Structure

Physi-Chem Properties

Molecular Weight:  246.13
Volume:  258.152
LogP:  1.912
LogD:  1.822
LogS:  -2.908
# Rotatable Bonds:  0
TPSA:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.374
Synthetic Accessibility Score:  4.497
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:  -4.567
MDCK Permeability:  2.6988192985299975e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.072
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.94
Plasma Protein Binding (PPB):  80.70904541015625%
Volume Distribution (VD):  1.169
Pgp-substrate:  21.756813049316406%

ADMET: Metabolism

CYP1A2-inhibitor:  0.312
CYP1A2-substrate:  0.687
CYP2C19-inhibitor:  0.431
CYP2C19-substrate:  0.851
CYP2C9-inhibitor:  0.22
CYP2C9-substrate:  0.521
CYP2D6-inhibitor:  0.054
CYP2D6-substrate:  0.246
CYP3A4-inhibitor:  0.638
CYP3A4-substrate:  0.441

ADMET: Excretion

Clearance (CL):  15.541
Half-life (T1/2):  0.316

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.089
Drug-inuced Liver Injury (DILI):  0.319
AMES Toxicity:  0.051
Rat Oral Acute Toxicity:  0.892
Maximum Recommended Daily Dose:  0.259
Skin Sensitization:  0.066
Carcinogencity:  0.931
Eye Corrosion:  0.035
Eye Irritation:  0.196
Respiratory Toxicity:  0.967

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

  Natural Product: NPC33570

Natural Product ID:  NPC33570
Common Name*:   6,9A-Dimethyl-3-Methylidene-3A,4,5,6,6A,9B-Hexahydroazuleno[8,7-B]Furan-2,9-Dione
IUPAC Name:   6,9a-dimethyl-3-methylidene-3a,4,5,6,6a,9b-hexahydroazuleno[8,7-b]furan-2,9-dione
Synonyms:  
Standard InCHIKey:  IFXGCKRDLITNAU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H18O3/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(15)16/h6-8,10-11,13H,2,4-5H2,1,3H3
SMILES:  CC1CCC2C(C3(C1C=CC3=O)C)OC(=O)C2=C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1730820
PubChem CID:   257272
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:0002046] Ambrosanolides and secoambrosanolides

