NPASS Compound

Structure

CID72647 OpenBabel06191715412D 45 48 0 0 1 0 0 0 0 0999 V2000 -6.7797 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8942 6.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1169 -2.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9342 4.6369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2855 1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3655 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7914 3.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9342 -0.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9483 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3742 5.4683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7914 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9600 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8984 1.3661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4142 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8984 2.9194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4800 0.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1286 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1169 -1.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8942 4.6369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4542 1.4400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5342 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9600 2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3342 2.1428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 -0.9600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3742 2.1428 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7914 1.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8114 1.6628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2855 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3742 3.8055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4542 0.4800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9600 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7914 0.4800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5342 2.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1286 3.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5881 1.0985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2855 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3342 3.8055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8114 2.6228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7028 0.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9600 1.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4542 -1.4400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8942 2.9742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 9 19 1 0 0 0 0 10 20 2 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 33 1 0 0 0 0 13 21 1 0 0 0 0 13 27 1 0 0 0 0 14 24 2 0 0 0 0 14 28 1 0 0 0 0 15 32 1 0 0 0 0 16 24 1 0 0 0 0 16 40 1 0 0 0 0 17 33 1 0 0 0 0 17 42 1 0 0 0 0 18 41 1 0 0 0 0 19 3 1 1 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 6 0 0 0 22 35 2 0 0 0 0 22 41 1 0 0 0 0 23 36 2 0 0 0 0 23 43 1 0 0 0 0 24 26 1 0 0 0 0 25 29 1 0 0 0 0 25 44 1 1 0 0 0 26 15 1 1 0 0 0 26 45 1 0 0 0 0 27 34 1 6 0 0 0 27 43 1 0 0 0 0 28 37 2 0 0 0 0 28 40 1 0 0 0 0 29 32 1 6 0 0 0 29 34 1 0 0 0 0 30 38 2 0 0 0 0 30 44 1 0 0 0 0 31 39 2 0 0 0 0 31 45 1 0 0 0 0 32 8 1 6 0 0 0 33 34 1 6 0 0 0 33 42 1 0 0 0 0 34 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.32
Volume:	640.631
LogP:	4.099
LogD:	3.089
LogS:	-4.133
# Rotatable Bonds:	15
TPSA:	151.1
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.141
Synthetic Accessibility Score:	5.972
Fsp3:	0.706
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.232
MDCK Permeability:	4.737799463327974e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.733
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.65
30% Bioavailability (F30%):	0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	91.14069366455078%
Volume Distribution (VD):	1.566
Pgp-substrate:	5.257824897766113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.397
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.922
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.089
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.782
CYP3A4-substrate:	0.665

ADMET: Excretion

Clearance (CL):	5.549
Half-life (T1/2):	0.6

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.913
Drug-inuced Liver Injury (DILI):	0.835
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.772
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.209
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.801

Download Data

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

Natural Product: NPC72647

Natural Product ID:	NPC72647
*Common Name:**	Ajugamarin H1
IUPAC Name:	[(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-7,8-dimethyl-8-[(2S)-2-[(E)-2-methylbut-2-enoyl]oxy-2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (2S)-2-methylbutanoate
Synonyms:	Ajugamarin H1
Standard InCHIKey:	YUTIPMUBYJJHKA-LZLNCZMXSA-N
Standard InCHI:	InChI=1S/C34H48O11/c1-9-19(3)30(38)44-25-11-12-33(17-42-33)34(18-41-22(6)35)27(43-23(7)36)13-21(5)32(8,29(25)34)15-26(24-14-28(37)40-16-24)45-31(39)20(4)10-2/h10,14,19,21,25-27,29H,9,11-13,15-18H2,1-8H3/b20-10+/t19-,21+,25+,26-,27-,29+,32-,33-,34+/m0/s1
SMILES:	CC[C@H](C)C(=O)O[C@@H]1CC[C@]2(CO2)[C@]2(COC(=O)C)[C@H](C[C@@H](C)[C@](C)(C[C@@H](C3=CC(=O)OC3)OC(=O)/C(=C/C)/C)[C@@H]12)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813863
PubChem CID:	21629954
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21682262]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	whole plants	Zhejiang Province, China	2008-AUG	PMID[21682262]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9680	Ajuga ciliata	Species	Lamiaceae	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
Others	10

