NPASS Compound

Structure

CID22149 OpenBabel06191715352D 27 29 0 0 1 0 0 0 0 0999 V2000 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1369 3.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 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 -2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4459 4.1723 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 2.5981 -0.5000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 1 0 0 0 0 2 7 2 0 0 0 0 3 8 1 0 0 0 0 4 7 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 9 2 0 0 0 0 6 25 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 9 15 1 0 0 0 0 10 5 1 1 0 0 0 10 12 1 0 0 0 0 10 26 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 6 0 0 0 13 14 1 0 0 0 0 13 21 1 1 0 0 0 14 17 1 0 0 0 0 14 22 1 6 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 16 27 1 6 0 0 0 17 26 1 0 0 0 0 17 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.14
Volume:	356.912
LogP:	-0.414
LogD:	-0.179
LogS:	-0.987
# Rotatable Bonds:	6
TPSA:	155.14
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	4.635
Fsp3:	0.706
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.645
MDCK Permeability:	0.00011256411380600184
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.658
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.315
Plasma Protein Binding (PPB):	27.543272018432617%
Volume Distribution (VD):	0.366
Pgp-substrate:	57.21311569213867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.226
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	1.536
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.239
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.153
Skin Sensitization:	0.103
Carcinogencity:	0.95
Eye Corrosion:	0.003
Eye Irritation:	0.082
Respiratory Toxicity:	0.378

Download Data

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

Natural Product: NPC22149

Natural Product ID:	NPC22149
*Common Name:**	Methyl (1S)-7-(Hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-1,4A,5,7A-Tetrahydrocyclopenta[C]Pyran-4-Carboxylate
IUPAC Name:	methyl (1S)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:
Standard InCHIKey:	IBFYXTRXDNAPMM-QZTNVZDFSA-N
Standard InCHI:	InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8?,10-,11?,12-,13+,14-,16+,17+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C(C3C2C(=CC3)CO)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1718933
PubChem CID:	16760120
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
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[17340259]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562611]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28836430]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[29140705]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10008	Tinospora capillipes	Species	Menispermaceae	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
Potency	4

Activity Type	# Activity
Individual Protein	3
PROTEIN COMPLEX	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	23099.9	nM	PMID[507131]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[507131]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	73.1	nM	PMID[507131]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[507131]

