NPASS Compound

Structure

NPC470685 OpenBabel07101719132D 47 51 0 0 1 0 0 0 0 0999 V2000 9.9129 -3.5157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6257 -2.3567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9933 1.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 8.0077 -0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3678 1.2396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 1.0827 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 10.5820 -2.7725 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6987 0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9859 -0.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3460 1.0317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 0.1691 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 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.5602 -2.9805 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 12.2293 -2.2373 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9203 -1.2863 0.0000 C 0 0 2 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 9.6550 0.0806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7206 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9422 -1.0783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8692 -3.9315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.2075 -2.4452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5894 -0.5431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4115 1.6554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2949 -1.6136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0151 1.7748 0.0000 O 0 0 0 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 10.2730 -1.8215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0514 -0.0388 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 10.6331 -0.1273 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 3 40 1 0 0 0 0 4 41 1 0 0 0 0 5 6 2 0 0 0 0 6 42 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 9 30 1 0 0 0 0 10 31 1 0 0 0 0 11 1 1 6 0 0 0 11 19 1 0 0 0 0 11 43 1 0 0 0 0 12 26 1 0 0 0 0 13 5 1 6 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 25 2 0 0 0 0 14 40 1 0 0 0 0 15 25 1 0 0 0 0 15 41 1 0 0 0 0 16 44 1 1 0 0 0 17 10 1 1 0 0 0 17 20 1 0 0 0 0 17 45 1 0 0 0 0 18 27 1 0 0 0 0 18 30 1 6 0 0 0 19 21 1 0 0 0 0 19 32 1 1 0 0 0 20 22 1 0 0 0 0 20 33 1 6 0 0 0 21 23 1 0 0 0 0 21 34 1 6 0 0 0 22 24 1 0 0 0 0 22 35 1 1 0 0 0 23 28 1 0 0 0 0 23 36 1 6 0 0 0 24 29 1 0 0 0 0 24 37 1 6 0 0 0 25 46 1 0 0 0 0 26 38 2 0 0 0 0 26 44 1 0 0 0 0 27 42 1 0 0 0 0 27 47 1 1 0 0 0 28 43 1 0 0 0 0 28 46 1 1 0 0 0 29 45 1 0 0 0 0 29 47 1 1 0 0 0 30 2 1 6 0 0 0 30 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	674.24
Volume:	620.905
LogP:	0.255
LogD:	0.141
LogS:	-2.561
# Rotatable Bonds:	10
TPSA:	252.75
# H-Bond Aceptor:	17
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.126
Synthetic Accessibility Score:	5.359
Fsp3:	0.7
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.571
MDCK Permeability:	0.0002471567422617227
Pgp-inhibitor:	0.003
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.948
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	31.39438247680664%
Volume Distribution (VD):	0.434
Pgp-substrate:	24.94264030456543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.556
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	1.156
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.626
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.038
Carcinogencity:	0.181
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC470685

Natural Product ID:	NPC470685
*Common Name:**	Rehmaglutoside C
IUPAC Name:	[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 3,5-dimethoxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxybenzoate
Synonyms:	Rehmaglutoside C
Standard InCHIKey:	KCPUTZOAXAJLIB-WJTAVRCFSA-N
Standard InCHI:	InChI=1S/C30H42O17/c1-11-19(32)21(34)23(36)28(43-11)46-25-14(40-3)7-12(8-15(25)41-4)26(38)44-16-9-30(2,39)18-13(16)5-6-42-27(18)47-29-24(37)22(35)20(33)17(10-31)45-29/h5-8,11,13,16-24,27-29,31-37,39H,9-10H2,1-4H3/t11-,13-,16+,17+,18+,19-,20+,21+,22-,23+,24+,27-,28-,29-,30-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@](C)(O)C[C@H]3OC(=O)c2cc(OC)c(c(c2)OC)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2177298
