NPASS Compound

Structure

CID199738 OpenBabel06191715592D 38 41 0 0 1 0 0 0 0 0999 V2000 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 6 1 0 0 0 0 2 7 2 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 18 26 1 0 0 0 0 19 27 2 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 23 38 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 28 33 1 0 0 0 0 29 32 1 0 0 0 0 29 34 1 0 0 0 0 30 33 2 3 0 0 0 30 35 1 0 0 0 0 31 34 2 3 0 0 0 31 36 1 0 0 0 0 32 37 2 0 0 0 0 32 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.22
Volume:	545.41
LogP:	4.385
LogD:	4.315
LogS:	-4.458
# Rotatable Bonds:	14
TPSA:	84.5
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	2.756
Fsp3:	0.156
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	0.0001612491178093478
Pgp-inhibitor:	0.947
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.546
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.402

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	99.64952850341797%
Volume Distribution (VD):	0.643
Pgp-substrate:	1.056088924407959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.308
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.858
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.963
CYP2C9-substrate:	0.449
CYP2D6-inhibitor:	0.16
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	2.468
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.868
Human Hepatotoxicity (H-HT):	0.541
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.208
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.155
Skin Sensitization:	0.417
Carcinogencity:	0.526
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC199738

Natural Product ID:	NPC199738
*Common Name:**	(2-Benzamido-3-Phenylpropyl) 2-Benzamido-3-Phenylpropanoate
IUPAC Name:	(2-benzamido-3-phenylpropyl) 2-benzamido-3-phenylpropanoate
Synonyms:
Standard InCHIKey:	CVULDJMCSSACEO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H30N2O4/c35-30(26-17-9-3-10-18-26)33-28(21-24-13-5-1-6-14-24)23-38-32(37)29(22-25-15-7-2-8-16-25)34-31(36)27-19-11-4-12-20-27/h1-20,28-29H,21-23H2,(H,33,35)(H,34,36)
SMILES:	c1ccc(cc1)CC(COC(=O)C(Cc1ccccc1)N=C(c1ccccc1)O)N=C(c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1979730
PubChem CID:	328238
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004321] Phenylalanine 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
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	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
GI50	43

Activity Type	# Activity
Cell Line	43

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	34994.52	nM	PMID[520796]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	25585.86	nM	PMID[520796]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	32658.78	nM	PMID[520796]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520796]

☑ 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 NPC199738 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	135
0.1-0.2	780
0.2-0.3	3266
0.3-0.4	12261
0.4-0.5	15729
0.5-0.6	9264
0.6-0.7	1129
0.7-0.8	124
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC210950
0.9504	High Similarity	NPC4974
0.8333	Intermediate Similarity	NPC190663
0.8203	Intermediate Similarity	NPC160493
0.8134	Intermediate Similarity	NPC244866
0.8	Intermediate Similarity	NPC211551
0.7953	Intermediate Similarity	NPC169328
0.7926	Intermediate Similarity	NPC246913
0.7907	Intermediate Similarity	NPC80150
0.7891	Intermediate Similarity	NPC310467
0.7823	Intermediate Similarity	NPC319579
0.7794	Intermediate Similarity	NPC45191
0.7778	Intermediate Similarity	NPC325651
0.7744	Intermediate Similarity	NPC47667
0.7704	Intermediate Similarity	NPC296712
0.7651	Intermediate Similarity	NPC56635
0.7634	Intermediate Similarity	NPC477061
0.7634	Intermediate Similarity	NPC45777
0.7615	Intermediate Similarity	NPC237420
