NPASS Compound

Structure

NPC294511 OpenBabel07101719512D 26 29 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 0.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 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 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -3.5491 -0.1910 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 13 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 1 1 1 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 23 2 0 0 0 0 13 26 1 0 0 0 0 14 16 2 0 0 0 0 15 17 1 0 0 0 0 15 22 1 6 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	382.094
LogP:	4.504
LogD:	4.538
LogS:	-4.476
# Rotatable Bonds:	2
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	4.641
Fsp3:	0.773
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:	-4.682
MDCK Permeability:	2.2709638869855553e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.071
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.252
30% Bioavailability (F30%):	0.867

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	96.11540985107422%
Volume Distribution (VD):	2.708
Pgp-substrate:	5.093292236328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.428
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.286
CYP2C19-substrate:	0.625
CYP2C9-inhibitor:	0.566
CYP2C9-substrate:	0.21
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	5.324
Half-life (T1/2):	0.315

ADMET: Toxicity

hERG Blockers:	0.599
Human Hepatotoxicity (H-HT):	0.753
Drug-inuced Liver Injury (DILI):	0.833
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.589
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.227
Carcinogencity:	0.079
Eye Corrosion:	0.011
Eye Irritation:	0.016
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: NPC294511

Natural Product ID:	NPC294511
*Common Name:**	Sucutinirane E
IUPAC Name:	[(4aS,5R,6R,6aS,7R,11aS,11bR)-6-hydroxy-4,4,7,11b-tetramethyl-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-5-yl] acetate
Synonyms:	Sucutinirane E
Standard InCHIKey:	YFPBRZZBJVPWPJ-QMXKAFJASA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-12-14-7-10-25-16(14)11-15-17(12)18(24)19(26-13(2)23)20-21(3,4)8-6-9-22(15,20)5/h7,10,12,15,17-20,24H,6,8-9,11H2,1-5H3/t12-,15-,17-,18+,19-,20-,22+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H](O)[C@H]2[C@@H](C)c3ccoc3C[C@@H]2[C@@]2([C@@H]1C(C)(C)CCC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557897
PubChem CID:	44130070
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO28335	Bowdichia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524584]
NPO28335	Bowdichia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19361174]
NPO28335	Bowdichia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO28335	Bowdichia nitida	Species	Fabaceae	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	12000.0	nM	PMID[503863]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	35000.0	nM	PMID[503863]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	36000.0	nM	PMID[503863]

