NPASS Compound

Structure

CID151516 OpenBabel06191715522D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.3286 -0.5790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1270 0.1270 0.0000 C 0 0 0 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 -4.5759 -0.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3349 -0.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5329 0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9805 -1.3419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3785 -2.2592 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7831 -3.0626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7896 -2.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3915 -2.0313 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5694 -0.6524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2247 1.2247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4210 1.3286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3720 -2.3732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1811 -3.9800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1942 -3.7521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9870 -1.2279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3981 -1.9174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 15 1 0 0 0 0 3 7 2 0 0 0 0 3 9 1 0 0 0 0 4 8 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 15 1 0 0 0 0 6 18 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 1 0 0 0 9 19 2 0 0 0 0 10 5 1 1 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 6 0 0 0 12 13 1 0 0 0 0 12 21 1 1 0 0 0 13 14 1 0 0 0 0 13 22 1 6 0 0 0 14 23 1 0 0 0 0 14 24 1 1 0 0 0 15 16 1 1 0 0 0 16 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.15
Volume:	324.672
LogP:	-1.026
LogD:	-0.864
LogS:	-1.618
# Rotatable Bonds:	4
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	5.606
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-6.061
MDCK Permeability:	0.00013511600263882428
Pgp-inhibitor:	0.007
Pgp-substrate:	0.802
Human Intestinal Absorption (HIA):	0.825
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.839

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.229
Plasma Protein Binding (PPB):	28.516048431396484%
Volume Distribution (VD):	0.37
Pgp-substrate:	51.845272064208984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.866
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.813
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	1.714
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.242
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.427
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.882
Carcinogencity:	0.469
Eye Corrosion:	0.003
Eye Irritation:	0.064
Respiratory Toxicity:	0.264

Download Data

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

Natural Product: NPC151516

Natural Product ID:	NPC151516
*Common Name:**	Moudanpioside F
IUPAC Name:	(1R,5S,6R)-6-(hydroxymethyl)-4,6-dimethyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybicyclo[3.1.1]hept-3-en-2-one
Synonyms:	Moudanpioside F
Standard InCHIKey:	HDRABVWFLVVWRI-VCRUDBCKSA-N
Standard InCHI:	InChI=1S/C16H24O8/c1-7-3-9(19)8-4-16(7,15(8,2)6-18)24-14-13(22)12(21)11(20)10(5-17)23-14/h3,8,10-14,17-18,20-22H,4-6H2,1-2H3/t8-,10+,11+,12-,13+,14-,15-,16-/m0/s1
SMILES:	CC1=CC(=O)[C@@H]2C[C@]1([C@@]2(C)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2205293
PubChem CID:	21631108
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	12410.0	nM	PMID[453291]

