NPASS Compound

Structure

NPC275145 OpenBabel07101719512D 23 24 0 0 1 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 18 2 0 0 0 0 13 3 1 1 0 0 0 14 4 1 6 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 13 1 1 0 0 0 16 17 1 0 0 0 0 17 19 2 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	405.23
Volume:	428.462
LogP:	5.903
LogD:	4.916
LogS:	-4.687
# Rotatable Bonds:	6
TPSA:	47.56
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.741
Synthetic Accessibility Score:	4.614
Fsp3:	0.577
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.78
MDCK Permeability:	6.527033838210627e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.057
30% Bioavailability (F30%):	0.76

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	95.7116470336914%
Volume Distribution (VD):	2.078
Pgp-substrate:	2.3099870681762695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.932
CYP1A2-substrate:	0.233
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.658
CYP2C9-inhibitor:	0.935
CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.852
CYP2D6-substrate:	0.732
CYP3A4-inhibitor:	0.971
CYP3A4-substrate:	0.346

ADMET: Excretion

Clearance (CL):	15.97
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.313
Human Hepatotoxicity (H-HT):	0.605
Drug-inuced Liver Injury (DILI):	0.275
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.731
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.677
Carcinogencity:	0.566
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC275145

Natural Product ID:	NPC275145
*Common Name:**	8-Hydroxyserrulat-14-En-19-Oic Acid
IUPAC Name:	(5R,8S)-4-hydroxy-5-methyl-8-[(2S)-6-methylhept-5-en-2-yl]-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid
Synonyms:
Standard InCHIKey:	CKNOKJMGWBUQGL-LZWOXQAQSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-12(2)6-5-7-13(3)16-9-8-14(4)19-17(16)10-15(20(22)23)11-18(19)21/h6,10-11,13-14,16,21H,5,7-9H2,1-4H3,(H,22,23)/t13-,14+,16-/m0/s1
SMILES:	CC(=CCC[C@@H]([C@@H]1CC[C@H](c2c1cc(cc2O)C(=O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400178
PubChem CID:	23642602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000351] Biflorane and serrulatane diterpenoids

*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
NPO33460	Eremophila neglecta	Species	Scrophulariaceae	Eukaryota	n.a.	Australian desert	n.a.	PMID[17844993]
NPO33460	Eremophila neglecta	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26636180]

☑ 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
MIC	8
Others	45

Activity Type	# Activity
Organism	33
Others	20

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	49300.0	nM	PMID[527999]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	24700.0	nM	PMID[527999]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	24700.0	nM	PMID[527999]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	49.3	uM	PMID[527999]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	99.0	uM	PMID[527999]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MBC	=	99.0	uM	PMID[527999]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MBC	=	49.3	uM	PMID[527999]
NPT2	Others	Unspecified		Activity	=	2.54	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	51.4	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	32.7	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	13.3	%	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	5.0	log10CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	9.0	10'3CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	4.4	10'4CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	1.5	10'7CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	5.0	10'7CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	3.4	10'8CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	3.9	10'4CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	2.7	10'5CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	6.7	10'8CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	9.1	10'8CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	1.6	10'9CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	0.0	CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	6.0	10'3CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	4.2	10'8CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	7.0	log10CFU/ml	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	=	2.0	log10CFU/ml	PMID[528000]
NPT2	Others	Unspecified		Activity	=	6.76	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	27.0	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	62.2	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	4.05	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	21.8	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	27.7	%	PMID[528000]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	41.0	uM	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	=	82.0	uM	PMID[528000]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	82.0	uM	PMID[528000]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	41000.0	nM	PMID[528000]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	82000.0	nM	PMID[528000]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	82000.0	nM	PMID[528000]
NPT2	Others	Unspecified		Activity	=	49.5	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	0.99	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	23.9	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	44.4	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	31.0	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	0.81	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	0.63	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	3.88	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	53.0	%	PMID[528000]
NPT2	Others	Unspecified		Activity	=	42.5	%	PMID[528000]

