NPASS Compound

Structure

CID265600 OpenBabel06191716062D 38 43 0 0 1 0 0 0 0 0999 V2000 1.0635 0.5835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9792 1.2344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6502 -0.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9610 1.0444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6320 -0.6561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2196 -0.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8888 -1.5395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4698 -1.9216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9870 -1.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3238 0.4791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2874 0.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9608 -1.4803 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8888 -1.5395 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7776 -1.0263 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7776 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6580 0.6690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8888 0.5132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5498 -2.0601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7286 -0.3588 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0052 -1.2215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0131 -2.4789 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2537 -0.2555 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8888 -2.5658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2692 -0.0907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8888 -2.5658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6664 -1.5395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6664 0.5132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9844 1.6142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1569 -4.4737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8845 -4.3492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3134 -0.0863 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 -0.8888 1.5395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1303 -1.2611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0795 -2.8373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9128 -2.9153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9847 -3.9128 0.0000 S 0 0 3 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 20 1 0 0 0 0 8 22 1 0 0 0 0 9 21 1 0 0 0 0 9 32 1 0 0 0 0 10 17 1 0 0 0 0 11 25 1 0 0 0 0 12 7 1 6 0 0 0 12 14 1 0 0 0 0 12 33 1 0 0 0 0 13 21 1 6 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 1 0 0 0 15 16 1 0 0 0 0 15 27 1 6 0 0 0 16 18 1 0 0 0 0 16 28 1 1 0 0 0 17 29 2 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 18 34 1 6 0 0 0 19 21 1 1 0 0 0 19 35 1 0 0 0 0 19 36 1 0 0 0 0 20 23 1 1 0 0 0 20 35 1 0 0 0 0 21 23 1 6 0 0 0 22 36 1 0 0 0 0 22 37 1 6 0 0 0 23 34 1 1 0 0 0 30 38 1 0 0 0 0 31 38 2 0 0 0 0 37 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.12
Volume:	486.052
LogP:	-0.015
LogD:	-0.387
LogS:	-2.577
# Rotatable Bonds:	9
TPSA:	210.9
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	8
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.158
Synthetic Accessibility Score:	6.593
Fsp3:	0.696
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:	-6.331
MDCK Permeability:	3.428196214372292e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.759
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	50.23447799682617%
Volume Distribution (VD):	0.533
Pgp-substrate:	40.83406448364258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.996
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	2.512
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.201
Drug-inuced Liver Injury (DILI):	0.455
AMES Toxicity:	0.509
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.299
Carcinogencity:	0.962
Eye Corrosion:	0.003
Eye Irritation:	0.052
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC265600

Natural Product ID:	NPC265600
*Common Name:**	Oxypaeoniflorin Sulfonate
IUPAC Name:	n.a.
Synonyms:	Oxypaeoniflorin Sulfonate
Standard InCHIKey:	ZOJNVCFSHMCECY-HEQFYZJVSA-N
