NPASS Compound

Structure

CID304163 OpenBabel06191716112D 25 27 0 0 1 0 0 0 0 0999 V2000 3.0029 1.7213 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 5.0733 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 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 4.3301 -1.5000 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 3.4641 -0.0000 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 -0.0000 -2.0000 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 2.5981 -0.5000 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 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 -1.7321 -2.0000 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 -1.3090 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 0.0000 -0.0000 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 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 16 1 0 0 0 0 4 8 1 0 0 0 0 4 17 2 0 0 0 0 5 18 1 0 0 0 0 6 8 2 0 0 0 0 6 23 1 0 0 0 0 7 1 1 6 0 0 0 7 10 1 0 0 0 0 8 16 1 0 0 0 0 9 5 1 1 0 0 0 9 11 1 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 6 0 0 0 11 12 1 0 0 0 0 11 19 1 6 0 0 0 12 13 1 0 0 0 0 12 20 1 1 0 0 0 13 15 1 0 0 0 0 13 21 1 6 0 0 0 14 23 1 0 0 0 0 14 25 1 1 0 0 0 15 24 1 0 0 0 0 15 25 1 1 0 0 0 16 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.14
Volume:	333.462
LogP:	-0.575
LogD:	-0.05
LogS:	-1.908
# Rotatable Bonds:	4
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	4.945
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.988
MDCK Permeability:	9.658019553171471e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.147
Human Intestinal Absorption (HIA):	0.905
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	28.063215255737305%
Volume Distribution (VD):	0.456
Pgp-substrate:	55.54209899902344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.452
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	1.066
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.289
Carcinogencity:	0.849
Eye Corrosion:	0.004
Eye Irritation:	0.187
Respiratory Toxicity:	0.812

Download Data

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

Natural Product: NPC304163

Natural Product ID:	NPC304163
*Common Name:**	Plantarenaloside
IUPAC Name:	(1S,4aR,7R,7aR)-4a-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
Synonyms:
Standard InCHIKey:	QCCRICPXIMDIGF-FHZCTKOVSA-N
Standard InCHI:	InChI=1S/C16H24O9/c1-7-2-3-16(22)8(4-17)6-23-14(10(7)16)25-15-13(21)12(20)11(19)9(5-18)24-15/h4,6-7,9-15,18-22H,2-3,5H2,1H3/t7-,9-,10+,11-,12+,13-,14+,15+,16+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@]3([C@H]2[C@H](C)CC3)O)C=O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622814
PubChem CID:	155882
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
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	Entire plants	the surroundings of Uppsala, Sweden	1998-SEP	PMID[11421736]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	Whole Plant	the surroundings of Uppsala, Sweden	1998-SEP	PMID[11421736]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141864]
NPO16360	Gardenia carinata	Species	Rubiaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[23550966]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[24895551]
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33328	cresentia alata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26351040]
NPO793	Pestalotiopsis microspora	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27556865]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784154]
