NPASS Compound

Structure

CID277042 OpenBabel06191716082D 21 23 0 0 0 0 0 0 0 0999 V2000 7.0132 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 1 5 1 0 0 0 0 2 3 1 0 0 0 0 2 6 2 3 0 0 0 3 7 2 3 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 15 2 0 0 0 0 10 18 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	285.14
Volume:	298.468
LogP:	3.454
LogD:	3.257
LogS:	-4.11
# Rotatable Bonds:	4
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	2.344
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.805
MDCK Permeability:	2.609090370242484e-05
Pgp-inhibitor:	0.953
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.924
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.381
Plasma Protein Binding (PPB):	96.79044342041016%
Volume Distribution (VD):	0.833
Pgp-substrate:	3.3464274406433105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.715
CYP2C19-inhibitor:	0.668
CYP2C19-substrate:	0.505
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.642
CYP2D6-inhibitor:	0.836
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	10.873
Half-life (T1/2):	0.655

ADMET: Toxicity

hERG Blockers:	0.639
Human Hepatotoxicity (H-HT):	0.451
Drug-inuced Liver Injury (DILI):	0.196
AMES Toxicity:	0.816
Rat Oral Acute Toxicity:	0.629
Maximum Recommended Daily Dose:	0.458
Skin Sensitization:	0.967
Carcinogencity:	0.804
Eye Corrosion:	0.008
Eye Irritation:	0.108
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC277042

Natural Product ID:	NPC277042
*Common Name:**	5-(1,3-Benzodioxol-5-Yl)-1-Piperidin-1-Ylpenta-2,4-Dien-1-One
IUPAC Name:	5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
Synonyms:
Standard InCHIKey:	MXXWOMGUGJBKIW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2
SMILES:	C1CCN(CC1)C(=O)C=CC=Cc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3188765
PubChem CID:	4840
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	Dominican Republic	n.a.	PMID[11430019]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695795]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	corms	Iquitos, Peru	2005-MAY	PMID[19341262]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341262]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19485332]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22909174]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23149469]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25988621]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO230	Palisota barteri	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11511	Cochlearia officinalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9166	Monascus rubropunctatus	Species	Fellodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO43	Leifsonia aquatica	Species	Microbacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO876	Didymosphaeria enalia	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6880	Crocus corsicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12488	Bupleurum rigidum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23642	Penicillium tardum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2393	Matsumurella chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13059	Abies webbiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6428	Euphorbia wangii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8639	Agaricus xanthodermus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11137	Dichotomanthes tristaniicarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2840	Podocarpus minor	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7536	Mycoplasma mycoides	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO964	Homalium laurifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9950	Coelogyne nitida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10459	Brickellia longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3968	Dracontium loretense	Species	Araceae	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

Activity Type	# Activity
Potency	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	15.0	nM	PMID[465967]