☑ 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 NPC22149 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	195
0.1-0.2	1291
0.2-0.3	4598
0.3-0.4	8827
0.4-0.5	14682
0.5-0.6	8570
0.6-0.7	4044
0.7-0.8	411
0.8-0.85	36
0.85-0.9	17
0.9-0.95	11
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC306344
1.0	High Similarity	NPC255677
0.9892	High Similarity	NPC298255
0.9892	High Similarity	NPC28304
0.9684	High Similarity	NPC267869
0.9684	High Similarity	NPC234304
0.9684	High Similarity	NPC197541
0.9684	High Similarity	NPC284929
0.9684	High Similarity	NPC118761
0.9674	High Similarity	NPC241911
0.9583	High Similarity	NPC86095
0.9579	High Similarity	NPC261117
0.9579	High Similarity	NPC222062
0.9579	High Similarity	NPC250545
0.9579	High Similarity	NPC310804
0.9375	High Similarity	NPC13171
0.9375	High Similarity	NPC195510
0.914	High Similarity	NPC61201
0.8925	High Similarity	NPC303451
0.8925	High Similarity	NPC6414
0.8812	High Similarity	NPC254538
0.8812	High Similarity	NPC474285
0.8723	High Similarity	NPC117596
0.8632	High Similarity	NPC472125
0.8632	High Similarity	NPC472124
0.8632	High Similarity	NPC472126
0.8602	High Similarity	NPC142583
0.8557	High Similarity	NPC469543
0.8557	High Similarity	NPC170204
0.8526	High Similarity	NPC65665
0.8526	High Similarity	NPC307699
0.8526	High Similarity	NPC216826
0.8526	High Similarity	NPC120021
0.8526	High Similarity	NPC231710
0.8526	High Similarity	NPC270908
0.8526	High Similarity	NPC470573
0.85	High Similarity	NPC20673
0.8416	Intermediate Similarity	NPC471599
0.84	Intermediate Similarity	NPC244878
0.837	Intermediate Similarity	NPC188717
0.837	Intermediate Similarity	NPC211455
0.8367	Intermediate Similarity	NPC101051
0.8333	Intermediate Similarity	NPC475928
0.8317	Intermediate Similarity	NPC219038
0.83	Intermediate Similarity	NPC151093
0.8283	Intermediate Similarity	NPC306041
0.8283	Intermediate Similarity	NPC161293
0.828	Intermediate Similarity	NPC136699
0.828	Intermediate Similarity	NPC220167
0.8235	Intermediate Similarity	NPC177013
0.8235	Intermediate Similarity	NPC35185
0.8235	Intermediate Similarity	NPC4899
0.8235	Intermediate Similarity	NPC474730
0.8235	Intermediate Similarity	NPC106668
0.8173	Intermediate Similarity	NPC170432
0.8163	Intermediate Similarity	NPC280390
0.8155	Intermediate Similarity	NPC27687
0.8155	Intermediate Similarity	NPC37240
0.8137	Intermediate Similarity	NPC98859
0.8137	Intermediate Similarity	NPC4637
0.8137	Intermediate Similarity	NPC287539
0.8137	Intermediate Similarity	NPC3488
0.8119	Intermediate Similarity	NPC472015
0.8095	Intermediate Similarity	NPC80338
0.8095	Intermediate Similarity	NPC148270
0.8095	Intermediate Similarity	NPC197813
0.8061	Intermediate Similarity	NPC9447
0.802	Intermediate Similarity	NPC472290
0.8019	Intermediate Similarity	NPC110701
0.8	Intermediate Similarity	NPC470124
0.8	Intermediate Similarity	NPC127235
0.798	Intermediate Similarity	NPC320552
0.798	Intermediate Similarity	NPC472196
0.798	Intermediate Similarity	NPC238090
0.798	Intermediate Similarity	NPC472195
0.7959	Intermediate Similarity	NPC327253
0.7941	Intermediate Similarity	NPC473307
0.7938	Intermediate Similarity	NPC137368
0.7921	Intermediate Similarity	NPC54731
0.79	Intermediate Similarity	NPC159698
0.79	Intermediate Similarity	NPC63897
0.7895	Intermediate Similarity	NPC266718
0.7895	Intermediate Similarity	NPC475035
0.7879	Intermediate Similarity	NPC472197
0.7879	Intermediate Similarity	NPC477749
0.787	Intermediate Similarity	NPC193741
0.7864	Intermediate Similarity	NPC473146
0.7843	Intermediate Similarity	NPC153559
0.7835	Intermediate Similarity	NPC475037
0.7822	Intermediate Similarity	NPC291709
0.7822	Intermediate Similarity	NPC241407
0.7812	Intermediate Similarity	NPC470658
0.7767	Intermediate Similarity	NPC124181
0.7727	Intermediate Similarity	NPC475924
0.7727	Intermediate Similarity	NPC475851
0.7723	Intermediate Similarity	NPC2003
0.7723	Intermediate Similarity	NPC475927
0.7723	Intermediate Similarity	NPC25701
0.7723	Intermediate Similarity	NPC475832
0.7714	Intermediate Similarity	NPC304163
