NPASS Compound

Structure

NPC233500 OpenBabel07101718232D 43 46 0 0 1 0 0 0 0 0999 V2000 -2.8720 -0.6105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3164 0.4277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2652 1.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6641 -3.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7982 -0.5843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2598 -1.1343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0661 1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8165 -0.3146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0887 1.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9573 -0.2035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6641 0.1747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5196 -2.2686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4872 -2.8424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7497 -1.7827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2171 -1.3378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8165 -1.2934 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0891 -1.9483 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.9021 -1.2934 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5104 0.7696 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4769 -2.4721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6641 -1.7827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.9021 -0.3146 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.0545 0.1747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2069 -0.3146 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5117 -1.2934 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2069 -1.2934 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4443 0.8720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4606 -2.7401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9774 -0.0512 0.0000 C 0 0 1 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 -12.5972 -1.2934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4878 0.7184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7793 -3.4029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7497 0.1747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0545 1.1534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3593 0.1747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3914 -3.0425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8749 -2.0060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5544 -0.8066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5117 -0.3146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1318 -1.7448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0545 -1.7827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3593 -1.7827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 5 29 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 9 27 1 0 0 0 0 10 30 1 0 0 0 0 11 40 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 28 1 0 0 0 0 14 31 1 0 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 41 1 6 0 0 0 18 14 1 6 0 0 0 18 22 1 0 0 0 0 18 42 1 0 0 0 0 19 29 1 1 0 0 0 19 32 1 0 0 0 0 20 33 2 0 0 0 0 20 41 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 1 0 0 0 22 23 1 0 0 0 0 22 34 1 1 0 0 0 23 24 1 0 0 0 0 23 35 1 6 0 0 0 24 26 1 0 0 0 0 24 36 1 1 0 0 0 25 40 1 0 0 0 0 25 43 1 6 0 0 0 26 42 1 0 0 0 0 26 43 1 6 0 0 0 27 30 1 0 0 0 0 28 4 1 1 0 0 0 28 37 1 0 0 0 0 29 30 1 6 0 0 0 29 38 1 0 0 0 0 30 39 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.29
Volume:	596.937
LogP:	0.97
LogD:	0.345
LogS:	-2.976
# Rotatable Bonds:	8
TPSA:	215.83
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.1
Synthetic Accessibility Score:	5.761
