NPASS Compound

Structure

NPC473615 OpenBabel07101718332D 37 44 0 0 1 0 0 0 0 0999 V2000 -5.0778 -4.8840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9227 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0567 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0796 -4.9438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5287 -4.1093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5305 -4.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7575 -1.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2435 -1.2826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9793 1.8209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3802 1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0134 -1.7295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9855 -0.5724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2304 1.9053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9796 -3.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8346 -1.5509 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 0.5685 -2.5149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7554 -1.0193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2414 -0.4407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6974 1.3724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9814 -3.3943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1906 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4199 0.6451 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0567 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0921 0.3000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0712 1.3313 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4305 -2.5597 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -1.4010 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.5340 -4.2887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0567 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 29 1 0 0 0 0 3 29 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 14 2 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 21 2 0 0 0 0 13 22 2 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 17 34 1 0 0 0 0 18 35 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 0 0 0 0 21 32 1 0 0 0 0 22 24 1 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 23 36 2 0 0 0 0 24 31 1 0 0 0 0 25 26 1 0 0 0 0 25 35 1 6 0 0 0 26 29 1 0 0 0 0 26 37 1 6 0 0 0 27 31 1 1 0 0 0 27 32 1 0 0 0 0 27 33 1 0 0 0 0 28 30 1 6 0 0 0 28 34 1 0 0 0 0 28 35 1 0 0 0 0 29 37 1 0 0 0 0 30 31 1 6 0 0 0 31 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.27
Volume:	514.12
LogP:	4.155
LogD:	3.866
LogS:	-4.533
# Rotatable Bonds:	4
TPSA:	60.14
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	6.558
Fsp3:	0.452
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.302
MDCK Permeability:	2.4162454792531207e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.203
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	93.46471405029297%
Volume Distribution (VD):	1.705
Pgp-substrate:	5.711163520812988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.702
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.689
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.685
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.828

ADMET: Excretion

Clearance (CL):	3.617
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.792
Drug-inuced Liver Injury (DILI):	0.221
AMES Toxicity:	0.653
Rat Oral Acute Toxicity:	0.796
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.788
Carcinogencity:	0.117
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.656

Download Data

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

Natural Product: NPC473615

Natural Product ID:	NPC473615
*Common Name:**	Communesin C
IUPAC Name:	n.a.
Synonyms:	Communesin C
Standard InCHIKey:	NGWRTMWKLOPVRM-SNBYXLDTSA-N
Standard InCHI:	InChI=1S/C31H34N4O2/c1-4-5-6-14-23(36)34-17-15-30-20-11-7-8-12-21(20)32-27-31(30)16-18-35(28(30)34)25(26-29(2,3)37-26)19-10-9-13-22(33-27)24(19)31/h4-14,25-28,32-33H,15-18H2,1-3H3/b5-4+,14-6+/t25-,26+,27+,28+,30-,31-/m0/s1
SMILES:	C/C=C/C=C/C(=O)N1CC[C@@]23[C@H]1N1CC[C@@]43[C@H](Nc3c2cccc3)Nc2c4c([C@H]1[C@H]1OC1(C)C)ccc2
Synthetic Gene Cluster:	BGC0001205;
ChEMBL Identifier:	CHEMBL447208
PubChem CID:	44575538
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001913] Alpha carbolines

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15056914]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270557]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20415462]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24024763]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO28107	Penicillium expansum	Species	Aspergillaceae	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
ED50	5
LD50	1
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	ED50	=	11.3	ug ml-1	PMID[502157]
NPT1970	Cell Line	THP-1	Homo sapiens	ED50	=	13.1	ug ml-1	PMID[502157]
NPT793	Cell Line	MOLT-3	Homo sapiens	ED50	=	8.6	ug ml-1	PMID[502157]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	1.96	ug.mL-1	PMID[502157]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.2	ug ml-1	PMID[502157]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	10.8	ug ml-1	PMID[502157]
NPT3978	Organism	Bombyx mori	Bombyx mori	LD50	=	300.0	mg.kg-1	PMID[502158]

