Structure

Physi-Chem Properties

Molecular Weight:  262.12
Volume:  266.942
LogP:  2.055
LogD:  1.673
LogS:  -3.141
# Rotatable Bonds:  0
TPSA:  55.9
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.38
Synthetic Accessibility Score:  4.846
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.64
MDCK Permeability:  3.0718267225893214e-05
Pgp-inhibitor:  0.036
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.113
30% Bioavailability (F30%):  0.132

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.649
Plasma Protein Binding (PPB):  49.8600959777832%
Volume Distribution (VD):  0.723
Pgp-substrate:  54.23188018798828%

ADMET: Metabolism

CYP1A2-inhibitor:  0.317
CYP1A2-substrate:  0.648
CYP2C19-inhibitor:  0.305
CYP2C19-substrate:  0.644
CYP2C9-inhibitor:  0.104
CYP2C9-substrate:  0.058
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.193
CYP3A4-inhibitor:  0.108
CYP3A4-substrate:  0.23

ADMET: Excretion

Clearance (CL):  10.494
Half-life (T1/2):  0.549

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.4
Drug-inuced Liver Injury (DILI):  0.161
AMES Toxicity:  0.061
Rat Oral Acute Toxicity:  0.946
Maximum Recommended Daily Dose:  0.832
Skin Sensitization:  0.934
Carcinogencity:  0.834
Eye Corrosion:  0.96
Eye Irritation:  0.971
Respiratory Toxicity:  0.975

