NPASS Compound

Structure

CID139712 OpenBabel06191715492D 23 23 0 0 1 0 0 0 0 0999 V2000 -8.6603 0.0000 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -5.1962 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 5 22 1 0 0 0 0 6 8 2 0 0 0 0 8 9 1 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 3 1 6 0 0 0 13 19 1 0 0 0 0 14 4 1 1 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 7 1 1 0 0 0 15 17 1 0 0 0 0 16 20 1 1 0 0 0 17 12 1 1 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.23
Volume:	355.875
LogP:	3.653
LogD:	3.562
LogS:	-3.644
# Rotatable Bonds:	9
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.521
Synthetic Accessibility Score:	4.73
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.527
MDCK Permeability:	3.9385722629958764e-05
Pgp-inhibitor:	0.236
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.686
20% Bioavailability (F20%):	0.462
30% Bioavailability (F30%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.238
Plasma Protein Binding (PPB):	98.10089111328125%
Volume Distribution (VD):	1.127
Pgp-substrate:	2.2511768341064453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.768
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.237
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.754
CYP3A4-substrate:	0.373

ADMET: Excretion

Clearance (CL):	7.505
Half-life (T1/2):	0.479

ADMET: Toxicity

hERG Blockers:	0.165
Human Hepatotoxicity (H-HT):	0.445
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.557
Skin Sensitization:	0.938
Carcinogencity:	0.086
Eye Corrosion:	0.064
Eye Irritation:	0.538
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC139712

Natural Product ID:	NPC139712
*Common Name:**	Pironetin
IUPAC Name:	(2R,3R)-3-ethyl-2-[(E,2R,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethylnon-7-enyl]-2,3-dihydropyran-6-one
Synonyms:	Pironetin
Standard InCHIKey:	XIHGDBYGUWEHCV-FSEPSNHWSA-N
Standard InCHI:	InChI=1S/C19H32O4/c1-6-8-9-13(3)19(22-5)14(4)16(20)12-17-15(7-2)10-11-18(21)23-17/h6,8,10-11,13-17,19-20H,7,9,12H2,1-5H3/b8-6+/t13-,14-,15+,16+,17+,19+/m0/s1
SMILES:	C/C=C/C[C@@H]([C@H]([C@H]([C@@H](C[C@H]1OC(=O)C=C[C@H]1CC)O)C)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1779811
PubChem CID:	6438891
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty 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
NPO40549	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30601004]

☑ 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
GI50	20
IC50	14
Others	34

Activity Type	# Activity
Cell Line	33
CELL-LINE	1
NON-MOLECULAR	2
Organism	1
Others	27
Protein Complex	1
PROTEIN FAMILY	24

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	2.9	nM	PMID[569865]
NPT179	Cell Line	A2780	Homo sapiens	Ratio IC50	=	1.0	n.a.	PMID[569865]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6.0	nM	PMID[569866]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	6.4	nM	PMID[569866]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	17.0	nM	PMID[569866]
NPT71	Cell Line	HEK293	Homo sapiens	Ratio IC50	=	2.6	n.a.	PMID[569866]