PubChem CID:	71451794
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	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	5
Others	2

Activity Type	# Activity
Cell Line	5
CELL-LINE	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[512665]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[512665]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[512665]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[512665]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[512665]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	33.6	%	PMID[512665]
NPT21742	CELL-LINE	L02	Homo sapiens	Survival	=	71.0	%	PMID[512665]

☑ 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 NPC470685 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	381
0.1-0.2	1556
0.2-0.3	3274
0.3-0.4	7112
0.4-0.5	10532
0.5-0.6	6624
0.6-0.7	7307
0.7-0.8	5485
0.8-0.85	370
0.85-0.9	51
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC282551
0.9437	High Similarity	NPC474936
0.9202	High Similarity	NPC206815
0.9202	High Similarity	NPC476011
0.9036	High Similarity	NPC130730
0.9036	High Similarity	NPC301910
0.8929	High Similarity	NPC21956
0.8902	High Similarity	NPC473776
0.8902	High Similarity	NPC473205
0.8855	High Similarity	NPC41009
0.883	High Similarity	NPC84482
0.883	High Similarity	NPC169645
0.8817	High Similarity	NPC658
0.8817	High Similarity	NPC197708
0.8788	High Similarity	NPC289811
0.8788	High Similarity	NPC179914
0.8788	High Similarity	NPC160780
0.8773	High Similarity	NPC478232
0.8772	High Similarity	NPC163165
0.8757	High Similarity	NPC230670
0.8757	High Similarity	NPC71385
0.875	High Similarity	NPC308178
0.8743	High Similarity	NPC285108
0.8743	High Similarity	NPC148273
0.8743	High Similarity	NPC33298
0.8735	High Similarity	NPC239966
0.8735	High Similarity	NPC203020
0.8735	High Similarity	NPC138993
0.8727	High Similarity	NPC1913
0.8713	High Similarity	NPC5786
0.8713	High Similarity	NPC102851
0.8712	High Similarity	NPC105827
0.8712	High Similarity	NPC246893
0.8712	High Similarity	NPC310661
0.8708	High Similarity	NPC112708
0.869	High Similarity	NPC109990
0.8683	High Similarity	NPC472859
0.8683	High Similarity	NPC25389
0.8683	High Similarity	NPC311803
0.8659	High Similarity	NPC473711
0.865	High Similarity	NPC36130
0.865	High Similarity	NPC134905
0.8642	High Similarity	NPC147224
0.8631	High Similarity	NPC145847
0.8623	High Similarity	NPC289346
0.8623	High Similarity	NPC119125
0.8623	High Similarity	NPC166277
0.8614	High Similarity	NPC472860
0.8598	High Similarity	NPC137813
0.8589	High Similarity	NPC269914
0.8589	High Similarity	NPC475379
0.8589	High Similarity	NPC478249
0.8588	High Similarity	NPC96194
0.8588	High Similarity	NPC299855
0.858	High Similarity	NPC478234
0.858	High Similarity	NPC478236
0.8563	High Similarity	NPC287872
0.8563	High Similarity	NPC74319
0.8545	High Similarity	NPC327032
0.8545	High Similarity	NPC191046
0.8545	High Similarity	NPC194095
0.8539	High Similarity	NPC189704
0.8537	High Similarity	NPC203664
0.8529	High Similarity	NPC472130
0.8529	High Similarity	NPC15358
0.8529	High Similarity	NPC475366
0.8529	High Similarity	NPC475497
0.8529	High Similarity	NPC284277
0.8529	High Similarity	NPC472131
0.8528	High Similarity	NPC227980
0.8521	High Similarity	NPC90905
0.8521	High Similarity	NPC4013
0.8506	High Similarity	NPC469354
0.8503	High Similarity	NPC4747
0.8503	High Similarity	NPC226759
0.8503	High Similarity	NPC187205
0.8503	High Similarity	NPC49173
0.8503	High Similarity	NPC133984
0.8503	High Similarity	NPC104275
0.8497	Intermediate Similarity	NPC475155
0.8497	Intermediate Similarity	NPC38438
0.8494	Intermediate Similarity	NPC10205
0.8494	Intermediate Similarity	NPC172920
0.8494	Intermediate Similarity	NPC156624
0.8494	Intermediate Similarity	NPC475484
0.8492	Intermediate Similarity	NPC476067
0.8492	Intermediate Similarity	NPC475121
0.8488	Intermediate Similarity	NPC61791
0.8476	Intermediate Similarity	NPC158546
0.8476	Intermediate Similarity	NPC289021
0.8475	Intermediate Similarity	NPC199172
0.8475	Intermediate Similarity	NPC473883