☑ 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 NPC277042 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1624
0.2-0.3	7883
0.3-0.4	10701
0.4-0.5	6192
0.5-0.6	12264
0.6-0.7	3390
0.7-0.8	353
0.8-0.85	8
0.85-0.9	9
0.9-0.95	15
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC230698
1.0	High Similarity	NPC73883
1.0	High Similarity	NPC196609
1.0	High Similarity	NPC136330
1.0	High Similarity	NPC255817
1.0	High Similarity	NPC205178
1.0	High Similarity	NPC251454
0.9922	High Similarity	NPC99078
0.9921	High Similarity	NPC167096
0.9845	High Similarity	NPC252107
0.9845	High Similarity	NPC220923
0.9845	High Similarity	NPC470707
0.9462	High Similarity	NPC103947
0.9462	High Similarity	NPC94280
0.9462	High Similarity	NPC45783
0.9462	High Similarity	NPC159150
0.9462	High Similarity	NPC193673
0.9462	High Similarity	NPC328419
0.9389	High Similarity	NPC96406
0.9389	High Similarity	NPC180647
0.9318	High Similarity	NPC145446
0.9318	High Similarity	NPC137172
0.9308	High Similarity	NPC217574
0.9248	High Similarity	NPC225745
0.9248	High Similarity	NPC248505
0.9248	High Similarity	NPC95366
0.9173	High Similarity	NPC469808
0.9015	High Similarity	NPC318862
0.8881	High Similarity	NPC471073
0.8881	High Similarity	NPC270811
0.8824	High Similarity	NPC194359
0.8824	High Similarity	NPC28641
0.8759	High Similarity	NPC231572
0.8714	High Similarity	NPC244338
0.8521	High Similarity	NPC469978
0.8503	High Similarity	NPC169742
0.8345	Intermediate Similarity	NPC416184
0.8311	Intermediate Similarity	NPC470708
0.8288	Intermediate Similarity	NPC470088
0.8286	Intermediate Similarity	NPC113236
0.8286	Intermediate Similarity	NPC214036
0.8235	Intermediate Similarity	NPC231198
0.8214	Intermediate Similarity	NPC7018
0.8168	Intermediate Similarity	NPC69670
0.8108	Intermediate Similarity	NPC223125
0.8077	Intermediate Similarity	NPC111225
0.806	Intermediate Similarity	NPC256167
0.8043	Intermediate Similarity	NPC470706
0.8015	Intermediate Similarity	NPC199209
0.8015	Intermediate Similarity	NPC212643
0.8	Intermediate Similarity	NPC223124
0.7985	Intermediate Similarity	NPC114845
0.7974	Intermediate Similarity	NPC106786
0.7973	Intermediate Similarity	NPC475959
0.7956	Intermediate Similarity	NPC251466
0.7956	Intermediate Similarity	NPC218323
0.7935	Intermediate Similarity	NPC59567
0.7929	Intermediate Similarity	NPC118419
0.7899	Intermediate Similarity	NPC172403
0.7895	Intermediate Similarity	NPC57501
0.7883	Intermediate Similarity	NPC170583
0.7883	Intermediate Similarity	NPC71105
0.7883	Intermediate Similarity	NPC152186
0.7883	Intermediate Similarity	NPC182147
0.7883	Intermediate Similarity	NPC207541
0.7883	Intermediate Similarity	NPC246133
0.7848	Intermediate Similarity	NPC241055
0.7842	Intermediate Similarity	NPC469977
0.7826	Intermediate Similarity	NPC156944
0.7817	Intermediate Similarity	NPC473463
0.7812	Intermediate Similarity	NPC127326
0.781	Intermediate Similarity	NPC300955
0.7786	Intermediate Similarity	NPC160193
0.777	Intermediate Similarity	NPC157740
0.777	Intermediate Similarity	NPC191302
0.777	Intermediate Similarity	NPC64948
0.777	Intermediate Similarity	NPC41331
0.777	Intermediate Similarity	NPC291449
0.777	Intermediate Similarity	NPC99798
0.7763	Intermediate Similarity	NPC148898
0.7762	Intermediate Similarity	NPC11147
0.7752	Intermediate Similarity	NPC31279
0.7721	Intermediate Similarity	NPC193484
0.7714	Intermediate Similarity	NPC147247
0.7714	Intermediate Similarity	NPC246974
0.7697	Intermediate Similarity	NPC119669
0.7692	Intermediate Similarity	NPC284855
0.7692	Intermediate Similarity	NPC282477
0.7662	Intermediate Similarity	NPC41178
0.7662	Intermediate Similarity	NPC76079
0.7662	Intermediate Similarity	NPC138487
0.7662	Intermediate Similarity	NPC78733
0.7662	Intermediate Similarity	NPC93593
0.7662	Intermediate Similarity	NPC216459
0.7658	Intermediate Similarity	NPC306669
0.7658	Intermediate Similarity	NPC168409
0.7655	Intermediate Similarity	NPC193528
0.7651	Intermediate Similarity	NPC145304
0.7647	Intermediate Similarity	NPC233029
0.7647	Intermediate Similarity	NPC210148
