Structure

Physi-Chem Properties

Molecular Weight:  202.1
Volume:  220.69
LogP:  2.798
LogD:  2.672
LogS:  -3.222
# Rotatable Bonds:  2
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.544
Synthetic Accessibility Score:  2.715
Fsp3:  0.308
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.475
MDCK Permeability:  2.1329629817046225e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.932
Plasma Protein Binding (PPB):  80.58732604980469%
Volume Distribution (VD):  1.173
Pgp-substrate:  10.499247550964355%

ADMET: Metabolism

CYP1A2-inhibitor:  0.888
CYP1A2-substrate:  0.939
CYP2C19-inhibitor:  0.908
CYP2C19-substrate:  0.558
CYP2C9-inhibitor:  0.301
CYP2C9-substrate:  0.819
CYP2D6-inhibitor:  0.105
CYP2D6-substrate:  0.9
CYP3A4-inhibitor:  0.076
CYP3A4-substrate:  0.357

ADMET: Excretion

Clearance (CL):  7.827
Half-life (T1/2):  0.427

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.646
Drug-inuced Liver Injury (DILI):  0.632
AMES Toxicity:  0.379
Rat Oral Acute Toxicity:  0.056
Maximum Recommended Daily Dose:  0.497
Skin Sensitization:  0.057
Carcinogencity:  0.916
Eye Corrosion:  0.11
Eye Irritation:  0.9
Respiratory Toxicity:  0.894

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  Natural Product: NPC11799

Natural Product ID:  NPC11799
Common Name*:   1-(2-Prop-1-En-2-Yl-2,3-Dihydro-1-Benzofuran-5-Yl)Ethanone
IUPAC Name:   1-(2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)ethanone
Synonyms:  
Standard InCHIKey:  UVYUUQGGBNKRFU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H14O2/c1-8(2)13-7-11-6-10(9(3)14)4-5-12(11)15-13/h4-6,13H,1,7H2,2-3H3
SMILES:  C=C(C)C1Cc2cc(ccc2O1)C(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1985317
PubChem CID:   317196
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000119] Acetophenones

*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
NPO3791 Lentinus edodes Species Omphalotaceae Eukaryota n.a. n.a. n.a. PMID[15055237]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. n.a. n.a. PMID[18071251]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. faeces n.a. PMID[18323202]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[25559759]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[31244143]
NPO3791 Lentinus edodes Species Omphalotaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29132 Agaricus campestris Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11449 Eupatorium urticaefolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26618 Selaginella involvens Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26618 Selaginella involvens Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13862 Liatris sp. Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29132 Agaricus campestris Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11449 Eupatorium urticaefolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26035 Grindelia sp. Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18917 Ligularia sp. Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3791 Lentinus edodes Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2282 Ageratina altissima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29132 Agaricus campestris Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29132 Agaricus campestris Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26618 Selaginella involvens Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2282 Ageratina altissima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3791 Lentinus edodes Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14158 Selaginella tamariscina Species Selaginellaceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[476571]
NPT1175 Organism Spodoptera litura Spodoptera litura pED50 = 7.13 n.a. PMID[476572]
NPT35 Others n.a. Rf = 0.61 n.a. PMID[476572]
NPT1175 Organism Spodoptera litura Spodoptera litura ED50 = 7.4 10'-8mol/cm2 PMID[476572]