☑ 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 NPC294511 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	312
0.1-0.2	1243
0.2-0.3	2545
0.3-0.4	5027
0.4-0.5	9918
0.5-0.6	8938
0.6-0.7	8353
0.7-0.8	5829
0.8-0.85	359
0.85-0.9	120
0.9-0.95	40
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC121615
0.973	High Similarity	NPC194499
0.9724	High Similarity	NPC228842
0.9653	High Similarity	NPC71821
0.9597	High Similarity	NPC88007
0.9597	High Similarity	NPC7059
0.9536	High Similarity	NPC79571
0.947	High Similarity	NPC8389
0.9467	High Similarity	NPC195954
0.9456	High Similarity	NPC212257
0.9408	High Similarity	NPC68848
0.9408	High Similarity	NPC18986
0.9346	High Similarity	NPC283209
0.9342	High Similarity	NPC287559
0.9281	High Similarity	NPC188649
0.9226	High Similarity	NPC121995
0.9226	High Similarity	NPC277618
0.9221	High Similarity	NPC288602
0.9221	High Similarity	NPC88841
0.9221	High Similarity	NPC285567
0.9172	High Similarity	NPC263337
0.915	High Similarity	NPC84349
0.915	High Similarity	NPC474611
0.9145	High Similarity	NPC41880
0.9128	High Similarity	NPC69647
0.9128	High Similarity	NPC125182
0.9122	High Similarity	NPC216755
0.9108	High Similarity	NPC296558
0.9097	High Similarity	NPC202260
0.9085	High Similarity	NPC304692
0.9079	High Similarity	NPC296807
0.9079	High Similarity	NPC141538
0.9079	High Similarity	NPC155939
0.902	High Similarity	NPC104736
0.9	High Similarity	NPC234494
0.8993	High Similarity	NPC255414
0.8993	High Similarity	NPC471174
0.8981	High Similarity	NPC475779
0.8954	High Similarity	NPC92979
0.8947	High Similarity	NPC246164
0.8931	High Similarity	NPC118086
0.8924	High Similarity	NPC310572
0.8924	High Similarity	NPC41689
0.8924	High Similarity	NPC270312
0.8917	High Similarity	NPC56358
0.8912	High Similarity	NPC121158
0.891	High Similarity	NPC471003
0.8903	High Similarity	NPC140952
0.8889	High Similarity	NPC253201
0.8889	High Similarity	NPC237259
0.8889	High Similarity	NPC302054
0.8889	High Similarity	NPC34421
0.8889	High Similarity	NPC98206
0.8875	High Similarity	NPC475237
0.8875	High Similarity	NPC475641
0.8868	High Similarity	NPC255787
0.8859	High Similarity	NPC5676
0.8846	High Similarity	NPC472299
0.8839	High Similarity	NPC81405
0.8828	High Similarity	NPC307401
0.8824	High Similarity	NPC472672
0.8824	High Similarity	NPC33938
0.8816	High Similarity	NPC196846
0.8816	High Similarity	NPC470997
0.8808	High Similarity	NPC471007
0.879	High Similarity	NPC470792
0.8776	High Similarity	NPC148374
0.8776	High Similarity	NPC67003
0.875	High Similarity	NPC211625
0.875	High Similarity	NPC291742
0.875	High Similarity	NPC471001
0.8742	High Similarity	NPC308156
0.8734	High Similarity	NPC14499
0.8734	High Similarity	NPC472773
0.8734	High Similarity	NPC476035
0.8734	High Similarity	NPC475039
0.872	High Similarity	NPC11062
0.8718	High Similarity	NPC472777
0.8718	High Similarity	NPC197137
0.8718	High Similarity	NPC472778
0.8718	High Similarity	NPC472776
0.8701	High Similarity	NPC470996
0.8701	High Similarity	NPC268905
0.869	High Similarity	NPC476947
0.8681	High Similarity	NPC293253
0.8679	High Similarity	NPC276551
0.8679	High Similarity	NPC61967
0.8679	High Similarity	NPC27541
0.8679	High Similarity	NPC62692
0.8679	High Similarity	NPC126984
0.8671	High Similarity	NPC472771
0.8671	High Similarity	NPC69028
0.8671	High Similarity	NPC200782
0.8667	High Similarity	NPC251865
0.8662	High Similarity	NPC475967
0.8662	High Similarity	NPC307383
0.8662	High Similarity	NPC472671
0.8662	High Similarity	NPC123153
0.8645	High Similarity	NPC114880
0.8645	High Similarity	NPC178932
0.8642	High Similarity	NPC294512
0.8627	High Similarity	NPC472654
0.8625	High Similarity	NPC470875
0.8618	High Similarity	NPC302987
0.8618	High Similarity	NPC286038
0.8616	High Similarity	NPC292389
0.8616	High Similarity	NPC477405
0.8616	High Similarity	NPC469338
0.8608	High Similarity	NPC335761
0.86	High Similarity	NPC243577
0.8599	High Similarity	NPC214495
0.8599	High Similarity	NPC299038
0.8599	High Similarity	NPC475066
0.8599	High Similarity	NPC470119
0.859	High Similarity	NPC75310
0.859	High Similarity	NPC264943
0.859	High Similarity	NPC35000
0.859	High Similarity	NPC469336
0.8581	High Similarity	NPC469503
0.8581	High Similarity	NPC48671
0.858	High Similarity	NPC470995
0.8571	High Similarity	NPC472282
0.8571	High Similarity	NPC170604
0.8571	High Similarity	NPC472774
0.8571	High Similarity	NPC472775
0.8571	High Similarity	NPC215109
0.8562	High Similarity	NPC66991
0.8562	High Similarity	NPC470940
0.8562	High Similarity	NPC261184
0.8562	High Similarity	NPC93666
0.8562	High Similarity	NPC469849
0.8553	High Similarity	NPC82851
0.8553	High Similarity	NPC470999
0.8553	High Similarity	NPC5079
0.8553	High Similarity	NPC263432
0.8553	High Similarity	NPC207978
0.8553	High Similarity	NPC62799
0.8553	High Similarity	NPC233763
0.8553	High Similarity	NPC329938
0.8552	High Similarity	NPC218838
0.8544	High Similarity	NPC475226
0.8544	High Similarity	NPC472823
0.8542	High Similarity	NPC89133
0.8526	High Similarity	NPC30222
0.8526	High Similarity	NPC44606
0.8523	High Similarity	NPC56197
0.8519	High Similarity	NPC471397
0.8519	High Similarity	NPC160651
0.8519	High Similarity	NPC271235
0.8516	High Similarity	NPC140133
0.8516	High Similarity	NPC272590
0.8509	High Similarity	NPC93172
0.8509	High Similarity	NPC86800
0.8509	High Similarity	NPC97574
0.8506	High Similarity	NPC195325
0.8506	High Similarity	NPC470998
0.8503	High Similarity	NPC46896
0.85	High Similarity	NPC51568
0.85	High Similarity	NPC302369
0.85	High Similarity	NPC234660
0.85	High Similarity	NPC39986
0.85	High Similarity	NPC134254
0.8491	Intermediate Similarity	NPC470789
0.8491	Intermediate Similarity	NPC477402
0.8491	Intermediate Similarity	NPC472653
0.8487	Intermediate Similarity	NPC41182
0.8487	Intermediate Similarity	NPC34056
0.8485	Intermediate Similarity	NPC176413
0.8485	Intermediate Similarity	NPC56953
0.8481	Intermediate Similarity	NPC472772
0.8481	Intermediate Similarity	NPC45101
0.8481	Intermediate Similarity	NPC470118
0.8471	Intermediate Similarity	NPC25351
0.8471	Intermediate Similarity	NPC214541
0.8471	Intermediate Similarity	NPC44675
0.8466	Intermediate Similarity	NPC88593
0.8466	Intermediate Similarity	NPC302392
0.8462	Intermediate Similarity	NPC471002
0.8462	Intermediate Similarity	NPC475777
0.8462	Intermediate Similarity	NPC476201
0.8457	Intermediate Similarity	NPC173516
0.8457	Intermediate Similarity	NPC472651
0.8457	Intermediate Similarity	NPC473766
0.8457	Intermediate Similarity	NPC473753
0.8447	Intermediate Similarity	NPC476856
0.8447	Intermediate Similarity	NPC276735
0.8447	Intermediate Similarity	NPC470182
0.8447	Intermediate Similarity	NPC476857
0.8447	Intermediate Similarity	NPC476858
0.8447	Intermediate Similarity	NPC472664
0.8446	Intermediate Similarity	NPC310043
0.8446	Intermediate Similarity	NPC4764
0.8442	Intermediate Similarity	NPC19747
0.8438	Intermediate Similarity	NPC211777
0.8434	Intermediate Similarity	NPC472665
0.8421	Intermediate Similarity	NPC476944
0.8418	Intermediate Similarity	NPC107646
0.8411	Intermediate Similarity	NPC52412
0.8408	Intermediate Similarity	NPC282445
0.8408	Intermediate Similarity	NPC10429