*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
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/JMPR.9000078]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28156114]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO12932 Hymenoclea salsola n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12932 Hymenoclea salsola n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12932 Hymenoclea salsola n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12932 Hymenoclea salsola n.a. n.a. n.a. 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
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 18356.4 nM PMID[508892]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[508892]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 19952.6 nM PMID[508892]
NPT71 Cell Line HEK293 Homo sapiens Potency n.a. 31622.8 nM PMID[508892]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 3334.26 nM PMID[508893]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 1774.19 nM PMID[508893]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 1729.82 nM PMID[508893]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 3250.87 nM PMID[508893]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 4753.35 nM PMID[508893]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 4102.04 nM PMID[508893]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 2529.3 nM PMID[508893]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 1412.54 nM PMID[508893]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2741.57 nM PMID[508893]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 3334.26 nM PMID[508893]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 2500.35 nM PMID[508893]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 2477.42 nM PMID[508893]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 12105.98 nM PMID[508893]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 1218.99 nM PMID[508893]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 2460.37 nM PMID[508893]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 15452.54 nM PMID[508893]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 1409.29 nM PMID[508893]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 11857.69 nM PMID[508893]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 2055.89 nM PMID[508893]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 4528.98 nM PMID[508893]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 2192.8 nM PMID[508893]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 4083.19 nM PMID[508893]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 14723.13 nM PMID[508893]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 1506.61 nM PMID[508893]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 3054.92 nM PMID[508893]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 1803.02 nM PMID[508893]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 3357.38 nM PMID[508893]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 891.25 nM PMID[508893]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 2162.72 nM PMID[508893]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 3288.52 nM PMID[508893]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 1954.34 nM PMID[508893]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 1807.17 nM PMID[508893]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 4140.0 nM PMID[508893]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 6760.83 nM PMID[508893]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1931.97 nM PMID[508893]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 1633.05 nM PMID[508893]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 3614.1 nM PMID[508893]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 4385.31 nM PMID[508893]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 11967.41 nM PMID[508893]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 7762.47 nM PMID[508893]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 8147.04 nM PMID[508893]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 1819.7 nM PMID[508893]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1741.81 nM PMID[508893]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 8609.94 nM PMID[508893]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 8790.23 nM PMID[508893]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 4487.45 nM PMID[508893]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 3917.42 nM PMID[508893]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 1581.25 nM PMID[508893]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 4216.97 nM PMID[508893]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 27989.81 nM PMID[508893]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 2454.71 nM PMID[508893]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 4841.72 nM PMID[508893]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 2971.67 nM PMID[508893]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 1794.73 nM PMID[508893]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 6807.69 nM PMID[508893]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 1733.8 nM PMID[508893]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 6137.62 nM PMID[508893]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 5457.58 nM PMID[508893]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 2564.48 nM PMID[508893]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 1849.27 nM PMID[508893]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 1972.42 nM PMID[508893]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 3140.51 nM PMID[508893]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 1887.99 nM PMID[508893]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 1336.6 nM PMID[508893]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 2023.02 nM PMID[508893]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 3749.73 nM PMID[508893]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 2046.44 nM PMID[508893]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 1836.54 nM PMID[508893]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 2167.7 nM PMID[508893]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 6652.73 nM PMID[508893]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2059.6 nM PMID[508892]
NPT477 Individual Protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 11220.2 nM PMID[508892]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 6513.1 nM PMID[508892]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 31622.8 nM PMID[508892]
NPT157 Individual Protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 11220.2 nM PMID[508892]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 3162.3 nM PMID[508892]
NPT1043 Individual Protein Glycoprotein hormones alpha chain Homo sapiens Potency n.a. 1778.3 nM PMID[508892]
NPT1486 Individual Protein Probable global transcription activator SNF2L2 Homo sapiens EC50 > 91243.0 nM PMID[508892]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 2909.3 nM PMID[508892]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 3264.3 nM PMID[508892]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 125892.5 nM PMID[508892]
NPT21702 PROTEIN-PROTEIN INTERACTION Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 63095.7 nM PMID[508892]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 44668.4 nM PMID[508892]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 44668.4 nM PMID[508892]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 14125.4 nM PMID[508892]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[508892]
NPT2 Others Unspecified Potency n.a. 50118.7 nM PMID[508892]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[508892]
NPT2 Others Unspecified Potency n.a. 31622.8 nM PMID[508892]
NPT2 Others Unspecified Potency n.a. 20596.2 nM PMID[508892]
NPT2 Others Unspecified AbsAC35 = 15.52 uM PMID[508892]
NPT35 Others n.a. EC50 > 91243.0 nM PMID[508892]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 29092.9 nM PMID[508892]
NPT2 Others Unspecified Max_Activity = 26.0 uM PMID[508892]
NPT2 Others Unspecified AbsAC35_uM = 7.41 uM PMID[508892]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 84921.4 nM PMID[508892]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[508892]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. AbsAC35_uM = 9.29 uM PMID[508892]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. AbsAC35_uM = 8.71 uM PMID[508892]
NPT2 Others Unspecified Potency n.a. 39810.7 nM PMID[508892]

