NPASS Compound

Structure

NPC473307 OpenBabel07101719252D 31 33 0 0 1 0 0 0 0 0999 V2000 2.6210 -5.9257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6002 3.8373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7592 2.5501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6647 -5.5099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7772 -5.3261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3119 -4.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0650 2.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0248 -3.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3614 -3.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8966 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8081 2.8592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3338 -4.7667 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.8262 -5.0171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1535 -2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2729 1.2119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6939 -3.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -1.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7377 -0.4354 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 -1.0830 -5.6862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2240 0.9029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 -3.2804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6183 -4.0390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6887 -0.7444 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 1.3849 -2.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5298 0.5427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 13 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 19 1 0 0 0 0 8 14 1 0 0 0 0 8 20 1 0 0 0 0 9 17 2 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 27 1 0 0 0 0 11 16 2 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 15 24 2 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 1 0 0 0 18 30 1 0 0 0 0 19 25 2 0 0 0 0 19 31 1 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 6 0 0 0 22 28 1 0 0 0 0 22 31 1 1 0 0 0 23 12 1 1 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.19
Volume:	435.198
LogP:	3.294
LogD:	2.221
LogS:	-3.924
# Rotatable Bonds:	11
TPSA:	100.66
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.249
Synthetic Accessibility Score:	5.345
Fsp3:	0.609
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.662
MDCK Permeability:	3.354034561198205e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.879
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	56.10991287231445%
Volume Distribution (VD):	1.946
Pgp-substrate:	28.540557861328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.412
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.738
CYP2C19-substrate:	0.216
CYP2C9-inhibitor:	0.81
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.64
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.786
CYP3A4-substrate:	0.357

ADMET: Excretion

Clearance (CL):	6.994
Half-life (T1/2):	0.744

ADMET: Toxicity

hERG Blockers:	0.202
Human Hepatotoxicity (H-HT):	0.914
Drug-inuced Liver Injury (DILI):	0.49
AMES Toxicity:	0.992
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.949
Carcinogencity:	0.92
Eye Corrosion:	0.045
Eye Irritation:	0.073
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC473307

Natural Product ID:	NPC473307
*Common Name:**	[(1S,6S,7R,7As)-4-(Acetyloxymethyl)-1-(3-Methylbut-2-Enoyloxy)Spiro[6,7A-Dihydro-1H-Cyclopenta[C]Pyran-7,2'-Oxirane]-6-Yl] 3-Methylpentanoate
IUPAC Name:	[(1S,6S,7R,7aS)-4-(acetyloxymethyl)-1-(3-methylbut-2-enoyloxy)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-6-yl] 3-methylpentanoate
Synonyms:
Standard InCHIKey:	KLQIXIQHWLZXBE-LKHWMGRZSA-N
Standard InCHI:	InChI=1S/C23H30O8/c1-6-14(4)8-20(26)30-18-9-17-16(10-27-15(5)24)11-28-22(21(17)23(18)12-29-23)31-19(25)7-13(2)3/h7,9,11,14,18,21-22H,6,8,10,12H2,1-5H3/t14?,18-,21+,22-,23+/m0/s1
SMILES:	CCC(CC(=O)O[C@H]1C=C2[C@@H]([C@]31CO3)[C@@H](OC=C2COC(=O)C)OC(=O)C=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399282
PubChem CID:	24763410
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO33249	valeriana sorbifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18052324]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12200.0	nM	PMID[529818]

