NPASS Compound

Structure

NPC50464 OpenBabel07101719522D 27 29 0 0 1 0 0 0 0 0999 V2000 -1.5620 2.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.9563 0.0000 C 0 0 0 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 -3.4641 -2.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5130 2.2653 0.0000 C 0 0 0 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 -5.0733 0.1691 0.0000 C 0 0 1 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 2 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 -3.6720 0.9781 0.0000 C 0 0 1 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 -3.2562 2.9344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0514 -0.0388 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 -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 -2.7210 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 3 4 2 0 0 0 0 4 24 1 0 0 0 0 5 9 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 7 27 1 0 0 0 0 8 3 1 6 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 9 20 1 1 0 0 0 10 6 1 6 0 0 0 10 12 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 6 0 0 0 12 13 1 0 0 0 0 12 21 1 1 0 0 0 13 14 1 0 0 0 0 13 22 1 6 0 0 0 14 16 1 0 0 0 0 14 23 1 1 0 0 0 15 24 1 0 0 0 0 15 26 1 1 0 0 0 16 25 1 0 0 0 0 16 26 1 6 0 0 0 17 2 1 6 0 0 0 17 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.15
Volume:	359.548
LogP:	-0.91
LogD:	-0.032
LogS:	-1.314
# Rotatable Bonds:	5
TPSA:	155.14
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	4.985
Fsp3:	0.824
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:	-6.244
MDCK Permeability:	0.00013815407874062657
Pgp-inhibitor:	0.002
Pgp-substrate:	0.952
Human Intestinal Absorption (HIA):	0.964
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	22.285839080810547%
Volume Distribution (VD):	0.336
Pgp-substrate:	61.879478454589844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.456
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	1.395
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.149
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.12
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.724

Download Data

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

Natural Product: NPC50464

Natural Product ID:	NPC50464
*Common Name:**	[(1R,4As,5S,7R,7Ar)-5-Hydroxy-7-Methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-4A,5,6,7A-Tetrahydro-1H-Cyclopenta[C]Pyran-7-Yl] Acetate
IUPAC Name:	[(1R,4aS,5S,7R,7aR)-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-7-yl] acetate
Synonyms:
Standard InCHIKey:	FLOXQRMTDDOZKF-POQLYTHUSA-N
Standard InCHI:	InChI=1S/C17H26O10/c1-7(19)27-17(2)5-9(20)8-3-4-24-15(11(8)17)26-16-14(23)13(22)12(21)10(6-18)25-16/h3-4,8-16,18,20-23H,5-6H2,1-2H3/t8-,9+,10-,11+,12-,13+,14-,15-,16+,17-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2OC=C[C@H]3[C@@H]2[C@](C)(OC(=O)C)C[C@@H]3O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL605532
PubChem CID:	46227125
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
NPO33377	teucrium chamaedris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19674906]

☑ 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	4
Others	3

Activity Type	# Activity
NON-MOLECULAR	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.3	n.a.	PMID[558997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.7	n.a.	PMID[558997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.8	n.a.	PMID[558997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	38900.0	nM	PMID[558997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	44200.0	nM	PMID[558997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	52200.0	nM	PMID[558997]
NPT1	Others	Radical scavenging activity		IC50	>	300000.0	nM	PMID[558997]