☑ 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 NPC33570 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 NPC21471
0.9506 High Similarity NPC161957
0.95 High Similarity NPC215294
0.9294 High Similarity NPC70595
0.9294 High Similarity NPC150978
0.9294 High Similarity NPC123177
0.9294 High Similarity NPC74103
0.9259 High Similarity NPC39588
0.9176 High Similarity NPC253144
0.9125 High Similarity NPC69271
0.9125 High Similarity NPC74673
0.908 High Similarity NPC167219
0.907 High Similarity NPC284185
0.8977 High Similarity NPC48803
0.8977 High Similarity NPC90121
0.8977 High Similarity NPC275960
0.8977 High Similarity NPC193645
0.8889 High Similarity NPC302426
0.8889 High Similarity NPC276356
0.8889 High Similarity NPC6823
0.8778 High Similarity NPC169205
0.8706 High Similarity NPC70422
0.8706 High Similarity NPC104961
0.8706 High Similarity NPC70555
0.8681 High Similarity NPC141191
0.8681 High Similarity NPC54843
0.8667 High Similarity NPC185553
0.8659 High Similarity NPC223904
0.8554 High Similarity NPC35089
0.8554 High Similarity NPC10276
0.8537 High Similarity NPC472965
0.8537 High Similarity NPC264227
0.8537 High Similarity NPC63649
0.8537 High Similarity NPC182550
0.8519 High Similarity NPC15975
0.8519 High Similarity NPC65603
0.8519 High Similarity NPC195785
0.85 High Similarity NPC193351
0.85 High Similarity NPC138408
0.85 High Similarity NPC226669
0.8488 Intermediate Similarity NPC107787
0.8471 Intermediate Similarity NPC115786
0.8434 Intermediate Similarity NPC293418
0.8434 Intermediate Similarity NPC290508
0.8434 Intermediate Similarity NPC73052
0.8427 Intermediate Similarity NPC261607
0.8427 Intermediate Similarity NPC300312
0.8427 Intermediate Similarity NPC111114
0.8409 Intermediate Similarity NPC52198
0.8409 Intermediate Similarity NPC117405
0.8372 Intermediate Similarity NPC78089
0.8295 Intermediate Similarity NPC215831
0.8293 Intermediate Similarity NPC476794
0.8293 Intermediate Similarity NPC470240
0.8276 Intermediate Similarity NPC238593
0.8272 Intermediate Similarity NPC155587
0.825 Intermediate Similarity NPC472956
0.8229 Intermediate Similarity NPC203659
0.8211 Intermediate Similarity NPC225353
0.8202 Intermediate Similarity NPC73995
0.8193 Intermediate Similarity NPC299235
0.8182 Intermediate Similarity NPC201658
0.8182 Intermediate Similarity NPC478144
0.8171 Intermediate Similarity NPC266159
0.8171 Intermediate Similarity NPC235906
0.8171 Intermediate Similarity NPC472967
0.8161 Intermediate Similarity NPC177932
0.8148 Intermediate Similarity NPC143979
0.8148 Intermediate Similarity NPC320537
0.814 Intermediate Similarity NPC318468
0.814 Intermediate Similarity NPC54468
0.8125 Intermediate Similarity NPC110989
0.8118 Intermediate Similarity NPC301477
0.8118 Intermediate Similarity NPC281949
0.8118 Intermediate Similarity NPC25684
0.8118 Intermediate Similarity NPC255580
0.8118 Intermediate Similarity NPC39411
0.8111 Intermediate Similarity NPC62815
0.8095 Intermediate Similarity NPC470244
0.8095 Intermediate Similarity NPC470239
0.809 Intermediate Similarity NPC91248
0.8072 Intermediate Similarity NPC41780
0.8072 Intermediate Similarity NPC187568
0.8072 Intermediate Similarity NPC208223
0.8043 Intermediate Similarity NPC289004
0.8023 Intermediate Similarity NPC173609
0.8023 Intermediate Similarity NPC178676
0.8 Intermediate Similarity NPC168679
0.8 Intermediate Similarity NPC268298
0.8 Intermediate Similarity NPC4986
0.8 Intermediate Similarity NPC12872
0.7979 Intermediate Similarity NPC170143
0.7979 Intermediate Similarity NPC108475
0.7979 Intermediate Similarity NPC213947
0.7978 Intermediate Similarity NPC72513
0.7978 Intermediate Similarity NPC478145
0.7976 Intermediate Similarity NPC128276
0.7976 Intermediate Similarity NPC472960
0.7976 Intermediate Similarity NPC253749
0.7957 Intermediate Similarity NPC304886
0.7955 Intermediate Similarity NPC125290
0.7955 Intermediate Similarity NPC110405
0.7952 Intermediate Similarity NPC123360