Fsp3:	0.767
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:	-6.188
MDCK Permeability:	0.00011210079537704587
Pgp-inhibitor:	0.204
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.97
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	54.96923065185547%
Volume Distribution (VD):	0.601
Pgp-substrate:	19.176921844482422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.374
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.158
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	1.344
Half-life (T1/2):	0.712

ADMET: Toxicity

hERG Blockers:	0.151
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.449
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.648
Carcinogencity:	0.219
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC233500

Natural Product ID:	NPC233500
*Common Name:**	Rehmaglutoside H
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] (2E,4E)-3-methyl-5-[(1R,2R,3R)-1,2,3-trihydroxy-2,6,6-trimethylcyclohexyl]penta-2,4-dienoate
Synonyms:	Rehmaglutoside H
Standard InCHIKey:	XAFIIDRISREJRR-JBWCCNGXSA-N
Standard InCHI:	InChI=1S/C30H46O13/c1-15(6-10-30(39)27(2,3)9-7-19(32)29(30,5)38)12-20(33)41-17-13-28(4,37)21-16(17)8-11-40-25(21)43-26-24(36)23(35)22(34)18(14-31)42-26/h6,8,10-12,16-19,21-26,31-32,34-39H,7,9,13-14H2,1-5H3/b10-6+,15-12+/t16-,17+,18+,19+,21+,22+,23-,24+,25-,26-,28-,29+,30+/m0/s1
SMILES:	C/C(=CC(=O)O[C@@H]1C[C@@](C)([C@@H]2[C@H]1C=CO[C@H]2O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)/C=C/[C@]1(C(C)(C)CC[C@H]([C@@]1(C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2177292
PubChem CID:	71460782
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-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
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

Activity Type	# Activity
Cell Line	5

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[486353]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[486353]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[486353]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[486353]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[486353]

☑ 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 NPC233500 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	226
0.1-0.2	1399
0.2-0.3	4031
0.3-0.4	6789
0.4-0.5	13144
0.5-0.6	9521
0.6-0.7	5383
0.7-0.8	2045
0.8-0.85	151
0.85-0.9	2
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9911	High Similarity	NPC196130
0.982	High Similarity	NPC219656
0.9478	High Similarity	NPC219804
0.8898	High Similarity	NPC471082
0.8678	High Similarity	NPC179261
0.8644	High Similarity	NPC5883
0.8644	High Similarity	NPC304260
0.8644	High Similarity	NPC44899
0.8644	High Similarity	NPC29639
0.8632	High Similarity	NPC157376
0.8632	High Similarity	NPC99728
0.8632	High Similarity	NPC50305
0.8632	High Similarity	NPC471353
0.8632	High Similarity	NPC473852
0.8632	High Similarity	NPC152615
0.8632	High Similarity	NPC243196
0.8632	High Similarity	NPC87250
0.8632	High Similarity	NPC471351
0.8632	High Similarity	NPC27507
0.8632	High Similarity	NPC84987
0.8632	High Similarity	NPC471354
0.8632	High Similarity	NPC196429
0.8632	High Similarity	NPC309034
0.8632	High Similarity	NPC244402
0.8632	High Similarity	NPC203862
0.8632	High Similarity	NPC34390
0.8632	High Similarity	NPC77319
0.8632	High Similarity	NPC142066
0.8632	High Similarity	NPC471355
0.8632	High Similarity	NPC474418
0.8632	High Similarity	NPC158344
0.8571	High Similarity	NPC474466
0.8571	High Similarity	NPC112936
0.8571	High Similarity	NPC475136
0.8571	High Similarity	NPC257610
0.8559	High Similarity	NPC83287
0.8547	High Similarity	NPC193382
0.8547	High Similarity	NPC99620
0.8547	High Similarity	NPC5311
0.8547	High Similarity	NPC199428
0.8547	High Similarity	NPC310341
