NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	652.25
Volume:	647.615
LogP:	4.002
LogD:	2.372
LogS:	-4.319
# Rotatable Bonds:	13
TPSA:	160.96
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	5.836
Fsp3:	0.514
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.282
MDCK Permeability:	4.3879819713765755e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.337
Plasma Protein Binding (PPB):	78.13372039794922%
Volume Distribution (VD):	1.778
Pgp-substrate:	12.983835220336914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.561
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.917
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.566
CYP3A4-substrate:	0.433

ADMET: Excretion

Clearance (CL):	4.476
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.178
Human Hepatotoxicity (H-HT):	0.459
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.193
Skin Sensitization:	0.429
Carcinogencity:	0.459
Eye Corrosion:	0.003
Eye Irritation:	0.105
Respiratory Toxicity:	0.23

Download Data

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

Natural Product: NPC70685

Natural Product ID:	NPC70685
*Common Name:**	Warburganal
IUPAC Name:	(1S,4aS,8aS)-1-hydroxy-5,5,8a-trimethyl-4a,6,7,8-tetrahydro-4H-naphthalene-1,2-dicarbaldehyde
Synonyms:	Warburganal
Standard InCHIKey:	QGMWDUUHVVLHNP-AEGPPILISA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-13(2)7-4-8-14(3)12(13)6-5-11(9-16)15(14,18)10-17/h5,9-10,12,18H,4,6-8H2,1-3H3/t12-,14-,15+/m0/s1
SMILES:	O=CC1=CC[C@@H]2[C@]([C@@]1(O)C=O)(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452492
PubChem CID:	72502
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10993146]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	Tsukuba, Japan	1998-JUN	PMID[12381108]
NPO19593	Placida dendritica	Species	Limapontiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575447]
NPO19593	Placida dendritica	Species	Limapontiidae	Eukaryota	n.a.	Mediterranean	n.a.	PMID[14575447]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24197199]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24254087]
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24725159]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO30896	Polygonum hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30896	Polygonum hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Nippon Kogaku Zasshi, 91, (1970), 762]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO17965	Helenium arizonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30896	Polygonum hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19652	Pittosporum phillyraeoides	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4929	Pyropia perforata	Species	Bangiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17965	Helenium arizonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14437	Rimularia gibbosa	Species	Trapeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22984	Aframomum sceptrum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19593	Placida dendritica	Species	Limapontiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5929	Neoscopelus microchir	Species	Neoscopelidae	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
LD50	1
MIC	30
Others	12

Activity Type	# Activity
Cell Line	1
Organism	42

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Activity	=	0.01	ug ml-1	PMID[515375]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[515374]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[515374]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[515374]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[515374]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[515374]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[515374]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	3.13	ug.mL-1	PMID[515374]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	MIC	=	12.5	ug.mL-1	PMID[515374]
NPT767	Organism	Pichia jadinii	Cyberlindnera jadinii	MIC	=	3.13	ug.mL-1	PMID[515374]
NPT768	Organism	Sclerotinia	Sclerotinia	MIC	=	3.13	ug.mL-1	PMID[515374]
NPT769	Organism	Mucor mucedo	Mucor mucedo	MIC	=	25.0	ug.mL-1	PMID[515374]
NPT770	Organism	Rhizopus microsporus var. chinensis	Rhizopus microsporus var. chinensis	MIC	=	100.0	ug.mL-1	PMID[515374]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	50.0	ug.mL-1	PMID[515374]
NPT771	Organism	Penicillium crustosum	Penicillium crustosum	MIC	=	50.0	ug.mL-1	PMID[515374]
NPT772	Organism	Pichia anomala	Wickerhamomyces anomalus	MIC	=	12.5	ug.mL-1	PMID[515374]
NPT1191	Organism	Spodoptera exempta	Spodoptera exempta	Activity	=	0.1	ppm	PMID[515375]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	10.0	ppm	PMID[515375]
NPT3772	Organism	Schistocerca gregaria	Schistocerca gregaria	Activity	=	85.0	%	PMID[515375]
NPT2780	Organism	Locusta migratoria	Locusta migratoria	Activity	=	85.0	%	PMID[515375]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	12.5	ug ml-1	PMID[515375]
NPT767	Organism	Pichia jadinii	Cyberlindnera jadinii	Activity	=	3.1	ug ml-1	PMID[515375]
NPT638	Organism	Sclerotinia sclerotiorum	Sclerotinia sclerotiorum	Activity	=	50.0	ug ml-1	PMID[515375]
NPT769	Organism	Mucor mucedo	Mucor mucedo	Activity	=	100.0	ug ml-1	PMID[515375]
NPT3469	Organism	Biomphalaria glabrata	Biomphalaria glabrata	Activity	=	5.0	ppm	PMID[515375]
NPT3775	Organism	Biomphalaria pfeifferi	Biomphalaria pfeifferi	Activity	=	5.0	ppm	PMID[515375]
NPT3776	Organism	Lymnaea natalensis	Radix natalensis	Activity	=	10.0	ppm	PMID[515375]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	20.4	mg.kg-1	PMID[515375]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	50.0	ug.mL-1	PMID[515376]
NPT770	Organism	Rhizopus microsporus var. chinensis	Rhizopus microsporus var. chinensis	MIC	=	100.0	ug.mL-1	PMID[515376]
NPT768	Organism	Sclerotinia	Sclerotinia	MIC	=	3.13	ug.mL-1	PMID[515376]
NPT772	Organism	Pichia anomala	Wickerhamomyces anomalus	MIC	=	12.5	ug.mL-1	PMID[515376]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	MIC	=	12.5	ug.mL-1	PMID[515376]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[515376]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[515376]
NPT771	Organism	Penicillium crustosum	Penicillium crustosum	MIC	=	50.0	ug.mL-1	PMID[515376]
NPT769	Organism	Mucor mucedo	Mucor mucedo	MIC	=	25.0	ug.mL-1	PMID[515376]
NPT767	Organism	Pichia jadinii	Cyberlindnera jadinii	MIC	=	3.13	ug.mL-1	PMID[515376]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	3.13	ug.mL-1	PMID[515376]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[515376]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[515376]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[515376]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[515376]