Activity Type	# Activity
Cell Line	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	67.3	%	PMID[565747]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	70.4	%	PMID[565747]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	87.5	%	PMID[565747]
NPT1193	Organism	Athalia rosae ruficornis	Athalia rosae ruficornis	Activity	<	10.0	%	PMID[565748]
NPT1193	Organism	Athalia rosae ruficornis	Athalia rosae ruficornis	Activity	=	7.0	%	PMID[565749]
NPT1193	Organism	Athalia rosae ruficornis	Athalia rosae ruficornis	Activity	=	0.0	%	PMID[565749]

☑ 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 NPC72647 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	242
0.1-0.2	1465
0.2-0.3	4942
0.3-0.4	9907
0.4-0.5	12256
0.5-0.6	7164
0.6-0.7	5402
0.7-0.8	1244
0.8-0.85	49
0.85-0.9	13
0.9-0.95	5
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC107806
0.989	High Similarity	NPC100912
0.989	High Similarity	NPC475446
0.989	High Similarity	NPC311241
0.978	High Similarity	NPC209297
0.978	High Similarity	NPC475380
0.956	High Similarity	NPC140277
0.9355	High Similarity	NPC194132
0.9271	High Similarity	NPC475038
0.9271	High Similarity	NPC109195
0.9011	High Similarity	NPC93411
0.8936	High Similarity	NPC161998
0.883	High Similarity	NPC7349
0.8737	High Similarity	NPC105490
0.8687	High Similarity	NPC162973
0.8673	High Similarity	NPC16601
0.8586	High Similarity	NPC11974
0.8529	High Similarity	NPC216636
0.8529	High Similarity	NPC319438
0.8485	Intermediate Similarity	NPC471413
0.8454	Intermediate Similarity	NPC276110
0.8454	Intermediate Similarity	NPC476519
0.8447	Intermediate Similarity	NPC181994
0.8416	Intermediate Similarity	NPC471938
0.8404	Intermediate Similarity	NPC106332
0.84	Intermediate Similarity	NPC471412
0.8365	Intermediate Similarity	NPC322912
0.8333	Intermediate Similarity	NPC471937
0.8317	Intermediate Similarity	NPC471914
0.8317	Intermediate Similarity	NPC476081
0.8317	Intermediate Similarity	NPC472552
0.83	Intermediate Similarity	NPC324841
0.828	Intermediate Similarity	NPC474013
0.8252	Intermediate Similarity	NPC51719
0.8218	Intermediate Similarity	NPC472554
0.8211	Intermediate Similarity	NPC69713
0.82	Intermediate Similarity	NPC278673
0.8182	Intermediate Similarity	NPC260796
0.8182	Intermediate Similarity	NPC29952
0.8182	Intermediate Similarity	NPC234993
0.8182	Intermediate Similarity	NPC134072
0.8173	Intermediate Similarity	NPC471205
0.8144	Intermediate Similarity	NPC473944
0.8132	Intermediate Similarity	NPC469802
0.8119	Intermediate Similarity	NPC473545
0.8119	Intermediate Similarity	NPC472187
0.8119	Intermediate Similarity	NPC38855
0.8113	Intermediate Similarity	NPC253906
0.8105	Intermediate Similarity	NPC475087
0.8105	Intermediate Similarity	NPC102640
0.81	Intermediate Similarity	NPC51499
0.81	Intermediate Similarity	NPC474921
0.8081	Intermediate Similarity	NPC111273
0.8081	Intermediate Similarity	NPC471915
0.8077	Intermediate Similarity	NPC218158
0.8077	Intermediate Similarity	NPC34768