0.8516	High Similarity	NPC75616
0.85	High Similarity	NPC231518
0.85	High Similarity	NPC40749
0.85	High Similarity	NPC475219
0.8487	Intermediate Similarity	NPC278681
0.8487	Intermediate Similarity	NPC81222
0.8487	Intermediate Similarity	NPC35171
0.8487	Intermediate Similarity	NPC213761
0.8487	Intermediate Similarity	NPC329905
0.8487	Intermediate Similarity	NPC291820
0.8475	Intermediate Similarity	NPC93883
0.8462	Intermediate Similarity	NPC84949
0.8462	Intermediate Similarity	NPC69576
0.8462	Intermediate Similarity	NPC106446
0.8462	Intermediate Similarity	NPC471633
0.8462	Intermediate Similarity	NPC31354
0.8448	Intermediate Similarity	NPC317460
0.8448	Intermediate Similarity	NPC321272
0.8448	Intermediate Similarity	NPC44537
0.8448	Intermediate Similarity	NPC328074
0.8448	Intermediate Similarity	NPC470025
0.8435	Intermediate Similarity	NPC177047
0.843	Intermediate Similarity	NPC193893
0.843	Intermediate Similarity	NPC115349
0.8425	Intermediate Similarity	NPC158350
0.8417	Intermediate Similarity	NPC107607
0.8417	Intermediate Similarity	NPC475556
0.8417	Intermediate Similarity	NPC475629
0.8403	Intermediate Similarity	NPC16701
0.8403	Intermediate Similarity	NPC472080
0.8403	Intermediate Similarity	NPC218093
0.839	Intermediate Similarity	NPC207637
0.8376	Intermediate Similarity	NPC470027
0.8362	Intermediate Similarity	NPC17791
0.8359	Intermediate Similarity	NPC62172
0.8359	Intermediate Similarity	NPC289700
0.8347	Intermediate Similarity	NPC314535
0.8347	Intermediate Similarity	NPC173555
0.8333	Intermediate Similarity	NPC32177
0.8333	Intermediate Similarity	NPC55532
0.8333	Intermediate Similarity	NPC155529
0.8333	Intermediate Similarity	NPC30483
0.8333	Intermediate Similarity	NPC153085
0.8333	Intermediate Similarity	NPC292467
0.8333	Intermediate Similarity	NPC470897
0.8333	Intermediate Similarity	NPC268326
0.8333	Intermediate Similarity	NPC236973
0.8333	Intermediate Similarity	NPC469756
0.8319	Intermediate Similarity	NPC290693
0.8319	Intermediate Similarity	NPC157380
0.8319	Intermediate Similarity	NPC185287
0.8291	Intermediate Similarity	NPC216595
0.8291	Intermediate Similarity	NPC473567
0.8279	Intermediate Similarity	NPC264336
0.8276	Intermediate Similarity	NPC316708
0.8264	Intermediate Similarity	NPC72260
0.8261	Intermediate Similarity	NPC50124
0.825	Intermediate Similarity	NPC473617
0.825	Intermediate Similarity	NPC473828
0.8246	Intermediate Similarity	NPC82251
0.822	Intermediate Similarity	NPC171126
0.8211	Intermediate Similarity	NPC308262
0.8211	Intermediate Similarity	NPC117445
0.8211	Intermediate Similarity	NPC208193
0.8205	Intermediate Similarity	NPC470026
0.8197	Intermediate Similarity	NPC474908
0.8197	Intermediate Similarity	NPC120390
0.8197	Intermediate Similarity	NPC475590
0.8197	Intermediate Similarity	NPC475419
0.819	Intermediate Similarity	NPC316974
0.819	Intermediate Similarity	NPC257853
0.819	Intermediate Similarity	NPC75389
0.819	Intermediate Similarity	NPC206618
0.8175	Intermediate Similarity	NPC471407
0.8142	Intermediate Similarity	NPC470571
0.8142	Intermediate Similarity	NPC470972
0.8136	Intermediate Similarity	NPC231797
0.813	Intermediate Similarity	NPC474423
0.813	Intermediate Similarity	NPC74259
0.812	Intermediate Similarity	NPC12795
0.8115	Intermediate Similarity	NPC135369
0.811	Intermediate Similarity	NPC173347
0.8103	Intermediate Similarity	NPC48548
0.8103	Intermediate Similarity	NPC275060
0.8103	Intermediate Similarity	NPC470024
0.8103	Intermediate Similarity	NPC311223
0.8103	Intermediate Similarity	NPC137462
0.8103	Intermediate Similarity	NPC128795
0.8103	Intermediate Similarity	NPC217921
0.8103	Intermediate Similarity	NPC38948
0.8103	Intermediate Similarity	NPC304276
0.8103	Intermediate Similarity	NPC135015
