Structure

Physi-Chem Properties

Molecular Weight:  374.21
Volume:  394.168
LogP:  2.413
LogD:  0.305
LogS:  -2.704
# Rotatable Bonds:  2
TPSA:  77.51
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.52
Synthetic Accessibility Score:  5.725
Fsp3:  0.727
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  2
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.735
MDCK Permeability:  1.9392738977330737e-05
Pgp-inhibitor:  0.993
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.017
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.801
Plasma Protein Binding (PPB):  79.78556060791016%
Volume Distribution (VD):  0.646
Pgp-substrate:  29.396745681762695%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.137
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.88
CYP2C9-inhibitor:  0.047
CYP2C9-substrate:  0.27
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.158
CYP3A4-inhibitor:  0.399
CYP3A4-substrate:  0.567

ADMET: Excretion

Clearance (CL):  7.2
Half-life (T1/2):  0.37

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.295
Drug-inuced Liver Injury (DILI):  0.481
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.276
Maximum Recommended Daily Dose:  0.918
Skin Sensitization:  0.098
Carcinogencity:  0.36
Eye Corrosion:  0.038
Eye Irritation:  0.023
Respiratory Toxicity:  0.941

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  Natural Product: NPC306856

Natural Product ID:  NPC306856
Common Name*:   SZAHIEIJJDKFRX-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SZAHIEIJJDKFRX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H30O5/c1-12-14-6-7-18(25)22(5)9-8-19(27-13(2)23)21(3,4)17(22)11-16(24)15(10-14)20(12)26/h10,14,16-17,19,24H,1,6-9,11H2,2-5H3
SMILES:  CC(=O)OC1CCC2(C(C1(C)C)CC(O)C1=CC(CCC2=O)C(=C)C1=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1699228
PubChem CID:   327536
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0001093] Carboxylic acid derivatives
          • [CHEMONTID:0001238] Carboxylic acid esters

*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
NPO28037.2 Isodon shikokiana var. occidentalis Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28037.2 Isodon shikokiana var. occidentalis Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]

☑ 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
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 14581.0 nM PMID[533148]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 89125.1 nM PMID[533148]
NPT3736 Individual Protein Latent membrane protein 1 Human herpesvirus 4 (strain B95-8) AC50 = 11289.0 nM PMID[533148]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 35481.3 nM PMID[533148]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 2818.4 nM PMID[533148]
NPT71 Cell Line HEK293 Homo sapiens AC50 = 5720.0 nM PMID[533148]
NPT3736 Individual Protein Latent membrane protein 1 Human herpesvirus 4 (strain B95-8) AC50 = 5137.0 nM PMID[533148]
NPT71 Cell Line HEK293 Homo sapiens Potency n.a. 12589.3 nM PMID[533148]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 2529.3 nM PMID[533149]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 1399.59 nM PMID[533149]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 2642.41 nM PMID[533149]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 1122.02 nM PMID[533149]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 2060.63 nM PMID[533149]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 4216.97 nM PMID[533149]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 287.74 nM PMID[533149]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 3033.89 nM PMID[533149]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2098.94 nM PMID[533149]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 1815.52 nM PMID[533149]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 