0.7714	Intermediate Similarity	NPC201191
0.77	Intermediate Similarity	NPC472199
0.7685	Intermediate Similarity	NPC392
0.7685	Intermediate Similarity	NPC177524
0.7685	Intermediate Similarity	NPC219900
0.7677	Intermediate Similarity	NPC477748
0.7677	Intermediate Similarity	NPC249408
0.7677	Intermediate Similarity	NPC104129
0.7652	Intermediate Similarity	NPC470829
0.7652	Intermediate Similarity	NPC473228
0.7629	Intermediate Similarity	NPC475034
0.7624	Intermediate Similarity	NPC320089
0.76	Intermediate Similarity	NPC202886
0.7596	Intermediate Similarity	NPC307517
0.7596	Intermediate Similarity	NPC40182
0.7596	Intermediate Similarity	NPC169468
0.7596	Intermediate Similarity	NPC81483
0.7596	Intermediate Similarity	NPC90819
0.7596	Intermediate Similarity	NPC61630
0.7596	Intermediate Similarity	NPC198422
0.7573	Intermediate Similarity	NPC256230
0.7549	Intermediate Similarity	NPC71589
0.7549	Intermediate Similarity	NPC472198
0.7549	Intermediate Similarity	NPC256368
0.7549	Intermediate Similarity	NPC294293
0.7547	Intermediate Similarity	NPC80144
0.7544	Intermediate Similarity	NPC475309
0.7544	Intermediate Similarity	NPC13710
0.7525	Intermediate Similarity	NPC274274
0.7525	Intermediate Similarity	NPC473150
0.7525	Intermediate Similarity	NPC294643
0.7525	Intermediate Similarity	NPC473321
0.7523	Intermediate Similarity	NPC475960
0.75	Intermediate Similarity	NPC476613
0.75	Intermediate Similarity	NPC474194
0.75	Intermediate Similarity	NPC93190
0.75	Intermediate Similarity	NPC476612
0.75	Intermediate Similarity	NPC41681
0.75	Intermediate Similarity	NPC50464
0.7477	Intermediate Similarity	NPC197736
0.7476	Intermediate Similarity	NPC36954
0.7476	Intermediate Similarity	NPC93869
0.7476	Intermediate Similarity	NPC6765
0.7475	Intermediate Similarity	NPC74139
0.7475	Intermediate Similarity	NPC118077
0.7475	Intermediate Similarity	NPC475186
0.7474	Intermediate Similarity	NPC127295
0.7474	Intermediate Similarity	NPC163362
0.7458	Intermediate Similarity	NPC318135
0.7453	Intermediate Similarity	NPC67296
0.7453	Intermediate Similarity	NPC198992
0.7453	Intermediate Similarity	NPC476611
0.7451	Intermediate Similarity	NPC475912
0.7449	Intermediate Similarity	NPC21469
0.7449	Intermediate Similarity	NPC477746
0.7449	Intermediate Similarity	NPC477747
0.7434	Intermediate Similarity	NPC472274
0.7429	Intermediate Similarity	NPC37866
0.7429	Intermediate Similarity	NPC249171
0.7429	Intermediate Similarity	NPC49833
0.7426	Intermediate Similarity	NPC474232
0.7426	Intermediate Similarity	NPC473619
0.7426	Intermediate Similarity	NPC118078
0.7423	Intermediate Similarity	NPC142111
0.7423	Intermediate Similarity	NPC473315
0.7407	Intermediate Similarity	NPC474917
0.74	Intermediate Similarity	NPC473151
0.74	Intermediate Similarity	NPC473715
0.74	Intermediate Similarity	NPC470137
0.7387	Intermediate Similarity	NPC83005
0.7383	Intermediate Similarity	NPC86077
0.7379	Intermediate Similarity	NPC274588
0.7368	Intermediate Similarity	NPC277583
0.7368	Intermediate Similarity	NPC323472
0.7368	Intermediate Similarity	NPC321728
0.7364	Intermediate Similarity	NPC473807
0.7358	Intermediate Similarity	NPC469402
0.7353	Intermediate Similarity	NPC470373
0.7353	Intermediate Similarity	NPC470379
0.735	Intermediate Similarity	NPC202051
0.7347	Intermediate Similarity	NPC212363
0.7347	Intermediate Similarity	NPC473308
0.7345	Intermediate Similarity	NPC293658
0.7345	Intermediate Similarity	NPC264153
0.7345	Intermediate Similarity	NPC474410
0.7339	Intermediate Similarity	NPC153095
0.7339	Intermediate Similarity	NPC243998
0.7339	Intermediate Similarity	NPC223450
0.7339	Intermediate Similarity	NPC85670
0.7333	Intermediate Similarity	NPC236580
0.7333	Intermediate Similarity	NPC304445
0.7328	Intermediate Similarity	NPC219656
0.732	Intermediate Similarity	NPC251026
0.7315	Intermediate Similarity	NPC151516
0.7315	Intermediate Similarity	NPC473148
0.7308	Intermediate Similarity	NPC14961
0.7308	Intermediate Similarity	NPC471142
0.7308	Intermediate Similarity	NPC270013
0.7297	Intermediate Similarity	NPC257853
0.7297	Intermediate Similarity	NPC118225

