Structure

Physi-Chem Properties

Molecular Weight:  320.24
Volume:  343.985
LogP:  3.815
LogD:  3.181
LogS:  -3.512
# Rotatable Bonds:  2
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.805
Synthetic Accessibility Score:  5.55
Fsp3:  0.95
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.476
MDCK Permeability:  3.503962716422393e-06
Pgp-inhibitor:  0.403
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.153
Plasma Protein Binding (PPB):  93.21764373779297%
Volume Distribution (VD):  0.634
Pgp-substrate:  4.490723609924316%

ADMET: Metabolism

CYP1A2-inhibitor:  0.016
CYP1A2-substrate:  0.523
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.788
CYP2C9-inhibitor:  0.062
CYP2C9-substrate:  0.113
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.177
CYP3A4-inhibitor:  0.261
CYP3A4-substrate:  0.093

ADMET: Excretion

Clearance (CL):  1.017
Half-life (T1/2):  0.551

ADMET: Toxicity

hERG Blockers:  0.055
Human Hepatotoxicity (H-HT):  0.539
Drug-inuced Liver Injury (DILI):  0.089
AMES Toxicity:  0.005
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.569
Skin Sensitization:  0.931
Carcinogencity:  0.266
Eye Corrosion:  0.224
Eye Irritation:  0.439
Respiratory Toxicity:  0.938

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  Natural Product: NPC252032

Natural Product ID:  NPC252032
Common Name*:   HHAMKMUMKLXDFQ-IHAQYFQTSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  HHAMKMUMKLXDFQ-IHAQYFQTSA-N
Standard InCHI:  InChI=1S/C20H32O3/c1-18-7-3-8-19(2,17(22)23)15(18)6-9-20-10-13(4-5-16(18)20)14(11-20)12-21/h13-16,21H,3-12H2,1-2H3,(H,22,23)/t13-,14+,15+,16+,18-,19-,20+/m1/s1
SMILES:  OC[C@@H]1C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@H](CC2)[C@@](C)(CCC1)C(=O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL448617
PubChem CID:   44575990
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
NPO19242 Eucalyptus albens Species Myrtaceae Eukaryota flowers n.a. n.a. PMID[10075775]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[10479331]
NPO2884 Annona squamosa Species Annonaceae Eukaryota seeds n.a. n.a. PMID[11141125]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[12398544]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seeds n.a. n.a. PMID[15387664]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[18419154]
NPO19083 Alstonia angustiloba Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[18524603]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[19296389]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. stem n.a. PMID[21443171]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21910504]
NPO2884 Annona squamosa Species Annonaceae Eukaryota seeds n.a. n.a. PMID[22011319]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. seed n.a. PMID[22011319]
NPO2884 Annona squamosa Species Annonaceae Eukaryota Barks n.a. n.a. PMID[2348205]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
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]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. fruit n.a. PMID[8786370]
NPO2884 Annona squamosa Species Annonaceae Eukaryota bark n.a. n.a. PMID[9214729]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. Suriname rainforest n.a. PMID[9428162]
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]
NPO2884 Annona squamosa Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO2884 Annona squamosa Species Annonaceae Eukaryota 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]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13737 Tephroseris kirilowii Species Asteraceae 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]
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]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11967 Delphinium giraldii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18676 Clerodendrum trichotomum Species Lamiaceae 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]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19769 Boschniakia rossica Species Orobanchaceae 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]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18262 Aspergillus microcysticus Species Aspergillaceae 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]
NPO17296 Beesia calthifolia Species Ranunculaceae 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]
NPO12223 Stellaria media Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11164 Renealmia alpinia Species Zingiberaceae 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]
NPO17230 Psidium acutangulum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19242 Eucalyptus albens 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]
NPO19709 Pseudocyphellaria australiensis Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19371 Costasiella ocellifera Species Costasiellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4679 Hedysarum gmelini Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18048 Phlomis crinita Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18348 Crotalaria stolzii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9906 Zephyranthes flava Species Amaryllidaceae Eukaryota 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]
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]
NPO968 Artemisia pectinata 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]
NPO25370 Botrychium ternatum Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5455 Euploca racemosa Species Heliotropiaceae 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]
NPO24402.1 Coffea liberica var. dewevrei Varieties Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18169 Creosphaeria sassafras Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16325 Sideritis dasygnaphala Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17499 Bursera kerberi Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29450 Streptomyces parvisporogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19436 Annona cherimola Species Annonaceae 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]
NPO19769 Boschniakia rossica Species Orobanchaceae 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]
NPO19170 Lasianthaea podocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15127 Senecio congestus Species Asteraceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 4.1 % PMID[560080]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 23.8 % PMID[560080]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 7.4 % PMID[560080]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 2.8 % PMID[560080]

