Structure

Physi-Chem Properties

Molecular Weight:  332.2
Volume:  353.422
LogP:  2.998
LogD:  2.533
LogS:  -3.109
# Rotatable Bonds:  4
TPSA:  70.67
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.878
Synthetic Accessibility Score:  4.523
Fsp3:  0.65
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.033
MDCK Permeability:  1.3356725503399502e-05
Pgp-inhibitor:  0.292
Pgp-substrate:  0.047
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.117
Plasma Protein Binding (PPB):  90.19281005859375%
Volume Distribution (VD):  0.967
Pgp-substrate:  5.7089128494262695%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.565
CYP2C19-inhibitor:  0.04
CYP2C19-substrate:  0.536
CYP2C9-inhibitor:  0.08
CYP2C9-substrate:  0.163
CYP2D6-inhibitor:  0.016
CYP2D6-substrate:  0.236
CYP3A4-inhibitor:  0.131
CYP3A4-substrate:  0.351

ADMET: Excretion

Clearance (CL):  20.864
Half-life (T1/2):  0.889

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.648
Drug-inuced Liver Injury (DILI):  0.041
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.482
Maximum Recommended Daily Dose:  0.372
Skin Sensitization:  0.732
Carcinogencity:  0.889
Eye Corrosion:  0.038
Eye Irritation:  0.129
Respiratory Toxicity:  0.97

Download Data

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

  Natural Product: NPC5509

Natural Product ID:  NPC5509
Common Name*:   Gomphostenin
IUPAC Name:   4-[2-[(1S,2R,4aS,8aS)-2-(hydroxymethyl)-1,4a,5-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]ethyl]-2H-furan-5-one
Synonyms:   Gomphostenin
Standard InCHIKey:  TUKIEDUNYYIEJB-JQERWDHBSA-N
Standard InCHI:  InChI=1S/C20H28O4/c1-13-10-16(22)11-17-19(13,2)8-5-15(12-21)20(17,3)7-4-14-6-9-24-18(14)23/h6,10,15,17,21H,4-5,7-9,11-12H2,1-3H3/t15-,17+,19+,20+/m0/s1
SMILES:  OC[C@@H]1CC[C@]2([C@H]([C@]1(C)CCC1=CCOC1=O)CC(=O)C=C2C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL597125
PubChem CID:   46216681
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO2879 Gomphostemma niveum Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[20022506]
NPO2879 Gomphostemma niveum Species Lamiaceae 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 38.2 ug.mL-1 PMID[511783]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 37.7 ug.mL-1 PMID[511783]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 115000.0 nM PMID[511784]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 113500.0 nM PMID[511784]

