Structure

Physi-Chem Properties

Molecular Weight:  306.26
Volume:  337.831
LogP:  4.498
LogD:  4.184
LogS:  -4.722
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.764
Synthetic Accessibility Score:  5.532
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.102
MDCK Permeability:  2.0904695702483878e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.093
30% Bioavailability (F30%):  0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.102
Plasma Protein Binding (PPB):  96.66407012939453%
Volume Distribution (VD):  1.344
Pgp-substrate:  2.77836012840271%

ADMET: Metabolism

CYP1A2-inhibitor:  0.036
CYP1A2-substrate:  0.373
CYP2C19-inhibitor:  0.044
CYP2C19-substrate:  0.828
CYP2C9-inhibitor:  0.19
CYP2C9-substrate:  0.577
CYP2D6-inhibitor:  0.033
CYP2D6-substrate:  0.602
CYP3A4-inhibitor:  0.752
CYP3A4-substrate:  0.153

ADMET: Excretion

Clearance (CL):  5.461
Half-life (T1/2):  0.333

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.304
Drug-inuced Liver Injury (DILI):  0.022
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.025
Maximum Recommended Daily Dose:  0.718
Skin Sensitization:  0.887
Carcinogencity:  0.013
Eye Corrosion:  0.929
Eye Irritation:  0.87
Respiratory Toxicity:  0.921

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  Natural Product: NPC243469

Natural Product ID:  NPC243469
Common Name*:   LCYWCTWYVKIBSA-URTLRTLISA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  LCYWCTWYVKIBSA-URTLRTLISA-N
Standard InCHI:  InChI=1S/C20H34O2/c1-17(2)8-4-9-18(3)15(17)7-10-19-11-14(5-6-16(18)19)20(22,12-19)13-21/h14-16,21-22H,4-13H2,1-3H3/t14-,15-,16+,18-,19+,20+/m1/s1
SMILES:  OC[C@@]1(O)C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@H](CC2)C(C)(C)CCC1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3357413
PubChem CID:   13816761
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. stem wood n.a. DOI[10.1021/np100247r]
NPO19242 Eucalyptus albens Species Myrtaceae Eukaryota flowers n.a. n.a. PMID[10075775]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10395501]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10425140]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[10479331]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seeds n.a. n.a. PMID[15387664]
NPO6333 Annona glabra Species Annonaceae Eukaryota Fruits n.a. n.a. PMID[15568797]
NPO19083 Alstonia angustiloba Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[18524603]
NPO6333 Annona glabra Species Annonaceae Eukaryota stem Taipei Botanical Garden, Taipei, Taiwan, China 2006-MAR PMID[20828184]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. stem n.a. PMID[21443171]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO6333 Annona glabra Species Annonaceae Eukaryota fruits n.a. n.a. PMID[25499882]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota leaves and branches San Antonio, Texas 2004-JUN PMID[25685941]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota leaves and branches n.a. n.a. PMID[25685941]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[26238319]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota Roots n.a. n.a. PMID[29924604]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. Suriname rainforest n.a. PMID[9428162]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9584397]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9599260]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14233 Ormosia dasycarpa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24402.1 Coffea liberica var. dewevrei Varieties Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11967 Delphinium giraldii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12870 Curcuma aeruginosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14233 Ormosia dasycarpa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19170 Lasianthaea podocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19083 Alstonia angustiloba Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16981 Gutierrezia dracunculoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19572 Pellacalyx axillaris Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11646 Morella pensylvanica Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15127 Senecio congestus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11967 Delphinium giraldii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12914 Sarcophyton flexuosum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12223 Stellaria media Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18262 Aspergillus microcysticus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18424 Selinum libanotis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29531 Lupinus cosentinii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18927 Clinacanthus nutans Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17354 Micromonospora echinospora Species Micromonosporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17230 Psidium acutangulum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19709 Pseudocyphellaria australiensis Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4679 Hedysarum gmelini Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19242 Eucalyptus albens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19371 Costasiella ocellifera Species Costasiellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18348 Crotalaria stolzii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9906 Zephyranthes flava Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18048 Phlomis crinita Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8172 Emericellopsis minima Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17114 Streptomyces melanogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11081 Baccharis grandicapitulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17630 Helenium integrifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18533 Delisea elegans Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16135 Pestalotiopsis oenotherae Species Sporocadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO968 Artemisia pectinata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17499 Bursera kerberi Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5455 Euploca racemosa Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25370 Botrychium ternatum Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24402.1 Coffea liberica var. dewevrei Varieties Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15802 Papaver pseudocanescens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16325 Sideritis dasygnaphala Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29450 Streptomyces parvisporogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18169 Creosphaeria sassafras Species Xylariaceae 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 = 17060.0 nM PMID[459452]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 70.4 % PMID[459452]

