NPASS Compound

Structure

CID254538 OpenBabel06191716052D 33 36 0 0 1 0 0 0 0 0999 V2000 1.0409 -3.1650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3847 4.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 0.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7866 2.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2319 -2.5772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6526 1.3736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6526 2.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5435 1.3736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7866 0.8736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5435 2.3736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6775 2.8736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8115 2.3736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5187 2.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0794 1.3736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8115 1.3736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2756 1.3736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6817 -2.9839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 2.8736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6775 3.8736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9454 2.8736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3847 2.3736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5187 3.8736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0794 2.3736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6775 0.8736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9454 0.8736 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 2 29 1 0 0 0 0 3 4 2 0 0 0 0 5 10 2 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 11 2 0 0 0 0 7 30 1 0 0 0 0 8 1 1 6 0 0 0 8 10 1 0 0 0 0 8 23 1 0 0 0 0 9 3 1 1 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 12 6 1 6 0 0 0 12 14 1 0 0 0 0 12 31 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 1 0 0 0 14 15 1 0 0 0 0 14 24 1 1 0 0 0 15 16 1 0 0 0 0 15 25 1 6 0 0 0 16 20 1 0 0 0 0 16 26 1 1 0 0 0 17 27 2 0 0 0 0 17 29 1 0 0 0 0 18 28 2 0 0 0 0 18 33 1 0 0 0 0 19 30 1 0 0 0 0 19 32 1 6 0 0 0 20 31 1 0 0 0 0 20 32 1 6 0 0 0 21 4 1 6 0 0 0 21 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.14
Volume:	429.847
LogP:	-0.25
LogD:	-0.346
LogS:	-1.398
# Rotatable Bonds:	6
TPSA:	181.44
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.213
Synthetic Accessibility Score:	5.693
Fsp3:	0.619
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:	-5.841
MDCK Permeability:	0.00010120451770490035
Pgp-inhibitor:	0.002
Pgp-substrate:	0.108
Human Intestinal Absorption (HIA):	0.926
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	20.08340835571289%
Volume Distribution (VD):	0.473
Pgp-substrate:	50.52830505371094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	1.714
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.367
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.569
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.199
Carcinogencity:	0.949
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC254538

Natural Product ID:	NPC254538
*Common Name:**	Plumieride
IUPAC Name:	methyl (1S,4aS,7R,7aS)-4'-[(1S)-1-hydroxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
Synonyms:	Plumieride
Standard InCHIKey:	AOPMSFXOYJXDNJ-IRFSQMTFSA-N
Standard InCHI:	InChI=1S/C21H26O12/c1-8(23)10-5-21(33-18(10)28)4-3-9-11(17(27)29-2)7-30-19(13(9)21)32-20-16(26)15(25)14(24)12(6-22)31-20/h3-5,7-9,12-16,19-20,22-26H,6H2,1-2H3/t8-,9+,12+,13+,14+,15-,16+,19-,20-,21+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@]2(C=C3)OC(=O)C(=C2)[C@@H](O)C)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464470
PubChem CID:	72319
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
