NPASS Compound

Structure

CID4974 OpenBabel06191715322D 33 35 0 0 1 0 0 0 0 0999 V2000 -4.3301 4.5000 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 -3.4641 -3.0000 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 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 -4.3301 -1.5000 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 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -4.3301 3.5000 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 -3.4641 -1.0000 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 -5.1962 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 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 -3.4641 3.0000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 24 1 0 0 0 0 19 33 1 0 0 0 0 20 28 2 3 0 0 0 20 30 1 0 0 0 0 23 26 1 0 0 0 0 24 17 1 6 0 0 0 24 28 1 0 0 0 0 25 18 1 1 0 0 0 25 27 1 0 0 0 0 25 29 1 0 0 0 0 26 29 2 3 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.2
Volume:	475.396
LogP:	3.116
LogD:	3.112
LogS:	-3.957
# Rotatable Bonds:	13
TPSA:	84.5
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	2.736
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.289
MDCK Permeability:	0.00016952090663835406
Pgp-inhibitor:	0.945
Pgp-substrate:	0.331
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	95.15542602539062%
Volume Distribution (VD):	0.607
Pgp-substrate:	7.266918659210205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.308
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.791
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.902
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.285
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	2.457
Half-life (T1/2):	0.59

ADMET: Toxicity

hERG Blockers:	0.475
Human Hepatotoxicity (H-HT):	0.36
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.302
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.231
Skin Sensitization:	0.318
Carcinogencity:	0.341
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC4974

Natural Product ID:	NPC4974
*Common Name:**	(S)-((S)-2-Acetamido-3-Phenylpropyl)2-Benzamido-3-Phenylpropanoate
IUPAC Name:	[(2S)-2-acetamido-3-phenylpropyl] (2S)-2-benzamido-3-phenylpropanoate
Synonyms:
Standard InCHIKey:	UBQCFEASTTXIKB-DQEYMECFSA-N
Standard InCHI:	InChI=1S/C27H28N2O4/c1-20(30)28-24(17-21-11-5-2-6-12-21)19-33-27(32)25(18-22-13-7-3-8-14-22)29-26(31)23-15-9-4-10-16-23/h2-16,24-25H,17-19H2,1H3,(H,28,30)(H,29,31)/t24-,25-/m0/s1
SMILES:	CC(=N[C@@H](Cc1ccccc1)COC(=O)[C@@H](N=C(c1ccccc1)O)Cc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1957989
PubChem CID:	46222163
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
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19099464]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19697926]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2421673]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	aerial parts	Muli County, Sichuan Province, China	2011-AUG	PMID[24219809]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9599286]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1558	Ozothamnus obcordatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16021	Boletus bovinus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20543	Psydrax livida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17240	Crematogaster brevis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20115	Melampodium argophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19889	Cereus stellatus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21614	Urceolaria scruposa	Species	Trichodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19763	Meloidogyne incognita	Species	Meloidogynidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17508	Danae racemosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19768	Xylosalsola arbuscula	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20336	Arctotheca calendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20470	Elaeagnus orientalis	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16409	Quercus pedunculata	Species	Fagaceae	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
IC50	3
Others	1

Activity Type	# Activity
Cell Line	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	48620.0	nM	PMID[501555]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	71520.0	nM	PMID[501555]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	79100.0	nM	PMID[501555]
NPT35	Others	n.a.		Solubility	=	485.02	ug.mL-1	PMID[501555]

☑ 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 NPC4974 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	106
0.1-0.2	673
0.2-0.3	3000
0.3-0.4	11334
0.4-0.5	15505
0.5-0.6	10492
0.6-0.7	1379
0.7-0.8	187
0.8-0.85	17
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9504	High Similarity	NPC210950
0.9504	High Similarity	NPC199738
0.8468	Intermediate Similarity	NPC190663
0.8397	Intermediate Similarity	NPC244866
0.8333	Intermediate Similarity	NPC160493
0.8321	Intermediate Similarity	NPC246913
0.832	Intermediate Similarity	NPC80150
0.8226	Intermediate Similarity	NPC169328
0.816	Intermediate Similarity	NPC310467
0.8136	Intermediate Similarity	NPC211551
0.8099	Intermediate Similarity	NPC319579
0.8092	Intermediate Similarity	NPC296712
0.8045	Intermediate Similarity	NPC45191
0.803	Intermediate Similarity	NPC325651
0.8	Intermediate Similarity	NPC47667
0.792	Intermediate Similarity	NPC197470
0.7891	Intermediate Similarity	NPC476183
0.7891	Intermediate Similarity	NPC45777
0.7891	Intermediate Similarity	NPC477061
0.7877	Intermediate Similarity	NPC56635
0.7874	Intermediate Similarity	NPC237420
0.7863	Intermediate Similarity	NPC12730
0.7846	Intermediate Similarity	NPC35996
0.7829	Intermediate Similarity	NPC476281
0.7829	Intermediate Similarity	NPC476184
0.7823	Intermediate Similarity	NPC474584
0.7812	Intermediate Similarity	NPC319950
0.781	Intermediate Similarity	NPC6570
0.7778	Intermediate Similarity	NPC326966
0.7769	Intermediate Similarity	NPC474862
0.7721	Intermediate Similarity	NPC470392
0.771	Intermediate Similarity	NPC476278
0.7692	Intermediate Similarity	NPC33168
0.768	Intermediate Similarity	NPC273814
0.7667	Intermediate Similarity	NPC164859
0.7652	Intermediate Similarity	NPC476260
0.7652	Intermediate Similarity	NPC476241
0.7634	Intermediate Similarity	NPC27581
0.7634	Intermediate Similarity	NPC142577
0.763	Intermediate Similarity	NPC478147
0.7623	Intermediate Similarity	NPC327481
0.7612	Intermediate Similarity	NPC476353
0.7607	Intermediate Similarity	NPC3371
0.76	Intermediate Similarity	NPC329011
0.7594	Intermediate Similarity	NPC476179
0.7594	Intermediate Similarity	NPC476125
0.7589	Intermediate Similarity	NPC91953
0.7583	Intermediate Similarity	NPC318154
0.7554	Intermediate Similarity	NPC6913
0.7518	Intermediate Similarity	NPC197921
0.7517	Intermediate Similarity	NPC132771
0.7483	Intermediate Similarity	NPC106183
0.7481	Intermediate Similarity	NPC478015
0.7481	Intermediate Similarity	NPC478014
0.7481	Intermediate Similarity	NPC478016
0.7465	Intermediate Similarity	NPC469360
0.7462	Intermediate Similarity	NPC314992
0.7429	Intermediate Similarity	NPC127741
0.7407	Intermediate Similarity	NPC477937
