NPASS Compound

Structure

NPC292675 OpenBabel07101718192D 39 46 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 0.6167 2.1694 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 -0.4305 -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 0.0712 1.3313 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1637 3.0609 0.0000 O 0 0 0 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 30 1 0 0 0 0 3 30 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 20 1 0 0 0 0 11 21 2 0 0 0 0 12 22 2 0 0 0 0 13 23 2 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 31 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 36 1 0 0 0 0 19 37 2 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 0 0 0 0 22 33 1 0 0 0 0 23 25 1 0 0 0 0 23 36 1 0 0 0 0 24 34 1 0 0 0 0 24 38 2 0 0 0 0 25 32 1 0 0 0 0 26 27 1 0 0 0 0 26 35 1 6 0 0 0 27 30 1 0 0 0 0 27 39 1 6 0 0 0 28 32 1 1 0 0 0 28 33 1 0 0 0 0 28 36 1 0 0 0 0 29 31 1 6 0 0 0 29 34 1 0 0 0 0 29 35 1 0 0 0 0 30 39 1 0 0 0 0 31 32 1 6 0 0 0 32 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.26
Volume:	537.569
LogP:	4.379
LogD:	3.559
LogS:	-4.862
# Rotatable Bonds:	5
TPSA:	68.42
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	6.661
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.243
MDCK Permeability:	2.527376273064874e-05
Pgp-inhibitor:	0.425
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.966
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	76.7197494506836%
Volume Distribution (VD):	1.956
Pgp-substrate:	13.27933406829834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.564
CYP2C19-substrate:	0.902
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.718
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.857
CYP3A4-substrate:	0.864

ADMET: Excretion

Clearance (CL):	2.907
Half-life (T1/2):	0.326

ADMET: Toxicity

hERG Blockers:	0.567
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.527
AMES Toxicity:	0.365
Rat Oral Acute Toxicity:	0.849
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.671
Carcinogencity:	0.258
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.7

Download Data

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

Natural Product: NPC292675

Natural Product ID:	NPC292675
*Common Name:**	Communesin D
IUPAC Name:	n.a.
Synonyms:	Communesin D
Standard InCHIKey:	BKJFWWFPUSKVTE-NSUYYRTMSA-N
Standard InCHI:	InChI=1S/C32H34N4O3/c1-4-5-6-14-24(38)34-17-15-31-21-11-7-8-12-22(21)33-28-32(31)16-18-35(29(31)34)26(27-30(2,3)39-27)20-10-9-13-23(25(20)32)36(28)19-37/h4-14,19,26-29,33H,15-18H2,1-3H3/b5-4+,14-6+/t26-,27+,28+,29+,31-,32-/m0/s1
SMILES:	C/C=C/C=C/C(=O)N1CC[C@@]23[C@H]1N1CC[C@@]43[C@H](Nc3c2cccc3)N(c2c4c([C@H]1[C@H]1OC1(C)C)ccc2)C=O
Synthetic Gene Cluster:	BGC0001205;
ChEMBL Identifier:	CHEMBL507587
PubChem CID:	44575540
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	=	13.1	ug ml-1	PMID[528809]
NPT1970	Cell Line	THP-1	Homo sapiens	ED50	=	16.2	ug ml-1	PMID[528809]
NPT793	Cell Line	MOLT-3	Homo sapiens	ED50	=	9.9	ug ml-1	PMID[528809]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.57	ug.mL-1	PMID[528809]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	14.6	ug ml-1	PMID[528809]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	9.0	ug ml-1	PMID[528809]
NPT3978	Organism	Bombyx mori	Bombyx mori	LD50	=	80.0	mg.kg-1	PMID[528810]