0.7626	Intermediate Similarity	NPC85830
0.7622	Intermediate Similarity	NPC266425
0.7616	Intermediate Similarity	NPC37144
0.7616	Intermediate Similarity	NPC59907
0.7613	Intermediate Similarity	NPC31311
0.7613	Intermediate Similarity	NPC234392
0.7613	Intermediate Similarity	NPC146288
0.7605	Intermediate Similarity	NPC471650
0.759	Intermediate Similarity	NPC116007
0.7582	Intermediate Similarity	NPC476579
0.7582	Intermediate Similarity	NPC474852
0.7574	Intermediate Similarity	NPC344161
0.7556	Intermediate Similarity	NPC277460
0.7551	Intermediate Similarity	NPC314682
0.7537	Intermediate Similarity	NPC268317
0.7536	Intermediate Similarity	NPC298486
0.7534	Intermediate Similarity	NPC254610
0.7517	Intermediate Similarity	NPC475828
0.7516	Intermediate Similarity	NPC329640
0.75	Intermediate Similarity	NPC213206
0.75	Intermediate Similarity	NPC477259
0.75	Intermediate Similarity	NPC169387
0.75	Intermediate Similarity	NPC328750
0.75	Intermediate Similarity	NPC474915
0.75	Intermediate Similarity	NPC188163
0.7485	Intermediate Similarity	NPC83511
0.7485	Intermediate Similarity	NPC4669
0.7483	Intermediate Similarity	NPC477694
0.7483	Intermediate Similarity	NPC477705
0.7481	Intermediate Similarity	NPC280001
0.7481	Intermediate Similarity	NPC185738
0.7481	Intermediate Similarity	NPC179309
0.7468	Intermediate Similarity	NPC215829
0.7468	Intermediate Similarity	NPC306902
0.7468	Intermediate Similarity	NPC85747
0.7468	Intermediate Similarity	NPC97072
0.7468	Intermediate Similarity	NPC8337
0.7468	Intermediate Similarity	NPC160298
0.7468	Intermediate Similarity	NPC266753
0.7468	Intermediate Similarity	NPC477559
0.7468	Intermediate Similarity	NPC232924
0.7464	Intermediate Similarity	NPC80241
0.7464	Intermediate Similarity	NPC301641
0.7451	Intermediate Similarity	NPC211296
0.7434	Intermediate Similarity	NPC95075
0.7434	Intermediate Similarity	NPC253883
0.7434	Intermediate Similarity	NPC90844
0.7431	Intermediate Similarity	NPC477706
0.7425	Intermediate Similarity	NPC102760
0.7423	Intermediate Similarity	NPC303581
0.7423	Intermediate Similarity	NPC67978
0.7419	Intermediate Similarity	NPC476580
0.7417	Intermediate Similarity	NPC130926
0.7407	Intermediate Similarity	NPC86469
0.7405	Intermediate Similarity	NPC118804
0.7405	Intermediate Similarity	NPC477080
0.7405	Intermediate Similarity	NPC111485
0.7394	Intermediate Similarity	NPC286683
0.7391	Intermediate Similarity	NPC471877
0.7388	Intermediate Similarity	NPC294941
0.7379	Intermediate Similarity	NPC160692
0.7376	Intermediate Similarity	NPC120066
0.7358	Intermediate Similarity	NPC135006
0.7358	Intermediate Similarity	NPC26353
0.7357	Intermediate Similarity	NPC249788
0.7353	Intermediate Similarity	NPC120075
0.7353	Intermediate Similarity	NPC33271
0.7347	Intermediate Similarity	NPC42793
0.7347	Intermediate Similarity	NPC301050
0.7347	Intermediate Similarity	NPC307682
0.7347	Intermediate Similarity	NPC231884
0.7347	Intermediate Similarity	NPC167944
0.7347	Intermediate Similarity	NPC131204
0.7346	Intermediate Similarity	NPC474324
0.7346	Intermediate Similarity	NPC57812
0.7338	Intermediate Similarity	NPC469540
0.7338	Intermediate Similarity	NPC219162
0.7338	Intermediate Similarity	NPC469539
0.7333	Intermediate Similarity	NPC181905
0.7333	Intermediate Similarity	NPC308267
0.7333	Intermediate Similarity	NPC138438
0.7333	Intermediate Similarity	NPC908
0.7329	Intermediate Similarity	NPC232514
0.7329	Intermediate Similarity	NPC276944
0.7329	Intermediate Similarity	NPC238530
0.7329	Intermediate Similarity	NPC35345
0.7329	Intermediate Similarity	NPC225774
0.7324	Intermediate Similarity	NPC301713
0.7315	Intermediate Similarity	NPC226005
0.7305	Intermediate Similarity	NPC27887
0.7303	Intermediate Similarity	NPC185838
0.7301	Intermediate Similarity	NPC475845
0.7297	Intermediate Similarity	NPC253429
0.7297	Intermediate Similarity	NPC230968
0.7297	Intermediate Similarity	NPC102260
0.7292	Intermediate Similarity	NPC200555
0.7292	Intermediate Similarity	NPC476748
0.7292	Intermediate Similarity	NPC196026
0.7285	Intermediate Similarity	NPC136860
0.7285	Intermediate Similarity	NPC128019