2365.92 nM PMID[533149]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 351.56 nM PMID[533149]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 3184.2 nM PMID[533149]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 3732.5 nM PMID[533149]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 660.69 nM PMID[533149]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 8452.79 nM PMID[533149]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 2930.89 nM PMID[533149]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 4111.5 nM PMID[533149]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 3810.66 nM PMID[533149]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 5321.08 nM PMID[533149]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 3580.96 nM PMID[533149]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 346.74 nM PMID[533149]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 4645.15 nM PMID[533149]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 5861.38 nM PMID[533149]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 2421.03 nM PMID[533149]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 3311.31 nM PMID[533149]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 522.4 nM PMID[533149]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 2642.41 nM PMID[533149]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 12189.9 nM PMID[533149]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 2529.3 nM PMID[533149]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 2172.7 nM PMID[533149]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1140.25 nM PMID[533149]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 3076.1 nM PMID[533149]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 5000.35 nM PMID[533149]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 4375.22 nM PMID[533149]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 8317.64 nM PMID[533149]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 1945.36 nM PMID[533149]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 552.08 nM PMID[533149]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 3404.08 nM PMID[533149]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1599.56 nM PMID[533149]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 797.99 nM PMID[533149]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 3908.41 nM PMID[533149]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 7194.49 nM PMID[533149]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 3741.11 nM PMID[533149]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 8953.65 nM PMID[533149]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 2269.86 nM PMID[533149]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 1625.55 nM PMID[533149]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 1757.92 nM PMID[533149]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 3243.4 nM PMID[533149]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 9311.08 nM PMID[533149]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 3033.89 nM PMID[533149]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 3580.96 nM PMID[533149]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 3732.5 nM PMID[533149]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 3013.01 nM PMID[533149]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 391.74 nM PMID[533149]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 7762.47 nM PMID[533149]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 1348.96 nM PMID[533149]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 3655.95 nM PMID[533149]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 2233.57 nM PMID[533149]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 770.9 nM PMID[533149]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 9200.0 nM PMID[533148]