☑ 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 NPC473307 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	250
0.1-0.2	1520
0.2-0.3	5129
0.3-0.4	11621
0.4-0.5	14940
0.5-0.6	6826
0.6-0.7	2260
0.7-0.8	135
0.8-0.85	3
0.85-0.9	5
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC153559
0.9783	High Similarity	NPC124181
0.967	High Similarity	NPC291709
0.967	High Similarity	NPC241407
0.9362	High Similarity	NPC90819
0.9271	High Similarity	NPC471599
0.9167	High Similarity	NPC219038
0.8958	High Similarity	NPC151093
0.8866	High Similarity	NPC244878
0.8776	High Similarity	NPC20673
0.8776	High Similarity	NPC4637
0.8776	High Similarity	NPC98859
0.8144	Intermediate Similarity	NPC66504
0.8021	Intermediate Similarity	NPC233997
0.7941	Intermediate Similarity	NPC255677
0.7941	Intermediate Similarity	NPC22149
0.7941	Intermediate Similarity	NPC306344
0.7864	Intermediate Similarity	NPC28304
0.7864	Intermediate Similarity	NPC298255
0.7822	Intermediate Similarity	NPC284063
0.7812	Intermediate Similarity	NPC471480
0.781	Intermediate Similarity	NPC86095
0.7788	Intermediate Similarity	NPC222062
0.7788	Intermediate Similarity	NPC195510
0.7788	Intermediate Similarity	NPC13171
0.7788	Intermediate Similarity	NPC310804
0.7788	Intermediate Similarity	NPC261117
0.7745	Intermediate Similarity	NPC86843
0.7714	Intermediate Similarity	NPC234304
0.7714	Intermediate Similarity	NPC284929
0.7714	Intermediate Similarity	NPC118761
0.7714	Intermediate Similarity	NPC267869
0.7714	Intermediate Similarity	NPC197541
0.7647	Intermediate Similarity	NPC241911
0.7642	Intermediate Similarity	NPC305157
0.7642	Intermediate Similarity	NPC307846
0.7624	Intermediate Similarity	NPC274588
0.7619	Intermediate Similarity	NPC250545
0.7549	Intermediate Similarity	NPC6765
0.7549	Intermediate Similarity	NPC93869
0.7525	Intermediate Similarity	NPC61201
0.7524	Intermediate Similarity	NPC476228
0.75	Intermediate Similarity	NPC279561
0.75	Intermediate Similarity	NPC254538
0.75	Intermediate Similarity	NPC106446
0.75	Intermediate Similarity	NPC474285
0.7476	Intermediate Similarity	NPC170527
0.7455	Intermediate Similarity	NPC193741
0.7391	Intermediate Similarity	NPC219656
0.7383	Intermediate Similarity	NPC37240
0.7383	Intermediate Similarity	NPC329834
0.7383	Intermediate Similarity	NPC475928
0.7379	Intermediate Similarity	NPC220221
0.7379	Intermediate Similarity	NPC170204
0.7368	Intermediate Similarity	NPC475946
0.7353	Intermediate Similarity	NPC320552
0.7339	Intermediate Similarity	NPC148270
0.7339	Intermediate Similarity	NPC197813
0.7339	Intermediate Similarity	NPC80338
0.7333	Intermediate Similarity	NPC472015
0.7327	Intermediate Similarity	NPC303451
0.7327	Intermediate Similarity	NPC475748
0.7327	Intermediate Similarity	NPC327253
0.7327	Intermediate Similarity	NPC6414
0.7321	Intermediate Similarity	NPC475851
0.7321	Intermediate Similarity	NPC475924
0.7308	Intermediate Similarity	NPC306041
0.73	Intermediate Similarity	NPC473151
0.729	Intermediate Similarity	NPC177013
0.729	Intermediate Similarity	NPC35185
0.729	Intermediate Similarity	NPC474730
0.729	Intermediate Similarity	NPC4899
0.7273	Intermediate Similarity	NPC204048
0.7265	Intermediate Similarity	NPC233500
0.7265	Intermediate Similarity	NPC204731
0.7264	Intermediate Similarity	NPC476211
0.7264	Intermediate Similarity	NPC473146
0.7264	Intermediate Similarity	NPC13743
0.7264	Intermediate Similarity	NPC98813
0.7264	Intermediate Similarity	NPC469402
0.7264	Intermediate Similarity	NPC476320
0.7264	Intermediate Similarity	NPC130792
0.7263	Intermediate Similarity	NPC271632
0.7257	Intermediate Similarity	NPC287075
0.7248	Intermediate Similarity	NPC170432
0.7248	Intermediate Similarity	NPC469401
0.7248	Intermediate Similarity	NPC470975
0.7248	Intermediate Similarity	NPC103088
0.7248	Intermediate Similarity	NPC470980
0.7248	Intermediate Similarity	NPC223450
0.7248	Intermediate Similarity	NPC470979
0.7241	Intermediate Similarity	NPC268326
0.7241	Intermediate Similarity	NPC153085
0.7238	Intermediate Similarity	NPC471490
0.7238	Intermediate Similarity	NPC472290
0.7228	Intermediate Similarity	NPC4986
0.7228	Intermediate Similarity	NPC64913
0.7228	Intermediate Similarity	NPC242877
