NPASS Compound

Structure

CID166884 OpenBabel06191715542D 34 38 0 0 1 0 0 0 0 0999 V2000 0.2653 -3.5238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9288 -0.0047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5331 -1.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7141 -2.8499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0385 -3.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9105 -3.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3178 -2.9145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2163 -3.8328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1263 -2.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6318 -3.0115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6537 -2.8035 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5276 -1.0228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7086 -2.7454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1318 -2.1454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1154 -1.8318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4508 -4.7340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4242 -4.8109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9343 -0.1093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9595 -3.1637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4518 -3.4145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1099 -1.9364 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 4.4627 -1.4023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 13 2 0 0 0 0 4 17 1 0 0 0 0 5 14 2 0 0 0 0 5 18 1 0 0 0 0 6 13 1 0 0 0 0 6 19 2 0 0 0 0 7 14 1 0 0 0 0 7 20 2 0 0 0 0 8 25 1 0 0 0 0 9 29 1 0 0 0 0 10 30 1 0 0 0 0 10 32 1 0 0 0 0 11 31 1 0 0 0 0 11 33 1 0 0 0 0 12 26 2 0 0 0 0 12 29 1 0 0 0 0 15 8 1 1 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 9 1 6 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 23 1 0 0 0 0 19 30 1 0 0 0 0 20 24 1 0 0 0 0 20 31 1 0 0 0 0 21 13 1 1 0 0 0 21 34 1 0 0 0 0 22 14 1 1 0 0 0 22 34 1 0 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.15
Volume:	450.325
LogP:	2.556
LogD:	2.935
LogS:	-4.689
# Rotatable Bonds:	8
TPSA:	111.14
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.601
Synthetic Accessibility Score:	4.072
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.85
MDCK Permeability:	3.71329442714341e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.53
Plasma Protein Binding (PPB):	80.0198974609375%
Volume Distribution (VD):	0.874
Pgp-substrate:	7.826112747192383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.123
CYP1A2-substrate:	0.791
CYP2C19-inhibitor:	0.73
CYP2C19-substrate:	0.705
CYP2C9-inhibitor:	0.71
CYP2C9-substrate:	0.747
CYP2D6-inhibitor:	0.909
CYP2D6-substrate:	0.318
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.841

ADMET: Excretion

Clearance (CL):	6.93
Half-life (T1/2):	0.286

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.239
Drug-inuced Liver Injury (DILI):	0.679
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.176
Skin Sensitization:	0.52
Carcinogencity:	0.724
Eye Corrosion:	0.003
Eye Irritation:	0.071
Respiratory Toxicity:	0.208

Download Data

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

Natural Product: NPC166884

Natural Product ID:	NPC166884
*Common Name:**	[(2S,3R,4R,5R)-4-(Hydroxymethyl)-2,5-Bis(7-Methoxy-1,3-Benzodioxol-5-Yl)Oxolan-3-Yl]Methyl Acetate
IUPAC Name:	[(2S,3R,4R,5R)-4-(hydroxymethyl)-2,5-bis(7-methoxy-1,3-benzodioxol-5-yl)oxolan-3-yl]methyl acetate
Synonyms:
Standard InCHIKey:	YPQDTAINIDFHAR-WWLNLUSPSA-N
Standard InCHI:	InChI=1S/C24H26O10/c1-12(26)29-9-16-15(8-25)21(13-4-17(27-2)23-19(6-13)30-10-32-23)34-22(16)14-5-18(28-3)24-20(7-14)31-11-33-24/h4-7,15-16,21-22,25H,8-11H2,1-3H3/t15-,16-,21-,22+/m0/s1
SMILES:	OC[C@H]1[C@H](COC(=O)C)[C@H](O[C@H]1c1cc(OC)c2c(c1)OCO2)c1cc(OC)c2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490350
PubChem CID:	11554672
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	bark	n.a.	PMID[11101460]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16309318]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499324]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16724842]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27184	Bonellia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17271	Aegialitis annulata	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27401	Aniba riparia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27135	Tubularia larynx	Species	Tubulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27362	Hypericum elodes	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28066	Aloe speciosa	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28133	Geigeria filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27439	Letharia vulpina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22405	Litsea monopetala	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13728	Metanarthecium luteoviride	Species	Nartheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19590	Daedaleopsis tricolor	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27953	Eugenia formosa	Species	Myrtaceae	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
EC50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	142.0	nM	PMID[474592]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	EC50	=	3100.0	nM	PMID[474592]

