NPASS Compound

Structure

CID323074 OpenBabel06191716172D 39 40 0 0 1 0 0 0 0 0999 V2000 0.5000 -5.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -8.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8660 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -3.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -6.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -6.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -6.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -6.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -7.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5000 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5000 -5.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0000 -6.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -6.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -7.4282 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0000 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5000 -5.6962 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0000 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -6.5622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0000 -4.8301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0000 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -5.6962 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 -0.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 3.5000 -3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -6.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -5.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -4.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -5.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -5.6962 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.9183 -4.1549 0.0000 Na 0 3 0 0 0 15 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 2 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 17 1 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 25 2 0 0 0 0 15 27 2 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 22 26 1 0 0 0 0 23 3 1 6 0 0 0 23 28 1 0 0 0 0 24 27 1 0 0 0 0 25 32 1 0 0 0 0 26 31 1 1 0 0 0 27 33 1 0 0 0 0 28 20 1 6 0 0 0 28 37 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 1 0 0 0 31 6 1 1 0 0 0 34 38 1 0 0 0 0 35 38 2 0 0 0 0 36 38 2 0 0 0 0 37 38 1 0 0 0 0 M CHG 2 32 -1 39 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	547.31
Volume:	575.812
LogP:	6.662
LogD:	5.402
LogS:	-5.092
# Rotatable Bonds:	11
TPSA:	106.89
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	4.776
Fsp3:	0.677
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:	-4.85
MDCK Permeability:	1.9750907085835934e-05
Pgp-inhibitor:	0.936
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.133

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.316
Plasma Protein Binding (PPB):	97.8929672241211%
Volume Distribution (VD):	0.636
Pgp-substrate:	0.6509003043174744%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.566
CYP2C9-inhibitor:	0.328
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.374
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.392
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	2.58
Half-life (T1/2):	0.042

ADMET: Toxicity

hERG Blockers:	0.337
Human Hepatotoxicity (H-HT):	0.718
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.207
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.916
Carcinogencity:	0.688
Eye Corrosion:	0.392
Eye Irritation:	0.913
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC323074

Natural Product ID:	NPC323074
*Common Name:**	Sodium (2R,3R)-9-(2,5-Dihydroxyphenyl)-3,7-Dimethyl-1-((1S,4As,8As)-5,5,8A-Trimethyl-2-Methylene-Decahydronaphthalen-1-Yl)Non-7-En-2-Yl Sulfate
IUPAC Name:	sodium;[(E,2R,3R)-1-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-9-(2,5-dihydroxyphenyl)-3,7-dimethylnon-7-en-2-yl] sulfate
Synonyms:
