Structure

Physi-Chem Properties

Molecular Weight:  236.18
Volume:  263.191
LogP:  2.035
LogD:  2.823
LogS:  -3.349
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.687
Synthetic Accessibility Score:  4.603
Fsp3:  0.733
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:  -4.607
MDCK Permeability:  1.6691104974597692e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.025
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.898
30% Bioavailability (F30%):  0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.853
Plasma Protein Binding (PPB):  53.37921142578125%
Volume Distribution (VD):  1.525
Pgp-substrate:  53.20851135253906%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.562
CYP2C19-inhibitor:  0.042
CYP2C19-substrate:  0.806
CYP2C9-inhibitor:  0.035
CYP2C9-substrate:  0.185
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.387
CYP3A4-inhibitor:  0.073
CYP3A4-substrate:  0.254

ADMET: Excretion

Clearance (CL):  6.308
Half-life (T1/2):  0.25

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.257
Drug-inuced Liver Injury (DILI):  0.105
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.859
Maximum Recommended Daily Dose:  0.976
Skin Sensitization:  0.169
Carcinogencity:  0.718
Eye Corrosion:  0.428
Eye Irritation:  0.913
Respiratory Toxicity:  0.958

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  Natural Product: NPC245795

Natural Product ID:  NPC245795
Common Name*:   Rel-Oxyphyllanene E
IUPAC Name:   (2R,4aR,7S,8aR)-4a-methyl-8-methylidene-2-prop-1-en-2-yl-3,4,5,6,7,8a-hexahydro-1H-naphthalene-2,7-diol
Synonyms:   Rel-Oxyphyllanene E
Standard InCHIKey:  HMYKTCAHZPOVHL-BYNSBNAKSA-N
Standard InCHI:  InChI=1S/C15H24O2/c1-10(2)15(17)8-7-14(4)6-5-13(16)11(3)12(14)9-15/h12-13,16-17H,1,3,5-9H2,2,4H3/t12-,13-,14+,15+/m0/s1
SMILES:  C=C(C)[C@]1(CC[C@@]2(C)CC[C@@H](C(=C)[C@@H]2C1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1949798
PubChem CID:   57400339
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(81)85171-0]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota Whole plant n.a. n.a. PMID[11141121]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[11514174]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota fruit Hainan Island, China 1998 PMID[12398545]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[18057725]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. PMID[18293903]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. PMID[19432411]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[22277277]
NPO25106 Arnica parryi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[23583435]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. PMID[24669201]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[25757283]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[9157192]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota stem bark n.a. n.a. PMID[9157192]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23288 Justicia betonica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18045 Holothuria atra Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27277 Stenocarpella maydis Species Diaporthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24937 Callicarpa acuminata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24754 Tsitsikamma favus Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25130 Hylotrupes bajulus Species Cerambycidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24813 Agardhiella tenera Species Solieriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25106 Arnica parryi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23750 Escontria chiotilla Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24406 Rhizophora tagal Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24688 Streptomyces ramocissimus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24659 