0.8475	Intermediate Similarity	NPC35924
0.8466	Intermediate Similarity	NPC111785
0.8462	Intermediate Similarity	NPC182045
0.8457	Intermediate Similarity	NPC79736
0.8457	Intermediate Similarity	NPC67629
0.8457	Intermediate Similarity	NPC473713
0.8457	Intermediate Similarity	NPC473149
0.8443	Intermediate Similarity	NPC471405
0.8439	Intermediate Similarity	NPC43434
0.8439	Intermediate Similarity	NPC472129
0.843	Intermediate Similarity	NPC116745
0.843	Intermediate Similarity	NPC135345
0.8424	Intermediate Similarity	NPC194705
0.8421	Intermediate Similarity	NPC475738
0.8421	Intermediate Similarity	NPC180586
0.8415	Intermediate Similarity	NPC117346
0.8415	Intermediate Similarity	NPC473091
0.8415	Intermediate Similarity	NPC240592
0.8409	Intermediate Similarity	NPC173837
0.8409	Intermediate Similarity	NPC120952
0.8409	Intermediate Similarity	NPC267549
0.8409	Intermediate Similarity	NPC475261
0.8402	Intermediate Similarity	NPC478265
0.8402	Intermediate Similarity	NPC110349
0.84	Intermediate Similarity	NPC107739
0.8395	Intermediate Similarity	NPC37838
0.8391	Intermediate Similarity	NPC261254
0.8391	Intermediate Similarity	NPC472386
0.8391	Intermediate Similarity	NPC235575
0.8391	Intermediate Similarity	NPC254540
0.8391	Intermediate Similarity	NPC211594
0.8391	Intermediate Similarity	NPC172807
0.8382	Intermediate Similarity	NPC195257
0.8382	Intermediate Similarity	NPC198125
0.8382	Intermediate Similarity	NPC149300
0.8382	Intermediate Similarity	NPC86008
0.8382	Intermediate Similarity	NPC209296
0.8382	Intermediate Similarity	NPC95421
0.8382	Intermediate Similarity	NPC229687
0.8382	Intermediate Similarity	NPC472133
0.8373	Intermediate Similarity	NPC478241
0.8373	Intermediate Similarity	NPC89693
0.8373	Intermediate Similarity	NPC229548
0.8372	Intermediate Similarity	NPC99957
0.8372	Intermediate Similarity	NPC181616
0.8371	Intermediate Similarity	NPC470445
0.8371	Intermediate Similarity	NPC470446
0.8371	Intermediate Similarity	NPC470447
0.8371	Intermediate Similarity	NPC470449
0.8363	Intermediate Similarity	NPC243930
0.8363	Intermediate Similarity	NPC88023
0.8363	Intermediate Similarity	NPC309025
0.8362	Intermediate Similarity	NPC473895
0.8352	Intermediate Similarity	NPC475299
0.8352	Intermediate Similarity	NPC257714
0.8352	Intermediate Similarity	NPC23593
0.8352	Intermediate Similarity	NPC211532
0.8352	Intermediate Similarity	NPC89127
0.8352	Intermediate Similarity	NPC297574
0.8352	Intermediate Similarity	NPC233994
0.8352	Intermediate Similarity	NPC471669
0.8344	Intermediate Similarity	NPC52740
0.8343	Intermediate Similarity	NPC88560
0.8343	Intermediate Similarity	NPC46640
0.8343	Intermediate Similarity	NPC166674
0.8343	Intermediate Similarity	NPC34436
0.8343	Intermediate Similarity	NPC4390
0.8343	Intermediate Similarity	NPC472993
0.8343	Intermediate Similarity	NPC469384
0.8343	Intermediate Similarity	NPC219600
0.8343	Intermediate Similarity	NPC316539
0.8343	Intermediate Similarity	NPC204693
0.8343	Intermediate Similarity	NPC175230
0.8343	Intermediate Similarity	NPC263119
0.8343	Intermediate Similarity	NPC172033
0.8343	Intermediate Similarity	NPC473550
0.8333	Intermediate Similarity	NPC231194
0.8333	Intermediate Similarity	NPC52353
0.8333	Intermediate Similarity	NPC478248
0.8333	Intermediate Similarity	NPC44558
0.8333	Intermediate Similarity	NPC105511
0.8333	Intermediate Similarity	NPC293004
0.8333	Intermediate Similarity	NPC149011
0.8333	Intermediate Similarity	NPC204937
0.8333	Intermediate Similarity	NPC212748
0.8333	Intermediate Similarity	NPC194483
0.8333	Intermediate Similarity	NPC51326
0.8324	Intermediate Similarity	NPC21359
0.8324	Intermediate Similarity	NPC470717
0.8324	Intermediate Similarity	NPC229729
0.8324	Intermediate Similarity	NPC470713
0.8324	Intermediate Similarity	NPC45400
0.8324	Intermediate Similarity	NPC25946
0.8324	Intermediate Similarity	NPC470720
0.8324	Intermediate Similarity	NPC460984
0.8324	Intermediate Similarity	NPC470455
0.8324	Intermediate Similarity	NPC470451
0.8323	Intermediate Similarity	NPC242756
0.8315	Intermediate Similarity	NPC170203
0.8315	Intermediate Similarity	NPC469371
0.8314	Intermediate Similarity	NPC475979