0.7519	Intermediate Similarity	NPC197470
0.75	Intermediate Similarity	NPC476183
0.7479	Intermediate Similarity	NPC3371
0.7463	Intermediate Similarity	NPC35996
0.7447	Intermediate Similarity	NPC6570
0.7444	Intermediate Similarity	NPC476184
0.7444	Intermediate Similarity	NPC476281
0.7438	Intermediate Similarity	NPC12730
0.7424	Intermediate Similarity	NPC319950
0.7422	Intermediate Similarity	NPC474584
0.7417	Intermediate Similarity	NPC33168
0.741	Intermediate Similarity	NPC326966
0.7407	Intermediate Similarity	NPC476241
0.7407	Intermediate Similarity	NPC476260
0.7398	Intermediate Similarity	NPC164859
0.7388	Intermediate Similarity	NPC474862
0.7388	Intermediate Similarity	NPC142577
0.7388	Intermediate Similarity	NPC27581
0.7379	Intermediate Similarity	NPC473922
0.7379	Intermediate Similarity	NPC106183
0.7372	Intermediate Similarity	NPC476353
0.7361	Intermediate Similarity	NPC91953
0.7357	Intermediate Similarity	NPC470392
0.7353	Intermediate Similarity	NPC476125
0.7353	Intermediate Similarity	NPC476179
0.7344	Intermediate Similarity	NPC329011
0.7333	Intermediate Similarity	NPC476278
0.7324	Intermediate Similarity	NPC6913
0.7317	Intermediate Similarity	NPC318154
0.7299	Intermediate Similarity	NPC136453
0.7297	Intermediate Similarity	NPC132771
0.7292	Intermediate Similarity	NPC197921
0.7287	Intermediate Similarity	NPC273814
0.7266	Intermediate Similarity	NPC478147
0.7246	Intermediate Similarity	NPC71933
0.7246	Intermediate Similarity	NPC152850
0.7246	Intermediate Similarity	NPC105114
0.7246	Intermediate Similarity	NPC89923
0.7246	Intermediate Similarity	NPC239990
0.7241	Intermediate Similarity	NPC469360
0.7239	Intermediate Similarity	NPC478016
0.7239	Intermediate Similarity	NPC478014
0.7239	Intermediate Similarity	NPC478015
0.7234	Intermediate Similarity	NPC313663
0.7222	Intermediate Similarity	NPC327481
0.7219	Intermediate Similarity	NPC275839
0.7203	Intermediate Similarity	NPC127741
0.7188	Intermediate Similarity	NPC159767
0.7188	Intermediate Similarity	NPC155506
0.7153	Intermediate Similarity	NPC473938
0.7143	Intermediate Similarity	NPC311737
0.7143	Intermediate Similarity	NPC38458
0.7131	Intermediate Similarity	NPC311242
0.7123	Intermediate Similarity	NPC161069
0.7107	Intermediate Similarity	NPC476749
0.7103	Intermediate Similarity	NPC153007
0.7099	Intermediate Similarity	NPC1986
0.7099	Intermediate Similarity	NPC474544
0.7092	Intermediate Similarity	NPC157311
0.709	Intermediate Similarity	NPC314992
0.7083	Intermediate Similarity	NPC265521
0.7078	Intermediate Similarity	NPC93343
0.7071	Intermediate Similarity	NPC111428
0.7071	Intermediate Similarity	NPC473322
0.7068	Intermediate Similarity	NPC82963
0.7067	Intermediate Similarity	NPC254798
0.7063	Intermediate Similarity	NPC230611
0.705	Intermediate Similarity	NPC65310
0.705	Intermediate Similarity	NPC477937
0.7042	Intermediate Similarity	NPC44805
0.7042	Intermediate Similarity	NPC8761
0.7034	Intermediate Similarity	NPC77992
0.7027	Intermediate Similarity	NPC209509
0.6993	Remote Similarity	NPC328070
0.6992	Remote Similarity	NPC293628
0.6992	Remote Similarity	NPC122493
0.6992	Remote Similarity	NPC10781
0.6988	Remote Similarity	NPC294951
0.698	Remote Similarity	NPC81026
0.6975	Remote Similarity	NPC473402
0.6975	Remote Similarity	NPC279871
0.6974	Remote Similarity	NPC233702
0.6974	Remote Similarity	NPC470274
0.6972	Remote Similarity	NPC255447
0.6968	Remote Similarity	NPC212699
0.6968	Remote Similarity	NPC207675
0.6963	Remote Similarity	NPC470546
0.6959	Remote Similarity	NPC315283
0.6959	Remote Similarity	NPC314388
0.6953	Remote Similarity	NPC274089
0.6953	Remote Similarity	NPC191215
0.695	Remote Similarity	NPC469666
0.694	Remote Similarity	NPC2265
0.694	Remote Similarity	NPC281686
0.694	Remote Similarity	NPC106551
0.694	Remote Similarity	NPC188867
0.6934	Remote Similarity	NPC273830
0.6933	Remote Similarity	NPC475578