Eremurus chinensis Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13455 Hemiselmis virescens Species Hemiselmidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23149 Callistemon coccineus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24874 Croton geayi Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23657 Ophiocordyceps heteropoda Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27093 Kniphofia foliosa Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23837 Rubus laciniatus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19716 Uvaria lucida Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18875 Aconitum contortum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25226 Kalanchoe spathulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21483 0nomuraea dietziae Species Streptosporangiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24969 Ageratum mexicanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24268 Pteryxia terebinthina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24589 Grindelia discoidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23288 Justicia betonica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24118 Buxus hildebrandtii Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21799 Bacillus litoralis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22924 Bombus terrestris Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25031 Petunia nyctaginiflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24021 Eucryphia cordifolia Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO25068 Zebrina pendula Species Enidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17445 Streptomyces corchorusii Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO23660 Alpinia zerumbet Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23375 Hypericum reptans Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24456 Salvia lavandulifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21242 Neolitsea villosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28259 Viguiera pinnatilobata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24493 Echinacea simulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24191 Drypetes tessmanniana Species Putranjivaceae 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 13.52 ug.mL-1 PMID[449630]

☑ 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 NPC245795 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
0.9531 High Similarity NPC269077
0.9531 High Similarity NPC253303
0.9394 High Similarity NPC283316
0.9385 High Similarity NPC276616
0.9365 High Similarity NPC68656
0.9219 High Similarity NPC258595
0.9091 High Similarity NPC266578
0.9077 High Similarity NPC475897
0.9062 High Similarity NPC101128
0.8955 High Similarity NPC9942
0.8955 High Similarity NPC234511
0.8939 High Similarity NPC139207
0.8939 High Similarity NPC185874
0.8841 High Similarity NPC95165
0.8806 High Similarity NPC244790
0.8769 High Similarity NPC144650
0.8714 High Similarity NPC306727
0.8636 High Similarity NPC60837
0.8636 High Similarity NPC282619
0.8636 High Similarity NPC2728
0.8636 High Similarity NPC172613
0.8636 High Similarity NPC11555
0.8636 High Similarity NPC208198
0.8592 High Similarity NPC32832
0.8507 High Similarity NPC476406
0.8507 High Similarity NPC473929
0.8493 Intermediate Similarity NPC472499
0.8493 Intermediate Similarity NPC472500
0.8472 Intermediate Similarity NPC253190
0.8472 Intermediate Similarity NPC63958
0.8451 Intermediate Similarity NPC308440
0.8451 Intermediate Similarity NPC476366
0.8451 Intermediate Similarity NPC201048
0.8451 Intermediate Similarity NPC476736
0.8451 Intermediate Similarity NPC472503
0.8429 Intermediate Similarity NPC167706
0.8382 Intermediate Similarity NPC88454
0.8382 Intermediate Similarity NPC101307
0.8382 Intermediate Similarity NPC117607