0.8099	Intermediate Similarity	NPC160888
0.8099	Intermediate Similarity	NPC475403
0.8087	Intermediate Similarity	NPC239961
0.8083	Intermediate Similarity	NPC232564
0.8083	Intermediate Similarity	NPC113425
0.8077	Intermediate Similarity	NPC127656
0.8067	Intermediate Similarity	NPC264153
0.8067	Intermediate Similarity	NPC287075
0.8065	Intermediate Similarity	NPC27363
0.8065	Intermediate Similarity	NPC41129
0.8053	Intermediate Similarity	NPC198992
0.8051	Intermediate Similarity	NPC65034
0.8051	Intermediate Similarity	NPC208189
0.8049	Intermediate Similarity	NPC312481
0.8047	Intermediate Similarity	NPC471855
0.8034	Intermediate Similarity	NPC475030
0.8034	Intermediate Similarity	NPC40728
0.8033	Intermediate Similarity	NPC476085
0.8033	Intermediate Similarity	NPC473633
0.8031	Intermediate Similarity	NPC476966
0.8017	Intermediate Similarity	NPC470170
0.8017	Intermediate Similarity	NPC472390
0.8017	Intermediate Similarity	NPC471205
0.8017	Intermediate Similarity	NPC33053
0.8017	Intermediate Similarity	NPC470169
0.8017	Intermediate Similarity	NPC109376
0.8017	Intermediate Similarity	NPC475074
0.8017	Intermediate Similarity	NPC125423
0.8017	Intermediate Similarity	NPC122816
0.8017	Intermediate Similarity	NPC88013
0.8016	Intermediate Similarity	NPC471357
0.8016	Intermediate Similarity	NPC179412
0.8016	Intermediate Similarity	NPC146456
0.8016	Intermediate Similarity	NPC469757
0.8016	Intermediate Similarity	NPC117702
0.8016	Intermediate Similarity	NPC471356
0.8	Intermediate Similarity	NPC152966
0.8	Intermediate Similarity	NPC475163
0.8	Intermediate Similarity	NPC216665
0.8	Intermediate Similarity	NPC473543
0.7984	Intermediate Similarity	NPC298783
0.7984	Intermediate Similarity	NPC104585
0.7984	Intermediate Similarity	NPC157817
0.7984	Intermediate Similarity	NPC225385
0.7983	Intermediate Similarity	NPC475354
0.7982	Intermediate Similarity	NPC11956
0.7982	Intermediate Similarity	NPC201191
0.7982	Intermediate Similarity	NPC214277
0.7982	Intermediate Similarity	NPC121423
0.7967	Intermediate Similarity	NPC145074
0.7967	Intermediate Similarity	NPC41123
0.7967	Intermediate Similarity	NPC475358
0.7967	Intermediate Similarity	NPC473566
0.7967	Intermediate Similarity	NPC114939
0.7967	Intermediate Similarity	NPC50689
0.7966	Intermediate Similarity	NPC103491
0.7966	Intermediate Similarity	NPC170974
0.7966	Intermediate Similarity	NPC119550
0.7966	Intermediate Similarity	NPC103627
0.7966	Intermediate Similarity	NPC65155
0.7966	Intermediate Similarity	NPC191439
0.7953	Intermediate Similarity	NPC311534
0.7949	Intermediate Similarity	NPC224660
0.7937	Intermediate Similarity	NPC469750
0.7937	Intermediate Similarity	NPC250556
0.7934	Intermediate Similarity	NPC146652
0.7934	Intermediate Similarity	NPC470075

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 NPC233500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	1380
0.2-0.3	3696
0.3-0.4	2494
0.4-0.5	876
0.5-0.6	294
0.6-0.7	175
0.7-0.8	22
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8974	High Similarity	NPD7503	Approved
0.8644	High Similarity	NPD7516	Approved
0.8559	High Similarity	NPD7327	Approved
0.8559	High Similarity	NPD7328	Approved
0.85	High Similarity	NPD8033	Approved
0.8347	Intermediate Similarity	NPD8380	Approved
0.8347	Intermediate Similarity	NPD8296	Approved
0.8347	Intermediate Similarity	NPD8378	Approved
0.8347	Intermediate Similarity	NPD8379	Approved
0.8347	Intermediate Similarity	NPD8335	Approved
0.8264	Intermediate Similarity	NPD8294	Approved
0.8264	Intermediate Similarity	NPD8377	Approved
0.7937	Intermediate Similarity	NPD7507	Approved
0.7891	Intermediate Similarity	NPD7319	Approved
0.7647	Intermediate Similarity	NPD6686	Approved
0.7436	Intermediate Similarity	NPD5344	Discontinued