☑ 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 NPC166884 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	306
0.1-0.2	1253
0.2-0.3	3418
0.3-0.4	8247
0.4-0.5	10615
0.5-0.6	5147
0.6-0.7	9271
0.7-0.8	3541
0.8-0.85	572
0.85-0.9	278
0.9-0.95	43
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477701
1.0	High Similarity	NPC141569
0.9853	High Similarity	NPC287124
0.9706	High Similarity	NPC46591
0.9571	High Similarity	NPC212890
0.9562	High Similarity	NPC56091
0.95	High Similarity	NPC477702
0.9485	High Similarity	NPC11453
0.9416	High Similarity	NPC283949
0.9412	High Similarity	NPC25333
0.9412	High Similarity	NPC49235
0.9412	High Similarity	NPC148893
0.9412	High Similarity	NPC150534
0.9375	High Similarity	NPC164082
0.9357	High Similarity	NPC12728
0.9357	High Similarity	NPC185071
0.9338	High Similarity	NPC31530
0.9306	High Similarity	NPC473989
0.9281	High Similarity	NPC226547
0.9275	High Similarity	NPC185908
0.927	High Similarity	NPC189474
0.9236	High Similarity	NPC477698
0.922	High Similarity	NPC255566
0.922	High Similarity	NPC298317
0.9209	High Similarity	NPC113550
0.9203	High Similarity	NPC143895
0.9197	High Similarity	NPC47181
0.9191	High Similarity	NPC72046
0.9191	High Similarity	NPC261812
0.9191	High Similarity	NPC65183
0.9178	High Similarity	NPC56184
0.9167	High Similarity	NPC316676
0.9167	High Similarity	NPC325720
0.9155	High Similarity	NPC92693
0.9155	High Similarity	NPC218841
0.9143	High Similarity	NPC177868
0.913	High Similarity	NPC18576
0.913	High Similarity	NPC236522
0.9124	High Similarity	NPC196937
0.9124	High Similarity	NPC266848
0.9124	High Similarity	NPC136750
0.9078	High Similarity	NPC312199
0.9065	High Similarity	NPC121651
0.9054	High Similarity	NPC136757
0.9054	High Similarity	NPC312763
0.9028	High Similarity	NPC3982
0.9028	High Similarity	NPC193779
0.9021	High Similarity	NPC177644
0.9021	High Similarity	NPC191158
0.9014	High Similarity	NPC40237
0.9014	High Similarity	NPC151423
0.9007	High Similarity	NPC96593
0.9	High Similarity	NPC469981
0.9	High Similarity	NPC474039
0.8978	High Similarity	NPC192255
0.8978	High Similarity	NPC227160
0.8978	High Similarity	NPC82111
0.8973	High Similarity	NPC474965
0.8973	High Similarity	NPC477695
0.8973	High Similarity	NPC668
0.8973	High Similarity	NPC293757
0.8973	High Similarity	NPC174512
0.8958	High Similarity	NPC475868
0.8951	High Similarity	NPC218510
0.8951	High Similarity	NPC474808
0.8951	High Similarity	NPC76415
0.8947	High Similarity	NPC288149
0.8944	High Similarity	NPC471908
0.8936	High Similarity	NPC88640
0.8936	High Similarity	NPC123526
0.8936	High Similarity	NPC193666
0.8933	High Similarity	NPC32373
0.8933	High Similarity	NPC237946
0.8926	High Similarity	NPC198461
0.8919	High Similarity	NPC302610
0.8919	High Similarity	NPC477699
0.8913	High Similarity	NPC147616
0.8913	High Similarity	NPC259742
0.8913	High Similarity	NPC219671
0.8913	High Similarity	NPC104077
0.8905	High Similarity	NPC271208
0.8905	High Similarity	NPC233224
0.8904	High Similarity	NPC248132
0.8904	High Similarity	NPC130449
0.8897	High Similarity	NPC54321
0.8897	High Similarity	NPC328682
0.8897	High Similarity	NPC281864
0.8889	High Similarity	NPC239254
0.8889	High Similarity	NPC118385
0.8889	High Similarity	NPC472713
0.8889	High Similarity	NPC475000
0.8889	High Similarity	NPC326144
0.8889	High Similarity	NPC473046
0.8889	High Similarity	NPC472712
0.8889	High Similarity	NPC172171
0.8889	High Similarity	NPC187774
