NPASS Compound

Structure

CID37548 OpenBabel06191715372D 24 26 0 0 1 0 0 0 0 0999 V2000 3.9811 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6150 4.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6150 3.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0495 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3175 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0495 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3175 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5743 2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4811 4.0975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9756 3.1270 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 0.4158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3164 -1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 12 2 0 0 0 0 9 14 2 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 2 1 6 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 16 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	323.16
Volume:	340.99
LogP:	3.155
LogD:	2.737
LogS:	-3.836
# Rotatable Bonds:	4
TPSA:	81.77
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	3.196
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.084
MDCK Permeability:	1.990027703868691e-05
Pgp-inhibitor:	0.876
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.644
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	98.65408325195312%
Volume Distribution (VD):	0.273
Pgp-substrate:	1.4207730293273926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.296
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.349
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.614
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.666
CYP2D6-substrate:	0.648
CYP3A4-inhibitor:	0.768
CYP3A4-substrate:	0.693

ADMET: Excretion

Clearance (CL):	2.996
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.103
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC37548

Natural Product ID:	NPC37548
*Common Name:**	Neoechinulin A
IUPAC Name:	(3S,6Z)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]piperazine-2,5-dione
Synonyms:
Standard InCHIKey:	MYRPIYZIAHOECW-SAIXKJTDSA-N
Standard InCHI:	InChI=1S/C19H21N3O2/c1-5-19(3,4)16-13(12-8-6-7-9-14(12)21-16)10-15-18(24)20-11(2)17(23)22-15/h5-11,21H,1H2,2-4H3,(H,20,24)(H,22,23)/b15-10-/t11-/m0/s1
SMILES:	C=CC(c1[nH]c2c(c1/C=C/1N=C(O)[C@@H](N=C1O)C)cccc2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400768
PubChem CID:	9996305
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

*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
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00010a040]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	root	n.a.	PMID[16078700]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17896816]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17965475]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	roots	Gabon	1987	PMID[18327911]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23848163]
NPO32640	eurotium rubrum ma-150	Species	Aspergillaceae	Eukaryota	Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil.	n.a.	n.a.	PMID[25730346]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26938998]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	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	1
Kd	2
LD50	1
MIC	1
Others	16

Activity Type	# Activity
Cell Line	8
Individual Protein	5
NON-MOLECULAR	1
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	Activity	=	0.27	ug ml-1	PMID[458641]
NPT168	Cell Line	P388	Mus musculus	Activity	=	0.21	ug ml-1	PMID[458641]
NPT377	Cell Line	OVCAR-3	Homo sapiens	Activity	=	0.24	ug ml-1	PMID[458641]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	0.21	ug ml-1	PMID[458641]
NPT575	Cell Line	KM-20L2	Homo sapiens	Activity	=	0.19	ug ml-1	PMID[458641]
NPT1081	Cell Line	BXPC-3	Homo sapiens	Activity	=	0.25	ug ml-1	PMID[458641]
NPT399	Cell Line	SF-295	Homo sapiens	Activity	=	0.21	ug ml-1	PMID[458641]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	200000.0	nM	PMID[458643]
NPT2704	Individual Protein	Hemagglutinin	Influenza A virus	Kd	=	98000.0	nM	PMID[458643]
NPT2704	Individual Protein	Hemagglutinin	Influenza A virus	Activity	=	26.5	n.a.	PMID[458643]
NPT2704	Individual Protein	Hemagglutinin	Influenza A virus	Activity	=	12.3	n.a.	PMID[458643]
NPT2704	Individual Protein	Hemagglutinin	Influenza A virus	Activity	=	4.5	n.a.	PMID[458643]
NPT2704	Individual Protein	Hemagglutinin	Influenza A virus	Activity	=	1.0	n.a.	PMID[458643]
NPT35	Others	n.a.		IC50	=	103000.0	nM	PMID[458640]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	100.0	ug.mL-1	PMID[458642]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	35.9	%	PMID[458643]
NPT2	Others	Unspecified		Kd	=	83000.0	nM	PMID[458643]
NPT2	Others	Unspecified		Activity	=	119.0	n.a.	PMID[458643]
NPT2	Others	Unspecified		Activity	=	58.0	n.a.	PMID[458643]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	20.3	uM	PMID[458644]
NPT32	Organism	Mus musculus	Mus musculus	Activity	<	70.0	%	PMID[458645]

