NPASS Compound

Structure

NPC473314 OpenBabel07101718302D 24 26 0 0 1 0 0 0 0 0999 V2000 3.5470 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0194 2.6381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7916 -0.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3115 0.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2354 -1.0241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5847 -1.4052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8315 -1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6905 0.3676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8037 1.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3410 1.4648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6345 -0.3843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0639 1.6791 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8315 -1.4402 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3907 1.0595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8315 -0.4801 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1996 0.9391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5450 0.1624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8315 -0.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1545 1.0395 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1547 1.6410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4841 -0.0372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9097 0.2007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 14 6 1 6 0 0 0 14 19 1 0 0 0 0 15 22 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	333.23
Volume:	358.265
LogP:	3.088
LogD:	2.947
LogS:	-4.348
# Rotatable Bonds:	0
TPSA:	69.89
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.668
Synthetic Accessibility Score:	5.968
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.816
MDCK Permeability:	1.1301568520138972e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.512
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.923
Plasma Protein Binding (PPB):	59.43500518798828%
Volume Distribution (VD):	1.079
Pgp-substrate:	45.01137924194336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.486
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.541
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	6.731
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.775
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.245
Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.079
Carcinogencity:	0.952
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC473314

Natural Product ID:	NPC473314
*Common Name:**	Cespitulactam I
IUPAC Name:	n.a.
Synonyms:	Cespitulactam I
Standard InCHIKey:	XOASOLHOOJVMAH-VJBSFRMPSA-N
Standard InCHI:	InChI=1S/C20H31NO3/c1-12-5-6-14-7-8-16-18(23)21-17(20(16,24)19(14,3)4)11-13(2)10-15(22)9-12/h11,13-16,22,24H,1,5-10H2,2-4H3,(H,21,23)/b17-11+/t13?,14-,15+,16?,20?/m1/s1
SMILES:	CC1CC(CC(=C)CCC2CCC3C(=O)NC(=C1)C3(C2(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399728
PubChem CID:	44445426
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO2560	Cespitularia taeniata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16495058]
NPO2560	Cespitularia taeniata	Species	Xeniidae	Eukaryota	n.a.	Taiwanese soft coral	n.a.	PMID[18052327]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	4.16	ug.mL-1	PMID[487704]

☑ 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 NPC473314 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	85
0.1-0.2	648
0.2-0.3	5905
0.3-0.4	19911
0.4-0.5	10606
0.5-0.6	4920
0.6-0.7	601
0.7-0.8	20
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8172	Intermediate Similarity	NPC34754
0.7353	Intermediate Similarity	NPC240650