☑ 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 NPC5509 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
0.9518 High Similarity NPC189311
0.9419 High Similarity NPC51486
0.9302 High Similarity NPC174342
0.9286 High Similarity NPC86316
0.9286 High Similarity NPC106416
0.9286 High Similarity NPC65661
0.9205 High Similarity NPC115021
0.908 High Similarity NPC168131
0.907 High Similarity NPC312561
0.9011 High Similarity NPC208094
0.9 High Similarity NPC209355
0.9 High Similarity NPC295347
0.8989 High Similarity NPC139692
0.8977 High Similarity NPC281942
0.8977 High Similarity NPC232426
0.8966 High Similarity NPC226863
0.8929 High Similarity NPC200513
0.8876 High Similarity NPC472814
0.8876 High Similarity NPC141831
0.8876 High Similarity NPC477783
0.8876 High Similarity NPC177037
0.8824 High Similarity NPC193198
0.8817 High Similarity NPC476299
0.8817 High Similarity NPC474012
0.8791 High Similarity NPC183012
0.8764 High Similarity NPC477782
0.8721 High Similarity NPC30486
0.8721 High Similarity NPC149869
0.8696 High Similarity NPC242848
0.8696 High Similarity NPC234993
0.8696 High Similarity NPC134072
0.8681 High Similarity NPC476415
0.8681 High Similarity NPC53685
0.8652 High Similarity NPC251528
0.8617 High Similarity NPC54705
0.8617 High Similarity NPC117685
0.8605 High Similarity NPC22611
0.8602 High Similarity NPC475709
0.8602 High Similarity NPC53844
0.8602 High Similarity NPC253826
0.8602 High Similarity NPC476253
0.8602 High Similarity NPC474343
0.8588 High Similarity NPC14203
0.8588 High Similarity NPC40228
0.8588 High Similarity NPC229584
0.8588 High Similarity NPC282293
0.8571 High Similarity NPC472303
0.8571 High Similarity NPC475657
0.8571 High Similarity NPC166346
0.8556 High Similarity NPC476437
0.8556 High Similarity NPC476369
0.8554 High Similarity NPC316500
0.8539 High Similarity NPC472302
0.8526 High Similarity NPC471412
0.8523 High Similarity NPC474062
0.8523 High Similarity NPC220478
0.8511 High Similarity NPC57079
0.8511 High Similarity NPC23364
0.8511 High Similarity NPC316598
0.8511 High Similarity NPC108368
0.8506 High Similarity NPC475100
0.8495 Intermediate Similarity NPC202833
0.8495 Intermediate Similarity NPC29952
0.8478 Intermediate Similarity NPC474554
0.8462 Intermediate Similarity NPC186363
0.8462 Intermediate Similarity NPC233345
0.8462 Intermediate Similarity NPC303697
0.8462 Intermediate Similarity NPC289479
0.8452 Intermediate Similarity NPC74410
0.8452 Intermediate Similarity NPC471220
0.8444 Intermediate Similarity NPC284561
0.8444 Intermediate Similarity NPC470734
0.8434 Intermediate Similarity NPC180886
0.8421 Intermediate Similarity NPC476274
0.8421 Intermediate Similarity NPC476767
0.8421 Intermediate Similarity NPC201406
0.8421 Intermediate Similarity NPC472644
0.8421 Intermediate Similarity NPC471413
0.8409 Intermediate Similarity NPC30984
0.8409 Intermediate Similarity NPC42586
0.8409 Intermediate Similarity NPC473251
0.8391 Intermediate Similarity NPC49019
0.8391 Intermediate Similarity NPC311070
0.8391 Intermediate Similarity NPC118423
0.8391 Intermediate Similarity NPC97913
0.8387 Intermediate Similarity NPC171395
0.8387 Intermediate Similarity NPC293052
0.8372 Intermediate Similarity NPC278459
0.8372 Intermediate Similarity NPC90055
0.8372 Intermediate Similarity NPC327002
0.837 Intermediate Similarity NPC469939
0.837 Intermediate Similarity NPC242069
0.837 Intermediate Similarity NPC169343
0.837 Intermediate Similarity NPC476416
0.837 Intermediate Similarity NPC472871
0.8353 Intermediate Similarity NPC150646
0.8353 Intermediate Similarity NPC327674
0.8352 Intermediate Similarity NPC477147
0.8352 Intermediate Similarity NPC477149
0.8352 Intermediate Similarity NPC220454
0.8352 Intermediate Similarity NPC198818
0.8352 Intermediate Similarity NPC8062
0.8352 Intermediate Similarity NPC469595
0.8352 Intermediate Similarity NPC212679
