Structure

Physi-Chem Properties

Molecular Weight:  248.14
Volume:  260.788
LogP:  1.44
LogD:  1.14
LogS:  -4.188
# Rotatable Bonds:  1
TPSA:  49.83
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.57
Synthetic Accessibility Score:  4.984
Fsp3:  0.667
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:  -4.798
MDCK Permeability:  3.394367377040908e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.227
Plasma Protein Binding (PPB):  56.521400451660156%
Volume Distribution (VD):  1.143
Pgp-substrate:  47.685909271240234%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.939
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.904
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.046
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.182
CYP3A4-inhibitor:  0.017
CYP3A4-substrate:  0.581

ADMET: Excretion

Clearance (CL):  1.704
Half-life (T1/2):  0.884

ADMET: Toxicity

hERG Blockers:  0.036
Human Hepatotoxicity (H-HT):  0.608
Drug-inuced Liver Injury (DILI):  0.088
AMES Toxicity:  0.654
Rat Oral Acute Toxicity:  0.193
Maximum Recommended Daily Dose:  0.642
Skin Sensitization:  0.88
Carcinogencity:  0.102
Eye Corrosion:  0.138
Eye Irritation:  0.695
Respiratory Toxicity:  0.664

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  Natural Product: NPC94337

Natural Product ID:  NPC94337
Common Name*:   Gnf-Pf-1841
IUPAC Name:   (1aR,6R,7R,7aR,7bR)-6-hydroxy-7,7a-dimethyl-1a-prop-1-en-2-yl-5,6,7,7b-tetrahydro-4H-naphtho[1,2-b]oxiren-2-one
Synonyms:   GNF-Pf-1841
Standard InCHIKey:  PCBDXYONDOCJPR-OANMRLRGSA-N
Standard InCHI:  InChI=1S/C15H20O3/c1-8(2)15-12(17)7-10-5-6-11(16)9(3)14(10,4)13(15)18-15/h7,9,11,13,16H,1,5-6H2,2-4H3/t9-,11+,13+,14+,15-/m0/s1
SMILES:  C=C(C)[C@]12C(=O)C=C3CC[C@H]([C@H](C)[C@@]3(C)[C@H]1O2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL586685
PubChem CID:   177175
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
NPO27746 Taxus mairei Species Taxaceae Eukaryota stem bark n.a. n.a. PMID[11473432]
NPO25366 Sapium indicum Species Euphorbiaceae Eukaryota Fruits n.a. n.a. PMID[12713411]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[16124776]
NPO23756 Aspergillus flavus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16124785]
NPO6645.1 Picea jezoensis var. jezoensis Varieties Pinaceae Eukaryota bark n.a. n.a. PMID[17907781]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[18804027]
NPO6645.1 Picea jezoensis var. jezoensis Varieties Pinaceae Eukaryota bark n.a. n.a. PMID[19646881]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[20233596]
NPO25054 Phaleria macrocarpa Species Thymelaeaceae Eukaryota nut shell n.a. n.a. PMID[23044367]
NPO25252 Nannocystis exedens Species Nannocystaceae Bacteria n.a. n.a. n.a. PMID[24460410]
NPO23756 Aspergillus flavus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24738739]
NPO25311 Guettarda platypoda Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[2553871]
NPO32481 Penicillium copticola Under-species n.a. n.a. n.a. n.a. n.a. PMID[25734623]
NPO23756 Aspergillus flavus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31050424]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[32058711]
NPO23756 Aspergillus flavus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[4207788]
NPO23756 Aspergillus flavus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[4629903]
NPO23756 Aspergillus flavus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[7528269]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[8557595]
NPO27746 Taxus mairei Species Taxaceae Eukaryota Roots n.a. n.a. PMID[8991951]
NPO27746 Taxus mairei Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[9644081]
