 Intermediate Similarity NPC474700
0.7128 Intermediate Similarity NPC50070
0.7128 Intermediate Similarity NPC5509
0.7113 Intermediate Similarity NPC469599
0.7113 Intermediate Similarity NPC477438
0.7113 Intermediate Similarity NPC477437
0.7113 Intermediate Similarity NPC31021
0.7111 Intermediate Similarity NPC163236
0.7111 Intermediate Similarity NPC321289
0.7111 Intermediate Similarity NPC103486
0.7111 Intermediate Similarity NPC186276
0.7111 Intermediate Similarity NPC470813
0.7111 Intermediate Similarity NPC73882

  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 NPC469569 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
0.7778 Intermediate Similarity NPD6672 Approved
0.7778 Intermediate Similarity NPD5737 Approved
0.7556 Intermediate Similarity NPD6098 Approved
0.7363 Intermediate Similarity NPD7146 Approved
0.7363 Intermediate Similarity NPD5330 Approved
0.7363 Intermediate Similarity NPD7521 Approved
0.7363 Intermediate Similarity NPD6684 Approved
0.7363 Intermediate Similarity NPD7334 Approved
0.7363 Intermediate Similarity NPD6409 Approved
0.734 Intermediate Similarity NPD5694 Approved
0.7312 Intermediate Similarity NPD6904 Approved
0.7312 Intermediate Similarity NPD6673 Approved
0.7312 Intermediate Similarity NPD6080 Approved
0.7303 Intermediate Similarity NPD3667 Approved
0.7292 Intermediate Similarity NPD5695 Phase 3
0.7263 Intermediate Similarity NPD6399 Phase 3
0.7238 Intermediate Similarity NPD6882 Approved
0.7234 Intermediate Similarity NPD5692 Phase 3
0.7204 Intermediate Similarity NPD6903 Approved
0.7204 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD5693 Phase 1
0.7158 Intermediate Similarity NPD6050 Approved
0.7143 Intermediate Similarity NPD4786 Approved
0.7143 Intermediate Similarity NPD6083 Phase 2
0.7143 Intermediate Similarity NPD3668 Phase 3
0.7143 Intermediate Similarity NPD6084 Phase 2
0.7097 Intermediate Similarity NPD3573 Approved
0.7087 Intermediate Similarity NPD5697 Approved
0.7079 Intermediate Similarity NPD4695 Discontinued
0.7071 Intermediate Similarity NPD5696 Approved
0.7065 Intermediate Similarity NPD1694 Approved
0.7053 Intermediate Similarity NPD5207 Approved
0.7019 Intermediate Similarity NPD6899 Approved
0.7019 Intermediate Similarity NPD6881 Approved
0.7019 Intermediate Similarity NPD6011 Approved
0.699 Remote Similarity NPD6675 Approved
0.699 Remote Similarity NPD7128 Approved
0.699 Remote Similarity NPD6402 Approved
0.699 Remote Similarity NPD5739 Approved
0.6989 Remote Similarity NPD5279 Phase 3
0.6989 Remote Similarity NPD5690 Phase 2
0.6957 Remote Similarity NPD3665 Phase 1
0.6957 Remote Similarity NPD3666 Approved
0.6957 Remote Similarity NPD3133 Approved
0.6957 Remote Similarity NPD4197 Approved
0.6952 Remote Similarity NPD6014 Approved
0.6952 Remote Similarity NPD6012 Approved
0.6952 Remote Similarity NPD6013 Approved
0.6947 Remote Similarity NPD4753 Phase 2
0.6937 Remote Similarity NPD6054 Approved
0.6923 Remote Similarity NPD5701 Approved
0.6923 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6887 Remote Similarity NPD7102 Approved
0.6887 Remote Similarity NPD6883 Approved
0.6887 Remote Similarity NPD7290 Approved
0.6882 Remote Similarity NPD5329 Approved
0.6875 Remote Similarity NPD6015 Approved
0.6875 Remote Similarity NPD6016 Approved
0.6869 Remote Similarity NPD5221 Approved
0.6869 Remote Similarity NPD5222 Approved
0.6869 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6857 Remote Similarity NPD7320 Approved
0.6854 Remote Similarity NPD3617 Approved
0.6842 Remote Similarity NPD5208 Approved
0.6837 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7900 Approved
0.6832 Remote Similarity NPD4696 Approved
0.6832 Remote Similarity NPD5286 Approved
0.6832 Remote Similarity NPD5285 Approved
0.6827 Remote Similarity NPD6008 Approved
0.6822 Remote Similarity NPD6617 Approved
0.6822 Remote Similarity NPD6869 Approved
0.6822 Remote Similarity NPD6650 Approved
0.6822 Remote Similarity NPD6649 Approved
0.6822 Remote Similarity NPD8130 Phase 1
0.6822 Remote Similarity NPD6847 Approved
0.6818 Remote Similarity NPD6009 Approved
0.6814 Remote Similarity NPD5988 Approved
0.6814 Remote Similarity NPD6370 Approved
0.6809 Remote Similarity NPD3618 Phase 1
0.6809 Remote Similarity NPD4694 Approved
0.6809 Remote Similarity NPD5280 Approved
0.6804 Remote Similarity NPD6079 Approved
0.68 Remote Similarity NPD4755 Approved
0.68 Remote Similarity NPD5173 Approved
0.6792 Remote Similarity NPD6373 Approved
0.6792 Remote Similarity NPD6372 Approved
0.6786 Remote Similarity NPD6059 Approved
0.6771 Remote Similarity NPD5328 Approved
0.6768 Remote Similarity NPD4629 Approved
0.6768 Remote Similarity NPD5654 Approved
0.6768 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6768 Remote Similarity NPD5210 Approved