☑ 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 NPC473615 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	332
0.1-0.2	1470
0.2-0.3	7215
0.3-0.4	23456
0.4-0.5	6645
0.5-0.6	3136
0.6-0.7	391
0.7-0.8	45
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.994	High Similarity	NPC229484
0.988	High Similarity	NPC292675
0.9818	High Similarity	NPC256288
0.9759	High Similarity	NPC2933
0.9701	High Similarity	NPC259626
0.8364	Intermediate Similarity	NPC109787
0.7778	Intermediate Similarity	NPC285622
0.7525	Intermediate Similarity	NPC477173
0.7487	Intermediate Similarity	NPC470488
0.7486	Intermediate Similarity	NPC286871
0.7391	Intermediate Similarity	NPC177261
0.7389	Intermediate Similarity	NPC176983
0.7363	Intermediate Similarity	NPC279527
0.7363	Intermediate Similarity	NPC214960
0.7337	Intermediate Similarity	NPC477179
0.73	Intermediate Similarity	NPC477180
0.73	Intermediate Similarity	NPC477181
0.73	Intermediate Similarity	NPC254850
0.73	Intermediate Similarity	NPC477178
0.7297	Intermediate Similarity	NPC139085
0.7297	Intermediate Similarity	NPC473743
0.7297	Intermediate Similarity	NPC251212
0.7297	Intermediate Similarity	NPC214626
0.7278	Intermediate Similarity	NPC471122
0.7277	Intermediate Similarity	NPC471945
0.7277	Intermediate Similarity	NPC471950
0.7277	Intermediate Similarity	NPC475259
0.7277	Intermediate Similarity	NPC470491
0.7264	Intermediate Similarity	NPC470490
0.7264	Intermediate Similarity	NPC477174
0.7263	Intermediate Similarity	NPC29285
0.7241	Intermediate Similarity	NPC471951
0.7241	Intermediate Similarity	NPC471946
0.724	Intermediate Similarity	NPC285841
0.7238	Intermediate Similarity	NPC472102
0.7238	Intermediate Similarity	NPC309531
0.7238	Intermediate Similarity	NPC68650
0.7222	Intermediate Similarity	NPC113946
0.7214	Intermediate Similarity	NPC470489
0.7213	Intermediate Similarity	NPC471124
0.7213	Intermediate Similarity	NPC472106
0.7211	Intermediate Similarity	NPC477159
0.72	Intermediate Similarity	NPC264589
0.7135	Intermediate Similarity	NPC307396
0.7128	Intermediate Similarity	NPC25401
0.7127	Intermediate Similarity	NPC222029
0.7122	Intermediate Similarity	NPC475359
0.7122	Intermediate Similarity	NPC191817
0.712	Intermediate Similarity	NPC159963
0.7114	Intermediate Similarity	NPC471436
0.7104	Intermediate Similarity	NPC85651
0.7104	Intermediate Similarity	NPC472120
0.7104	Intermediate Similarity	NPC472101
0.7088	Intermediate Similarity	NPC276085
0.7059	Intermediate Similarity	NPC355
0.7048	Intermediate Similarity	NPC248601
0.7047	Intermediate Similarity	NPC476095
0.7024	Intermediate Similarity	NPC285192
0.7021	Intermediate Similarity	NPC242269
0.7011	Intermediate Similarity	NPC99632
0.7011	Intermediate Similarity	NPC282339
0.7	Intermediate Similarity	NPC471197
0.7	Intermediate Similarity	NPC260075
0.699	Remote Similarity	NPC473298
0.699	Remote Similarity	NPC22689
0.699	Remote Similarity	NPC105055
0.6983	Remote Similarity	NPC473329
0.6974	Remote Similarity	NPC14994
0.6967	Remote Similarity	NPC471198
0.695	Remote Similarity	NPC162440
0.6944	Remote Similarity	NPC475763
0.6944	Remote Similarity	NPC66936
0.6935	Remote Similarity	NPC475420
0.6927	Remote Similarity	NPC225400
0.6897	Remote Similarity	NPC469560
0.6895	Remote Similarity	NPC475097
0.6895	Remote Similarity	NPC470548
0.6893	Remote Similarity	NPC472538
0.6893	Remote Similarity	NPC471155
0.6893	Remote Similarity	NPC470786
0.6889	Remote Similarity	NPC318086
0.6888	Remote Similarity	NPC181928
0.6881	Remote Similarity	NPC106118
0.6879	Remote Similarity	NPC471123
0.6878	Remote Similarity	NPC329833
0.6869	Remote Similarity	NPC276430
0.6865	Remote Similarity	NPC225319
0.686	Remote Similarity	NPC270241
0.6859	Remote Similarity	NPC264482
0.6859	Remote Similarity	NPC203202
0.6857	Remote Similarity	NPC130251