☑ 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 NPC243469 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC475943
1.0 High Similarity NPC190827
0.9677 High Similarity NPC63190
0.9 High Similarity NPC476735
0.8955 High Similarity NPC153719
0.8889 High Similarity NPC159654
0.8889 High Similarity NPC167995
0.8889 High Similarity NPC281540
0.8889 High Similarity NPC118937
0.8824 High Similarity NPC472854
0.8788 High Similarity NPC299948
0.8788 High Similarity NPC241085
0.8788 High Similarity NPC470830
0.8788 High Similarity NPC107919
0.875 High Similarity NPC472946
0.873 High Similarity NPC114891
0.8696 High Similarity NPC27349
0.8696 High Similarity NPC317242
0.8696 High Similarity NPC24014
0.8676 High Similarity NPC470610
0.8657 High Similarity NPC231945
0.8615 High Similarity NPC44122
0.8571 High Similarity NPC470145
0.8571 High Similarity NPC71460
0.8571 High Similarity NPC218585
0.8571 High Similarity NPC148174
0.8571 High Similarity NPC163597
0.8551 High Similarity NPC48795
0.8507 High Similarity NPC99264
0.8507 High Similarity NPC477820
0.8485 Intermediate Similarity NPC48079
0.8451 Intermediate Similarity NPC105208
0.8451 Intermediate Similarity NPC180199
0.8451 Intermediate Similarity NPC477919
0.8451 Intermediate Similarity NPC185915
0.8451 Intermediate Similarity NPC192046
0.8451 Intermediate Similarity NPC128951
0.8451 Intermediate Similarity NPC477227
0.8451 Intermediate Similarity NPC302578
0.8451 Intermediate Similarity NPC171658
0.8406 Intermediate Similarity NPC473238
0.8406 Intermediate Similarity NPC472341
0.8387 Intermediate Similarity NPC162685
0.8382 Intermediate Similarity NPC251201
0.8382 Intermediate Similarity NPC232925
0.8382 Intermediate Similarity NPC63588
0.8358 Intermediate Similarity NPC472741
0.8333 Intermediate Similarity NPC476732
0.8333 Intermediate Similarity NPC142712
0.8333 Intermediate Similarity NPC199965
0.8333 Intermediate Similarity NPC67657
0.8333 Intermediate Similarity NPC18857
0.8308 Intermediate Similarity NPC69149
0.8286 Intermediate Similarity NPC228994
0.8286 Intermediate Similarity NPC192501
0.8286 Intermediate Similarity NPC477508
0.8286 Intermediate Similarity NPC10476
0.8286 Intermediate Similarity NPC304499
0.8261 Intermediate Similarity NPC131506
0.8261 Intermediate Similarity NPC157777
0.8235 Intermediate Similarity NPC66407
0.8235 Intermediate Similarity NPC254037
0.8235 Intermediate Similarity NPC129829
0.8219 Intermediate Similarity NPC287452
0.8209 Intermediate Similarity NPC473230
0.8209 Intermediate Similarity NPC475884
0.8182 Intermediate Similarity NPC260116
0.8182 Intermediate Similarity NPC473276
0.8182 Intermediate Similarity NPC41577