☑ 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 NPC275145 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	272
0.1-0.2	1421
0.2-0.3	3168
0.3-0.4	8587
0.4-0.5	10921
0.5-0.6	6765
0.6-0.7	9066
0.7-0.8	2150
0.8-0.85	239
0.85-0.9	94
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC160199
0.9008	High Similarity	NPC25168
0.9	High Similarity	NPC478121
0.8968	High Similarity	NPC108129
0.8943	High Similarity	NPC199273
0.8934	High Similarity	NPC282577
0.8926	High Similarity	NPC165197
0.8926	High Similarity	NPC241001
0.888	High Similarity	NPC72667
0.888	High Similarity	NPC78364
0.888	High Similarity	NPC176130
0.888	High Similarity	NPC69424
0.888	High Similarity	NPC84672
0.8852	High Similarity	NPC162935
0.8852	High Similarity	NPC249340
0.8846	High Similarity	NPC472308
0.8819	High Similarity	NPC31539
0.881	High Similarity	NPC48248
0.881	High Similarity	NPC3009
0.881	High Similarity	NPC96024
0.88	High Similarity	NPC254492
0.879	High Similarity	NPC117794
0.879	High Similarity	NPC68756
0.879	High Similarity	NPC152525
0.879	High Similarity	NPC236189
0.878	High Similarity	NPC121168
0.878	High Similarity	NPC297193
0.878	High Similarity	NPC307174
0.875	High Similarity	NPC471851
0.874	High Similarity	NPC171460
0.872	High Similarity	NPC131799
0.872	High Similarity	NPC472592
0.872	High Similarity	NPC123506
0.8699	High Similarity	NPC154696
0.8692	High Similarity	NPC202225
0.8678	High Similarity	NPC328694
0.8655	High Similarity	NPC186933
0.8651	High Similarity	NPC227741
0.8651	High Similarity	NPC49647
0.8651	High Similarity	NPC295202
0.8651	High Similarity	NPC136342
0.8651	High Similarity	NPC306765
0.864	High Similarity	NPC74507
0.864	High Similarity	NPC142956
0.864	High Similarity	NPC234890
0.8629	High Similarity	NPC46634
0.8629	High Similarity	NPC244351
0.8626	High Similarity	NPC161632
0.8618	High Similarity	NPC301987
0.8618	High Similarity	NPC292665
0.8618	High Similarity	NPC35856
0.8618	High Similarity	NPC26433
0.8618	High Similarity	NPC164852
0.8618	High Similarity	NPC159760
0.8618	High Similarity	NPC272454
0.8618	High Similarity	NPC178395
0.8618	High Similarity	NPC115188
0.8618	High Similarity	NPC222876
0.8618	High Similarity	NPC179092
0.8618	High Similarity	NPC244994
0.8615	High Similarity	NPC472591
0.8615	High Similarity	NPC115458
0.8607	High Similarity	NPC233165
0.8607	High Similarity	NPC184579
0.8594	High Similarity	NPC276238
0.8594	High Similarity	NPC303910
0.8594	High Similarity	NPC146647
0.8594	High Similarity	NPC117899
0.8594	High Similarity	NPC34414
0.8583	High Similarity	NPC209959
0.8582	High Similarity	NPC225243