☑ 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 NPC37548 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	402
0.1-0.2	3705
0.2-0.3	17715
0.3-0.4	13477
0.4-0.5	3376
0.5-0.6	2161
0.6-0.7	1316
0.7-0.8	452
0.8-0.85	65
0.85-0.9	19
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC38736
0.972	High Similarity	NPC470507
0.9716	High Similarity	NPC187951
0.9712	High Similarity	NPC242556
0.9441	High Similarity	NPC124005
0.9315	High Similarity	NPC471458
0.9252	High Similarity	NPC285469
0.9167	High Similarity	NPC129042
0.9122	High Similarity	NPC184476
0.9073	High Similarity	NPC472587
0.9067	High Similarity	NPC473320
0.906	High Similarity	NPC299594
0.9026	High Similarity	NPC6982
0.9007	High Similarity	NPC16667
0.8968	High Similarity	NPC34508
0.8926	High Similarity	NPC207726
0.8854	High Similarity	NPC288785
0.8849	High Similarity	NPC22079
0.8824	High Similarity	NPC271734
0.875	High Similarity	NPC67056
0.8742	High Similarity	NPC270009
0.8742	High Similarity	NPC141353
0.8725	High Similarity	NPC24678
0.8725	High Similarity	NPC105818
0.8718	High Similarity	NPC280548
0.8634	High Similarity	NPC192270
0.859	High Similarity	NPC49954
0.859	High Similarity	NPC474561
0.8581	High Similarity	NPC314372
0.8581	High Similarity	NPC159856
0.8562	High Similarity	NPC293472
0.8562	High Similarity	NPC2949
0.8526	High Similarity	NPC470508
0.8516	High Similarity	NPC282231
0.8509	High Similarity	NPC472443
0.8452	Intermediate Similarity	NPC279918
0.8446	Intermediate Similarity	NPC190296
0.8428	Intermediate Similarity	NPC470498
0.8418	Intermediate Similarity	NPC63751
0.8414	Intermediate Similarity	NPC325252
0.8392	Intermediate Similarity	NPC475450
0.8387	Intermediate Similarity	NPC92796
0.8387	Intermediate Similarity	NPC135141
0.8378	Intermediate Similarity	NPC63157
0.8378	Intermediate Similarity	NPC473868
0.8366	Intermediate Similarity	NPC25008
0.8366	Intermediate Similarity	NPC469763
0.8366	Intermediate Similarity	NPC259644
0.8366	Intermediate Similarity	NPC469760
0.8366	Intermediate Similarity	NPC73952
0.8366	Intermediate Similarity	NPC469765
0.8366	Intermediate Similarity	NPC469786
0.8354	Intermediate Similarity	NPC472444
0.8345	Intermediate Similarity	NPC198988
0.8344	Intermediate Similarity	NPC194640
0.8323	Intermediate Similarity	NPC46413
0.8312	Intermediate Similarity	NPC211572
0.8312	Intermediate Similarity	NPC80597
0.8312	Intermediate Similarity	NPC212376
0.8312	Intermediate Similarity	NPC70922
0.8312	Intermediate Similarity	NPC75540
0.8311	Intermediate Similarity	NPC59084
0.8298	Intermediate Similarity	NPC250361
0.8288	Intermediate Similarity	NPC218268
0.8282	Intermediate Similarity	NPC215795
0.8282	Intermediate Similarity	NPC176199
0.8273	Intermediate Similarity	NPC41174
0.8252	Intermediate Similarity	NPC473587
0.825	Intermediate Similarity	NPC194411
0.8243	Intermediate Similarity	NPC88097
0.8239	Intermediate Similarity	NPC54988
0.8239	Intermediate Similarity	NPC160105
0.8235	Intermediate Similarity	NPC33421
0.8221	Intermediate Similarity	NPC68354
0.8212	Intermediate Similarity	NPC470440
0.821	Intermediate Similarity	NPC472586
0.8205	Intermediate Similarity	NPC469762
0.8194	Intermediate Similarity	NPC475428
0.8188	Intermediate Similarity	NPC469779
0.8188	Intermediate Similarity	NPC469780
0.8188	Intermediate Similarity	NPC469784
0.8188	Intermediate Similarity	NPC469761
0.8188	Intermediate Similarity	NPC469783
0.8188	Intermediate Similarity	NPC469768
0.8188	Intermediate Similarity	NPC469767
0.8182	Intermediate Similarity	NPC473762
0.8141	Intermediate Similarity	NPC469785
0.8138	Intermediate Similarity	NPC179365
0.8133	Intermediate Similarity	NPC469766
0.8125	Intermediate Similarity	NPC109447
0.8121	Intermediate Similarity	NPC91179
0.8121	Intermediate Similarity	NPC73767
0.8113	Intermediate Similarity	NPC311276
0.811	Intermediate Similarity	NPC248454
0.811	Intermediate Similarity	NPC59269
0.8108	Intermediate Similarity	NPC125746
0.8108	Intermediate Similarity	NPC84911
0.8105	Intermediate Similarity	NPC21605
0.8105	Intermediate Similarity	NPC471957
0.8101	Intermediate Similarity	NPC131718