NPT71	Cell Line	HEK293	Homo sapiens	Ratio IC50	=	2.8	n.a.	PMID[569866]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	6.4	nM	PMID[569867]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6.0	nM	PMID[569867]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	17.0	nM	PMID[569867]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	8.0	nM	PMID[569867]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	50.0	%	PMID[569868]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	48.0	%	PMID[569868]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	119.0	%	PMID[569868]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	118.0	%	PMID[569868]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	<	15.0	nM	PMID[569871]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	92.0	nM	PMID[569871]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15.0	nM	PMID[569871]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	7.5	nM	PMID[569872]
NPT1396	Cell Line	NCI-H69	Homo sapiens	GI50	=	17.5	nM	PMID[569872]
NPT4590	Cell Line	EL4	Mus musculus	GI50	=	15.0	nM	PMID[569872]
NPT2786	Cell Line	DC3F	Cricetulus griseus	GI50	=	9.5	nM	PMID[569872]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	30.0	nM	PMID[569872]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	20.0	nM	PMID[569872]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	17.3	nM	PMID[569872]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	5.0	nM	PMID[569872]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	4.6	nM	PMID[569872]
NPT168	Cell Line	P388	Mus musculus	GI50	=	100.0	nM	PMID[569872]
NPT1125	Cell Line	T98G	Homo sapiens	GI50	=	7.5	nM	PMID[569872]
NPT168	Cell Line	P388	Mus musculus	MST	=	11.2	day	PMID[569872]
NPT168	Cell Line	P388	Mus musculus	MST	=	11.7	day	PMID[569872]
NPT168	Cell Line	P388	Mus musculus	MST	=	13.3	day	PMID[569872]
NPT168	Cell Line	P388	Mus musculus	MST	=	14.3	day	PMID[569872]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.0	nM	PMID[569865]
NPT2	Others	Unspecified		Activity	>	15.0	uM	PMID[569865]
NPT2	Others	Unspecified		Activity	=	23.4	uM	PMID[569865]
NPT518	Protein Complex	Tubulin	Homo sapiens	Activity	>	15.0	uM	PMID[569867]
NPT27	Others	Unspecified		Ratio IC50	=	2.8	n.a.	PMID[569867]
NPT27	Others	Unspecified		Ratio IC50	=	2.6	n.a.	PMID[569867]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25.0	nM	PMID[569867]
NPT2	Others	Unspecified		Ratio IC50	=	3.0	n.a.	PMID[569867]
NPT2	Others	Unspecified		GI50	=	14.4	nM	PMID[569869]
NPT2	Others	Unspecified		GI50	=	24.3	nM	PMID[569869]
NPT2	Others	Unspecified		Activity	=	10.0	%	PMID[569869]
NPT27	Others	Unspecified		Stability	=	50.0	%	PMID[569870]
NPT27	Others	Unspecified		Stability	=	35.0	%	PMID[569870]
NPT27	Others	Unspecified		Stability	=	56.0	%	PMID[569870]
NPT27	Others	Unspecified		T1/2	=	0.1167	hr	PMID[569870]
NPT27	Others	Unspecified		T1/2	<	0.25	hr	PMID[569870]
NPT27	Others	Unspecified		PPB	=	87.0	%	PMID[569870]
NPT27	Others	Unspecified		PPB	=	98.0	%	PMID[569870]
NPT27	Others	Unspecified		PPB	=	93.0	%	PMID[569870]
NPT27	Others	Unspecified		Drug metabolism	=	62.0	%	PMID[569870]
NPT27	Others	Unspecified		Drug metabolism	=	57.0	%	PMID[569870]
NPT23816	PROTEIN FAMILY	Tubulin alpha	Homo sapiens	IC50	=	26.0	nM	PMID[569870]
NPT23816	PROTEIN FAMILY	Tubulin alpha	Homo sapiens	GI50	=	22.2	nM	PMID[569870]
NPT23816	PROTEIN FAMILY	Tubulin alpha	Homo sapiens	GI50	=	22.3	nM	PMID[569870]
NPT2	Others	Unspecified		GI50	=	11.5	nM	PMID[569872]
NPT2	Others	Unspecified		GI50	=	20.3	nM	PMID[569872]
NPT2	Others	Unspecified		GI50	=	30.0	nM	PMID[569872]