0.8561	High Similarity	NPC272268
0.856	High Similarity	NPC273683
0.856	High Similarity	NPC477153
0.855	High Similarity	NPC288089
0.8538	High Similarity	NPC58685
0.8537	High Similarity	NPC285829
0.8537	High Similarity	NPC206778
0.8527	High Similarity	NPC55949
0.8516	High Similarity	NPC193203
0.8516	High Similarity	NPC282923
0.8516	High Similarity	NPC229894
0.8512	High Similarity	NPC477453
0.8504	High Similarity	NPC3224
0.85	High Similarity	NPC114918
0.8492	Intermediate Similarity	NPC173978
0.8485	Intermediate Similarity	NPC290803
0.848	Intermediate Similarity	NPC300274
0.8473	Intermediate Similarity	NPC138472
0.8473	Intermediate Similarity	NPC111845
0.8473	Intermediate Similarity	NPC78307
0.8473	Intermediate Similarity	NPC477139
0.8468	Intermediate Similarity	NPC32322
0.8468	Intermediate Similarity	NPC259703
0.8462	Intermediate Similarity	NPC205992
0.8462	Intermediate Similarity	NPC85342
0.8462	Intermediate Similarity	NPC18798
0.8455	Intermediate Similarity	NPC42657
0.845	Intermediate Similarity	NPC131684
0.8444	Intermediate Similarity	NPC315578
0.8443	Intermediate Similarity	NPC125252
0.8438	Intermediate Similarity	NPC471530
0.8433	Intermediate Similarity	NPC4214
0.843	Intermediate Similarity	NPC161304
0.8421	Intermediate Similarity	NPC118919
0.8413	Intermediate Similarity	NPC471187
0.8413	Intermediate Similarity	NPC375356
0.8409	Intermediate Similarity	NPC27394
0.8403	Intermediate Similarity	NPC66208
0.8385	Intermediate Similarity	NPC136588
0.8385	Intermediate Similarity	NPC199253
0.8385	Intermediate Similarity	NPC198305
0.8374	Intermediate Similarity	NPC273282
0.8374	Intermediate Similarity	NPC474890
0.8374	Intermediate Similarity	NPC161943
0.837	Intermediate Similarity	NPC26924
0.8362	Intermediate Similarity	NPC117115
0.8361	Intermediate Similarity	NPC83718
0.8359	Intermediate Similarity	NPC160499
0.8359	Intermediate Similarity	NPC15837
0.8359	Intermediate Similarity	NPC96915
0.8358	Intermediate Similarity	NPC475957
0.8358	Intermediate Similarity	NPC245923
0.8346	Intermediate Similarity	NPC310540
0.8346	Intermediate Similarity	NPC283088
0.8346	Intermediate Similarity	NPC181334
0.8333	Intermediate Similarity	NPC176208
0.8333	Intermediate Similarity	NPC180261
0.8333	Intermediate Similarity	NPC283514
0.8333	Intermediate Similarity	NPC11250
0.8333	Intermediate Similarity	NPC37299
0.8333	Intermediate Similarity	NPC225051
0.8333	Intermediate Similarity	NPC53896
0.8321	Intermediate Similarity	NPC41847
0.8321	Intermediate Similarity	NPC244699
0.832	Intermediate Similarity	NPC190971
0.8319	Intermediate Similarity	NPC132720