Standard InCHIKey:	KSPFWIJQADGODS-NHDYRKAGSA-M
Standard InCHI:	InChI=1S/C31H48O6S.Na/c1-21(11-13-24-19-25(32)14-15-27(24)33)9-7-10-23(3)28(37-38(34,35)36)20-26-22(2)12-16-29-30(4,5)17-8-18-31(26,29)6;/h11,14-15,19,23,26,28-29,32-33H,2,7-10,12-13,16-18,20H2,1,3-6H3,(H,34,35,36);/q;+1/p-1/b21-11+;/t23-,26+,28-,29+,31-;/m1./s1
SMILES:	CC(CCCC(=CCC1=C(C=CC(=C1)O)O)C)C(CC2C(=C)CCC3C2(CCCC3(C)C)C)OS(=O)(=O)[O-].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491665
PubChem CID:	44588853
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO30318	Coscinoderma	Genus	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21827183]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]

☑ 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	5
MIC	16
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Organism	17
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	71000.0	nM	PMID[529563]
NPT111	Cell Line	K562	Homo sapiens	LC50	>	200000.0	nM	PMID[529564]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	98000.0	nM	PMID[529564]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	45000.0	nM	PMID[529564]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	131200.0	nM	PMID[529563]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[529563]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1.56	ug.mL-1	PMID[529563]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[529563]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	6.25	ug.mL-1	PMID[529563]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	50.0	ug.mL-1	PMID[529563]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[529563]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	4000.0	nM	PMID[529564]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[529564]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1.56	ug.mL-1	PMID[529564]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[529564]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	50.0	ug.mL-1	PMID[529564]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	6.25	ug.mL-1	PMID[529564]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[529564]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[529564]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[529564]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[529564]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[529564]

☑ 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 NPC323074 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	298
0.1-0.2	1419
0.2-0.3	2986
0.3-0.4	8839
0.4-0.5	11366
0.5-0.6	12231
0.6-0.7	4832
0.7-0.8	657
0.8-0.85	54
0.85-0.9	7
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC477037
0.9735	High Similarity	NPC318581
0.9735	High Similarity	NPC325544
0.9107	High Similarity	NPC77772
0.9027	High Similarity	NPC177962
0.9027	High Similarity	NPC62867
0.8938	High Similarity	NPC266937
0.8938	High Similarity	NPC470770
0.8919	High Similarity	NPC320439
0.8879	High Similarity	NPC141001
0.8718	High Similarity	NPC92
0.8718	High Similarity	NPC469663
0.8718	High Similarity	NPC308828
0.8707	High Similarity	NPC471534
0.8696	High Similarity	NPC228425
0.8661	High Similarity	NPC155072
0.8632	High Similarity	NPC147179
0.8629	High Similarity	NPC476536
0.8583	High Similarity	NPC135467
0.8583	High Similarity	NPC260832
0.8571	High Similarity	NPC469609
0.8559	High Similarity	NPC308311
0.8559	High Similarity	NPC477137
0.8559	High Similarity	NPC219112
0.8559	High Similarity	NPC38893
0.8547	High Similarity	NPC268160
0.85	High Similarity	NPC469644
0.8487	Intermediate Similarity	NPC477136
0.8475	Intermediate Similarity	NPC35797
0.8475	Intermediate Similarity	NPC192948
0.8417	Intermediate Similarity	NPC471671
0.8407	Intermediate Similarity	NPC47284
0.8403	Intermediate Similarity	NPC474358
0.8403	Intermediate Similarity	NPC154511
0.8403	Intermediate Similarity	NPC247858