NPT23299	CELL-LINE	K562/Adr	Homo sapiens	GI50	=	16.0	nM	PMID[569872]
NPT2	Others	Unspecified		GI50	=	31.0	nM	PMID[569872]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	7.4	%	PMID[569872]
NPT27	Others	Unspecified		Activity	=	3.7	g	PMID[569872]
NPT27	Others	Unspecified		Activity	=	0.5	g	PMID[569872]
NPT27	Others	Unspecified		Activity	=	-0.1	g	PMID[569872]
NPT27	Others	Unspecified		Activity	=	-2.6	g	PMID[569872]

☑ 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 NPC139712 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	170
0.1-0.2	1210
0.2-0.3	4819
0.3-0.4	12050
0.4-0.5	13438
0.5-0.6	6958
0.6-0.7	3429
0.7-0.8	546
0.8-0.85	58
0.85-0.9	13
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC8538
0.9221	High Similarity	NPC184208
0.9178	High Similarity	NPC185186
0.9178	High Similarity	NPC327383
0.8974	High Similarity	NPC315731
0.8933	High Similarity	NPC327041
0.8933	High Similarity	NPC285840
0.8816	High Similarity	NPC469880
0.8795	High Similarity	NPC133450
0.878	High Similarity	NPC199382
0.869	High Similarity	NPC3952
0.869	High Similarity	NPC177668
0.8667	High Similarity	NPC477085
0.8667	High Similarity	NPC329914
0.859	High Similarity	NPC248775
0.8588	High Similarity	NPC206679
0.8588	High Similarity	NPC114172
0.8588	High Similarity	NPC476075
0.8588	High Similarity	NPC476084
0.8588	High Similarity	NPC471324
0.8554	High Similarity	NPC316138
0.8554	High Similarity	NPC313658
0.8537	High Similarity	NPC471494
0.8533	High Similarity	NPC477087
0.8533	High Similarity	NPC477086
0.8514	High Similarity	NPC101622
0.8488	Intermediate Similarity	NPC159092
0.8488	Intermediate Similarity	NPC109406
0.8481	Intermediate Similarity	NPC180725
0.8481	Intermediate Similarity	NPC470149
0.8481	Intermediate Similarity	NPC470148
0.8462	Intermediate Similarity	NPC474026
0.8462	Intermediate Similarity	NPC477203
0.8462	Intermediate Similarity	NPC84360
0.8434	Intermediate Similarity	NPC47220
0.8434	Intermediate Similarity	NPC186332
0.8421	Intermediate Similarity	NPC329890
0.8415	Intermediate Similarity	NPC160517
0.8415	Intermediate Similarity	NPC186155
0.8415	Intermediate Similarity	NPC78673
0.84	Intermediate Similarity	NPC476012
0.84	Intermediate Similarity	NPC4299
0.8391	Intermediate Similarity	NPC256368
0.8375	Intermediate Similarity	NPC133226
0.8375	Intermediate Similarity	NPC470147
0.8333	Intermediate Similarity	NPC188860
0.8333	Intermediate Similarity	NPC477202
0.8267	Intermediate Similarity	NPC151481
0.825	Intermediate Similarity	NPC477088
0.825	Intermediate Similarity	NPC55304
0.825	Intermediate Similarity	NPC226226
0.8228	Intermediate Similarity	NPC233071
0.8228	Intermediate Similarity	NPC475711
0.8214	Intermediate Similarity	NPC61527
0.8214	Intermediate Similarity	NPC311163
0.8158	Intermediate Similarity	NPC476037
0.8111	Intermediate Similarity	NPC475332
0.8095	Intermediate Similarity	NPC242233
0.809	Intermediate Similarity	NPC300710
0.8072	Intermediate Similarity	NPC474809
0.8072	Intermediate Similarity	NPC16488
0.8072	Intermediate Similarity	NPC44261
0.8068	Intermediate Similarity	NPC238090
0.8068	Intermediate Similarity	NPC472196
0.8068	Intermediate Similarity	NPC472195
0.8052	Intermediate Similarity	NPC316185
0.8052	Intermediate Similarity	NPC477084
0.8052	Intermediate Similarity	NPC475762
0.8049	Intermediate Similarity	NPC475944
0.8049	Intermediate Similarity	NPC112868