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	bark	Indonesia	n.a.	PMID[1965200]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16377	Juniperus ashei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18768	Haliclona tubifera	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6746	Blighia welwitschii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17373.1	Cunninghamia lanceolata var. konishii	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3446	Acanthaster planci	Species	Acanthasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17707	Dioscorea villosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18031	Russula vesca	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16254	Backhousia angustifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15966	Sassafras officinalis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3990	Acacia salicina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10438	Tanacetum nubigenum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2591	Io fluvialis	Species	Pleuroceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9524	Kalanchoe blossfeldiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	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
ED50	7
IC50	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[498582]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[498582]
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	ug ml-1	PMID[498582]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[498583]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	50.0	ug ml-1	PMID[498582]

☑ 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 NPC254538 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	215
0.1-0.2	1360
0.2-0.3	4776
0.3-0.4	8268
0.4-0.5	14662
0.5-0.6	8897
0.6-0.7	4066
0.7-0.8	403
0.8-0.85	25
0.85-0.9	21
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474285
0.9394	High Similarity	NPC13171
0.9394	High Similarity	NPC195510
0.8878	High Similarity	NPC475832
0.8878	High Similarity	NPC475927
0.8835	High Similarity	NPC86095
0.8812	High Similarity	NPC22149
0.8812	High Similarity	NPC255677
0.8812	High Similarity	NPC306344
0.8725	High Similarity	NPC298255
0.8725	High Similarity	NPC28304
0.8641	High Similarity	NPC261117
0.8641	High Similarity	NPC310804
0.8641	High Similarity	NPC250545
0.8586	High Similarity	NPC61201
0.8558	High Similarity	NPC197541
0.8558	High Similarity	NPC234304
0.8558	High Similarity	NPC118761
0.8558	High Similarity	NPC267869
0.8558	High Similarity	NPC284929
0.8515	High Similarity	NPC241911
0.8462	Intermediate Similarity	NPC222062
0.8416	Intermediate Similarity	NPC101051
0.8384	Intermediate Similarity	NPC303451
0.8384	Intermediate Similarity	NPC6414
0.8265	Intermediate Similarity	NPC475037
0.8241	Intermediate Similarity	NPC475960
0.82	Intermediate Similarity	NPC120021
0.82	Intermediate Similarity	NPC470573
0.82	Intermediate Similarity	NPC270908
0.82	Intermediate Similarity	NPC231710
0.82	Intermediate Similarity	NPC65665
0.82	Intermediate Similarity	NPC216826
0.82	Intermediate Similarity	NPC117596
0.8119	Intermediate Similarity	NPC472124
0.8119	Intermediate Similarity	NPC472125
0.8119	Intermediate Similarity	NPC472126
0.807	Intermediate Similarity	NPC475309
0.8061	Intermediate Similarity	NPC475034
0.8058	Intermediate Similarity	NPC469543
0.8058	Intermediate Similarity	NPC170204
0.802	Intermediate Similarity	NPC307699
0.7963	Intermediate Similarity	NPC474917
0.7963	Intermediate Similarity	NPC307846
0.7963	Intermediate Similarity	NPC305157
0.7959	Intermediate Similarity	NPC475035
0.7944	Intermediate Similarity	NPC471599
0.7913	Intermediate Similarity	NPC13710
0.7905	Intermediate Similarity	NPC40812
0.7879	Intermediate Similarity	NPC470124
0.787	Intermediate Similarity	NPC37240
0.7863	Intermediate Similarity	NPC473228
0.7863	Intermediate Similarity	NPC470829
0.785	Intermediate Similarity	NPC219038
0.785	Intermediate Similarity	NPC98859
0.785	Intermediate Similarity	NPC20673
0.785	Intermediate Similarity	NPC4637
0.783	Intermediate Similarity	NPC308567
0.783	Intermediate Similarity	NPC187761
0.783	Intermediate Similarity	NPC83895
0.783	Intermediate Similarity	NPC261377
0.783	Intermediate Similarity	NPC255592
0.7778	Intermediate Similarity	NPC266718
0.7778	Intermediate Similarity	NPC177013
0.7778	Intermediate Similarity	NPC4899
0.7778	Intermediate Similarity	NPC35185
0.7778	Intermediate Similarity	NPC474730
0.7767	Intermediate Similarity	NPC9447
0.7767	Intermediate Similarity	NPC477749
0.7757	Intermediate Similarity	NPC244878
0.7748	Intermediate Similarity	NPC110701
