NPASS Compound

Structure

NPC34754 OpenBabel07101719122D 23 25 0 0 1 0 0 0 0 0999 V2000 4.8968 -1.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2642 1.6651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5307 -2.1493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8530 -2.5462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 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 4.0047 -0.6998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0810 0.5138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5576 0.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9464 -1.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3106 0.6662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6925 0.0209 0.0000 C 0 0 1 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 0.9945 -0.1045 0.0000 C 0 0 2 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 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4882 0.6265 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 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 20 1 0 0 0 0 4 20 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 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 14 6 1 6 0 0 0 14 20 1 0 0 0 0 15 22 1 1 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 11 1 6 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.22
Volume:	346.838
LogP:	4.648
LogD:	3.866
LogS:	-4.973
# Rotatable Bonds:	0
TPSA:	56.25
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	5.835
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.089
MDCK Permeability:	1.0656616723281331e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.185
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.81
Plasma Protein Binding (PPB):	95.30963897705078%
Volume Distribution (VD):	1.24
Pgp-substrate:	3.37943696975708%

ADMET: Metabolism

CYP1A2-inhibitor:	0.186
CYP1A2-substrate:	0.43
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.331
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.395
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.413
CYP3A4-substrate:	0.377

ADMET: Excretion

Clearance (CL):	8.794
Half-life (T1/2):	0.31

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.61
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.848
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.792
Carcinogencity:	0.891
Eye Corrosion:	0.003
Eye Irritation:	0.077
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC34754

Natural Product ID:	NPC34754
*Common Name:**	Cespitulactam D
IUPAC Name:	n.a.
Synonyms:	Cespitulactam D
Standard InCHIKey:	DZPGQVGXKGIMGH-CZIVKBJPSA-N
Standard InCHI:	InChI=1S/C20H29NO2/c1-12-5-6-14-7-8-16-18(20(14,3)4)17(21-19(16)23)11-13(2)10-15(22)9-12/h10,14-15,17,22H,1,5-9,11H2,2-4H3,(H,21,23)/b13-10+/t14-,15+,17-/m1/s1
SMILES:	C=C1CC[C@@H]2CCC3=C(C2(C)C)[C@@H](C/C(=C/[C@H](C1)O)/C)N=C3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251660
PubChem CID:	24762910
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
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	4.16	ug.mL-1	PMID[559579]