0.8098	Intermediate Similarity	NPC275305
0.8098	Intermediate Similarity	NPC37423
0.8082	Intermediate Similarity	NPC473930
0.8075	Intermediate Similarity	NPC201700
0.8067	Intermediate Similarity	NPC115611
0.8061	Intermediate Similarity	NPC11126
0.8052	Intermediate Similarity	NPC2272
0.8041	Intermediate Similarity	NPC96102
0.8041	Intermediate Similarity	NPC261195
0.8041	Intermediate Similarity	NPC29886
0.8037	Intermediate Similarity	NPC314603
0.8012	Intermediate Similarity	NPC470509
0.8012	Intermediate Similarity	NPC49217
0.8	Intermediate Similarity	NPC40779
0.8	Intermediate Similarity	NPC110126
0.8	Intermediate Similarity	NPC476118
0.8	Intermediate Similarity	NPC104483
0.7987	Intermediate Similarity	NPC477134
0.7987	Intermediate Similarity	NPC105127
0.7976	Intermediate Similarity	NPC228835
0.7974	Intermediate Similarity	NPC204141
0.7963	Intermediate Similarity	NPC317430
0.7961	Intermediate Similarity	NPC20144
0.7952	Intermediate Similarity	NPC72980
0.7927	Intermediate Similarity	NPC472123
0.7925	Intermediate Similarity	NPC206819
0.7925	Intermediate Similarity	NPC475990
0.7925	Intermediate Similarity	NPC318065
0.7925	Intermediate Similarity	NPC41257
0.7922	Intermediate Similarity	NPC143872
0.7917	Intermediate Similarity	NPC163055
0.7904	Intermediate Similarity	NPC198339
0.7898	Intermediate Similarity	NPC32200
0.7888	Intermediate Similarity	NPC102423
0.7888	Intermediate Similarity	NPC271797
0.7888	Intermediate Similarity	NPC21174
0.7886	Intermediate Similarity	NPC232130
0.7885	Intermediate Similarity	NPC148592
0.7885	Intermediate Similarity	NPC53947
0.7879	Intermediate Similarity	NPC329688
0.7879	Intermediate Similarity	NPC189812
0.7862	Intermediate Similarity	NPC286427
0.7861	Intermediate Similarity	NPC304187
0.7861	Intermediate Similarity	NPC477166
0.7853	Intermediate Similarity	NPC154293
0.7844	Intermediate Similarity	NPC213468
0.7834	Intermediate Similarity	NPC216713
0.7829	Intermediate Similarity	NPC279081
0.7824	Intermediate Similarity	NPC476319
0.7818	Intermediate Similarity	NPC313791
0.7811	Intermediate Similarity	NPC19679
0.7806	Intermediate Similarity	NPC288838
0.7785	Intermediate Similarity	NPC200214
0.7784	Intermediate Similarity	NPC151939
0.777	Intermediate Similarity	NPC82295
0.7765	Intermediate Similarity	NPC472294
0.7763	Intermediate Similarity	NPC312092
0.7758	Intermediate Similarity	NPC158129
0.7756	Intermediate Similarity	NPC179787
0.7756	Intermediate Similarity	NPC201380
0.7751	Intermediate Similarity	NPC233936
0.7738	Intermediate Similarity	NPC219336
0.7733	Intermediate Similarity	NPC17059
0.7733	Intermediate Similarity	NPC317030
0.7725	Intermediate Similarity	NPC267885
0.7719	Intermediate Similarity	NPC15102
0.7719	Intermediate Similarity	NPC280290
0.7712	Intermediate Similarity	NPC230002
0.7711	Intermediate Similarity	NPC97525
0.7711	Intermediate Similarity	NPC161861
0.7711	Intermediate Similarity	NPC64055
0.7707	Intermediate Similarity	NPC321911
0.7706	Intermediate Similarity	NPC472108
0.7706	Intermediate Similarity	NPC139291
0.7702	Intermediate Similarity	NPC230869
0.7702	Intermediate Similarity	NPC221786
0.7702	Intermediate Similarity	NPC56765
0.7702	Intermediate Similarity	NPC474880
0.7692	Intermediate Similarity	NPC300688
0.7692	Intermediate Similarity	NPC63545
0.7679	Intermediate Similarity	NPC15573
0.7679	Intermediate Similarity	NPC217372
0.7679	Intermediate Similarity	NPC183662
0.7674	Intermediate Similarity	NPC94752
0.767	Intermediate Similarity	NPC133366
0.7669	Intermediate Similarity	NPC8104
0.7665	Intermediate Similarity	NPC203468
0.7665	Intermediate Similarity	NPC149155
0.7665	Intermediate Similarity	NPC110500
0.7661	Intermediate Similarity	NPC165495
0.766	Intermediate Similarity	NPC81561
0.7654	Intermediate Similarity	NPC229173
0.7643	Intermediate Similarity	NPC469811
0.764	Intermediate Similarity	NPC129721
0.7633	Intermediate Similarity	NPC126709
0.7633	Intermediate Similarity	NPC248041
0.763	Intermediate Similarity	NPC204565
0.7614	Intermediate Similarity	NPC474177
0.761	Intermediate Similarity	NPC470233
0.7602	Intermediate Similarity	NPC48938