☑ 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 NPC252032 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 NPC476734
1.0 High Similarity NPC469941
1.0 High Similarity NPC319671
0.9846 High Similarity NPC477929
0.9545 High Similarity NPC477850
0.9531 High Similarity NPC42060
0.9412 High Similarity NPC167702
0.9412 High Similarity NPC280026
0.9412 High Similarity NPC477930
0.9403 High Similarity NPC469940
0.9394 High Similarity NPC64466
0.9275 High Similarity NPC212733
0.9231 High Similarity NPC477931
0.9231 High Similarity NPC268736
0.9143 High Similarity NPC4209
0.9143 High Similarity NPC477933
0.9143 High Similarity NPC477932
0.9091 High Similarity NPC474221
0.9091 High Similarity NPC478180
0.9091 High Similarity NPC130459
0.9014 High Similarity NPC207010
0.9014 High Similarity NPC180199
0.9014 High Similarity NPC143133
0.9014 High Similarity NPC477919
0.9014 High Similarity NPC317913
0.9014 High Similarity NPC298168
0.9 High Similarity NPC472311
0.9 High Similarity NPC477934
0.8971 High Similarity NPC108131
0.8889 High Similarity NPC171426
0.8889 High Similarity NPC224802
0.8889 High Similarity NPC34046
0.8889 High Similarity NPC324700
0.8889 High Similarity NPC199965
0.8889 High Similarity NPC80089
0.8889 High Similarity NPC185465
0.8889 High Similarity NPC476732
0.8841 High Similarity NPC320549
0.8841 High Similarity NPC156277
0.8841 High Similarity NPC151018
0.8841 High Similarity NPC58057
0.8824 High Similarity NPC474962
0.8824 High Similarity NPC196197
0.8767 High Similarity NPC201276
0.8767 High Similarity NPC80891
0.8767 High Similarity NPC320144
0.875 High Similarity NPC477918
0.8714 High Similarity NPC232112
0.8714 High Similarity NPC310766
0.863 High Similarity NPC329117
0.8592 High Similarity NPC472854
0.8592 High Similarity NPC254340
0.8571 High Similarity NPC473267
0.8551 High Similarity NPC324607
0.8551 High Similarity NPC131892
0.8551 High Similarity NPC213178
0.8551 High Similarity NPC327728
0.8551 High Similarity NPC321732
0.8551 High Similarity NPC6120
0.8533 High Similarity NPC58631
0.8533 High Similarity NPC12933
0.8493 Intermediate Similarity NPC474404
0.8472 Intermediate Similarity NPC174964
0.8472 Intermediate Similarity NPC27349
0.8472 Intermediate Similarity NPC125767
0.8472 Intermediate Similarity NPC195155
0.8472 Intermediate Similarity NPC273366
0.8472 Intermediate Similarity NPC21220
0.8472 Intermediate Similarity NPC97534
0.8472 Intermediate Similarity NPC24014
0.8438 Intermediate Similarity NPC476735
0.8429 Intermediate Similarity NPC476731
0.8421 Intermediate Similarity NPC121121
0.8421 Intermediate Similarity NPC477935
0.8421 Intermediate Similarity NPC61107
0.8421 Intermediate Similarity NPC30583
0.8421 Intermediate Similarity NPC289486
0.8406 Intermediate Similarity NPC473225
0.84 Intermediate Similarity NPC261616
0.84 Intermediate Similarity NPC477851
0.84 Intermediate Similarity NPC472853
0.8356 Intermediate Similarity NPC475742
0.8356 Intermediate Similarity NPC472487
0.8356 Intermediate Similarity NPC246445
0.8356 Intermediate Similarity NPC472486
0.8356 Intermediate Similarity NPC5767
0.8312 Intermediate Similarity NPC245866
0.831 Intermediate Similarity NPC472309
0.831 Intermediate Similarity NPC89310
0.8267 Intermediate Similarity NPC472310
0.8243 Intermediate Similarity NPC66105
0.8243 Intermediate Similarity NPC475031
0.8243 Intermediate Similarity NPC68828
0.8243 Intermediate Similarity NPC221420
0.8243 Intermediate Similarity NPC264602
0.8243 Intermediate Similarity NPC23884
0.8219 Intermediate Similarity NPC179858
0.8205 Intermediate Similarity NPC473336
0.8205 Intermediate Similarity NPC471044
0.8194 Intermediate Similarity NPC161187
0.8194 Intermediate Similarity NPC330659
0.8194 Intermediate Similarity NPC244708
0.8182 Intermediate Similarity NPC477936
0.8143 Intermediate Similarity NPC180777
0.8143 Intermediate Similarity NPC31187