0.7748	Intermediate Similarity	NPC219900
0.7748	Intermediate Similarity	NPC177524
0.7748	Intermediate Similarity	NPC392
0.7736	Intermediate Similarity	NPC472290
0.7727	Intermediate Similarity	NPC239961
0.7692	Intermediate Similarity	NPC320552
0.7685	Intermediate Similarity	NPC3488
0.7685	Intermediate Similarity	NPC198992
0.7685	Intermediate Similarity	NPC287539
0.7679	Intermediate Similarity	NPC313668
0.7679	Intermediate Similarity	NPC315836
0.767	Intermediate Similarity	NPC327253
0.7664	Intermediate Similarity	NPC472015
0.7664	Intermediate Similarity	NPC307517
0.7664	Intermediate Similarity	NPC61630
0.7664	Intermediate Similarity	NPC81483
0.7664	Intermediate Similarity	NPC169468
0.7664	Intermediate Similarity	NPC151093
0.7658	Intermediate Similarity	NPC148270
0.7658	Intermediate Similarity	NPC80338
0.7658	Intermediate Similarity	NPC197813
0.7647	Intermediate Similarity	NPC137368
0.7642	Intermediate Similarity	NPC161293
0.7642	Intermediate Similarity	NPC306041
0.7619	Intermediate Similarity	NPC25701
0.7619	Intermediate Similarity	NPC2003
0.7615	Intermediate Similarity	NPC313569
0.7615	Intermediate Similarity	NPC106668
0.7589	Intermediate Similarity	NPC473807
0.7573	Intermediate Similarity	NPC477748
0.757	Intermediate Similarity	NPC476612
0.757	Intermediate Similarity	NPC476613
0.757	Intermediate Similarity	NPC471462
0.7568	Intermediate Similarity	NPC170432
0.7568	Intermediate Similarity	NPC127235
0.7549	Intermediate Similarity	NPC142583
0.7547	Intermediate Similarity	NPC471142
0.7545	Intermediate Similarity	NPC475928
0.7545	Intermediate Similarity	NPC27687
0.7545	Intermediate Similarity	NPC110989
0.7524	Intermediate Similarity	NPC238090
0.7524	Intermediate Similarity	NPC280390
0.7524	Intermediate Similarity	NPC472195
0.7524	Intermediate Similarity	NPC472196
0.7523	Intermediate Similarity	NPC476611
0.7521	Intermediate Similarity	NPC474483
0.75	Intermediate Similarity	NPC198422
0.75	Intermediate Similarity	NPC202886
0.75	Intermediate Similarity	NPC473307
0.75	Intermediate Similarity	NPC40182
0.75	Intermediate Similarity	NPC471144
0.75	Intermediate Similarity	NPC118078
0.75	Intermediate Similarity	NPC473448
0.7479	Intermediate Similarity	NPC48692
0.7478	Intermediate Similarity	NPC66108
0.7477	Intermediate Similarity	NPC203659
0.7477	Intermediate Similarity	NPC54731
0.7477	Intermediate Similarity	NPC100487
0.7456	Intermediate Similarity	NPC46407
0.7456	Intermediate Similarity	NPC193741
0.7456	Intermediate Similarity	NPC235014
0.7455	Intermediate Similarity	NPC304163
0.7455	Intermediate Similarity	NPC225353
0.7453	Intermediate Similarity	NPC472198
0.7453	Intermediate Similarity	NPC256368
0.7453	Intermediate Similarity	NPC159698
0.7453	Intermediate Similarity	NPC294293
0.7453	Intermediate Similarity	NPC71589
0.7436	Intermediate Similarity	NPC471816
0.7436	Intermediate Similarity	NPC277583
0.7429	Intermediate Similarity	NPC472199
0.7426	Intermediate Similarity	NPC220167
0.7426	Intermediate Similarity	NPC136699
0.7417	Intermediate Similarity	NPC170084
0.7417	Intermediate Similarity	NPC170880
0.7417	Intermediate Similarity	NPC476204
0.7414	Intermediate Similarity	NPC264153
0.7411	Intermediate Similarity	NPC82251
0.7411	Intermediate Similarity	NPC472751
0.7411	Intermediate Similarity	NPC41681
0.7411	Intermediate Similarity	NPC469852
0.7411	Intermediate Similarity	NPC472749
0.7411	Intermediate Similarity	NPC476738
0.7411	Intermediate Similarity	NPC476740
0.7407	Intermediate Similarity	NPC474194
0.7407	Intermediate Similarity	NPC153559
0.7407	Intermediate Similarity	NPC2666
0.7407	Intermediate Similarity	NPC471490
0.7398	Intermediate Similarity	NPC117702
0.7398	Intermediate Similarity	NPC469757
0.7398	Intermediate Similarity	NPC471357
0.7398	Intermediate Similarity	NPC146456
0.7387	Intermediate Similarity	NPC475871
0.7387	Intermediate Similarity	NPC309398
0.7387	Intermediate Similarity	NPC475945
0.7383	Intermediate Similarity	NPC36954
0.7379	Intermediate Similarity	NPC475186
0.7379	Intermediate Similarity	NPC118077
0.7377	Intermediate Similarity	NPC318135
0.7368	Intermediate Similarity	NPC38154
0.7358	Intermediate Similarity	NPC475912
0.7358	Intermediate Similarity	NPC471483