0.8378 Intermediate Similarity NPC24504
0.8378 Intermediate Similarity NPC476316
0.8356 Intermediate Similarity NPC470711
0.8356 Intermediate Similarity NPC470758
0.8333 Intermediate Similarity NPC185536
0.8333 Intermediate Similarity NPC144075
0.8281 Intermediate Similarity NPC474769
0.8281 Intermediate Similarity NPC189290
0.8267 Intermediate Similarity NPC47149
0.8261 Intermediate Similarity NPC96484
0.8254 Intermediate Similarity NPC264779
0.8243 Intermediate Similarity NPC301707
0.8243 Intermediate Similarity NPC472342
0.8243 Intermediate Similarity NPC472502
0.8243 Intermediate Similarity NPC472501
0.8243 Intermediate Similarity NPC475
0.8243 Intermediate Similarity NPC31828
0.8219 Intermediate Similarity NPC265588
0.8219 Intermediate Similarity NPC470749
0.8219 Intermediate Similarity NPC38141
0.8169 Intermediate Similarity NPC164022
0.8169 Intermediate Similarity NPC23954
0.8158 Intermediate Similarity NPC249423
0.8158 Intermediate Similarity NPC476646
0.8143 Intermediate Similarity NPC210323
0.8108 Intermediate Similarity NPC331618
0.8108 Intermediate Similarity NPC202540
0.8108 Intermediate Similarity NPC212241
0.8108 Intermediate Similarity NPC260301
0.8108 Intermediate Similarity NPC119355
0.8108 Intermediate Similarity NPC471798
0.8108 Intermediate Similarity NPC257191
0.8108 Intermediate Similarity NPC248830
0.8108 Intermediate Similarity NPC307336
0.8108 Intermediate Similarity NPC138502
0.8088 Intermediate Similarity NPC300442
0.8082 Intermediate Similarity NPC3403
0.8082 Intermediate Similarity NPC103822
0.8056 Intermediate Similarity NPC211009
0.8056 Intermediate Similarity NPC265485
0.8056 Intermediate Similarity NPC220939
0.8056 Intermediate Similarity NPC472506
0.8028 Intermediate Similarity NPC92801
0.8028 Intermediate Similarity NPC34834
0.8028 Intermediate Similarity NPC45296
0.8026 Intermediate Similarity NPC96362
0.8 Intermediate Similarity NPC2648
0.8 Intermediate Similarity NPC471238
0.8 Intermediate Similarity NPC477817
0.8 Intermediate Similarity NPC477819
0.7975 Intermediate Similarity NPC164424
0.7973 Intermediate Similarity NPC91573
0.7945 Intermediate Similarity NPC469534
0.7945 Intermediate Similarity NPC469593
0.7945 Intermediate Similarity NPC469533
0.7941 Intermediate Similarity NPC219940
0.7922 Intermediate Similarity NPC23852
0.7922 Intermediate Similarity NPC209620
0.7917 Intermediate Similarity NPC164045
0.7917 Intermediate Similarity NPC301226
0.7917 Intermediate Similarity NPC471272
0.7917 Intermediate Similarity NPC111234
0.7917 Intermediate Similarity NPC477792
0.791 Intermediate Similarity NPC41160
0.7895 Intermediate Similarity NPC30986
0.7895 Intermediate Similarity NPC72755
0.7895 Intermediate Similarity NPC472742
0.7895 Intermediate Similarity NPC209430
0.7895 Intermediate Similarity NPC475727
0.7895 Intermediate Similarity NPC472463
0.7895 Intermediate Similarity NPC476367
0.7895 Intermediate Similarity NPC80297
0.7895 Intermediate Similarity NPC116119
0.7887 Intermediate Similarity NPC474248
0.7875 Intermediate Similarity NPC261266
0.7875 Intermediate Similarity NPC6391
0.7867 Intermediate Similarity NPC130136
0.7867 Intermediate Similarity NPC91594
0.7857 Intermediate Similarity NPC74885
0.7857 Intermediate Similarity NPC308522
0.7857 Intermediate Similarity NPC69649
0.7857 Intermediate Similarity NPC68703
0.7848 Intermediate Similarity NPC256567
0.7838 Intermediate Similarity NPC104387
0.7838 Intermediate Similarity NPC70982
0.7838 Intermediate Similarity NPC178383
0.7838 Intermediate Similarity NPC231256
0.7838 Intermediate Similarity NPC212879
0.7838 Intermediate Similarity NPC240235
0.7838 Intermediate Similarity NPC230704
0.7826 Intermediate Similarity NPC64123
0.7821 Intermediate Similarity NPC155521
0.7821 Intermediate Similarity NPC50964
0.7821 Intermediate Similarity NPC218616
0.7821 Intermediate Similarity NPC296701