0.7216	Intermediate Similarity	NPC10080
0.7216	Intermediate Similarity	NPC123908
0.7212	Intermediate Similarity	NPC167893
0.7212	Intermediate Similarity	NPC471492
0.7212	Intermediate Similarity	NPC471141
0.7203	Intermediate Similarity	NPC196130
0.72	Intermediate Similarity	NPC142583
0.72	Intermediate Similarity	NPC231889
0.72	Intermediate Similarity	NPC74139
0.7196	Intermediate Similarity	NPC473332
0.7196	Intermediate Similarity	NPC476230
0.7196	Intermediate Similarity	NPC27474
0.7196	Intermediate Similarity	NPC216911
0.7188	Intermediate Similarity	NPC474739
0.7184	Intermediate Similarity	NPC280390
0.7184	Intermediate Similarity	NPC472196
0.7184	Intermediate Similarity	NPC472195
0.7184	Intermediate Similarity	NPC238090
0.717	Intermediate Similarity	NPC203627
0.7168	Intermediate Similarity	NPC222834
0.7168	Intermediate Similarity	NPC241477
0.7157	Intermediate Similarity	NPC117596
0.7156	Intermediate Similarity	NPC474917
0.7155	Intermediate Similarity	NPC13710
0.7143	Intermediate Similarity	NPC173329
0.7143	Intermediate Similarity	NPC54731
0.7143	Intermediate Similarity	NPC170286
0.7143	Intermediate Similarity	NPC17585
0.7143	Intermediate Similarity	NPC279621
0.7143	Intermediate Similarity	NPC15551
0.7143	Intermediate Similarity	NPC219804
0.7143	Intermediate Similarity	NPC311166
0.7143	Intermediate Similarity	NPC288350
0.713	Intermediate Similarity	NPC268213
0.713	Intermediate Similarity	NPC106668
0.713	Intermediate Similarity	NPC470972
0.7129	Intermediate Similarity	NPC473658
0.7128	Intermediate Similarity	NPC301525
0.7119	Intermediate Similarity	NPC470829
0.7119	Intermediate Similarity	NPC473228
0.7117	Intermediate Similarity	NPC475960
0.7117	Intermediate Similarity	NPC110701
0.7115	Intermediate Similarity	NPC473316
0.7115	Intermediate Similarity	NPC477131
0.7115	Intermediate Similarity	NPC159698
0.7115	Intermediate Similarity	NPC473330
0.7115	Intermediate Similarity	NPC88507
0.7115	Intermediate Similarity	NPC256368
0.7105	Intermediate Similarity	NPC101400
0.7105	Intermediate Similarity	NPC101965
0.7103	Intermediate Similarity	NPC473204
0.7103	Intermediate Similarity	NPC475053
0.71	Intermediate Similarity	NPC474045
0.71	Intermediate Similarity	NPC50637
0.71	Intermediate Similarity	NPC137253
0.71	Intermediate Similarity	NPC261253
0.7091	Intermediate Similarity	NPC127235
0.7091	Intermediate Similarity	NPC85670
0.7091	Intermediate Similarity	NPC243998
0.7091	Intermediate Similarity	NPC82251
0.7087	Intermediate Similarity	NPC472124
0.7087	Intermediate Similarity	NPC9447
0.7087	Intermediate Similarity	NPC477749
0.7087	Intermediate Similarity	NPC472125
0.7087	Intermediate Similarity	NPC472126
0.708	Intermediate Similarity	NPC71680
0.7075	Intermediate Similarity	NPC2666
0.7064	Intermediate Similarity	NPC27687
0.7064	Intermediate Similarity	NPC329704
0.7064	Intermediate Similarity	NPC197736
0.7059	Intermediate Similarity	NPC151770
0.7059	Intermediate Similarity	NPC166919
0.7059	Intermediate Similarity	NPC50464
0.7059	Intermediate Similarity	NPC477748
0.7059	Intermediate Similarity	NPC307092
0.7054	Intermediate Similarity	NPC257853
0.7054	Intermediate Similarity	NPC471934
0.7048	Intermediate Similarity	NPC469543
0.7043	Intermediate Similarity	NPC305044
0.7043	Intermediate Similarity	NPC265290
0.7037	Intermediate Similarity	NPC287539
0.7037	Intermediate Similarity	NPC3488
0.7037	Intermediate Similarity	NPC198992
0.7027	Intermediate Similarity	NPC470192
0.7019	Intermediate Similarity	NPC320089
0.7018	Intermediate Similarity	NPC98038
0.7018	Intermediate Similarity	NPC471933
0.7018	Intermediate Similarity	NPC313921
0.7016	Intermediate Similarity	NPC155529
0.7009	Intermediate Similarity	NPC222303
0.7009	Intermediate Similarity	NPC476800
0.7009	Intermediate Similarity	NPC318917
0.7009	Intermediate Similarity	NPC471366
0.7009	Intermediate Similarity	NPC472186
0.7	Intermediate Similarity	NPC474547
0.7	Intermediate Similarity	NPC477510
0.7	Intermediate Similarity	NPC470658
0.7	Intermediate Similarity	NPC471143
0.7	Intermediate Similarity	NPC6193
0.699	Remote Similarity	NPC307699
0.699	Remote Similarity	NPC118078
0.699	Remote Similarity	NPC475995