Standard InCHI:	InChI=1S/C23H28O14S/c1-20-8-22(37-38(30)31)13-6-23(20,34-18-16(28)15(27)14(26)12(7-24)33-18)21(13,19(35-20)36-22)9-32-17(29)10-2-4-11(25)5-3-10/h2-5,12-16,18-19,24-28H,6-9H2,1H3,(H,30,31)/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22+,23+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@]23C[C@@H]4[C@@]3(COC(=O)c3ccc(cc3)O)[C@@H]3O[C@@]2(C)C[C@]4(O3)OS(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2205279
PubChem CID:	71455848
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	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
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	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
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]
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]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
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]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	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]
NPO9798	Paeonia lactiflora	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	>	100000.0	nM	PMID[549439]

☑ 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 NPC265600 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	398
0.1-0.2	1503
0.2-0.3	2973
0.3-0.4	6070
0.4-0.5	9874
0.5-0.6	10580
0.6-0.7	8935
0.7-0.8	2226
0.8-0.85	101
0.85-0.9	13
0.9-0.95	14
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC293568
0.9806	High Similarity	NPC117943
0.956	High Similarity	NPC469459
0.9437	High Similarity	NPC469396
0.9437	High Similarity	NPC469458
0.9437	High Similarity	NPC88176
0.9437	High Similarity	NPC149002
0.9434	High Similarity	NPC120012
0.9325	High Similarity	NPC477617
0.9207	High Similarity	NPC148185
0.9187	High Similarity	NPC477627
0.9102	High Similarity	NPC80360
0.9096	High Similarity	NPC469438
0.9048	High Similarity	NPC195114
0.9032	High Similarity	NPC222102
0.9032	High Similarity	NPC303429
0.8994	High Similarity	NPC188217
0.8988	High Similarity	NPC260300
0.8974	High Similarity	NPC469415
0.8963	High Similarity	NPC469419
0.8929	High Similarity	NPC469397
0.8805	High Similarity	NPC469422
0.8805	High Similarity	NPC469398
0.8797	High Similarity	NPC267469
0.8797	High Similarity	NPC179128
0.8797	High Similarity	NPC87630
0.8797	High Similarity	NPC116292
0.8742	High Similarity	NPC133430
0.8742	High Similarity	NPC469477
0.8688	High Similarity	NPC34066
0.8688	High Similarity	NPC5115
0.8679	High Similarity	NPC35160
0.8679	High Similarity	NPC162569
0.8655	High Similarity	NPC469418
0.8589	High Similarity	NPC477623
0.8544	High Similarity	NPC208293
0.8528	High Similarity	NPC469399
0.8438	Intermediate Similarity	NPC469448
0.843	Intermediate Similarity	NPC469354
0.8428	Intermediate Similarity	NPC320734
0.8424	Intermediate Similarity	NPC104275
0.8424	Intermediate Similarity	NPC4747
0.8395	Intermediate Similarity	NPC158546
0.8395	Intermediate Similarity	NPC289021
0.8385	Intermediate Similarity	NPC161955
0.8375	Intermediate Similarity	NPC470330
0.8354	Intermediate Similarity	NPC469417
0.8354	Intermediate Similarity	NPC478250
0.8344	Intermediate Similarity	NPC478235
0.8313	Intermediate Similarity	NPC473867
0.8303	Intermediate Similarity	NPC172920
0.8303	Intermediate Similarity	NPC156624
0.8293	Intermediate Similarity	NPC229354
0.8284	Intermediate Similarity	NPC100420
0.8282	Intermediate Similarity	NPC474620
0.8274	Intermediate Similarity	NPC69868
0.8256	Intermediate Similarity	NPC469421
0.825	Intermediate Similarity	NPC469513
0.8239	Intermediate Similarity	NPC204644
0.8239	Intermediate Similarity	NPC102367
0.8235	Intermediate Similarity	NPC469420
0.8199	Intermediate Similarity	NPC474268
0.8199	Intermediate Similarity	NPC119773
0.8199	Intermediate Similarity	NPC143246
0.8199	Intermediate Similarity	NPC475539
0.8187	Intermediate Similarity	NPC77922
0.8187	Intermediate Similarity	NPC473281
0.8182	Intermediate Similarity	NPC257847
0.8176	Intermediate Similarity	NPC161151
0.8171	Intermediate Similarity	NPC475613
0.8165	Intermediate Similarity	NPC27377
0.8165	Intermediate Similarity	NPC291599
0.8165	Intermediate Similarity	NPC41481
0.8165	Intermediate Similarity	NPC118080
0.8165	Intermediate Similarity	NPC472576
0.8165	Intermediate Similarity	NPC87448
0.8165	Intermediate Similarity	NPC97947
0.816	Intermediate Similarity	NPC478234
0.816	Intermediate Similarity	NPC478236
0.8155	Intermediate Similarity	NPC314795
0.815	Intermediate Similarity	NPC475058