☑ 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 NPC70685 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	172
0.1-0.2	1193
0.2-0.3	5548
0.3-0.4	13647
0.4-0.5	11558
0.5-0.6	6857
0.6-0.7	3173
0.7-0.8	519
0.8-0.85	26
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9294	High Similarity	NPC172101
0.8889	High Similarity	NPC472301
0.8587	High Similarity	NPC174314
0.8415	Intermediate Similarity	NPC80088
0.8415	Intermediate Similarity	NPC253561
0.8313	Intermediate Similarity	NPC152061
0.8276	Intermediate Similarity	NPC194417
0.8256	Intermediate Similarity	NPC470812
0.8214	Intermediate Similarity	NPC148685
0.8214	Intermediate Similarity	NPC157895
0.8214	Intermediate Similarity	NPC104120
0.8202	Intermediate Similarity	NPC472983
0.8193	Intermediate Similarity	NPC62336
0.8171	Intermediate Similarity	NPC263582
0.8171	Intermediate Similarity	NPC7629
0.8171	Intermediate Similarity	NPC151622
0.8144	Intermediate Similarity	NPC1679
0.8118	Intermediate Similarity	NPC119229
0.8118	Intermediate Similarity	NPC116797
0.8095	Intermediate Similarity	NPC308038
0.809	Intermediate Similarity	NPC471793
0.809	Intermediate Similarity	NPC471791
0.8072	Intermediate Similarity	NPC34110
0.8072	Intermediate Similarity	NPC257666
0.8072	Intermediate Similarity	NPC266193
0.8068	Intermediate Similarity	NPC472974
0.8046	Intermediate Similarity	NPC476412
0.8	Intermediate Similarity	NPC172013
0.8	Intermediate Similarity	NPC45495
0.8	Intermediate Similarity	NPC471514
0.7978	Intermediate Similarity	NPC220930
0.7978	Intermediate Similarity	NPC272039
0.7976	Intermediate Similarity	NPC471409
0.7976	Intermediate Similarity	NPC475994
0.7976	Intermediate Similarity	NPC275494
0.7976	Intermediate Similarity	NPC207772
0.7957	Intermediate Similarity	NPC476245
0.7955	Intermediate Similarity	NPC255174
0.7955	Intermediate Similarity	NPC476426
0.7952	Intermediate Similarity	NPC19907
0.7952	Intermediate Similarity	NPC472305
0.7931	Intermediate Similarity	NPC307258
0.7912	Intermediate Similarity	NPC230332
0.7912	Intermediate Similarity	NPC472476
0.7907	Intermediate Similarity	NPC226068
0.7889	Intermediate Similarity	NPC58271
0.7889	Intermediate Similarity	NPC72397
0.7882	Intermediate Similarity	NPC7232
0.7882	Intermediate Similarity	NPC281138
0.7865	Intermediate Similarity	NPC198761
0.7865	Intermediate Similarity	NPC470955
0.7857	Intermediate Similarity	NPC197659
0.7857	Intermediate Similarity	NPC74995
0.7857	Intermediate Similarity	NPC97377
0.7848	Intermediate Similarity	NPC4370
0.7848	Intermediate Similarity	NPC290350
0.7831	Intermediate Similarity	NPC476795
0.7816	Intermediate Similarity	NPC93590
0.7816	Intermediate Similarity	NPC103486
0.7816	Intermediate Similarity	NPC470813
0.7805	Intermediate Similarity	NPC247586
0.7802	Intermediate Similarity	NPC472973