0.7407	Intermediate Similarity	NPC136453
0.7395	Intermediate Similarity	NPC311242
0.7385	Intermediate Similarity	NPC38458
0.7385	Intermediate Similarity	NPC311737
0.7361	Intermediate Similarity	NPC473922
0.7353	Intermediate Similarity	NPC239990
0.7353	Intermediate Similarity	NPC71933
0.7353	Intermediate Similarity	NPC89923
0.7353	Intermediate Similarity	NPC105114
0.7353	Intermediate Similarity	NPC152850
0.7344	Intermediate Similarity	NPC1986
0.7344	Intermediate Similarity	NPC474544
0.7343	Intermediate Similarity	NPC161069
0.731	Intermediate Similarity	NPC81026
0.7308	Intermediate Similarity	NPC2265
0.7308	Intermediate Similarity	NPC82963
0.7299	Intermediate Similarity	NPC111428
0.7299	Intermediate Similarity	NPC473322
0.7299	Intermediate Similarity	NPC469666
0.7279	Intermediate Similarity	NPC65310
0.7279	Intermediate Similarity	NPC254798
0.7278	Intermediate Similarity	NPC159767
0.7278	Intermediate Similarity	NPC155506
0.7252	Intermediate Similarity	NPC470545
0.7241	Intermediate Similarity	NPC266741
0.7241	Intermediate Similarity	NPC209509
0.7214	Intermediate Similarity	NPC328070
0.7214	Intermediate Similarity	NPC313663
0.7203	Intermediate Similarity	NPC265521
0.7203	Intermediate Similarity	NPC153007
0.72	Intermediate Similarity	NPC274089
0.72	Intermediate Similarity	NPC191215
0.7197	Intermediate Similarity	NPC470546
0.7194	Intermediate Similarity	NPC255447
0.7194	Intermediate Similarity	NPC157311
0.7181	Intermediate Similarity	NPC233702
0.7181	Intermediate Similarity	NPC470274
0.7179	Intermediate Similarity	NPC258627
0.7179	Intermediate Similarity	NPC172128
0.7176	Intermediate Similarity	NPC470544
0.7172	Intermediate Similarity	NPC314388
0.7172	Intermediate Similarity	NPC315283
0.7171	Intermediate Similarity	NPC212699
0.7171	Intermediate Similarity	NPC93343
0.7171	Intermediate Similarity	NPC207675
0.717	Intermediate Similarity	NPC279871
0.7167	Intermediate Similarity	NPC25565
0.7154	Intermediate Similarity	NPC33742
0.7152	Intermediate Similarity	NPC89831
0.7152	Intermediate Similarity	NPC230611
0.7143	Intermediate Similarity	NPC138775
0.7143	Intermediate Similarity	NPC8761
0.7143	Intermediate Similarity	NPC275538
0.7143	Intermediate Similarity	NPC44805
0.7143	Intermediate Similarity	NPC246079
0.7133	Intermediate Similarity	NPC473052
0.7133	Intermediate Similarity	NPC473055
0.7133	Intermediate Similarity	NPC77992
0.7132	Intermediate Similarity	NPC473938
0.7132	Intermediate Similarity	NPC285394
0.7123	Intermediate Similarity	NPC316008
0.7123	Intermediate Similarity	NPC313867
0.7107	Intermediate Similarity	NPC137627
0.7107	Intermediate Similarity	NPC293628
0.7107	Intermediate Similarity	NPC475439
0.7107	Intermediate Similarity	NPC473501
0.7107	Intermediate Similarity	NPC10781
0.7107	Intermediate Similarity	NPC306804
0.7107	Intermediate Similarity	NPC122493
0.7099	Intermediate Similarity	NPC317254
0.7097	Intermediate Similarity	NPC471317
0.7095	Intermediate Similarity	NPC105717
0.7086	Intermediate Similarity	NPC39431
0.7086	Intermediate Similarity	NPC275839
0.7083	Intermediate Similarity	NPC161972
0.7083	Intermediate Similarity	NPC303045
0.7083	Intermediate Similarity	NPC322526
0.7083	Intermediate Similarity	NPC58674
0.7077	Intermediate Similarity	NPC276949
0.7077	Intermediate Similarity	NPC35850
0.7075	Intermediate Similarity	NPC314358
0.7073	Intermediate Similarity	NPC294951
0.707	Intermediate Similarity	NPC107938
0.707	Intermediate Similarity	NPC294516
0.7068	Intermediate Similarity	NPC220698
0.7063	Intermediate Similarity	NPC45033
0.7063	Intermediate Similarity	NPC473402
0.7063	Intermediate Similarity	NPC158277