0.8143 Intermediate Similarity NPC260319
0.8143 Intermediate Similarity NPC103647
0.8143 Intermediate Similarity NPC474954
0.8143 Intermediate Similarity NPC100917
0.8143 Intermediate Similarity NPC2568
0.8143 Intermediate Similarity NPC281203
0.8143 Intermediate Similarity NPC469724
0.8101 Intermediate Similarity NPC294438
0.8101 Intermediate Similarity NPC201655
0.8101 Intermediate Similarity NPC264317
0.8082 Intermediate Similarity NPC133922
0.8077 Intermediate Similarity NPC259173
0.8056 Intermediate Similarity NPC197701
0.8056 Intermediate Similarity NPC478227
0.8026 Intermediate Similarity NPC52951
0.8026 Intermediate Similarity NPC192744
0.8026 Intermediate Similarity NPC201459
0.8 Intermediate Similarity NPC92139
0.8 Intermediate Similarity NPC70661
0.8 Intermediate Similarity NPC2783
0.8 Intermediate Similarity NPC80590
0.8 Intermediate Similarity NPC302111
0.8 Intermediate Similarity NPC12774
0.8 Intermediate Similarity NPC472272
0.8 Intermediate Similarity NPC41542
0.7975 Intermediate Similarity NPC263974
0.7975 Intermediate Similarity NPC319909
0.7973 Intermediate Similarity NPC159789
0.7971 Intermediate Similarity NPC230047
0.7971 Intermediate Similarity NPC19311
0.7949 Intermediate Similarity NPC170985
0.7949 Intermediate Similarity NPC100366
0.7949 Intermediate Similarity NPC164289
0.7949 Intermediate Similarity NPC242771
0.7949 Intermediate Similarity NPC311642
0.7945 Intermediate Similarity NPC279241
0.7941 Intermediate Similarity NPC114891
0.7922 Intermediate Similarity NPC470609
0.7917 Intermediate Similarity NPC91369
0.7901 Intermediate Similarity NPC134197
0.7901 Intermediate Similarity NPC252714
0.7901 Intermediate Similarity NPC264005
0.7901 Intermediate Similarity NPC33768
0.7901 Intermediate Similarity NPC269360
0.7895 Intermediate Similarity NPC472608
0.7895 Intermediate Similarity NPC26029
0.7887 Intermediate Similarity NPC470956
0.7867 Intermediate Similarity NPC471046
0.7848 Intermediate Similarity NPC471037
0.7821 Intermediate Similarity NPC474484
0.7821 Intermediate Similarity NPC48756
0.7821 Intermediate Similarity NPC103754
0.7821 Intermediate Similarity NPC469745
0.7821 Intermediate Similarity NPC280781
0.7808 Intermediate Similarity NPC290058
0.7805 Intermediate Similarity NPC474719
0.7805 Intermediate Similarity NPC211162
0.7805 Intermediate Similarity NPC146937
0.7805 Intermediate Similarity NPC16377
0.7805 Intermediate Similarity NPC471900
0.7805 Intermediate Similarity NPC183374
0.7794 Intermediate Similarity NPC71460
0.7794 Intermediate Similarity NPC218585
0.7794 Intermediate Similarity NPC148174
0.7794 Intermediate Similarity NPC306750
0.7792 Intermediate Similarity NPC245029
0.7792 Intermediate Similarity NPC31302
0.7778 Intermediate Similarity NPC155011
0.7778 Intermediate Similarity NPC295788
0.7778 Intermediate Similarity NPC178541
0.7763 Intermediate Similarity NPC212661
0.7763 Intermediate Similarity NPC106078
0.7763 Intermediate Similarity NPC471035
0.7763 Intermediate Similarity NPC171658
0.775 Intermediate Similarity NPC476038
0.775 Intermediate Similarity NPC194937
0.7733 Intermediate Similarity NPC132064
0.7722 Intermediate Similarity NPC145143
0.7722 Intermediate Similarity NPC477858
0.7722 Intermediate Similarity NPC328007
0.7722 Intermediate Similarity NPC148740
0.7722 Intermediate Similarity NPC317066
0.7722 Intermediate Similarity NPC268040
0.7722 Intermediate Similarity NPC102156
0.7714 Intermediate Similarity NPC243469
0.7714 Intermediate Similarity NPC475943
0.7714 Intermediate Similarity NPC469791
0.7714 Intermediate Similarity NPC190827
0.7711 Intermediate Similarity NPC24705
0.7711 Intermediate Similarity NPC56962
0.7711 Intermediate Similarity NPC57954
0.7711 Intermediate Similarity NPC24772
0.7711 Intermediate Similarity NPC213832
0.7711 Intermediate Similarity NPC220498
0.7711 Intermediate Similarity NPC116146