0.6933	Remote Similarity	NPC138775
0.6923	Remote Similarity	NPC246079
0.6923	Remote Similarity	NPC275538
0.6918	Remote Similarity	NPC473055
0.6918	Remote Similarity	NPC473052
0.6917	Remote Similarity	NPC258627
0.6917	Remote Similarity	NPC172128
0.6914	Remote Similarity	NPC306804
0.6914	Remote Similarity	NPC137627
0.6913	Remote Similarity	NPC266741
0.6913	Remote Similarity	NPC313867
0.6913	Remote Similarity	NPC316008
0.6906	Remote Similarity	NPC285394
0.6889	Remote Similarity	NPC470545
0.6889	Remote Similarity	NPC469574
0.6887	Remote Similarity	NPC105717
0.6884	Remote Similarity	NPC109151
0.6875	Remote Similarity	NPC107938
0.6875	Remote Similarity	NPC294516
0.6871	Remote Similarity	NPC322526
0.6871	Remote Similarity	NPC158277
0.6871	Remote Similarity	NPC471201
0.6867	Remote Similarity	NPC314358
0.6855	Remote Similarity	NPC223207
0.6855	Remote Similarity	NPC475439
0.6855	Remote Similarity	NPC473501
0.6855	Remote Similarity	NPC324569
0.6852	Remote Similarity	NPC89831
0.6848	Remote Similarity	NPC45037
0.6848	Remote Similarity	NPC269750
0.6848	Remote Similarity	NPC194671
0.6846	Remote Similarity	NPC153690
0.6838	Remote Similarity	NPC220698
0.6833	Remote Similarity	NPC9822
0.6831	Remote Similarity	NPC311753
0.6828	Remote Similarity	NPC132847
0.6824	Remote Similarity	NPC263493
0.6824	Remote Similarity	NPC269398
0.6821	Remote Similarity	NPC135121
0.6821	Remote Similarity	NPC328824
0.6821	Remote Similarity	NPC16188
0.6818	Remote Similarity	NPC227553
0.6818	Remote Similarity	NPC163674
0.6815	Remote Similarity	NPC470544
0.6813	Remote Similarity	NPC471771
0.6813	Remote Similarity	NPC290755
0.6813	Remote Similarity	NPC304074
0.6806	Remote Similarity	NPC257390
0.68	Remote Similarity	NPC477217
0.68	Remote Similarity	NPC201244
0.68	Remote Similarity	NPC322598
0.6794	Remote Similarity	NPC292758
0.6794	Remote Similarity	NPC65855
0.6792	Remote Similarity	NPC471053
0.6792	Remote Similarity	NPC471052
0.6792	Remote Similarity	NPC471051
0.6792	Remote Similarity	NPC476750
0.6791	Remote Similarity	NPC33742
0.679	Remote Similarity	NPC40234
0.6788	Remote Similarity	NPC239697
0.6788	Remote Similarity	NPC43275
0.6784	Remote Similarity	NPC163961
0.6784	Remote Similarity	NPC473305
0.6779	Remote Similarity	NPC139326
0.6774	Remote Similarity	NPC39431
0.6774	Remote Similarity	NPC25565
0.677	Remote Similarity	NPC328649
0.6768	Remote Similarity	NPC473354
0.6768	Remote Similarity	NPC476227
0.6768	Remote Similarity	NPC26108
0.6757	Remote Similarity	NPC239762
0.6757	Remote Similarity	NPC163392
0.6755	Remote Similarity	NPC262077
0.675	Remote Similarity	NPC325441
0.6744	Remote Similarity	NPC67043
0.6741	Remote Similarity	NPC317254
0.6738	Remote Similarity	NPC474847
0.6735	Remote Similarity	NPC471264
0.6735	Remote Similarity	NPC471265
0.6733	Remote Similarity	NPC476978
0.6732	Remote Similarity	NPC476757
0.6732	Remote Similarity	NPC245974
0.6726	Remote Similarity	NPC471526

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 NPC199738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	103
0.1-0.2	432
0.2-0.3	813
0.3-0.4	1695
0.4-0.5	3152
0.5-0.6	2330
0.6-0.7	554
0.7-0.8	70
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.814	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6624	Discontinued
0.7557	Intermediate Similarity	NPD5981	Approved
0.7552	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD3644	Approved
0.754	Intermediate Similarity	NPD3643	Approved
0.754	Intermediate Similarity	NPD3642	Approved
0.7519	Intermediate Similarity	NPD1348	Approved
0.7518	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3123	Discovery
0.7434	Intermediate Similarity	NPD4335	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD8011	Discontinued
0.7405	Intermediate Similarity	NPD1758	Phase 1
0.7368	Intermediate Similarity	NPD8019	Approved
0.7348	Intermediate Similarity	NPD1759	Phase 1