Download Data

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

  Natural Product: NPC49342

Natural Product ID:  NPC49342
Common Name*:   MZDVWXBIIWIBTB-BPWSPTIZSA-N
IUPAC Name:   n.a.
Synonyms:   NSC-672120
Standard InCHIKey:  MZDVWXBIIWIBTB-BPWSPTIZSA-N
Standard InCHI:  InChI=1S/C15H18O4/c1-8-5-4-6-15(3)13(19-15)12-10(7-11(8)16)9(2)14(17)18-12/h5,10,12-13H,2,4,6-7H2,1,3H3/b8-5+/t10-,12-,13-,15+/m0/s1
SMILES:  C/C/1=CCC[C@]2(C)[C@H]([C@@H]3[C@@H](CC1=O)C(=C)C(=O)O3)O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479474
PubChem CID:   10445414
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO24419 Anvillea garcinii Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[11087618]
NPO8670 Chloranthus multistachys Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[20392109]
NPO24419 Anvillea garcinii Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8699183]
NPO22958 Cyclamen hederifolium Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24419 Anvillea garcinii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20991 Commiphora pyracanthoides Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18725 Senecio tournefortii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8670 Chloranthus multistachys Species Chloranthaceae 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
NPT404 Cell Line CCRF-CEM Homo sapiens ED50 = 0.05 ug ml-1 PMID[482542]
NPT112 Cell Line MOLT-4 Homo sapiens ED50 = 0.07 ug ml-1 PMID[482542]
NPT379 Cell Line HOP-62 Homo sapiens ED50 = 0.63 ug ml-1 PMID[482542]
NPT455 Cell Line NCI-H522 Homo sapiens ED50 = 0.15 ug ml-1 PMID[482542]
NPT393 Cell Line HCT-116 Homo sapiens ED50 = 0.45 ug ml-1 PMID[482542]
NPT323 Cell Line SW-620 Homo sapiens ED50 = 0.21 ug ml-1 PMID[482542]
NPT395 Cell Line SF-268 Homo sapiens ED50 = 1.73 ug ml-1 PMID[482542]
NPT392 Cell Line SNB-75 Homo sapiens ED50 = 4.38 ug ml-1 PMID[482542]
NPT390 Cell Line LOX IMVI Homo sapiens ED50 = 0.11 ug ml-1 PMID[482542]
NPT375 Cell Line Malme-3M Homo sapiens ED50 = 0.33 ug ml-1 PMID[482542]
NPT458 Cell Line IGROV-1 Homo sapiens ED50 = 0.94 ug ml-1 PMID[482542]
NPT381 Cell Line OVCAR-8 Homo sapiens ED50 = 0.78 ug ml-1 PMID[482542]
NPT369 Cell Line ACHN Homo sapiens ED50 = 0.3 ug ml-1 PMID[482542]
NPT371 Cell Line UO-31 Homo sapiens ED50 = 0.28 ug ml-1 PMID[482542]
NPT306 Cell Line PC-3 Homo sapiens ED50 = 0.9 ug ml-1 PMID[482542]
NPT90 Cell Line DU-145 Homo sapiens ED50 = 3.3 ug ml-1 PMID[482542]
NPT82 Cell Line MDA-MB-231 Homo sapiens ED50 = 0.17 ug ml-1 PMID[482542]
NPT457 Cell Line BT-549 Homo sapiens ED50 = 0.34 ug ml-1 PMID[482542]
NPT396 Cell Line T47D Homo sapiens ED50 = 0.45 ug ml-1 PMID[482542]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 1655.77 nM PMID[482544]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 259.42 nM PMID[482544]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 1667.25 nM PMID[482544]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 879.02 nM PMID[482544]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 461.32 nM PMID[482544]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 739.61 nM PMID[482544]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2084.49 nM PMID[482544]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 6501.3 nM PMID[482544]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 972.75 nM PMID[482544]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 1247.38 nM PMID[482544]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 1644.37 nM PMID[482544]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 172.19 nM PMID[482544]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 224.39 nM PMID[482544]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 223.87 nM PMID[482544]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 8356.03 nM PMID[482544]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 1399.59 nM PMID[482544]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 5000.35 nM PMID[482544]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 2147.83 nM PMID[482544]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 2013.72 nM PMID[482544]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 3198.9 nM PMID[482544]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 1047.13 nM PMID[482544]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 540.75 nM PMID[482544]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 1235.95 nM PMID[482544]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 324.34 nM PMID[482544]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 256.45 nM PMID[482544]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 2488.86 nM PMID[482544]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 369.83 nM PMID[482544]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 12359.47 nM PMID[482544]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 78.16 nM PMID[482544]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 2930.89 nM PMID[482544]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 354.0 nM PMID[482544]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 422.67 nM PMID[482544]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 3026.91 nM PMID[482544]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 12676.52 nM PMID[482544]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 2404.36 nM PMID[482544]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 16672.47 nM PMID[482544]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 515.23 nM PMID[482544]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 719.45 nM PMID[482544]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 3451.44 nM PMID[482544]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 391.74 nM PMID[482544]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 2004.47 nM PMID[482544]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 2187.76 nM PMID[482544]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 12941.96 nM PMID[482544]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 10864.26 nM PMID[482544]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 1116.86 nM PMID[482544]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 1367.73 nM PMID[482544]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 1534.62 nM PMID[482544]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 529.66 nM PMID[482544]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 2037.04 nM PMID[482544]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 16180.8 nM PMID[482544]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 2404.36 nM PMID[482544]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 1422.33 nM PMID[482544]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 582.1 nM PMID[482544]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 84.14 nM PMID[482544]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 4255.98 nM PMID[482544]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 602.56 nM PMID[482544]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 1129.8 nM PMID[482544]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 439.54 nM PMID[482544]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 255.27 nM PMID[482544]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.02 ug ml-1 PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. C50 = 0.08 umol/L PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. C50 = 1.8 umol/L PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. C50 = 0.32 umol/L PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. C50 = 2.9 umol/L PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. C50 = 0.57 umol/L PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. C50 = 1.4 umol/L PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. C50 = 0.41 umol/L PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. C50 = 2.2 umol/L PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. C50 = 0.6 umol/L PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.47 ug ml-1 PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.08 ug ml-1 PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.76 ug ml-1 PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.15 ug ml-1 PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.37 ug ml-1 PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.11 ug ml-1 PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.57 ug ml-1 PMID[482543]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.16 ug ml-1 PMID[482543]