  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 NPC252032 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
0.9412 High Similarity NPD6113 Clinical (unspecified phase)
0.9143 High Similarity NPD6117 Approved
0.9014 High Similarity NPD6116 Phase 1
0.8971 High Similarity NPD4789 Approved
0.8939 High Similarity NPD4224 Phase 2
0.8889 High Similarity NPD6697 Approved
0.8889 High Similarity NPD6114 Approved
0.8889 High Similarity NPD6115 Approved
0.8889 High Similarity NPD6118 Approved
0.8841 High Similarity NPD6081 Approved
0.8841 High Similarity NPD4808 Clinical (unspecified phase)
0.8841 High Similarity NPD4809 Clinical (unspecified phase)
0.8788 High Similarity NPD3171 Clinical (unspecified phase)
0.8696 High Similarity NPD4244 Approved
0.8696 High Similarity NPD4245 Approved
0.8551 High Similarity NPD3698 Phase 2
0.8551 High Similarity NPD3699 Clinical (unspecified phase)
0.8551 High Similarity NPD3700 Clinical (unspecified phase)
0.8472 Intermediate Similarity NPD3702 Approved
0.8406 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.8406 Intermediate Similarity NPD5360 Phase 3
0.831 Intermediate Similarity NPD5777 Approved
0.8101 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD3703 Phase 2
0.7808 Intermediate Similarity NPD4758 Discontinued
0.7662 Intermediate Similarity NPD3671 Phase 1
0.7625 Intermediate Similarity NPD4788 Approved
0.75 Intermediate Similarity NPD3198 Approved
0.7436 Intermediate Similarity NPD5364 Discontinued
0.7326 Intermediate Similarity NPD8034 Phase 2
0.7326 Intermediate Similarity NPD8035 Phase 2
0.7317 Intermediate Similarity NPD4786 Approved
0.7297 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4787 Phase 1
0.7073 Intermediate Similarity NPD3667 Approved
0.7045 Intermediate Similarity NPD6399 Phase 3
0.7015 Intermediate Similarity NPD3729 Clinical (unspecified phase)
0.6957 Remote Similarity NPD8418 Phase 2
0.6933 Remote Similarity NPD6705 Phase 1
0.6923 Remote Similarity NPD6084 Phase 2
0.6923 Remote Similarity NPD6083 Phase 2
0.6905 Remote Similarity NPD3666 Approved
0.6905 Remote Similarity NPD3133 Approved
0.6905 Remote Similarity NPD3665 Phase 1
0.6897 Remote Similarity NPD5328 Approved
0.679 Remote Similarity NPD3617 Approved
0.6782 Remote Similarity NPD5737 Approved
0.6782 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6782 Remote Similarity NPD6672 Approved
0.6765 Remote Similarity NPD615 Clinical (unspecified phase)
0.6744 Remote Similarity NPD7521 Approved
0.6744 Remote Similarity NPD3618 Phase 1
0.6744 Remote Similarity NPD7334 Approved
0.6744 Remote Similarity NPD6409 Approved
0.6744 Remote Similarity NPD6684 Approved
0.6744 Remote Similarity NPD5330 Approved
0.6744 Remote Similarity NPD7146 Approved
0.6742 Remote Similarity NPD7515 Phase 2
0.6742 Remote Similarity NPD6079 Approved
0.6705 Remote Similarity NPD4753 Phase 2
0.6667 Remote Similarity NPD4221 Approved
0.6667 Remote Similarity NPD4223 Phase 3
0.6628 Remote Similarity NPD5329 Approved