0.7791	Intermediate Similarity	NPC138492
0.7791	Intermediate Similarity	NPC271104
0.7791	Intermediate Similarity	NPC233352
0.7791	Intermediate Similarity	NPC108955
0.7791	Intermediate Similarity	NPC824
0.7765	Intermediate Similarity	NPC478122
0.7765	Intermediate Similarity	NPC59436
0.7755	Intermediate Similarity	NPC131366
0.7753	Intermediate Similarity	NPC474853
0.7753	Intermediate Similarity	NPC79573
0.7753	Intermediate Similarity	NPC179006
0.7742	Intermediate Similarity	NPC115021
0.7742	Intermediate Similarity	NPC151722
0.7738	Intermediate Similarity	NPC186554
0.7738	Intermediate Similarity	NPC76966
0.7738	Intermediate Similarity	NPC470525
0.7727	Intermediate Similarity	NPC297398
0.7727	Intermediate Similarity	NPC64600
0.7727	Intermediate Similarity	NPC470165
0.7717	Intermediate Similarity	NPC134321
0.7701	Intermediate Similarity	NPC55869
0.7701	Intermediate Similarity	NPC90055
0.7701	Intermediate Similarity	NPC6663
0.7692	Intermediate Similarity	NPC473229
0.7692	Intermediate Similarity	NPC206060
0.7692	Intermediate Similarity	NPC48107
0.7692	Intermediate Similarity	NPC307298
0.7683	Intermediate Similarity	NPC474562
0.7683	Intermediate Similarity	NPC84790
0.7674	Intermediate Similarity	NPC170394
0.7674	Intermediate Similarity	NPC19900
0.7667	Intermediate Similarity	NPC472985
0.7667	Intermediate Similarity	NPC472986
0.7667	Intermediate Similarity	NPC476043
0.764	Intermediate Similarity	NPC237712
0.7634	Intermediate Similarity	NPC116726
0.7634	Intermediate Similarity	NPC99380
0.7634	Intermediate Similarity	NPC472978
0.7614	Intermediate Similarity	NPC38796
0.7614	Intermediate Similarity	NPC158411
0.7609	Intermediate Similarity	NPC472971
0.7609	Intermediate Similarity	NPC472676
0.7609	Intermediate Similarity	NPC184663
0.7609	Intermediate Similarity	NPC472475
0.7609	Intermediate Similarity	NPC472688
0.7609	Intermediate Similarity	NPC472970
0.7609	Intermediate Similarity	NPC472477
0.7604	Intermediate Similarity	NPC471916
0.759	Intermediate Similarity	NPC186042
0.759	Intermediate Similarity	NPC35656
0.7586	Intermediate Similarity	NPC472478
0.7586	Intermediate Similarity	NPC476809
0.7586	Intermediate Similarity	NPC2482
0.7558	Intermediate Similarity	NPC179028
0.7558	Intermediate Similarity	NPC178852
0.7558	Intermediate Similarity	NPC198240
0.7558	Intermediate Similarity	NPC297996
0.7558	Intermediate Similarity	NPC189485
0.7556	Intermediate Similarity	NPC241512
0.7556	Intermediate Similarity	NPC15807
0.7556	Intermediate Similarity	NPC263997
0.7556	Intermediate Similarity	NPC8518
0.7556	Intermediate Similarity	NPC132228
0.7556	Intermediate Similarity	NPC6185
0.7553	Intermediate Similarity	NPC476416
0.7531	Intermediate Similarity	NPC155198
0.7529	Intermediate Similarity	NPC180886
0.7528	Intermediate Similarity	NPC49019
0.7528	Intermediate Similarity	NPC169941