☑ 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 NPC34754 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	70
0.1-0.2	487
0.2-0.3	9583
0.3-0.4	18399
0.4-0.5	10417
0.5-0.6	3355
0.6-0.7	355
0.7-0.8	29
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8901	High Similarity	NPC4834
0.8333	Intermediate Similarity	NPC247060
0.8333	Intermediate Similarity	NPC50815
0.8172	Intermediate Similarity	NPC473314
0.7959	Intermediate Similarity	NPC471083
0.7879	Intermediate Similarity	NPC474563
0.7753	Intermediate Similarity	NPC39966
0.7745	Intermediate Similarity	NPC307903
0.7745	Intermediate Similarity	NPC140251
0.77	Intermediate Similarity	NPC474583
0.77	Intermediate Similarity	NPC293299
0.77	Intermediate Similarity	NPC45365
0.7604	Intermediate Similarity	NPC280710
0.7604	Intermediate Similarity	NPC243985
0.7556	Intermediate Similarity	NPC224072
0.7551	Intermediate Similarity	NPC240650
0.7549	Intermediate Similarity	NPC55462
0.75	Intermediate Similarity	NPC77703
0.7447	Intermediate Similarity	NPC316186
0.7447	Intermediate Similarity	NPC324405
0.7429	Intermediate Similarity	NPC122926
0.7429	Intermediate Similarity	NPC113012
0.7429	Intermediate Similarity	NPC476290
0.7353	Intermediate Similarity	NPC90538
0.7349	Intermediate Similarity	NPC114651
0.7308	Intermediate Similarity	NPC25340
0.7308	Intermediate Similarity	NPC169375
0.7308	Intermediate Similarity	NPC475800
0.7294	Intermediate Similarity	NPC34834
0.729	Intermediate Similarity	NPC476269
0.7264	Intermediate Similarity	NPC472359
0.7234	Intermediate Similarity	NPC166458
0.72	Intermediate Similarity	NPC140300
0.7176	Intermediate Similarity	NPC471560
0.717	Intermediate Similarity	NPC474725
0.713	Intermediate Similarity	NPC56796
0.7103	Intermediate Similarity	NPC328052
0.7033	Intermediate Similarity	NPC47982
0.7033	Intermediate Similarity	NPC109546
0.7033	Intermediate Similarity	NPC84694
0.7033	Intermediate Similarity	NPC143182
0.7033	Intermediate Similarity	NPC81306
0.7033	Intermediate Similarity	NPC28862
0.7027	Intermediate Similarity	NPC476190
0.7024	Intermediate Similarity	NPC202017
0.7	Intermediate Similarity	NPC91594
0.6977	Remote Similarity	NPC474248
0.6957	Remote Similarity	NPC234193
0.6947	Remote Similarity	NPC75810
0.6923	Remote Similarity	NPC167891
0.6923	Remote Similarity	NPC474216
0.6923	Remote Similarity	NPC469598
0.6923	Remote Similarity	NPC83351
0.6893	Remote Similarity	NPC275686
0.6889	Remote Similarity	NPC247325
0.6889	Remote Similarity	NPC265588
0.6889	Remote Similarity	NPC244488
0.6882	Remote Similarity	NPC23852
0.6882	Remote Similarity	NPC209620
0.6882	Remote Similarity	NPC264245
0.6882	Remote Similarity	NPC475724
0.6863	Remote Similarity	NPC474164
0.686	Remote Similarity	NPC208999
0.686	Remote Similarity	NPC96484
0.6848	Remote Similarity	NPC209430
0.6848	Remote Similarity	NPC30986
0.6832	Remote Similarity	NPC311164
0.6832	Remote Similarity	NPC272732
0.6818	Remote Similarity	NPC477792
0.6818	Remote Similarity	NPC80834
0.6818	Remote Similarity	NPC469968
0.6809	Remote Similarity	NPC101462
0.6809	Remote Similarity	NPC50964
0.6809	Remote Similarity	NPC49964
0.6809	Remote Similarity	NPC189972
0.68	Remote Similarity	NPC93027
0.6796	Remote Similarity	NPC91604
0.6786	Remote Similarity	NPC107540
0.6786	Remote Similarity	NPC290367
0.6782	Remote Similarity	NPC473893
0.6774	Remote Similarity	NPC209944
0.6774	Remote Similarity	NPC241290
0.6774	Remote Similarity	NPC164840
0.6768	Remote Similarity	NPC84171
0.6765	Remote Similarity	NPC476903
0.6762	Remote Similarity	NPC176012
0.6744	Remote Similarity	NPC68703
0.6744	Remote Similarity	NPC69649
0.6744	Remote Similarity	NPC171225
0.6742	Remote Similarity	NPC474140
0.6742	Remote Similarity	NPC265485
0.6742	Remote Similarity	NPC471799
0.6742	Remote Similarity	NPC130665