0.7935 Intermediate Similarity NPC135776
0.7931 Intermediate Similarity NPC22611
0.7931 Intermediate Similarity NPC193198
0.7931 Intermediate Similarity NPC475947
0.7927 Intermediate Similarity NPC469641
0.7927 Intermediate Similarity NPC469643
0.7927 Intermediate Similarity NPC476355
0.7912 Intermediate Similarity NPC129419
0.7912 Intermediate Similarity NPC152467
0.7907 Intermediate Similarity NPC471325
0.7907 Intermediate Similarity NPC47635
0.7907 Intermediate Similarity NPC42470
0.7907 Intermediate Similarity NPC38642
0.7901 Intermediate Similarity NPC163003
0.7889 Intermediate Similarity NPC226863
0.7882 Intermediate Similarity NPC469690
0.7882 Intermediate Similarity NPC178277
0.7882 Intermediate Similarity NPC617
0.7875 Intermediate Similarity NPC296522
0.7875 Intermediate Similarity NPC144511
0.7865 Intermediate Similarity NPC38576
0.7865 Intermediate Similarity NPC64153
0.7865 Intermediate Similarity NPC279859
0.7857 Intermediate Similarity NPC57744
0.7857 Intermediate Similarity NPC122264
0.7849 Intermediate Similarity NPC477131
0.7841 Intermediate Similarity NPC156485
0.7841 Intermediate Similarity NPC475100
0.7841 Intermediate Similarity NPC165287
0.7826 Intermediate Similarity NPC131209
0.7826 Intermediate Similarity NPC133698
0.7826 Intermediate Similarity NPC286341
0.7826 Intermediate Similarity NPC191339
0.7805 Intermediate Similarity NPC58956
0.7805 Intermediate Similarity NPC269206
0.7805 Intermediate Similarity NPC295633
0.7778 Intermediate Similarity NPC237540
0.7778 Intermediate Similarity NPC472955
0.7766 Intermediate Similarity NPC474490
0.7753 Intermediate Similarity NPC215364
0.7753 Intermediate Similarity NPC96621
0.7753 Intermediate Similarity NPC165162
0.7753 Intermediate Similarity NPC235792
0.7742 Intermediate Similarity NPC200237
0.7742 Intermediate Similarity NPC473263
0.7742 Intermediate Similarity NPC475657
0.7742 Intermediate Similarity NPC473234
0.7742 Intermediate Similarity NPC473273
0.7742 Intermediate Similarity NPC60386
0.7742 Intermediate Similarity NPC308656
0.7742 Intermediate Similarity NPC153590
0.7738 Intermediate Similarity NPC472959
0.7732 Intermediate Similarity NPC171759
0.7732 Intermediate Similarity NPC474742
0.7717 Intermediate Similarity NPC469372
0.7717 Intermediate Similarity NPC106510
0.7717 Intermediate Similarity NPC145666
0.7717 Intermediate Similarity NPC71533
0.7711 Intermediate Similarity NPC140287
0.7701 Intermediate Similarity NPC325031
0.7701 Intermediate Similarity NPC141810
0.7701 Intermediate Similarity NPC475665
0.7692 Intermediate Similarity NPC469631
0.7692 Intermediate Similarity NPC471047
0.7692 Intermediate Similarity NPC469653
0.7692 Intermediate Similarity NPC475906
0.7692 Intermediate Similarity NPC469628
0.7683 Intermediate Similarity NPC129665
0.7674 Intermediate Similarity NPC469620
0.7674 Intermediate Similarity NPC150646
0.7674 Intermediate Similarity NPC270126
0.7667 Intermediate Similarity NPC67493
0.7667 Intermediate Similarity NPC284902
0.7667 Intermediate Similarity NPC304558
0.7667 Intermediate Similarity NPC261721
0.7667 Intermediate Similarity NPC56593
0.766 Intermediate Similarity NPC148463
0.766 Intermediate Similarity NPC198853
0.766 Intermediate Similarity NPC477130
0.766 Intermediate Similarity NPC53685
0.766 Intermediate Similarity NPC470697
0.766 Intermediate Similarity NPC477129
0.766 Intermediate Similarity NPC470010
0.766 Intermediate Similarity NPC470013
0.766 Intermediate Similarity NPC323008
0.766 Intermediate Similarity NPC262133
0.766 Intermediate Similarity NPC473331
0.7654 Intermediate Similarity NPC5714
0.7654 Intermediate Similarity NPC199557
0.7653 Intermediate Similarity NPC474747
0.7647 Intermediate Similarity NPC53581
0.7647 Intermediate Similarity NPC474760
0.7647 Intermediate Similarity NPC103987
0.764 Intermediate Similarity NPC238197
0.7634 Intermediate Similarity NPC472953
0.7619 Intermediate Similarity NPC244166
0.7614 Intermediate Similarity NPC246076