NPT477 Individual Protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 11220.2 nM PMID[533148]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2059.6 nM PMID[533148]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 28183.8 nM PMID[533148]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 891.3 nM PMID[533148]
NPT157 Individual Protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 5011.9 nM PMID[533148]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 5623.4 nM PMID[533148]
NPT1043 Individual Protein Glycoprotein hormones alpha chain Homo sapiens Potency n.a. 316.2 nM PMID[533148]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 2059.6 nM PMID[533148]
NPT1283 Individual Protein Paired box protein Pax-8 Homo sapiens AC50 < 260.0 nM PMID[533148]
NPT1283 Individual Protein Paired box protein Pax-8 Homo sapiens AC50 = 1430.0 nM PMID[533148]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 15848.9 nM PMID[533148]
NPT2 Others Unspecified Potency n.a. 23109.3 nM PMID[533148]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 50118.7 nM PMID[533148]
NPT2 Others Unspecified Potency n.a. 2238.7 nM PMID[533148]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[533148]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[533148]
NPT2 Others Unspecified Potency n.a. 5804.8 nM PMID[533148]
NPT920 Individual Protein Alpha-synuclein Homo sapiens Potency n.a. 35481.3 nM PMID[533148]
NPT2 Others Unspecified Potency n.a. 2511.9 nM PMID[533148]
NPT2 Others Unspecified Potency n.a. 3981.1 nM PMID[533148]
NPT2 Others Unspecified Potency n.a. 7943.3 nM PMID[533148]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. CC50 n.a. 4830.0 nM PMID[533148]

☑ 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 NPC306856 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9053 High Similarity NPC184065
0.8586 High Similarity NPC471041
0.8515 High Similarity NPC95899
0.85 High Similarity NPC471412
0.8469 Intermediate Similarity NPC202833
0.8469 Intermediate Similarity NPC242848
0.8469 Intermediate Similarity NPC234993
0.8469 Intermediate Similarity NPC134072
0.84 Intermediate Similarity NPC117685
0.84 Intermediate Similarity NPC471413
0.8384 Intermediate Similarity NPC474343
0.8333 Intermediate Similarity NPC232202
0.8318 Intermediate Similarity NPC472926
0.8317 Intermediate Similarity NPC472924
0.8269 Intermediate Similarity NPC472925
0.8265 Intermediate Similarity NPC148463
0.8235 Intermediate Similarity NPC162973
0.8218 Intermediate Similarity NPC476274
0.82 Intermediate Similarity NPC287668
0.819 Intermediate Similarity NPC89171
0.819 Intermediate Similarity NPC476802
0.8182 Intermediate Similarity NPC470232
0.8173 Intermediate Similarity NPC123726
0.8173 Intermediate Similarity NPC284365
0.8163 Intermediate Similarity NPC139692
0.8155 Intermediate Similarity NPC478057
0.8155 Intermediate Similarity NPC159442
0.8144 Intermediate Similarity NPC51486
0.8137 Intermediate Similarity NPC475099
0.8137 Intermediate Similarity NPC224720
0.8137 Intermediate Similarity NPC476240
0.8137 Intermediate Similarity NPC81530
0.8137 Intermediate Similarity NPC476223
0.8125 Intermediate Similarity NPC104560
0.8119 Intermediate Similarity NPC316598
0.8119 Intermediate Similarity NPC23364
0.8113 Intermediate Similarity NPC475941
0.8113 Intermediate Similarity NPC474901
0.8113 Intermediate Similarity NPC474243
0.81 Intermediate Similarity NPC329910
0.81 Intermediate Similarity NPC29952
0.8091 Intermediate Similarity NPC472927
0.8081 Intermediate Similarity NPC470385
0.8081 Intermediate Similarity NPC53685
0.8081 Intermediate Similarity NPC475118
0.8081 Intermediate Similarity NPC57117
0.8081 Intermediate Similarity NPC470386
0.8077 Intermediate Similarity NPC96268
0.8061 Intermediate Similarity NPC177037
0.8061 Intermediate Similarity NPC472814