0.7528	Intermediate Similarity	NPC97913
0.7528	Intermediate Similarity	NPC105173
0.7528	Intermediate Similarity	NPC251475
0.7527	Intermediate Similarity	NPC128672
0.7527	Intermediate Similarity	NPC48010
0.7527	Intermediate Similarity	NPC113393
0.7527	Intermediate Similarity	NPC191684
0.7526	Intermediate Similarity	NPC316598
0.75	Intermediate Similarity	NPC474854
0.75	Intermediate Similarity	NPC53454
0.75	Intermediate Similarity	NPC192428
0.75	Intermediate Similarity	NPC473217
0.75	Intermediate Similarity	NPC189237
0.75	Intermediate Similarity	NPC44963
0.75	Intermediate Similarity	NPC78527
0.75	Intermediate Similarity	NPC470298
0.75	Intermediate Similarity	NPC215050
0.75	Intermediate Similarity	NPC94337
0.75	Intermediate Similarity	NPC121984
0.75	Intermediate Similarity	NPC472684
0.75	Intermediate Similarity	NPC470299
0.75	Intermediate Similarity	NPC474925
0.75	Intermediate Similarity	NPC472870
0.75	Intermediate Similarity	NPC104560
0.7474	Intermediate Similarity	NPC292793
0.7474	Intermediate Similarity	NPC472976
0.7474	Intermediate Similarity	NPC299100
0.7474	Intermediate Similarity	NPC196227
0.7474	Intermediate Similarity	NPC472977
0.7473	Intermediate Similarity	NPC82979
0.7473	Intermediate Similarity	NPC327115
0.7473	Intermediate Similarity	NPC472869
0.7473	Intermediate Similarity	NPC472479
0.7473	Intermediate Similarity	NPC179591
0.7473	Intermediate Similarity	NPC94666
0.7473	Intermediate Similarity	NPC473226
0.7471	Intermediate Similarity	NPC472490
0.7471	Intermediate Similarity	NPC27817
0.7471	Intermediate Similarity	NPC283789
0.7447	Intermediate Similarity	NPC252433
0.7447	Intermediate Similarity	NPC26865
0.7447	Intermediate Similarity	NPC230064
0.7447	Intermediate Similarity	NPC475806
0.7447	Intermediate Similarity	NPC73457
0.7447	Intermediate Similarity	NPC472814
0.7447	Intermediate Similarity	NPC177037
0.7447	Intermediate Similarity	NPC472975
0.7444	Intermediate Similarity	NPC472865
0.7444	Intermediate Similarity	NPC144258
0.7444	Intermediate Similarity	NPC164577
0.7444	Intermediate Similarity	NPC227132
0.7444	Intermediate Similarity	NPC40687
0.7442	Intermediate Similarity	NPC470428
0.7442	Intermediate Similarity	NPC325946
0.7442	Intermediate Similarity	NPC61952
0.7442	Intermediate Similarity	NPC203403
0.7439	Intermediate Similarity	NPC136473
0.7419	Intermediate Similarity	NPC473999
0.7419	Intermediate Similarity	NPC472489
0.7419	Intermediate Similarity	NPC5509
0.7419	Intermediate Similarity	NPC118011
0.7419	Intermediate Similarity	NPC123912
0.7419	Intermediate Similarity	NPC36668
0.7419	Intermediate Similarity	NPC309603
0.7419	Intermediate Similarity	NPC310010
0.7419	Intermediate Similarity	NPC168131
0.7419	Intermediate Similarity	NPC474918
0.7419	Intermediate Similarity	NPC326627
0.7416	Intermediate Similarity	NPC48362