0.7353	Intermediate Similarity	NPC4834
0.7333	Intermediate Similarity	NPC293299
0.7333	Intermediate Similarity	NPC45365
0.7333	Intermediate Similarity	NPC474583
0.7238	Intermediate Similarity	NPC247060
0.7238	Intermediate Similarity	NPC471083
0.7238	Intermediate Similarity	NPC50815
0.7196	Intermediate Similarity	NPC55462
0.7111	Intermediate Similarity	NPC220939
0.7111	Intermediate Similarity	NPC265485
0.7091	Intermediate Similarity	NPC472359
0.7065	Intermediate Similarity	NPC265588
0.7059	Intermediate Similarity	NPC280710
0.7059	Intermediate Similarity	NPC243985
0.7033	Intermediate Similarity	NPC201048
0.7033	Intermediate Similarity	NPC476366
0.7009	Intermediate Similarity	NPC474563
0.7009	Intermediate Similarity	NPC90538
0.7	Intermediate Similarity	NPC477792
0.6989	Remote Similarity	NPC91594
0.6989	Remote Similarity	NPC470758
0.6989	Remote Similarity	NPC470711
0.6979	Remote Similarity	NPC155521
0.6972	Remote Similarity	NPC25340
0.6957	Remote Similarity	NPC32832
0.6937	Remote Similarity	NPC328052
0.6909	Remote Similarity	NPC307903
0.6909	Remote Similarity	NPC140251
0.6889	Remote Similarity	NPC34834
0.6887	Remote Similarity	NPC275686
0.6882	Remote Similarity	NPC470749
0.6869	Remote Similarity	NPC6391
0.6869	Remote Similarity	NPC474458
0.6837	Remote Similarity	NPC205845
0.6818	Remote Similarity	NPC169375
0.6814	Remote Similarity	NPC56796
0.6813	Remote Similarity	NPC167706
0.6813	Remote Similarity	NPC471272
0.6813	Remote Similarity	NPC23954
0.6804	Remote Similarity	NPC101462
0.6804	Remote Similarity	NPC39966
0.6804	Remote Similarity	NPC49964
0.6804	Remote Similarity	NPC87489
0.6804	Remote Similarity	NPC218616
0.6804	Remote Similarity	NPC296701
0.6786	Remote Similarity	NPC113012
0.6786	Remote Similarity	NPC122926
0.6774	Remote Similarity	NPC133580
0.6742	Remote Similarity	NPC114651
0.6737	Remote Similarity	NPC11908
0.6735	Remote Similarity	NPC470384
0.6703	Remote Similarity	NPC92801
0.6701	Remote Similarity	NPC476646
0.6701	Remote Similarity	NPC475724
0.6701	Remote Similarity	NPC264245
0.6701	Remote Similarity	NPC249423
0.67	Remote Similarity	NPC261266
0.67	Remote Similarity	NPC470365
0.6667	Remote Similarity	NPC238485
0.6667	Remote Similarity	NPC470361
0.6667	Remote Similarity	NPC83702
0.6667	Remote Similarity	NPC306727
0.6667	Remote Similarity	NPC96484
0.6667	Remote Similarity	NPC30986
0.6667	Remote Similarity	NPC475800
0.6667	Remote Similarity	NPC231310
0.6667	Remote Similarity	NPC209430
0.6667	Remote Similarity	NPC81306
0.6667	Remote Similarity	NPC109546
0.6667	Remote Similarity	NPC143182
0.6667	Remote Similarity	NPC47982
0.6667	Remote Similarity	NPC84694
0.6667	Remote Similarity	NPC471238
0.6667	Remote Similarity	NPC185568
0.6667	Remote Similarity	NPC276616
0.6667	Remote Similarity	NPC28862
0.6637	Remote Similarity	NPC476290
0.6636	Remote Similarity	NPC234542
0.6634	Remote Similarity	NPC149224
0.6633	Remote Similarity	NPC202389
0.6633	Remote Similarity	NPC224072
0.6632	Remote Similarity	NPC477427
0.6632	Remote Similarity	NPC474826
0.6632	Remote Similarity	NPC31037
0.6632	Remote Similarity	NPC477426
0.6632	Remote Similarity	NPC477425
0.663	Remote Similarity	NPC164022
0.663	Remote Similarity	NPC471268
0.663	Remote Similarity	NPC471271
0.6629	Remote Similarity	NPC202017
0.6602	Remote Similarity	NPC291484
0.6602	Remote Similarity	NPC329596
0.6602	Remote Similarity	NPC3345
0.6602	Remote Similarity	NPC78973
0.6602	Remote Similarity	NPC11216
0.6602	Remote Similarity	NPC80561
0.6602	Remote Similarity	NPC204188
0.66	Remote Similarity	NPC274448
0.66	Remote Similarity	NPC266511
0.66	Remote Similarity	NPC470360
0.6598	Remote Similarity	NPC209944
0.6598	Remote Similarity	NPC164840
0.6598	Remote Similarity	NPC234193