0.8881	High Similarity	NPC210354
0.8881	High Similarity	NPC176586
0.8881	High Similarity	NPC474295
0.8874	High Similarity	NPC207584
0.8874	High Similarity	NPC19947
0.8865	High Similarity	NPC101807
0.8859	High Similarity	NPC24562
0.8857	High Similarity	NPC24490
0.8857	High Similarity	NPC141765
0.8857	High Similarity	NPC165155
0.8857	High Similarity	NPC34103
0.8851	High Similarity	NPC477700
0.8851	High Similarity	NPC224472
0.8851	High Similarity	NPC475756
0.8849	High Similarity	NPC1474
0.8844	High Similarity	NPC55158
0.8844	High Similarity	NPC145569
0.8844	High Similarity	NPC85141
0.8844	High Similarity	NPC216223
0.8844	High Similarity	NPC55715
0.8844	High Similarity	NPC240521
0.8844	High Similarity	NPC95392
0.8844	High Similarity	NPC35877
0.8844	High Similarity	NPC51328
0.8844	High Similarity	NPC286235
0.8832	High Similarity	NPC476748
0.8828	High Similarity	NPC327651
0.8828	High Similarity	NPC318286
0.8828	High Similarity	NPC180953
0.8824	High Similarity	NPC8050
0.8824	High Similarity	NPC473093
0.8824	High Similarity	NPC473092
0.8819	High Similarity	NPC324962
0.8819	High Similarity	NPC474288
0.8803	High Similarity	NPC9068
0.8803	High Similarity	NPC156376
0.88	High Similarity	NPC473425
0.8794	High Similarity	NPC25695
0.8794	High Similarity	NPC172818
0.8792	High Similarity	NPC471154
0.8786	High Similarity	NPC244983
0.8786	High Similarity	NPC326095
0.8784	High Similarity	NPC24425
0.8777	High Similarity	NPC129687
0.8777	High Similarity	NPC7744
0.8777	High Similarity	NPC33611
0.8777	High Similarity	NPC171928
0.8777	High Similarity	NPC158526
0.8777	High Similarity	NPC100223
0.8777	High Similarity	NPC16830
0.8768	High Similarity	NPC134764
0.8768	High Similarity	NPC171550
0.8767	High Similarity	NPC321696
0.8767	High Similarity	NPC321958
0.8759	High Similarity	NPC226862
0.8759	High Similarity	NPC82862
0.8759	High Similarity	NPC179521
0.8759	High Similarity	NPC158471
0.8759	High Similarity	NPC165128
0.8759	High Similarity	NPC222127
0.8759	High Similarity	NPC57119
0.8758	High Similarity	NPC150943
0.8758	High Similarity	NPC119910
0.8758	High Similarity	NPC268718
0.8758	High Similarity	NPC91634
0.875	High Similarity	NPC472714
0.875	High Similarity	NPC311057
0.875	High Similarity	NPC229172
0.875	High Similarity	NPC230538
0.875	High Similarity	NPC246947
0.875	High Similarity	NPC36531
0.875	High Similarity	NPC103637
0.875	High Similarity	NPC5262
0.8742	High Similarity	NPC186316
0.8741	High Similarity	NPC103448
0.8741	High Similarity	NPC216434
0.8733	High Similarity	NPC308739
0.8733	High Similarity	NPC53669
0.8733	High Similarity	NPC126405
0.8733	High Similarity	NPC297271
0.8733	High Similarity	NPC77237
0.8733	High Similarity	NPC217708
0.8733	High Similarity	NPC474606
0.8733	High Similarity	NPC16791
0.8733	High Similarity	NPC245948
0.8725	High Similarity	NPC210642
0.8725	High Similarity	NPC32079
0.8725	High Similarity	NPC13985
0.8725	High Similarity	NPC303519
0.8723	High Similarity	NPC135777
0.8723	High Similarity	NPC99572
0.8723	High Similarity	NPC474139
0.8723	High Similarity	NPC174191
0.8723	High Similarity	NPC142547
0.8723	High Similarity	NPC126409
0.8716	High Similarity	NPC262455
0.8716	High Similarity	NPC177476
0.8716	High Similarity	NPC125570
0.8714	High Similarity	NPC58585
0.8707	High Similarity	NPC39657
0.8701	High Similarity	NPC152424
0.8701	High Similarity	NPC100465
0.8701	High Similarity	NPC115624
0.8699	High Similarity	NPC205316