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 NPC70685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1634
0.2-0.3	3934
0.3-0.4	2406
0.4-0.5	620
0.5-0.6	228
0.6-0.7	154
0.7-0.8	10
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
0.7586	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD4697	Phase 3
0.7473	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4519	Discontinued
0.7473	Intermediate Similarity	NPD5690	Phase 2
0.7473	Intermediate Similarity	NPD4623	Approved
0.7444	Intermediate Similarity	NPD4197	Approved
0.7419	Intermediate Similarity	NPD4753	Phase 2
0.7363	Intermediate Similarity	NPD1696	Phase 3
0.7363	Intermediate Similarity	NPD5329	Approved
0.73	Intermediate Similarity	NPD5211	Phase 2
0.7283	Intermediate Similarity	NPD5279	Phase 3
0.7283	Intermediate Similarity	NPD3618	Phase 1
0.7283	Intermediate Similarity	NPD4694	Approved
0.7283	Intermediate Similarity	NPD5280	Approved
0.7253	Intermediate Similarity	NPD3133	Approved
0.7253	Intermediate Similarity	NPD3666	Approved
0.7253	Intermediate Similarity	NPD3665	Phase 1
0.7222	Intermediate Similarity	NPD4223	Phase 3
0.7222	Intermediate Similarity	NPD4221	Approved
0.7216	Intermediate Similarity	NPD4629	Approved
0.7216	Intermediate Similarity	NPD5210	Approved
0.7159	Intermediate Similarity	NPD3617	Approved
0.7157	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5285	Approved
0.71	Intermediate Similarity	NPD4696	Approved
0.71	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD6079	Approved
0.7071	Intermediate Similarity	NPD4755	Approved
0.7071	Intermediate Similarity	NPD5173	Approved
0.7053	Intermediate Similarity	NPD5328	Approved
0.7041	Intermediate Similarity	NPD5695	Phase 3
0.7033	Intermediate Similarity	NPD3667	Approved
0.703	Intermediate Similarity	NPD5223	Approved
0.701	Intermediate Similarity	NPD4202	Approved
0.6961	Remote Similarity	NPD5226	Approved
0.6961	Remote Similarity	NPD4633	Approved
0.6961	Remote Similarity	NPD5225	Approved
0.6961	Remote Similarity	NPD5224	Approved
0.6931	Remote Similarity	NPD4700	Approved
0.6915	Remote Similarity	NPD4138	Approved
0.6915	Remote Similarity	NPD4689	Approved
0.6915	Remote Similarity	NPD5205	Approved
0.6915	Remote Similarity	NPD4690	Approved
0.6915	Remote Similarity	NPD4688	Approved
0.6915	Remote Similarity	NPD4693	Phase 3
0.6907	Remote Similarity	NPD7515	Phase 2
0.69	Remote Similarity	NPD6083	Phase 2
0.69	Remote Similarity	NPD6084	Phase 2
0.6893	Remote Similarity	NPD5174	Approved
0.6893	Remote Similarity	NPD5175	Approved
0.6882	Remote Similarity	NPD4786	Approved
0.6848	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5696	Approved
0.6822	Remote Similarity	NPD4634	Approved
0.6809	Remote Similarity	NPD1694	Approved
0.6771	Remote Similarity	NPD6672	Approved
0.6771	Remote Similarity	NPD5737	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6744	Remote Similarity	NPD4691	Approved
0.6733	Remote Similarity	NPD7902	Approved
0.6731	Remote Similarity	NPD4754	Approved
0.6703	Remote Similarity	NPD4195	Approved
0.6701	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5133	Approved
0.6636	Remote Similarity	NPD4730	Approved
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD6881	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD6899	Approved
0.6628	Remote Similarity	NPD4137	Phase 3
0.6607	Remote Similarity	NPD7115	Discovery
0.6606	Remote Similarity	NPD6650	Approved
0.6606	Remote Similarity	NPD6649	Approved
0.6604	Remote Similarity	NPD5739	Approved
0.6604	Remote Similarity	NPD4768	Approved
0.6604	Remote Similarity	NPD6675	Approved
0.6604	Remote Similarity	NPD7128	Approved
0.6604	Remote Similarity	NPD6402	Approved
0.6604	Remote Similarity	NPD4767	Approved
0.6596	Remote Similarity	NPD4788	Approved
0.6585	Remote Similarity	NPD368	Approved
0.6574	Remote Similarity	NPD6013	Approved
0.6574	Remote Similarity	NPD6372	Approved
0.6574	Remote Similarity	NPD6012	Approved
0.6574	Remote Similarity	NPD6014	Approved
0.6574	Remote Similarity	NPD6373	Approved
0.6566	Remote Similarity	NPD5284	Approved
0.6566	Remote Similarity	NPD5281	Approved