☑ 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 NPC292675 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	337
0.1-0.2	1483
0.2-0.3	7402
0.3-0.4	23362
0.4-0.5	6682
0.5-0.6	3011
0.6-0.7	373
0.7-0.8	40
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	NPC473615
0.9701	High Similarity	NPC256288
0.9643	High Similarity	NPC2933
0.9586	High Similarity	NPC259626
0.8263	Intermediate Similarity	NPC109787
0.7692	Intermediate Similarity	NPC285622
0.745	Intermediate Similarity	NPC477173
0.7413	Intermediate Similarity	NPC470488
0.7403	Intermediate Similarity	NPC286871
0.7312	Intermediate Similarity	NPC177261
0.7312	Intermediate Similarity	NPC473743
0.7308	Intermediate Similarity	NPC176983
0.7291	Intermediate Similarity	NPC470491
0.7291	Intermediate Similarity	NPC471945
0.7291	Intermediate Similarity	NPC471950
0.7291	Intermediate Similarity	NPC475259
0.7283	Intermediate Similarity	NPC279527
0.7283	Intermediate Similarity	NPC214960
0.7264	Intermediate Similarity	NPC477179
0.7255	Intermediate Similarity	NPC471951
0.7255	Intermediate Similarity	NPC471946
0.7254	Intermediate Similarity	NPC285841
0.7228	Intermediate Similarity	NPC477178
0.7228	Intermediate Similarity	NPC477181
0.7228	Intermediate Similarity	NPC254850
0.7228	Intermediate Similarity	NPC477180
0.7219	Intermediate Similarity	NPC251212
0.7219	Intermediate Similarity	NPC139085
0.7219	Intermediate Similarity	NPC214626
0.7198	Intermediate Similarity	NPC471122
0.7192	Intermediate Similarity	NPC470490
0.7192	Intermediate Similarity	NPC477174
0.7182	Intermediate Similarity	NPC29285
0.7158	Intermediate Similarity	NPC472102
0.7158	Intermediate Similarity	NPC309531
0.7158	Intermediate Similarity	NPC68650
0.715	Intermediate Similarity	NPC307396
0.7143	Intermediate Similarity	NPC470489
0.7143	Intermediate Similarity	NPC113946
0.7136	Intermediate Similarity	NPC475359
0.7136	Intermediate Similarity	NPC191817
0.7135	Intermediate Similarity	NPC471124
0.7135	Intermediate Similarity	NPC477159
0.7135	Intermediate Similarity	NPC472106
0.7129	Intermediate Similarity	NPC471436
0.7119	Intermediate Similarity	NPC264589
0.7104	Intermediate Similarity	NPC276085
0.7062	Intermediate Similarity	NPC476095
0.7056	Intermediate Similarity	NPC66936
0.7056	Intermediate Similarity	NPC25401
0.7049	Intermediate Similarity	NPC222029
0.7047	Intermediate Similarity	NPC159963
0.7037	Intermediate Similarity	NPC242269
0.7027	Intermediate Similarity	NPC472101
0.7027	Intermediate Similarity	NPC85651
0.7027	Intermediate Similarity	NPC472120
0.7005	Intermediate Similarity	NPC473298
0.6984	Remote Similarity	NPC355
0.6981	Remote Similarity	NPC248601
0.6965	Remote Similarity	NPC162440
0.6957	Remote Similarity	NPC285192
0.6952	Remote Similarity	NPC475420
0.6935	Remote Similarity	NPC282339
0.6935	Remote Similarity	NPC99632
0.6934	Remote Similarity	NPC471197
0.6927	Remote Similarity	NPC260075
0.6919	Remote Similarity	NPC105055
0.6919	Remote Similarity	NPC22689
0.6911	Remote Similarity	NPC475097
0.6906	Remote Similarity	NPC473329
0.6904	Remote Similarity	NPC14994
0.6901	Remote Similarity	NPC471198
0.6893	Remote Similarity	NPC329833
0.6884	Remote Similarity	NPC276430
0.6872	Remote Similarity	NPC473006
0.6868	Remote Similarity	NPC475763
0.686	Remote Similarity	NPC225400
0.6859	Remote Similarity	NPC473880
0.6827	Remote Similarity	NPC470786
0.6827	Remote Similarity	NPC472538
0.6827	Remote Similarity	NPC471155
0.6823	Remote Similarity	NPC470548
0.6818	Remote Similarity	NPC181928
0.6818	Remote Similarity	NPC469560
0.6814	Remote Similarity	NPC106118
0.6813	Remote Similarity	NPC318086
0.68	Remote Similarity	NPC471123
0.6794	Remote Similarity	NPC270241
0.6791	Remote Similarity	NPC225319
0.6788	Remote Similarity	NPC264482
0.6788	Remote Similarity	NPC320147