NPO24278 Pistacia chinensis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24373 Lobelia inflata Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27746 Taxus mairei Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22283 Alhagi maurorum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24852 Helicia nilagirica Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24278 Pistacia chinensis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24373 Lobelia inflata Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24278 Pistacia chinensis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24730 Lactarius deliciosus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24802 Diploprion bifasciatum Species Serranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25277 Seiridium cupressi Species Sporocadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20264 Moonia heterophylla n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25441 Desmodium pulchellu Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15482 Vanderbylia fraxinea Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28460 Achyrocline tomentosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24566 Marasmiellus ramealis Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25389 Allium angulosum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22152 Tecoma undulata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22283 Alhagi maurorum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25492 Botryllus leachi Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25466 Lecanora sulphurella Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23756 Aspergillus flavus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23994 Ormosia macrophylla Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18706 Anemone thalictroides Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23894 Pulicaria insignis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24373 Lobelia inflata Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22618 Psolus eximius Species Psolidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14189 Osmundaria spiralis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25054 Phaleria macrocarpa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25311 Guettarda platypoda Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25366 Sapium indicum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24461 Clusia sandiensis Species Clusiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24852 Helicia nilagirica Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24607 Goniothalamus dolichocarpus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24278 Pistacia chinensis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3721 Achyranthes obtusifolia Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6645.1 Picea jezoensis var. jezoensis Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24882 Erythrophleum chlorostachys Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27746 Taxus mairei Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27390 Vernonia brevifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25252 Nannocystis exedens Species Nannocystaceae Bacteria 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
NPT1229 Cell Line Huh-7 Homo sapiens CC50 > 10000.0 nM PMID[505670]
NPT91 Cell Line KB Homo sapiens IC50 = 17840.0 nM PMID[505671]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 4230.0 nM PMID[505671]
NPT65 Cell Line HepG2 Homo sapiens Survival = 33.2 % PMID[505672]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 = 787.0 nM PMID[505670]
NPT2 Others Unspecified IFI = 5.172 % PMID[505670]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 = 586.0 nM PMID[505670]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 1530.0 nM PMID[505671]

☑ 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 NPC94337 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
0.957 High Similarity NPC112613
0.9362 High Similarity NPC207885
0.9247 High Similarity NPC471916
0.8947 High Similarity NPC264378
0.8866 High Similarity NPC478176
0.88 High Similarity NPC322903
0.8776 High Similarity NPC131366
0.8556 High Similarity NPC60951
0.8544 High Similarity NPC317107
0.8529 High Similarity NPC87335
0.8462 Intermediate Similarity NPC317687
0.8208 Intermediate Similarity NPC159333
0.81 Intermediate Similarity NPC472972
0.809 Intermediate Similarity NPC178852
0.8065 Intermediate Similarity NPC476678
0.8061 Intermediate Similarity NPC316215
0.8056 Intermediate Similarity NPC270478
0.8019 Intermediate Similarity NPC207689