0.8061 Intermediate Similarity NPC473675
0.8058 Intermediate Similarity NPC136289
0.8056 Intermediate Similarity NPC90952
0.8039 Intermediate Similarity NPC476299
0.8039 Intermediate Similarity NPC470074
0.8039 Intermediate Similarity NPC474718
0.8039 Intermediate Similarity NPC477521
0.8039 Intermediate Similarity NPC472972
0.8039 Intermediate Similarity NPC474012
0.8039 Intermediate Similarity NPC476767
0.8037 Intermediate Similarity NPC179642
0.8037 Intermediate Similarity NPC153036
0.802 Intermediate Similarity NPC253826
0.8019 Intermediate Similarity NPC476479
0.8019 Intermediate Similarity NPC189075
0.8019 Intermediate Similarity NPC275539
0.8 Intermediate Similarity NPC469607
0.8 Intermediate Similarity NPC470229
0.8 Intermediate Similarity NPC134067
0.7982 Intermediate Similarity NPC472757
0.7981 Intermediate Similarity NPC282233
0.7981 Intermediate Similarity NPC72151
0.7981 Intermediate Similarity NPC95585
0.798 Intermediate Similarity NPC115021
0.7965 Intermediate Similarity NPC472401
0.7963 Intermediate Similarity NPC475937
0.7963 Intermediate Similarity NPC472928
0.7963 Intermediate Similarity NPC188738
0.7963 Intermediate Similarity NPC158523
0.7961 Intermediate Similarity NPC282524
0.7959 Intermediate Similarity NPC230332
0.7946 Intermediate Similarity NPC472933
0.7944 Intermediate Similarity NPC273433
0.7941 Intermediate Similarity NPC474793
0.7941 Intermediate Similarity NPC471932
0.7941 Intermediate Similarity NPC114274
0.7941 Intermediate Similarity NPC478056
0.7941 Intermediate Similarity NPC471038
0.7925 Intermediate Similarity NPC110496
0.7925 Intermediate Similarity NPC230541
0.7921 Intermediate Similarity NPC21302
0.7921 Intermediate Similarity NPC470387
0.7921 Intermediate Similarity NPC118159
0.7921 Intermediate Similarity NPC7124
0.7921 Intermediate Similarity NPC471039
0.7921 Intermediate Similarity NPC250757
0.7921 Intermediate Similarity NPC301534
0.7921 Intermediate Similarity NPC11396
0.7917 Intermediate Similarity NPC198761
0.7917 Intermediate Similarity NPC194417
0.7917 Intermediate Similarity NPC202394
0.7917 Intermediate Similarity NPC472985
0.7917 Intermediate Similarity NPC472986
0.7909 Intermediate Similarity NPC470953
0.7909 Intermediate Similarity NPC472400
0.7905 Intermediate Similarity NPC118911
0.79 Intermediate Similarity NPC90453
0.79 Intermediate Similarity NPC47853
0.79 Intermediate Similarity NPC250075
0.79 Intermediate Similarity NPC471040
0.7895 Intermediate Similarity NPC19464
0.789 Intermediate Similarity NPC277769
0.789 Intermediate Similarity NPC269530
0.789 Intermediate Similarity NPC475970
0.789 Intermediate Similarity NPC4573
0.789 Intermediate Similarity NPC476801
0.7885 Intermediate Similarity NPC293753
0.7885 Intermediate Similarity NPC478156
0.7885 Intermediate Similarity NPC295791
0.7885 Intermediate Similarity NPC164551
0.7885 Intermediate Similarity NPC320447
0.7879 Intermediate Similarity NPC198242
0.7879 Intermediate Similarity NPC473944
0.7879 Intermediate Similarity NPC472978
0.7879 Intermediate Similarity NPC211403
0.7876 Intermediate Similarity NPC476962
0.787 Intermediate Similarity NPC286880
0.787 Intermediate Similarity NPC478209
0.7864 Intermediate Similarity NPC47024
0.7864 Intermediate Similarity NPC472644
0.7864 Intermediate Similarity NPC266955
0.7864 Intermediate Similarity NPC251680
0.7864 Intermediate Similarity NPC54705
0.7857 Intermediate Similarity NPC5509
0.7857 Intermediate Similarity NPC472973
0.7857 Intermediate Similarity NPC21326
0.785 Intermediate Similarity NPC102843
0.785 Intermediate Similarity NPC476765
0.785 Intermediate Similarity NPC19412
0.7843 Intermediate Similarity NPC53844
0.7843 Intermediate Similarity NPC475709
0.7843 Intermediate Similarity NPC134454
0.7843 Intermediate Similarity NPC17326
0.7843 Intermediate Similarity NPC254496