0.6566	Remote Similarity	NPD5693	Phase 1
0.6562	Remote Similarity	NPD7521	Approved
0.6562	Remote Similarity	NPD6409	Approved
0.6562	Remote Similarity	NPD6684	Approved
0.6562	Remote Similarity	NPD7146	Approved
0.6562	Remote Similarity	NPD5330	Approved
0.6562	Remote Similarity	NPD7334	Approved
0.6552	Remote Similarity	NPD4747	Approved
0.6542	Remote Similarity	NPD5701	Approved
0.6531	Remote Similarity	NPD6904	Approved
0.6531	Remote Similarity	NPD6673	Approved
0.6531	Remote Similarity	NPD6080	Approved
0.6526	Remote Similarity	NPD3668	Phase 3
0.6517	Remote Similarity	NPD4058	Approved
0.6514	Remote Similarity	NPD5248	Approved
0.6514	Remote Similarity	NPD7102	Approved
0.6514	Remote Similarity	NPD5135	Approved
0.6514	Remote Similarity	NPD5249	Phase 3
0.6514	Remote Similarity	NPD7290	Approved
0.6514	Remote Similarity	NPD6883	Approved
0.6514	Remote Similarity	NPD5250	Approved
0.6514	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5247	Approved
0.6514	Remote Similarity	NPD5251	Approved
0.6514	Remote Similarity	NPD5169	Approved
0.65	Remote Similarity	NPD6399	Phase 3
0.6481	Remote Similarity	NPD5168	Approved
0.6481	Remote Similarity	NPD7320	Approved
0.6476	Remote Similarity	NPD5091	Approved
0.6465	Remote Similarity	NPD5692	Phase 3
0.6465	Remote Similarity	NPD4096	Approved
0.6465	Remote Similarity	NPD5785	Approved
0.6458	Remote Similarity	NPD5363	Approved
0.6455	Remote Similarity	NPD6847	Approved
0.6455	Remote Similarity	NPD5217	Approved
0.6455	Remote Similarity	NPD5216	Approved
0.6455	Remote Similarity	NPD8130	Phase 1
0.6455	Remote Similarity	NPD6617	Approved
0.6455	Remote Similarity	NPD5215	Approved
0.6455	Remote Similarity	NPD6869	Approved
0.6455	Remote Similarity	NPD5127	Approved
0.6452	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6404	Discontinued
0.6442	Remote Similarity	NPD7640	Approved
0.6442	Remote Similarity	NPD7639	Approved
0.6436	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7900	Approved
0.6436	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6050	Approved
0.64	Remote Similarity	NPD5694	Approved
0.6396	Remote Similarity	NPD6882	Approved
0.6396	Remote Similarity	NPD8297	Approved
0.6392	Remote Similarity	NPD6098	Approved
0.6383	Remote Similarity	NPD4139	Approved
0.6383	Remote Similarity	NPD4692	Approved
0.6353	Remote Similarity	NPD7341	Phase 2
0.6346	Remote Similarity	NPD7638	Approved
0.6339	Remote Similarity	NPD4632	Approved
0.6337	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD5778	Approved
0.6333	Remote Similarity	NPD4687	Approved
0.6333	Remote Similarity	NPD5733	Approved
0.6316	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4756	Discovery
0.6293	Remote Similarity	NPD6054	Approved
0.6293	Remote Similarity	NPD6319	Approved
0.6292	Remote Similarity	NPD5276	Approved
0.6283	Remote Similarity	NPD5167	Approved
0.6264	Remote Similarity	NPD8264	Approved
0.6263	Remote Similarity	NPD4518	Approved
0.6263	Remote Similarity	NPD5208	Approved
0.6239	Remote Similarity	NPD6015	Approved
0.6239	Remote Similarity	NPD6016	Approved
0.6238	Remote Similarity	NPD6411	Approved
0.6237	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6274	Approved
0.622	Remote Similarity	NPD287	Approved
0.6214	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4522	Approved
0.6196	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6370	Approved
0.6186	Remote Similarity	NPD5988	Approved
0.6174	Remote Similarity	NPD6317	Approved
0.6174	Remote Similarity	NPD6009	Approved
0.617	Remote Similarity	NPD7645	Phase 2
0.6162	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7614	Phase 1
0.6154	Remote Similarity	NPD6059	Approved
0.6146	Remote Similarity	NPD4269	Approved
0.6146	Remote Similarity	NPD4270	Approved
0.6139	Remote Similarity	NPD5207	Approved
0.6136	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6314	Approved
0.6121	Remote Similarity	NPD6313	Approved
0.6121	Remote Similarity	NPD6335	Approved
0.6117	Remote Similarity	NPD6001	Approved
0.6111	Remote Similarity	NPD4243	Approved
0.6105	Remote Similarity	NPD7525	Registered

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