0.6857	Remote Similarity	NPC473006
0.6842	Remote Similarity	NPC473880
0.6828	Remote Similarity	NPC472117
0.6825	Remote Similarity	NPC472118
0.6818	Remote Similarity	NPC128582
0.6811	Remote Similarity	NPC193410
0.6774	Remote Similarity	NPC248117
0.6771	Remote Similarity	NPC320147
0.6768	Remote Similarity	NPC284706
0.6765	Remote Similarity	NPC67904
0.6765	Remote Similarity	NPC138830
0.6757	Remote Similarity	NPC61013
0.6754	Remote Similarity	NPC96901
0.6736	Remote Similarity	NPC186669
0.6733	Remote Similarity	NPC470787
0.6733	Remote Similarity	NPC472539
0.6733	Remote Similarity	NPC472540
0.6704	Remote Similarity	NPC472103
0.6701	Remote Similarity	NPC6974
0.6701	Remote Similarity	NPC475094
0.6701	Remote Similarity	NPC218594
0.6701	Remote Similarity	NPC322621
0.6701	Remote Similarity	NPC52262
0.6701	Remote Similarity	NPC99043
0.67	Remote Similarity	NPC472542
0.67	Remote Similarity	NPC472541
0.6698	Remote Similarity	NPC471663
0.6685	Remote Similarity	NPC212799
0.6684	Remote Similarity	NPC143457
0.6684	Remote Similarity	NPC167724
0.6684	Remote Similarity	NPC224970
0.6684	Remote Similarity	NPC223595
0.6683	Remote Similarity	NPC34717
0.6667	Remote Similarity	NPC476425
0.6667	Remote Similarity	NPC11149
0.6667	Remote Similarity	NPC100863
0.665	Remote Similarity	NPC473569
0.6649	Remote Similarity	NPC472121
0.6647	Remote Similarity	NPC252794
0.6632	Remote Similarity	NPC472114
0.6632	Remote Similarity	NPC472115
0.6631	Remote Similarity	NPC36495
0.663	Remote Similarity	NPC472100
0.6629	Remote Similarity	NPC186284
0.6629	Remote Similarity	NPC22082
0.6629	Remote Similarity	NPC301760
0.6618	Remote Similarity	NPC90967
0.6608	Remote Similarity	NPC145754
0.6605	Remote Similarity	NPC244425
0.6605	Remote Similarity	NPC15384
0.6601	Remote Similarity	NPC243626
0.6601	Remote Similarity	NPC230313
0.6597	Remote Similarity	NPC63047
0.6597	Remote Similarity	NPC475248
0.6597	Remote Similarity	NPC33507
0.6595	Remote Similarity	NPC478076
0.6587	Remote Similarity	NPC295548
0.6578	Remote Similarity	NPC469428
0.6578	Remote Similarity	NPC123241
0.6577	Remote Similarity	NPC470730
0.6577	Remote Similarity	NPC477176
0.6577	Remote Similarity	NPC477175
0.6577	Remote Similarity	NPC470729
0.6576	Remote Similarity	NPC243756
0.6574	Remote Similarity	NPC77777
0.6561	Remote Similarity	NPC293458
0.6556	Remote Similarity	NPC469537
0.6548	Remote Similarity	NPC475915
0.6547	Remote Similarity	NPC474877
0.6547	Remote Similarity	NPC475969
0.6547	Remote Similarity	NPC475859
0.6538	Remote Similarity	NPC473005
0.6537	Remote Similarity	NPC471199
0.6535	Remote Similarity	NPC470483
0.6533	Remote Similarity	NPC473007
0.652	Remote Similarity	NPC221687
0.6519	Remote Similarity	NPC311330
0.6518	Remote Similarity	NPC165743
0.6515	Remote Similarity	NPC19679
0.6514	Remote Similarity	NPC272174
0.6513	Remote Similarity	NPC476441
0.6497	Remote Similarity	NPC286994
0.6484	Remote Similarity	NPC116519
0.6484	Remote Similarity	NPC474896
0.6482	Remote Similarity	NPC97584
0.6481	Remote Similarity	NPC251936
0.6471	Remote Similarity	NPC470485
0.6462	Remote Similarity	NPC13367
0.6455	Remote Similarity	NPC31097
0.6447	Remote Similarity	NPC321211
0.644	Remote Similarity	NPC313757
0.6432	Remote Similarity	NPC477160
0.6421	Remote Similarity	NPC474058
0.6408	Remote Similarity	NPC97100
0.6408	Remote Similarity	NPC473375
0.6404	Remote Similarity	NPC267508
0.6404	Remote Similarity	NPC473008
0.6398	Remote Similarity	NPC154602
0.6396	Remote Similarity	NPC476326
0.6392	Remote Similarity	NPC469915
0.6387	Remote Similarity	NPC469741
0.6385	Remote Similarity	NPC71238
0.6383	Remote Similarity	NPC14812
0.6378	Remote Similarity	NPC329338
0.6378	Remote Similarity	NPC469726
0.6364	Remote Similarity	NPC475489
0.6364	Remote Similarity	NPC122106
0.6356	Remote Similarity	NPC223242
0.635	Remote Similarity	NPC472109