0.8137	Intermediate Similarity	NPC475528
0.8129	Intermediate Similarity	NPC114116
0.8121	Intermediate Similarity	NPC221249
0.8121	Intermediate Similarity	NPC469456
0.8103	Intermediate Similarity	NPC13989
0.8101	Intermediate Similarity	NPC90614
0.8101	Intermediate Similarity	NPC97667
0.8101	Intermediate Similarity	NPC100913
0.8101	Intermediate Similarity	NPC171207
0.8101	Intermediate Similarity	NPC275592
0.8098	Intermediate Similarity	NPC476173
0.8095	Intermediate Similarity	NPC226759
0.8092	Intermediate Similarity	NPC476017
0.8089	Intermediate Similarity	NPC471345
0.8084	Intermediate Similarity	NPC472807
0.8075	Intermediate Similarity	NPC296659
0.8075	Intermediate Similarity	NPC202391
0.807	Intermediate Similarity	NPC109990
0.807	Intermediate Similarity	NPC471861
0.8068	Intermediate Similarity	NPC11062
0.8061	Intermediate Similarity	NPC140151
0.8059	Intermediate Similarity	NPC471493
0.805	Intermediate Similarity	NPC16912
0.8037	Intermediate Similarity	NPC473149
0.8036	Intermediate Similarity	NPC148323
0.8036	Intermediate Similarity	NPC283480
0.8025	Intermediate Similarity	NPC210330
0.8023	Intermediate Similarity	NPC470735
0.8023	Intermediate Similarity	NPC180586
0.8023	Intermediate Similarity	NPC102465
0.8023	Intermediate Similarity	NPC329647
0.8023	Intermediate Similarity	NPC475979
0.8012	Intermediate Similarity	NPC38696
0.8012	Intermediate Similarity	NPC187934
0.8012	Intermediate Similarity	NPC97637
0.8012	Intermediate Similarity	NPC473632
0.8012	Intermediate Similarity	NPC241951
0.8012	Intermediate Similarity	NPC132599
0.8012	Intermediate Similarity	NPC469730
0.8012	Intermediate Similarity	NPC475759
0.8012	Intermediate Similarity	NPC477491
0.8012	Intermediate Similarity	NPC194705
0.8012	Intermediate Similarity	NPC145847
0.8012	Intermediate Similarity	NPC470152
0.8012	Intermediate Similarity	NPC41009
0.8	Intermediate Similarity	NPC240592
0.8	Intermediate Similarity	NPC35097
0.8	Intermediate Similarity	NPC104172
0.8	Intermediate Similarity	NPC88886
0.8	Intermediate Similarity	NPC130489
0.8	Intermediate Similarity	NPC327962
0.8	Intermediate Similarity	NPC247219
0.8	Intermediate Similarity	NPC117346
0.8	Intermediate Similarity	NPC208676
0.8	Intermediate Similarity	NPC269668
0.7988	Intermediate Similarity	NPC49173
0.7988	Intermediate Similarity	NPC81835
0.7988	Intermediate Similarity	NPC477483
0.7988	Intermediate Similarity	NPC286919
0.7988	Intermediate Similarity	NPC208651
0.7988	Intermediate Similarity	NPC257309
0.7988	Intermediate Similarity	NPC187205
0.7988	Intermediate Similarity	NPC66991
0.7988	Intermediate Similarity	NPC475663
0.7988	Intermediate Similarity	NPC206641
0.7988	Intermediate Similarity	NPC325032
0.7987	Intermediate Similarity	NPC472547
0.7976	Intermediate Similarity	NPC203757
0.7976	Intermediate Similarity	NPC192219
0.7976	Intermediate Similarity	NPC82190
0.7976	Intermediate Similarity	NPC174599
0.7975	Intermediate Similarity	NPC473147
0.7965	Intermediate Similarity	NPC471286
0.7965	Intermediate Similarity	NPC93172
0.7965	Intermediate Similarity	NPC97574
0.7965	Intermediate Similarity	NPC91288
0.7963	Intermediate Similarity	NPC70403
0.7963	Intermediate Similarity	NPC470159
0.7963	Intermediate Similarity	NPC472572
0.7963	Intermediate Similarity	NPC63304
0.7963	Intermediate Similarity	NPC184817
0.7963	Intermediate Similarity	NPC473088
0.7963	Intermediate Similarity	NPC472568
0.7963	Intermediate Similarity	NPC194938
0.7963	Intermediate Similarity	NPC200471
0.7963	Intermediate Similarity	NPC171525
0.7963	Intermediate Similarity	NPC472575
0.7963	Intermediate Similarity	NPC158663
0.7963	Intermediate Similarity	NPC177940
0.7963	Intermediate Similarity	NPC471104
0.7963	Intermediate Similarity	NPC472571
0.7963	Intermediate Similarity	NPC476973
0.7963	Intermediate Similarity	NPC174982
0.7963	Intermediate Similarity	NPC469349
0.7963	Intermediate Similarity	NPC470157
0.7963	Intermediate Similarity	NPC96903
0.7963	Intermediate Similarity	NPC29704
0.7955	Intermediate Similarity	NPC195972
0.7955	Intermediate Similarity	NPC316539
0.7953	Intermediate Similarity	NPC283209
0.7953	Intermediate Similarity	NPC285567
0.7952	Intermediate Similarity	NPC472658
0.7952	Intermediate Similarity	NPC472657
0.7952	Intermediate Similarity	NPC471135
0.795	Intermediate Similarity	NPC477894
0.795	Intermediate Similarity	NPC91703