0.7358	Intermediate Similarity	NPC320089
0.7344	Intermediate Similarity	NPC62172
0.7344	Intermediate Similarity	NPC289700
0.7339	Intermediate Similarity	NPC90819
0.7339	Intermediate Similarity	NPC187268
0.7339	Intermediate Similarity	NPC245094
0.7339	Intermediate Similarity	NPC311534
0.7339	Intermediate Similarity	NPC124181
0.7333	Intermediate Similarity	NPC476127
0.7333	Intermediate Similarity	NPC473311
0.7333	Intermediate Similarity	NPC476150
0.7328	Intermediate Similarity	NPC475851
0.7328	Intermediate Similarity	NPC475924
0.7327	Intermediate Similarity	NPC211455
0.7327	Intermediate Similarity	NPC44261
0.7327	Intermediate Similarity	NPC188717
0.7323	Intermediate Similarity	NPC471234
0.7321	Intermediate Similarity	NPC469869
0.7321	Intermediate Similarity	NPC472748
0.7315	Intermediate Similarity	NPC256230
0.7315	Intermediate Similarity	NPC473333
0.7315	Intermediate Similarity	NPC477921
0.7304	Intermediate Similarity	NPC476766
0.7304	Intermediate Similarity	NPC472508
0.7302	Intermediate Similarity	NPC155529
0.7297	Intermediate Similarity	NPC201191
0.7297	Intermediate Similarity	NPC149371

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 NPC254538 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1718
0.2-0.3	3941
0.3-0.4	2182
0.4-0.5	803
0.5-0.6	240
0.6-0.7	79
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
0.7748	Intermediate Similarity	NPD6686	Approved
0.7417	Intermediate Similarity	NPD8513	Phase 3
0.728	Intermediate Similarity	NPD7319	Approved
0.7273	Intermediate Similarity	NPD8516	Approved
0.7273	Intermediate Similarity	NPD8515	Approved
0.7273	Intermediate Similarity	NPD8517	Approved
0.7182	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7507	Approved
0.7094	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD46	Approved
0.7009	Intermediate Similarity	NPD6698	Approved
0.6992	Remote Similarity	NPD7503	Approved
0.6944	Remote Similarity	NPD7983	Approved
0.688	Remote Similarity	NPD7830	Approved
0.688	Remote Similarity	NPD7829	Approved
0.6864	Remote Similarity	NPD6371	Approved
0.6757	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6053	Discontinued
0.6748	Remote Similarity	NPD7328	Approved
0.6748	Remote Similarity	NPD7327	Approved
0.6746	Remote Similarity	NPD7642	Approved
0.6719	Remote Similarity	NPD8074	Phase 3
0.6697	Remote Similarity	NPD7838	Discovery
0.6694	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD8080	Discontinued
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8451	Approved
0.664	Remote Similarity	NPD8294	Approved
0.664	Remote Similarity	NPD8377	Approved
0.6589	Remote Similarity	NPD8448	Approved
0.6587	Remote Similarity	NPD8033	Approved
0.6587	Remote Similarity	NPD8296	Approved
0.6587	Remote Similarity	NPD8335	Approved
0.6587	Remote Similarity	NPD8380	Approved
0.6587	Remote Similarity	NPD8379	Approved
0.6587	Remote Similarity	NPD8378	Approved
0.6579	Remote Similarity	NPD4225	Approved
0.6577	Remote Similarity	NPD5778	Approved
0.6577	Remote Similarity	NPD5779	Approved
0.6562	Remote Similarity	NPD8299	Approved
0.6562	Remote Similarity	NPD8342	Approved
0.6562	Remote Similarity	NPD8340	Approved
0.6562	Remote Similarity	NPD8341	Approved
0.6549	Remote Similarity	NPD7839	Suspended
0.6538	Remote Similarity	NPD7736	Approved
0.6535	Remote Similarity	NPD6370	Approved
0.6509	Remote Similarity	NPD6110	Phase 1
0.6484	Remote Similarity	NPD8328	Phase 3
0.6481	Remote Similarity	NPD4249	Approved
0.6471	Remote Similarity	NPD6412	Phase 2
0.6466	Remote Similarity	NPD5344	Discontinued
0.6457	Remote Similarity	NPD8444	Approved
0.6457	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8392	Approved
0.6439	Remote Similarity	NPD8391	Approved
0.6439	Remote Similarity	NPD8390	Approved
0.6434	Remote Similarity	NPD7492	Approved
0.6422	Remote Similarity	NPD4250	Approved
0.6422	Remote Similarity	NPD4251	Approved
0.64	Remote Similarity	NPD7115	Discovery
0.6385	Remote Similarity	NPD6616	Approved
0.6378	Remote Similarity	NPD6054	Approved
0.6378	Remote Similarity	NPD6319	Approved
0.6349	Remote Similarity	NPD7641	Discontinued
0.6336	Remote Similarity	NPD8293	Discontinued
0.6336	Remote Similarity	NPD7078	Approved
0.6328	Remote Similarity	NPD6016	Approved