0.735	Intermediate Similarity	NPD7639	Approved
0.735	Intermediate Similarity	NPD7640	Approved
0.735	Intermediate Similarity	NPD6648	Approved
0.7273	Intermediate Similarity	NPD6412	Phase 2
0.7265	Intermediate Similarity	NPD7638	Approved
0.7209	Intermediate Similarity	NPD8513	Phase 3
0.72	Intermediate Similarity	NPD8133	Approved
0.7165	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD7524	Approved
0.712	Intermediate Similarity	NPD6053	Discontinued
0.7119	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD8515	Approved
0.7077	Intermediate Similarity	NPD8516	Approved
0.7077	Intermediate Similarity	NPD8517	Approved
0.7023	Intermediate Similarity	NPD6370	Approved
0.7015	Intermediate Similarity	NPD7736	Approved
0.6984	Remote Similarity	NPD6882	Approved
0.6975	Remote Similarity	NPD4225	Approved
0.694	Remote Similarity	NPD8293	Discontinued
0.6917	Remote Similarity	NPD7492	Approved
0.6899	Remote Similarity	NPD6009	Approved
0.6897	Remote Similarity	NPD7625	Phase 1
0.6897	Remote Similarity	NPD7637	Suspended
0.688	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6319	Approved
0.687	Remote Similarity	NPD6054	Approved
0.6866	Remote Similarity	NPD6616	Approved
0.685	Remote Similarity	NPD8297	Approved
0.6815	Remote Similarity	NPD7078	Approved
0.681	Remote Similarity	NPD7838	Discovery
0.6803	Remote Similarity	NPD7632	Discontinued
0.6797	Remote Similarity	NPD4632	Approved
0.6786	Remote Similarity	NPD6695	Phase 3
0.6772	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6059	Approved
0.6726	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6015	Approved
0.6692	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6642	Remote Similarity	NPD5988	Approved
0.6641	Remote Similarity	NPD6649	Approved
0.6641	Remote Similarity	NPD6650	Approved
0.664	Remote Similarity	NPD6675	Approved
0.664	Remote Similarity	NPD5739	Approved
0.664	Remote Similarity	NPD6402	Approved
0.664	Remote Similarity	NPD7128	Approved
0.6614	Remote Similarity	NPD6372	Approved
0.6614	Remote Similarity	NPD6373	Approved
0.6593	Remote Similarity	NPD8328	Phase 3
0.6587	Remote Similarity	NPD5697	Approved
0.6569	Remote Similarity	NPD8074	Phase 3
0.6562	Remote Similarity	NPD7290	Approved
0.6562	Remote Similarity	NPD6371	Approved
0.6562	Remote Similarity	NPD7102	Approved
0.6562	Remote Similarity	NPD6883	Approved
0.6552	Remote Similarity	NPD4250	Approved
0.6552	Remote Similarity	NPD4251	Approved
0.6552	Remote Similarity	NPD7750	Discontinued
0.6535	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7320	Approved
0.6525	Remote Similarity	NPD46	Approved
0.6525	Remote Similarity	NPD6698	Approved
0.6518	Remote Similarity	NPD6931	Approved
0.6518	Remote Similarity	NPD7514	Phase 3
0.6518	Remote Similarity	NPD6930	Phase 2
0.6512	Remote Similarity	NPD6847	Approved
0.6512	Remote Similarity	NPD8130	Phase 1
0.6512	Remote Similarity	NPD6617	Approved
0.6512	Remote Similarity	NPD6869	Approved
0.6484	Remote Similarity	NPD6013	Approved
0.6484	Remote Similarity	NPD6014	Approved
0.6484	Remote Similarity	NPD6012	Approved
0.6471	Remote Similarity	NPD6067	Discontinued
0.6471	Remote Similarity	NPD7604	Phase 2
0.6466	Remote Similarity	NPD4249	Approved
0.6457	Remote Similarity	NPD5701	Approved
0.6457	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4159	Approved
0.6444	Remote Similarity	NPD5983	Phase 2
0.6441	Remote Similarity	NPD6051	Approved
0.6429	Remote Similarity	NPD6929	Approved
0.6406	Remote Similarity	NPD6011	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.6391	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7260	Phase 2
0.6378	Remote Similarity	NPD6008	Approved
0.6377	Remote Similarity	NPD6336	Discontinued
0.6372	Remote Similarity	NPD7332	Phase 2
0.6341	Remote Similarity	NPD6083	Phase 2