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 NPC22149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1663
0.2-0.3	3853
0.3-0.4	2318
0.4-0.5	828
0.5-0.6	260
0.6-0.7	63
0.7-0.8	3
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
0.7685	Intermediate Similarity	NPD6686	Approved
0.7426	Intermediate Similarity	NPD46	Approved
0.7426	Intermediate Similarity	NPD6698	Approved
0.7264	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD8513	Phase 3
0.7168	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7503	Approved
0.7059	Intermediate Similarity	NPD8516	Approved
0.7059	Intermediate Similarity	NPD8517	Approved
0.7059	Intermediate Similarity	NPD8515	Approved
0.6967	Remote Similarity	NPD7507	Approved
0.6863	Remote Similarity	NPD4249	Approved
0.6857	Remote Similarity	NPD7983	Approved
0.6814	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6053	Discontinued
0.68	Remote Similarity	NPD7319	Approved
0.6796	Remote Similarity	NPD4250	Approved
0.6796	Remote Similarity	NPD4251	Approved
0.6783	Remote Similarity	NPD6371	Approved
0.6762	Remote Similarity	NPD7838	Discovery
0.6733	Remote Similarity	NPD7154	Phase 3
0.6733	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6412	Phase 2
0.6639	Remote Similarity	NPD8033	Approved
0.6612	Remote Similarity	NPD7516	Approved
0.6557	Remote Similarity	NPD8294	Approved
0.6557	Remote Similarity	NPD8377	Approved
0.6508	Remote Similarity	NPD8074	Phase 3
0.6504	Remote Similarity	NPD8380	Approved
0.6504	Remote Similarity	NPD8379	Approved
0.6504	Remote Similarity	NPD8296	Approved
0.6504	Remote Similarity	NPD8378	Approved
0.6504	Remote Similarity	NPD8335	Approved
0.6486	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD8133	Approved
0.6455	Remote Similarity	NPD7839	Suspended
0.6436	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5362	Discontinued
0.64	Remote Similarity	NPD7642	Approved
0.6393	Remote Similarity	NPD7641	Discontinued
0.6389	Remote Similarity	NPD7637	Suspended
0.6372	Remote Similarity	NPD5344	Discontinued
0.6371	Remote Similarity	NPD8444	Approved
0.6355	Remote Similarity	NPD1695	Approved
0.633	Remote Similarity	NPD5778	Approved
0.633	Remote Similarity	NPD5779	Approved
0.6311	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7115	Discovery
0.6299	Remote Similarity	NPD8451	Approved
0.6286	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7639	Approved
0.6283	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD8448	Approved
0.6238	Remote Similarity	NPD4271	Approved
0.6238	Remote Similarity	NPD4268	Approved
0.622	Remote Similarity	NPD8299	Approved
0.622	Remote Similarity	NPD8342	Approved
0.622	Remote Similarity	NPD8341	Approved
0.622	Remote Similarity	NPD8340	Approved
0.6216	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7638	Approved
0.619	Remote Similarity	NPD8080	Discontinued
0.6147	Remote Similarity	NPD5785	Approved
0.6142	Remote Similarity	NPD8328	Phase 3
0.6134	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5282	Discontinued
0.6121	Remote Similarity	NPD1407	Approved
0.6117	Remote Similarity	NPD4820	Approved
0.6117	Remote Similarity	NPD4819	Approved
0.6117	Remote Similarity	NPD4822	Approved
0.6117	Remote Similarity	NPD4821	Approved