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 NPC37548 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	590
0.2-0.3	979
0.3-0.4	1470
0.4-0.5	2715
0.5-0.6	2300
0.6-0.7	729
0.7-0.8	128
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.898	High Similarity	NPD4462	Approved
0.898	High Similarity	NPD4463	Approved
0.8408	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1592	Phase 3
0.825	Intermediate Similarity	NPD1325	Approved
0.825	Intermediate Similarity	NPD1326	Approved
0.8243	Intermediate Similarity	NPD786	Approved
0.8221	Intermediate Similarity	NPD3505	Approved
0.8221	Intermediate Similarity	NPD3506	Approved
0.8171	Intermediate Similarity	NPD4076	Approved
0.8171	Intermediate Similarity	NPD4079	Approved
0.817	Intermediate Similarity	NPD3100	Discontinued
0.8146	Intermediate Similarity	NPD5254	Discontinued
0.8137	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5065	Approved
0.8052	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1722	Approved
0.8	Intermediate Similarity	NPD3833	Phase 3
0.8	Intermediate Similarity	NPD5138	Approved
0.8	Intermediate Similarity	NPD2172	Phase 1
0.8	Intermediate Similarity	NPD5140	Approved
0.8	Intermediate Similarity	NPD3835	Phase 3
0.7961	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD8386	Phase 2
0.7904	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6595	Phase 3
0.7879	Intermediate Similarity	NPD4128	Approved
0.7877	Intermediate Similarity	NPD3654	Approved
0.7867	Intermediate Similarity	NPD1262	Discovery
0.7853	Intermediate Similarity	NPD5021	Discontinued
0.7834	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6158	Phase 2
0.7785	Intermediate Similarity	NPD3385	Approved
0.7784	Intermediate Similarity	NPD2144	Approved
0.7784	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5020	Approved
0.7744	Intermediate Similarity	NPD4640	Approved
0.7744	Intermediate Similarity	NPD4639	Approved
0.7744	Intermediate Similarity	NPD4638	Approved
0.7733	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3961	Discontinued
0.773	Intermediate Similarity	NPD2915	Discontinued
0.7725	Intermediate Similarity	NPD4075	Phase 2
0.7706	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1683	Approved
0.7673	Intermediate Similarity	NPD2837	Discontinued
0.7665	Intermediate Similarity	NPD482	Approved
0.7662	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3038	Discontinued
0.764	Intermediate Similarity	NPD4326	Phase 2
0.7636	Intermediate Similarity	NPD2844	Phase 3
0.763	Intermediate Similarity	NPD8431	Approved
0.7619	Intermediate Similarity	NPD5104	Approved
0.7619	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2882	Phase 1
0.7607	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD2095	Phase 2
0.7602	Intermediate Similarity	NPD2092	Phase 2
0.7602	Intermediate Similarity	NPD5596	Phase 2
0.7602	Intermediate Similarity	NPD2094	Phase 2
0.7593	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4181	Approved
0.7571	Intermediate Similarity	NPD7619	Phase 3
0.7571	Intermediate Similarity	NPD7618	Phase 3
0.7561	Intermediate Similarity	NPD3323	Discontinued
0.7558	Intermediate Similarity	NPD2096	Phase 2
0.7558	Intermediate Similarity	NPD2091	Phase 2
0.7546	Intermediate Similarity	NPD1404	Approved
0.7546	Intermediate Similarity	NPD1403	Approved
0.7543	Intermediate Similarity	NPD4499	Approved
0.7532	Intermediate Similarity	NPD4703	Approved
0.7532	Intermediate Similarity	NPD4702	Approved
0.7531	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2641	Approved
0.753	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2640	Approved
0.7529	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2381	Approved
0.7515	Intermediate Similarity	NPD2380	Approved
0.7515	Intermediate Similarity	NPD2382	Approved
0.7514	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4047	Discontinued
0.7486	Intermediate Similarity	NPD7948	Phase 1
0.747	Intermediate Similarity	NPD2639	Approved
0.747	Intermediate Similarity	NPD2642	Approved
0.7468	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6492	Phase 2
0.7396	Intermediate Similarity	NPD750	Phase 2