0.8077	Intermediate Similarity	NPC471206
0.8073	Intermediate Similarity	NPC470793
0.8061	Intermediate Similarity	NPC139692
0.8058	Intermediate Similarity	NPC180204
0.8058	Intermediate Similarity	NPC120009
0.8058	Intermediate Similarity	NPC165608
0.8058	Intermediate Similarity	NPC160583
0.8058	Intermediate Similarity	NPC254202
0.8058	Intermediate Similarity	NPC120321
0.8041	Intermediate Similarity	NPC78973
0.802	Intermediate Similarity	NPC472186
0.802	Intermediate Similarity	NPC471366
0.802	Intermediate Similarity	NPC325229
0.802	Intermediate Similarity	NPC318917
0.802	Intermediate Similarity	NPC275086
0.802	Intermediate Similarity	NPC476800
0.8019	Intermediate Similarity	NPC475586
0.8	Intermediate Similarity	NPC180744
0.8	Intermediate Similarity	NPC67321
0.8	Intermediate Similarity	NPC302788
0.8	Intermediate Similarity	NPC131813
0.8	Intermediate Similarity	NPC187435
0.8	Intermediate Similarity	NPC102996
0.8	Intermediate Similarity	NPC122816
0.7982	Intermediate Similarity	NPC90472
0.7981	Intermediate Similarity	NPC477127
0.798	Intermediate Similarity	NPC57117
0.7979	Intermediate Similarity	NPC306951
0.7979	Intermediate Similarity	NPC96055
0.7979	Intermediate Similarity	NPC32223
0.7963	Intermediate Similarity	NPC470063
0.7959	Intermediate Similarity	NPC78594
0.7959	Intermediate Similarity	NPC72845
0.7957	Intermediate Similarity	NPC471218
0.7941	Intermediate Similarity	NPC47024
0.7941	Intermediate Similarity	NPC473204
0.7941	Intermediate Similarity	NPC251680
0.7938	Intermediate Similarity	NPC170633
0.7928	Intermediate Similarity	NPC470420
0.7925	Intermediate Similarity	NPC88701
0.7925	Intermediate Similarity	NPC475263
0.7921	Intermediate Similarity	NPC84335
0.7921	Intermediate Similarity	NPC110937
0.7921	Intermediate Similarity	NPC38530
0.7921	Intermediate Similarity	NPC472188
0.7917	Intermediate Similarity	NPC264546
0.7917	Intermediate Similarity	NPC166857
0.7909	Intermediate Similarity	NPC471816
0.7905	Intermediate Similarity	NPC220217
0.7905	Intermediate Similarity	NPC477090
0.7905	Intermediate Similarity	NPC119855
0.79	Intermediate Similarity	NPC472441
0.79	Intermediate Similarity	NPC56369
0.789	Intermediate Similarity	NPC474937
0.789	Intermediate Similarity	NPC477126
0.789	Intermediate Similarity	NPC159333
0.7885	Intermediate Similarity	NPC10232
0.7885	Intermediate Similarity	NPC112009
0.7885	Intermediate Similarity	NPC97487
0.7885	Intermediate Similarity	NPC45897
0.7885	Intermediate Similarity	NPC189588
0.7885	Intermediate Similarity	NPC23584
0.7885	Intermediate Similarity	NPC473523
0.7885	Intermediate Similarity	NPC196471
0.7885	Intermediate Similarity	NPC474822
0.7885	Intermediate Similarity	NPC281378
0.7885	Intermediate Similarity	NPC187302
0.7879	Intermediate Similarity	NPC110022
0.7879	Intermediate Similarity	NPC205034
0.7879	Intermediate Similarity	NPC472640
0.7879	Intermediate Similarity	NPC475657
0.7879	Intermediate Similarity	NPC162615