☑ 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 NPC11799 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 NPC141252
0.9831 High Similarity NPC470858
0.9508 High Similarity NPC170546
0.9508 High Similarity NPC939
0.9508 High Similarity NPC66246
0.9431 High Similarity NPC282230
0.9431 High Similarity NPC183348
0.9355 High Similarity NPC470976
0.9355 High Similarity NPC15083
0.9355 High Similarity NPC470977
0.9355 High Similarity NPC196979
0.928 High Similarity NPC470859
0.9113 High Similarity NPC50583
0.9048 High Similarity NPC279596
0.8984 High Similarity NPC247743
0.8952 High Similarity NPC237868
0.8879 High Similarity NPC23332
0.8814 High Similarity NPC252004
0.8793 High Similarity NPC183648
0.8722 High Similarity NPC137009
0.872 High Similarity NPC165556
0.8667 High Similarity NPC470860
0.8657 High Similarity NPC470856
0.8595 High Similarity NPC469954
0.8583 High Similarity NPC37512
0.8582 High Similarity NPC37206
0.8561 High Similarity NPC163029
0.8559 High Similarity NPC57879
0.855 High Similarity NPC209858
0.8548 High Similarity NPC314329
0.8527 High Similarity NPC109778
0.8525 High Similarity NPC206007
0.8516 High Similarity NPC125887
0.8504 High Similarity NPC474737
0.8496 Intermediate Similarity NPC29638
0.8473 Intermediate Similarity NPC229646
0.8456 Intermediate Similarity NPC171870
0.8456 Intermediate Similarity NPC27220
0.845 Intermediate Similarity NPC473019
0.8438 Intermediate Similarity NPC293387
0.8433 Intermediate Similarity NPC62735
0.8387 Intermediate Similarity NPC246214
0.8385 Intermediate Similarity NPC245395
0.8374 Intermediate Similarity NPC171023
0.8372 Intermediate Similarity NPC2401
0.8346 Intermediate Similarity NPC217914
0.8333 Intermediate Similarity NPC69403
0.8333 Intermediate Similarity NPC291189
0.832 Intermediate Similarity NPC225245
0.8309 Intermediate Similarity NPC11566
0.8306 Intermediate Similarity NPC35744
0.8306 Intermediate Similarity NPC473767
0.8306 Intermediate Similarity NPC201284
0.8296 Intermediate Similarity NPC259685
0.8296 Intermediate Similarity NPC233707
0.8286 Intermediate Similarity NPC14875
0.8281 Intermediate Similarity NPC224657
0.8281 Intermediate Similarity NPC2771
0.8279 Intermediate Similarity NPC220540
0.8276 Intermediate Similarity NPC38209
0.8273 Intermediate Similarity NPC470857
0.8271 Intermediate Similarity NPC292998
0.8271 Intermediate Similarity NPC324117
0.8268 Intermediate Similarity NPC474691
0.8264 Intermediate Similarity NPC90903
0.8264 Intermediate Similarity NPC53953
0.8264 Intermediate Similarity NPC279916
0.8258 Intermediate Similarity NPC183103
0.8248 Intermediate Similarity NPC472409
0.8248 Intermediate Similarity NPC184053
0.8244 Intermediate Similarity NPC327457
0.8244 Intermediate Similarity NPC86774
0.8235 Intermediate Similarity NPC36414
0.8231 Intermediate Similarity NPC59502
0.8227 Intermediate Similarity NPC168085
0.8226 Intermediate Similarity NPC293424
0.8226 Intermediate Similarity NPC32298
0.8226 Intermediate Similarity NPC152159
0.8222 Intermediate Similarity NPC254741
0.8217 Intermediate Similarity NPC177925
0.8217 Intermediate Similarity NPC474264
0.8214 Intermediate Similarity NPC190572
0.8214 Intermediate Similarity NPC286038
0.8209 Intermediate Similarity NPC470844
0.8203 Intermediate Similarity NPC221798
0.8203 Intermediate Similarity NPC184219
0.8201 Intermediate Similarity NPC17262
0.8201 Intermediate Similarity NPC213900
0.8195 Intermediate Similarity NPC66158
0.819 Intermediate Similarity NPC298224
0.8188 Intermediate Similarity NPC254010
0.8182 Intermediate Similarity NPC164295
0.8182 Intermediate Similarity NPC473982
0.8182 Intermediate Similarity NPC239134
0.8182 Intermediate Similarity NPC477412
0.8182 Intermediate Similarity NPC301717
0.8175 Intermediate Similarity NPC262635
0.8169 Intermediate Similarity NPC104172
0.8169 Intermediate Similarity NPC88886
0.8169 Intermediate Similarity NPC317492
0.8162 Intermediate Similarity NPC253616
0.816 Intermediate Similarity NPC54243