0.795	Intermediate Similarity	NPC163087
0.7941	Intermediate Similarity	NPC469384
0.7941	Intermediate Similarity	NPC76211
0.7941	Intermediate Similarity	NPC53139
0.7939	Intermediate Similarity	NPC197037
0.7939	Intermediate Similarity	NPC75945
0.7939	Intermediate Similarity	NPC471103
0.7939	Intermediate Similarity	NPC96599
0.7939	Intermediate Similarity	NPC92117
0.7937	Intermediate Similarity	NPC77493
0.7931	Intermediate Similarity	NPC82602
0.7929	Intermediate Similarity	NPC88007
0.7929	Intermediate Similarity	NPC195954

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 NPC265600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	808
0.2-0.3	1864
0.3-0.4	2931
0.4-0.5	2105
0.5-0.6	861
0.6-0.7	214
0.7-0.8	32
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
0.7877	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7228	Approved
0.7733	Intermediate Similarity	NPD6234	Discontinued
0.7719	Intermediate Similarity	NPD4966	Approved
0.7719	Intermediate Similarity	NPD4967	Phase 2
0.7719	Intermediate Similarity	NPD4965	Approved
0.7637	Intermediate Similarity	NPD8434	Phase 2
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7572	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6559	Discontinued
0.7556	Intermediate Similarity	NPD7685	Pre-registration
0.7546	Intermediate Similarity	NPD7266	Discontinued
0.7544	Intermediate Similarity	NPD37	Approved
0.7528	Intermediate Similarity	NPD3818	Discontinued
0.7486	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6190	Approved
0.7459	Intermediate Similarity	NPD7240	Approved
0.7444	Intermediate Similarity	NPD7074	Phase 3
0.743	Intermediate Similarity	NPD7799	Discontinued
0.7389	Intermediate Similarity	NPD5844	Phase 1
0.7389	Intermediate Similarity	NPD7054	Approved
0.7389	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8313	Approved
0.7377	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD7458	Discontinued
0.7348	Intermediate Similarity	NPD7472	Approved
0.7345	Intermediate Similarity	NPD7199	Phase 2
0.7337	Intermediate Similarity	NPD8407	Phase 2
0.7326	Intermediate Similarity	NPD4380	Phase 2
0.7322	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6797	Phase 2
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7268	Intermediate Similarity	NPD8368	Discontinued
0.7268	Intermediate Similarity	NPD7251	Discontinued
0.7267	Intermediate Similarity	NPD3764	Approved
0.7258	Intermediate Similarity	NPD8150	Discontinued
0.7251	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD230	Phase 1
0.7231	Intermediate Similarity	NPD8320	Phase 1
0.7231	Intermediate Similarity	NPD8319	Approved
0.7228	Intermediate Similarity	NPD7808	Phase 3
0.7211	Intermediate Similarity	NPD6535	Approved
0.7211	Intermediate Similarity	NPD6534	Approved
0.7205	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8455	Phase 2
0.7188	Intermediate Similarity	NPD7700	Phase 2
0.7188	Intermediate Similarity	NPD7699	Phase 2
0.7179	Intermediate Similarity	NPD7435	Discontinued
0.7167	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2533	Approved
0.7135	Intermediate Similarity	NPD2534	Approved
0.7135	Intermediate Similarity	NPD2532	Approved
0.7113	Intermediate Similarity	NPD6781	Approved
0.7113	Intermediate Similarity	NPD6778	Approved
0.7113	Intermediate Similarity	NPD6782	Approved
0.7113	Intermediate Similarity	NPD6780	Approved
0.7113	Intermediate Similarity	NPD6776	Approved
0.7113	Intermediate Similarity	NPD6779	Approved
0.7113	Intermediate Similarity	NPD6777	Approved
0.7111	Intermediate Similarity	NPD6232	Discontinued
0.711	Intermediate Similarity	NPD1653	Approved
0.7102	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7819	Suspended
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8166	Discontinued
0.7097	Intermediate Similarity	NPD9545	Approved
0.7095	Intermediate Similarity	NPD5494	Approved
0.7092	Intermediate Similarity	NPD7680	Approved
0.709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7473	Discontinued
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7045	Intermediate Similarity	NPD6801	Discontinued
0.7045	Intermediate Similarity	NPD1934	Approved
0.7035	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6166	Phase 2
0.7033	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6599	Discontinued
0.7027	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7236	Approved