0.8309	Intermediate Similarity	NPC32749
0.8309	Intermediate Similarity	NPC168471
0.8309	Intermediate Similarity	NPC327916
0.8309	Intermediate Similarity	NPC147542
0.8309	Intermediate Similarity	NPC241349
0.8309	Intermediate Similarity	NPC220496
0.8309	Intermediate Similarity	NPC42262
0.8309	Intermediate Similarity	NPC37992
0.8308	Intermediate Similarity	NPC278928
0.8308	Intermediate Similarity	NPC99731
0.8293	Intermediate Similarity	NPC269414
0.8291	Intermediate Similarity	NPC187913
0.8284	Intermediate Similarity	NPC155211
0.8284	Intermediate Similarity	NPC474813
0.8281	Intermediate Similarity	NPC103540
0.8281	Intermediate Similarity	NPC167055
0.8281	Intermediate Similarity	NPC137750
0.8281	Intermediate Similarity	NPC240744
0.8271	Intermediate Similarity	NPC477594
0.8271	Intermediate Similarity	NPC50924
0.8271	Intermediate Similarity	NPC472262
0.8271	Intermediate Similarity	NPC474394
0.8271	Intermediate Similarity	NPC287604
0.8271	Intermediate Similarity	NPC161964
0.8271	Intermediate Similarity	NPC293454
0.8268	Intermediate Similarity	NPC174991
0.8258	Intermediate Similarity	NPC110609
0.8258	Intermediate Similarity	NPC70622
0.8258	Intermediate Similarity	NPC246693
0.8258	Intermediate Similarity	NPC242358
0.8254	Intermediate Similarity	NPC198336
0.8254	Intermediate Similarity	NPC120545
0.825	Intermediate Similarity	NPC228609
0.8244	Intermediate Similarity	NPC253488
0.824	Intermediate Similarity	NPC473662
0.824	Intermediate Similarity	NPC216297
0.824	Intermediate Similarity	NPC7151
0.8235	Intermediate Similarity	NPC256463
0.8235	Intermediate Similarity	NPC306835
0.8235	Intermediate Similarity	NPC29771
0.8235	Intermediate Similarity	NPC471602
0.8235	Intermediate Similarity	NPC111422
0.8235	Intermediate Similarity	NPC299405
0.8235	Intermediate Similarity	NPC476477
0.8235	Intermediate Similarity	NPC216312
0.8226	Intermediate Similarity	NPC41567
0.8222	Intermediate Similarity	NPC471452
0.8222	Intermediate Similarity	NPC62272
0.822	Intermediate Similarity	NPC151477
0.822	Intermediate Similarity	NPC34715
0.8217	Intermediate Similarity	NPC231774
0.8217	Intermediate Similarity	NPC71610
0.8211	Intermediate Similarity	NPC108288
0.8209	Intermediate Similarity	NPC477596
0.8209	Intermediate Similarity	NPC153088
0.8209	Intermediate Similarity	NPC80035
0.8197	Intermediate Similarity	NPC81808
0.8195	Intermediate Similarity	NPC59459
0.8195	Intermediate Similarity	NPC52407
0.8195	Intermediate Similarity	NPC49742
0.8195	Intermediate Similarity	NPC314048
0.8189	Intermediate Similarity	NPC217756
0.8189	Intermediate Similarity	NPC91478