0.7843 Intermediate Similarity NPC320306
0.7838 Intermediate Similarity NPC471127
0.7838 Intermediate Similarity NPC154363
0.7838 Intermediate Similarity NPC234858
0.783 Intermediate Similarity NPC102352
0.783 Intermediate Similarity NPC478208
0.783 Intermediate Similarity NPC1679
0.7826 Intermediate Similarity NPC472399
0.7822 Intermediate Similarity NPC209355
0.7822 Intermediate Similarity NPC183012
0.7822 Intermediate Similarity NPC266899
0.7818 Intermediate Similarity NPC25909
0.7818 Intermediate Similarity NPC71889
0.7818 Intermediate Similarity NPC962
0.7812 Intermediate Similarity NPC261380
0.7812 Intermediate Similarity NPC52628
0.781 Intermediate Similarity NPC110989
0.781 Intermediate Similarity NPC275583
0.781 Intermediate Similarity NPC471938
0.781 Intermediate Similarity NPC159533
0.781 Intermediate Similarity NPC90177
0.781 Intermediate Similarity NPC312900
0.7788 Intermediate Similarity NPC115862
0.7788 Intermediate Similarity NPC236585
0.7788 Intermediate Similarity NPC268958
0.7788 Intermediate Similarity NPC52899
0.7788 Intermediate Similarity NPC46848
0.7788 Intermediate Similarity NPC289148
0.7788 Intermediate Similarity NPC118174
0.7788 Intermediate Similarity NPC97435
0.7788 Intermediate Similarity NPC308824
0.7788 Intermediate Similarity NPC111292
0.7788 Intermediate Similarity NPC115899
0.7788 Intermediate Similarity NPC472643
0.7788 Intermediate Similarity NPC163963
0.7788 Intermediate Similarity NPC242666
0.7778 Intermediate Similarity NPC42662
0.7778 Intermediate Similarity NPC71533
0.7778 Intermediate Similarity NPC158488
0.7778 Intermediate Similarity NPC153239
0.7778 Intermediate Similarity NPC20192
0.7778 Intermediate Similarity NPC141350
0.7778 Intermediate Similarity NPC106510
0.7768 Intermediate Similarity NPC472934
0.7768 Intermediate Similarity NPC469684
0.7768 Intermediate Similarity NPC156252
0.7768 Intermediate Similarity NPC10721
0.7767 Intermediate Similarity NPC141191
0.7767 Intermediate Similarity NPC471717
0.7767 Intermediate Similarity NPC124512
0.7767 Intermediate Similarity NPC278386
0.7767 Intermediate Similarity NPC159763
0.7767 Intermediate Similarity NPC57079
0.7767 Intermediate Similarity NPC216478
0.7767 Intermediate Similarity NPC222011
0.7767 Intermediate Similarity NPC108368

  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 NPC306856 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
0.7864 Intermediate Similarity NPD7639 Approved
0.7864 Intermediate Similarity NPD7640 Approved
0.7767 Intermediate Similarity NPD4225 Approved
0.7767 Intermediate Similarity NPD7638 Approved
0.7624 Intermediate Similarity NPD5779 Approved
0.7624 Intermediate Similarity NPD5778 Approved
0.7476 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD5697 Approved
0.7414 Intermediate Similarity NPD6319 Approved
0.7379 Intermediate Similarity NPD7748 Approved
0.7364 Intermediate Similarity NPD6011 Approved
0.7364 Intermediate Similarity NPD6899 Approved
0.7364 Intermediate Similarity NPD6881 Approved
0.7353 Intermediate Similarity NPD6079 Approved
0.7353 Intermediate Similarity NPD7515 Phase 2
0.7345 Intermediate Similarity NPD4632 Approved
0.7339 Intermediate Similarity NPD7128 Approved
0.7339 Intermediate Similarity NPD5739 Approved
0.7339 Intermediate Similarity NPD6675 Approved
0.7339 Intermediate Similarity NPD6402 Approved
0.7327 Intermediate Similarity NPD5328 Approved
0.732 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD7115 Discovery
0.7297 Intermediate Similarity NPD6012 Approved
0.7297 Intermediate Similarity NPD6013 Approved
0.7297 Intermediate Similarity NPD6014 Approved
0.7273 Intermediate Similarity NPD5701 Approved
0.7255 Intermediate Similarity NPD5785 Approved
0.7238 Intermediate Similarity NPD5221 Approved
0.7238 Intermediate Similarity NPD5222 Approved