NPO16598	Helenium elegans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4436	Trillium erectum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2656	Phtheirospermum japonicum	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17761	Ophiorrhiza japonica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO120	Tecoma stans	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2656	Phtheirospermum japonicum	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16598	Helenium elegans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO120	Tecoma stans	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4436	Trillium erectum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17761	Ophiorrhiza japonica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO120	Tecoma stans	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16598	Helenium elegans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21689	Titanotrichum oldhamii	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4436	Trillium erectum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17761	Ophiorrhiza japonica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO120	Tecoma stans	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16360	Gardenia carinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO793	Pestalotiopsis microspora	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24674	Trichoderma album	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28518	Solanum wendlandii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28896	Astragalus centralpinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25748	Eugenia grandis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29280	Argopsis megalospora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15523	Euphorbia calycina	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28080	Pedicularis palustris	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16598	Helenium elegans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14042	Rollinia dolabripetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8687	Chaerophyllum temulum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11903	Alysicarpus bupleurifolius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27644	Machaerocereus eruca	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27798	Verticillium intertextum	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26510	Gentianopsis ciliata	Species	Gentianaceae	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
Others	6

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	36.3	%	PMID[516390]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	36.6	%	PMID[516390]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	39.9	%	PMID[516390]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<=	30.0	%	PMID[516390]

☑ 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 NPC304163 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	218
0.1-0.2	1528
0.2-0.3	5837
0.3-0.4	11510
0.4-0.5	11656
0.5-0.6	8307
0.6-0.7	3455
0.7-0.8	162
0.8-0.85	6
0.85-0.9	14
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9255	High Similarity	NPC63897
0.9082	High Similarity	NPC287539
0.9082	High Similarity	NPC3488
0.8922	High Similarity	NPC110701
0.8911	High Similarity	NPC127235
0.89	High Similarity	NPC37240
0.8878	High Similarity	NPC37866
0.88	High Similarity	NPC35185
0.88	High Similarity	NPC474730
0.88	High Similarity	NPC4899
0.88	High Similarity	NPC177013
0.8713	High Similarity	NPC475928
0.8673	High Similarity	NPC161293
0.8641	High Similarity	NPC148270
0.8641	High Similarity	NPC80338
0.8641	High Similarity	NPC197813
0.8544	High Similarity	NPC170432
0.8431	Intermediate Similarity	NPC106668
0.8396	Intermediate Similarity	NPC193741
0.835	Intermediate Similarity	NPC27687
0.8241	Intermediate Similarity	NPC475851
0.8241	Intermediate Similarity	NPC475924
0.8119	Intermediate Similarity	NPC170527
0.8081	Intermediate Similarity	NPC235051
0.802	Intermediate Similarity	NPC93869
0.802	Intermediate Similarity	NPC6765
0.7921	Intermediate Similarity	NPC274588