0.7879	Intermediate Similarity	NPC152778
0.7879	Intermediate Similarity	NPC472641
0.7876	Intermediate Similarity	NPC204731
0.787	Intermediate Similarity	NPC470076
0.7864	Intermediate Similarity	NPC25177
0.7864	Intermediate Similarity	NPC268829
0.7864	Intermediate Similarity	NPC295110
0.7864	Intermediate Similarity	NPC247701
0.7864	Intermediate Similarity	NPC222875
0.7857	Intermediate Similarity	NPC475776
0.7857	Intermediate Similarity	NPC302280
0.785	Intermediate Similarity	NPC469370
0.785	Intermediate Similarity	NPC299590
0.7843	Intermediate Similarity	NPC218107
0.7843	Intermediate Similarity	NPC264378
0.783	Intermediate Similarity	NPC473586
0.783	Intermediate Similarity	NPC179380
0.783	Intermediate Similarity	NPC475074
0.783	Intermediate Similarity	NPC109376
0.783	Intermediate Similarity	NPC471601
0.7822	Intermediate Similarity	NPC242848
0.7822	Intermediate Similarity	NPC472997
0.7822	Intermediate Similarity	NPC16967
0.7822	Intermediate Similarity	NPC165632
0.7822	Intermediate Similarity	NPC171598
0.7822	Intermediate Similarity	NPC472996
0.7822	Intermediate Similarity	NPC473964
0.7818	Intermediate Similarity	NPC43213
0.7812	Intermediate Similarity	NPC471219
0.781	Intermediate Similarity	NPC473543
0.7802	Intermediate Similarity	NPC189206
0.78	Intermediate Similarity	NPC477722
0.78	Intermediate Similarity	NPC38830
0.7798	Intermediate Similarity	NPC17138
0.7798	Intermediate Similarity	NPC170212
0.7798	Intermediate Similarity	NPC221511
0.7798	Intermediate Similarity	NPC151216
0.7798	Intermediate Similarity	NPC475391
0.7798	Intermediate Similarity	NPC215643
0.7798	Intermediate Similarity	NPC89227
0.7798	Intermediate Similarity	NPC101825
0.7798	Intermediate Similarity	NPC265499
0.7788	Intermediate Similarity	NPC475344
0.7788	Intermediate Similarity	NPC41123
0.7788	Intermediate Similarity	NPC114939
0.7788	Intermediate Similarity	NPC145074
0.7788	Intermediate Similarity	NPC4548
0.7788	Intermediate Similarity	NPC165250
0.7788	Intermediate Similarity	NPC11956
0.7788	Intermediate Similarity	NPC476471
0.7778	Intermediate Similarity	NPC472215
0.7778	Intermediate Similarity	NPC177047
0.7778	Intermediate Similarity	NPC49420
0.7778	Intermediate Similarity	NPC472214
0.7778	Intermediate Similarity	NPC329842
0.7778	Intermediate Similarity	NPC473675
0.7767	Intermediate Similarity	NPC470761
0.7767	Intermediate Similarity	NPC271295
0.7767	Intermediate Similarity	NPC473219
0.7767	Intermediate Similarity	NPC470074
0.7766	Intermediate Similarity	NPC200513
0.7757	Intermediate Similarity	NPC275539
0.7757	Intermediate Similarity	NPC38948
0.7757	Intermediate Similarity	NPC473939
0.7757	Intermediate Similarity	NPC94377
0.7757	Intermediate Similarity	NPC306265
0.7757	Intermediate Similarity	NPC224660
0.7757	Intermediate Similarity	NPC470024
0.7757	Intermediate Similarity	NPC189075
0.7757	Intermediate Similarity	NPC50124
0.7757	Intermediate Similarity	NPC473595
0.7757	Intermediate Similarity	NPC102843