0.8025	Intermediate Similarity	NPC86971
0.8	Intermediate Similarity	NPC288350
0.8	Intermediate Similarity	NPC315394
0.8	Intermediate Similarity	NPC255410
0.8	Intermediate Similarity	NPC173329
0.7978	Intermediate Similarity	NPC469491
0.7978	Intermediate Similarity	NPC159698
0.7976	Intermediate Similarity	NPC266718
0.7952	Intermediate Similarity	NPC10080
0.7952	Intermediate Similarity	NPC123908
0.7922	Intermediate Similarity	NPC469660
0.7912	Intermediate Similarity	NPC120299
0.7901	Intermediate Similarity	NPC209135
0.7901	Intermediate Similarity	NPC474816
0.7882	Intermediate Similarity	NPC67081
0.7882	Intermediate Similarity	NPC471223
0.7865	Intermediate Similarity	NPC476049
0.7857	Intermediate Similarity	NPC106912
0.7857	Intermediate Similarity	NPC27314
0.7857	Intermediate Similarity	NPC31019
0.7857	Intermediate Similarity	NPC2379
0.7857	Intermediate Similarity	NPC263087
0.7848	Intermediate Similarity	NPC107654
0.7848	Intermediate Similarity	NPC477204
0.7848	Intermediate Similarity	NPC315843
0.7841	Intermediate Similarity	NPC473448
0.7841	Intermediate Similarity	NPC475855
0.7826	Intermediate Similarity	NPC475653
0.7821	Intermediate Similarity	NPC472254
0.7805	Intermediate Similarity	NPC321728
0.7805	Intermediate Similarity	NPC471537
0.7805	Intermediate Similarity	NPC1180
0.7802	Intermediate Similarity	NPC472995
0.7792	Intermediate Similarity	NPC269841
0.7791	Intermediate Similarity	NPC316426
0.7791	Intermediate Similarity	NPC164393
0.7791	Intermediate Similarity	NPC315395
0.7778	Intermediate Similarity	NPC262747
0.7763	Intermediate Similarity	NPC472266
0.7727	Intermediate Similarity	NPC295312
0.7717	Intermediate Similarity	NPC40812
0.7701	Intermediate Similarity	NPC471055
0.7701	Intermediate Similarity	NPC160138
0.7701	Intermediate Similarity	NPC471056
0.7701	Intermediate Similarity	NPC471796
0.7692	Intermediate Similarity	NPC304886
0.7692	Intermediate Similarity	NPC272050
0.7684	Intermediate Similarity	NPC197736
0.7683	Intermediate Similarity	NPC326753
0.7674	Intermediate Similarity	NPC137033
0.7674	Intermediate Similarity	NPC11804
0.7667	Intermediate Similarity	NPC475838
0.7667	Intermediate Similarity	NPC125674
0.7667	Intermediate Similarity	NPC228451
0.7662	Intermediate Similarity	NPC475760
0.766	Intermediate Similarity	NPC471637
0.766	Intermediate Similarity	NPC57586
0.766	Intermediate Similarity	NPC2313
0.766	Intermediate Similarity	NPC475655
0.766	Intermediate Similarity	NPC475157
0.766	Intermediate Similarity	NPC154132
0.7654	Intermediate Similarity	NPC256720
0.7654	Intermediate Similarity	NPC236228
0.7647	Intermediate Similarity	NPC161045
0.7647	Intermediate Similarity	NPC11620
0.7647	Intermediate Similarity	NPC23748
0.7647	Intermediate Similarity	NPC116543
0.7647	Intermediate Similarity	NPC250315
0.7647	Intermediate Similarity	NPC231601
0.764	Intermediate Similarity	NPC476004
0.764	Intermediate Similarity	NPC474761
0.764	Intermediate Similarity	NPC179394
0.764	Intermediate Similarity	NPC144133
0.764	Intermediate Similarity	NPC202886
0.7634	Intermediate Similarity	NPC261377
0.7634	Intermediate Similarity	NPC255592
0.7634	Intermediate Similarity	NPC83895
0.7634	Intermediate Similarity	NPC203627
0.7634	Intermediate Similarity	NPC65700
0.7634	Intermediate Similarity	NPC187761
0.7634	Intermediate Similarity	NPC308567
0.7632	Intermediate Similarity	NPC146811