0.6598	Remote Similarity	NPC295131
0.6598	Remote Similarity	NPC241290
0.6598	Remote Similarity	NPC96362
0.6596	Remote Similarity	NPC313185
0.6593	Remote Similarity	NPC474248
0.6593	Remote Similarity	NPC471560
0.6591	Remote Similarity	NPC225415
0.6574	Remote Similarity	NPC473224
0.6569	Remote Similarity	NPC316186
0.6569	Remote Similarity	NPC67872
0.6569	Remote Similarity	NPC324405
0.6566	Remote Similarity	NPC317458
0.6566	Remote Similarity	NPC185605
0.6566	Remote Similarity	NPC474634
0.6566	Remote Similarity	NPC475789
0.6566	Remote Similarity	NPC82623
0.6562	Remote Similarity	NPC474216
0.6562	Remote Similarity	NPC83351
0.6562	Remote Similarity	NPC167891
0.6562	Remote Similarity	NPC476314
0.6562	Remote Similarity	NPC285761
0.6562	Remote Similarity	NPC275910
0.6556	Remote Similarity	NPC69649
0.6556	Remote Similarity	NPC68703
0.6549	Remote Similarity	NPC474725
0.6538	Remote Similarity	NPC97404
0.6538	Remote Similarity	NPC41554
0.6535	Remote Similarity	NPC293287
0.6535	Remote Similarity	NPC299068
0.6535	Remote Similarity	NPC152808
0.6531	Remote Similarity	NPC209620
0.6531	Remote Similarity	NPC23852
0.6531	Remote Similarity	NPC471270
0.6531	Remote Similarity	NPC159148
0.6531	Remote Similarity	NPC47761
0.6526	Remote Similarity	NPC253190
0.6526	Remote Similarity	NPC247325
0.6526	Remote Similarity	NPC244488
0.6522	Remote Similarity	NPC476269
0.6522	Remote Similarity	NPC283316
0.6522	Remote Similarity	NPC469968
0.6522	Remote Similarity	NPC80834
0.6517	Remote Similarity	NPC258595
0.6514	Remote Similarity	NPC77703
0.6505	Remote Similarity	NPC257485
0.65	Remote Similarity	NPC474047
0.65	Remote Similarity	NPC242692
0.65	Remote Similarity	NPC470077
0.6495	Remote Similarity	NPC472463
0.6495	Remote Similarity	NPC273410
0.6495	Remote Similarity	NPC291379
0.6495	Remote Similarity	NPC80530
0.6495	Remote Similarity	NPC53744
0.6489	Remote Similarity	NPC477138
0.6489	Remote Similarity	NPC309178
0.6489	Remote Similarity	NPC471797
0.6489	Remote Similarity	NPC243342
0.6489	Remote Similarity	NPC91858
0.6484	Remote Similarity	NPC208999
0.6476	Remote Similarity	NPC310013
0.6471	Remote Similarity	NPC470620
0.6471	Remote Similarity	NPC476948
0.6471	Remote Similarity	NPC166857
0.6465	Remote Similarity	NPC109938
0.6465	Remote Similarity	NPC2524
0.6465	Remote Similarity	NPC470049
0.6465	Remote Similarity	NPC122945
0.6465	Remote Similarity	NPC189972
0.6465	Remote Similarity	NPC50964
0.6465	Remote Similarity	NPC471408
0.6465	Remote Similarity	NPC30166
0.6458	Remote Similarity	NPC477924
0.6458	Remote Similarity	NPC155986
0.6458	Remote Similarity	NPC318495
0.6458	Remote Similarity	NPC214570
0.6458	Remote Similarity	NPC471798
0.6458	Remote Similarity	NPC198968
0.6452	Remote Similarity	NPC242992
0.6452	Remote Similarity	NPC242001
0.6449	Remote Similarity	NPC475503
0.6446	Remote Similarity	NPC469943
0.6444	Remote Similarity	NPC326310
0.6442	Remote Similarity	NPC270511
0.6442	Remote Similarity	NPC295668
0.6442	Remote Similarity	NPC470390
0.6442	Remote Similarity	NPC245410
0.6442	Remote Similarity	NPC14380
0.6442	Remote Similarity	NPC192437
0.6436	Remote Similarity	NPC157257
0.6436	Remote Similarity	NPC318390
0.6429	Remote Similarity	NPC471266
0.6429	Remote Similarity	NPC13554
0.6429	Remote Similarity	NPC474592
0.6429	Remote Similarity	NPC206062
0.6429	Remote Similarity	NPC102253

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 NPC473314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	91
0.1-0.2	432
0.2-0.3	3304
0.3-0.4	4016
0.4-0.5	1103
0.5-0.6	184
0.6-0.7	20
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
0.6491	Remote Similarity	NPD6420	Discontinued
0.6429	Remote Similarity	NPD6931	Approved
0.6429	Remote Similarity	NPD6930	Phase 2