☑ 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 NPC50464 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	171
0.1-0.2	1788
0.2-0.3	7001
0.3-0.4	15096
0.4-0.5	8869
0.5-0.6	7554
0.6-0.7	2043
0.7-0.8	139
0.8-0.85	21
0.85-0.9	7
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC294643
0.9535	High Similarity	NPC274274
0.9535	High Similarity	NPC473150
0.9529	High Similarity	NPC93190
0.9398	High Similarity	NPC259296
0.9398	High Similarity	NPC98276
0.908	High Similarity	NPC22918
0.8966	High Similarity	NPC148534
0.8953	High Similarity	NPC171484
0.8953	High Similarity	NPC149018
0.8851	High Similarity	NPC258501
0.8667	High Similarity	NPC276298
0.8404	Intermediate Similarity	NPC470684
0.8404	Intermediate Similarity	NPC470683
0.8191	Intermediate Similarity	NPC6765
0.8191	Intermediate Similarity	NPC93869
0.8182	Intermediate Similarity	NPC127235
0.81	Intermediate Similarity	NPC80338
0.81	Intermediate Similarity	NPC148270
0.81	Intermediate Similarity	NPC197813
0.8085	Intermediate Similarity	NPC274588
0.8065	Intermediate Similarity	NPC235051
0.798	Intermediate Similarity	NPC475928
0.798	Intermediate Similarity	NPC37240
0.7959	Intermediate Similarity	NPC3488
0.7959	Intermediate Similarity	NPC287539
0.7959	Intermediate Similarity	NPC216911
0.7917	Intermediate Similarity	NPC284063
0.7917	Intermediate Similarity	NPC170527
0.7917	Intermediate Similarity	NPC161293
0.7879	Intermediate Similarity	NPC474730
0.7879	Intermediate Similarity	NPC4899
0.7879	Intermediate Similarity	NPC177013
0.7879	Intermediate Similarity	NPC35185
0.7864	Intermediate Similarity	NPC193741
0.7857	Intermediate Similarity	NPC244878
0.7857	Intermediate Similarity	NPC476211
0.7857	Intermediate Similarity	NPC476320
0.7835	Intermediate Similarity	NPC86843
0.7822	Intermediate Similarity	NPC170432
0.78	Intermediate Similarity	NPC329834
0.7778	Intermediate Similarity	NPC20673
0.7778	Intermediate Similarity	NPC476230
0.7778	Intermediate Similarity	NPC27474
0.7766	Intermediate Similarity	NPC117596
0.7755	Intermediate Similarity	NPC151093
0.7714	Intermediate Similarity	NPC475851
0.7714	Intermediate Similarity	NPC475924
0.7708	Intermediate Similarity	NPC63897
0.77	Intermediate Similarity	NPC304163
0.7692	Intermediate Similarity	NPC220167
0.7692	Intermediate Similarity	NPC136699
0.7684	Intermediate Similarity	NPC472124
0.7684	Intermediate Similarity	NPC472126
0.7684	Intermediate Similarity	NPC472125
0.767	Intermediate Similarity	NPC110701
0.7653	Intermediate Similarity	NPC472290
0.7653	Intermediate Similarity	NPC263674
0.7653	Intermediate Similarity	NPC58267
0.7653	Intermediate Similarity	NPC261372
0.7624	Intermediate Similarity	NPC329704
0.7615	Intermediate Similarity	NPC219656
0.7604	Intermediate Similarity	NPC280390
0.7604	Intermediate Similarity	NPC61201
0.76	Intermediate Similarity	NPC219038
0.76	Intermediate Similarity	NPC4637
0.76	Intermediate Similarity	NPC476228
0.76	Intermediate Similarity	NPC98859
0.7579	Intermediate Similarity	NPC307699
0.7576	Intermediate Similarity	NPC37866
0.7576	Intermediate Similarity	NPC157739
0.7551	Intermediate Similarity	NPC241911
0.7525	Intermediate Similarity	NPC106668
0.7525	Intermediate Similarity	NPC471599
0.75	Intermediate Similarity	NPC306344
0.75	Intermediate Similarity	NPC66504
0.75	Intermediate Similarity	NPC255677
0.75	Intermediate Similarity	NPC22149
0.7477	Intermediate Similarity	NPC233500
0.7475	Intermediate Similarity	NPC473555
0.7475	Intermediate Similarity	NPC471770
0.7475	Intermediate Similarity	NPC278939
0.7451	Intermediate Similarity	NPC27687
0.7449	Intermediate Similarity	NPC101051
0.7426	Intermediate Similarity	NPC28304
0.7426	Intermediate Similarity	NPC298255
0.7419	Intermediate Similarity	NPC477746
0.7419	Intermediate Similarity	NPC477747
0.7411	Intermediate Similarity	NPC196130
0.7386	Intermediate Similarity	NPC279575
0.7379	Intermediate Similarity	NPC86095
0.7374	Intermediate Similarity	NPC474297
0.7364	Intermediate Similarity	NPC472080
0.7353	Intermediate Similarity	NPC154452
0.7353	Intermediate Similarity	NPC195510
0.7353	Intermediate Similarity	NPC13171