0.6765 Remote Similarity NPD5223 Approved
0.6762 Remote Similarity NPD6412 Phase 2
0.6759 Remote Similarity NPD8297 Approved
0.6739 Remote Similarity NPD4221 Approved
0.6739 Remote Similarity NPD4223 Phase 3
0.6706 Remote Similarity NPD4137 Phase 3
0.67 Remote Similarity NPD4697 Phase 3
0.6699 Remote Similarity NPD5225 Approved
0.6699 Remote Similarity NPD5211 Phase 2
0.6699 Remote Similarity NPD5226 Approved
0.6699 Remote Similarity NPD4633 Approved
0.6699 Remote Similarity NPD5224 Approved
0.6696 Remote Similarity NPD7492 Approved
0.6667 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6001 Approved
0.6667 Remote Similarity NPD5282 Discontinued
0.6667 Remote Similarity NPD4700 Approved
0.6667 Remote Similarity NPD7748 Approved
0.6638 Remote Similarity NPD6616 Approved
0.6635 Remote Similarity NPD5175 Approved
0.6635 Remote Similarity NPD5174 Approved
0.6634 Remote Similarity NPD7902 Approved
0.6634 Remote Similarity NPD5959 Approved
0.6633 Remote Similarity NPD5284 Approved
0.6633 Remote Similarity NPD6411 Approved
0.6633 Remote Similarity NPD5281 Approved
0.6632 Remote Similarity NPD4519 Discontinued
0.6632 Remote Similarity NPD4623 Approved
0.6628 Remote Similarity NPD4747 Approved
0.6628 Remote Similarity NPD4691 Approved
0.6598 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6591 Remote Similarity NPD4058 Approved
0.6591 Remote Similarity NPD4687 Approved
0.6588 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6581 Remote Similarity NPD7078 Approved
0.6571 Remote Similarity NPD5141 Approved
0.6566 Remote Similarity NPD4202 Approved
0.6525 Remote Similarity NPD7736 Approved
0.6518 Remote Similarity NPD6317 Approved
0.6517 Remote Similarity NPD8039 Approved
0.6476 Remote Similarity NPD4754 Approved
0.6465 Remote Similarity NPD7515 Phase 2
0.646 Remote Similarity NPD6335 Approved
0.646 Remote Similarity NPD6313 Approved
0.646 Remote Similarity NPD6314 Approved
0.6458 Remote Similarity NPD4688 Approved
0.6458 Remote Similarity NPD5205 Approved
0.6458 Remote Similarity NPD4693 Phase 3
0.6458 Remote Similarity NPD4690 Approved
0.6458 Remote Similarity NPD4138 Approved
0.6458 Remote Similarity NPD4689 Approved
0.6449 Remote Similarity NPD6614 Approved
0.6441 Remote Similarity NPD8293 Discontinued
0.6429 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6274 Approved
0.6429 Remote Similarity NPD6868 Approved
0.6429 Remote Similarity NPD6101 Approved
0.6404 Remote Similarity NPD7101 Approved
0.6404 Remote Similarity NPD5733 Approved
0.6404 Remote Similarity NPD7100 Approved
0.6396 Remote Similarity NPD4632 Approved
0.6389 Remote Similarity NPD4730 Approved
0.6389 Remote Similarity NPD4729 Approved
0.6387 Remote Similarity NPD6033 Approved
0.6383 Remote Similarity NPD6435 Approved
0.6373 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5276 Approved
0.6355 Remote Similarity NPD4768 Approved
0.6355 Remote Similarity NPD4767 Approved
0.6353 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6348 Remote Similarity NPD6319 Approved
0.6325 Remote Similarity NPD8328 Phase 3
0.6293 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6293 Remote Similarity NPD5983 Phase 2
0.6289 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6281 Remote Similarity NPD5956 Approved
0.6277 Remote Similarity NPD4139 Approved
0.6277 Remote Similarity NPD4692 Approved
0.6275 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6273 Remote Similarity NPD5250 Approved
0.6273 Remote Similarity NPD5247 Approved
0.6273 Remote Similarity NPD4634 Approved
0.6273 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6273 Remote Similarity NPD5248 Approved
0.6273 Remote Similarity NPD5169 Approved
0.6273 Remote Similarity NPD5249 Phase 3
0.6273 Remote Similarity NPD5135 Approved
0.6273 Remote Similarity NPD5251 Approved
0.6264 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6239 Remote Similarity NPD5168 Approved
0.6239 Remote Similarity NPD6686 Approved
0.6239 Remote Similarity NPD5128 Approved
0.6238 Remote Similarity NPD5779 Approved
0.6238 Remote Similarity NPD5133 Approved
0.6238 Remote Similarity NPD5778 Approved
0.6237 Remote Similarity NPD4195 Approved
0.6228 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6216 Remote Similarity NPD5217 Approved
0.6216 Remote Similarity NPD5216 Approved
0.6216 Remote Similarity NPD5215 Approved
0.6216 Remote Similarity NPD5127 Approved
0.6214 Remote Similarity NPD7732 Phase 3
0.6186 Remote Similarity NPD1696 Phase 3
0.6186 Remote Similarity NPD7604 Phase 2
0.618 Remote Similarity NPD5777 Approved
0.617 Remote Similarity NPD5368 Approved
0.617 Remote Similarity NPD8259 Clinical (unspecified phase)

  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