0.8 Intermediate Similarity NPC316598
0.7978 Intermediate Similarity NPC197659
0.7963 Intermediate Similarity NPC238667
0.7959 Intermediate Similarity NPC196227
0.7938 Intermediate Similarity NPC73457
0.7938 Intermediate Similarity NPC186363
0.7938 Intermediate Similarity NPC116726
0.7938 Intermediate Similarity NPC233345
0.7912 Intermediate Similarity NPC172013
0.7879 Intermediate Similarity NPC476245
0.7872 Intermediate Similarity NPC15807
0.7872 Intermediate Similarity NPC79573
0.7849 Intermediate Similarity NPC64600
0.7835 Intermediate Similarity NPC473099
0.7835 Intermediate Similarity NPC475823
0.7835 Intermediate Similarity NPC474209
0.7835 Intermediate Similarity NPC113393
0.7822 Intermediate Similarity NPC216478
0.7818 Intermediate Similarity NPC474518
0.7812 Intermediate Similarity NPC277771
0.7812 Intermediate Similarity NPC307298
0.7802 Intermediate Similarity NPC281138
0.78 Intermediate Similarity NPC202833
0.7789 Intermediate Similarity NPC255143
0.7789 Intermediate Similarity NPC472985
0.7789 Intermediate Similarity NPC472986
0.7778 Intermediate Similarity NPC245972
0.7778 Intermediate Similarity NPC38830
0.7778 Intermediate Similarity NPC196485
0.7767 Intermediate Similarity NPC39996
0.7767 Intermediate Similarity NPC476081
0.7755 Intermediate Similarity NPC472975
0.7755 Intermediate Similarity NPC26865
0.7745 Intermediate Similarity NPC472644
0.7745 Intermediate Similarity NPC46761
0.7745 Intermediate Similarity NPC469551
0.7745 Intermediate Similarity NPC474012
0.7745 Intermediate Similarity NPC476299
0.7742 Intermediate Similarity NPC93590
0.7736 Intermediate Similarity NPC151393
0.7736 Intermediate Similarity NPC476479
0.7732 Intermediate Similarity NPC473100
0.7723 Intermediate Similarity NPC287668
0.7717 Intermediate Similarity NPC148685
0.7717 Intermediate Similarity NPC157895
0.7717 Intermediate Similarity NPC104120
0.7714 Intermediate Similarity NPC128828
0.7714 Intermediate Similarity NPC1679
0.7708 Intermediate Similarity NPC298904
0.7706 Intermediate Similarity NPC477266
0.77 Intermediate Similarity NPC183012
0.77 Intermediate Similarity NPC477437
0.77 Intermediate Similarity NPC477438
0.7692 Intermediate Similarity NPC95899
0.7692 Intermediate Similarity NPC207772
0.7692 Intermediate Similarity NPC473624
0.7685 Intermediate Similarity NPC146945
0.7685 Intermediate Similarity NPC171888
0.7684 Intermediate Similarity NPC96621
0.7677 Intermediate Similarity NPC271652
0.7677 Intermediate Similarity NPC477436
0.7677 Intermediate Similarity NPC477435
0.767 Intermediate Similarity NPC472643
0.767 Intermediate Similarity NPC472637
0.767 Intermediate Similarity NPC470184
0.7664 Intermediate Similarity NPC20192
0.7658 Intermediate Similarity NPC469684
0.7658 Intermediate Similarity NPC243065
0.7653 Intermediate Similarity NPC38952
0.7653 Intermediate Similarity NPC158488
0.7653 Intermediate Similarity NPC134321
0.7653 Intermediate Similarity NPC477684
0.7653 Intermediate Similarity NPC128672
0.7647 Intermediate Similarity NPC212465
0.7647 Intermediate Similarity NPC177232
0.7629 Intermediate Similarity NPC163296
0.7619 Intermediate Similarity NPC296950
0.7619 Intermediate Similarity NPC72255
0.7615 Intermediate Similarity NPC473877
0.7615 Intermediate Similarity NPC277769
0.7609 Intermediate Similarity NPC308038
0.7604 Intermediate Similarity NPC6979
0.7604 Intermediate Similarity NPC94666
0.7604 Intermediate Similarity NPC472974
0.7604 Intermediate Similarity NPC250981
0.7604 Intermediate Similarity NPC179591
0.7604 Intermediate Similarity NPC470955
0.7604 Intermediate Similarity NPC202394
0.76 Intermediate Similarity NPC477439
0.76 Intermediate Similarity NPC250075
0.76 Intermediate Similarity NPC470697
0.7596 Intermediate Similarity NPC137430
0.7596 Intermediate Similarity NPC469606
0.7596 Intermediate Similarity NPC31058
0.7596 Intermediate Similarity NPC273005
0.7582 Intermediate Similarity NPC266193
0.7582 Intermediate Similarity NPC257666
0.7579 Intermediate Similarity NPC40687
0.7576 Intermediate Similarity NPC99380
0.7576 Intermediate Similarity NPC172101
0.7573 Intermediate Similarity NPC112167
0.7573 Intermediate Similarity NPC174314