0.7879	Intermediate Similarity	NPC93190
0.783	Intermediate Similarity	NPC329704
0.781	Intermediate Similarity	NPC216911
0.7767	Intermediate Similarity	NPC284063
0.7767	Intermediate Similarity	NPC241911
0.7767	Intermediate Similarity	NPC474297
0.7736	Intermediate Similarity	NPC80144
0.7723	Intermediate Similarity	NPC274274
0.7723	Intermediate Similarity	NPC294643
0.7723	Intermediate Similarity	NPC473150
0.7714	Intermediate Similarity	NPC476211
0.7714	Intermediate Similarity	NPC476320
0.7714	Intermediate Similarity	NPC255677
0.7714	Intermediate Similarity	NPC22149
0.7714	Intermediate Similarity	NPC306344
0.77	Intermediate Similarity	NPC50464
0.7692	Intermediate Similarity	NPC86843
0.7692	Intermediate Similarity	NPC58267
0.7692	Intermediate Similarity	NPC261372
0.7692	Intermediate Similarity	NPC263674
0.767	Intermediate Similarity	NPC101051
0.7664	Intermediate Similarity	NPC329834
0.7642	Intermediate Similarity	NPC27474
0.7642	Intermediate Similarity	NPC298255
0.7642	Intermediate Similarity	NPC67296
0.7642	Intermediate Similarity	NPC28304
0.7642	Intermediate Similarity	NPC476230
0.7624	Intermediate Similarity	NPC120021
0.7624	Intermediate Similarity	NPC65665
0.7624	Intermediate Similarity	NPC231710
0.7624	Intermediate Similarity	NPC216826
0.7624	Intermediate Similarity	NPC470573
0.7624	Intermediate Similarity	NPC270908
0.7619	Intermediate Similarity	NPC49833
0.7619	Intermediate Similarity	NPC249171
0.7593	Intermediate Similarity	NPC86095
0.7576	Intermediate Similarity	NPC149018
0.7576	Intermediate Similarity	NPC171484
0.7576	Intermediate Similarity	NPC470657
0.7568	Intermediate Similarity	NPC106760
0.7565	Intermediate Similarity	NPC13710
0.7551	Intermediate Similarity	NPC98276
0.7551	Intermediate Similarity	NPC259296
0.7542	Intermediate Similarity	NPC1980
0.7542	Intermediate Similarity	NPC238005
0.7542	Intermediate Similarity	NPC141196
0.7524	Intermediate Similarity	NPC472290
0.7524	Intermediate Similarity	NPC304445
0.7524	Intermediate Similarity	NPC236580
0.7523	Intermediate Similarity	NPC41681
0.7521	Intermediate Similarity	NPC473228
0.7521	Intermediate Similarity	NPC470829
0.75	Intermediate Similarity	NPC284929
0.75	Intermediate Similarity	NPC31349
0.75	Intermediate Similarity	NPC473148
0.75	Intermediate Similarity	NPC118761
0.75	Intermediate Similarity	NPC197541
0.75	Intermediate Similarity	NPC234304
0.75	Intermediate Similarity	NPC267869
0.7477	Intermediate Similarity	NPC471401
0.7477	Intermediate Similarity	NPC476228
0.7458	Intermediate Similarity	NPC216866
0.7455	Intermediate Similarity	NPC254538
0.7455	Intermediate Similarity	NPC474285
0.7453	Intermediate Similarity	NPC472015
0.7451	Intermediate Similarity	NPC117596
0.7451	Intermediate Similarity	NPC246173
0.744	Intermediate Similarity	NPC289700
0.744	Intermediate Similarity	NPC62172
0.7417	Intermediate Similarity	NPC198714
0.7407	Intermediate Similarity	NPC261117
0.7407	Intermediate Similarity	NPC222062
0.7407	Intermediate Similarity	NPC13171
0.7407	Intermediate Similarity	NPC250545
0.7407	Intermediate Similarity	NPC195510
0.7407	Intermediate Similarity	NPC310804
0.7398	Intermediate Similarity	NPC155529
0.7387	Intermediate Similarity	NPC224414
0.7383	Intermediate Similarity	NPC473146
0.7379	Intermediate Similarity	NPC66504
0.7379	Intermediate Similarity	NPC472125
0.7379	Intermediate Similarity	NPC472124
0.7379	Intermediate Similarity	NPC472126
0.7373	Intermediate Similarity	NPC42675
0.7368	Intermediate Similarity	NPC102619
0.7355	Intermediate Similarity	NPC152091
0.7353	Intermediate Similarity	NPC22918
0.7345	Intermediate Similarity	NPC63244
0.7345	Intermediate Similarity	NPC122339
0.7323	Intermediate Similarity	NPC75616
0.7321	Intermediate Similarity	NPC8431
0.7308	Intermediate Similarity	NPC61201
0.7288	Intermediate Similarity	NPC281840