0.7051	Intermediate Similarity	NPC223207
0.7049	Intermediate Similarity	NPC322598
0.7045	Intermediate Similarity	NPC188867
0.7045	Intermediate Similarity	NPC281686
0.7045	Intermediate Similarity	NPC106551
0.704	Intermediate Similarity	NPC88267
0.704	Intermediate Similarity	NPC224610
0.704	Intermediate Similarity	NPC194390
0.704	Intermediate Similarity	NPC113326
0.7037	Intermediate Similarity	NPC273830
0.7037	Intermediate Similarity	NPC194671
0.7037	Intermediate Similarity	NPC269750
0.7034	Intermediate Similarity	NPC263493
0.7034	Intermediate Similarity	NPC269398
0.7031	Intermediate Similarity	NPC292758
0.7031	Intermediate Similarity	NPC65855
0.7027	Intermediate Similarity	NPC135121
0.7027	Intermediate Similarity	NPC475578
0.7027	Intermediate Similarity	NPC16188
0.7023	Intermediate Similarity	NPC118202
0.7021	Intermediate Similarity	NPC257390
0.7015	Intermediate Similarity	NPC43275
0.7009	Intermediate Similarity	NPC325441
0.7007	Intermediate Similarity	NPC201244
0.7007	Intermediate Similarity	NPC477217
0.7006	Intermediate Similarity	NPC471771
0.7006	Intermediate Similarity	NPC290755
0.7006	Intermediate Similarity	NPC304074
0.6987	Remote Similarity	NPC471051
0.6987	Remote Similarity	NPC471052
0.6987	Remote Similarity	NPC471053
0.6986	Remote Similarity	NPC139326
0.6984	Remote Similarity	NPC67043
0.6981	Remote Similarity	NPC476749
0.6981	Remote Similarity	NPC40234
0.6975	Remote Similarity	NPC226438
0.6967	Remote Similarity	NPC324569
0.6966	Remote Similarity	NPC471201
0.6966	Remote Similarity	NPC163392
0.6966	Remote Similarity	NPC239762
0.6959	Remote Similarity	NPC262077
0.6959	Remote Similarity	NPC314114
0.6957	Remote Similarity	NPC476227
0.6957	Remote Similarity	NPC474479
0.6957	Remote Similarity	NPC474847
0.6957	Remote Similarity	NPC26108
0.6953	Remote Similarity	NPC24101
0.6953	Remote Similarity	NPC153690
0.6953	Remote Similarity	NPC96224
0.6949	Remote Similarity	NPC9822
0.6944	Remote Similarity	NPC471265
0.6944	Remote Similarity	NPC471264
0.6944	Remote Similarity	NPC68865

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 NPC4974 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	95
0.1-0.2	388
0.2-0.3	776
0.3-0.4	1552
0.4-0.5	3067
0.5-0.6	2468
0.6-0.7	702
0.7-0.8	101
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.856	High Similarity	NPD5108	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD6624	Discontinued
0.7953	Intermediate Similarity	NPD5981	Approved
0.7951	Intermediate Similarity	NPD3644	Approved
0.7951	Intermediate Similarity	NPD3643	Approved
0.7951	Intermediate Similarity	NPD3642	Approved
0.792	Intermediate Similarity	NPD1348	Approved
0.7786	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD3123	Discovery
0.7704	Intermediate Similarity	NPD3136	Phase 2
0.7704	Intermediate Similarity	NPD4738	Phase 2
0.7698	Intermediate Similarity	NPD6864	Phase 2
0.7698	Intermediate Similarity	NPD6865	Phase 2
0.7674	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4335	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7450	Phase 2
0.7634	Intermediate Similarity	NPD4480	Approved
0.7584	Intermediate Similarity	NPD8019	Approved
0.7576	Intermediate Similarity	NPD2584	Suspended
0.7557	Intermediate Similarity	NPD4135	Approved
0.7557	Intermediate Similarity	NPD4106	Approved
0.7557	Intermediate Similarity	NPD4136	Approved
0.7541	Intermediate Similarity	NPD1040	Phase 2
0.7537	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1758	Phase 1
0.7518	Intermediate Similarity	NPD4621	Approved
0.7518	Intermediate Similarity	NPD4619	Approved
0.75	Intermediate Similarity	NPD5201	Approved