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 NPC72647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1707
0.2-0.3	4034
0.3-0.4	2154
0.4-0.5	662
0.5-0.6	220
0.6-0.7	148
0.7-0.8	14
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8173	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD7638	Approved
0.7944	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7640	Approved
0.7941	Intermediate Similarity	NPD7639	Approved
0.785	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6648	Approved
0.7593	Intermediate Similarity	NPD6686	Approved
0.7524	Intermediate Similarity	NPD5344	Discontinued
0.75	Intermediate Similarity	NPD4225	Approved
0.7456	Intermediate Similarity	NPD7328	Approved
0.7456	Intermediate Similarity	NPD7327	Approved
0.7407	Intermediate Similarity	NPD6008	Approved
0.7391	Intermediate Similarity	NPD7516	Approved
0.7328	Intermediate Similarity	NPD8377	Approved
0.7328	Intermediate Similarity	NPD8294	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7282	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7900	Approved
0.7265	Intermediate Similarity	NPD8380	Approved
0.7265	Intermediate Similarity	NPD8335	Approved
0.7265	Intermediate Similarity	NPD8379	Approved
0.7265	Intermediate Similarity	NPD8296	Approved
0.7265	Intermediate Similarity	NPD8033	Approved
0.7265	Intermediate Similarity	NPD8378	Approved
0.7217	Intermediate Similarity	NPD7115	Discovery
0.7172	Intermediate Similarity	NPD1694	Approved
0.7167	Intermediate Similarity	NPD7507	Approved
0.7157	Intermediate Similarity	NPD7838	Discovery
0.7115	Intermediate Similarity	NPD7748	Approved
0.7075	Intermediate Similarity	NPD7902	Approved
0.7059	Intermediate Similarity	NPD6051	Approved
0.7018	Intermediate Similarity	NPD8297	Approved
0.6992	Remote Similarity	NPD7319	Approved
0.699	Remote Similarity	NPD6698	Approved
0.699	Remote Similarity	NPD46	Approved
0.6975	Remote Similarity	NPD7503	Approved
0.6964	Remote Similarity	NPD6899	Approved
0.6964	Remote Similarity	NPD6881	Approved
0.6937	Remote Similarity	NPD6675	Approved
0.6937	Remote Similarity	NPD7128	Approved
0.6937	Remote Similarity	NPD5739	Approved
0.6937	Remote Similarity	NPD6402	Approved
0.6931	Remote Similarity	NPD7521	Approved
0.6931	Remote Similarity	NPD6684	Approved
0.6931	Remote Similarity	NPD6409	Approved
0.6931	Remote Similarity	NPD7334	Approved
0.6931	Remote Similarity	NPD7146	Approved
0.6931	Remote Similarity	NPD5330	Approved
0.693	Remote Similarity	NPD6650	Approved
0.693	Remote Similarity	NPD6649	Approved
0.693	Remote Similarity	NPD8130	Phase 1
0.6903	Remote Similarity	NPD6372	Approved
0.6903	Remote Similarity	NPD6373	Approved
0.6887	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5697	Approved
0.687	Remote Similarity	NPD6882	Approved
0.6863	Remote Similarity	NPD3573	Approved
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6814	Remote Similarity	NPD7320	Approved
0.6796	Remote Similarity	NPD6903	Approved
0.6796	Remote Similarity	NPD5737	Approved
0.6796	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6672	Approved
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.6762	Remote Similarity	NPD5693	Phase 1
0.6762	Remote Similarity	NPD7515	Phase 2
0.6754	Remote Similarity	NPD6014	Approved
0.6754	Remote Similarity	NPD6013	Approved
0.6754	Remote Similarity	NPD6012	Approved
0.675	Remote Similarity	NPD6319	Approved
0.6731	Remote Similarity	NPD1695	Approved
0.6726	Remote Similarity	NPD5701	Approved
0.6698	Remote Similarity	NPD6399	Phase 3
0.6697	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4632	Approved
0.6606	Remote Similarity	NPD6084	Phase 2
0.6606	Remote Similarity	NPD6083	Phase 2
0.6604	Remote Similarity	NPD8035	Phase 2
0.6604	Remote Similarity	NPD7637	Suspended
0.6604	Remote Similarity	NPD8034	Phase 2
0.6593	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7604	Phase 2
0.6581	Remote Similarity	NPD6053	Discontinued
0.6579	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6080	Approved
0.6571	Remote Similarity	NPD6904	Approved
0.6571	Remote Similarity	NPD6673	Approved
0.6552	Remote Similarity	NPD6371	Approved
0.6535	Remote Similarity	NPD5209	Approved