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 NPC277042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	708
0.2-0.3	1153
0.3-0.4	2231
0.4-0.5	2710
0.5-0.6	1548
0.6-0.7	553
0.7-0.8	72
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD2492	Phase 1
0.8462	Intermediate Similarity	NPD5297	Approved
0.8014	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5718	Phase 2
0.7823	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3885	Approved
0.7582	Intermediate Similarity	NPD824	Approved
0.7535	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7110	Phase 1
0.7481	Intermediate Similarity	NPD5536	Phase 2
0.7468	Intermediate Similarity	NPD5604	Discontinued
0.7452	Intermediate Similarity	NPD5977	Approved
0.7452	Intermediate Similarity	NPD5978	Approved
0.7451	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4210	Discontinued
0.7372	Intermediate Similarity	NPD1357	Approved
0.7347	Intermediate Similarity	NPD6895	Approved
0.7347	Intermediate Similarity	NPD6896	Approved
0.7347	Intermediate Similarity	NPD743	Approved
0.7333	Intermediate Similarity	NPD4237	Approved
0.7333	Intermediate Similarity	NPD4236	Phase 3
0.7325	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4166	Phase 2
0.7279	Intermediate Similarity	NPD2653	Approved
0.7262	Intermediate Similarity	NPD7280	Phase 3
0.7262	Intermediate Similarity	NPD7281	Phase 3
0.7261	Intermediate Similarity	NPD6873	Phase 2
0.7261	Intermediate Similarity	NPD6385	Approved
0.7261	Intermediate Similarity	NPD6386	Approved
0.726	Intermediate Similarity	NPD3142	Approved
0.726	Intermediate Similarity	NPD3140	Approved
0.7234	Intermediate Similarity	NPD1420	Approved
0.7234	Intermediate Similarity	NPD1421	Approved
0.7226	Intermediate Similarity	NPD3640	Phase 3
0.7226	Intermediate Similarity	NPD3641	Approved
0.7226	Intermediate Similarity	NPD3639	Approved
0.7214	Intermediate Similarity	NPD3705	Approved
0.7208	Intermediate Similarity	NPD3146	Approved
0.7208	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4584	Approved
0.72	Intermediate Similarity	NPD3656	Approved
0.7197	Intermediate Similarity	NPD6875	Approved
0.7197	Intermediate Similarity	NPD6876	Approved
0.7175	Intermediate Similarity	NPD5457	Discontinued
0.717	Intermediate Similarity	NPD2978	Approved
0.717	Intermediate Similarity	NPD2977	Approved
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7124	Intermediate Similarity	NPD2219	Phase 1
0.7123	Intermediate Similarity	NPD3144	Approved
0.7123	Intermediate Similarity	NPD3145	Approved
0.7122	Intermediate Similarity	NPD6382	Discontinued
0.7114	Intermediate Similarity	NPD6111	Discontinued
0.7113	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5177	Phase 3
0.7097	Intermediate Similarity	NPD1424	Approved
0.7091	Intermediate Similarity	NPD2898	Approved
0.7075	Intermediate Similarity	NPD3531	Approved
0.7075	Intermediate Similarity	NPD3532	Approved
0.7075	Intermediate Similarity	NPD3530	Approved
0.7075	Intermediate Similarity	NPD2674	Phase 3
0.7075	Intermediate Similarity	NPD2245	Discovery
0.7071	Intermediate Similarity	NPD2668	Approved
0.7071	Intermediate Similarity	NPD2667	Approved
0.7063	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5481	Discontinued
0.7059	Intermediate Similarity	NPD5283	Phase 1
0.7047	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4017	Approved
0.7021	Intermediate Similarity	NPD3447	Discontinued
0.702	Intermediate Similarity	NPD1725	Approved
0.7019	Intermediate Similarity	NPD5353	Approved
0.7018	Intermediate Similarity	NPD6618	Phase 2
0.7013	Intermediate Similarity	NPD5241	Discontinued
0.7006	Intermediate Similarity	NPD6030	Approved
0.7006	Intermediate Similarity	NPD1670	Discontinued
0.7006	Intermediate Similarity	NPD6031	Approved
0.7006	Intermediate Similarity	NPD2122	Discontinued
0.6994	Remote Similarity	NPD3349	Phase 2
0.6993	Remote Similarity	NPD4162	Approved
0.6993	Remote Similarity	NPD3060	Approved
0.6992	Remote Similarity	NPD1358	Approved
0.6989	Remote Similarity	NPD6493	Phase 3
0.6982	Remote Similarity	NPD6297	Approved
0.6978	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1375	Discontinued