0.75	Intermediate Similarity	NPD4617	Approved
0.75	Intermediate Similarity	NPD4620	Approved
0.75	Intermediate Similarity	NPD5203	Approved
0.75	Intermediate Similarity	NPD6852	Discontinued
0.7483	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3125	Approved
0.7463	Intermediate Similarity	NPD3098	Discontinued
0.7462	Intermediate Similarity	NPD2218	Phase 2
0.7462	Intermediate Similarity	NPD2217	Approved
0.7462	Intermediate Similarity	NPD1759	Phase 1
0.7462	Intermediate Similarity	NPD4479	Discontinued
0.7417	Intermediate Similarity	NPD9712	Approved
0.7405	Intermediate Similarity	NPD4105	Approved
0.7405	Intermediate Similarity	NPD4102	Approved
0.7394	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4806	Approved
0.7368	Intermediate Similarity	NPD4807	Approved
0.7365	Intermediate Similarity	NPD7131	Phase 3
0.7333	Intermediate Similarity	NPD9711	Approved
0.7333	Intermediate Similarity	NPD9710	Approved
0.7324	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5204	Approved
0.7299	Intermediate Similarity	NPD7828	Discontinued
0.7297	Intermediate Similarity	NPD6390	Discontinued
0.7293	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6746	Phase 2
0.7286	Intermediate Similarity	NPD5120	Approved
0.7286	Intermediate Similarity	NPD5119	Approved
0.7286	Intermediate Similarity	NPD5121	Approved
0.7279	Intermediate Similarity	NPD2626	Approved
0.7279	Intermediate Similarity	NPD2628	Approved
0.7279	Intermediate Similarity	NPD2159	Approved
0.7279	Intermediate Similarity	NPD2160	Approved
0.7279	Intermediate Similarity	NPD2627	Approved
0.7279	Intermediate Similarity	NPD2625	Approved
0.7273	Intermediate Similarity	NPD4172	Approved
0.7273	Intermediate Similarity	NPD4173	Approved
0.726	Intermediate Similarity	NPD8323	Discontinued
0.726	Intermediate Similarity	NPD7740	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5618	Discontinued
0.7226	Intermediate Similarity	NPD7451	Discontinued
0.7219	Intermediate Similarity	NPD6502	Phase 2
0.7218	Intermediate Similarity	NPD5305	Approved
0.7218	Intermediate Similarity	NPD5306	Approved
0.7214	Intermediate Similarity	NPD7714	Approved
0.7214	Intermediate Similarity	NPD7715	Approved
0.7192	Intermediate Similarity	NPD3400	Discontinued
0.7183	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4574	Approved
0.7176	Intermediate Similarity	NPD5291	Approved
0.7176	Intermediate Similarity	NPD4576	Approved
0.7176	Intermediate Similarity	NPD5292	Approved
0.7163	Intermediate Similarity	NPD6309	Approved
0.7163	Intermediate Similarity	NPD6311	Approved
0.7163	Intermediate Similarity	NPD6310	Approved
0.7163	Intermediate Similarity	NPD8265	Approved
0.7143	Intermediate Similarity	NPD8011	Discontinued
0.7143	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2607	Approved
0.7132	Intermediate Similarity	NPD5159	Phase 2
0.7132	Intermediate Similarity	NPD5157	Phase 1
0.7132	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7495	Discontinued
0.712	Intermediate Similarity	NPD999	Phase 2
0.7107	Intermediate Similarity	NPD9566	Approved
0.7103	Intermediate Similarity	NPD7978	Discontinued
0.709	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2198	Approved
0.708	Intermediate Similarity	NPD2199	Approved
0.7067	Intermediate Similarity	NPD7613	Discontinued
0.7055	Intermediate Similarity	NPD6681	Discovery
0.705	Intermediate Similarity	NPD4006	Discontinued
0.7045	Intermediate Similarity	NPD9568	Approved
0.7045	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6346	Approved
0.7042	Intermediate Similarity	NPD3373	Approved
0.7037	Intermediate Similarity	NPD3881	Discontinued