0.8182 Intermediate Similarity NPC474380
0.8169 Intermediate Similarity NPC158208
0.8169 Intermediate Similarity NPC91387
0.8169 Intermediate Similarity NPC196136
0.8169 Intermediate Similarity NPC231680
0.8169 Intermediate Similarity NPC243027
0.8169 Intermediate Similarity NPC270306
0.8154 Intermediate Similarity NPC249078
0.8154 Intermediate Similarity NPC236099
0.8154 Intermediate Similarity NPC209686
0.8143 Intermediate Similarity NPC310766
0.8116 Intermediate Similarity NPC192192
0.8116 Intermediate Similarity NPC282454
0.8088 Intermediate Similarity NPC474756
0.8065 Intermediate Similarity NPC3025
0.8056 Intermediate Similarity NPC91573
0.8 Intermediate Similarity NPC8004
0.8 Intermediate Similarity NPC473279
0.8 Intermediate Similarity NPC127283
0.8 Intermediate Similarity NPC195530
0.8 Intermediate Similarity NPC1340
0.8 Intermediate Similarity NPC109457
0.8 Intermediate Similarity NPC187471
0.8 Intermediate Similarity NPC157422
0.8 Intermediate Similarity NPC470071
0.8 Intermediate Similarity NPC252182
0.8 Intermediate Similarity NPC100586
0.8 Intermediate Similarity NPC127094
0.7971 Intermediate Similarity NPC321732
0.7971 Intermediate Similarity NPC324607
0.7945 Intermediate Similarity NPC476233
0.7945 Intermediate Similarity NPC11907
0.7945 Intermediate Similarity NPC64081
0.7945 Intermediate Similarity NPC133596
0.7945 Intermediate Similarity NPC264602
0.7945 Intermediate Similarity NPC474574
0.7937 Intermediate Similarity NPC135438
0.7895 Intermediate Similarity NPC317066
0.7895 Intermediate Similarity NPC475388
0.7895 Intermediate Similarity NPC477935
0.7887 Intermediate Similarity NPC472506
0.7867 Intermediate Similarity NPC472853
0.7867 Intermediate Similarity NPC470609
0.7838 Intermediate Similarity NPC147993
0.7838 Intermediate Similarity NPC471045
0.7838 Intermediate Similarity NPC42853
0.7826 Intermediate Similarity NPC475893
0.7808 Intermediate Similarity NPC477601
0.7808 Intermediate Similarity NPC473916
0.7808 Intermediate Similarity NPC477602
0.7792 Intermediate Similarity NPC478054
0.7778 Intermediate Similarity NPC472945
0.7778 Intermediate Similarity NPC472944
0.7778 Intermediate Similarity NPC476736
0.7763 Intermediate Similarity NPC77311
0.7746 Intermediate Similarity NPC156277
0.7746 Intermediate Similarity NPC164045
0.7746 Intermediate Similarity NPC58057
0.7746 Intermediate Similarity NPC478103
0.7746 Intermediate Similarity NPC151018
0.7746 Intermediate Similarity NPC320549
0.7733 Intermediate Similarity NPC49599
0.7733 Intermediate Similarity NPC477282
0.7733 Intermediate Similarity NPC269333
0.7733 Intermediate Similarity NPC49627