0.6968	Remote Similarity	NPD5295	Discontinued
0.6968	Remote Similarity	NPD7124	Phase 2
0.6964	Remote Similarity	NPD5312	Approved
0.6964	Remote Similarity	NPD5313	Approved
0.6962	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5677	Discontinued
0.6944	Remote Similarity	NPD2922	Phase 1
0.6928	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2233	Approved
0.6923	Remote Similarity	NPD2232	Approved
0.6923	Remote Similarity	NPD2230	Approved
0.6918	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3134	Approved
0.6913	Remote Similarity	NPD3110	Approved
0.6913	Remote Similarity	NPD3109	Approved
0.6903	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4727	Phase 1
0.6897	Remote Similarity	NPD7291	Discontinued
0.6894	Remote Similarity	NPD3384	Approved
0.6894	Remote Similarity	NPD3383	Approved
0.6894	Remote Similarity	NPD3382	Approved
0.6892	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7119	Phase 2
0.6886	Remote Similarity	NPD4481	Phase 3
0.6879	Remote Similarity	NPD2595	Approved
0.6879	Remote Similarity	NPD4739	Approved
0.6879	Remote Similarity	NPD2594	Approved
0.6859	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2120	Phase 2
0.6854	Remote Similarity	NPD5582	Discontinued
0.6852	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5772	Approved
0.6852	Remote Similarity	NPD5773	Approved
0.6852	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7905	Discontinued
0.6835	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4773	Phase 2
0.6832	Remote Similarity	NPD4772	Phase 2
0.6824	Remote Similarity	NPD5746	Approved
0.6821	Remote Similarity	NPD6853	Approved
0.6821	Remote Similarity	NPD6851	Approved
0.6818	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2560	Approved
0.681	Remote Similarity	NPD2563	Approved
0.6807	Remote Similarity	NPD6107	Approved
0.6802	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2161	Phase 2
0.6792	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5976	Discontinued
0.679	Remote Similarity	NPD7298	Approved
0.6788	Remote Similarity	NPD228	Approved
0.6786	Remote Similarity	NPD3596	Phase 2
0.6781	Remote Similarity	NPD4098	Discontinued
0.6779	Remote Similarity	NPD1336	Approved
0.6778	Remote Similarity	NPD4420	Approved
0.6772	Remote Similarity	NPD2335	Discontinued
0.6772	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4123	Phase 3
0.677	Remote Similarity	NPD2592	Discontinued
0.6768	Remote Similarity	NPD6788	Approved
0.6768	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6071	Discontinued
0.675	Remote Similarity	NPD3687	Approved
0.675	Remote Similarity	NPD3686	Approved
0.6748	Remote Similarity	NPD4585	Approved
0.6747	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7018	Phase 2
0.6733	Remote Similarity	NPD5745	Approved
0.6732	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4108	Discontinued
0.6731	Remote Similarity	NPD5754	Discontinued
0.6731	Remote Similarity	NPD6331	Phase 2
0.673	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1309	Phase 2
0.6727	Remote Similarity	NPD1307	Phase 2
0.6726	Remote Similarity	NPD5242	Approved
0.6726	Remote Similarity	NPD2388	Discontinued
0.6711	Remote Similarity	NPD5163	Phase 2
0.671	Remote Similarity	NPD7153	Discontinued
0.6708	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5967	Approved
0.6706	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7549	Discontinued
0.669	Remote Similarity	NPD2486	Discontinued
0.6688	Remote Similarity	NPD3156	Discontinued
0.6667	Remote Similarity	NPD3051	Approved
0.6667	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1039	Discontinued
0.6667	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3294	Phase 2
0.6648	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2904	Discontinued
0.6647	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1669	Approved
0.663	Remote Similarity	NPD5006	Approved
0.663	Remote Similarity	NPD5564	Approved
0.663	Remote Similarity	NPD5005	Approved
0.6629	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7832	Clinical (unspecified phase)

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