0.7031	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1330	Phase 2
0.7014	Intermediate Similarity	NPD6295	Approved
0.7014	Intermediate Similarity	NPD6294	Approved
0.7013	Intermediate Similarity	NPD7011	Discontinued
0.6993	Remote Similarity	NPD555	Phase 2
0.6986	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7437	Approved
0.6985	Remote Similarity	NPD7436	Approved
0.6985	Remote Similarity	NPD6287	Discontinued
0.6981	Remote Similarity	NPD7608	Discontinued
0.6972	Remote Similarity	NPD7477	Discontinued
0.6959	Remote Similarity	NPD7253	Phase 3
0.6957	Remote Similarity	NPD5667	Approved
0.6957	Remote Similarity	NPD6325	Discontinued
0.6948	Remote Similarity	NPD6913	Approved
0.6947	Remote Similarity	NPD2650	Approved
0.6947	Remote Similarity	NPD2652	Approved
0.6935	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5705	Approved
0.6929	Remote Similarity	NPD5706	Approved
0.6929	Remote Similarity	NPD3663	Approved
0.6929	Remote Similarity	NPD3661	Approved
0.6929	Remote Similarity	NPD5704	Approved
0.6929	Remote Similarity	NPD3662	Phase 3
0.6929	Remote Similarity	NPD3664	Approved
0.6923	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6623	Phase 3
0.6905	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5236	Approved
0.6899	Remote Similarity	NPD5235	Approved
0.6899	Remote Similarity	NPD5237	Approved
0.6899	Remote Similarity	NPD5239	Approved
0.6899	Remote Similarity	NPD5240	Approved
0.6894	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6994	Approved
0.6889	Remote Similarity	NPD6993	Approved
0.6884	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.688	Remote Similarity	NPD855	Approved
0.688	Remote Similarity	NPD854	Approved
0.6879	Remote Similarity	NPD4125	Approved
0.6875	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7554	Discontinued
0.6863	Remote Similarity	NPD8315	Phase 1
0.6861	Remote Similarity	NPD4216	Approved
0.6861	Remote Similarity	NPD4217	Approved
0.6861	Remote Similarity	NPD3132	Approved
0.6861	Remote Similarity	NPD2612	Approved
0.6861	Remote Similarity	NPD2609	Approved
0.6861	Remote Similarity	NPD2611	Approved
0.6861	Remote Similarity	NPD3131	Approved
0.6861	Remote Similarity	NPD4218	Approved
0.6861	Remote Similarity	NPD2610	Approved
0.6861	Remote Similarity	NPD4215	Approved
0.6861	Remote Similarity	NPD2608	Approved
0.686	Remote Similarity	NPD1066	Discontinued
0.686	Remote Similarity	NPD1080	Approved
0.6857	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD259	Phase 1
0.6846	Remote Similarity	NPD2575	Approved
0.6842	Remote Similarity	NPD256	Approved
0.6842	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD255	Approved
0.6831	Remote Similarity	NPD6039	Approved
0.6831	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6088	Approved
0.6818	Remote Similarity	NPD3455	Phase 2
0.6815	Remote Similarity	NPD2617	Discontinued
0.6809	Remote Similarity	NPD4175	Approved
0.6809	Remote Similarity	NPD4177	Approved
0.6806	Remote Similarity	NPD826	Approved
0.6806	Remote Similarity	NPD825	Approved
0.6797	Remote Similarity	NPD5982	Phase 2
0.6797	Remote Similarity	NPD7523	Phase 3
0.6795	Remote Similarity	NPD7029	Discontinued
0.6791	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3421	Phase 3
0.6786	Remote Similarity	NPD6564	Approved
0.6786	Remote Similarity	NPD6565	Approved
0.6786	Remote Similarity	NPD6563	Approved
0.6783	Remote Similarity	NPD5299	Approved
0.6777	Remote Similarity	NPD6690	Approved
0.6777	Remote Similarity	NPD1812	Approved
0.6777	Remote Similarity	NPD1814	Approved
0.6774	Remote Similarity	NPD9609	Approved

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