0.8403	Intermediate Similarity	NPC474387
0.8403	Intermediate Similarity	NPC257540
0.8403	Intermediate Similarity	NPC137496
0.8393	Intermediate Similarity	NPC269212
0.8378	Intermediate Similarity	NPC129373
0.8378	Intermediate Similarity	NPC248396
0.8378	Intermediate Similarity	NPC48730
0.8374	Intermediate Similarity	NPC478058
0.8362	Intermediate Similarity	NPC132720
0.8362	Intermediate Similarity	NPC141782
0.8362	Intermediate Similarity	NPC13482
0.8333	Intermediate Similarity	NPC53740
0.8333	Intermediate Similarity	NPC172219
0.8333	Intermediate Similarity	NPC304510
0.8319	Intermediate Similarity	NPC323810
0.8304	Intermediate Similarity	NPC12221
0.8291	Intermediate Similarity	NPC260323
0.8291	Intermediate Similarity	NPC176279
0.8288	Intermediate Similarity	NPC260775
0.8281	Intermediate Similarity	NPC472793
0.8264	Intermediate Similarity	NPC164649
0.8264	Intermediate Similarity	NPC48342
0.8261	Intermediate Similarity	NPC474352
0.825	Intermediate Similarity	NPC471668
0.8235	Intermediate Similarity	NPC195922
0.823	Intermediate Similarity	NPC108497
0.822	Intermediate Similarity	NPC302371
0.822	Intermediate Similarity	NPC250323
0.8217	Intermediate Similarity	NPC473047
0.8214	Intermediate Similarity	NPC70677
0.8214	Intermediate Similarity	NPC130756
0.8214	Intermediate Similarity	NPC12931
0.8211	Intermediate Similarity	NPC328504
0.8198	Intermediate Similarity	NPC152097
0.8197	Intermediate Similarity	NPC151197
0.819	Intermediate Similarity	NPC11554
0.8182	Intermediate Similarity	NPC320864
0.8174	Intermediate Similarity	NPC469913
0.8167	Intermediate Similarity	NPC469719
0.8158	Intermediate Similarity	NPC475225
0.8158	Intermediate Similarity	NPC475580
0.8142	Intermediate Similarity	NPC252105
0.8142	Intermediate Similarity	NPC477685
0.8136	Intermediate Similarity	NPC95716
0.8136	Intermediate Similarity	NPC469912
0.8136	Intermediate Similarity	NPC54373
0.8136	Intermediate Similarity	NPC322753
0.813	Intermediate Similarity	NPC68339
0.812	Intermediate Similarity	NPC473524
0.8115	Intermediate Similarity	NPC154030
0.8115	Intermediate Similarity	NPC206
0.8095	Intermediate Similarity	NPC248557
0.8092	Intermediate Similarity	NPC211352
0.8087	Intermediate Similarity	NPC117115
0.8083	Intermediate Similarity	NPC473931
0.8083	Intermediate Similarity	NPC474114
0.8083	Intermediate Similarity	NPC474050
0.808	Intermediate Similarity	NPC471794
0.8077	Intermediate Similarity	NPC153019
0.807	Intermediate Similarity	NPC235762
0.807	Intermediate Similarity	NPC233827
0.807	Intermediate Similarity	NPC471228
0.8067	Intermediate Similarity	NPC46940
0.8053	Intermediate Similarity	NPC294741
0.8051	Intermediate Similarity	NPC296683
0.8049	Intermediate Similarity	NPC121866
0.8049	Intermediate Similarity	NPC93071
0.8049	Intermediate Similarity	NPC126002
0.8036	Intermediate Similarity	NPC474073
0.8036	Intermediate Similarity	NPC475078
0.8034	Intermediate Similarity	NPC262365
0.8033	Intermediate Similarity	NPC16030
0.8017	Intermediate Similarity	NPC271274
0.8017	Intermediate Similarity	NPC84999
0.8017	Intermediate Similarity	NPC474486
0.8017	Intermediate Similarity	NPC54765
0.8017	Intermediate Similarity	NPC246760
0.8016	Intermediate Similarity	NPC471187
0.8015	Intermediate Similarity	NPC289624
0.8015	Intermediate Similarity	NPC85595
0.8015	Intermediate Similarity	NPC27578
0.8	Intermediate Similarity	NPC296144
0.8	Intermediate Similarity	NPC28784
0.8	Intermediate Similarity	NPC715
0.8	Intermediate Similarity	NPC253627
0.8	Intermediate Similarity	NPC272029
0.8	Intermediate Similarity	NPC77569
0.8	Intermediate Similarity	NPC142198
0.7984	Intermediate Similarity	NPC47288
0.7984	Intermediate Similarity	NPC176590
0.7983	Intermediate Similarity	NPC308689
0.7983	Intermediate Similarity	NPC275627
0.7982	Intermediate Similarity	NPC51015
0.7982	Intermediate Similarity	NPC80800
0.797	Intermediate Similarity	NPC279463