0.7353	Intermediate Similarity	NPC261117
0.7353	Intermediate Similarity	NPC310804
0.7353	Intermediate Similarity	NPC222062
0.7345	Intermediate Similarity	NPC219804
0.734	Intermediate Similarity	NPC470657
0.7333	Intermediate Similarity	NPC170595
0.7333	Intermediate Similarity	NPC295980
0.7327	Intermediate Similarity	NPC317019
0.7327	Intermediate Similarity	NPC473146
0.73	Intermediate Similarity	NPC304445
0.73	Intermediate Similarity	NPC236580
0.7282	Intermediate Similarity	NPC118761
0.7282	Intermediate Similarity	NPC197541
0.7282	Intermediate Similarity	NPC234304
0.7282	Intermediate Similarity	NPC284929
0.7282	Intermediate Similarity	NPC267869
0.7273	Intermediate Similarity	NPC291709
0.7273	Intermediate Similarity	NPC241407
0.7264	Intermediate Similarity	NPC208307
0.7263	Intermediate Similarity	NPC31349
0.7255	Intermediate Similarity	NPC21064
0.7255	Intermediate Similarity	NPC121072
0.7245	Intermediate Similarity	NPC470187
0.7245	Intermediate Similarity	NPC474835
0.7238	Intermediate Similarity	NPC470169
0.7238	Intermediate Similarity	NPC470170
0.7234	Intermediate Similarity	NPC470658
0.7228	Intermediate Similarity	NPC469918
0.7228	Intermediate Similarity	NPC96399
0.7228	Intermediate Similarity	NPC117066
0.7228	Intermediate Similarity	NPC469919
0.7228	Intermediate Similarity	NPC223700
0.7216	Intermediate Similarity	NPC216826
0.7216	Intermediate Similarity	NPC270908
0.7216	Intermediate Similarity	NPC470573
0.7216	Intermediate Similarity	NPC231710
0.7216	Intermediate Similarity	NPC120021
0.7216	Intermediate Similarity	NPC65665
0.7184	Intermediate Similarity	NPC250545
0.7156	Intermediate Similarity	NPC287075
0.7143	Intermediate Similarity	NPC473199
0.713	Intermediate Similarity	NPC114188
0.713	Intermediate Similarity	NPC470748
0.7129	Intermediate Similarity	NPC153559
0.7129	Intermediate Similarity	NPC76486
0.7115	Intermediate Similarity	NPC197736
0.7113	Intermediate Similarity	NPC299527
0.7113	Intermediate Similarity	NPC104129
0.7113	Intermediate Similarity	NPC477748
0.7113	Intermediate Similarity	NPC249408
0.7097	Intermediate Similarity	NPC20072
0.7094	Intermediate Similarity	NPC145287
0.7094	Intermediate Similarity	NPC163783
0.7091	Intermediate Similarity	NPC106446
0.7087	Intermediate Similarity	NPC67296
0.7083	Intermediate Similarity	NPC316629
0.7075	Intermediate Similarity	NPC470166
0.7065	Intermediate Similarity	NPC100697
0.7059	Intermediate Similarity	NPC90819
0.7059	Intermediate Similarity	NPC124181
0.7059	Intermediate Similarity	NPC473307
0.7059	Intermediate Similarity	NPC249171
0.7059	Intermediate Similarity	NPC49833
0.7054	Intermediate Similarity	NPC475357
0.7045	Intermediate Similarity	NPC470660
0.7045	Intermediate Similarity	NPC470659
0.7041	Intermediate Similarity	NPC327253
0.7041	Intermediate Similarity	NPC303451
0.7041	Intermediate Similarity	NPC202886
0.7041	Intermediate Similarity	NPC6414
0.7037	Intermediate Similarity	NPC106760
0.7027	Intermediate Similarity	NPC477031
0.7019	Intermediate Similarity	NPC94919
0.7009	Intermediate Similarity	NPC38217
0.7009	Intermediate Similarity	NPC472988
0.7	Intermediate Similarity	NPC256368
0.7	Intermediate Similarity	NPC96736
0.7	Intermediate Similarity	NPC178949
0.7	Intermediate Similarity	NPC144068
0.6991	Remote Similarity	NPC5883
0.6991	Remote Similarity	NPC44899
0.6991	Remote Similarity	NPC29639
0.6991	Remote Similarity	NPC304260
0.699	Remote Similarity	NPC130792
0.699	Remote Similarity	NPC91497
0.6989	Remote Similarity	NPC216941
0.6981	Remote Similarity	NPC474569
0.6981	Remote Similarity	NPC165405
0.6975	Remote Similarity	NPC276047
0.6975	Remote Similarity	NPC267733
0.697	Remote Similarity	NPC48463
0.697	Remote Similarity	NPC472197
0.697	Remote Similarity	NPC472199
0.697	Remote Similarity	NPC477749
0.6964	Remote Similarity	NPC203862
0.6961	Remote Similarity	NPC91197
0.6961	Remote Similarity	NPC96597
0.6961	Remote Similarity	NPC476612
0.6961	Remote Similarity	NPC155319
0.6961	Remote Similarity	NPC125551
0.6961	Remote Similarity	NPC347923
0.6961	Remote Similarity	NPC239547
0.6961	Remote Similarity	NPC476057
0.6961	Remote Similarity	NPC476613