0.7282	Intermediate Similarity	NPC307699
0.7281	Intermediate Similarity	NPC471244
0.7281	Intermediate Similarity	NPC473303
0.7281	Intermediate Similarity	NPC243572
0.7281	Intermediate Similarity	NPC471245
0.7281	Intermediate Similarity	NPC157929
0.7281	Intermediate Similarity	NPC145625
0.7265	Intermediate Similarity	NPC469822
0.7265	Intermediate Similarity	NPC475309
0.7257	Intermediate Similarity	NPC471476
0.7257	Intermediate Similarity	NPC473324
0.7255	Intermediate Similarity	NPC148534
0.7248	Intermediate Similarity	NPC94919
0.7241	Intermediate Similarity	NPC277583
0.7241	Intermediate Similarity	NPC88945
0.7236	Intermediate Similarity	NPC180079
0.7236	Intermediate Similarity	NPC471361
0.7236	Intermediate Similarity	NPC6108
0.7236	Intermediate Similarity	NPC469752
0.7236	Intermediate Similarity	NPC86159
0.7236	Intermediate Similarity	NPC471352
0.7236	Intermediate Similarity	NPC17896
0.7236	Intermediate Similarity	NPC89514
0.7236	Intermediate Similarity	NPC469754
0.7236	Intermediate Similarity	NPC469751
0.7236	Intermediate Similarity	NPC469753
0.7236	Intermediate Similarity	NPC197707
0.7236	Intermediate Similarity	NPC284406
0.7236	Intermediate Similarity	NPC471359
0.7236	Intermediate Similarity	NPC9499
0.7236	Intermediate Similarity	NPC251866
0.7236	Intermediate Similarity	NPC10823
0.7236	Intermediate Similarity	NPC70542
0.7236	Intermediate Similarity	NPC471358
0.7236	Intermediate Similarity	NPC471360
0.7236	Intermediate Similarity	NPC219085
0.7236	Intermediate Similarity	NPC469755
0.7222	Intermediate Similarity	NPC158350
0.7217	Intermediate Similarity	NPC132668
0.7217	Intermediate Similarity	NPC477944
0.7217	Intermediate Similarity	NPC73986
0.7217	Intermediate Similarity	NPC94141
0.7212	Intermediate Similarity	NPC472199
0.7207	Intermediate Similarity	NPC285927
0.72	Intermediate Similarity	NPC3464
0.72	Intermediate Similarity	NPC475963
0.72	Intermediate Similarity	NPC151176
0.7196	Intermediate Similarity	NPC470683
0.7196	Intermediate Similarity	NPC474313
0.7196	Intermediate Similarity	NPC470684
0.7193	Intermediate Similarity	NPC272242
0.7193	Intermediate Similarity	NPC274833
0.719	Intermediate Similarity	NPC277191
0.719	Intermediate Similarity	NPC190846
0.7179	Intermediate Similarity	NPC473304
0.717	Intermediate Similarity	NPC167893
0.7168	Intermediate Similarity	NPC471400
0.7168	Intermediate Similarity	NPC208307
0.7167	Intermediate Similarity	NPC28532
0.7165	Intermediate Similarity	NPC127656
0.7157	Intermediate Similarity	NPC258501
0.7156	Intermediate Similarity	NPC20673
0.7156	Intermediate Similarity	NPC98859
0.7156	Intermediate Similarity	NPC4637
0.7155	Intermediate Similarity	NPC17165
0.7155	Intermediate Similarity	NPC74727
0.7143	Intermediate Similarity	NPC471461
0.7143	Intermediate Similarity	NPC475788
0.7143	Intermediate Similarity	NPC67745
0.7131	Intermediate Similarity	NPC250556
0.7131	Intermediate Similarity	NPC469750
0.7131	Intermediate Similarity	NPC93368
0.713	Intermediate Similarity	NPC207845
0.713	Intermediate Similarity	NPC472719
0.7119	Intermediate Similarity	NPC475632
0.7119	Intermediate Similarity	NPC471249
0.7119	Intermediate Similarity	NPC86020
0.7115	Intermediate Similarity	NPC6414
0.7115	Intermediate Similarity	NPC303451
0.7105	Intermediate Similarity	NPC27551

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 NPC304163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	2236
0.2-0.3	4049
0.3-0.4	1760
0.4-0.5	508
0.5-0.6	300
0.6-0.7	88
0.7-0.8	0
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
0.7236	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7131	Intermediate Similarity	NPD7507	Approved
0.693	Remote Similarity	NPD6686	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6885	Remote Similarity	NPD6370	Approved
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD7503	Approved