0.7238 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD6371 Approved
0.7232 Intermediate Similarity NPD7102 Approved
0.7232 Intermediate Similarity NPD6883 Approved
0.7232 Intermediate Similarity NPD7290 Approved
0.7222 Intermediate Similarity NPD7632 Discontinued
0.7222 Intermediate Similarity NPD5211 Phase 2
0.7207 Intermediate Similarity NPD6686 Approved
0.7207 Intermediate Similarity NPD7320 Approved
0.72 Intermediate Similarity NPD3618 Phase 1
0.7184 Intermediate Similarity NPD6411 Approved
0.7182 Intermediate Similarity NPD6008 Approved
0.717 Intermediate Similarity NPD5173 Approved
0.717 Intermediate Similarity NPD7902 Approved
0.7168 Intermediate Similarity NPD6847 Approved
0.7168 Intermediate Similarity NPD6649 Approved
0.7168 Intermediate Similarity NPD6650 Approved
0.7168 Intermediate Similarity NPD8130 Phase 1
0.7168 Intermediate Similarity NPD6617 Approved
0.7168 Intermediate Similarity NPD6869 Approved
0.7167 Intermediate Similarity NPD7492 Approved
0.7155 Intermediate Similarity NPD6009 Approved
0.7143 Intermediate Similarity NPD6373 Approved
0.7143 Intermediate Similarity NPD6372 Approved
0.7129 Intermediate Similarity NPD3573 Approved
0.7119 Intermediate Similarity NPD6054 Approved
0.7107 Intermediate Similarity NPD6616 Approved
0.7105 Intermediate Similarity NPD8297 Approved
0.7105 Intermediate Similarity NPD6882 Approved
0.71 Intermediate Similarity NPD5363 Approved
0.71 Intermediate Similarity NPD1694 Approved
0.7091 Intermediate Similarity NPD5141 Approved
0.708 Intermediate Similarity NPD4634 Approved
0.7075 Intermediate Similarity NPD4697 Phase 3
0.7059 Intermediate Similarity NPD6015 Approved
0.7059 Intermediate Similarity NPD6016 Approved
0.7059 Intermediate Similarity NPD5983 Phase 2
0.7049 Intermediate Similarity NPD7078 Approved
0.7048 Intermediate Similarity NPD5282 Discontinued
0.7037 Intermediate Similarity NPD5286 Approved
0.7037 Intermediate Similarity NPD4696 Approved
0.7037 Intermediate Similarity NPD5285 Approved
0.703 Intermediate Similarity NPD5786 Approved
0.7019 Intermediate Similarity NPD7637 Suspended
0.7019 Intermediate Similarity NPD7983 Approved
0.7018 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD4755 Approved
0.7 Intermediate Similarity NPD6370 Approved
0.7 Intermediate Similarity NPD5988 Approved
0.6992 Remote Similarity NPD7736 Approved
0.6991 Remote Similarity NPD4061 Clinical (unspecified phase)
0.699 Remote Similarity NPD5764 Clinical (unspecified phase)
0.699 Remote Similarity NPD6101 Approved
0.6975 Remote Similarity NPD6059 Approved
0.6972 Remote Similarity NPD5223 Approved
0.6952 Remote Similarity NPD6399 Phase 3
0.6942 Remote Similarity NPD7604 Phase 2
0.6942 Remote Similarity NPD8328 Phase 3
0.6935 Remote Similarity NPD7319 Approved
0.6923 Remote Similarity NPD6868 Approved
0.6923 Remote Similarity NPD6274 Approved
0.6911 Remote Similarity NPD8293 Discontinued
0.6909 Remote Similarity NPD5225 Approved
0.6909 Remote Similarity NPD4633 Approved
0.6909 Remote Similarity NPD5224 Approved
0.6909 Remote Similarity NPD5226 Approved
0.6907 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6903 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6887 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6887 Remote Similarity NPD7900 Approved
0.6881 Remote Similarity NPD4700 Approved
0.6864 Remote Similarity NPD6317 Approved
0.6863 Remote Similarity NPD7146 Approved
0.6863 Remote Similarity NPD6684 Approved
0.6863 Remote Similarity NPD7334 Approved
0.6863 Remote Similarity NPD6409 Approved
0.6863 Remote Similarity NPD5330 Approved
0.6863 Remote Similarity NPD7521 Approved
0.6863 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6852 Remote Similarity NPD6083 Phase 2
0.6852 Remote Similarity NPD6084 Phase 2
0.6847 Remote Similarity NPD5174 Approved
0.6847 Remote Similarity NPD5175 Approved