0.7006	Intermediate Similarity	NPD1465	Phase 2
0.7005	Intermediate Similarity	NPD7497	Discontinued
0.7005	Intermediate Similarity	NPD7696	Phase 3
0.7005	Intermediate Similarity	NPD7698	Approved
0.7005	Intermediate Similarity	NPD7697	Approved
0.7	Intermediate Similarity	NPD8360	Approved
0.7	Intermediate Similarity	NPD8361	Approved
0.7	Intermediate Similarity	NPD8151	Discontinued
0.6994	Remote Similarity	NPD6273	Approved
0.6989	Remote Similarity	NPD6765	Approved
0.6989	Remote Similarity	NPD6764	Approved
0.6982	Remote Similarity	NPD970	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7874	Approved
0.695	Remote Similarity	NPD7701	Phase 2
0.6941	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7999	Approved
0.6932	Remote Similarity	NPD7028	Phase 2
0.6931	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7783	Phase 2
0.6914	Remote Similarity	NPD7239	Suspended
0.6912	Remote Similarity	NPD7930	Approved
0.6911	Remote Similarity	NPD8435	Approved
0.691	Remote Similarity	NPD5760	Phase 2
0.691	Remote Similarity	NPD5761	Phase 2
0.6909	Remote Similarity	NPD6663	Approved
0.6893	Remote Similarity	NPD7411	Suspended
0.6891	Remote Similarity	NPD6212	Phase 3
0.6891	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6213	Phase 3
0.6884	Remote Similarity	NPD7871	Phase 2
0.6884	Remote Similarity	NPD7870	Phase 2
0.6872	Remote Similarity	NPD3817	Phase 2
0.6872	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6823	Phase 2
0.6868	Remote Similarity	NPD6959	Discontinued
0.6865	Remote Similarity	NPD3751	Discontinued
0.6864	Remote Similarity	NPD2935	Discontinued
0.685	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7801	Approved
0.6845	Remote Similarity	NPD8404	Phase 2
0.6833	Remote Similarity	NPD7057	Phase 3
0.6833	Remote Similarity	NPD3882	Suspended
0.6833	Remote Similarity	NPD7058	Phase 2
0.6816	Remote Similarity	NPD2801	Approved
0.681	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3750	Approved
0.6802	Remote Similarity	NPD7003	Approved
0.6796	Remote Similarity	NPD3749	Approved
0.6789	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1549	Phase 2
0.6782	Remote Similarity	NPD6799	Approved
0.678	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5402	Approved
0.6768	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5736	Approved
0.6765	Remote Similarity	NPD6100	Approved
0.6765	Remote Similarity	NPD6099	Approved
0.6758	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6785	Approved
0.6754	Remote Similarity	NPD6784	Approved
0.6743	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5710	Approved
0.6739	Remote Similarity	NPD5711	Approved
0.6739	Remote Similarity	NPD3787	Discontinued
0.6725	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6002	Phase 3
0.6725	Remote Similarity	NPD6004	Phase 3
0.6725	Remote Similarity	NPD6005	Phase 3
0.6725	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1510	Phase 2
0.67	Remote Similarity	NPD7585	Approved
0.6687	Remote Similarity	NPD5125	Phase 3
0.6687	Remote Similarity	NPD5126	Approved
0.6685	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.665	Remote Similarity	NPD7583	Approved
0.6648	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7768	Phase 2
0.6647	Remote Similarity	NPD7097	Phase 1
0.6647	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2800	Approved
0.6647	Remote Similarity	NPD6674	Discontinued
0.6635	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6355	Discontinued
0.6616	Remote Similarity	NPD8485	Approved
0.6609	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4110	Phase 3
0.6608	Remote Similarity	NPD7033	Discontinued
0.6591	Remote Similarity	NPD1511	Approved
0.6588	Remote Similarity	NPD1607	Approved
0.657	Remote Similarity	NPD2438	Suspended
0.657	Remote Similarity	NPD5406	Approved
0.657	Remote Similarity	NPD5405	Approved
0.657	Remote Similarity	NPD2796	Approved
0.657	Remote Similarity	NPD5408	Approved
0.657	Remote Similarity	NPD5404	Approved
0.657	Remote Similarity	NPD8462	Phase 1
0.6569	Remote Similarity	NPD7584	Approved
0.6568	Remote Similarity	NPD1240	Approved
0.6564	Remote Similarity	NPD9269	Phase 2
0.6559	Remote Similarity	NPD7229	Phase 3
0.6554	Remote Similarity	NPD5401	Approved
0.6554	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3094	Phase 2
0.654	Remote Similarity	NPD4665	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