0.6721	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6614	Remote Similarity	NPD7736	Approved
0.6613	Remote Similarity	NPD5988	Approved
0.6585	Remote Similarity	NPD6319	Approved
0.6585	Remote Similarity	NPD6059	Approved
0.6574	Remote Similarity	NPD7983	Approved
0.6555	Remote Similarity	NPD6053	Discontinued
0.6552	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8293	Discontinued
0.6525	Remote Similarity	NPD6371	Approved
0.6508	Remote Similarity	NPD7492	Approved
0.6481	Remote Similarity	NPD46	Approved
0.6481	Remote Similarity	NPD6698	Approved
0.6475	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6616	Approved
0.6423	Remote Similarity	NPD7327	Approved
0.6423	Remote Similarity	NPD7328	Approved
0.6415	Remote Similarity	NPD4249	Approved
0.6406	Remote Similarity	NPD7078	Approved
0.6379	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD8299	Approved
0.6378	Remote Similarity	NPD8341	Approved
0.6378	Remote Similarity	NPD8342	Approved
0.6378	Remote Similarity	NPD8340	Approved
0.6372	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7516	Approved
0.6355	Remote Similarity	NPD4251	Approved
0.6355	Remote Similarity	NPD4250	Approved
0.6349	Remote Similarity	NPD8080	Discontinued
0.6341	Remote Similarity	NPD6009	Approved
0.632	Remote Similarity	NPD8377	Approved
0.632	Remote Similarity	NPD8294	Approved
0.6306	Remote Similarity	NPD5282	Discontinued
0.6299	Remote Similarity	NPD7642	Approved
0.629	Remote Similarity	NPD7641	Discontinued
0.6281	Remote Similarity	NPD6882	Approved
0.627	Remote Similarity	NPD8033	Approved
0.627	Remote Similarity	NPD8296	Approved
0.627	Remote Similarity	NPD8380	Approved
0.627	Remote Similarity	NPD8335	Approved
0.627	Remote Similarity	NPD8378	Approved
0.627	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.627	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD4634	Approved
0.623	Remote Similarity	NPD4632	Approved
0.6202	Remote Similarity	NPD8451	Approved
0.6195	Remote Similarity	NPD7839	Suspended
0.619	Remote Similarity	NPD6435	Approved
0.6172	Remote Similarity	NPD8328	Phase 3
0.6172	Remote Similarity	NPD7830	Approved
0.6172	Remote Similarity	NPD7829	Approved
0.6168	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD8448	Approved
0.6154	Remote Similarity	NPD8074	Phase 3
0.6148	Remote Similarity	NPD8297	Approved
0.6136	Remote Similarity	NPD5956	Approved
0.6132	Remote Similarity	NPD7154	Phase 3
0.6132	Remote Similarity	NPD4788	Approved
0.6132	Remote Similarity	NPD5362	Discontinued
0.6111	Remote Similarity	NPD5786	Approved
0.6107	Remote Similarity	NPD8337	Approved
0.6107	Remote Similarity	NPD6033	Approved
0.6107	Remote Similarity	NPD8336	Approved
0.6095	Remote Similarity	NPD5369	Approved
0.608	Remote Similarity	NPD7115	Discovery
0.608	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5779	Approved
0.6071	Remote Similarity	NPD5778	Approved
0.6068	Remote Similarity	NPD5211	Phase 2
0.6038	Remote Similarity	NPD4270	Approved
0.6038	Remote Similarity	NPD4269	Approved
0.6036	Remote Similarity	NPD5785	Approved
0.6033	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD8392	Approved
0.6015	Remote Similarity	NPD8391	Approved
0.6015	Remote Similarity	NPD8390	Approved
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4819	Approved
0.6	Remote Similarity	NPD4820	Approved
0.6	Remote Similarity	NPD5697	Approved
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7637	Suspended
0.5966	Remote Similarity	NPD5141	Approved
0.5962	Remote Similarity	NPD4802	Phase 2
0.5962	Remote Similarity	NPD4238	Approved
0.595	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6881	Approved
0.595	Remote Similarity	NPD6899	Approved
0.5941	Remote Similarity	NPD3181	Approved
0.5935	Remote Similarity	NPD6649	Approved
0.5935	Remote Similarity	NPD6650	Approved