0.6742	Remote Similarity	NPC220939
0.6739	Remote Similarity	NPC476314
0.6739	Remote Similarity	NPC473943
0.6737	Remote Similarity	NPC475789
0.6737	Remote Similarity	NPC470384
0.6737	Remote Similarity	NPC474634
0.6737	Remote Similarity	NPC317458
0.6705	Remote Similarity	NPC92801
0.6703	Remote Similarity	NPC321016
0.6703	Remote Similarity	NPC321381
0.6703	Remote Similarity	NPC96319
0.6703	Remote Similarity	NPC253190
0.6703	Remote Similarity	NPC107059
0.6702	Remote Similarity	NPC474752
0.6702	Remote Similarity	NPC476646
0.6702	Remote Similarity	NPC474731
0.6702	Remote Similarity	NPC47761
0.6702	Remote Similarity	NPC474759
0.6702	Remote Similarity	NPC82986
0.6702	Remote Similarity	NPC474683
0.6702	Remote Similarity	NPC7505
0.6667	Remote Similarity	NPC238485
0.6667	Remote Similarity	NPC205845
0.6667	Remote Similarity	NPC306727
0.6667	Remote Similarity	NPC477199
0.6667	Remote Similarity	NPC476366
0.6667	Remote Similarity	NPC471797
0.6667	Remote Similarity	NPC471238
0.6667	Remote Similarity	NPC185568
0.6667	Remote Similarity	NPC201048
0.6638	Remote Similarity	NPC242692
0.6636	Remote Similarity	NPC119329
0.6633	Remote Similarity	NPC312561
0.6632	Remote Similarity	NPC202389
0.6632	Remote Similarity	NPC87489
0.663	Remote Similarity	NPC470758
0.663	Remote Similarity	NPC477425
0.663	Remote Similarity	NPC155986
0.663	Remote Similarity	NPC198968
0.663	Remote Similarity	NPC477426
0.663	Remote Similarity	NPC470711
0.663	Remote Similarity	NPC318495
0.663	Remote Similarity	NPC477427
0.663	Remote Similarity	NPC474826
0.6629	Remote Similarity	NPC242001
0.6629	Remote Similarity	NPC23954
0.6628	Remote Similarity	NPC326310
0.6628	Remote Similarity	NPC267027
0.6627	Remote Similarity	NPC66020
0.6598	Remote Similarity	NPC274448
0.6598	Remote Similarity	NPC179006
0.6598	Remote Similarity	NPC474853
0.6598	Remote Similarity	NPC266511
0.6596	Remote Similarity	NPC295131
0.6596	Remote Similarity	NPC96362
0.6593	Remote Similarity	NPC136188
0.6593	Remote Similarity	NPC69383
0.6593	Remote Similarity	NPC313185
0.6593	Remote Similarity	NPC230301
0.6593	Remote Similarity	NPC28657
0.6593	Remote Similarity	NPC32832
0.6593	Remote Similarity	NPC285893
0.6593	Remote Similarity	NPC22105
0.6593	Remote Similarity	NPC304309
0.6593	Remote Similarity	NPC134847
0.6593	Remote Similarity	NPC288035
0.6593	Remote Similarity	NPC171148
0.6593	Remote Similarity	NPC162742
0.6593	Remote Similarity	NPC313179
0.6591	Remote Similarity	NPC103712
0.6591	Remote Similarity	NPC291196
0.6588	Remote Similarity	NPC96793
0.6588	Remote Similarity	NPC323424
0.6588	Remote Similarity	NPC309300
0.6583	Remote Similarity	NPC472414
0.6581	Remote Similarity	NPC472458
0.6581	Remote Similarity	NPC469943
0.6574	Remote Similarity	NPC258130
0.6571	Remote Similarity	NPC135799
0.6562	Remote Similarity	NPC472377
0.6559	Remote Similarity	NPC275910
0.6559	Remote Similarity	NPC11908
0.6559	Remote Similarity	NPC475994
0.6559	Remote Similarity	NPC87604
0.6559	Remote Similarity	NPC477514
0.6559	Remote Similarity	NPC477522
0.6556	Remote Similarity	NPC474743
0.6555	Remote Similarity	NPC472415
0.6552	Remote Similarity	NPC477791
0.6548	Remote Similarity	NPC29468
0.6538	Remote Similarity	NPC167419
0.6531	Remote Similarity	NPC293287
0.6531	Remote Similarity	NPC6391
0.6531	Remote Similarity	NPC152808
0.6531	Remote Similarity	NPC261266
0.6522	Remote Similarity	NPC240604
0.6522	Remote Similarity	NPC470749
0.6522	Remote Similarity	NPC300324
0.6522	Remote Similarity	NPC113733
0.6517	Remote Similarity	NPC145498
0.6514	Remote Similarity	NPC46981
0.6512	Remote Similarity	NPC19569
0.6509	Remote Similarity	NPC118275
0.6506	Remote Similarity	NPC122239
0.6495	Remote Similarity	NPC231310
0.6495	Remote Similarity	NPC83702
0.6495	Remote Similarity	NPC474047