0.6788	Remote Similarity	NPC203202
0.678	Remote Similarity	NPC130251
0.6755	Remote Similarity	NPC472117
0.6754	Remote Similarity	NPC472118
0.675	Remote Similarity	NPC128582
0.6738	Remote Similarity	NPC193410
0.6714	Remote Similarity	NPC471663
0.6702	Remote Similarity	NPC248117
0.67	Remote Similarity	NPC284706
0.67	Remote Similarity	NPC34717
0.6699	Remote Similarity	NPC67904
0.6699	Remote Similarity	NPC138830
0.6684	Remote Similarity	NPC61013
0.6684	Remote Similarity	NPC96901
0.6667	Remote Similarity	NPC470787
0.6667	Remote Similarity	NPC472540
0.6667	Remote Similarity	NPC186669
0.6667	Remote Similarity	NPC472539
0.6634	Remote Similarity	NPC472541
0.6634	Remote Similarity	NPC472542
0.6633	Remote Similarity	NPC99043
0.6633	Remote Similarity	NPC322621
0.6633	Remote Similarity	NPC218594
0.6633	Remote Similarity	NPC475094
0.6633	Remote Similarity	NPC52262
0.6633	Remote Similarity	NPC6974
0.663	Remote Similarity	NPC472103
0.6615	Remote Similarity	NPC223595
0.6615	Remote Similarity	NPC224970
0.6615	Remote Similarity	NPC475248
0.6615	Remote Similarity	NPC63047
0.6615	Remote Similarity	NPC167724
0.6614	Remote Similarity	NPC143457
0.6612	Remote Similarity	NPC212799
0.6602	Remote Similarity	NPC100863
0.6599	Remote Similarity	NPC11149
0.6598	Remote Similarity	NPC476425
0.6584	Remote Similarity	NPC473569
0.6579	Remote Similarity	NPC472121
0.657	Remote Similarity	NPC252794
0.6562	Remote Similarity	NPC472114
0.6562	Remote Similarity	NPC472115
0.6561	Remote Similarity	NPC36495
0.6557	Remote Similarity	NPC472100
0.6556	Remote Similarity	NPC301760
0.6556	Remote Similarity	NPC22082
0.6556	Remote Similarity	NPC186284
0.6555	Remote Similarity	NPC473005
0.6553	Remote Similarity	NPC90967
0.6544	Remote Similarity	NPC15384
0.6544	Remote Similarity	NPC244425
0.6537	Remote Similarity	NPC243626
0.6537	Remote Similarity	NPC230313
0.6532	Remote Similarity	NPC145754
0.6528	Remote Similarity	NPC33507
0.6524	Remote Similarity	NPC478076
0.6524	Remote Similarity	NPC295548
0.6518	Remote Similarity	NPC477176
0.6518	Remote Similarity	NPC470729
0.6518	Remote Similarity	NPC470730
0.6518	Remote Similarity	NPC477175
0.6515	Remote Similarity	NPC286994
0.6514	Remote Similarity	NPC77777
0.6508	Remote Similarity	NPC469428
0.6508	Remote Similarity	NPC123241
0.6505	Remote Similarity	NPC243756
0.65	Remote Similarity	NPC474896
0.6498	Remote Similarity	NPC251936
0.6492	Remote Similarity	NPC293458
0.6489	Remote Similarity	NPC475859
0.6489	Remote Similarity	NPC475969
0.6489	Remote Similarity	NPC474877
0.6484	Remote Similarity	NPC469537
0.6473	Remote Similarity	NPC471199
0.6471	Remote Similarity	NPC31097
0.6471	Remote Similarity	NPC470483
0.6471	Remote Similarity	NPC475915
0.6468	Remote Similarity	NPC473007
0.646	Remote Similarity	NPC165743
0.6456	Remote Similarity	NPC221687
0.6455	Remote Similarity	NPC272174
0.645	Remote Similarity	NPC19679
0.6448	Remote Similarity	NPC311330
0.6447	Remote Similarity	NPC476441
0.6418	Remote Similarity	NPC97584
0.6413	Remote Similarity	NPC116519
0.6408	Remote Similarity	NPC470485
0.6406	Remote Similarity	NPC469741
0.6398	Remote Similarity	NPC14812
0.6396	Remote Similarity	NPC13367
0.6382	Remote Similarity	NPC321211
0.6373	Remote Similarity	NPC313757
0.6372	Remote Similarity	NPC223242
0.6372	Remote Similarity	NPC477160
0.6359	Remote Similarity	NPC473004
0.6354	Remote Similarity	NPC474058
0.6346	Remote Similarity	NPC473375
0.6346	Remote Similarity	NPC97100
0.6343	Remote Similarity	NPC126066
0.6341	Remote Similarity	NPC473008
0.6333	Remote Similarity	NPC267508
0.6332	Remote Similarity	NPC476326
0.633	Remote Similarity	NPC154602
0.6327	Remote Similarity	NPC469915
0.6326	Remote Similarity	NPC71238
0.6321	Remote Similarity	NPC52801
0.6316	Remote Similarity	NPC139373
0.6313	Remote Similarity	NPC469726