0.7967	Intermediate Similarity	NPC48781
0.7967	Intermediate Similarity	NPC9592
0.7965	Intermediate Similarity	NPC299762
0.7965	Intermediate Similarity	NPC33675
0.7953	Intermediate Similarity	NPC10154
0.7953	Intermediate Similarity	NPC181334
0.7953	Intermediate Similarity	NPC265413
0.7949	Intermediate Similarity	NPC66834
0.7949	Intermediate Similarity	NPC151477
0.7939	Intermediate Similarity	NPC258073
0.7937	Intermediate Similarity	NPC11250
0.7937	Intermediate Similarity	NPC71094
0.7934	Intermediate Similarity	NPC12656
0.7931	Intermediate Similarity	NPC138942
0.7928	Intermediate Similarity	NPC152415
0.7917	Intermediate Similarity	NPC98372
0.7907	Intermediate Similarity	NPC471077
0.7899	Intermediate Similarity	NPC208229
0.7899	Intermediate Similarity	NPC44732
0.7895	Intermediate Similarity	NPC72729
0.7895	Intermediate Similarity	NPC225506
0.7895	Intermediate Similarity	NPC130103
0.7895	Intermediate Similarity	NPC174911
0.7891	Intermediate Similarity	NPC87985
0.7886	Intermediate Similarity	NPC299180
0.7881	Intermediate Similarity	NPC95344
0.7876	Intermediate Similarity	NPC79241
0.7876	Intermediate Similarity	NPC6597
0.7874	Intermediate Similarity	NPC198014
0.7869	Intermediate Similarity	NPC232165
0.7863	Intermediate Similarity	NPC67250
0.7857	Intermediate Similarity	NPC475839
0.7857	Intermediate Similarity	NPC222146
0.7857	Intermediate Similarity	NPC32714
0.7845	Intermediate Similarity	NPC288411
0.784	Intermediate Similarity	NPC475245
0.7838	Intermediate Similarity	NPC306884
0.7838	Intermediate Similarity	NPC162314
0.7838	Intermediate Similarity	NPC29373
0.7838	Intermediate Similarity	NPC210497
0.7838	Intermediate Similarity	NPC94139
0.7838	Intermediate Similarity	NPC147284
0.7838	Intermediate Similarity	NPC3358
0.7838	Intermediate Similarity	NPC55903
0.7823	Intermediate Similarity	NPC206205
0.7815	Intermediate Similarity	NPC58865
0.7815	Intermediate Similarity	NPC26013
0.7815	Intermediate Similarity	NPC98392
0.7815	Intermediate Similarity	NPC282855
0.7807	Intermediate Similarity	NPC252821
0.7807	Intermediate Similarity	NPC92730
0.7807	Intermediate Similarity	NPC122005
0.7803	Intermediate Similarity	NPC312341
0.7797	Intermediate Similarity	NPC472979
0.7797	Intermediate Similarity	NPC27252
0.7795	Intermediate Similarity	NPC321402
0.7795	Intermediate Similarity	NPC152946
0.7788	Intermediate Similarity	NPC312132
0.7788	Intermediate Similarity	NPC259512
0.7787	Intermediate Similarity	NPC473137
0.7786	Intermediate Similarity	NPC206028
0.7778	Intermediate Similarity	NPC164852
0.7778	Intermediate Similarity	NPC471350
0.7778	Intermediate Similarity	NPC129176
0.7778	Intermediate Similarity	NPC259703
0.7778	Intermediate Similarity	NPC243601
0.7778	Intermediate Similarity	NPC32322
0.7778	Intermediate Similarity	NPC474175
0.7778	Intermediate Similarity	NPC99557
0.7778	Intermediate Similarity	NPC219286

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 NPC323074 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	889
0.2-0.3	1346
0.3-0.4	2940
0.4-0.5	2114
0.5-0.6	1269
0.6-0.7	296
0.7-0.8	39
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
0.843	Intermediate Similarity	NPD3095	Discontinued
0.8378	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8376	Intermediate Similarity	NPD7635	Approved
0.8264	Intermediate Similarity	NPD3091	Approved
0.8031	Intermediate Similarity	NPD3094	Phase 2
0.8	Intermediate Similarity	NPD3092	Approved
0.7807	Intermediate Similarity	NPD3020	Approved
0.7797	Intermediate Similarity	NPD2342	Discontinued
0.7788	Intermediate Similarity	NPD288	Approved
0.7778	Intermediate Similarity	NPD3026	Approved
0.7778	Intermediate Similarity	NPD3023	Approved
0.7769	Intermediate Similarity	NPD5736	Approved
0.7717	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD844	Approved
0.7698	Intermediate Similarity	NPD3019	Approved
0.7698	Intermediate Similarity	NPD4059	Approved