0.7619	Intermediate Similarity	NPC473339
0.7619	Intermediate Similarity	NPC469469
0.7619	Intermediate Similarity	NPC474894
0.7619	Intermediate Similarity	NPC471552
0.7614	Intermediate Similarity	NPC227379
0.7614	Intermediate Similarity	NPC474471
0.7609	Intermediate Similarity	NPC473291
0.7586	Intermediate Similarity	NPC305475
0.7586	Intermediate Similarity	NPC208473
0.7586	Intermediate Similarity	NPC122502
0.7586	Intermediate Similarity	NPC475461
0.7582	Intermediate Similarity	NPC474247
0.7579	Intermediate Similarity	NPC473596
0.7579	Intermediate Similarity	NPC201191
0.7558	Intermediate Similarity	NPC474251
0.7558	Intermediate Similarity	NPC474865
0.7558	Intermediate Similarity	NPC126518
0.7558	Intermediate Similarity	NPC474776
0.7556	Intermediate Similarity	NPC158061
0.7556	Intermediate Similarity	NPC30515
0.7556	Intermediate Similarity	NPC477749
0.7556	Intermediate Similarity	NPC184463
0.7553	Intermediate Similarity	NPC475053
0.7534	Intermediate Similarity	NPC22897
0.7534	Intermediate Similarity	NPC159650
0.7531	Intermediate Similarity	NPC329852
0.7529	Intermediate Similarity	NPC224455
0.7529	Intermediate Similarity	NPC471298
0.7529	Intermediate Similarity	NPC323251
0.7528	Intermediate Similarity	NPC477748
0.7528	Intermediate Similarity	NPC474032
0.7528	Intermediate Similarity	NPC261320
0.7528	Intermediate Similarity	NPC212598
0.75	Intermediate Similarity	NPC469583
0.75	Intermediate Similarity	NPC248602
0.75	Intermediate Similarity	NPC16349
0.75	Intermediate Similarity	NPC477959
0.75	Intermediate Similarity	NPC86005
0.75	Intermediate Similarity	NPC96414
0.75	Intermediate Similarity	NPC36954
0.75	Intermediate Similarity	NPC474739
0.75	Intermediate Similarity	NPC276110
0.75	Intermediate Similarity	NPC222244
0.7473	Intermediate Similarity	NPC162615
0.7473	Intermediate Similarity	NPC476300
0.7473	Intermediate Similarity	NPC475912
0.7473	Intermediate Similarity	NPC152778
0.7473	Intermediate Similarity	NPC205034

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 NPC139712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1684
0.2-0.3	3781
0.3-0.4	2432
0.4-0.5	785
0.5-0.6	246
0.6-0.7	63
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
0.8256	Intermediate Similarity	NPD7838	Discovery
0.8046	Intermediate Similarity	NPD6698	Approved
0.8046	Intermediate Similarity	NPD46	Approved
0.766	Intermediate Similarity	NPD5344	Discontinued
0.7634	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6648	Approved
0.7303	Intermediate Similarity	NPD4250	Approved
0.7303	Intermediate Similarity	NPD4251	Approved
0.7294	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5785	Approved
0.7241	Intermediate Similarity	NPD7154	Phase 3
0.7191	Intermediate Similarity	NPD4249	Approved
0.7174	Intermediate Similarity	NPD7983	Approved
0.7097	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD5779	Approved
0.7093	Intermediate Similarity	NPD4821	Approved
0.7093	Intermediate Similarity	NPD4820	Approved
0.7093	Intermediate Similarity	NPD4819	Approved
0.7093	Intermediate Similarity	NPD4822	Approved
0.7083	Intermediate Similarity	NPD7638	Approved
0.7079	Intermediate Similarity	NPD5363	Approved
0.7059	Intermediate Similarity	NPD4268	Approved
0.7059	Intermediate Similarity	NPD4271	Approved
0.701	Intermediate Similarity	NPD7640	Approved
0.701	Intermediate Similarity	NPD7639	Approved