0.6627 Remote Similarity NPD6928 Phase 2
0.6591 Remote Similarity NPD6903 Approved
0.6562 Remote Similarity NPD634 Phase 3
0.6552 Remote Similarity NPD6098 Approved
0.6552 Remote Similarity NPD5279 Phase 3
0.6548 Remote Similarity NPD4692 Approved
0.6548 Remote Similarity NPD4139 Approved
0.6522 Remote Similarity NPD5695 Phase 3
0.6512 Remote Similarity NPD4197 Approved
0.6489 Remote Similarity NPD7638 Approved
0.6489 Remote Similarity NPD5696 Approved
0.6484 Remote Similarity NPD4202 Approved
0.6471 Remote Similarity NPD3186 Phase 1
0.6447 Remote Similarity NPD375 Phase 2
0.6429 Remote Similarity NPD6675 Approved
0.6429 Remote Similarity NPD5739 Approved
0.6429 Remote Similarity NPD6402 Approved
0.6429 Remote Similarity NPD7128 Approved
0.6429 Remote Similarity NPD7525 Registered
0.6421 Remote Similarity NPD7640 Approved
0.6421 Remote Similarity NPD7639 Approved
0.642 Remote Similarity NPD6942 Approved
0.642 Remote Similarity NPD7339 Approved
0.6413 Remote Similarity NPD7748 Approved
0.641 Remote Similarity NPD3725 Approved
0.641 Remote Similarity NPD3726 Approved
0.64 Remote Similarity NPD7909 Approved
0.6386 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6374 Remote Similarity NPD5281 Approved
0.6374 Remote Similarity NPD5284 Approved
0.6364 Remote Similarity NPD4690 Approved
0.6364 Remote Similarity NPD4693 Phase 3
0.6364 Remote Similarity NPD5205 Approved
0.6364 Remote Similarity NPD4689 Approved
0.6364 Remote Similarity NPD4138 Approved
0.6364 Remote Similarity NPD4688 Approved
0.6344 Remote Similarity NPD4629 Approved
0.6344 Remote Similarity NPD5210 Approved
0.6333 Remote Similarity NPD6904 Approved
0.6333 Remote Similarity NPD6673 Approved
0.6333 Remote Similarity NPD6080 Approved
0.6333 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6327 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6322 Remote Similarity NPD3668 Phase 3
0.63 Remote Similarity NPD6881 Approved
0.63 Remote Similarity NPD6899 Approved
0.63 Remote Similarity NPD7320 Approved
0.6289 Remote Similarity NPD7632 Discontinued
0.6277 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6277 Remote Similarity NPD4697 Phase 3
0.6277 Remote Similarity NPD5221 Approved
0.6277 Remote Similarity NPD5222 Approved
0.6238 Remote Similarity NPD6373 Approved
0.6238 Remote Similarity NPD6372 Approved
0.6222 Remote Similarity NPD5208 Approved
0.6211 Remote Similarity NPD5173 Approved
0.6211 Remote Similarity NPD4755 Approved
0.6211 Remote Similarity NPD7902 Approved
0.62 Remote Similarity NPD5701 Approved
0.62 Remote Similarity NPD5697 Approved
0.619 Remote Similarity NPD4238 Approved
0.619 Remote Similarity NPD4802 Phase 2
0.618 Remote Similarity NPD5690 Phase 2
0.618 Remote Similarity NPD3574 Clinical (unspecified phase)
0.618 Remote Similarity NPD4694 Approved
0.618 Remote Similarity NPD5280 Approved
0.6176 Remote Similarity NPD7290 Approved
0.6176 Remote Similarity NPD7102 Approved
0.6176 Remote Similarity NPD6883 Approved