0.7386	Intermediate Similarity	NPD4880	Discontinued
0.7371	Intermediate Similarity	NPD6217	Discontinued
0.7362	Intermediate Similarity	NPD2150	Discontinued
0.7358	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3609	Approved
0.7337	Intermediate Similarity	NPD3610	Approved
0.7333	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD4511	Phase 1
0.7314	Intermediate Similarity	NPD5075	Discontinued
0.7308	Intermediate Similarity	NPD6248	Phase 2
0.7308	Intermediate Similarity	NPD6249	Phase 2
0.729	Intermediate Similarity	NPD45	Approved
0.729	Intermediate Similarity	NPD6554	Approved
0.7289	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD947	Approved
0.7283	Intermediate Similarity	NPD5898	Approved
0.7283	Intermediate Similarity	NPD5899	Approved
0.7283	Intermediate Similarity	NPD5897	Approved
0.7283	Intermediate Similarity	NPD5473	Discontinued
0.7278	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6159	Phase 2
0.7257	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2580	Discontinued
0.725	Intermediate Similarity	NPD7469	Discontinued
0.7241	Intermediate Similarity	NPD4399	Phase 2
0.7237	Intermediate Similarity	NPD3476	Approved
0.7237	Intermediate Similarity	NPD3475	Approved
0.7235	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6828	Phase 2
0.7232	Intermediate Similarity	NPD2383	Phase 1
0.7226	Intermediate Similarity	NPD1253	Approved
0.7226	Intermediate Similarity	NPD1254	Approved
0.7226	Intermediate Similarity	NPD1256	Approved
0.7226	Intermediate Similarity	NPD1255	Approved
0.7219	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3814	Phase 1
0.7207	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1661	Suspended
0.7205	Intermediate Similarity	NPD4547	Phase 3
0.7204	Intermediate Similarity	NPD5901	Discontinued
0.7202	Intermediate Similarity	NPD2720	Phase 1
0.7202	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3320	Approved
0.72	Intermediate Similarity	NPD3318	Approved
0.72	Intermediate Similarity	NPD5105	Approved
0.72	Intermediate Similarity	NPD5106	Approved
0.72	Intermediate Similarity	NPD3319	Phase 1
0.7184	Intermediate Similarity	NPD6452	Discontinued
0.7181	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2006	Phase 2
0.7169	Intermediate Similarity	NPD5255	Approved
0.7167	Intermediate Similarity	NPD4615	Phase 2
0.716	Intermediate Similarity	NPD2430	Phase 2
0.7152	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD991	Phase 2
0.7152	Intermediate Similarity	NPD2118	Approved
0.7152	Intermediate Similarity	NPD2119	Approved
0.7135	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3116	Approved
0.7135	Intermediate Similarity	NPD3117	Approved
0.7134	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1038	Approved
0.712	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5913	Phase 3
0.7111	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5100	Phase 3
0.7104	Intermediate Similarity	NPD5003	Discontinued
0.7104	Intermediate Similarity	NPD6664	Approved
0.7097	Intermediate Similarity	NPD8073	Approved
0.7095	Intermediate Similarity	NPD4334	Discontinued
0.7091	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD680	Discontinued
0.7086	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2480	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4601	Approved
0.7081	Intermediate Similarity	NPD484	Approved
0.7081	Intermediate Similarity	NPD4600	Approved
0.7079	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1251	Discontinued
0.7074	Intermediate Similarity	NPD3003	Approved
0.7074	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3404	Approved
0.7069	Intermediate Similarity	NPD4398	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3717	Discontinued
0.7059	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5487	Phase 1
0.7059	Intermediate Similarity	NPD8072	Approved
0.7045	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD802	Phase 2
0.7031	Intermediate Similarity	NPD8093	Discontinued
0.7027	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3813	Approved
0.7019	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3785	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