☑ 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 NPC49342 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 NPC251385
0.9405 High Similarity NPC50362
0.9405 High Similarity NPC38468
0.9405 High Similarity NPC319795
0.9195 High Similarity NPC151770
0.9 High Similarity NPC473330
0.9 High Similarity NPC473316
0.8977 High Similarity NPC166919
0.8791 High Similarity NPC471147
0.8791 High Similarity NPC303942
0.8791 High Similarity NPC57405
0.875 High Similarity NPC231889
0.8696 High Similarity NPC475659
0.8667 High Similarity NPC329857
0.8667 High Similarity NPC469718
0.8667 High Similarity NPC475748
0.8667 High Similarity NPC312042
0.8636 High Similarity NPC50637
0.8632 High Similarity NPC476270
0.8617 High Similarity NPC473326
0.8617 High Similarity NPC208233
0.8602 High Similarity NPC473859
0.8602 High Similarity NPC35498
0.8587 High Similarity NPC140543
0.8539 High Similarity NPC475703
0.8526 High Similarity NPC288876
0.8506 High Similarity NPC272814
0.8488 Intermediate Similarity NPC207188
0.8478 Intermediate Similarity NPC212486
0.8478 Intermediate Similarity NPC165383
0.8462 Intermediate Similarity NPC62815
0.8438 Intermediate Similarity NPC264477
0.8438 Intermediate Similarity NPC477511
0.8421 Intermediate Similarity NPC279561
0.8404 Intermediate Similarity NPC476275
0.8404 Intermediate Similarity NPC279621
0.8404 Intermediate Similarity NPC17585
0.8387 Intermediate Similarity NPC476267
0.8352 Intermediate Similarity NPC474032
0.8333 Intermediate Similarity NPC5130
0.8298 Intermediate Similarity NPC14961
0.8298 Intermediate Similarity NPC270013
0.8298 Intermediate Similarity NPC474947
0.828 Intermediate Similarity NPC295204
0.828 Intermediate Similarity NPC288240
0.828 Intermediate Similarity NPC228451
0.828 Intermediate Similarity NPC475838
0.828 Intermediate Similarity NPC125674
0.828 Intermediate Similarity NPC273579
0.828 Intermediate Similarity NPC162205
0.8261 Intermediate Similarity NPC473619
0.8247 Intermediate Similarity NPC47880
0.8247 Intermediate Similarity NPC164598
0.8247 Intermediate Similarity NPC474339
0.8214 Intermediate Similarity NPC155587
0.8211 Intermediate Similarity NPC476315
0.8202 Intermediate Similarity NPC470238
0.8202 Intermediate Similarity NPC138647
0.8191 Intermediate Similarity NPC474035
0.8191 Intermediate Similarity NPC474247
0.8191 Intermediate Similarity NPC81386
0.8182 Intermediate Similarity NPC477510
0.8182 Intermediate Similarity NPC471143
0.8182 Intermediate Similarity NPC173609
0.8172 Intermediate Similarity NPC473321
0.8172 Intermediate Similarity NPC20713
0.8172 Intermediate Similarity NPC184463
0.8163 Intermediate Similarity NPC149371
0.8152 Intermediate Similarity NPC307411
0.8144 Intermediate Similarity NPC477512
0.8125 Intermediate Similarity NPC471140
0.8111 Intermediate Similarity NPC474547
0.8105 Intermediate Similarity NPC471141
0.809 Intermediate Similarity NPC170377
0.8085 Intermediate Similarity NPC475912
0.8085 Intermediate Similarity NPC476300
0.8081 Intermediate Similarity NPC475873
0.8068 Intermediate Similarity NPC141810
0.8065 Intermediate Similarity NPC51004
0.8065 Intermediate Similarity NPC144133
0.8065 Intermediate Similarity NPC179394
0.8061 Intermediate Similarity NPC201718
0.8061 Intermediate Similarity NPC15993
0.8046 Intermediate Similarity NPC617
0.8046 Intermediate Similarity NPC270126
0.8043 Intermediate Similarity NPC473715
0.8043 Intermediate Similarity NPC202672
0.8041 Intermediate Similarity NPC474213
0.8022 Intermediate Similarity NPC284902
0.8021 Intermediate Similarity NPC230800
0.802 Intermediate Similarity NPC477513
0.8 Intermediate Similarity NPC474741
0.798 Intermediate Similarity NPC324017
0.798 Intermediate Similarity NPC320019
0.7979 Intermediate Similarity NPC12172
0.7979 Intermediate Similarity NPC70251
0.7979 Intermediate Similarity NPC30515
0.7979 Intermediate Similarity NPC208886
0.7979 Intermediate Similarity NPC475881
0.7959 Intermediate Similarity NPC475949
0.7955 Intermediate Similarity NPC474510
0.7955 Intermediate Similarity NPC223904