0.617 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8298 Phase 2
0.6145 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6139 Remote Similarity NPD6011 Approved
0.6119 Remote Similarity NPD2266 Phase 2
0.6117 Remote Similarity NPD6847 Approved
0.6117 Remote Similarity NPD6649 Approved
0.6117 Remote Similarity NPD6869 Approved
0.6117 Remote Similarity NPD6617 Approved
0.6117 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6117 Remote Similarity NPD6650 Approved
0.6117 Remote Similarity NPD8130 Phase 1
0.61 Remote Similarity NPD6920 Discontinued
0.6098 Remote Similarity NPD6924 Approved
0.6098 Remote Similarity NPD6926 Approved
0.6094 Remote Similarity NPD387 Clinical (unspecified phase)
0.6092 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6082 Remote Similarity NPD4696 Approved
0.6082 Remote Similarity NPD5285 Approved
0.6082 Remote Similarity NPD6404 Discontinued
0.6082 Remote Similarity NPD5286 Approved
0.6082 Remote Similarity NPD4700 Approved
0.6078 Remote Similarity NPD6013 Approved
0.6078 Remote Similarity NPD6014 Approved
0.6078 Remote Similarity NPD6012 Approved
0.6058 Remote Similarity NPD6882 Approved
0.6058 Remote Similarity NPD8297 Approved
0.6049 Remote Similarity NPD4243 Approved
0.6038 Remote Similarity NPD6940 Discontinued
0.6022 Remote Similarity NPD6050 Approved
0.6022 Remote Similarity NPD5693 Phase 1
0.602 Remote Similarity NPD5223 Approved
0.6 Remote Similarity NPD8133 Approved
0.6 Remote Similarity NPD4776 Phase 2
0.6 Remote Similarity NPD4777 Suspended
0.598 Remote Similarity NPD6415 Discontinued
0.596 Remote Similarity NPD5225 Approved
0.596 Remote Similarity NPD5211 Phase 2
0.596 Remote Similarity NPD5226 Approved
0.596 Remote Similarity NPD4633 Approved
0.596 Remote Similarity NPD5224 Approved
0.5952 Remote Similarity NPD6933 Approved
0.5938 Remote Similarity NPD2270 Approved
0.5938 Remote Similarity NPD7614 Phase 1
0.593 Remote Similarity NPD4195 Approved
0.5926 Remote Similarity NPD4747 Approved
0.5914 Remote Similarity NPD5207 Approved
0.5914 Remote Similarity NPD5692 Phase 3
0.5904 Remote Similarity NPD4784 Approved
0.5904 Remote Similarity NPD4785 Approved
0.59 Remote Similarity NPD5175 Approved
0.59 Remote Similarity NPD5174 Approved
0.59 Remote Similarity NPD4754 Approved
0.5895 Remote Similarity NPD7900 Approved
0.5895 Remote Similarity NPD6001 Approved
0.5895 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5888 Remote Similarity NPD6868 Approved
0.5882 Remote Similarity NPD6412 Phase 2
0.5862 Remote Similarity NPD4695 Discontinued
0.5862 Remote Similarity NPD4748 Discontinued
0.5862 Remote Similarity NPD5368 Approved
0.5851 Remote Similarity NPD5694 Approved
0.5851 Remote Similarity NPD7637 Suspended
0.5851 Remote Similarity NPD6411 Approved
0.5849 Remote Similarity NPD4632 Approved
0.5843 Remote Similarity NPD5362 Discontinued
0.5842 Remote Similarity NPD5141 Approved
0.5833 Remote Similarity NPD2257 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