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 NPC473307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1946
0.2-0.3	3849
0.3-0.4	2200
0.4-0.5	776
0.5-0.6	137
0.6-0.7	24
0.7-0.8	2
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
0.7228	Intermediate Similarity	NPD1695	Approved
0.7157	Intermediate Similarity	NPD7838	Discovery
0.7157	Intermediate Similarity	NPD46	Approved
0.7157	Intermediate Similarity	NPD6698	Approved
0.7119	Intermediate Similarity	NPD7503	Approved
0.7009	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6686	Approved
0.6875	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6648	Approved
0.6724	Remote Similarity	NPD6053	Discontinued
0.6696	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7507	Approved
0.6602	Remote Similarity	NPD4249	Approved
0.6583	Remote Similarity	NPD7327	Approved
0.6583	Remote Similarity	NPD7328	Approved
0.6557	Remote Similarity	NPD8513	Phase 3
0.6557	Remote Similarity	NPD8033	Approved
0.6538	Remote Similarity	NPD4251	Approved
0.6538	Remote Similarity	NPD4250	Approved
0.6535	Remote Similarity	NPD5209	Approved
0.6529	Remote Similarity	NPD7516	Approved
0.6496	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8294	Approved
0.6475	Remote Similarity	NPD8377	Approved
0.6457	Remote Similarity	NPD7319	Approved
0.6429	Remote Similarity	NPD5344	Discontinued
0.6423	Remote Similarity	NPD8517	Approved
0.6423	Remote Similarity	NPD8378	Approved
0.6423	Remote Similarity	NPD8515	Approved
0.6423	Remote Similarity	NPD8296	Approved
0.6423	Remote Similarity	NPD8380	Approved
0.6423	Remote Similarity	NPD8335	Approved
0.6423	Remote Similarity	NPD8379	Approved
0.6423	Remote Similarity	NPD8516	Approved
0.632	Remote Similarity	NPD7830	Approved
0.632	Remote Similarity	NPD7829	Approved
0.6311	Remote Similarity	NPD7154	Phase 3
0.6296	Remote Similarity	NPD7983	Approved
0.6293	Remote Similarity	NPD6412	Phase 2
0.6293	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7638	Approved
0.6237	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6008	Approved
0.6195	Remote Similarity	NPD7639	Approved
0.6195	Remote Similarity	NPD7640	Approved
0.6182	Remote Similarity	NPD5282	Discontinued
0.6176	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD8133	Approved
0.6098	Remote Similarity	NPD7115	Discovery
0.6095	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD7642	Approved
0.6058	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.605	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4819	Approved
0.6019	Remote Similarity	NPD4820	Approved
0.6019	Remote Similarity	NPD4822	Approved
0.6019	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD8337	Approved
0.6	Remote Similarity	NPD8336	Approved
0.598	Remote Similarity	NPD4271	Approved
0.598	Remote Similarity	NPD4268	Approved
0.5969	Remote Similarity	NPD8451	Approved
0.5965	Remote Similarity	NPD4225	Approved