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 NPC166884 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	812
0.2-0.3	1823
0.3-0.4	2733
0.4-0.5	1887
0.5-0.6	1077
0.6-0.7	493
0.7-0.8	71
0.8-0.85	6
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8933	High Similarity	NPD4965	Approved
0.8933	High Similarity	NPD4967	Phase 2
0.8933	High Similarity	NPD4966	Approved
0.8733	High Similarity	NPD37	Approved
0.8693	High Similarity	NPD6234	Discontinued
0.8428	Intermediate Similarity	NPD7228	Approved
0.8344	Intermediate Similarity	NPD7199	Phase 2
0.8298	Intermediate Similarity	NPD3027	Phase 3
0.8221	Intermediate Similarity	NPD7240	Approved
0.8125	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD3705	Approved
0.7961	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1653	Approved
0.78	Intermediate Similarity	NPD7266	Discontinued
0.7755	Intermediate Similarity	NPD1613	Approved
0.7755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7647	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1357	Approved
0.7622	Intermediate Similarity	NPD2982	Phase 2
0.7622	Intermediate Similarity	NPD2983	Phase 2
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.7582	Intermediate Similarity	NPD6674	Discontinued
0.7556	Intermediate Similarity	NPD7680	Approved
0.7552	Intermediate Similarity	NPD2981	Phase 2
0.7534	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3018	Phase 2
0.7528	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7423	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4110	Phase 3
0.7399	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7054	Approved
0.7383	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4908	Phase 1
0.7362	Intermediate Similarity	NPD3817	Phase 2
0.7362	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7472	Approved
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5844	Phase 1
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7267	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7685	Pre-registration
0.7267	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.7261	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1610	Phase 2
0.7241	Intermediate Similarity	NPD1091	Approved
0.7239	Intermediate Similarity	NPD1934	Approved
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD5763	Approved
0.7226	Intermediate Similarity	NPD5762	Approved
0.7225	Intermediate Similarity	NPD7808	Phase 3
0.7215	Intermediate Similarity	NPD5058	Phase 3
0.7209	Intermediate Similarity	NPD6797	Phase 2
0.7202	Intermediate Similarity	NPD6232	Discontinued
0.7195	Intermediate Similarity	NPD8455	Phase 2
0.7188	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5494	Approved
0.7181	Intermediate Similarity	NPD2861	Phase 2
0.7176	Intermediate Similarity	NPD7473	Discontinued
0.7171	Intermediate Similarity	NPD4140	Approved
0.7171	Intermediate Similarity	NPD3620	Phase 2
0.7171	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7251	Discontinued
0.716	Intermediate Similarity	NPD4005	Discontinued
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7134	Intermediate Similarity	NPD4236	Phase 3
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7134	Intermediate Similarity	NPD4237	Approved
0.7124	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5124	Phase 1
0.7118	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6166	Phase 2
0.7118	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7028	Phase 2
0.7115	Intermediate Similarity	NPD1375	Discontinued
0.7114	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3882	Suspended
0.7095	Intermediate Similarity	NPD7296	Approved
0.7091	Intermediate Similarity	NPD2977	Approved
0.7091	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2978	Approved
0.7089	Intermediate Similarity	NPD4628	Phase 3
0.7086	Intermediate Similarity	NPD7095	Approved
0.7078	Intermediate Similarity	NPD6653	Approved
0.7075	Intermediate Similarity	NPD1608	Approved
0.7063	Intermediate Similarity	NPD4357	Discontinued
0.7051	Intermediate Similarity	NPD2438	Suspended
0.7044	Intermediate Similarity	NPD6190	Approved
0.7039	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7549	Discontinued