0.6832 Remote Similarity NPD3666 Approved
0.6832 Remote Similarity NPD3133 Approved
0.6832 Remote Similarity NPD3665 Phase 1
0.6829 Remote Similarity NPD7507 Approved
0.6829 Remote Similarity NPD6336 Discontinued
0.6822 Remote Similarity NPD5695 Phase 3
0.6818 Remote Similarity NPD5344 Discontinued
0.6807 Remote Similarity NPD6313 Approved
0.6807 Remote Similarity NPD6314 Approved
0.6807 Remote Similarity NPD6335 Approved
0.68 Remote Similarity NPD4269 Approved
0.68 Remote Similarity NPD5209 Approved
0.68 Remote Similarity NPD4270 Approved
0.68 Remote Similarity NPD3667 Approved
0.6792 Remote Similarity NPD4202 Approved
0.6783 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6765 Remote Similarity NPD1696 Phase 3
0.6762 Remote Similarity NPD46 Approved
0.6762 Remote Similarity NPD6698 Approved
0.6759 Remote Similarity NPD7839 Suspended
0.675 Remote Similarity NPD7101 Approved
0.675 Remote Similarity NPD7100 Approved
0.6733 Remote Similarity NPD5362 Discontinued
0.6733 Remote Similarity NPD7154 Phase 3
0.6731 Remote Similarity NPD5737 Approved
0.6731 Remote Similarity NPD6903 Approved
0.6731 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6672 Approved
0.6699 Remote Similarity NPD4519 Discontinued
0.6699 Remote Similarity NPD4623 Approved
0.6699 Remote Similarity NPD5279 Phase 3
0.6696 Remote Similarity NPD4754 Approved
0.6667 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6053 Discontinued
0.6667 Remote Similarity NPD6412 Phase 2
0.6667 Remote Similarity NPD4786 Approved
0.6639 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6636 Remote Similarity NPD5696 Approved
0.6634 Remote Similarity NPD6435 Approved
0.6609 Remote Similarity NPD5168 Approved
0.6609 Remote Similarity NPD4730 Approved
0.6609 Remote Similarity NPD4729 Approved
0.6609 Remote Similarity NPD5128 Approved
0.6602 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6602 Remote Similarity NPD7520 Clinical (unspecified phase)
0.66 Remote Similarity NPD4695 Discontinued
0.66 Remote Similarity NPD4252 Approved
0.6587 Remote Similarity NPD6033 Approved
0.6579 Remote Similarity NPD4767 Approved
0.6579 Remote Similarity NPD4768 Approved
0.6577 Remote Similarity NPD6648 Approved
0.6542 Remote Similarity NPD8034 Phase 2
0.6542 Remote Similarity NPD8035 Phase 2
0.6535 Remote Similarity NPD5369 Approved
0.6522 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6515 Remote Similarity NPD6334 Approved
0.6515 Remote Similarity NPD6333 Approved
0.6514 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6509 Remote Similarity NPD4753 Phase 2
0.6504 Remote Similarity NPD6908 Approved
0.6504 Remote Similarity NPD6909 Approved
0.6496 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6496 Remote Similarity NPD5251 Approved
0.6496 Remote Similarity NPD5249 Phase 3
0.6496 Remote Similarity NPD5248 Approved
0.6496 Remote Similarity NPD5247 Approved
0.6496 Remote Similarity NPD5250 Approved
0.6496 Remote Similarity NPD5135 Approved
0.6496 Remote Similarity NPD5169 Approved
0.6446 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6441 Remote Similarity NPD5215 Approved
0.6441 Remote Similarity NPD5216 Approved
0.6441 Remote Similarity NPD5217 Approved
0.6441 Remote Similarity NPD5127 Approved
0.6436 Remote Similarity NPD5368 Approved
0.641 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6389 Remote Similarity NPD5284 Approved
0.6389 Remote Similarity NPD5693 Phase 1
0.6389 Remote Similarity NPD5281 Approved
0.6381 Remote Similarity NPD4249 Approved
0.6371 Remote Similarity NPD8513 Phase 3
0.6371 Remote Similarity NPD8516 Approved
0.6371 Remote Similarity NPD8515 Approved
0.6371 Remote Similarity NPD8517 Approved
0.6364 Remote Similarity NPD5210 Approved
0.6364 Remote Similarity NPD4629 Approved
0.6357 Remote Similarity NPD6914 Discontinued

  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