0.5932	Remote Similarity	NPD8083	Approved
0.5932	Remote Similarity	NPD8139	Approved
0.5932	Remote Similarity	NPD8085	Approved
0.5932	Remote Similarity	NPD8084	Approved
0.5932	Remote Similarity	NPD8138	Approved
0.5932	Remote Similarity	NPD8086	Approved
0.5932	Remote Similarity	NPD8082	Approved
0.5926	Remote Similarity	NPD8338	Approved
0.5923	Remote Similarity	NPD6067	Discontinued
0.5917	Remote Similarity	NPD6402	Approved
0.5917	Remote Similarity	NPD6675	Approved
0.5917	Remote Similarity	NPD5739	Approved
0.5917	Remote Similarity	NPD7128	Approved
0.5909	Remote Similarity	NPD7524	Approved
0.5902	Remote Similarity	NPD6372	Approved
0.5902	Remote Similarity	NPD6012	Approved
0.5902	Remote Similarity	NPD6013	Approved
0.5902	Remote Similarity	NPD6014	Approved
0.5902	Remote Similarity	NPD6373	Approved
0.5897	Remote Similarity	NPD4696	Approved
0.5897	Remote Similarity	NPD5285	Approved
0.5897	Remote Similarity	NPD5286	Approved
0.5891	Remote Similarity	NPD8444	Approved
0.5891	Remote Similarity	NPD8266	Approved
0.5891	Remote Similarity	NPD5983	Phase 2
0.5891	Remote Similarity	NPD8267	Approved
0.5891	Remote Similarity	NPD8268	Approved
0.5891	Remote Similarity	NPD8269	Approved
0.5882	Remote Similarity	NPD8275	Approved
0.5882	Remote Similarity	NPD8276	Approved
0.587	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD5701	Approved
0.5862	Remote Similarity	NPD4755	Approved
0.5862	Remote Similarity	NPD6084	Phase 2
0.5862	Remote Similarity	NPD6083	Phase 2
0.5854	Remote Similarity	NPD6883	Approved
0.5854	Remote Similarity	NPD7102	Approved
0.5854	Remote Similarity	NPD7290	Approved
0.5849	Remote Similarity	NPD4252	Approved
0.5833	Remote Similarity	NPD6110	Phase 1
0.5833	Remote Similarity	NPD8081	Approved
0.5826	Remote Similarity	NPD5695	Phase 3
0.582	Remote Similarity	NPD6011	Approved
0.582	Remote Similarity	NPD7320	Approved
0.5812	Remote Similarity	NPD4225	Approved
0.581	Remote Similarity	NPD4271	Approved
0.581	Remote Similarity	NPD4268	Approved
0.5806	Remote Similarity	NPD6617	Approved
0.5806	Remote Similarity	NPD6847	Approved
0.5806	Remote Similarity	NPD6869	Approved
0.5806	Remote Similarity	NPD8130	Phase 1
0.5804	Remote Similarity	NPD4753	Phase 2
0.5804	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6101	Approved
0.5804	Remote Similarity	NPD1695	Approved
0.5802	Remote Similarity	NPD7604	Phase 2
0.5798	Remote Similarity	NPD5224	Approved
0.5798	Remote Similarity	NPD5225	Approved
0.5798	Remote Similarity	NPD5226	Approved
0.5798	Remote Similarity	NPD4633	Approved
0.5789	Remote Similarity	NPD8171	Discontinued
0.5785	Remote Similarity	NPD8393	Approved
0.578	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD4700	Approved
0.5763	Remote Similarity	NPD7640	Approved
0.5763	Remote Similarity	NPD7639	Approved
0.5752	Remote Similarity	NPD7838	Discovery
0.575	Remote Similarity	NPD5175	Approved
0.575	Remote Similarity	NPD5174	Approved
0.5738	Remote Similarity	NPD8140	Approved
0.5738	Remote Similarity	NPD8307	Discontinued
0.5736	Remote Similarity	NPD4522	Approved
0.5727	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5223	Approved
0.5714	Remote Similarity	NPD6336	Discontinued
0.5702	Remote Similarity	NPD6411	Approved
0.5691	Remote Similarity	NPD4729	Approved
0.5691	Remote Similarity	NPD4730	Approved
0.569	Remote Similarity	NPD4629	Approved
0.569	Remote Similarity	NPD5210	Approved
0.569	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD5332	Approved
0.5688	Remote Similarity	NPD5331	Approved
0.5688	Remote Similarity	NPD6695	Phase 3
0.5678	Remote Similarity	NPD7638	Approved
0.5678	Remote Similarity	NPD5696	Approved
0.566	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6008	Approved
0.5656	Remote Similarity	NPD4767	Approved
0.5656	Remote Similarity	NPD4768	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