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 NPC292675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	512
0.2-0.3	719
0.3-0.4	1661
0.4-0.5	3758
0.5-0.6	2161
0.6-0.7	150
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
0.7062	Intermediate Similarity	NPD7785	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8240	Discontinued
0.6771	Remote Similarity	NPD5997	Discontinued
0.6758	Remote Similarity	NPD5942	Approved
0.6758	Remote Similarity	NPD5941	Approved
0.6757	Remote Similarity	NPD5743	Approved
0.6757	Remote Similarity	NPD5742	Approved
0.6757	Remote Similarity	NPD5741	Approved
0.6753	Remote Similarity	NPD5600	Discontinued
0.6748	Remote Similarity	NPD6238	Discontinued
0.6703	Remote Similarity	NPD4120	Approved
0.6703	Remote Similarity	NPD4121	Phase 3
0.6684	Remote Similarity	NPD6879	Phase 2
0.6684	Remote Similarity	NPD6878	Phase 2
0.665	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6557	Phase 2
0.6528	Remote Similarity	NPD7890	Discontinued
0.6522	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7824	Approved
0.6513	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7854	Phase 2
0.6484	Remote Similarity	NPD4430	Phase 2
0.648	Remote Similarity	NPD5318	Discontinued
0.6429	Remote Similarity	NPD7730	Approved
0.6429	Remote Similarity	NPD6768	Approved
0.6429	Remote Similarity	NPD7731	Approved
0.6421	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7271	Approved
0.6404	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5024	Approved
0.6389	Remote Similarity	NPD6342	Discontinued
0.6387	Remote Similarity	NPD7599	Phase 2
0.6386	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD1950	Approved
0.6379	Remote Similarity	NPD1949	Approved
0.6379	Remote Similarity	NPD3240	Phase 2
0.6373	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8263	Discontinued
0.6354	Remote Similarity	NPD7600	Phase 2
0.6344	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD8630	Approved
0.6333	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6483	Approved
0.6324	Remote Similarity	NPD6484	Approved
0.6322	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7072	Phase 2
0.6311	Remote Similarity	NPD5042	Phase 1
0.6304	Remote Similarity	NPD6301	Phase 2
0.6298	Remote Similarity	NPD6358	Phase 2
0.6289	Remote Similarity	NPD3790	Phase 2
0.6288	Remote Similarity	NPD7952	Approved
0.6288	Remote Similarity	NPD7951	Approved
0.6288	Remote Similarity	NPD7789	Approved
0.6288	Remote Similarity	NPD7791	Approved
0.6288	Remote Similarity	NPD7953	Approved
0.6288	Remote Similarity	NPD7790	Approved
0.6288	Remote Similarity	NPD7950	Approved
0.6284	Remote Similarity	NPD2093	Discontinued
0.6284	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD3625	Discontinued
0.6283	Remote Similarity	NPD7105	Phase 1
0.6281	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD5830	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7688	Phase 1
0.6271	Remote Similarity	NPD4365	Phase 2
0.627	Remote Similarity	NPD5918	Discontinued
0.627	Remote Similarity	NPD7487	Discontinued
0.6267	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD8114	Approved
0.6262	Remote Similarity	NPD8115	Approved
0.6262	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD5186	Approved
0.6244	Remote Similarity	NPD5183	Approved
0.6237	Remote Similarity	NPD5060	Phase 1
0.6237	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD8128	Discontinued
0.6222	Remote Similarity	NPD5182	Approved
0.6222	Remote Similarity	NPD5185	Approved
0.6222	Remote Similarity	NPD5184	Approved
0.6219	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD7775	Approved
0.6218	Remote Similarity	NPD4393	Approved
0.6218	Remote Similarity	NPD33	Approved
0.6218	Remote Similarity	NPD3388	Phase 1
0.6216	Remote Similarity	NPD2820	Phase 3
0.6211	Remote Similarity	NPD8400	Approved
0.6211	Remote Similarity	NPD8401	Approved
0.6211	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6978	Phase 2
0.6211	Remote Similarity	NPD8402	Approved
0.6205	Remote Similarity	NPD7726	Phase 1
0.6198	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD3983	Phase 3