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 NPC473615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	511
0.2-0.3	703
0.3-0.4	1642
0.4-0.5	3690
0.5-0.6	2251
0.6-0.7	166
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7045	Intermediate Similarity	NPD7785	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD8240	Discontinued
0.6842	Remote Similarity	NPD5997	Discontinued
0.6833	Remote Similarity	NPD5941	Approved
0.6833	Remote Similarity	NPD5942	Approved
0.6831	Remote Similarity	NPD5741	Approved
0.6831	Remote Similarity	NPD5743	Approved
0.6831	Remote Similarity	NPD5742	Approved
0.6823	Remote Similarity	NPD5600	Discontinued
0.6814	Remote Similarity	NPD6238	Discontinued
0.6776	Remote Similarity	NPD4120	Approved
0.6776	Remote Similarity	NPD4121	Phase 3
0.6753	Remote Similarity	NPD6878	Phase 2
0.6753	Remote Similarity	NPD6879	Phase 2
0.6719	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6557	Phase 2
0.658	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4430	Phase 2
0.6554	Remote Similarity	NPD5318	Discontinued
0.651	Remote Similarity	NPD7890	Discontinued
0.6503	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7824	Approved
0.65	Remote Similarity	NPD6768	Approved
0.6495	Remote Similarity	NPD7854	Phase 2
0.6489	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7271	Approved
0.6464	Remote Similarity	NPD5024	Approved
0.6461	Remote Similarity	NPD6342	Discontinued
0.6455	Remote Similarity	NPD7599	Phase 2
0.6453	Remote Similarity	NPD1949	Approved
0.6453	Remote Similarity	NPD3240	Phase 2
0.6453	Remote Similarity	NPD1950	Approved
0.645	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7600	Phase 2
0.6413	Remote Similarity	NPD7731	Approved
0.6413	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7730	Approved
0.6404	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6484	Approved
0.6386	Remote Similarity	NPD6483	Approved
0.6386	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7072	Phase 2
0.6374	Remote Similarity	NPD6301	Phase 2
0.6373	Remote Similarity	NPD5042	Phase 1
0.6369	Remote Similarity	NPD6358	Phase 2
0.6354	Remote Similarity	NPD3790	Phase 2
0.6354	Remote Similarity	NPD2093	Discontinued
0.6354	Remote Similarity	NPD3625	Discontinued
0.6349	Remote Similarity	NPD7105	Phase 1
0.6343	Remote Similarity	NPD8263	Discontinued
0.6343	Remote Similarity	NPD4365	Phase 2
0.6343	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5830	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7487	Discontinued
0.6339	Remote Similarity	NPD5918	Discontinued
0.6331	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8630	Approved
0.6308	Remote Similarity	NPD5186	Approved
0.6308	Remote Similarity	NPD5183	Approved
0.6304	Remote Similarity	NPD5060	Phase 1
0.6302	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5182	Approved
0.6292	Remote Similarity	NPD5184	Approved
0.6292	Remote Similarity	NPD5185	Approved
0.6284	Remote Similarity	NPD2820	Phase 3
0.6283	Remote Similarity	NPD33	Approved
0.6283	Remote Similarity	NPD3388	Phase 1
0.6283	Remote Similarity	NPD4393	Approved
0.6281	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7951	Approved
0.6272	Remote Similarity	NPD7791	Approved
0.6272	Remote Similarity	NPD7790	Approved
0.6272	Remote Similarity	NPD7789	Approved
0.6272	Remote Similarity	NPD7953	Approved
0.6272	Remote Similarity	NPD7952	Approved
0.6272	Remote Similarity	NPD7950	Approved
0.6267	Remote Similarity	NPD6978	Phase 2
0.6267	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7688	Phase 1
0.6256	Remote Similarity	NPD3983	Phase 3
0.625	Remote Similarity	NPD2387	Approved
0.625	Remote Similarity	NPD6069	Approved
0.625	Remote Similarity	NPD6070	Approved
0.6244	Remote Similarity	NPD8115	Approved
0.6244	Remote Similarity	NPD6644	Discontinued
0.6244	Remote Similarity	NPD8114	Approved
0.6243	Remote Similarity	NPD2790	Discontinued