0.7343	Intermediate Similarity	NPD6864	Phase 2
0.7343	Intermediate Similarity	NPD6865	Phase 2
0.7338	Intermediate Similarity	NPD3136	Phase 2
0.7338	Intermediate Similarity	NPD4738	Phase 2
0.7313	Intermediate Similarity	NPD4136	Approved
0.7313	Intermediate Similarity	NPD4106	Approved
0.7313	Intermediate Similarity	NPD4135	Approved
0.7299	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD9712	Approved
0.7292	Intermediate Similarity	NPD7450	Phase 2
0.7286	Intermediate Similarity	NPD4621	Approved
0.7286	Intermediate Similarity	NPD4619	Approved
0.728	Intermediate Similarity	NPD1040	Phase 2
0.7266	Intermediate Similarity	NPD5201	Approved
0.7266	Intermediate Similarity	NPD4617	Approved
0.7266	Intermediate Similarity	NPD4620	Approved
0.7266	Intermediate Similarity	NPD5203	Approved
0.7259	Intermediate Similarity	NPD4480	Approved
0.7234	Intermediate Similarity	NPD7714	Approved
0.7234	Intermediate Similarity	NPD7715	Approved
0.7226	Intermediate Similarity	NPD3125	Approved
0.7218	Intermediate Similarity	NPD4479	Discontinued
0.7213	Intermediate Similarity	NPD9710	Approved
0.7213	Intermediate Similarity	NPD9711	Approved
0.7206	Intermediate Similarity	NPD2584	Suspended
0.7183	Intermediate Similarity	NPD5120	Approved
0.7183	Intermediate Similarity	NPD5119	Approved
0.7183	Intermediate Similarity	NPD5121	Approved
0.7172	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4105	Approved
0.7164	Intermediate Similarity	NPD4102	Approved
0.7162	Intermediate Similarity	NPD7740	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD8323	Discontinued
0.7153	Intermediate Similarity	NPD6852	Discontinued
0.7152	Intermediate Similarity	NPD7131	Phase 3
0.7143	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4807	Approved
0.7132	Intermediate Similarity	NPD4806	Approved
0.7113	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3098	Discontinued
0.7095	Intermediate Similarity	NPD3400	Discontinued
0.709	Intermediate Similarity	NPD2218	Phase 2
0.709	Intermediate Similarity	NPD2217	Approved
0.7089	Intermediate Similarity	NPD6746	Phase 2
0.7071	Intermediate Similarity	NPD7828	Discontinued
0.7071	Intermediate Similarity	NPD5204	Approved
0.7068	Intermediate Similarity	NPD5292	Approved
0.7068	Intermediate Similarity	NPD5291	Approved
0.7063	Intermediate Similarity	NPD6309	Approved
0.7063	Intermediate Similarity	NPD6311	Approved
0.7063	Intermediate Similarity	NPD6310	Approved
0.7059	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2159	Approved
0.705	Intermediate Similarity	NPD2625	Approved
0.705	Intermediate Similarity	NPD2627	Approved
0.705	Intermediate Similarity	NPD2626	Approved
0.705	Intermediate Similarity	NPD2628	Approved
0.705	Intermediate Similarity	NPD2160	Approved
0.7019	Intermediate Similarity	NPD7997	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6502	Phase 2
0.7007	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5618	Discontinued
0.7	Intermediate Similarity	NPD7554	Discontinued
0.6992	Remote Similarity	NPD9566	Approved
0.6986	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5306	Approved
0.6985	Remote Similarity	NPD5305	Approved
0.6974	Remote Similarity	NPD6390	Discontinued
0.6966	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8265	Approved
0.694	Remote Similarity	NPD4574	Approved
0.694	Remote Similarity	NPD9568	Approved
0.694	Remote Similarity	NPD4576	Approved
0.6939	Remote Similarity	NPD4173	Approved
0.6939	Remote Similarity	NPD4172	Approved
0.6934	Remote Similarity	NPD3881	Discontinued
0.6923	Remote Similarity	NPD1330	Phase 2
0.6923	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6994	Approved
0.6912	Remote Similarity	NPD6993	Approved
0.6906	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5159	Phase 2
0.6906	Remote Similarity	NPD5157	Phase 1
0.6894	Remote Similarity	NPD2607	Approved
0.6892	Remote Similarity	NPD7978	Discontinued