  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 NPC33570 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
0.8977 High Similarity NPD1698 Clinical (unspecified phase)
0.8161 Intermediate Similarity NPD1694 Approved
0.8 Intermediate Similarity NPD1695 Approved
0.7816 Intermediate Similarity NPD5209 Approved
0.7717 Intermediate Similarity NPD5785 Approved
0.7416 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD6371 Approved
0.7292 Intermediate Similarity NPD5282 Discontinued
0.7174 Intermediate Similarity NPD5363 Approved
0.7174 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4225 Approved
0.6947 Remote Similarity NPD6903 Approved
0.6923 Remote Similarity NPD5369 Approved
0.6915 Remote Similarity NPD6409 Approved
0.6915 Remote Similarity NPD7334 Approved
0.6915 Remote Similarity NPD5330 Approved
0.6915 Remote Similarity NPD6684 Approved
0.6915 Remote Similarity NPD7146 Approved
0.6915 Remote Similarity NPD7521 Approved
0.6848 Remote Similarity NPD4269 Approved
0.6848 Remote Similarity NPD4270 Approved
0.6818 Remote Similarity NPD8039 Approved
0.6804 Remote Similarity NPD5207 Approved
0.6774 Remote Similarity NPD5362 Discontinued
0.6771 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6737 Remote Similarity NPD5786 Approved
0.663 Remote Similarity NPD4252 Approved
0.6607 Remote Similarity NPD7115 Discovery
0.6598 Remote Similarity NPD6672 Approved
0.6598 Remote Similarity NPD5737 Approved
0.6596 Remote Similarity NPD7154 Phase 3
0.6593 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6566 Remote Similarity NPD6411 Approved
0.6566 Remote Similarity NPD5693 Phase 1
0.6548 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6535 Remote Similarity NPD6356 Clinical (unspecified phase)
0.65 Remote Similarity NPD6399 Phase 3
0.6495 Remote Similarity NPD3573 Approved
0.6449 Remote Similarity NPD6008 Approved
0.6436 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6436 Remote Similarity NPD7900 Approved
0.6436 Remote Similarity NPD6001 Approved
0.6364 Remote Similarity NPD6101 Approved
0.6364 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5779 Approved
0.6337 Remote Similarity NPD5778 Approved
0.6316 Remote Similarity NPD6435 Approved
0.63 Remote Similarity NPD46 Approved
0.63 Remote Similarity NPD6698 Approved
0.6289 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6275 Remote Similarity NPD7748 Approved
0.6263 Remote Similarity NPD5208 Approved
0.625 Remote Similarity NPD7902 Approved
0.6238 Remote Similarity NPD5694 Approved
0.6224 Remote Similarity NPD3618 Phase 1
0.6214 Remote Similarity NPD5695 Phase 3
0.62 Remote Similarity NPD6080 Approved
0.62 Remote Similarity NPD6673 Approved
0.62 Remote Similarity NPD6904 Approved
0.619 Remote Similarity NPD5696 Approved
0.619 Remote Similarity NPD7638 Approved
0.6186 Remote Similarity NPD3665 Phase 1
0.6186 Remote Similarity NPD3666 Approved
0.6186 Remote Similarity NPD3133 Approved
0.6182 Remote Similarity NPD6686 Approved