0.7808 Intermediate Similarity NPC68443
0.7808 Intermediate Similarity NPC182717
0.7808 Intermediate Similarity NPC195489
0.7808 Intermediate Similarity NPC471799
0.7792 Intermediate Similarity NPC78545
0.7792 Intermediate Similarity NPC209944
0.7792 Intermediate Similarity NPC164840
0.7792 Intermediate Similarity NPC295131
0.7792 Intermediate Similarity NPC475679
0.7792 Intermediate Similarity NPC241290
0.7792 Intermediate Similarity NPC71535
0.7778 Intermediate Similarity NPC476948
0.7763 Intermediate Similarity NPC83351
0.7763 Intermediate Similarity NPC474216
0.7763 Intermediate Similarity NPC87604
0.7763 Intermediate Similarity NPC167891
0.7763 Intermediate Similarity NPC11908
0.7763 Intermediate Similarity NPC42853
0.7763 Intermediate Similarity NPC52755
0.7763 Intermediate Similarity NPC476314
0.7763 Intermediate Similarity NPC285761
0.775 Intermediate Similarity NPC470360
0.7746 Intermediate Similarity NPC208999
0.7733 Intermediate Similarity NPC78067
0.7733 Intermediate Similarity NPC278091
0.7733 Intermediate Similarity NPC86305
0.7733 Intermediate Similarity NPC93662
0.7733 Intermediate Similarity NPC14112
0.7733 Intermediate Similarity NPC470766
0.7722 Intermediate Similarity NPC211135
0.7722 Intermediate Similarity NPC470929
0.7722 Intermediate Similarity NPC216420
0.7722 Intermediate Similarity NPC243347
0.7722 Intermediate Similarity NPC232023
0.7722 Intermediate Similarity NPC85095
0.7722 Intermediate Similarity NPC477978
0.7714 Intermediate Similarity NPC202017
0.7703 Intermediate Similarity NPC91858
0.7703 Intermediate Similarity NPC243342
0.7703 Intermediate Similarity NPC196358
0.7703 Intermediate Similarity NPC254509
0.7703 Intermediate Similarity NPC62657
0.7703 Intermediate Similarity NPC5046
0.7703 Intermediate Similarity NPC192638
0.7703 Intermediate Similarity NPC471797
0.7703 Intermediate Similarity NPC49168
0.7703 Intermediate Similarity NPC477138
0.7703 Intermediate Similarity NPC25511
0.7703 Intermediate Similarity NPC100334
0.7703 Intermediate Similarity NPC145552
0.7692 Intermediate Similarity NPC242350
0.7692 Intermediate Similarity NPC264245
0.7692 Intermediate Similarity NPC157655
0.7692 Intermediate Similarity NPC24443
0.7692 Intermediate Similarity NPC39068
0.7683 Intermediate Similarity NPC474668
0.7683 Intermediate Similarity NPC133588
0.7681 Intermediate Similarity NPC323424
0.7681 Intermediate Similarity NPC96793
0.7671 Intermediate Similarity NPC469343
0.7671 Intermediate Similarity NPC471268
0.7671 Intermediate Similarity NPC471271
0.7671 Intermediate Similarity NPC242001
0.7671 Intermediate Similarity NPC242992
0.7662 Intermediate Similarity NPC291379
0.7662 Intermediate Similarity NPC49627

  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 NPC245795 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
0.7564 Intermediate Similarity NPD7525 Registered
0.7564 Intermediate Similarity NPD6931 Approved
0.7564 Intermediate Similarity NPD6930 Phase 2
0.7561 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD6929 Approved
0.7436 Intermediate Similarity NPD7645 Phase 2
0.7368 Intermediate Similarity NPD7339 Approved
0.7368 Intermediate Similarity NPD6942 Approved
0.7284 Intermediate Similarity NPD6695 Phase 3
0.7237 Intermediate Similarity NPD6924 Approved
0.7237 Intermediate Similarity NPD6926 Approved
0.7195 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD6925 Approved
0.7179 Intermediate Similarity NPD5776 Phase 2
0.7143 Intermediate Similarity NPD8264 Approved
0.7125 Intermediate Similarity NPD7332 Phase 2
0.7125 Intermediate Similarity NPD7514 Phase 3
0.7108 Intermediate Similarity NPD6893 Approved
0.7089 Intermediate Similarity NPD7145 Approved
0.7051 Intermediate Similarity NPD6933 Approved
0.7037 Intermediate Similarity NPD6898 Phase 1
0.6962 Remote Similarity NPD6932 Approved
0.6951 Remote Similarity NPD3667 Approved