0.7733 Intermediate Similarity NPC81074
0.7714 Intermediate Similarity NPC469941
0.7714 Intermediate Similarity NPC319671
0.7714 Intermediate Similarity NPC252032
0.7714 Intermediate Similarity NPC476734
0.7714 Intermediate Similarity NPC470833
0.7692 Intermediate Similarity NPC95958
0.7681 Intermediate Similarity NPC204233
0.7671 Intermediate Similarity NPC3403
0.7671 Intermediate Similarity NPC131584
0.7671 Intermediate Similarity NPC139765
0.7662 Intermediate Similarity NPC477936
0.7656 Intermediate Similarity NPC236588
0.7647 Intermediate Similarity NPC27243
0.7647 Intermediate Similarity NPC80463
0.7647 Intermediate Similarity NPC476737
0.7639 Intermediate Similarity NPC232112
0.7632 Intermediate Similarity NPC16449
0.7632 Intermediate Similarity NPC13554
0.7606 Intermediate Similarity NPC477929
0.76 Intermediate Similarity NPC477817
0.76 Intermediate Similarity NPC472501
0.76 Intermediate Similarity NPC102708
0.76 Intermediate Similarity NPC477819
0.7595 Intermediate Similarity NPC266651
0.7571 Intermediate Similarity NPC473225
0.7568 Intermediate Similarity NPC38141
0.7564 Intermediate Similarity NPC259173
0.7534 Intermediate Similarity NPC167702
0.7534 Intermediate Similarity NPC478130
0.7534 Intermediate Similarity NPC254340
0.7534 Intermediate Similarity NPC280026
0.7534 Intermediate Similarity NPC475458
0.7532 Intermediate Similarity NPC12933
0.75 Intermediate Similarity NPC328714
0.75 Intermediate Similarity NPC245029
0.75 Intermediate Similarity NPC111234
0.75 Intermediate Similarity NPC121981
0.75 Intermediate Similarity NPC474448
0.75 Intermediate Similarity NPC476727
0.75 Intermediate Similarity NPC31302
0.75 Intermediate Similarity NPC472272
0.75 Intermediate Similarity NPC476726
0.75 Intermediate Similarity NPC473267
0.75 Intermediate Similarity NPC476176
0.7468 Intermediate Similarity NPC227260
0.7468 Intermediate Similarity NPC255882
0.7467 Intermediate Similarity NPC138502
0.7467 Intermediate Similarity NPC307336
0.7467 Intermediate Similarity NPC475031
0.7467 Intermediate Similarity NPC474404
0.7467 Intermediate Similarity NPC260301
0.7467 Intermediate Similarity NPC23884
0.7465 Intermediate Similarity NPC131892
0.7465 Intermediate Similarity NPC327728
0.7465 Intermediate Similarity NPC213178
0.7465 Intermediate Similarity NPC6120
0.7463 Intermediate Similarity NPC95804
0.7463 Intermediate Similarity NPC185547
0.7436 Intermediate Similarity NPC60018
0.7436 Intermediate Similarity NPC202688
0.7436 Intermediate Similarity NPC154043
0.7436 Intermediate Similarity NPC470611
0.7436 Intermediate Similarity NPC328007
0.7432 Intermediate Similarity NPC97534
0.7432 Intermediate Similarity NPC212879