0.6146 Remote Similarity NPD3667 Approved
0.6139 Remote Similarity NPD7838 Discovery
0.6139 Remote Similarity NPD5692 Phase 3
0.6132 Remote Similarity NPD7640 Approved
0.6132 Remote Similarity NPD7639 Approved
0.6105 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6105 Remote Similarity NPD5368 Approved
0.6105 Remote Similarity NPD4695 Discontinued
0.6095 Remote Similarity NPD6084 Phase 2
0.6095 Remote Similarity NPD6083 Phase 2
0.6091 Remote Similarity NPD5697 Approved
0.6082 Remote Similarity NPD5332 Approved
0.6082 Remote Similarity NPD5331 Approved
0.6078 Remote Similarity NPD5284 Approved
0.6078 Remote Similarity NPD7637 Suspended
0.6078 Remote Similarity NPD7983 Approved
0.6078 Remote Similarity NPD5281 Approved
0.6078 Remote Similarity NPD6079 Approved
0.6078 Remote Similarity NPD6050 Approved
0.6078 Remote Similarity NPD7515 Phase 2
0.6061 Remote Similarity NPD6098 Approved
0.6061 Remote Similarity NPD5279 Phase 3
0.6061 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6061 Remote Similarity NPD4519 Discontinued
0.6061 Remote Similarity NPD4249 Approved
0.6061 Remote Similarity NPD4623 Approved
0.6042 Remote Similarity NPD4790 Discontinued
0.604 Remote Similarity NPD5370 Suspended
0.6036 Remote Similarity NPD6881 Approved
0.6036 Remote Similarity NPD6011 Approved
0.6036 Remote Similarity NPD6899 Approved
0.602 Remote Similarity NPD3668 Phase 3
0.602 Remote Similarity NPD4786 Approved
0.6018 Remote Similarity NPD6650 Approved
0.6018 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6018 Remote Similarity NPD6649 Approved
0.6 Remote Similarity NPD4250 Approved
0.6 Remote Similarity NPD4251 Approved
0.5982 Remote Similarity NPD6014 Approved
0.5982 Remote Similarity NPD6012 Approved
0.5982 Remote Similarity NPD6013 Approved
0.5965 Remote Similarity NPD6053 Discontinued
0.5963 Remote Similarity NPD6052 Approved
0.5955 Remote Similarity NPD229 Approved
0.5938 Remote Similarity NPD4819 Approved
0.5938 Remote Similarity NPD4821 Approved
0.5938 Remote Similarity NPD4820 Approved
0.5938 Remote Similarity NPD4822 Approved
0.5929 Remote Similarity NPD7290 Approved
0.5929 Remote Similarity NPD6883 Approved
0.5929 Remote Similarity NPD7102 Approved
0.5922 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5909 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5905 Remote Similarity NPD4629 Approved
0.5905 Remote Similarity NPD5210 Approved
0.59 Remote Similarity NPD5690 Phase 2
0.5895 Remote Similarity NPD4271 Approved
0.5895 Remote Similarity NPD4268 Approved
0.5893 Remote Similarity NPD7320 Approved
0.5888 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5882 Remote Similarity NPD6051 Approved
0.5882 Remote Similarity NPD5328 Approved
0.5877 Remote Similarity NPD8130 Phase 1
0.5877 Remote Similarity NPD6847 Approved
0.5877 Remote Similarity NPD6617 Approved
0.5877 Remote Similarity NPD6869 Approved
0.5876 Remote Similarity NPD857 Phase 3