0.7027	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4749	Approved
0.7022	Intermediate Similarity	NPD6843	Phase 3
0.7022	Intermediate Similarity	NPD6841	Approved
0.7022	Intermediate Similarity	NPD6842	Approved
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5536	Phase 2
0.7013	Intermediate Similarity	NPD230	Phase 1
0.7011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD3540	Phase 1
0.7006	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6005	Phase 3
0.7006	Intermediate Similarity	NPD6004	Phase 3
0.7006	Intermediate Similarity	NPD6002	Phase 3
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD7124	Phase 2
0.6994	Remote Similarity	NPD3686	Approved
0.6994	Remote Similarity	NPD3687	Approved
0.6993	Remote Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD7157	Approved
0.6988	Remote Similarity	NPD7819	Suspended
0.6988	Remote Similarity	NPD2801	Approved
0.6988	Remote Similarity	NPD1465	Phase 2
0.6986	Remote Similarity	NPD5126	Approved
0.6986	Remote Similarity	NPD5125	Phase 3
0.6975	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1548	Phase 1
0.6962	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5242	Approved
0.695	Remote Similarity	NPD228	Approved
0.6946	Remote Similarity	NPD5353	Approved
0.6943	Remote Similarity	NPD3539	Phase 1
0.6937	Remote Similarity	NPD2219	Phase 1
0.6937	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3384	Approved
0.6928	Remote Similarity	NPD3382	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6928	Remote Similarity	NPD3383	Approved
0.6923	Remote Similarity	NPD6111	Discontinued
0.6918	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5585	Approved
0.6914	Remote Similarity	NPD2533	Approved
0.6914	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD2534	Approved
0.6909	Remote Similarity	NPD4678	Approved
0.6909	Remote Similarity	NPD4380	Phase 2
0.6909	Remote Similarity	NPD4675	Approved
0.6903	Remote Similarity	NPD5735	Approved
0.6901	Remote Similarity	NPD5535	Approved
0.6901	Remote Similarity	NPD3787	Discontinued
0.6901	Remote Similarity	NPD7843	Approved
0.6897	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4210	Discontinued
0.6886	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4108	Discontinued
0.6879	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD5588	Approved
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3892	Phase 2
0.6875	Remote Similarity	NPD6331	Phase 2
0.6871	Remote Similarity	NPD17	Approved
0.6867	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1283	Approved
0.6864	Remote Similarity	NPD7075	Discontinued
0.6863	Remote Similarity	NPD4625	Phase 3
0.6857	Remote Similarity	NPD2684	Approved
0.6852	Remote Similarity	NPD6799	Approved
0.6845	Remote Similarity	NPD5006	Approved
0.6845	Remote Similarity	NPD5005	Approved
0.6845	Remote Similarity	NPD5402	Approved
0.6839	Remote Similarity	NPD2979	Phase 3
0.6839	Remote Similarity	NPD2238	Phase 2
0.6835	Remote Similarity	NPD2161	Phase 2
0.6835	Remote Similarity	NPD6032	Approved
0.6826	Remote Similarity	NPD6801	Discontinued
0.6824	Remote Similarity	NPD919	Approved
0.6824	Remote Similarity	NPD3847	Discontinued
0.6815	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4536	Approved
0.6815	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4538	Approved
0.6813	Remote Similarity	NPD3060	Approved
0.6813	Remote Similarity	NPD5177	Phase 3
0.6809	Remote Similarity	NPD3021	Approved
0.6809	Remote Similarity	NPD3022	Approved
0.6807	Remote Similarity	NPD6599	Discontinued
0.6803	Remote Similarity	NPD5691	Approved
0.6795	Remote Similarity	NPD3657	Discovery
0.679	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7827	Phase 1
0.6786	Remote Similarity	NPD1358	Approved
0.6774	Remote Similarity	NPD4062	Phase 3
0.677	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3750	Approved
0.6763	Remote Similarity	NPD3926	Phase 2
0.6757	Remote Similarity	NPD4626	Approved
0.675	Remote Similarity	NPD5958	Discontinued
0.6748	Remote Similarity	NPD1511	Approved
0.674	Remote Similarity	NPD7243	Clinical (unspecified phase)

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