0.6941 Remote Similarity NPD7750 Discontinued
0.6941 Remote Similarity NPD7524 Approved
0.6914 Remote Similarity NPD7509 Discontinued
0.6914 Remote Similarity NPD4748 Discontinued
0.6905 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6901 Remote Similarity NPD368 Approved
0.6875 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6829 Remote Similarity NPD6902 Approved
0.6824 Remote Similarity NPD3618 Phase 1
0.679 Remote Similarity NPD6683 Phase 2
0.6786 Remote Similarity NPD4786 Approved
0.6753 Remote Similarity NPD4243 Approved
0.6753 Remote Similarity NPD7150 Approved
0.6753 Remote Similarity NPD7152 Approved
0.6753 Remote Similarity NPD7151 Approved
0.6711 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6711 Remote Similarity NPD6923 Approved
0.6711 Remote Similarity NPD6922 Approved
0.6667 Remote Similarity NPD388 Approved
0.6667 Remote Similarity NPD386 Approved
0.6667 Remote Similarity NPD4788 Approved
0.6667 Remote Similarity NPD7640 Approved
0.6667 Remote Similarity NPD7639 Approved
0.6629 Remote Similarity NPD7087 Discontinued
0.6623 Remote Similarity NPD7143 Approved
0.6623 Remote Similarity NPD7144 Approved
0.6623 Remote Similarity NPD4787 Phase 1
0.6591 Remote Similarity NPD5328 Approved
0.6588 Remote Similarity NPD3666 Approved
0.6588 Remote Similarity NPD3665 Phase 1
0.6588 Remote Similarity NPD3133 Approved
0.6582 Remote Similarity NPD4784 Approved
0.6582 Remote Similarity NPD4785 Approved
0.6562 Remote Similarity NPD385 Approved
0.6562 Remote Similarity NPD384 Approved
0.6559 Remote Similarity NPD7638 Approved
0.6556 Remote Similarity NPD4202 Approved
0.6522 Remote Similarity NPD342 Phase 1
0.65 Remote Similarity NPD4190 Phase 3
0.65 Remote Similarity NPD3703 Phase 2
0.65 Remote Similarity NPD5275 Approved
0.6494 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6494 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6486 Remote Similarity NPD371 Approved
0.6444 Remote Similarity NPD6079 Approved
0.6444 Remote Similarity NPD7515 Phase 2
0.6386 Remote Similarity NPD4195 Approved
0.6354 Remote Similarity NPD5211 Phase 2
0.6329 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6329 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6301 Remote Similarity NPD1145 Discontinued
0.6277 Remote Similarity NPD4755 Approved
0.6265 Remote Similarity NPD6118 Approved
0.6265 Remote Similarity NPD6114 Approved
0.6265 Remote Similarity NPD6115 Approved
0.6265 Remote Similarity NPD6697 Approved
0.6264 Remote Similarity NPD8035 Phase 2
0.6264 Remote Similarity NPD8034 Phase 2
0.625 Remote Similarity NPD4732 Discontinued
0.625 Remote Similarity NPD4519 Discontinued
0.625 Remote Similarity NPD4623 Approved
0.6224 Remote Similarity NPD5141 Approved
0.6222 Remote Similarity NPD4753 Phase 2
0.6211 Remote Similarity NPD4225 Approved
0.6207 Remote Similarity NPD3668 Phase 3
0.6186 Remote Similarity NPD7632 Discontinued
0.6184 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6173 Remote Similarity NPD6113 Clinical (unspecified phase)
0.617 Remote Similarity NPD5220 Clinical (unspecified phase)
0.617 Remote Similarity NPD4697 Phase 3
0.617 Remote Similarity NPD5221 Approved
0.617 Remote Similarity NPD5222 Approved
0.6163 Remote Similarity NPD4223 Phase 3
0.6163 Remote Similarity NPD4221 Approved
0.6154 Remote Similarity NPD7136 Phase 2
0.6146 Remote Similarity NPD4700 Approved
0.6146 Remote Similarity NPD5286 Approved
0.6146 Remote Similarity NPD4696 Approved
0.6146 Remote Similarity NPD5285 Approved
0.6136 Remote Similarity NPD1696 Phase 3
0.6129 Remote Similarity NPD7748 Approved
0.6118 Remote Similarity NPD6928 Phase 2
0.6105 Remote Similarity NPD5173 Approved
0.6087 Remote Similarity NPD7637 Suspended
0.6082 Remote Similarity NPD5223 Approved
0.6076 Remote Similarity NPD3698 Phase 2
0.6067 Remote Similarity NPD5279 Phase 3
0.6042 Remote Similarity NPD5290 Discontinued