0.6236	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.623	Remote Similarity	NPD2365	Approved
0.6224	Remote Similarity	NPD5531	Discontinued
0.6221	Remote Similarity	NPD7595	Discontinued
0.6216	Remote Similarity	NPD5931	Phase 3
0.6216	Remote Similarity	NPD5933	Phase 3
0.6216	Remote Similarity	NPD5932	Phase 3
0.6214	Remote Similarity	NPD6272	Phase 1
0.6207	Remote Similarity	NPD8128	Discontinued
0.6203	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7775	Approved
0.6193	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3248	Phase 1
0.619	Remote Similarity	NPD8400	Approved
0.619	Remote Similarity	NPD8402	Approved
0.619	Remote Similarity	NPD8401	Approved
0.6188	Remote Similarity	NPD6294	Approved
0.6188	Remote Similarity	NPD6295	Approved
0.6188	Remote Similarity	NPD7726	Phase 1
0.6184	Remote Similarity	NPD7569	Approved
0.6184	Remote Similarity	NPD7570	Approved
0.6181	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD1663	Discontinued
0.6178	Remote Similarity	NPD6395	Phase 2
0.6178	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7921	Approved
0.6169	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5181	Approved
0.6168	Remote Similarity	NPD5180	Approved
0.6168	Remote Similarity	NPD2913	Approved
0.6168	Remote Similarity	NPD2914	Approved
0.6168	Remote Similarity	NPD5179	Approved
0.6167	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD2791	Discontinued
0.6165	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD4499	Approved
0.6161	Remote Similarity	NPD6995	Phase 1
0.6158	Remote Similarity	NPD5086	Approved
0.6154	Remote Similarity	NPD7036	Phase 3
0.6154	Remote Similarity	NPD4796	Discontinued
0.6154	Remote Similarity	NPD7035	Approved
0.6154	Remote Similarity	NPD7254	Discontinued
0.615	Remote Similarity	NPD1802	Approved
0.615	Remote Similarity	NPD1801	Approved
0.6146	Remote Similarity	NPD1769	Discontinued
0.6146	Remote Similarity	NPD8060	Phase 1
0.6141	Remote Similarity	NPD6566	Discontinued
0.6136	Remote Similarity	NPD5993	Phase 1
0.6131	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4783	Approved
0.6124	Remote Similarity	NPD4781	Approved
0.6122	Remote Similarity	NPD6037	Discontinued
0.6121	Remote Similarity	NPD6176	Phase 1
0.6117	Remote Similarity	NPD5423	Phase 2
0.6117	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD3789	Approved
0.6096	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD2010	Phase 3
0.6085	Remote Similarity	NPD5748	Phase 2
0.608	Remote Similarity	NPD2840	Approved
0.6075	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4976	Discontinued
0.607	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD5576	Approved
0.6069	Remote Similarity	NPD5579	Approved
0.6068	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7572	Phase 2
0.6064	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD7717	Approved
0.6062	Remote Similarity	NPD7716	Approved
0.6058	Remote Similarity	NPD6659	Phase 2
0.6051	Remote Similarity	NPD1743	Approved
0.6051	Remote Similarity	NPD1742	Approved
0.6051	Remote Similarity	NPD19	Approved
0.605	Remote Similarity	NPD7940	Phase 3
0.605	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD8167	Discontinued
0.6048	Remote Similarity	NPD2038	Approved
0.6048	Remote Similarity	NPD3001	Approved
0.6048	Remote Similarity	NPD2039	Approved
0.6048	Remote Similarity	NPD2999	Approved
0.6047	Remote Similarity	NPD1922	Discontinued
0.6045	Remote Similarity	NPD6259	Discontinued
0.6045	Remote Similarity	NPD7455	Approved
0.6045	Remote Similarity	NPD7454	Approved
0.6044	Remote Similarity	NPD6544	Discontinued
0.6043	Remote Similarity	NPD6622	Phase 1
0.6043	Remote Similarity	NPD6485	Discontinued
0.604	Remote Similarity	NPD7479	Phase 2
0.604	Remote Similarity	NPD7881	Approved
0.6039	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5071	Phase 2
0.6038	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6489	Phase 3

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