  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 NPC243469 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
0.8788 High Similarity NPD4267 Clinical (unspecified phase)
0.8657 High Similarity NPD4787 Phase 1
0.8116 Intermediate Similarity NPD4244 Approved
0.8116 Intermediate Similarity NPD4245 Approved
0.7971 Intermediate Similarity NPD3698 Phase 2
0.7857 Intermediate Similarity NPD4789 Approved
0.7746 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD5360 Phase 3
0.7571 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD3702 Approved
0.7403 Intermediate Similarity NPD6928 Phase 2
0.7342 Intermediate Similarity NPD4788 Approved
0.7333 Intermediate Similarity NPD6117 Approved
0.7324 Intermediate Similarity NPD6705 Phase 1
0.726 Intermediate Similarity NPD4243 Approved
0.7237 Intermediate Similarity NPD6116 Phase 1
0.7179 Intermediate Similarity NPD7525 Registered
0.7143 Intermediate Similarity NPD6115 Approved
0.7143 Intermediate Similarity NPD6118 Approved
0.7143 Intermediate Similarity NPD6114 Approved
0.7143 Intermediate Similarity NPD6697 Approved
0.7105 Intermediate Similarity NPD6933 Approved
0.7105 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD4785 Approved
0.7067 Intermediate Similarity NPD4784 Approved
0.7042 Intermediate Similarity NPD4224 Phase 2
0.7027 Intermediate Similarity NPD6081 Approved
0.7027 Intermediate Similarity NPD4758 Discontinued
0.7027 Intermediate Similarity NPD5777 Approved
0.6974 Remote Similarity NPD6942 Approved
0.6974 Remote Similarity NPD7339 Approved
0.6974 Remote Similarity NPD3703 Phase 2
0.6962 Remote Similarity NPD4748 Discontinued
0.6842 Remote Similarity NPD6926 Approved
0.6842 Remote Similarity NPD6924 Approved
0.6782 Remote Similarity NPD8171 Discontinued
0.6753 Remote Similarity NPD4190 Phase 3
0.6753 Remote Similarity NPD5275 Approved
0.6709 Remote Similarity NPD3671 Phase 1
0.6709 Remote Similarity NPD5364 Discontinued
0.6625 Remote Similarity NPD4195 Approved
0.6588 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6548 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6437 Remote Similarity NPD4753 Phase 2
0.6429 Remote Similarity NPD4786 Approved
0.6429 Remote Similarity NPD3666 Approved
0.6429 Remote Similarity NPD3665 Phase 1
0.6429 Remote Similarity NPD3133 Approved
0.6386 Remote Similarity NPD4223 Phase 3
0.6386 Remote Similarity NPD4221 Approved
0.6353 Remote Similarity NPD5329 Approved
0.6349 Remote Similarity NPD385 Approved
0.6349 Remote Similarity NPD384 Approved
0.6341 Remote Similarity NPD6930 Phase 2
0.6341 Remote Similarity NPD6931 Approved
0.6316 Remote Similarity NPD6923 Approved
0.6316 Remote Similarity NPD6922 Approved
0.6265 Remote Similarity NPD4692 Approved
0.6265 Remote Similarity NPD4139 Approved
0.6235 Remote Similarity NPD4197 Approved
0.6234 Remote Similarity NPD7143 Approved
0.6234 Remote Similarity NPD7144 Approved
0.6222 Remote Similarity NPD4202 Approved
0.622 Remote Similarity NPD6929 Approved
0.622 Remote Similarity NPD7645 Phase 2
0.6207 Remote Similarity NPD7524 Approved
0.6197 Remote Similarity NPD3198 Approved
0.619 Remote Similarity NPD3667 Approved
0.619 Remote Similarity NPD388 Approved
0.619 Remote Similarity NPD386 Approved
0.618 Remote Similarity NPD6701 Clinical (unspecified phase)
0.618 Remote Similarity NPD6700 Approved
0.6173 Remote Similarity NPD6932 Approved
0.6154 Remote Similarity NPD7151 Approved
0.6154 Remote Similarity NPD7152 Approved
0.6154 Remote Similarity NPD7150 Approved
0.6145 Remote Similarity NPD7509 Discontinued
0.6129 Remote Similarity NPD6084 Phase 2
0.6129 Remote Similarity NPD6083 Phase 2