0.6884	Remote Similarity	NPD7437	Approved
0.6884	Remote Similarity	NPD7436	Approved
0.6879	Remote Similarity	NPD7451	Discontinued
0.6875	Remote Similarity	NPD999	Phase 2
0.6861	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2199	Approved
0.6857	Remote Similarity	NPD2198	Approved
0.6835	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4006	Discontinued
0.6828	Remote Similarity	NPD3373	Approved
0.6815	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7495	Discontinued
0.6803	Remote Similarity	NPD6294	Approved
0.6803	Remote Similarity	NPD6295	Approved
0.6803	Remote Similarity	NPD8147	Approved
0.6803	Remote Similarity	NPD8148	Approved
0.68	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD555	Phase 2
0.6774	Remote Similarity	NPD8315	Phase 1
0.6763	Remote Similarity	NPD6287	Discontinued
0.6753	Remote Similarity	NPD7613	Discontinued
0.6746	Remote Similarity	NPD7798	Approved
0.6738	Remote Similarity	NPD5667	Approved
0.6733	Remote Similarity	NPD6681	Discovery
0.6716	Remote Similarity	NPD2652	Approved
0.6716	Remote Similarity	NPD2650	Approved
0.6714	Remote Similarity	NPD7250	Approved
0.6714	Remote Similarity	NPD7249	Approved
0.6713	Remote Similarity	NPD3661	Approved
0.6713	Remote Similarity	NPD3664	Approved
0.6713	Remote Similarity	NPD3662	Phase 3
0.6713	Remote Similarity	NPD3663	Approved
0.6712	Remote Similarity	NPD6623	Phase 3
0.6712	Remote Similarity	NPD6346	Approved
0.6711	Remote Similarity	NPD7939	Discontinued
0.6709	Remote Similarity	NPD7011	Discontinued
0.6707	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5705	Approved
0.6692	Remote Similarity	NPD5706	Approved
0.6692	Remote Similarity	NPD5704	Approved
0.6691	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6564	Approved
0.669	Remote Similarity	NPD6563	Approved
0.669	Remote Similarity	NPD6565	Approved
0.6687	Remote Similarity	NPD7608	Discontinued
0.6667	Remote Similarity	NPD5239	Approved
0.6667	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5235	Approved
0.6667	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5240	Approved
0.6667	Remote Similarity	NPD5236	Approved
0.6667	Remote Similarity	NPD5237	Approved
0.6646	Remote Similarity	NPD6913	Approved
0.6646	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2575	Approved
0.6645	Remote Similarity	NPD7253	Phase 3
0.6644	Remote Similarity	NPD7477	Discontinued
0.6644	Remote Similarity	NPD259	Phase 1
0.6643	Remote Similarity	NPD4217	Approved
0.6643	Remote Similarity	NPD4216	Approved
0.6643	Remote Similarity	NPD4218	Approved
0.6643	Remote Similarity	NPD2611	Approved
0.6643	Remote Similarity	NPD2612	Approved
0.6643	Remote Similarity	NPD2608	Approved
0.6643	Remote Similarity	NPD3131	Approved
0.6643	Remote Similarity	NPD2609	Approved
0.6643	Remote Similarity	NPD2610	Approved
0.6643	Remote Similarity	NPD4215	Approved
0.6643	Remote Similarity	NPD3132	Approved
0.6641	Remote Similarity	NPD855	Approved
0.6641	Remote Similarity	NPD854	Approved
0.6641	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3455	Phase 2
0.6623	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6039	Approved
0.662	Remote Similarity	NPD6325	Discontinued
0.662	Remote Similarity	NPD196	Phase 1
0.6618	Remote Similarity	NPD255	Approved
0.6618	Remote Similarity	NPD256	Approved
0.66	Remote Similarity	NPD1537	Approved
0.66	Remote Similarity	NPD1519	Approved
0.66	Remote Similarity	NPD1538	Phase 1
0.6599	Remote Similarity	NPD825	Approved
0.6599	Remote Similarity	NPD826	Approved
0.6597	Remote Similarity	NPD4175	Approved
0.6597	Remote Similarity	NPD4177	Approved
0.6577	Remote Similarity	NPD1536	Approved
0.6569	Remote Similarity	NPD5162	Approved
0.6567	Remote Similarity	NPD9508	Approved
0.6562	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7972	Discontinued
0.6556	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD8643	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