0.816 Intermediate Similarity NPC137710
0.8156 Intermediate Similarity NPC471285
0.8156 Intermediate Similarity NPC66991
0.8156 Intermediate Similarity NPC198427
0.8154 Intermediate Similarity NPC121104
0.8154 Intermediate Similarity NPC49852
0.8154 Intermediate Similarity NPC286683
0.8154 Intermediate Similarity NPC475496
0.8148 Intermediate Similarity NPC151113
0.8148 Intermediate Similarity NPC99854
0.8148 Intermediate Similarity NPC60667
0.8148 Intermediate Similarity NPC278832
0.8148 Intermediate Similarity NPC64157
0.8148 Intermediate Similarity NPC46869
0.8145 Intermediate Similarity NPC45104
0.8145 Intermediate Similarity NPC217423
0.8143 Intermediate Similarity NPC297788
0.8143 Intermediate Similarity NPC208584
0.814 Intermediate Similarity NPC65041
0.814 Intermediate Similarity NPC473626
0.813 Intermediate Similarity NPC205523
0.8129 Intermediate Similarity NPC130206
0.8129 Intermediate Similarity NPC313036
0.8129 Intermediate Similarity NPC51146
0.8129 Intermediate Similarity NPC166858
0.8129 Intermediate Similarity NPC147145
0.812 Intermediate Similarity NPC284424
0.8116 Intermediate Similarity NPC28337
0.8115 Intermediate Similarity NPC242136
0.8112 Intermediate Similarity NPC472421
0.8102 Intermediate Similarity NPC473988
0.8099 Intermediate Similarity NPC54626
0.8099 Intermediate Similarity NPC266743
0.8095 Intermediate Similarity NPC230951
0.8092 Intermediate Similarity NPC473907
0.8092 Intermediate Similarity NPC473744
0.8088 Intermediate Similarity NPC472516
0.8088 Intermediate Similarity NPC268081
0.8088 Intermediate Similarity NPC156910
0.8088 Intermediate Similarity NPC161196
0.8085 Intermediate Similarity NPC51641
0.8085 Intermediate Similarity NPC300267
0.8083 Intermediate Similarity NPC259554
0.8077 Intermediate Similarity NPC188327
0.8077 Intermediate Similarity NPC141059
0.8077 Intermediate Similarity NPC234109
0.8077 Intermediate Similarity NPC475236
0.8074 Intermediate Similarity NPC125920
0.8074 Intermediate Similarity NPC125269
0.8074 Intermediate Similarity NPC164136
0.8071 Intermediate Similarity NPC59522
0.8071 Intermediate Similarity NPC39329
0.8071 Intermediate Similarity NPC175504
0.8071 Intermediate Similarity NPC225884
0.8071 Intermediate Similarity NPC143896
0.8071 Intermediate Similarity NPC310130
0.8071 Intermediate Similarity NPC68104
0.8071 Intermediate Similarity NPC257097
0.8071 Intermediate Similarity NPC75049
0.8071 Intermediate Similarity NPC150408
0.8071 Intermediate Similarity NPC91560
0.8071 Intermediate Similarity NPC149026
0.8071 Intermediate Similarity NPC169591
0.8071 Intermediate Similarity NPC221432
0.8071 Intermediate Similarity NPC164980
0.8065 Intermediate Similarity NPC59035
0.8065 Intermediate Similarity NPC79202
0.8065 Intermediate Similarity NPC316062
0.8062 Intermediate Similarity NPC255073
0.8062 Intermediate Similarity NPC473885
0.8062 Intermediate Similarity NPC89630
0.8062 Intermediate Similarity NPC471074
0.8062 Intermediate Similarity NPC107846
0.806 Intermediate Similarity NPC55147
0.806 Intermediate Similarity NPC182428
0.8058 Intermediate Similarity NPC4743
0.8058 Intermediate Similarity NPC213322
0.8058 Intermediate Similarity NPC324386
0.8058 Intermediate Similarity NPC3188
0.8058 Intermediate Similarity NPC22467
0.8058 Intermediate Similarity NPC312391
0.8056 Intermediate Similarity NPC472423
0.8056 Intermediate Similarity NPC474772
0.8056 Intermediate Similarity NPC474744
0.8056 Intermediate Similarity NPC472580
0.8047 Intermediate Similarity NPC67300
0.8045 Intermediate Similarity NPC324488
0.8043 Intermediate Similarity NPC136095
0.8043 Intermediate Similarity NPC23257
0.8043 Intermediate Similarity NPC472515
0.8043 Intermediate Similarity NPC139554
0.8043 Intermediate Similarity NPC473076
0.8042 Intermediate Similarity NPC296030
0.8042 Intermediate Similarity NPC39929
0.8042 Intermediate Similarity NPC88445
0.8031 Intermediate Similarity NPC295317
0.803 Intermediate Similarity NPC473894
0.8029 Intermediate Similarity NPC84585