0.7935 Intermediate Similarity NPC266957
0.7917 Intermediate Similarity NPC477922
0.7917 Intermediate Similarity NPC36954
0.7917 Intermediate Similarity NPC471142
0.7912 Intermediate Similarity NPC99395
0.7912 Intermediate Similarity NPC197903
0.7907 Intermediate Similarity NPC235906
0.7895 Intermediate Similarity NPC81419
0.7895 Intermediate Similarity NPC179746
0.7889 Intermediate Similarity NPC170286
0.7889 Intermediate Similarity NPC257358
0.7889 Intermediate Similarity NPC474472
0.7889 Intermediate Similarity NPC318468
0.7879 Intermediate Similarity NPC474742
0.7872 Intermediate Similarity NPC80875
0.7872 Intermediate Similarity NPC474761
0.7872 Intermediate Similarity NPC475855
0.7872 Intermediate Similarity NPC476004
0.7857 Intermediate Similarity NPC471144
0.7849 Intermediate Similarity NPC281516
0.7835 Intermediate Similarity NPC477921
0.7835 Intermediate Similarity NPC31645
0.7826 Intermediate Similarity NPC122502
0.7826 Intermediate Similarity NPC469676
0.7816 Intermediate Similarity NPC476028
0.7816 Intermediate Similarity NPC141789
0.7816 Intermediate Similarity NPC171204
0.7802 Intermediate Similarity NPC96259
0.7802 Intermediate Similarity NPC141193
0.78 Intermediate Similarity NPC474747
0.78 Intermediate Similarity NPC471148
0.7791 Intermediate Similarity NPC193351
0.7791 Intermediate Similarity NPC226669
0.7791 Intermediate Similarity NPC138408
0.7766 Intermediate Similarity NPC295312
0.7766 Intermediate Similarity NPC4986
0.7765 Intermediate Similarity NPC58956
0.7765 Intermediate Similarity NPC269206
0.7765 Intermediate Similarity NPC295633
0.7755 Intermediate Similarity NPC323421
0.7755 Intermediate Similarity NPC328562
0.7753 Intermediate Similarity NPC474981
0.7753 Intermediate Similarity NPC281132
0.7745 Intermediate Similarity NPC223450
0.7745 Intermediate Similarity NPC243998
0.7727 Intermediate Similarity NPC472960
0.7723 Intermediate Similarity NPC475945
0.7723 Intermediate Similarity NPC475871
0.7717 Intermediate Similarity NPC304509
0.7717 Intermediate Similarity NPC21469
0.7717 Intermediate Similarity NPC215364
0.7717 Intermediate Similarity NPC47958
0.7717 Intermediate Similarity NPC149725
0.7708 Intermediate Similarity NPC477615
0.7708 Intermediate Similarity NPC475302
0.7708 Intermediate Similarity NPC135776
0.77 Intermediate Similarity NPC473332
0.7692 Intermediate Similarity NPC39588
0.7692 Intermediate Similarity NPC475947
0.7692 Intermediate Similarity NPC128429
0.7684 Intermediate Similarity NPC71533
0.7684 Intermediate Similarity NPC106510
0.7674 Intermediate Similarity NPC476355
0.7667 Intermediate Similarity NPC10276
0.7667 Intermediate Similarity NPC471325
0.7667 Intermediate Similarity NPC25684
0.7667 Intermediate Similarity NPC301477
0.7667 Intermediate Similarity NPC35089
0.7667 Intermediate Similarity NPC281949
0.766 Intermediate Similarity NPC224652
0.766 Intermediate Similarity NPC475902
0.7647 Intermediate Similarity NPC100487
0.764 Intermediate Similarity NPC178277
0.764 Intermediate Similarity NPC472965
0.764 Intermediate Similarity NPC63649
0.764 Intermediate Similarity NPC264227
0.7634 Intermediate Similarity NPC474045
0.7634 Intermediate Similarity NPC279859
0.7634 Intermediate Similarity NPC38576
0.7634 Intermediate Similarity NPC261253
0.7634 Intermediate Similarity NPC475461
0.7634 Intermediate Similarity NPC305475
0.7634 Intermediate Similarity NPC150755
0.7634 Intermediate Similarity NPC470242
0.7634 Intermediate Similarity NPC204048
0.7629 Intermediate Similarity NPC190294
0.7619 Intermediate Similarity NPC253906
0.7614 Intermediate Similarity NPC470240
0.7614 Intermediate Similarity NPC41780
0.7614 Intermediate Similarity NPC187568
0.7614 Intermediate Similarity NPC476794
0.7614 Intermediate Similarity NPC65603
0.7609 Intermediate Similarity NPC472957
0.7609 Intermediate Similarity NPC472958
0.7609 Intermediate Similarity NPC191476
0.7609 Intermediate Similarity NPC115786
0.7609 Intermediate Similarity NPC72464
0.7609 Intermediate Similarity NPC114979