0.6328	Remote Similarity	NPD6015	Approved
0.629	Remote Similarity	NPD8133	Approved
0.6279	Remote Similarity	NPD5988	Approved
0.623	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7154	Phase 3
0.6161	Remote Similarity	NPD6101	Approved
0.6161	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6009	Approved
0.6142	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6059	Approved
0.6111	Remote Similarity	NPD5209	Approved
0.6106	Remote Similarity	NPD5785	Approved
0.6102	Remote Similarity	NPD6648	Approved
0.6102	Remote Similarity	NPD7640	Approved
0.6102	Remote Similarity	NPD7639	Approved
0.6091	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6882	Approved
0.6053	Remote Similarity	NPD6411	Approved
0.6053	Remote Similarity	NPD7637	Suspended
0.6048	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD8336	Approved
0.6045	Remote Similarity	NPD8337	Approved
0.6032	Remote Similarity	NPD4632	Approved
0.6018	Remote Similarity	NPD1695	Approved
0.6017	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD2204	Approved
0.5985	Remote Similarity	NPD8338	Approved
0.5968	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD8297	Approved
0.5946	Remote Similarity	NPD5363	Approved
0.5926	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD7260	Phase 2
0.5909	Remote Similarity	NPD5362	Discontinued
0.5896	Remote Similarity	NPD8273	Phase 1
0.5893	Remote Similarity	NPD5786	Approved
0.5857	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD896	Approved
0.5842	Remote Similarity	NPD898	Approved
0.5842	Remote Similarity	NPD897	Approved
0.5839	Remote Similarity	NPD6914	Discontinued
0.582	Remote Similarity	NPD1407	Approved
0.5818	Remote Similarity	NPD6435	Approved
0.5806	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD4634	Approved
0.5786	Remote Similarity	NPD8415	Approved
0.578	Remote Similarity	NPD4821	Approved
0.578	Remote Similarity	NPD4819	Approved
0.578	Remote Similarity	NPD4822	Approved
0.578	Remote Similarity	NPD4820	Approved
0.578	Remote Similarity	NPD4252	Approved
0.5769	Remote Similarity	NPD7500	Approved
0.576	Remote Similarity	NPD6899	Approved
0.576	Remote Similarity	NPD6881	Approved
0.5748	Remote Similarity	NPD6650	Approved
0.5748	Remote Similarity	NPD6649	Approved
0.5741	Remote Similarity	NPD4268	Approved
0.5741	Remote Similarity	NPD4271	Approved
0.5733	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD5956	Approved
0.5714	Remote Similarity	NPD6921	Approved
0.5714	Remote Similarity	NPD8269	Approved
0.5714	Remote Similarity	NPD8267	Approved
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD5983	Phase 2
0.5714	Remote Similarity	NPD8268	Approved
0.5714	Remote Similarity	NPD8266	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5693	Remote Similarity	NPD6033	Approved
0.5688	Remote Similarity	NPD7329	Approved
0.5686	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD4270	Approved
0.5676	Remote Similarity	NPD4269	Approved
0.5669	Remote Similarity	NPD7102	Approved
0.5669	Remote Similarity	NPD7290	Approved
0.5669	Remote Similarity	NPD6883	Approved
0.5664	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD1694	Approved
0.5649	Remote Similarity	NPD7505	Discontinued
0.5643	Remote Similarity	NPD6845	Suspended
0.5636	Remote Similarity	NPD5368	Approved
0.5635	Remote Similarity	NPD6011	Approved
0.5635	Remote Similarity	NPD7320	Approved
0.563	Remote Similarity	NPD7604	Phase 2
0.5625	Remote Similarity	NPD6869	Approved
0.5625	Remote Similarity	NPD8130	Phase 1
0.5625	Remote Similarity	NPD6617	Approved
0.5625	Remote Similarity	NPD6847	Approved
0.561	Remote Similarity	NPD8084	Approved
0.561	Remote Similarity	NPD5211	Phase 2
0.561	Remote Similarity	NPD8139	Approved
0.561	Remote Similarity	NPD8082	Approved
0.561	Remote Similarity	NPD8138	Approved
0.561	Remote Similarity	NPD7632	Discontinued
0.561	Remote Similarity	NPD8083	Approved
0.561	Remote Similarity	NPD8085	Approved
0.561	Remote Similarity	NPD8086	Approved
0.5602	Remote Similarity	NPD7685	Pre-registration
0.56	Remote Similarity	NPD5048	Discontinued
0.56	Remote Similarity	NPD7128	Approved
0.56	Remote Similarity	NPD6402	Approved
0.56	Remote Similarity	NPD5739	Approved
0.56	Remote Similarity	NPD6675	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