0.6532	Remote Similarity	NPD7492	Approved
0.6518	Remote Similarity	NPD5211	Phase 2
0.6508	Remote Similarity	NPD7736	Approved
0.6505	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD7525	Registered
0.6496	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4696	Approved
0.6486	Remote Similarity	NPD5286	Approved
0.6486	Remote Similarity	NPD5285	Approved
0.6481	Remote Similarity	NPD6001	Approved
0.648	Remote Similarity	NPD6616	Approved
0.6475	Remote Similarity	NPD6054	Approved
0.6466	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4755	Approved
0.6452	Remote Similarity	NPD8328	Phase 3
0.6449	Remote Similarity	NPD6079	Approved
0.6442	Remote Similarity	NPD3618	Phase 1
0.6435	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD7078	Approved
0.6429	Remote Similarity	NPD8293	Discontinued
0.6423	Remote Similarity	NPD5983	Phase 2
0.6422	Remote Similarity	NPD5695	Phase 3
0.6417	Remote Similarity	NPD6274	Approved
0.6415	Remote Similarity	NPD5328	Approved
0.6408	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5141	Approved
0.6396	Remote Similarity	NPD5696	Approved
0.6393	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7101	Approved
0.6389	Remote Similarity	NPD4202	Approved
0.6372	Remote Similarity	NPD4633	Approved
0.6372	Remote Similarity	NPD5225	Approved
0.6372	Remote Similarity	NPD5224	Approved
0.6372	Remote Similarity	NPD5226	Approved
0.6371	Remote Similarity	NPD6370	Approved
0.6349	Remote Similarity	NPD6336	Discontinued
0.6341	Remote Similarity	NPD6059	Approved
0.6339	Remote Similarity	NPD4700	Approved
0.6327	Remote Similarity	NPD8039	Approved
0.6321	Remote Similarity	NPD5208	Approved
0.6316	Remote Similarity	NPD5174	Approved
0.6316	Remote Similarity	NPD5175	Approved
0.6311	Remote Similarity	NPD6335	Approved
0.6311	Remote Similarity	NPD6695	Phase 3
0.6296	Remote Similarity	NPD6050	Approved
0.629	Remote Similarity	NPD6016	Approved
0.629	Remote Similarity	NPD6015	Approved
0.6286	Remote Similarity	NPD6098	Approved
0.6283	Remote Similarity	NPD5223	Approved
0.6271	Remote Similarity	NPD4634	Approved
0.624	Remote Similarity	NPD5988	Approved
0.6239	Remote Similarity	NPD4730	Approved
0.6239	Remote Similarity	NPD5779	Approved
0.6239	Remote Similarity	NPD5778	Approved
0.6239	Remote Similarity	NPD4729	Approved
0.6238	Remote Similarity	NPD7645	Phase 2
0.623	Remote Similarity	NPD6317	Approved
0.6226	Remote Similarity	NPD7750	Discontinued
0.6216	Remote Similarity	NPD5221	Approved
0.6216	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5222	Approved
0.6207	Remote Similarity	NPD4768	Approved
0.6207	Remote Similarity	NPD4767	Approved
0.6204	Remote Similarity	NPD5692	Phase 3
0.6204	Remote Similarity	NPD3168	Discontinued
0.619	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6313	Approved
0.6179	Remote Similarity	NPD6314	Approved
0.6161	Remote Similarity	NPD5173	Approved
0.616	Remote Similarity	NPD8515	Approved
0.616	Remote Similarity	NPD8516	Approved
0.616	Remote Similarity	NPD6921	Approved
0.616	Remote Similarity	NPD6908	Approved
0.616	Remote Similarity	NPD8517	Approved
0.616	Remote Similarity	NPD6909	Approved
0.616	Remote Similarity	NPD8513	Phase 3
0.6148	Remote Similarity	NPD6868	Approved
0.6147	Remote Similarity	NPD5694	Approved
0.6134	Remote Similarity	NPD5251	Approved
0.6134	Remote Similarity	NPD5247	Approved
0.6134	Remote Similarity	NPD5249	Phase 3
0.6134	Remote Similarity	NPD5248	Approved
0.6134	Remote Similarity	NPD5250	Approved
0.6132	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4753	Phase 2
0.6107	Remote Similarity	NPD7260	Phase 2
0.6102	Remote Similarity	NPD5128	Approved
0.6098	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD3665	Phase 1
0.6095	Remote Similarity	NPD4786	Approved
0.6095	Remote Similarity	NPD3666	Approved
0.6095	Remote Similarity	NPD3668	Phase 3
0.6095	Remote Similarity	NPD3133	Approved
0.6083	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7524	Approved
0.6071	Remote Similarity	NPD7732	Phase 3
0.6071	Remote Similarity	NPD4697	Phase 3
0.6058	Remote Similarity	NPD3667	Approved
0.6055	Remote Similarity	NPD5207	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data