0.6024 Remote Similarity NPD6117 Approved
0.6023 Remote Similarity NPD4197 Approved
0.6022 Remote Similarity NPD6399 Phase 3
0.602 Remote Similarity NPD4633 Approved
0.602 Remote Similarity NPD5224 Approved
0.602 Remote Similarity NPD5225 Approved
0.602 Remote Similarity NPD5226 Approved
0.6 Remote Similarity NPD4244 Approved
0.6 Remote Similarity NPD4245 Approved
0.596 Remote Similarity NPD5175 Approved
0.596 Remote Similarity NPD4754 Approved
0.596 Remote Similarity NPD5174 Approved
0.5955 Remote Similarity NPD5329 Approved
0.5952 Remote Similarity NPD6116 Phase 1
0.5949 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5949 Remote Similarity NPD5360 Phase 3
0.5938 Remote Similarity NPD7902 Approved
0.593 Remote Similarity NPD4695 Discontinued
0.5922 Remote Similarity NPD4634 Approved
0.5918 Remote Similarity NPD4159 Approved
0.5905 Remote Similarity NPD8133 Approved
0.5895 Remote Similarity NPD5210 Approved
0.5895 Remote Similarity NPD4629 Approved
0.5889 Remote Similarity NPD4688 Approved
0.5889 Remote Similarity NPD5205 Approved
0.5889 Remote Similarity NPD4138 Approved
0.5889 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5889 Remote Similarity NPD4689 Approved
0.5889 Remote Similarity NPD4690 Approved
0.5889 Remote Similarity NPD4693 Phase 3
0.5882 Remote Similarity NPD3671 Phase 1
0.5882 Remote Similarity NPD3617 Approved
0.5882 Remote Similarity NPD5345 Clinical (unspecified phase)
0.587 Remote Similarity NPD6051 Approved
0.5851 Remote Similarity NPD5778 Approved
0.5851 Remote Similarity NPD5779 Approved
0.5842 Remote Similarity NPD6402 Approved
0.5842 Remote Similarity NPD4767 Approved
0.5842 Remote Similarity NPD4768 Approved
0.5842 Remote Similarity NPD7128 Approved
0.5842 Remote Similarity NPD6675 Approved
0.5842 Remote Similarity NPD5739 Approved
0.5825 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5802 Remote Similarity NPD4789 Approved
0.5784 Remote Similarity NPD5701 Approved
0.5784 Remote Similarity NPD5697 Approved
0.5783 Remote Similarity NPD1810 Approved
0.5783 Remote Similarity NPD1811 Approved
0.5773 Remote Similarity NPD6084 Phase 2
0.5773 Remote Similarity NPD6083 Phase 2
0.5761 Remote Similarity NPD4722 Approved
0.5761 Remote Similarity NPD4723 Approved
0.5758 Remote Similarity NPD5344 Discontinued
0.5755 Remote Similarity NPD4632 Approved
0.5753 Remote Similarity NPD4219 Approved
0.575 Remote Similarity NPD6705 Phase 1
0.5732 Remote Similarity NPD4758 Discontinued
0.5728 Remote Similarity NPD6899 Approved
0.5728 Remote Similarity NPD4730 Approved
0.5728 Remote Similarity NPD6011 Approved
0.5728 Remote Similarity NPD6881 Approved
0.5728 Remote Similarity NPD4729 Approved
0.5728 Remote Similarity NPD5128 Approved
0.5728 Remote Similarity NPD7320 Approved
0.5714 Remote Similarity NPD7146 Approved
0.5714 Remote Similarity NPD5690 Phase 2
0.5714 Remote Similarity NPD6409 Approved
0.5714 Remote Similarity NPD4694 Approved
0.5714 Remote Similarity NPD7521 Approved
0.5714 Remote Similarity NPD6684 Approved
0.5714 Remote Similarity NPD5330 Approved
0.5714 Remote Similarity NPD7334 Approved
0.5714 Remote Similarity NPD5280 Approved
0.5692 Remote Similarity NPD1799 Clinical (unspecified phase)
0.5688 Remote Similarity NPD7328 Approved
0.5688 Remote Similarity NPD7327 Approved
0.5682 Remote Similarity NPD4139 Approved
0.5682 Remote Similarity NPD4692 Approved
0.5673 Remote Similarity NPD6373 Approved
0.5673 Remote Similarity NPD6012 Approved
0.5673 Remote Similarity NPD6372 Approved
0.5673 Remote Similarity NPD6013 Approved
0.5673 Remote Similarity NPD6014 Approved
0.5652 Remote Similarity NPD9410 Clinical (unspecified phase)
0.5652 Remote Similarity NPD3573 Approved
0.5638 Remote Similarity NPD3168 Discontinued
0.5636 Remote Similarity NPD7516 Approved
0.5631 Remote Similarity NPD6412 Phase 2

  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