0.6989	Remote Similarity	NPD7637	Suspended
0.6907	Remote Similarity	NPD4225	Approved
0.6889	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7839	Suspended
0.6863	Remote Similarity	NPD6686	Approved
0.6854	Remote Similarity	NPD5362	Discontinued
0.6771	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6053	Discontinued
0.6742	Remote Similarity	NPD6435	Approved
0.6742	Remote Similarity	NPD4270	Approved
0.6742	Remote Similarity	NPD4269	Approved
0.6731	Remote Similarity	NPD6371	Approved
0.6703	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5786	Approved
0.6629	Remote Similarity	NPD5369	Approved
0.6629	Remote Similarity	NPD4790	Discontinued
0.6596	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6101	Approved
0.6556	Remote Similarity	NPD5209	Approved
0.6556	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4252	Approved
0.6517	Remote Similarity	NPD5368	Approved
0.6512	Remote Similarity	NPD8039	Approved
0.65	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6695	Phase 3
0.6463	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6411	Approved
0.6429	Remote Similarity	NPD7503	Approved
0.6421	Remote Similarity	NPD1695	Approved
0.6413	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD7115	Discovery
0.6346	Remote Similarity	NPD4211	Phase 1
0.6344	Remote Similarity	NPD1694	Approved
0.6333	Remote Similarity	NPD7332	Phase 2
0.6333	Remote Similarity	NPD7514	Phase 3
0.6329	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5282	Discontinued
0.6316	Remote Similarity	NPD7829	Approved
0.6316	Remote Similarity	NPD7830	Approved
0.6304	Remote Similarity	NPD6110	Phase 1
0.6292	Remote Similarity	NPD7145	Approved
0.6289	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD5370	Suspended
0.6222	Remote Similarity	NPD6929	Approved
0.6211	Remote Similarity	NPD7524	Approved
0.6211	Remote Similarity	NPD7750	Discontinued
0.618	Remote Similarity	NPD6925	Approved
0.618	Remote Similarity	NPD4756	Discovery
0.618	Remote Similarity	NPD6932	Approved
0.618	Remote Similarity	NPD5776	Phase 2
0.6174	Remote Similarity	NPD7642	Approved
0.6161	Remote Similarity	NPD7328	Approved
0.6161	Remote Similarity	NPD7327	Approved
0.6154	Remote Similarity	NPD6647	Phase 2
0.6154	Remote Similarity	NPD6931	Approved
0.6154	Remote Similarity	NPD6930	Phase 2
0.614	Remote Similarity	NPD8033	Approved
0.614	Remote Similarity	NPD8513	Phase 3
0.6136	Remote Similarity	NPD8264	Approved
0.6106	Remote Similarity	NPD7516	Approved
0.6098	Remote Similarity	NPD3197	Phase 1
0.6092	Remote Similarity	NPD4732	Discontinued
0.6082	Remote Similarity	NPD6051	Approved
0.6071	Remote Similarity	NPD7505	Discontinued
0.6053	Remote Similarity	NPD8377	Approved
0.6053	Remote Similarity	NPD8294	Approved
0.6049	Remote Similarity	NPD4193	Approved
0.6049	Remote Similarity	NPD4192	Approved
0.6049	Remote Similarity	NPD4194	Approved
0.6049	Remote Similarity	NPD368	Approved
0.6049	Remote Similarity	NPD4191	Approved
0.6019	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD7641	Discontinued
0.6	Remote Similarity	NPD8296	Approved
0.6	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8379	Approved
0.6	Remote Similarity	NPD8335	Approved
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD8380	Approved
0.6	Remote Similarity	NPD7748	Approved
0.598	Remote Similarity	NPD6083	Phase 2
0.598	Remote Similarity	NPD6084	Phase 2