0.7679	Intermediate Similarity	NPD845	Approved
0.7667	Intermediate Similarity	NPD3022	Approved
0.7667	Intermediate Similarity	NPD3021	Approved
0.7661	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3024	Approved
0.7619	Intermediate Similarity	NPD3025	Approved
0.7611	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6671	Approved
0.7561	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD2932	Approved
0.7544	Intermediate Similarity	NPD2860	Approved
0.7544	Intermediate Similarity	NPD1809	Phase 2
0.7544	Intermediate Similarity	NPD2859	Approved
0.7541	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD6663	Approved
0.7521	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD2861	Phase 2
0.7462	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2934	Approved
0.7456	Intermediate Similarity	NPD2933	Approved
0.7391	Intermediate Similarity	NPD7743	Approved
0.7391	Intermediate Similarity	NPD7742	Approved
0.7377	Intermediate Similarity	NPD1792	Phase 2
0.736	Intermediate Similarity	NPD497	Approved
0.7348	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4093	Discontinued
0.7328	Intermediate Similarity	NPD5327	Phase 3
0.7293	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD496	Approved
0.728	Intermediate Similarity	NPD495	Approved
0.728	Intermediate Similarity	NPD498	Approved
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7226	Intermediate Similarity	NPD3620	Phase 2
0.7226	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5735	Approved
0.7164	Intermediate Similarity	NPD4624	Approved
0.7154	Intermediate Similarity	NPD1751	Approved
0.7132	Intermediate Similarity	NPD7741	Discontinued
0.7132	Intermediate Similarity	NPD7330	Discontinued
0.7131	Intermediate Similarity	NPD1444	Approved
0.7131	Intermediate Similarity	NPD1445	Approved
0.7122	Intermediate Similarity	NPD4097	Suspended
0.7122	Intermediate Similarity	NPD6353	Approved
0.7121	Intermediate Similarity	NPD2233	Approved
0.7121	Intermediate Similarity	NPD2232	Approved
0.7121	Intermediate Similarity	NPD2230	Approved
0.7109	Intermediate Similarity	NPD7340	Approved
0.7101	Intermediate Similarity	NPD4140	Approved
0.7101	Intermediate Similarity	NPD4060	Phase 1
0.7099	Intermediate Similarity	NPD3496	Discontinued
0.7083	Intermediate Similarity	NPD940	Approved
0.7083	Intermediate Similarity	NPD846	Approved
0.708	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2606	Approved
0.7059	Intermediate Similarity	NPD4908	Phase 1
0.7059	Intermediate Similarity	NPD2605	Approved
0.705	Intermediate Similarity	NPD3657	Discovery
0.7045	Intermediate Similarity	NPD1201	Approved
0.7031	Intermediate Similarity	NPD6387	Discontinued
0.7025	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2286	Discontinued
0.7023	Intermediate Similarity	NPD4589	Approved
0.7014	Intermediate Similarity	NPD8166	Discontinued
0.7008	Intermediate Similarity	NPD2229	Approved
0.7008	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD2234	Approved
0.7008	Intermediate Similarity	NPD2228	Approved
0.7007	Intermediate Similarity	NPD5156	Approved
0.7007	Intermediate Similarity	NPD5155	Approved
0.7	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD968	Approved
0.6986	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7041	Phase 2
0.6985	Remote Similarity	NPD3636	Approved
0.6985	Remote Similarity	NPD3637	Approved
0.6985	Remote Similarity	NPD3635	Approved
0.6966	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1470	Approved
0.6944	Remote Similarity	NPD3638	Discontinued
0.6939	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3595	Approved
0.6934	Remote Similarity	NPD3594	Approved
0.6912	Remote Similarity	NPD2194	Approved
0.6912	Remote Similarity	NPD2195	Approved
0.6899	Remote Similarity	NPD7157	Approved
0.6894	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4626	Approved
0.6884	Remote Similarity	NPD4625	Phase 3