0.8351 Intermediate Similarity NPC112009
0.8351 Intermediate Similarity NPC476889
0.8333 Intermediate Similarity NPC24816
0.8333 Intermediate Similarity NPC215831
0.8333 Intermediate Similarity NPC472643
0.8333 Intermediate Similarity NPC63249
0.8333 Intermediate Similarity NPC224720
0.8333 Intermediate Similarity NPC97377
0.8333 Intermediate Similarity NPC476240
0.8333 Intermediate Similarity NPC472870
0.8333 Intermediate Similarity NPC476223
0.8316 Intermediate Similarity NPC222011
0.8316 Intermediate Similarity NPC478056
0.8316 Intermediate Similarity NPC98868
0.8315 Intermediate Similarity NPC471219
0.8315 Intermediate Similarity NPC131813
0.8315 Intermediate Similarity NPC168248
0.8315 Intermediate Similarity NPC322159
0.8315 Intermediate Similarity NPC194417
0.83 Intermediate Similarity NPC137911
0.83 Intermediate Similarity NPC228477
0.8298 Intermediate Similarity NPC470801
0.8298 Intermediate Similarity NPC240673
0.8298 Intermediate Similarity NPC472941
0.8298 Intermediate Similarity NPC456
0.8298 Intermediate Similarity NPC17578
0.8295 Intermediate Similarity NPC31086
0.8295 Intermediate Similarity NPC71626
0.8295 Intermediate Similarity NPC164577
0.8295 Intermediate Similarity NPC472865
0.8283 Intermediate Similarity NPC91034
0.8283 Intermediate Similarity NPC475294
0.828 Intermediate Similarity NPC470697
0.828 Intermediate Similarity NPC477129
0.828 Intermediate Similarity NPC474555
0.828 Intermediate Similarity NPC477130
0.828 Intermediate Similarity NPC84893
0.8276 Intermediate Similarity NPC268122
0.8276 Intermediate Similarity NPC186276
0.8261 Intermediate Similarity NPC474018
0.8261 Intermediate Similarity NPC72845
0.8261 Intermediate Similarity NPC65513
0.8261 Intermediate Similarity NPC179517
0.8261 Intermediate Similarity NPC252433
0.8261 Intermediate Similarity NPC473986
0.8261 Intermediate Similarity NPC470113
0.8261 Intermediate Similarity NPC165904
0.8256 Intermediate Similarity NPC195424
0.8256 Intermediate Similarity NPC271104
0.8247 Intermediate Similarity NPC31058
0.8247 Intermediate Similarity NPC40918
0.8247 Intermediate Similarity NPC469606
0.8247 Intermediate Similarity NPC273005
0.8247 Intermediate Similarity NPC155332
0.8247 Intermediate Similarity NPC134077
0.8247 Intermediate Similarity NPC476081
0.8247 Intermediate Similarity NPC114540
0.8247 Intermediate Similarity NPC32577
0.8247 Intermediate Similarity NPC476890
0.8247 Intermediate Similarity NPC162973
0.8242 Intermediate Similarity NPC50488
0.8242 Intermediate Similarity NPC118011
0.8242 Intermediate Similarity NPC474396
0.8242 Intermediate Similarity NPC477973
0.8242 Intermediate Similarity NPC73995
0.8242 Intermediate Similarity NPC36668
0.8242 Intermediate Similarity NPC214387
0.8235 Intermediate Similarity NPC198240
0.8235 Intermediate Similarity NPC62336
0.8235 Intermediate Similarity NPC321514
0.8229 Intermediate Similarity NPC477720
0.8222 Intermediate Similarity NPC171722
0.8222 Intermediate Similarity NPC477228
0.8214 Intermediate Similarity NPC27205
0.8214 Intermediate Similarity NPC263582
0.8214 Intermediate Similarity NPC40353
0.8211 Intermediate Similarity NPC69385
0.8211 Intermediate Similarity NPC91695
0.8211 Intermediate Similarity NPC170131
0.8211 Intermediate Similarity NPC175351
0.8211 Intermediate Similarity NPC202705
0.8211 Intermediate Similarity NPC132753
0.8211 Intermediate Similarity NPC121402
0.8211 Intermediate Similarity NPC70145
0.8211 Intermediate Similarity NPC38530
0.8211 Intermediate Similarity NPC224356
0.8211 Intermediate Similarity NPC84335
0.8211 Intermediate Similarity NPC151681
0.8202 Intermediate Similarity NPC474860
0.8202 Intermediate Similarity NPC471300
0.8202 Intermediate Similarity NPC471795
0.8202 Intermediate Similarity NPC177932
0.8202 Intermediate Similarity NPC52628
0.8202 Intermediate Similarity NPC474680
0.82 Intermediate Similarity NPC472825
0.82 Intermediate Similarity NPC220155