0.5978	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6421	Discontinued
0.596	Remote Similarity	NPD7087	Discontinued
0.596	Remote Similarity	NPD7515	Phase 2
0.5952	Remote Similarity	NPD7331	Phase 2
0.5938	Remote Similarity	NPD6422	Discontinued
0.5934	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7500	Approved
0.5926	Remote Similarity	NPD6881	Approved
0.5926	Remote Similarity	NPD6899	Approved
0.5914	Remote Similarity	NPD6898	Phase 1
0.5909	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6399	Phase 3
0.5897	Remote Similarity	NPD342	Phase 1
0.587	Remote Similarity	NPD6683	Phase 2
0.5862	Remote Similarity	NPD7143	Approved
0.5862	Remote Similarity	NPD7144	Approved
0.5843	Remote Similarity	NPD6924	Approved
0.5843	Remote Similarity	NPD6926	Approved
0.5833	Remote Similarity	NPD6685	Approved
0.5833	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD6412	Phase 2
0.5833	Remote Similarity	NPD6893	Approved
0.5825	Remote Similarity	NPD7902	Approved
0.5818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7102	Approved
0.5818	Remote Similarity	NPD7290	Approved
0.5818	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD8451	Approved
0.5798	Remote Similarity	NPD7507	Approved
0.5798	Remote Similarity	NPD8273	Phase 1
0.5795	Remote Similarity	NPD7152	Approved
0.5795	Remote Similarity	NPD7150	Approved
0.5795	Remote Similarity	NPD7151	Approved
0.5789	Remote Similarity	NPD6927	Phase 3
0.5784	Remote Similarity	NPD5695	Phase 3
0.578	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6684	Approved
0.5773	Remote Similarity	NPD7334	Approved
0.5773	Remote Similarity	NPD7521	Approved
0.5773	Remote Similarity	NPD7146	Approved
0.5773	Remote Similarity	NPD5330	Approved
0.5773	Remote Similarity	NPD6409	Approved
0.5769	Remote Similarity	NPD3196	Approved
0.5769	Remote Similarity	NPD3195	Phase 2
0.5769	Remote Similarity	NPD4266	Approved
0.5769	Remote Similarity	NPD3194	Approved
0.5766	Remote Similarity	NPD6869	Approved
0.5766	Remote Similarity	NPD6847	Approved
0.5766	Remote Similarity	NPD6650	Approved
0.5766	Remote Similarity	NPD6649	Approved
0.5766	Remote Similarity	NPD6617	Approved
0.5766	Remote Similarity	NPD8130	Phase 1
0.5761	Remote Similarity	NPD3732	Approved
0.575	Remote Similarity	NPD8074	Phase 3
0.575	Remote Similarity	NPD8448	Approved
0.5747	Remote Similarity	NPD6923	Approved
0.5747	Remote Similarity	NPD6922	Approved
0.5741	Remote Similarity	NPD6402	Approved
0.5741	Remote Similarity	NPD6675	Approved
0.5741	Remote Similarity	NPD5739	Approved
0.5741	Remote Similarity	NPD6640	Phase 3
0.5741	Remote Similarity	NPD5048	Discontinued
0.5741	Remote Similarity	NPD7128	Approved
0.5729	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6014	Approved
0.5727	Remote Similarity	NPD6013	Approved
0.5727	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6933	Approved
0.5714	Remote Similarity	NPD6882	Approved
0.5714	Remote Similarity	NPD8297	Approved
0.57	Remote Similarity	NPD7136	Phase 2
0.57	Remote Similarity	NPD3168	Discontinued
0.5699	Remote Similarity	NPD7645	Phase 2
0.5691	Remote Similarity	NPD7260	Phase 2
0.5679	Remote Similarity	NPD6109	Phase 1
0.5679	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD4632	Approved
0.5657	Remote Similarity	NPD6903	Approved
0.5657	Remote Similarity	NPD6672	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