0.7573 Intermediate Similarity NPC117685
0.7573 Intermediate Similarity NPC54705
0.757 Intermediate Similarity NPC472439
0.757 Intermediate Similarity NPC469916
0.757 Intermediate Similarity NPC89171
0.757 Intermediate Similarity NPC476802
0.7565 Intermediate Similarity NPC120724
0.7553 Intermediate Similarity NPC47450
0.7553 Intermediate Similarity NPC48362
0.7551 Intermediate Similarity NPC472983
0.7551 Intermediate Similarity NPC73995
0.7549 Intermediate Similarity NPC254496
0.7549 Intermediate Similarity NPC273269
0.7549 Intermediate Similarity NPC136781
0.7549 Intermediate Similarity NPC70145
0.7549 Intermediate Similarity NPC285513
0.7549 Intermediate Similarity NPC91695
0.7547 Intermediate Similarity NPC166607
0.7547 Intermediate Similarity NPC111952
0.7547 Intermediate Similarity NPC284365
0.7547 Intermediate Similarity NPC469607
0.7547 Intermediate Similarity NPC85529
0.7547 Intermediate Similarity NPC123726
0.7547 Intermediate Similarity NPC472645
0.7547 Intermediate Similarity NPC32006
0.7545 Intermediate Similarity NPC7921
0.7545 Intermediate Similarity NPC208998
0.7545 Intermediate Similarity NPC477126
0.7545 Intermediate Similarity NPC472926
0.7545 Intermediate Similarity NPC122056
0.7544 Intermediate Similarity NPC67569
0.7526 Intermediate Similarity NPC220930
0.7526 Intermediate Similarity NPC272039
0.7525 Intermediate Similarity NPC271195
0.7525 Intermediate Similarity NPC472485
0.7525 Intermediate Similarity NPC280725
0.7524 Intermediate Similarity NPC275583
0.7524 Intermediate Similarity NPC476848
0.7524 Intermediate Similarity NPC8196
0.7524 Intermediate Similarity NPC320154
0.7524 Intermediate Similarity NPC168575
0.7524 Intermediate Similarity NPC247957
0.7524 Intermediate Similarity NPC194323
0.7524 Intermediate Similarity NPC99266
0.7524 Intermediate Similarity NPC249187
0.7524 Intermediate Similarity NPC159533
0.7524 Intermediate Similarity NPC120321
0.7522 Intermediate Similarity NPC476960
0.75 Intermediate Similarity NPC475922
0.75 Intermediate Similarity NPC12722
0.75 Intermediate Similarity NPC98249
0.75 Intermediate Similarity NPC470615
0.75 Intermediate Similarity NPC77089
0.75 Intermediate Similarity NPC115021
0.75 Intermediate Similarity NPC471412
0.75 Intermediate Similarity NPC53396
0.75 Intermediate Similarity NPC70685
0.75 Intermediate Similarity NPC24651
0.75 Intermediate Similarity NPC470922
0.7478 Intermediate Similarity NPC470265
0.7478 Intermediate Similarity NPC312833
0.7478 Intermediate Similarity NPC23786
0.7477 Intermediate Similarity NPC3316
0.7477 Intermediate Similarity NPC144854
0.7477 Intermediate Similarity NPC143609
0.7477 Intermediate Similarity NPC110496
0.7477 Intermediate Similarity NPC67321
0.7477 Intermediate Similarity NPC266514
0.7477 Intermediate Similarity NPC472925
0.7477 Intermediate Similarity NPC187435
0.7477 Intermediate Similarity NPC473165
0.7477 Intermediate Similarity NPC247069
0.7476 Intermediate Similarity NPC222303
0.7476 Intermediate Similarity NPC109556
0.7475 Intermediate Similarity NPC152467
0.7474 Intermediate Similarity NPC222358
0.7474 Intermediate Similarity NPC169941
0.7474 Intermediate Similarity NPC251475
0.7473 Intermediate Similarity NPC263582
0.7458 Intermediate Similarity NPC477712

  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 NPC94337 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
0.7423 Intermediate Similarity NPD3618 Phase 1
0.7383 Intermediate Similarity NPD5739 Approved
0.7383 Intermediate Similarity NPD6675 Approved
0.7383 Intermediate Similarity NPD6402 Approved
0.7383 Intermediate Similarity NPD7128 Approved
0.7379 Intermediate Similarity NPD4755 Approved
0.7345 Intermediate Similarity NPD7115 Discovery
0.7327 Intermediate Similarity NPD4202 Approved
0.7315 Intermediate Similarity NPD5701 Approved
0.7315 Intermediate Similarity NPD5697 Approved
0.7273 Intermediate Similarity NPD4634 Approved
0.7264 Intermediate Similarity NPD5211 Phase 2
0.7255 Intermediate Similarity NPD5282 Discontinued
0.7248 Intermediate Similarity NPD7320 Approved
0.7248 Intermediate Similarity NPD6899 Approved
0.7248 Intermediate Similarity NPD6011 Approved