  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 NPC5509 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
0.8929 High Similarity NPD4752 Clinical (unspecified phase)
0.8202 Intermediate Similarity NPD1694 Approved
0.8021 Intermediate Similarity NPD6084 Phase 2
0.8021 Intermediate Similarity NPD6083 Phase 2
0.8 Intermediate Similarity NPD5695 Phase 3
0.7938 Intermediate Similarity NPD7638 Approved
0.7935 Intermediate Similarity NPD5737 Approved
0.7935 Intermediate Similarity NPD6672 Approved
0.7912 Intermediate Similarity NPD6409 Approved
0.7912 Intermediate Similarity NPD5330 Approved
0.7912 Intermediate Similarity NPD7146 Approved
0.7912 Intermediate Similarity NPD6684 Approved
0.7912 Intermediate Similarity NPD7334 Approved
0.7912 Intermediate Similarity NPD7521 Approved
0.7895 Intermediate Similarity NPD7748 Approved
0.7889 Intermediate Similarity NPD3666 Approved
0.7889 Intermediate Similarity NPD3665 Phase 1
0.7889 Intermediate Similarity NPD3133 Approved
0.7872 Intermediate Similarity NPD5693 Phase 1
0.7872 Intermediate Similarity NPD7515 Phase 2
0.7857 Intermediate Similarity NPD7640 Approved
0.7857 Intermediate Similarity NPD7639 Approved
0.7843 Intermediate Similarity NPD6686 Approved
0.7789 Intermediate Similarity NPD6399 Phase 3
0.7755 Intermediate Similarity NPD4225 Approved
0.7755 Intermediate Similarity NPD5696 Approved
0.7742 Intermediate Similarity NPD6903 Approved
0.7742 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD3618 Phase 1
0.7667 Intermediate Similarity NPD3667 Approved
0.766 Intermediate Similarity NPD4753 Phase 2
0.7653 Intermediate Similarity NPD7902 Approved
0.764 Intermediate Similarity NPD4695 Discontinued
0.7593 Intermediate Similarity NPD7115 Discovery
0.7579 Intermediate Similarity NPD5785 Approved
0.7573 Intermediate Similarity NPD5697 Approved
0.7527 Intermediate Similarity NPD4519 Discontinued
0.7527 Intermediate Similarity NPD4623 Approved
0.7527 Intermediate Similarity NPD5279 Phase 3
0.75 Intermediate Similarity NPD6011 Approved
0.75 Intermediate Similarity NPD6881 Approved
0.75 Intermediate Similarity NPD5281 Approved
0.75 Intermediate Similarity NPD5284 Approved
0.75 Intermediate Similarity NPD6899 Approved
0.75 Intermediate Similarity NPD4786 Approved
0.75 Intermediate Similarity NPD6079 Approved
0.7476 Intermediate Similarity NPD5739 Approved
0.7476 Intermediate Similarity NPD6675 Approved
0.7476 Intermediate Similarity NPD7128 Approved
0.7476 Intermediate Similarity NPD6402 Approved
0.7474 Intermediate Similarity NPD6080 Approved
0.7474 Intermediate Similarity NPD6673 Approved
0.7474 Intermediate Similarity NPD5328 Approved
0.7474 Intermediate Similarity NPD6904 Approved
0.7473 Intermediate Similarity NPD4221 Approved
0.7473 Intermediate Similarity NPD4223 Phase 3
0.7449 Intermediate Similarity NPD4629 Approved
0.7449 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD5210 Approved
0.7447 Intermediate Similarity NPD3573 Approved
0.7429 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD6012 Approved
0.7429 Intermediate Similarity NPD6014 Approved
0.7429 Intermediate Similarity NPD6013 Approved
0.7404 Intermediate Similarity NPD5701 Approved
0.7396 Intermediate Similarity NPD5692 Phase 3
0.7374 Intermediate Similarity NPD5221 Approved
0.7374 Intermediate Similarity NPD5222 Approved
0.7374 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD5208 Approved
0.7358 Intermediate Similarity NPD6883 Approved
0.7358 Intermediate Similarity NPD7102 Approved
0.7358 Intermediate Similarity NPD7290 Approved
0.7347 Intermediate Similarity NPD7900 Approved
0.7347 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD5690 Phase 2
0.734 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7320 Approved
0.732 Intermediate Similarity NPD6050 Approved
0.732 Intermediate Similarity NPD5694 Approved
0.7312 Intermediate Similarity NPD4197 Approved
0.7312 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD5173 Approved
0.7292 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6869 Approved
0.729 Intermediate Similarity NPD6847 Approved
0.729 Intermediate Similarity NPD6650 Approved
0.729 Intermediate Similarity NPD6617 Approved
0.729 Intermediate Similarity NPD6649 Approved
0.729 Intermediate Similarity NPD8130 Phase 1
0.7273 Intermediate Similarity NPD8039 Approved
0.7273 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD6372 Approved
0.7264 Intermediate Similarity NPD6373 Approved
0.7245 Intermediate Similarity NPD4202 Approved
0.7234 Intermediate Similarity NPD5329 Approved
0.7222 Intermediate Similarity NPD8297 Approved