☑ 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 NPC151516 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	223
0.1-0.2	1408
0.2-0.3	4911
0.3-0.4	9534
0.4-0.5	13283
0.5-0.6	7869
0.6-0.7	5037
0.7-0.8	406
0.8-0.85	14
0.85-0.9	11
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9175	High Similarity	NPC307517
0.9175	High Similarity	NPC169468
0.9175	High Similarity	NPC81483
0.9175	High Similarity	NPC61630
0.8958	High Similarity	NPC2003
0.8958	High Similarity	NPC25701
0.89	High Similarity	NPC223834
0.8878	High Similarity	NPC474194
0.88	High Similarity	NPC154127
0.8788	High Similarity	NPC198422
0.8788	High Similarity	NPC40182
0.8485	Intermediate Similarity	NPC108141
0.8476	Intermediate Similarity	NPC473288
0.8416	Intermediate Similarity	NPC70733
0.8416	Intermediate Similarity	NPC56071
0.84	Intermediate Similarity	NPC256230
0.8182	Intermediate Similarity	NPC477749
0.8163	Intermediate Similarity	NPC477748
0.8148	Intermediate Similarity	NPC235014
0.8148	Intermediate Similarity	NPC83005
0.8142	Intermediate Similarity	NPC48692
0.8131	Intermediate Similarity	NPC392
0.8131	Intermediate Similarity	NPC177524
0.8131	Intermediate Similarity	NPC219900
0.8091	Intermediate Similarity	NPC75167
0.8091	Intermediate Similarity	NPC311592
0.8081	Intermediate Similarity	NPC202886
0.8077	Intermediate Similarity	NPC280991
0.8061	Intermediate Similarity	NPC471755
0.8061	Intermediate Similarity	NPC471756
0.8039	Intermediate Similarity	NPC143446
0.8018	Intermediate Similarity	NPC181145
0.7982	Intermediate Similarity	NPC46407
0.7965	Intermediate Similarity	NPC45475
0.7965	Intermediate Similarity	NPC234522
0.7963	Intermediate Similarity	NPC272576
0.7961	Intermediate Similarity	NPC125551
0.7961	Intermediate Similarity	NPC309503
0.7961	Intermediate Similarity	NPC278506
0.7961	Intermediate Similarity	NPC96597
0.7961	Intermediate Similarity	NPC91197
0.7961	Intermediate Similarity	NPC155319
0.7961	Intermediate Similarity	NPC239547
0.7921	Intermediate Similarity	NPC67398
0.7921	Intermediate Similarity	NPC474792
0.7921	Intermediate Similarity	NPC91654
0.7905	Intermediate Similarity	NPC198992
0.7879	Intermediate Similarity	NPC248312
0.7876	Intermediate Similarity	NPC474483
0.787	Intermediate Similarity	NPC293512
0.7864	Intermediate Similarity	NPC54731
0.7857	Intermediate Similarity	NPC475163
0.7845	Intermediate Similarity	NPC28532
0.7838	Intermediate Similarity	NPC471967
0.7838	Intermediate Similarity	NPC174836
0.783	Intermediate Similarity	NPC121423
0.783	Intermediate Similarity	NPC201191
0.7826	Intermediate Similarity	NPC473130
0.7822	Intermediate Similarity	NPC302584
0.7818	Intermediate Similarity	NPC52241
0.7818	Intermediate Similarity	NPC475317
0.7818	Intermediate Similarity	NPC154856
0.7818	Intermediate Similarity	NPC119550
0.7807	Intermediate Similarity	NPC473828
0.7807	Intermediate Similarity	NPC473617
0.7798	Intermediate Similarity	NPC48548
0.7798	Intermediate Similarity	NPC135015
0.7798	Intermediate Similarity	NPC217921
0.7798	Intermediate Similarity	NPC128795
0.7797	Intermediate Similarity	NPC222307
0.7788	Intermediate Similarity	NPC471816
0.7778	Intermediate Similarity	NPC82251
0.7778	Intermediate Similarity	NPC239961
0.7768	Intermediate Similarity	NPC293658
0.7768	Intermediate Similarity	NPC477944
0.7768	Intermediate Similarity	NPC62696
0.7768	Intermediate Similarity	NPC260665
0.7768	Intermediate Similarity	NPC264153
0.7768	Intermediate Similarity	NPC474410
0.7768	Intermediate Similarity	NPC293038
0.7768	Intermediate Similarity	NPC473159
0.7759	Intermediate Similarity	NPC170084
0.7759	Intermediate Similarity	NPC476204
0.7755	Intermediate Similarity	NPC477747
0.7755	Intermediate Similarity	NPC477746
0.775	Intermediate Similarity	NPC476966
0.775	Intermediate Similarity	NPC471407
0.7745	Intermediate Similarity	NPC320089
0.7739	Intermediate Similarity	NPC477071
0.7731	Intermediate Similarity	NPC470516
0.7727	Intermediate Similarity	NPC40728
0.7727	Intermediate Similarity	NPC246205
0.7727	Intermediate Similarity	NPC316974
0.7719	Intermediate Similarity	NPC23046
0.7719	Intermediate Similarity	NPC473405
0.7714	Intermediate Similarity	NPC222303
0.7714	Intermediate Similarity	NPC472015
0.7706	Intermediate Similarity	NPC88013