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 NPC50464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	2391
0.2-0.3	4107
0.3-0.4	1726
0.4-0.5	455
0.5-0.6	289
0.6-0.7	39
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
0.7168	Intermediate Similarity	NPD7503	Approved
0.7158	Intermediate Similarity	NPD4249	Approved
0.7083	Intermediate Similarity	NPD4251	Approved
0.7083	Intermediate Similarity	NPD4250	Approved
0.687	Remote Similarity	NPD8033	Approved
0.6754	Remote Similarity	NPD7327	Approved
0.6754	Remote Similarity	NPD7328	Approved
0.6702	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7516	Approved
0.6638	Remote Similarity	NPD8377	Approved
0.6638	Remote Similarity	NPD8294	Approved
0.6606	Remote Similarity	NPD6412	Phase 2
0.6581	Remote Similarity	NPD8296	Approved
0.6581	Remote Similarity	NPD8335	Approved
0.6581	Remote Similarity	NPD8380	Approved
0.6581	Remote Similarity	NPD8379	Approved
0.6581	Remote Similarity	NPD8378	Approved
0.6549	Remote Similarity	NPD8133	Approved
0.6526	Remote Similarity	NPD4822	Approved
0.6526	Remote Similarity	NPD4821	Approved
0.6526	Remote Similarity	NPD4819	Approved
0.6526	Remote Similarity	NPD4820	Approved
0.6489	Remote Similarity	NPD4268	Approved
0.6489	Remote Similarity	NPD4271	Approved
0.6415	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6686	Approved
0.6392	Remote Similarity	NPD6435	Approved
0.6372	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7507	Approved
0.6316	Remote Similarity	NPD6053	Discontinued
0.6303	Remote Similarity	NPD8513	Phase 3
0.6214	Remote Similarity	NPD46	Approved
0.6214	Remote Similarity	NPD6698	Approved
0.621	Remote Similarity	NPD7319	Approved
0.6186	Remote Similarity	NPD5368	Approved
0.6167	Remote Similarity	NPD8516	Approved
0.6167	Remote Similarity	NPD8517	Approved
0.6167	Remote Similarity	NPD8515	Approved
0.6162	Remote Similarity	NPD7154	Phase 3
0.6122	Remote Similarity	NPD5369	Approved
0.6095	Remote Similarity	NPD8171	Discontinued
0.6078	Remote Similarity	NPD7524	Approved
0.6058	Remote Similarity	NPD7838	Discovery
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD7983	Approved
0.5984	Remote Similarity	NPD6370	Approved
0.5982	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6009	Approved
0.595	Remote Similarity	NPD6319	Approved
0.5941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.592	Remote Similarity	NPD8293	Discontinued
0.5914	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6882	Approved
0.5887	Remote Similarity	NPD7492	Approved
0.5882	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5344	Discontinued
0.5847	Remote Similarity	NPD4632	Approved
0.5842	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3669	Approved
0.5842	Remote Similarity	NPD5331	Approved
0.5842	Remote Similarity	NPD5332	Approved
0.5842	Remote Similarity	NPD6695	Phase 3
0.5841	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.584	Remote Similarity	NPD6616	Approved
0.582	Remote Similarity	NPD6054	Approved
0.58	Remote Similarity	NPD4790	Discontinued
0.5794	Remote Similarity	NPD7078	Approved
0.5785	Remote Similarity	NPD7641	Discontinued
0.5784	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6016	Approved
0.5772	Remote Similarity	NPD6015	Approved
0.5772	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD8297	Approved
0.576	Remote Similarity	NPD8342	Approved
0.576	Remote Similarity	NPD8341	Approved
0.576	Remote Similarity	NPD8340	Approved
0.576	Remote Similarity	NPD8299	Approved
0.5743	Remote Similarity	NPD4270	Approved
0.5743	Remote Similarity	NPD4269	Approved
0.5741	Remote Similarity	NPD5282	Discontinued
0.5726	Remote Similarity	NPD8080	Discontinued
0.5726	Remote Similarity	NPD5988	Approved
0.5726	Remote Similarity	NPD6371	Approved
0.5714	Remote Similarity	NPD893	Approved
0.5714	Remote Similarity	NPD889	Approved
0.5714	Remote Similarity	NPD8451	Approved
0.5714	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD892	Phase 3
0.5714	Remote Similarity	NPD894	Approved
0.5714	Remote Similarity	NPD891	Phase 3
0.5714	Remote Similarity	NPD888	Phase 3
0.5714	Remote Similarity	NPD895	Approved
0.5714	Remote Similarity	NPD6932	Approved
0.5714	Remote Similarity	NPD887	Approved
0.57	Remote Similarity	NPD4252	Approved
0.5698	Remote Similarity	NPD2267	Suspended
0.5691	Remote Similarity	NPD6059	Approved
0.568	Remote Similarity	NPD7829	Approved
0.568	Remote Similarity	NPD7830	Approved
0.5673	Remote Similarity	NPD5786	Approved
0.5669	Remote Similarity	NPD8074	Phase 3
0.5669	Remote Similarity	NPD8448	Approved
0.5663	Remote Similarity	NPD905	Approved
0.5663	Remote Similarity	NPD904	Phase 3
0.5645	Remote Similarity	NPD8444	Approved
0.5636	Remote Similarity	NPD7839	Suspended
0.5619	Remote Similarity	NPD7750	Discontinued
0.5612	Remote Similarity	NPD6933	Approved
0.5607	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD6685	Approved
0.5603	Remote Similarity	NPD5697	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