0.6111	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD8392	Approved
0.6107	Remote Similarity	NPD8390	Approved
0.6107	Remote Similarity	NPD8391	Approved
0.6078	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7736	Approved
0.6074	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6370	Approved
0.6048	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6009	Approved
0.6032	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD6435	Approved
0.5984	Remote Similarity	NPD6882	Approved
0.5981	Remote Similarity	NPD5363	Approved
0.5969	Remote Similarity	NPD7492	Approved
0.5962	Remote Similarity	NPD4252	Approved
0.5954	Remote Similarity	NPD8336	Approved
0.5954	Remote Similarity	NPD8337	Approved
0.5943	Remote Similarity	NPD5331	Approved
0.5943	Remote Similarity	NPD5332	Approved
0.594	Remote Similarity	NPD7260	Phase 2
0.5935	Remote Similarity	NPD4632	Approved
0.5926	Remote Similarity	NPD5786	Approved
0.5923	Remote Similarity	NPD6616	Approved
0.5909	Remote Similarity	NPD6101	Approved
0.5909	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6054	Approved
0.5905	Remote Similarity	NPD4790	Discontinued
0.5878	Remote Similarity	NPD7078	Approved
0.5876	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7524	Approved
0.5859	Remote Similarity	NPD6015	Approved
0.5859	Remote Similarity	NPD6016	Approved
0.5854	Remote Similarity	NPD8297	Approved
0.5849	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD4270	Approved
0.5849	Remote Similarity	NPD4269	Approved
0.5849	Remote Similarity	NPD5209	Approved
0.582	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6421	Discontinued
0.5814	Remote Similarity	NPD5988	Approved
0.581	Remote Similarity	NPD5368	Approved
0.5804	Remote Similarity	NPD6411	Approved
0.5781	Remote Similarity	NPD6059	Approved
0.5778	Remote Similarity	NPD8338	Approved
0.5772	Remote Similarity	NPD2204	Approved
0.5763	Remote Similarity	NPD7632	Discontinued
0.5752	Remote Similarity	NPD6399	Phase 3
0.5741	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD897	Approved
0.5714	Remote Similarity	NPD898	Approved
0.5714	Remote Similarity	NPD896	Approved
0.5702	Remote Similarity	NPD5697	Approved
0.5682	Remote Similarity	NPD8273	Phase 1
0.5673	Remote Similarity	NPD4756	Discovery
0.5669	Remote Similarity	NPD7500	Approved
0.5662	Remote Similarity	NPD6845	Suspended
0.566	Remote Similarity	NPD7332	Phase 2
0.5656	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6899	Approved
0.5656	Remote Similarity	NPD6881	Approved
0.5652	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6695	Phase 3
0.5645	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD6649	Approved
0.5645	Remote Similarity	NPD6650	Approved
0.562	Remote Similarity	NPD6640	Phase 3
0.562	Remote Similarity	NPD6402	Approved
0.562	Remote Similarity	NPD7128	Approved
0.562	Remote Similarity	NPD5739	Approved
0.562	Remote Similarity	NPD6675	Approved
0.5617	Remote Similarity	NPD7685	Pre-registration
0.5615	Remote Similarity	NPD5983	Phase 2
0.561	Remote Similarity	NPD6014	Approved
0.561	Remote Similarity	NPD6372	Approved
0.561	Remote Similarity	NPD6013	Approved
0.561	Remote Similarity	NPD6373	Approved
0.561	Remote Similarity	NPD6012	Approved
0.5607	Remote Similarity	NPD5369	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