0.7706	Intermediate Similarity	NPC143609
0.7706	Intermediate Similarity	NPC184512
0.7706	Intermediate Similarity	NPC125423
0.7699	Intermediate Similarity	NPC102088
0.7699	Intermediate Similarity	NPC74727
0.7692	Intermediate Similarity	NPC306041
0.7692	Intermediate Similarity	NPC90583
0.7685	Intermediate Similarity	NPC194941
0.7685	Intermediate Similarity	NPC470104
0.7685	Intermediate Similarity	NPC121566
0.7685	Intermediate Similarity	NPC100955
0.7685	Intermediate Similarity	NPC296950
0.7685	Intermediate Similarity	NPC146731
0.7679	Intermediate Similarity	NPC46388
0.7679	Intermediate Similarity	NPC37739
0.7679	Intermediate Similarity	NPC130427
0.7679	Intermediate Similarity	NPC474265
0.7679	Intermediate Similarity	NPC210420
0.7672	Intermediate Similarity	NPC476127
0.7672	Intermediate Similarity	NPC470312
0.7672	Intermediate Similarity	NPC476150
0.767	Intermediate Similarity	NPC294293
0.7667	Intermediate Similarity	NPC220838
0.7667	Intermediate Similarity	NPC311534
0.7667	Intermediate Similarity	NPC270109
0.7667	Intermediate Similarity	NPC45606
0.7664	Intermediate Similarity	NPC214277
0.7664	Intermediate Similarity	NPC476235
0.7664	Intermediate Similarity	NPC150463
0.7664	Intermediate Similarity	NPC476126
0.7658	Intermediate Similarity	NPC5103
0.7652	Intermediate Similarity	NPC471548
0.7652	Intermediate Similarity	NPC291564
0.7647	Intermediate Similarity	NPC472197
0.7647	Intermediate Similarity	NPC297950
0.7647	Intermediate Similarity	NPC324157
0.7636	Intermediate Similarity	NPC151393
0.7636	Intermediate Similarity	NPC472439
0.7636	Intermediate Similarity	NPC311223
0.7636	Intermediate Similarity	NPC469916
0.7632	Intermediate Similarity	NPC207637
0.7627	Intermediate Similarity	NPC27363
0.7627	Intermediate Similarity	NPC41129
0.7624	Intermediate Similarity	NPC309310
0.7623	Intermediate Similarity	NPC471855
0.7623	Intermediate Similarity	NPC231240
0.7619	Intermediate Similarity	NPC266842
0.7615	Intermediate Similarity	NPC63023
0.7615	Intermediate Similarity	NPC111952
0.7615	Intermediate Similarity	NPC252296
0.7615	Intermediate Similarity	NPC95243
0.7611	Intermediate Similarity	NPC471204
0.7611	Intermediate Similarity	NPC47063
0.7611	Intermediate Similarity	NPC204458
0.7611	Intermediate Similarity	NPC269315
0.7611	Intermediate Similarity	NPC138334
0.7611	Intermediate Similarity	NPC189884
0.7611	Intermediate Similarity	NPC271138
0.7607	Intermediate Similarity	NPC202051
0.7596	Intermediate Similarity	NPC473369
0.7593	Intermediate Similarity	NPC7613
0.7593	Intermediate Similarity	NPC475889
0.7593	Intermediate Similarity	NPC473124
0.7593	Intermediate Similarity	NPC7644
0.7593	Intermediate Similarity	NPC127933
0.7593	Intermediate Similarity	NPC473123
0.7593	Intermediate Similarity	NPC99266
0.7593	Intermediate Similarity	NPC8196
0.7593	Intermediate Similarity	NPC473070
0.7589	Intermediate Similarity	NPC191763
0.7586	Intermediate Similarity	NPC474179
0.7586	Intermediate Similarity	NPC122971
0.7586	Intermediate Similarity	NPC475775
0.7586	Intermediate Similarity	NPC475834
0.7586	Intermediate Similarity	NPC476529
0.7576	Intermediate Similarity	NPC34581
0.7573	Intermediate Similarity	NPC472196
0.7573	Intermediate Similarity	NPC238090
0.7573	Intermediate Similarity	NPC472195
0.757	Intermediate Similarity	NPC477870
0.757	Intermediate Similarity	NPC476246
0.757	Intermediate Similarity	NPC476213
0.757	Intermediate Similarity	NPC477871
0.7568	Intermediate Similarity	NPC57362
0.7568	Intermediate Similarity	NPC206618
0.7568	Intermediate Similarity	NPC204407
0.7568	Intermediate Similarity	NPC167383
0.7568	Intermediate Similarity	NPC237503
0.7568	Intermediate Similarity	NPC306746
0.7568	Intermediate Similarity	NPC137917
0.7565	Intermediate Similarity	NPC203862
0.7565	Intermediate Similarity	NPC13713
0.7565	Intermediate Similarity	NPC309433
0.7565	Intermediate Similarity	NPC473968
0.7563	Intermediate Similarity	NPC318135
0.7561	Intermediate Similarity	NPC316915
0.7549	Intermediate Similarity	NPC327183
0.7549	Intermediate Similarity	NPC328935
0.7545	Intermediate Similarity	NPC67321
0.7545	Intermediate Similarity	NPC187435
0.7545	Intermediate Similarity	NPC33053
0.7545	Intermediate Similarity	NPC472390