0.7222 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD3617 Approved
0.7222 Intermediate Similarity NPD6882 Approved
0.7216 Intermediate Similarity NPD5207 Approved
0.72 Intermediate Similarity NPD4697 Phase 3
0.7196 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD7632 Discontinued
0.7184 Intermediate Similarity NPD5211 Phase 2
0.7158 Intermediate Similarity NPD4694 Approved
0.7158 Intermediate Similarity NPD5280 Approved
0.7158 Intermediate Similarity NPD4690 Approved
0.7158 Intermediate Similarity NPD4693 Phase 3
0.7158 Intermediate Similarity NPD4138 Approved
0.7158 Intermediate Similarity NPD5205 Approved
0.7158 Intermediate Similarity NPD4688 Approved
0.7158 Intermediate Similarity NPD6098 Approved
0.7158 Intermediate Similarity NPD4689 Approved
0.7157 Intermediate Similarity NPD5285 Approved
0.7157 Intermediate Similarity NPD5286 Approved
0.7157 Intermediate Similarity NPD4696 Approved
0.7143 Intermediate Similarity NPD6411 Approved
0.713 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD4755 Approved
0.7128 Intermediate Similarity NPD3668 Phase 3
0.7113 Intermediate Similarity NPD6051 Approved
0.7097 Intermediate Similarity NPD5209 Approved
0.7087 Intermediate Similarity NPD5223 Approved
0.7075 Intermediate Similarity NPD6412 Phase 2
0.7071 Intermediate Similarity NPD5778 Approved
0.7071 Intermediate Similarity NPD5779 Approved
0.7064 Intermediate Similarity NPD6053 Discontinued
0.7053 Intermediate Similarity NPD5363 Approved
0.7048 Intermediate Similarity NPD5141 Approved
0.7041 Intermediate Similarity NPD6698 Approved
0.7041 Intermediate Similarity NPD46 Approved
0.703 Intermediate Similarity NPD7614 Phase 1
0.7027 Intermediate Similarity NPD6274 Approved
0.7027 Intermediate Similarity NPD6868 Approved
0.7021 Intermediate Similarity NPD4788 Approved
0.7019 Intermediate Similarity NPD5225 Approved
0.7019 Intermediate Similarity NPD4633 Approved
0.7019 Intermediate Similarity NPD5226 Approved
0.7019 Intermediate Similarity NPD5224 Approved
0.7011 Intermediate Similarity NPD4691 Approved
0.7 Intermediate Similarity NPD6001 Approved
0.7 Intermediate Similarity NPD4632 Approved
0.699 Remote Similarity NPD4700 Approved
0.699 Remote Similarity NPD6404 Discontinued
0.6964 Remote Similarity NPD6317 Approved
0.6957 Remote Similarity NPD4195 Approved
0.6952 Remote Similarity NPD5174 Approved
0.6952 Remote Similarity NPD5175 Approved
0.6939 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6101 Approved
0.6931 Remote Similarity NPD5654 Approved
0.6916 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6903 Remote Similarity NPD6335 Approved
0.6903 Remote Similarity NPD6314 Approved
0.6903 Remote Similarity NPD6313 Approved
0.6897 Remote Similarity NPD4137 Phase 3
0.6881 Remote Similarity NPD6371 Approved
0.6875 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1696 Phase 3
0.6863 Remote Similarity NPD7732 Phase 3
0.6842 Remote Similarity NPD7100 Approved
0.6842 Remote Similarity NPD7101 Approved
0.6842 Remote Similarity NPD5362 Discontinued
0.6842 Remote Similarity NPD7154 Phase 3
0.6822 Remote Similarity NPD6008 Approved
0.6818 Remote Similarity NPD4747 Approved
0.6814 Remote Similarity NPD6009 Approved
0.68 Remote Similarity NPD8034 Phase 2
0.68 Remote Similarity NPD7637 Suspended
0.68 Remote Similarity NPD8035 Phase 2
0.6796 Remote Similarity NPD5959 Approved
0.6792 Remote Similarity NPD4754 Approved
0.6783 Remote Similarity NPD6319 Approved
0.678 Remote Similarity NPD7507 Approved
0.6778 Remote Similarity NPD4058 Approved
0.6739 Remote Similarity NPD4756 Discovery
0.6737 Remote Similarity NPD4270 Approved
0.6737 Remote Similarity NPD6435 Approved
0.6737 Remote Similarity NPD4269 Approved
0.6724 Remote Similarity NPD5983 Phase 2
0.6724 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6701 Remote Similarity NPD6082 Clinical (unspecified phase)
0.67 Remote Similarity NPD4096 Approved
0.6697 Remote Similarity NPD5168 Approved
0.6697 Remote Similarity NPD4730 Approved
0.6697 Remote Similarity NPD4729 Approved
0.6697 Remote Similarity NPD5128 Approved
0.6667 Remote Similarity NPD4768 Approved
0.6667 Remote Similarity NPD4767 Approved
0.6636 Remote Similarity NPD6052 Approved
0.6633 Remote Similarity NPD5786 Approved
0.6632 Remote Similarity NPD4139 Approved
0.6632 Remote Similarity NPD5369 Approved
0.6632 Remote Similarity NPD4692 Approved
0.663 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6612 Remote Similarity NPD7319 Approved
0.661 Remote Similarity NPD7604 Phase 2
0.6606 Remote Similarity NPD6614 Approved
0.6593 Remote Similarity NPD4687 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