0.7248 Intermediate Similarity NPD6881 Approved
0.7238 Intermediate Similarity NPD5285 Approved
0.7238 Intermediate Similarity NPD4696 Approved
0.7238 Intermediate Similarity NPD4700 Approved
0.7238 Intermediate Similarity NPD5286 Approved
0.72 Intermediate Similarity NPD5328 Approved
0.7188 Intermediate Similarity NPD3667 Approved
0.7182 Intermediate Similarity NPD6372 Approved
0.7182 Intermediate Similarity NPD6013 Approved
0.7182 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6012 Approved
0.7182 Intermediate Similarity NPD6014 Approved
0.7182 Intermediate Similarity NPD6373 Approved
0.717 Intermediate Similarity NPD5223 Approved
0.7155 Intermediate Similarity NPD6059 Approved
0.7155 Intermediate Similarity NPD6054 Approved
0.7155 Intermediate Similarity NPD6319 Approved
0.7143 Intermediate Similarity NPD7638 Approved
0.7143 Intermediate Similarity NPD1694 Approved
0.713 Intermediate Similarity NPD5141 Approved
0.7117 Intermediate Similarity NPD7290 Approved
0.7117 Intermediate Similarity NPD6883 Approved
0.7117 Intermediate Similarity NPD7102 Approved
0.7115 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD5221 Approved
0.7115 Intermediate Similarity NPD5222 Approved
0.7115 Intermediate Similarity NPD4697 Phase 3
0.7103 Intermediate Similarity NPD5224 Approved
0.7103 Intermediate Similarity NPD5226 Approved
0.7103 Intermediate Similarity NPD5225 Approved
0.7103 Intermediate Similarity NPD4633 Approved
0.7094 Intermediate Similarity NPD6016 Approved
0.7094 Intermediate Similarity NPD6015 Approved
0.7087 Intermediate Similarity NPD7748 Approved
0.7075 Intermediate Similarity NPD7639 Approved
0.7075 Intermediate Similarity NPD7640 Approved
0.7071 Intermediate Similarity NPD5279 Phase 3
0.7064 Intermediate Similarity NPD6008 Approved
0.7059 Intermediate Similarity NPD6079 Approved
0.7059 Intermediate Similarity NPD7515 Phase 2
0.7054 Intermediate Similarity NPD6847 Approved
0.7054 Intermediate Similarity NPD6649 Approved
0.7054 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6617 Approved
0.7054 Intermediate Similarity NPD8130 Phase 1
0.7054 Intermediate Similarity NPD6650 Approved
0.7054 Intermediate Similarity NPD6869 Approved
0.7048 Intermediate Similarity NPD7902 Approved
0.7048 Intermediate Similarity NPD6083 Phase 2
0.7048 Intermediate Similarity NPD6084 Phase 2
0.7048 Intermediate Similarity NPD5173 Approved
0.7041 Intermediate Similarity NPD3666 Approved
0.7041 Intermediate Similarity NPD4786 Approved
0.7041 Intermediate Similarity NPD3133 Approved
0.7041 Intermediate Similarity NPD3665 Phase 1
0.7037 Intermediate Similarity NPD5174 Approved
0.7037 Intermediate Similarity NPD5175 Approved
0.7037 Intermediate Similarity NPD4754 Approved
0.7034 Intermediate Similarity NPD5988 Approved
0.7034 Intermediate Similarity NPD6370 Approved
0.703 Intermediate Similarity NPD4753 Phase 2
0.7019 Intermediate Similarity NPD5695 Phase 3
0.6991 Remote Similarity NPD6882 Approved
0.6991 Remote Similarity NPD8297 Approved
0.6981 Remote Similarity NPD4225 Approved
0.6979 Remote Similarity NPD4695 Discontinued
0.697 Remote Similarity NPD1696 Phase 3
0.6964 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6937 Remote Similarity NPD5345 Clinical (unspecified phase)
0.693 Remote Similarity NPD4632 Approved
0.6917 Remote Similarity NPD7492 Approved
0.6909 Remote Similarity NPD4767 Approved
0.6909 Remote Similarity NPD4768 Approved
0.69 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6009 Approved
0.6893 Remote Similarity NPD5693 Phase 1
0.6869 Remote Similarity NPD4197 Approved
0.686 Remote Similarity NPD6616 Approved
0.6857 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6833 Remote Similarity NPD7604 Phase 2
0.6833 Remote Similarity NPD8328 Phase 3
0.6827 Remote Similarity NPD6399 Phase 3
0.6827 Remote Similarity NPD5779 Approved
0.6827 Remote Similarity NPD5778 Approved
0.6822 Remote Similarity NPD5696 Approved
0.681 Remote Similarity NPD6274 Approved
0.6807 Remote Similarity NPD5983 Phase 2
0.6804 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6803 Remote Similarity NPD7078 Approved
0.6803 Remote Similarity NPD8293 Discontinued