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 NPC34754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	74
0.1-0.2	368
0.2-0.3	3522
0.3-0.4	3827
0.4-0.5	1182
0.5-0.6	167
0.6-0.7	10
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
0.7071	Intermediate Similarity	NPD5771	Approved
0.6789	Remote Similarity	NPD6420	Discontinued
0.6703	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7339	Approved
0.6593	Remote Similarity	NPD6942	Approved
0.6593	Remote Similarity	NPD8264	Approved
0.6522	Remote Similarity	NPD1346	Approved
0.6475	Remote Similarity	NPD6914	Discontinued
0.6465	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4722	Approved
0.64	Remote Similarity	NPD4723	Approved
0.6353	Remote Similarity	NPD368	Approved
0.6316	Remote Similarity	NPD6929	Approved
0.6304	Remote Similarity	NPD6926	Approved
0.6304	Remote Similarity	NPD6924	Approved
0.6289	Remote Similarity	NPD3667	Approved
0.6273	Remote Similarity	NPD6640	Phase 3
0.6262	Remote Similarity	NPD6404	Discontinued
0.625	Remote Similarity	NPD6931	Approved
0.625	Remote Similarity	NPD6930	Phase 2
0.6222	Remote Similarity	NPD791	Approved
0.6222	Remote Similarity	NPD15	Approved
0.622	Remote Similarity	NPD342	Phase 1
0.6211	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6933	Approved
0.6162	Remote Similarity	NPD4786	Approved
0.6146	Remote Similarity	NPD7645	Phase 2
0.6117	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6925	Approved
0.6105	Remote Similarity	NPD5776	Phase 2
0.6095	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7525	Registered
0.6082	Remote Similarity	NPD7514	Phase 3
0.6082	Remote Similarity	NPD7332	Phase 2
0.6061	Remote Similarity	NPD6695	Phase 3
0.6044	Remote Similarity	NPD1082	Approved
0.6044	Remote Similarity	NPD6923	Approved
0.6044	Remote Similarity	NPD6922	Approved
0.6042	Remote Similarity	NPD7145	Approved
0.602	Remote Similarity	NPD6902	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3133	Approved
0.5978	Remote Similarity	NPD7143	Approved
0.5978	Remote Similarity	NPD7144	Approved
0.5957	Remote Similarity	NPD4785	Approved
0.5957	Remote Similarity	NPD4784	Approved
0.5941	Remote Similarity	NPD6893	Approved
0.5918	Remote Similarity	NPD4748	Discontinued
0.5918	Remote Similarity	NPD7509	Discontinued
0.5914	Remote Similarity	NPD7150	Approved
0.5914	Remote Similarity	NPD7151	Approved
0.5914	Remote Similarity	NPD4243	Approved
0.5914	Remote Similarity	NPD7152	Approved
0.5882	Remote Similarity	NPD7505	Discontinued
0.5882	Remote Similarity	NPD3618	Phase 1
0.5862	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6898	Phase 1
0.5841	Remote Similarity	NPD7333	Discontinued
0.5841	Remote Similarity	NPD5357	Phase 1
0.5841	Remote Similarity	NPD4211	Phase 1
0.5833	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7524	Approved
0.5825	Remote Similarity	NPD7750	Discontinued
0.582	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5707	Approved
0.5784	Remote Similarity	NPD1696	Phase 3
0.5776	Remote Similarity	NPD6421	Discontinued
0.5773	Remote Similarity	NPD6932	Approved
0.5772	Remote Similarity	NPD7623	Phase 3
0.5772	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD4219	Approved
0.5739	Remote Similarity	NPD6406	Approved
0.5729	Remote Similarity	NPD4190	Phase 3
0.5729	Remote Similarity	NPD5275	Approved
0.5728	Remote Similarity	NPD4623	Approved
0.5728	Remote Similarity	NPD5279	Phase 3
0.5728	Remote Similarity	NPD4519	Discontinued
0.5714	Remote Similarity	NPD5328	Approved
0.569	Remote Similarity	NPD6413	Approved
0.5686	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD3668	Phase 3
0.5657	Remote Similarity	NPD6683	Phase 2
0.5657	Remote Similarity	NPD4195	Approved
0.5656	Remote Similarity	NPD7522	Discontinued
0.5638	Remote Similarity	NPD6939	Phase 2
0.5638	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4159	Approved
0.5607	Remote Similarity	NPD6079	Approved
0.5607	Remote Similarity	NPD7087	Discontinued

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