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 NPC151516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1740
0.2-0.3	3980
0.3-0.4	2205
0.4-0.5	622
0.5-0.6	319
0.6-0.7	86
0.7-0.8	4
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
0.8131	Intermediate Similarity	NPD6686	Approved
0.787	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD7507	Approved
0.7411	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD46	Approved
0.7379	Intermediate Similarity	NPD6698	Approved
0.735	Intermediate Similarity	NPD7328	Approved
0.735	Intermediate Similarity	NPD7327	Approved
0.7333	Intermediate Similarity	NPD8328	Phase 3
0.7317	Intermediate Similarity	NPD7319	Approved
0.7311	Intermediate Similarity	NPD7503	Approved
0.7288	Intermediate Similarity	NPD7516	Approved
0.7227	Intermediate Similarity	NPD8377	Approved
0.7227	Intermediate Similarity	NPD8294	Approved
0.7222	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8033	Approved
0.7167	Intermediate Similarity	NPD8513	Phase 3
0.7167	Intermediate Similarity	NPD8296	Approved
0.7167	Intermediate Similarity	NPD8335	Approved
0.7167	Intermediate Similarity	NPD8379	Approved
0.7167	Intermediate Similarity	NPD8517	Approved
0.7167	Intermediate Similarity	NPD8380	Approved
0.7167	Intermediate Similarity	NPD8515	Approved
0.7167	Intermediate Similarity	NPD8378	Approved
0.7167	Intermediate Similarity	NPD8516	Approved
0.7105	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8133	Approved
0.6967	Remote Similarity	NPD6370	Approved
0.6909	Remote Similarity	NPD4225	Approved
0.6909	Remote Similarity	NPD7638	Approved
0.6847	Remote Similarity	NPD7640	Approved
0.6847	Remote Similarity	NPD7639	Approved
0.6838	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7115	Discovery
0.6803	Remote Similarity	NPD6054	Approved
0.6803	Remote Similarity	NPD6059	Approved
0.6783	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6371	Approved
0.6748	Remote Similarity	NPD6015	Approved
0.6748	Remote Similarity	NPD6016	Approved
0.6746	Remote Similarity	NPD8293	Discontinued
0.6724	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5988	Approved
0.6694	Remote Similarity	NPD6009	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.664	Remote Similarity	NPD6067	Discontinued
0.6639	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8074	Phase 3
0.6587	Remote Similarity	NPD7492	Approved
0.6583	Remote Similarity	NPD4632	Approved
0.6574	Remote Similarity	NPD7838	Discovery
0.6545	Remote Similarity	NPD5282	Discontinued
0.6538	Remote Similarity	NPD6110	Phase 1
0.6535	Remote Similarity	NPD6616	Approved
0.6525	Remote Similarity	NPD6373	Approved
0.6525	Remote Similarity	NPD6372	Approved
0.6518	Remote Similarity	NPD7902	Approved
0.6509	Remote Similarity	NPD3618	Phase 1
0.6508	Remote Similarity	NPD7642	Approved
0.65	Remote Similarity	NPD8297	Approved
0.65	Remote Similarity	NPD6053	Discontinued
0.6496	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5344	Discontinued
0.6484	Remote Similarity	NPD7078	Approved
0.6417	Remote Similarity	NPD6649	Approved
0.6417	Remote Similarity	NPD6650	Approved
0.6415	Remote Similarity	NPD1694	Approved
0.6412	Remote Similarity	NPD7260	Phase 2
0.641	Remote Similarity	NPD7128	Approved
0.641	Remote Similarity	NPD6675	Approved
0.641	Remote Similarity	NPD5739	Approved
0.641	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD7748	Approved
0.6378	Remote Similarity	NPD7829	Approved
0.6378	Remote Similarity	NPD7830	Approved
0.6372	Remote Similarity	NPD4755	Approved
0.6372	Remote Similarity	NPD6083	Phase 2
0.6372	Remote Similarity	NPD6084	Phase 2
0.6371	Remote Similarity	NPD7641	Discontinued
0.6364	Remote Similarity	NPD7983	Approved
0.6364	Remote Similarity	NPD7515	Phase 2
0.6356	Remote Similarity	NPD5697	Approved
0.6356	Remote Similarity	NPD5701	Approved
0.6339	Remote Similarity	NPD5695	Phase 3
0.6333	Remote Similarity	NPD4634	Approved
0.633	Remote Similarity	NPD4753	Phase 2
0.6321	Remote Similarity	NPD3665	Phase 1
0.6321	Remote Similarity	NPD3666	Approved
0.6321	Remote Similarity	NPD3133	Approved
0.6316	Remote Similarity	NPD5696	Approved