0.5946	Remote Similarity	NPD5778	Approved
0.5946	Remote Similarity	NPD5779	Approved
0.5929	Remote Similarity	NPD7839	Suspended
0.5923	Remote Similarity	NPD8448	Approved
0.5923	Remote Similarity	NPD8293	Discontinued
0.5923	Remote Similarity	NPD8074	Phase 3
0.592	Remote Similarity	NPD7641	Discontinued
0.5906	Remote Similarity	NPD8444	Approved
0.5878	Remote Similarity	NPD7736	Approved
0.5859	Remote Similarity	NPD6370	Approved
0.5856	Remote Similarity	NPD5693	Phase 1
0.5849	Remote Similarity	NPD6110	Phase 1
0.5841	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.584	Remote Similarity	NPD6009	Approved
0.5821	Remote Similarity	NPD8338	Approved
0.5818	Remote Similarity	NPD6051	Approved
0.5794	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD8390	Approved
0.5789	Remote Similarity	NPD8391	Approved
0.5789	Remote Similarity	NPD8392	Approved
0.578	Remote Similarity	NPD7524	Approved
0.5772	Remote Similarity	NPD6882	Approved
0.5769	Remote Similarity	NPD8340	Approved
0.5769	Remote Similarity	NPD7492	Approved
0.5769	Remote Similarity	NPD8341	Approved
0.5769	Remote Similarity	NPD8342	Approved
0.5769	Remote Similarity	NPD8299	Approved
0.5766	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5692	Phase 3
0.5766	Remote Similarity	NPD3168	Discontinued
0.5766	Remote Similarity	NPD5785	Approved
0.5746	Remote Similarity	NPD7260	Phase 2
0.5741	Remote Similarity	NPD1694	Approved
0.5738	Remote Similarity	NPD2067	Discontinued
0.5736	Remote Similarity	NPD8080	Discontinued
0.5725	Remote Similarity	NPD6616	Approved
0.5725	Remote Similarity	NPD8273	Phase 1
0.5714	Remote Similarity	NPD6050	Approved
0.5714	Remote Similarity	NPD5694	Approved
0.5714	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD6059	Approved
0.5703	Remote Similarity	NPD6054	Approved
0.5703	Remote Similarity	NPD6319	Approved
0.5702	Remote Similarity	NPD5695	Phase 3
0.5701	Remote Similarity	NPD5331	Approved
0.5701	Remote Similarity	NPD5332	Approved
0.5701	Remote Similarity	NPD6695	Phase 3
0.5688	Remote Similarity	NPD5330	Approved
0.5688	Remote Similarity	NPD7146	Approved
0.5688	Remote Similarity	NPD6684	Approved
0.5688	Remote Similarity	NPD7521	Approved
0.5688	Remote Similarity	NPD7334	Approved
0.5688	Remote Similarity	NPD6409	Approved
0.5686	Remote Similarity	NPD8039	Approved
0.5682	Remote Similarity	NPD7078	Approved
0.5678	Remote Similarity	NPD7632	Discontinued
0.566	Remote Similarity	NPD4790	Discontinued
0.5659	Remote Similarity	NPD6016	Approved
0.5659	Remote Similarity	NPD6015	Approved
0.5645	Remote Similarity	NPD8297	Approved
0.5625	Remote Similarity	NPD5207	Approved
0.5615	Remote Similarity	NPD5988	Approved
0.5607	Remote Similarity	NPD6435	Approved
0.5603	Remote Similarity	NPD6083	Phase 2
0.5603	Remote Similarity	NPD6084	Phase 2
0.56	Remote Similarity	NPD4632	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