  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 NPC11799 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
0.8729 High Similarity NPD1241 Discontinued
0.8548 High Similarity NPD1547 Clinical (unspecified phase)
0.8358 Intermediate Similarity NPD2796 Approved
0.8189 Intermediate Similarity NPD3972 Approved
0.8175 Intermediate Similarity NPD1243 Approved
0.8175 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8162 Intermediate Similarity NPD2344 Approved
0.8129 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8062 Intermediate Similarity NPD1876 Approved
0.8029 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.8028 Intermediate Similarity NPD920 Approved
0.8015 Intermediate Similarity NPD2799 Discontinued
0.8014 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7985 Intermediate Similarity NPD3140 Approved
0.7985 Intermediate Similarity NPD3142 Approved
0.7971 Intermediate Similarity NPD1549 Phase 2
0.7929 Intermediate Similarity NPD2309 Approved
0.7899 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7899 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7899 Intermediate Similarity NPD1471 Phase 3
0.7852 Intermediate Similarity NPD1240 Approved
0.7836 Intermediate Similarity NPD2313 Discontinued
0.782 Intermediate Similarity NPD6832 Phase 2
0.7803 Intermediate Similarity NPD1019 Discontinued
0.7795 Intermediate Similarity NPD9545 Approved
0.7769 Intermediate Similarity NPD9717 Approved
0.7762 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD1510 Phase 2
0.7737 Intermediate Similarity NPD1607 Approved
0.7734 Intermediate Similarity NPD5691 Approved
0.7734 Intermediate Similarity NPD1651 Approved
0.773 Intermediate Similarity NPD4628 Phase 3
0.7703 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD5494 Approved
0.7676 Intermediate Similarity NPD3887 Approved
0.7674 Intermediate Similarity NPD17 Approved
0.7669 Intermediate Similarity NPD2798 Approved
0.7635 Intermediate Similarity NPD6280 Approved
0.7635 Intermediate Similarity NPD6279 Approved
0.7626 Intermediate Similarity NPD3748 Approved
0.7616 Intermediate Similarity NPD919 Approved
0.7612 Intermediate Similarity NPD9494 Approved
0.7594 Intermediate Similarity NPD3267 Approved
0.7594 Intermediate Similarity NPD3266 Approved
0.7591 Intermediate Similarity NPD4307 Phase 2
0.7584 Intermediate Similarity NPD7819 Suspended
0.7584 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD2935 Discontinued
0.7569 Intermediate Similarity NPD6799 Approved
0.7568 Intermediate Similarity NPD7411 Suspended
0.7557 Intermediate Similarity NPD1281 Approved
0.755 Intermediate Similarity NPD7075 Discontinued
0.7541 Intermediate Similarity NPD3134 Approved
0.7536 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD6355 Discontinued
0.7535 Intermediate Similarity NPD2800 Approved
0.7533 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD2346 Discontinued
0.7518 Intermediate Similarity NPD2353 Approved
0.7517 Intermediate Similarity NPD6801 Discontinued
0.7517 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD1247 Approved
0.75 Intermediate Similarity NPD1608 Approved
0.75 Intermediate Similarity NPD4380 Phase 2
0.748 Intermediate Similarity NPD1358 Approved
0.7466 Intermediate Similarity NPD6273 Approved
0.7465 Intermediate Similarity NPD2424 Discontinued
0.7463 Intermediate Similarity NPD1203 Approved
0.7462 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD9697 Approved
0.7447 Intermediate Similarity NPD4477 Approved
0.7447 Intermediate Similarity NPD4476 Approved
0.7445 Intermediate Similarity NPD6798 Discontinued
0.7445 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD7458 Discontinued
0.7419 Intermediate Similarity NPD2684 Approved
0.7405 Intermediate Similarity NPD1778 Approved
0.7405 Intermediate Similarity NPD4626 Approved
0.74 Intermediate Similarity NPD1934 Approved
0.7389 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7388 Intermediate Similarity NPD1283 Approved
0.7385 Intermediate Similarity NPD1894 Discontinued
0.7383 Intermediate Similarity NPD6599 Discontinued
0.7381 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD4308 Phase 3
0.7368 Intermediate Similarity NPD3882 Suspended
0.7364 Intermediate Similarity NPD9493 Approved
0.7361 Intermediate Similarity NPD7003 Approved
0.7361 Intermediate Similarity NPD3750 Approved
0.7355 Intermediate Similarity NPD6808 Phase 2
0.7339 Intermediate Similarity NPD290 Approved
0.7333 Intermediate Similarity NPD2797 Approved
0.7319 Intermediate Similarity NPD3268 Approved
0.7319 Intermediate Similarity NPD411 Approved
0.731 Intermediate Similarity NPD2354 Approved