0.6308	Remote Similarity	NPD6033	Approved
0.6306	Remote Similarity	NPD6399	Phase 3
0.6306	Remote Similarity	NPD4202	Approved
0.6303	Remote Similarity	NPD6899	Approved
0.6303	Remote Similarity	NPD7320	Approved
0.6303	Remote Similarity	NPD6881	Approved
0.6293	Remote Similarity	NPD7632	Discontinued
0.6293	Remote Similarity	NPD5211	Phase 2
0.6286	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8451	Approved
0.6271	Remote Similarity	NPD6008	Approved
0.6261	Remote Similarity	NPD5286	Approved
0.6261	Remote Similarity	NPD4700	Approved
0.6261	Remote Similarity	NPD4696	Approved
0.6261	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6013	Approved
0.6231	Remote Similarity	NPD8448	Approved
0.622	Remote Similarity	NPD8444	Approved
0.622	Remote Similarity	NPD6921	Approved
0.622	Remote Similarity	NPD5983	Phase 2
0.6212	Remote Similarity	NPD5956	Approved
0.6198	Remote Similarity	NPD7290	Approved
0.6198	Remote Similarity	NPD6883	Approved
0.6198	Remote Similarity	NPD7102	Approved
0.6195	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5210	Approved
0.6195	Remote Similarity	NPD4629	Approved
0.6186	Remote Similarity	NPD5141	Approved
0.6182	Remote Similarity	NPD5328	Approved
0.6167	Remote Similarity	NPD6011	Approved
0.6161	Remote Similarity	NPD5779	Approved
0.6161	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD5225	Approved
0.6154	Remote Similarity	NPD5226	Approved
0.6154	Remote Similarity	NPD4633	Approved
0.6154	Remote Similarity	NPD5224	Approved
0.6148	Remote Similarity	NPD8130	Phase 1
0.6148	Remote Similarity	NPD6617	Approved
0.6148	Remote Similarity	NPD6869	Approved
0.6148	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD4697	Phase 3
0.6134	Remote Similarity	NPD4768	Approved
0.6134	Remote Similarity	NPD4767	Approved
0.6132	Remote Similarity	NPD3667	Approved
0.6126	Remote Similarity	NPD5785	Approved
0.6124	Remote Similarity	NPD7604	Phase 2
0.6121	Remote Similarity	NPD6648	Approved
0.6119	Remote Similarity	NPD6845	Suspended
0.6102	Remote Similarity	NPD5175	Approved
0.6102	Remote Similarity	NPD5174	Approved
0.609	Remote Similarity	NPD8390	Approved
0.609	Remote Similarity	NPD6914	Discontinued
0.609	Remote Similarity	NPD8392	Approved
0.609	Remote Similarity	NPD8391	Approved
0.6077	Remote Similarity	NPD8341	Approved
0.6077	Remote Similarity	NPD8340	Approved
0.6077	Remote Similarity	NPD8299	Approved
0.6077	Remote Similarity	NPD8342	Approved
0.6075	Remote Similarity	NPD3669	Approved
0.6075	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5284	Approved
0.6071	Remote Similarity	NPD5693	Phase 1
0.6071	Remote Similarity	NPD6411	Approved
0.6071	Remote Similarity	NPD5281	Approved
0.6071	Remote Similarity	NPD6079	Approved
0.6068	Remote Similarity	NPD5223	Approved
0.6058	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4623	Approved
0.6055	Remote Similarity	NPD5279	Phase 3
0.6055	Remote Similarity	NPD4519	Discontinued
0.6055	Remote Similarity	NPD6684	Approved
0.6055	Remote Similarity	NPD7146	Approved
0.6055	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7334	Approved
0.6055	Remote Similarity	NPD6409	Approved
0.6055	Remote Similarity	NPD5330	Approved
0.6055	Remote Similarity	NPD7521	Approved
0.6033	Remote Similarity	NPD4729	Approved
0.6033	Remote Similarity	NPD4730	Approved
0.6031	Remote Similarity	NPD6336	Discontinued
0.6019	Remote Similarity	NPD4786	Approved
0.6016	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD5221	Approved
0.5981	Remote Similarity	NPD4223	Phase 3
0.5981	Remote Similarity	NPD4221	Approved
0.5966	Remote Similarity	NPD4754	Approved
0.5963	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6274	Approved
0.5948	Remote Similarity	NPD5173	Approved
0.5946	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6672	Approved
0.5946	Remote Similarity	NPD5737	Approved
0.5946	Remote Similarity	NPD6903	Approved
0.5943	Remote Similarity	NPD4695	Discontinued
0.594	Remote Similarity	NPD8336	Approved
0.594	Remote Similarity	NPD8337	Approved
0.5935	Remote Similarity	NPD5249	Phase 3

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