0.6341	Remote Similarity	NPD6084	Phase 2
0.6339	Remote Similarity	NPD7145	Approved
0.6333	Remote Similarity	NPD7087	Discontinued
0.6328	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6902	Approved
0.6308	Remote Similarity	NPD4634	Approved
0.6299	Remote Similarity	NPD5141	Approved
0.6286	Remote Similarity	NPD6033	Approved
0.6281	Remote Similarity	NPD8171	Discontinued
0.6271	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6925	Approved
0.625	Remote Similarity	NPD5776	Phase 2
0.625	Remote Similarity	NPD6932	Approved
0.624	Remote Similarity	NPD5285	Approved
0.624	Remote Similarity	NPD5286	Approved
0.624	Remote Similarity	NPD4696	Approved
0.6239	Remote Similarity	NPD6893	Approved
0.6228	Remote Similarity	NPD4822	Approved
0.6228	Remote Similarity	NPD7525	Registered
0.6228	Remote Similarity	NPD4820	Approved
0.6228	Remote Similarity	NPD4819	Approved
0.6228	Remote Similarity	NPD4821	Approved
0.6228	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.621	Remote Similarity	NPD4755	Approved
0.6198	Remote Similarity	NPD5281	Approved
0.6198	Remote Similarity	NPD5284	Approved
0.6198	Remote Similarity	NPD7983	Approved
0.6179	Remote Similarity	NPD5695	Phase 3
0.6176	Remote Similarity	NPD7101	Approved
0.6176	Remote Similarity	NPD7100	Approved
0.6161	Remote Similarity	NPD6933	Approved
0.6148	Remote Similarity	NPD4202	Approved
0.6148	Remote Similarity	NPD6399	Phase 3
0.6148	Remote Similarity	NPD5779	Approved
0.6148	Remote Similarity	NPD5778	Approved
0.6145	Remote Similarity	NPD7799	Discontinued
0.6142	Remote Similarity	NPD5225	Approved
0.6142	Remote Similarity	NPD5226	Approved
0.6142	Remote Similarity	NPD4633	Approved
0.6142	Remote Similarity	NPD5224	Approved
0.6133	Remote Similarity	NPD7266	Discontinued
0.6129	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6640	Phase 3
0.6116	Remote Similarity	NPD5785	Approved
0.6115	Remote Similarity	NPD7830	Approved
0.6115	Remote Similarity	NPD7829	Approved
0.6111	Remote Similarity	NPD8338	Approved
0.6111	Remote Similarity	NPD4700	Approved
0.6111	Remote Similarity	NPD8449	Approved
0.6103	Remote Similarity	NPD6335	Approved
0.6095	Remote Similarity	NPD7685	Pre-registration
0.6094	Remote Similarity	NPD5174	Approved
0.6094	Remote Similarity	NPD5175	Approved
0.6087	Remote Similarity	NPD6921	Approved
0.6074	Remote Similarity	NPD6274	Approved
0.6069	Remote Similarity	NPD8450	Suspended
0.6068	Remote Similarity	NPD7154	Phase 3
0.6066	Remote Similarity	NPD6411	Approved
0.6063	Remote Similarity	NPD5223	Approved
0.6053	Remote Similarity	NPD4268	Approved
0.6053	Remote Similarity	NPD4271	Approved
0.6047	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6898	Phase 1
0.6032	Remote Similarity	NPD5696	Approved
0.6031	Remote Similarity	NPD4729	Approved
0.6031	Remote Similarity	NPD4730	Approved
0.6029	Remote Similarity	NPD6317	Approved
0.6028	Remote Similarity	NPD8451	Approved
0.6014	Remote Similarity	NPD7741	Discontinued
0.6	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD4768	Approved
0.5986	Remote Similarity	NPD8448	Approved
0.5985	Remote Similarity	NPD6314	Approved
0.5985	Remote Similarity	NPD6313	Approved
0.5984	Remote Similarity	NPD3168	Discontinued
0.5982	Remote Similarity	NPD6926	Approved
0.5982	Remote Similarity	NPD6924	Approved
0.5972	Remote Similarity	NPD8391	Approved
0.5972	Remote Similarity	NPD8392	Approved
0.5972	Remote Similarity	NPD8390	Approved
0.5972	Remote Similarity	NPD5956	Approved
0.5971	Remote Similarity	NPD6908	Approved
0.5971	Remote Similarity	NPD6909	Approved
0.5966	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD8299	Approved
0.5957	Remote Similarity	NPD8341	Approved
0.5957	Remote Similarity	NPD8342	Approved
0.5957	Remote Similarity	NPD8340	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