0.8314	Intermediate Similarity	NPC311830
0.8314	Intermediate Similarity	NPC22832
0.8314	Intermediate Similarity	NPC294722
0.8313	Intermediate Similarity	NPC228662
0.8313	Intermediate Similarity	NPC478235
0.8313	Intermediate Similarity	NPC75695
0.8313	Intermediate Similarity	NPC80098

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 NPC470685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	867
0.2-0.3	1939
0.3-0.4	2639
0.4-0.5	2044
0.5-0.6	942
0.6-0.7	321
0.7-0.8	74
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8994	High Similarity	NPD7685	Pre-registration
0.8439	Intermediate Similarity	NPD7472	Approved
0.8382	Intermediate Similarity	NPD7054	Approved
0.8295	Intermediate Similarity	NPD7808	Phase 3
0.8239	Intermediate Similarity	NPD7251	Discontinued
0.8229	Intermediate Similarity	NPD7074	Phase 3
0.8218	Intermediate Similarity	NPD3818	Discontinued
0.8192	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.814	Intermediate Similarity	NPD7199	Phase 2
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1653	Approved
0.791	Intermediate Similarity	NPD7228	Approved
0.7857	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3817	Phase 2
0.7833	Intermediate Similarity	NPD7240	Approved
0.7778	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5494	Approved
0.7765	Intermediate Similarity	NPD5844	Phase 1
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD37	Approved
0.7701	Intermediate Similarity	NPD4967	Phase 2
0.7701	Intermediate Similarity	NPD4965	Approved
0.7701	Intermediate Similarity	NPD4966	Approved
0.7697	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6166	Phase 2
0.7697	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1465	Phase 2
0.763	Intermediate Similarity	NPD1934	Approved
0.7614	Intermediate Similarity	NPD6234	Discontinued
0.7586	Intermediate Similarity	NPD2801	Approved
0.7546	Intermediate Similarity	NPD230	Phase 1
0.7543	Intermediate Similarity	NPD5353	Approved
0.7541	Intermediate Similarity	NPD6559	Discontinued
0.753	Intermediate Similarity	NPD7266	Discontinued
0.7528	Intermediate Similarity	NPD8127	Discontinued
0.75	Intermediate Similarity	NPD3882	Suspended
0.7486	Intermediate Similarity	NPD7819	Suspended
0.7486	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8455	Phase 2
0.7471	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8312	Approved
0.7459	Intermediate Similarity	NPD8313	Approved
0.7458	Intermediate Similarity	NPD7075	Discontinued
0.7443	Intermediate Similarity	NPD5402	Approved
0.7414	Intermediate Similarity	NPD4380	Phase 2
0.7396	Intermediate Similarity	NPD4628	Phase 3
0.7368	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7473	Discontinued
0.7353	Intermediate Similarity	NPD6190	Approved
0.733	Intermediate Similarity	NPD6801	Discontinued
0.7293	Intermediate Similarity	NPD6232	Discontinued
0.7289	Intermediate Similarity	NPD6653	Approved
0.7283	Intermediate Similarity	NPD6273	Approved
0.7267	Intermediate Similarity	NPD1511	Approved
0.7267	Intermediate Similarity	NPD6799	Approved
0.7241	Intermediate Similarity	NPD5403	Approved
0.7228	Intermediate Similarity	NPD3751	Discontinued
0.7225	Intermediate Similarity	NPD5401	Approved
0.7216	Intermediate Similarity	NPD7028	Phase 2
0.7198	Intermediate Similarity	NPD3787	Discontinued
0.7184	Intermediate Similarity	NPD1512	Approved
0.7176	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7411	Suspended
0.7164	Intermediate Similarity	NPD8151	Discontinued
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD919	Approved
0.7126	Intermediate Similarity	NPD1933	Approved
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD447	Suspended
0.7119	Intermediate Similarity	NPD6599	Discontinued
0.7095	Intermediate Similarity	NPD5760	Phase 2
0.7095	Intermediate Similarity	NPD5761	Phase 2
0.7093	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3750	Approved
0.7085	Intermediate Similarity	NPD7680	Approved
0.7083	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5242	Approved
0.7065	Intermediate Similarity	NPD7583	Approved
0.7059	Intermediate Similarity	NPD2796	Approved
0.7035	Intermediate Similarity	NPD6674	Discontinued
0.703	Intermediate Similarity	NPD7585	Approved