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 NPC275145 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	922
0.2-0.3	1399
0.3-0.4	2497
0.4-0.5	2272
0.5-0.6	1191
0.6-0.7	489
0.7-0.8	93
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8281	Intermediate Similarity	NPD1470	Approved
0.8254	Intermediate Similarity	NPD1201	Approved
0.8222	Intermediate Similarity	NPD5404	Approved
0.8222	Intermediate Similarity	NPD5408	Approved
0.8222	Intermediate Similarity	NPD5405	Approved
0.8222	Intermediate Similarity	NPD5406	Approved
0.8211	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8197	Intermediate Similarity	NPD5951	Approved
0.8162	Intermediate Similarity	NPD2346	Discontinued
0.8033	Intermediate Similarity	NPD7635	Approved
0.8015	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1164	Approved
0.7986	Intermediate Similarity	NPD7003	Approved
0.7956	Intermediate Similarity	NPD2935	Discontinued
0.7953	Intermediate Similarity	NPD3019	Approved
0.7953	Intermediate Similarity	NPD2932	Approved
0.7923	Intermediate Similarity	NPD1283	Approved
0.7874	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4626	Approved
0.7793	Intermediate Similarity	NPD3226	Approved
0.7762	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD2799	Discontinued
0.7731	Intermediate Similarity	NPD1930	Approved
0.7731	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD1929	Approved
0.7705	Intermediate Similarity	NPD9266	Approved
0.7705	Intermediate Similarity	NPD74	Approved
0.7705	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD3764	Approved
0.7692	Intermediate Similarity	NPD7390	Discontinued
0.7692	Intermediate Similarity	NPD1281	Approved
0.7671	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6663	Approved
0.7638	Intermediate Similarity	NPD9493	Approved
0.7627	Intermediate Similarity	NPD2066	Phase 3
0.7623	Intermediate Similarity	NPD9267	Approved
0.7623	Intermediate Similarity	NPD9264	Approved
0.7623	Intermediate Similarity	NPD2342	Discontinued
0.7623	Intermediate Similarity	NPD9263	Approved
0.7612	Intermediate Similarity	NPD5736	Approved
0.7607	Intermediate Similarity	NPD288	Approved
0.7574	Intermediate Similarity	NPD2313	Discontinued
0.7537	Intermediate Similarity	NPD2798	Approved
0.7521	Intermediate Similarity	NPD844	Approved
0.7518	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2532	Approved
0.7517	Intermediate Similarity	NPD2534	Approved
0.7517	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2979	Phase 3
0.7463	Intermediate Similarity	NPD2797	Approved
0.7462	Intermediate Similarity	NPD5691	Approved
0.7376	Intermediate Similarity	NPD4308	Phase 3
0.7372	Intermediate Similarity	NPD7008	Discontinued
0.7372	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD8166	Discontinued
0.7355	Intermediate Similarity	NPD6232	Discontinued
0.7355	Intermediate Similarity	NPD1932	Approved
0.735	Intermediate Similarity	NPD845	Approved
0.7348	Intermediate Similarity	NPD3023	Approved
0.7348	Intermediate Similarity	NPD3026	Approved
0.7347	Intermediate Similarity	NPD6273	Approved
0.7343	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3020	Approved
0.7328	Intermediate Similarity	NPD1651	Approved
0.7328	Intermediate Similarity	NPD3024	Approved
0.7328	Intermediate Similarity	NPD3025	Approved
0.7325	Intermediate Similarity	NPD7473	Discontinued
0.7315	Intermediate Similarity	NPD7458	Discontinued
0.7295	Intermediate Similarity	NPD9261	Approved
0.728	Intermediate Similarity	NPD2329	Discontinued
0.7273	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9545	Approved
0.7241	Intermediate Similarity	NPD3750	Approved
0.7239	Intermediate Similarity	NPD1608	Approved
0.7239	Intermediate Similarity	NPD9269	Phase 2
0.7214	Intermediate Similarity	NPD4060	Phase 1
0.7214	Intermediate Similarity	NPD943	Approved
0.7209	Intermediate Similarity	NPD9281	Approved
0.7206	Intermediate Similarity	NPD1203	Approved
0.7197	Intermediate Similarity	NPD9268	Approved
0.7194	Intermediate Similarity	NPD3268	Approved
0.7194	Intermediate Similarity	NPD411	Approved
0.7172	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1611	Approved
0.7163	Intermediate Similarity	NPD447	Suspended
0.7153	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2182	Approved
0.7133	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1876	Approved