0.6875	Remote Similarity	NPD4257	Approved
0.6875	Remote Similarity	NPD4256	Phase 2
0.6875	Remote Similarity	NPD1398	Phase 1
0.6875	Remote Similarity	NPD5283	Phase 1
0.687	Remote Similarity	NPD5304	Approved
0.687	Remote Similarity	NPD5303	Approved
0.686	Remote Similarity	NPD1242	Phase 1
0.6857	Remote Similarity	NPD2238	Phase 2
0.6857	Remote Similarity	NPD6346	Approved
0.6846	Remote Similarity	NPD7636	Approved
0.6828	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9618	Approved
0.6822	Remote Similarity	NPD1793	Approved
0.6822	Remote Similarity	NPD1791	Approved
0.6822	Remote Similarity	NPD9614	Approved
0.6818	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4749	Approved
0.6814	Remote Similarity	NPD111	Approved
0.6806	Remote Similarity	NPD5762	Approved
0.6806	Remote Similarity	NPD5763	Approved
0.6791	Remote Similarity	NPD1610	Phase 2
0.6791	Remote Similarity	NPD1611	Approved
0.6788	Remote Similarity	NPD6584	Phase 3
0.6783	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6090	Discontinued
0.6765	Remote Similarity	NPD8651	Approved
0.6763	Remote Similarity	NPD7095	Approved
0.6763	Remote Similarity	NPD3027	Phase 3
0.6741	Remote Similarity	NPD2231	Phase 2
0.6741	Remote Similarity	NPD2235	Phase 2
0.6736	Remote Similarity	NPD6099	Approved
0.6736	Remote Similarity	NPD6100	Approved
0.6736	Remote Similarity	NPD2935	Discontinued
0.6721	Remote Similarity	NPD3028	Approved
0.6692	Remote Similarity	NPD475	Phase 2
0.6692	Remote Similarity	NPD2629	Approved
0.6692	Remote Similarity	NPD5691	Approved
0.6692	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5585	Approved
0.6691	Remote Similarity	NPD4659	Approved
0.669	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4725	Approved
0.669	Remote Similarity	NPD4721	Approved
0.669	Remote Similarity	NPD4726	Approved
0.6667	Remote Similarity	NPD4248	Discontinued
0.6667	Remote Similarity	NPD9616	Approved
0.6667	Remote Similarity	NPD6405	Approved
0.6667	Remote Similarity	NPD6407	Approved
0.6667	Remote Similarity	NPD9613	Approved
0.6667	Remote Similarity	NPD9615	Approved
0.6642	Remote Similarity	NPD7725	Approved
0.6641	Remote Similarity	NPD709	Approved
0.6622	Remote Similarity	NPD8131	Suspended
0.662	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1613	Approved
0.6617	Remote Similarity	NPD316	Approved
0.6613	Remote Similarity	NPD9500	Approved
0.66	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3645	Discontinued
0.66	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6674	Discontinued
0.6597	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7097	Phase 1
0.6594	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD4103	Phase 2
0.6593	Remote Similarity	NPD3143	Discontinued
0.6591	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD228	Approved
0.6581	Remote Similarity	NPD5929	Approved
0.6577	Remote Similarity	NPD3300	Phase 2
0.6573	Remote Similarity	NPD6355	Discontinued
0.6571	Remote Similarity	NPD596	Approved
0.6571	Remote Similarity	NPD600	Approved
0.6569	Remote Similarity	NPD6582	Phase 2
0.6569	Remote Similarity	NPD6583	Phase 3
0.6569	Remote Similarity	NPD1755	Approved
0.6567	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5451	Approved
0.6554	Remote Similarity	NPD7003	Approved
0.6554	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD3892	Phase 2
0.6552	Remote Similarity	NPD1753	Discontinued
0.6549	Remote Similarity	NPD840	Approved
0.6549	Remote Similarity	NPD839	Approved
0.6549	Remote Similarity	NPD8032	Phase 2
0.6538	Remote Similarity	NPD7738	Approved
0.6538	Remote Similarity	NPD1138	Approved
0.6538	Remote Similarity	NPD7843	Approved
0.6538	Remote Similarity	NPD7737	Approved
0.6535	Remote Similarity	NPD290	Approved
0.6531	Remote Similarity	NPD7037	Approved
0.6522	Remote Similarity	NPD1283	Approved
0.6519	Remote Similarity	NPD2668	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