  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 NPC49342 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
0.9405 High Similarity NPD1733 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD1695 Approved
0.75 Intermediate Similarity NPD46 Approved
0.75 Intermediate Similarity NPD6698 Approved
0.72 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6371 Approved
0.697 Remote Similarity NPD7838 Discovery
0.6804 Remote Similarity NPD1694 Approved
0.6759 Remote Similarity NPD6008 Approved
0.6744 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7983 Approved
0.6509 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6495 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5209 Approved
0.6471 Remote Similarity NPD5785 Approved
0.6449 Remote Similarity NPD6648 Approved
0.6442 Remote Similarity NPD5282 Discontinued
0.6396 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6389 Remote Similarity NPD5344 Discontinued
0.6355 Remote Similarity NPD4225 Approved
0.6339 Remote Similarity NPD6686 Approved
0.6327 Remote Similarity NPD6435 Approved
0.6325 Remote Similarity NPD7115 Discovery
0.6316 Remote Similarity NPD8413 Clinical (unspecified phase)
0.63 Remote Similarity NPD5363 Approved
0.6281 Remote Similarity NPD7642 Approved
0.6263 Remote Similarity NPD7154 Phase 3
0.6261 Remote Similarity NPD6053 Discontinued
0.6238 Remote Similarity NPD5786 Approved
0.6228 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6224 Remote Similarity NPD5369 Approved
0.619 Remote Similarity NPD5779 Approved
0.619 Remote Similarity NPD5778 Approved
0.614 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6122 Remote Similarity NPD5368 Approved
0.6116 Remote Similarity NPD8515 Approved
0.6116 Remote Similarity NPD8517 Approved
0.6116 Remote Similarity NPD8516 Approved
0.6116 Remote Similarity NPD8513 Phase 3
0.6078 Remote Similarity NPD4249 Approved
0.6063 Remote Similarity NPD7260 Phase 2
0.6055 Remote Similarity NPD5696 Approved
0.6019 Remote Similarity NPD4250 Approved
0.6019 Remote Similarity NPD4251 Approved
0.6019 Remote Similarity NPD7839 Suspended
0.6016 Remote Similarity NPD7829 Approved
0.6016 Remote Similarity NPD7830 Approved
0.6 Remote Similarity NPD4269 Approved
0.6 Remote Similarity NPD4270 Approved
0.6 Remote Similarity NPD7641 Discontinued
0.5943 Remote Similarity NPD5693 Phase 1
0.5941 Remote Similarity NPD5362 Discontinued
0.5938 Remote Similarity NPD8039 Approved
0.5934 Remote Similarity NPD7331 Phase 2
0.5932 Remote Similarity NPD4632 Approved
0.5926 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5922 Remote Similarity NPD7521 Approved
0.5922 Remote Similarity NPD7146 Approved
0.5922 Remote Similarity NPD6409 Approved
0.5922 Remote Similarity NPD5330 Approved
0.5922 Remote Similarity NPD6684 Approved
0.5922 Remote Similarity NPD7334 Approved
0.5909 Remote Similarity NPD7638 Approved
0.5905 Remote Similarity NPD6101 Approved
0.5905 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5902 Remote Similarity NPD6319 Approved
0.5891 Remote Similarity NPD6845 Suspended
0.5873 Remote Similarity NPD8074 Phase 3
0.5865 Remote Similarity NPD3573 Approved
0.5856 Remote Similarity NPD7639 Approved
0.5856 Remote Similarity NPD7640 Approved
0.5854 Remote Similarity NPD8444 Approved
0.5847 Remote Similarity NPD8297 Approved
0.584 Remote Similarity NPD7492 Approved