0.7124	Intermediate Similarity	NPD7819	Suspended
0.7123	Intermediate Similarity	NPD4628	Phase 3
0.7121	Intermediate Similarity	NPD3091	Approved
0.7111	Intermediate Similarity	NPD4878	Approved
0.7111	Intermediate Similarity	NPD9717	Approved
0.7111	Intermediate Similarity	NPD3972	Approved
0.7099	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD164	Approved
0.7094	Intermediate Similarity	NPD1090	Approved
0.7094	Intermediate Similarity	NPD1089	Approved
0.7094	Intermediate Similarity	NPD9256	Approved
0.7094	Intermediate Similarity	NPD1086	Approved
0.7094	Intermediate Similarity	NPD9258	Approved
0.7092	Intermediate Similarity	NPD4307	Phase 2
0.7087	Intermediate Similarity	NPD3021	Approved
0.7087	Intermediate Similarity	NPD3022	Approved
0.7083	Intermediate Similarity	NPD2860	Approved
0.7083	Intermediate Similarity	NPD4476	Approved
0.7083	Intermediate Similarity	NPD6100	Approved
0.7083	Intermediate Similarity	NPD2438	Suspended
0.7083	Intermediate Similarity	NPD6099	Approved
0.7083	Intermediate Similarity	NPD4477	Approved
0.7083	Intermediate Similarity	NPD2859	Approved
0.7083	Intermediate Similarity	NPD2531	Phase 2
0.7083	Intermediate Similarity	NPD1809	Phase 2
0.7077	Intermediate Similarity	NPD497	Approved
0.7077	Intermediate Similarity	NPD2629	Approved
0.7059	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD230	Phase 1
0.7034	Intermediate Similarity	NPD2344	Approved
0.7021	Intermediate Similarity	NPD8032	Phase 2
0.7019	Intermediate Similarity	NPD5844	Phase 1
0.7015	Intermediate Similarity	NPD17	Approved
0.7015	Intermediate Similarity	NPD4059	Approved
0.7012	Intermediate Similarity	NPD8313	Approved
0.7012	Intermediate Similarity	NPD8312	Approved
0.7009	Intermediate Similarity	NPD800	Approved
0.7	Intermediate Similarity	NPD2934	Approved
0.7	Intermediate Similarity	NPD495	Approved
0.7	Intermediate Similarity	NPD496	Approved
0.7	Intermediate Similarity	NPD1693	Approved
0.7	Intermediate Similarity	NPD2933	Approved
0.7	Intermediate Similarity	NPD498	Approved
0.6993	Remote Similarity	NPD1607	Approved
0.6988	Remote Similarity	NPD8150	Discontinued
0.6975	Remote Similarity	NPD1088	Approved
0.697	Remote Similarity	NPD7340	Approved
0.6968	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1551	Phase 2
0.696	Remote Similarity	NPD5909	Discontinued
0.696	Remote Similarity	NPD1237	Approved
0.6957	Remote Similarity	NPD7177	Discontinued
0.6953	Remote Similarity	NPD1792	Phase 2
0.6934	Remote Similarity	NPD1755	Approved
0.6929	Remote Similarity	NPD6832	Phase 2
0.6923	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5710	Approved
0.6918	Remote Similarity	NPD5711	Approved
0.6917	Remote Similarity	NPD7644	Approved
0.6917	Remote Similarity	NPD1202	Approved
0.6917	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3092	Approved
0.6897	Remote Similarity	NPD3748	Approved
0.6894	Remote Similarity	NPD256	Approved
0.6894	Remote Similarity	NPD255	Approved
0.6892	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1239	Approved
0.6889	Remote Similarity	NPD2286	Discontinued
0.6889	Remote Similarity	NPD1778	Approved
0.6885	Remote Similarity	NPD1565	Approved
0.6885	Remote Similarity	NPD1564	Approved
0.6885	Remote Similarity	NPD3495	Discontinued
0.6885	Remote Similarity	NPD1566	Phase 3
0.6884	Remote Similarity	NPD6696	Suspended
0.6879	Remote Similarity	NPD4625	Phase 3
0.6879	Remote Similarity	NPD6966	Discovery
0.687	Remote Similarity	NPD1398	Phase 1
0.6866	Remote Similarity	NPD1759	Phase 1
0.686	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4208	Discontinued
0.6855	Remote Similarity	NPD6959	Discontinued
0.6853	Remote Similarity	NPD1240	Approved
0.6846	Remote Similarity	NPD2309	Approved
0.6846	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD37	Approved
0.6838	Remote Similarity	NPD1087	Approved
0.6838	Remote Similarity	NPD3496	Discontinued
0.6835	Remote Similarity	NPD3094	Phase 2
0.6835	Remote Similarity	NPD3266	Approved
0.6835	Remote Similarity	NPD3267	Approved
0.6831	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7985	Registered
0.6822	Remote Similarity	NPD1317	Discontinued
0.6821	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5585	Approved
0.6815	Remote Similarity	NPD7768	Phase 2
0.6815	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4093	Discontinued

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