0.68 Remote Similarity NPD5329 Approved
0.6796 Remote Similarity NPD6698 Approved
0.6796 Remote Similarity NPD46 Approved
0.6786 Remote Similarity NPD4730 Approved
0.6786 Remote Similarity NPD5128 Approved
0.6786 Remote Similarity NPD4729 Approved
0.6765 Remote Similarity NPD6672 Approved
0.6765 Remote Similarity NPD5737 Approved
0.6762 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6762 Remote Similarity NPD7900 Approved
0.6752 Remote Similarity NPD6317 Approved
0.6748 Remote Similarity NPD6033 Approved
0.6748 Remote Similarity NPD7736 Approved
0.6733 Remote Similarity NPD4694 Approved
0.6733 Remote Similarity NPD5690 Phase 2
0.6733 Remote Similarity NPD5280 Approved
0.6731 Remote Similarity NPD6411 Approved
0.6698 Remote Similarity NPD4629 Approved
0.6698 Remote Similarity NPD5210 Approved
0.6697 Remote Similarity NPD5344 Discontinued
0.6696 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6695 Remote Similarity NPD6335 Approved
0.6695 Remote Similarity NPD6314 Approved
0.6695 Remote Similarity NPD6313 Approved
0.6667 Remote Similarity NPD3573 Approved
0.6667 Remote Similarity NPD5248 Approved
0.6667 Remote Similarity NPD5169 Approved
0.6667 Remote Similarity NPD5251 Approved
0.6667 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4221 Approved
0.6667 Remote Similarity NPD5249 Phase 3
0.6667 Remote Similarity NPD5247 Approved
0.6667 Remote Similarity NPD5250 Approved
0.6667 Remote Similarity NPD5135 Approved
0.6667 Remote Similarity NPD4223 Phase 3
0.6667 Remote Similarity NPD6371 Approved
0.6639 Remote Similarity NPD7100 Approved
0.6639 Remote Similarity NPD7101 Approved
0.6609 Remote Similarity NPD5217 Approved
0.6609 Remote Similarity NPD5216 Approved
0.6609 Remote Similarity NPD5215 Approved
0.6609 Remote Similarity NPD5127 Approved
0.6598 Remote Similarity NPD3617 Approved
0.6585 Remote Similarity NPD6336 Discontinued
0.6569 Remote Similarity NPD7146 Approved
0.6569 Remote Similarity NPD7521 Approved
0.6569 Remote Similarity NPD6409 Approved
0.6569 Remote Similarity NPD6684 Approved
0.6569 Remote Similarity NPD5330 Approved
0.6569 Remote Similarity NPD4519 Discontinued
0.6569 Remote Similarity NPD7334 Approved
0.6569 Remote Similarity NPD4623 Approved
0.6549 Remote Similarity NPD6412 Phase 2
0.6538 Remote Similarity NPD6904 Approved
0.6538 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6080 Approved
0.6538 Remote Similarity NPD6101 Approved
0.6538 Remote Similarity NPD6673 Approved
0.6535 Remote Similarity NPD3668 Phase 3
0.6529 Remote Similarity NPD6909 Approved
0.6529 Remote Similarity NPD6908 Approved
0.6525 Remote Similarity NPD6868 Approved
0.65 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6491 Remote Similarity NPD5168 Approved
0.6491 Remote Similarity NPD6686 Approved
0.6486 Remote Similarity NPD7632 Discontinued
0.6476 Remote Similarity NPD5692 Phase 3
0.6476 Remote Similarity NPD5785 Approved
0.6471 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6455 Remote Similarity NPD6648 Approved
0.6442 Remote Similarity NPD6903 Approved
0.6442 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6441 Remote Similarity NPD5167 Approved
0.6429 Remote Similarity NPD7319 Approved
0.6415 Remote Similarity NPD5694 Approved
0.6415 Remote Similarity NPD6050 Approved
0.641 Remote Similarity NPD6053 Discontinued
0.6408 Remote Similarity NPD6098 Approved
0.6408 Remote Similarity NPD4690 Approved
0.6408 Remote Similarity NPD5205 Approved
0.6408 Remote Similarity NPD4138 Approved
0.6408 Remote Similarity NPD4693 Phase 3
0.6408 Remote Similarity NPD4688 Approved
0.6408 Remote Similarity NPD4689 Approved
0.6404 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6393 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6389 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6381 Remote Similarity NPD1695 Approved
0.6381 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6373 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7645 Phase 2
0.6364 Remote Similarity NPD4522 Approved
0.6355 Remote Similarity NPD5133 Approved
0.632 Remote Similarity NPD7507 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