0.6118 Remote Similarity NPD6695 Phase 3
0.6111 Remote Similarity NPD6703 Approved
0.6111 Remote Similarity NPD6702 Approved
0.6092 Remote Similarity NPD4688 Approved
0.6092 Remote Similarity NPD4690 Approved
0.6092 Remote Similarity NPD4693 Phase 3
0.6092 Remote Similarity NPD4138 Approved
0.6092 Remote Similarity NPD4689 Approved
0.6092 Remote Similarity NPD5205 Approved
0.6087 Remote Similarity NPD5210 Approved
0.6087 Remote Similarity NPD4629 Approved
0.6087 Remote Similarity NPD7991 Discontinued
0.6082 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6081 Remote Similarity NPD371 Approved
0.6067 Remote Similarity NPD5328 Approved
0.6047 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6024 Remote Similarity NPD6683 Phase 2
0.5977 Remote Similarity NPD6893 Approved
0.5976 Remote Similarity NPD5776 Phase 2
0.5976 Remote Similarity NPD6925 Approved
0.5957 Remote Similarity NPD4755 Approved
0.5955 Remote Similarity NPD4723 Approved
0.5955 Remote Similarity NPD4722 Approved
0.5952 Remote Similarity NPD7514 Phase 3
0.5938 Remote Similarity NPD4159 Approved
0.5934 Remote Similarity NPD8034 Phase 2
0.5934 Remote Similarity NPD8035 Phase 2
0.5934 Remote Similarity NPD6079 Approved
0.5909 Remote Similarity NPD4694 Approved
0.5909 Remote Similarity NPD3618 Phase 1
0.5909 Remote Similarity NPD5280 Approved
0.5909 Remote Similarity NPD5690 Phase 2
0.5904 Remote Similarity NPD7145 Approved
0.5904 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5904 Remote Similarity NPD3617 Approved
0.5889 Remote Similarity NPD6051 Approved
0.5843 Remote Similarity NPD7750 Discontinued
0.5833 Remote Similarity NPD5285 Approved
0.5833 Remote Similarity NPD4700 Approved
0.5833 Remote Similarity NPD5286 Approved
0.5833 Remote Similarity NPD4696 Approved
0.5802 Remote Similarity NPD1810 Approved
0.5802 Remote Similarity NPD1811 Approved
0.5789 Remote Similarity NPD7919 Phase 3
0.5789 Remote Similarity NPD7920 Phase 3
0.5778 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5773 Remote Similarity NPD5223 Approved
0.5765 Remote Similarity NPD7332 Phase 2
0.5745 Remote Similarity NPD5695 Phase 3
0.573 Remote Similarity NPD7521 Approved
0.573 Remote Similarity NPD5279 Phase 3
0.573 Remote Similarity NPD7146 Approved
0.573 Remote Similarity NPD3574 Clinical (unspecified phase)
0.573 Remote Similarity NPD6098 Approved
0.573 Remote Similarity NPD7334 Approved
0.573 Remote Similarity NPD6684 Approved
0.573 Remote Similarity NPD8308 Discontinued
0.573 Remote Similarity NPD6409 Approved
0.573 Remote Similarity NPD5330 Approved
0.5729 Remote Similarity NPD7638 Approved
0.5729 Remote Similarity NPD5696 Approved
0.5729 Remote Similarity NPD8088 Phase 1
0.5714 Remote Similarity NPD5225 Approved
0.5714 Remote Similarity NPD5224 Approved
0.5714 Remote Similarity NPD4633 Approved
0.5714 Remote Similarity NPD5226 Approved
0.5714 Remote Similarity NPD5211 Phase 2
0.57 Remote Similarity NPD7128 Approved
0.57 Remote Similarity NPD5739 Approved
0.57 Remote Similarity NPD6402 Approved
0.57 Remote Similarity NPD6675 Approved
0.5699 Remote Similarity NPD6399 Phase 3
0.5698 Remote Similarity NPD6898 Phase 1
0.5698 Remote Similarity NPD6902 Approved
0.567 Remote Similarity NPD7640 Approved
0.567 Remote Similarity NPD7639 Approved
0.567 Remote Similarity NPD8418 Phase 2
0.5657 Remote Similarity NPD4754 Approved
0.5657 Remote Similarity NPD5175 Approved
0.5657 Remote Similarity NPD5174 Approved
0.5644 Remote Similarity NPD6412 Phase 2
0.5631 Remote Similarity NPD4634 Approved
0.5604 Remote Similarity NPD6903 Approved
0.56 Remote Similarity NPD5141 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