0.7303 Intermediate Similarity NPD2296 Approved
0.7297 Intermediate Similarity NPD5586 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD2654 Approved
0.7286 Intermediate Similarity NPD1933 Approved
0.7286 Intermediate Similarity NPD447 Suspended
0.7279 Intermediate Similarity NPD2534 Approved
0.7279 Intermediate Similarity NPD2533 Approved
0.7279 Intermediate Similarity NPD4662 Approved
0.7279 Intermediate Similarity NPD2532 Approved
0.7279 Intermediate Similarity NPD4661 Approved
0.7273 Intermediate Similarity NPD6004 Phase 3
0.7273 Intermediate Similarity NPD6002 Phase 3
0.7273 Intermediate Similarity NPD6005 Phase 3
0.7273 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD8032 Phase 2
0.723 Intermediate Similarity NPD5049 Phase 3
0.7222 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD3496 Discontinued
0.7214 Intermediate Similarity NPD2979 Phase 3
0.7211 Intermediate Similarity NPD1511 Approved
0.7208 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD1551 Phase 2
0.72 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD3226 Approved
0.7194 Intermediate Similarity NPD1296 Phase 2
0.719 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD5535 Approved
0.7188 Intermediate Similarity NPD7843 Approved
0.7183 Intermediate Similarity NPD743 Approved
0.7181 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD5536 Phase 2
0.7154 Intermediate Similarity NPD7157 Approved
0.7152 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7768 Phase 2
0.7143 Intermediate Similarity NPD4947 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD7033 Discontinued
0.7133 Intermediate Similarity NPD957 Approved
0.7114 Intermediate Similarity NPD1512 Approved
0.7111 Intermediate Similarity NPD1481 Phase 2
0.7105 Intermediate Similarity NPD5889 Approved
0.7105 Intermediate Similarity NPD5890 Approved
0.7101 Intermediate Similarity NPD454 Approved
0.7097 Intermediate Similarity NPD3749 Approved
0.7089 Intermediate Similarity NPD3926 Phase 2
0.7086 Intermediate Similarity NPD2651 Approved
0.7086 Intermediate Similarity NPD2649 Approved
0.7083 Intermediate Similarity NPD2438 Suspended
0.7078 Intermediate Similarity NPD3817 Phase 2
0.7075 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD3764 Approved
0.707 Intermediate Similarity NPD6959 Discontinued
0.7068 Intermediate Similarity NPD5585 Approved
0.7067 Intermediate Similarity NPD3873 Phase 3
0.7067 Intermediate Similarity NPD3869 Phase 3
0.7063 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD3818 Discontinued
0.7059 Intermediate Similarity NPD7577 Discontinued
0.7059 Intermediate Similarity NPD5327 Phase 3
0.7054 Intermediate Similarity NPD821 Approved
0.7049 Intermediate Similarity NPD1238 Approved
0.7047 Intermediate Similarity NPD5401 Approved
0.7044 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD4618 Approved
0.7042 Intermediate Similarity NPD4622 Approved
0.7037 Intermediate Similarity NPD3823 Discontinued
0.7037 Intermediate Similarity NPD422 Phase 1
0.7037 Intermediate Similarity NPD1611 Approved
0.7037 Intermediate Similarity NPD1535 Discovery
0.7032 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD3691 Phase 2
0.7029 Intermediate Similarity NPD3690 Phase 2
0.7021 Intermediate Similarity NPD4062 Phase 3
0.7021 Intermediate Similarity NPD6233 Phase 2
0.7019 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD5844 Phase 1
0.7016 Intermediate Similarity NPD9261 Approved
0.7013 Intermediate Similarity NPD2801 Approved
0.7007 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD594 Approved
0.7 Intermediate Similarity NPD592 Approved
0.7 Intermediate Similarity NPD2186 Approved
0.6994 Remote Similarity NPD6559 Discontinued
0.6993 Remote Similarity NPD6651 Approved
0.6993 Remote Similarity NPD958 Approved
0.6986 Remote Similarity NPD2897 Discontinued
0.698 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1729 Discontinued
0.6972 Remote Similarity NPD4060 Phase 1
0.6966 Remote Similarity NPD2531 Phase 2
0.6957 Remote Similarity NPD1164 Approved
0.6954 Remote Similarity NPD5403 Approved
0.6951 Remote Similarity NPD4419 Clinical (unspecified phase)
0.695 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6948 Remote Similarity NPD6844 Discontinued
0.6944 Remote Similarity NPD5689 Approved
0.6944 Remote Similarity NPD5688 Approved
0.6937 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6937 Remote Similarity NPD6166 Phase 2
0.6937 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6933 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6933 Remote Similarity NPD5953 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