0.5833 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5826 Remote Similarity NPD5697 Approved
0.5825 Remote Similarity NPD6082 Clinical (unspecified phase)
0.581 Remote Similarity NPD5737 Approved
0.581 Remote Similarity NPD6672 Approved
0.581 Remote Similarity NPD7513 Clinical (unspecified phase)
0.581 Remote Similarity NPD6903 Approved
0.58 Remote Similarity NPD4820 Approved
0.58 Remote Similarity NPD4252 Approved
0.58 Remote Similarity NPD5790 Clinical (unspecified phase)
0.58 Remote Similarity NPD4821 Approved
0.58 Remote Similarity NPD4819 Approved
0.58 Remote Similarity NPD4822 Approved
0.5794 Remote Similarity NPD6411 Approved
0.5794 Remote Similarity NPD7507 Approved
0.5794 Remote Similarity NPD6616 Approved
0.5785 Remote Similarity NPD6009 Approved
0.5784 Remote Similarity NPD6110 Phase 1
0.578 Remote Similarity NPD5695 Phase 3
0.5776 Remote Similarity NPD6881 Approved
0.5776 Remote Similarity NPD6899 Approved
0.5776 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5772 Remote Similarity NPD6054 Approved
0.5769 Remote Similarity NPD6422 Discontinued
0.5763 Remote Similarity NPD6650 Approved
0.5763 Remote Similarity NPD6649 Approved
0.576 Remote Similarity NPD7604 Phase 2
0.5758 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5748 Remote Similarity NPD7078 Approved
0.5741 Remote Similarity NPD6399 Phase 3
0.5739 Remote Similarity NPD6675 Approved
0.5739 Remote Similarity NPD5739 Approved
0.5739 Remote Similarity NPD7128 Approved
0.5739 Remote Similarity NPD6402 Approved
0.5726 Remote Similarity NPD6016 Approved
0.5726 Remote Similarity NPD5983 Phase 2
0.5726 Remote Similarity NPD6013 Approved
0.5726 Remote Similarity NPD6015 Approved
0.5726 Remote Similarity NPD6014 Approved
0.5726 Remote Similarity NPD6012 Approved
0.5726 Remote Similarity NPD6373 Approved
0.5726 Remote Similarity NPD6372 Approved
0.5703 Remote Similarity NPD7736 Approved
0.5701 Remote Similarity NPD5207 Approved
0.569 Remote Similarity NPD6412 Phase 2
0.569 Remote Similarity NPD5701 Approved
0.5688 Remote Similarity NPD6001 Approved
0.5688 Remote Similarity NPD7900 Approved
0.5688 Remote Similarity NPD7901 Clinical (unspecified phase)
0.568 Remote Similarity NPD5988 Approved
0.568 Remote Similarity NPD6370 Approved
0.5678 Remote Similarity NPD6883 Approved
0.5678 Remote Similarity NPD7290 Approved
0.5678 Remote Similarity NPD2067 Discontinued
0.5678 Remote Similarity NPD7102 Approved
0.5676 Remote Similarity NPD6083 Phase 2
0.5676 Remote Similarity NPD6084 Phase 2
0.5659 Remote Similarity NPD7319 Approved
0.5657 Remote Similarity NPD4756 Discovery
0.5652 Remote Similarity NPD7341 Phase 2
0.5645 Remote Similarity NPD6059 Approved
0.5641 Remote Similarity NPD6011 Approved
0.5641 Remote Similarity NPD7320 Approved
0.5636 Remote Similarity NPD4629 Approved
0.5636 Remote Similarity NPD5210 Approved
0.563 Remote Similarity NPD2204 Approved
0.563 Remote Similarity NPD6869 Approved
0.563 Remote Similarity NPD6847 Approved
0.563 Remote Similarity NPD6617 Approved
0.563 Remote Similarity NPD8130 Phase 1
0.5625 Remote Similarity NPD8293 Discontinued
0.5607 Remote Similarity NPD6080 Approved
0.5607 Remote Similarity NPD6904 Approved
0.5607 Remote Similarity NPD6673 Approved
0.56 Remote Similarity NPD4268 Approved
0.56 Remote Similarity NPD4271 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