0.5862 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5859 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5856 Remote Similarity NPD6402 Approved
0.5856 Remote Similarity NPD5739 Approved
0.5856 Remote Similarity NPD7128 Approved
0.5856 Remote Similarity NPD6675 Approved
0.5849 Remote Similarity NPD5222 Approved
0.5849 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5849 Remote Similarity NPD7839 Suspended
0.5849 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5849 Remote Similarity NPD5221 Approved
0.5841 Remote Similarity NPD6372 Approved
0.5841 Remote Similarity NPD6373 Approved
0.5833 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5826 Remote Similarity NPD6882 Approved
0.5826 Remote Similarity NPD8297 Approved
0.5824 Remote Similarity NPD4691 Approved
0.582 Remote Similarity NPD7492 Approved
0.5816 Remote Similarity NPD4221 Approved
0.5816 Remote Similarity NPD4223 Phase 3
0.5816 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5806 Remote Similarity NPD4058 Approved
0.5804 Remote Similarity NPD6614 Approved
0.5804 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5804 Remote Similarity NPD5701 Approved
0.58 Remote Similarity NPD1696 Phase 3
0.5794 Remote Similarity NPD5173 Approved
0.5789 Remote Similarity NPD4756 Discovery
0.5784 Remote Similarity NPD4518 Approved
0.5772 Remote Similarity NPD6616 Approved
0.5755 Remote Similarity NPD5654 Approved
0.575 Remote Similarity NPD6054 Approved
0.575 Remote Similarity NPD6319 Approved
0.5739 Remote Similarity NPD8413 Clinical (unspecified phase)
0.573 Remote Similarity NPD7331 Phase 2
0.5728 Remote Similarity NPD4753 Phase 2
0.5728 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5727 Remote Similarity NPD5211 Phase 2
0.5726 Remote Similarity NPD7078 Approved
0.5714 Remote Similarity NPD4137 Phase 3
0.5714 Remote Similarity NPD4202 Approved
0.5702 Remote Similarity NPD6016 Approved
0.5702 Remote Similarity NPD6015 Approved
0.5701 Remote Similarity NPD7732 Phase 3
0.5701 Remote Similarity NPD4697 Phase 3
0.57 Remote Similarity NPD4197 Approved
0.5688 Remote Similarity NPD6648 Approved
0.5688 Remote Similarity NPD5285 Approved
0.5688 Remote Similarity NPD5286 Approved
0.5688 Remote Similarity NPD4696 Approved
0.568 Remote Similarity NPD7736 Approved
0.5678 Remote Similarity NPD6868 Approved
0.5676 Remote Similarity NPD6647 Phase 2
0.5669 Remote Similarity NPD7260 Phase 2
0.5656 Remote Similarity NPD6370 Approved
0.5656 Remote Similarity NPD5988 Approved
0.5652 Remote Similarity NPD2067 Discontinued
0.5652 Remote Similarity NPD4747 Approved
0.5652 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5648 Remote Similarity NPD5959 Approved
0.5644 Remote Similarity NPD5329 Approved
0.5641 Remote Similarity NPD6858 Approved
0.5641 Remote Similarity NPD4632 Approved
0.5641 Remote Similarity NPD7094 Approved
0.5638 Remote Similarity NPD4687 Approved
0.5636 Remote Similarity NPD5223 Approved
0.5636 Remote Similarity NPD5344 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