0.6193	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6644	Discontinued
0.6186	Remote Similarity	NPD7921	Approved
0.6183	Remote Similarity	NPD2387	Approved
0.6178	Remote Similarity	NPD2790	Discontinued
0.6176	Remote Similarity	NPD6069	Approved
0.6176	Remote Similarity	NPD6070	Approved
0.6169	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD8060	Phase 1
0.6164	Remote Similarity	NPD7595	Discontinued
0.6162	Remote Similarity	NPD2365	Approved
0.6162	Remote Similarity	NPD5531	Discontinued
0.6154	Remote Similarity	NPD6272	Phase 1
0.615	Remote Similarity	NPD5932	Phase 3
0.615	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.615	Remote Similarity	NPD5931	Phase 3
0.615	Remote Similarity	NPD5933	Phase 3
0.6138	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD3248	Phase 1
0.6124	Remote Similarity	NPD7569	Approved
0.6124	Remote Similarity	NPD7570	Approved
0.612	Remote Similarity	NPD6295	Approved
0.612	Remote Similarity	NPD6294	Approved
0.6119	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6395	Phase 2
0.6114	Remote Similarity	NPD1663	Discontinued
0.6108	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4499	Approved
0.6106	Remote Similarity	NPD6995	Phase 1
0.6106	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD2791	Discontinued
0.6099	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5179	Approved
0.6095	Remote Similarity	NPD2914	Approved
0.6095	Remote Similarity	NPD2913	Approved
0.6095	Remote Similarity	NPD5180	Approved
0.6095	Remote Similarity	NPD5181	Approved
0.6094	Remote Similarity	NPD5086	Approved
0.6091	Remote Similarity	NPD4796	Discontinued
0.6091	Remote Similarity	NPD7035	Approved
0.6091	Remote Similarity	NPD7036	Phase 3
0.6087	Remote Similarity	NPD7254	Discontinued
0.6085	Remote Similarity	NPD1801	Approved
0.6085	Remote Similarity	NPD1802	Approved
0.6082	Remote Similarity	NPD1769	Discontinued
0.6079	Remote Similarity	NPD7717	Approved
0.6079	Remote Similarity	NPD7716	Approved
0.6075	Remote Similarity	NPD6566	Discontinued
0.607	Remote Similarity	NPD7940	Phase 3
0.6068	Remote Similarity	NPD8167	Discontinued
0.6067	Remote Similarity	NPD5993	Phase 1
0.6065	Remote Similarity	NPD6176	Phase 1
0.6064	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6037	Discontinued
0.6059	Remote Similarity	NPD7881	Approved
0.6056	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD4781	Approved
0.6056	Remote Similarity	NPD4783	Approved
0.6055	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD7939	Discontinued
0.6053	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5423	Phase 2
0.6049	Remote Similarity	NPD8281	Discontinued
0.6047	Remote Similarity	NPD6321	Discontinued
0.6043	Remote Similarity	NPD7781	Approved
0.6043	Remote Similarity	NPD7780	Approved
0.6042	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD3789	Approved
0.6032	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD2010	Phase 3
0.6021	Remote Similarity	NPD5748	Phase 2
0.6018	Remote Similarity	NPD3437	Discontinued
0.6011	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD2840	Approved
0.601	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.601	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.601	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.601	Remote Similarity	NPD4976	Discontinued
0.6009	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD7572	Phase 2
0.6	Remote Similarity	NPD5576	Approved
0.6	Remote Similarity	NPD6659	Phase 2
0.6	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8165	Discontinued
0.6	Remote Similarity	NPD5579	Approved
0.6	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7454	Approved
0.5991	Remote Similarity	NPD7455	Approved
0.599	Remote Similarity	NPD1742	Approved
0.599	Remote Similarity	NPD19	Approved
0.599	Remote Similarity	NPD1743	Approved
0.599	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8322	Phase 2
0.5981	Remote Similarity	NPD5071	Phase 2
0.5981	Remote Similarity	NPD8025	Phase 2
0.5981	Remote Similarity	NPD6608	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