0.6429	Remote Similarity	NPD7525	Registered
0.6415	Remote Similarity	NPD5771	Approved
0.6354	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6929	Approved
0.6327	Remote Similarity	NPD7645	Phase 2
0.6316	Remote Similarity	NPD6926	Approved
0.6316	Remote Similarity	NPD6924	Approved
0.6311	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7332	Phase 2
0.6263	Remote Similarity	NPD7514	Phase 3
0.625	Remote Similarity	NPD4722	Approved
0.625	Remote Similarity	NPD8264	Approved
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD6942	Approved
0.625	Remote Similarity	NPD4723	Approved
0.6238	Remote Similarity	NPD6695	Phase 3
0.6224	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6933	Approved
0.6186	Remote Similarity	NPD1346	Approved
0.618	Remote Similarity	NPD368	Approved
0.6176	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7505	Discontinued
0.614	Remote Similarity	NPD5357	Phase 1
0.614	Remote Similarity	NPD6640	Phase 3
0.6126	Remote Similarity	NPD6404	Discontinued
0.6122	Remote Similarity	NPD6925	Approved
0.6122	Remote Similarity	NPD5776	Phase 2
0.6117	Remote Similarity	NPD6893	Approved
0.61	Remote Similarity	NPD7509	Discontinued
0.6061	Remote Similarity	NPD7145	Approved
0.604	Remote Similarity	NPD6902	Approved
0.604	Remote Similarity	NPD6898	Phase 1
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD7524	Approved
0.598	Remote Similarity	NPD3667	Approved
0.596	Remote Similarity	NPD6932	Approved
0.5941	Remote Similarity	NPD4748	Discontinued
0.5929	Remote Similarity	NPD4159	Approved
0.5905	Remote Similarity	NPD3618	Phase 1
0.5895	Remote Similarity	NPD6922	Approved
0.5895	Remote Similarity	NPD6923	Approved
0.5895	Remote Similarity	NPD15	Approved
0.5895	Remote Similarity	NPD1082	Approved
0.5895	Remote Similarity	NPD791	Approved
0.5893	Remote Similarity	NPD4225	Approved
0.5882	Remote Similarity	NPD1719	Phase 1
0.5865	Remote Similarity	NPD4786	Approved
0.5846	Remote Similarity	NPD6914	Discontinued
0.5842	Remote Similarity	NPD6683	Phase 2
0.5833	Remote Similarity	NPD3168	Discontinued
0.5833	Remote Similarity	NPD7143	Approved
0.5833	Remote Similarity	NPD7144	Approved
0.5833	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4785	Approved
0.5816	Remote Similarity	NPD4784	Approved
0.5798	Remote Similarity	NPD6421	Discontinued
0.578	Remote Similarity	NPD7087	Discontinued
0.5773	Remote Similarity	NPD4243	Approved
0.5773	Remote Similarity	NPD7150	Approved
0.5773	Remote Similarity	NPD7151	Approved
0.5773	Remote Similarity	NPD7152	Approved
0.575	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5328	Approved
0.5739	Remote Similarity	NPD5211	Phase 2
0.5739	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD4202	Approved
0.5714	Remote Similarity	NPD3133	Approved
0.5714	Remote Similarity	NPD4732	Discontinued
0.5714	Remote Similarity	NPD3665	Phase 1
0.5714	Remote Similarity	NPD3666	Approved
0.5702	Remote Similarity	NPD7639	Approved
0.5702	Remote Similarity	NPD7640	Approved
0.5682	Remote Similarity	NPD342	Phase 1
0.568	Remote Similarity	NPD7522	Discontinued
0.5676	Remote Similarity	NPD5707	Approved
0.5664	Remote Similarity	NPD4755	Approved
0.5662	Remote Similarity	NPD6334	Approved
0.5662	Remote Similarity	NPD6333	Approved
0.566	Remote Similarity	NPD1696	Phase 3
0.5641	Remote Similarity	NPD5141	Approved
0.5636	Remote Similarity	NPD6079	Approved
0.5634	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6406	Approved
0.5625	Remote Similarity	NPD6705	Phase 1
0.5614	Remote Similarity	NPD7638	Approved
0.5607	Remote Similarity	NPD4519	Discontinued
0.5607	Remote Similarity	NPD4623	Approved
0.56	Remote Similarity	NPD5275	Approved
0.56	Remote Similarity	NPD4190	Phase 3

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