0.701	Intermediate Similarity	NPD7783	Phase 2
0.701	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD3748	Approved
0.6994	Remote Similarity	NPD4110	Phase 3
0.6994	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6385	Approved
0.6983	Remote Similarity	NPD6386	Approved
0.6978	Remote Similarity	NPD3749	Approved
0.6977	Remote Similarity	NPD1549	Phase 2
0.6973	Remote Similarity	NPD3926	Phase 2
0.697	Remote Similarity	NPD9494	Approved
0.6966	Remote Similarity	NPD7458	Discontinued
0.6957	Remote Similarity	NPD1247	Approved
0.6957	Remote Similarity	NPD6959	Discontinued
0.6952	Remote Similarity	NPD7799	Discontinued
0.6941	Remote Similarity	NPD7097	Phase 1
0.6936	Remote Similarity	NPD1652	Phase 2
0.6935	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2532	Approved
0.6932	Remote Similarity	NPD2534	Approved
0.6932	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2533	Approved
0.6932	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7768	Phase 2
0.6923	Remote Similarity	NPD5124	Phase 1
0.6919	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6005	Phase 3
0.6919	Remote Similarity	NPD5762	Approved
0.6919	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6004	Phase 3
0.6919	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6002	Phase 3
0.6919	Remote Similarity	NPD5763	Approved
0.6915	Remote Similarity	NPD7497	Discontinued
0.6909	Remote Similarity	NPD5647	Approved
0.6897	Remote Similarity	NPD7584	Approved
0.6886	Remote Similarity	NPD3027	Phase 3
0.6875	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD9269	Phase 2
0.6864	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1613	Approved
0.6854	Remote Similarity	NPD920	Approved
0.685	Remote Similarity	NPD6777	Approved
0.685	Remote Similarity	NPD6782	Approved
0.685	Remote Similarity	NPD6779	Approved
0.685	Remote Similarity	NPD6780	Approved
0.685	Remote Similarity	NPD6778	Approved
0.685	Remote Similarity	NPD6781	Approved
0.685	Remote Similarity	NPD6776	Approved
0.6848	Remote Similarity	NPD6362	Approved
0.6839	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD9268	Approved
0.6832	Remote Similarity	NPD7696	Phase 3
0.6832	Remote Similarity	NPD7697	Approved
0.6832	Remote Similarity	NPD7698	Approved
0.6828	Remote Similarity	NPD7229	Phase 3
0.681	Remote Similarity	NPD1091	Approved
0.6806	Remote Similarity	NPD6765	Approved
0.6806	Remote Similarity	NPD6764	Approved
0.6802	Remote Similarity	NPD1510	Phase 2
0.6802	Remote Similarity	NPD7033	Discontinued
0.6798	Remote Similarity	NPD8320	Phase 1
0.6798	Remote Similarity	NPD8319	Approved
0.6796	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7874	Approved
0.678	Remote Similarity	NPD7701	Phase 2
0.6778	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7549	Discontinued
0.6769	Remote Similarity	NPD6842	Approved
0.6769	Remote Similarity	NPD6841	Approved
0.6769	Remote Similarity	NPD6843	Phase 3
0.6768	Remote Similarity	NPD1608	Approved
0.6765	Remote Similarity	NPD7999	Approved
0.6763	Remote Similarity	NPD1551	Phase 2
0.6763	Remote Similarity	NPD6100	Approved
0.6763	Remote Similarity	NPD6099	Approved
0.6746	Remote Similarity	NPD7930	Approved
0.6742	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7236	Approved
0.6719	Remote Similarity	NPD7039	Approved
0.6719	Remote Similarity	NPD7038	Approved
0.6718	Remote Similarity	NPD8150	Discontinued
0.6716	Remote Similarity	NPD7871	Phase 2
0.6716	Remote Similarity	NPD7870	Phase 2
0.6707	Remote Similarity	NPD3705	Approved
0.6706	Remote Similarity	NPD6233	Phase 2
0.6703	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6823	Phase 2
0.6683	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD7700	Phase 2
0.6667	Remote Similarity	NPD6784	Approved
0.6667	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD9545	Approved
0.6648	Remote Similarity	NPD1243	Approved
0.663	Remote Similarity	NPD7239	Suspended
0.6629	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6832	Phase 2
0.6627	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5005	Approved
0.6618	Remote Similarity	NPD5006	Approved
0.6617	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6971	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