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 NPC294511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	808
0.2-0.3	1515
0.3-0.4	2512
0.4-0.5	2188
0.5-0.6	1229
0.6-0.7	502
0.7-0.8	103
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8563	High Similarity	NPD8434	Phase 2
0.8533	High Similarity	NPD4628	Phase 3
0.8263	Intermediate Similarity	NPD6765	Approved
0.8263	Intermediate Similarity	NPD6764	Approved
0.8239	Intermediate Similarity	NPD5760	Phase 2
0.8239	Intermediate Similarity	NPD5761	Phase 2
0.807	Intermediate Similarity	NPD6784	Approved
0.807	Intermediate Similarity	NPD6785	Approved
0.8025	Intermediate Similarity	NPD6273	Approved
0.7987	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD8127	Discontinued
0.7901	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7458	Discontinued
0.7857	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6599	Discontinued
0.7818	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7765	Intermediate Similarity	NPD5844	Phase 1
0.7758	Intermediate Similarity	NPD7075	Discontinued
0.7733	Intermediate Similarity	NPD6559	Discontinued
0.7647	Intermediate Similarity	NPD6355	Discontinued
0.7622	Intermediate Similarity	NPD6801	Discontinued
0.759	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6799	Approved
0.7557	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3226	Approved
0.7546	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5762	Approved
0.7516	Intermediate Similarity	NPD8032	Phase 2
0.7516	Intermediate Similarity	NPD5763	Approved
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD7236	Approved
0.7484	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4110	Phase 3
0.7484	Intermediate Similarity	NPD8166	Discontinued
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7003	Approved
0.747	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4140	Approved
0.7456	Intermediate Similarity	NPD5494	Approved
0.7455	Intermediate Similarity	NPD7411	Suspended
0.7451	Intermediate Similarity	NPD6798	Discontinued
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.7442	Intermediate Similarity	NPD7473	Discontinued
0.744	Intermediate Similarity	NPD3749	Approved
0.7425	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3817	Phase 2
0.7423	Intermediate Similarity	NPD920	Approved
0.7423	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD37	Approved
0.741	Intermediate Similarity	NPD1934	Approved
0.7409	Intermediate Similarity	NPD8404	Phase 2
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.7405	Intermediate Similarity	NPD1471	Phase 3
0.7399	Intermediate Similarity	NPD3818	Discontinued
0.7394	Intermediate Similarity	NPD4380	Phase 2
0.7391	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7095	Approved
0.7386	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD3882	Suspended
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7375	Intermediate Similarity	NPD3750	Approved
0.7342	Intermediate Similarity	NPD6099	Approved
0.7342	Intermediate Similarity	NPD6100	Approved
0.7342	Intermediate Similarity	NPD2796	Approved
0.7338	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3764	Approved
0.7337	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5403	Approved
0.7308	Intermediate Similarity	NPD5735	Approved
0.7301	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5401	Approved
0.7299	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD17	Approved
0.7296	Intermediate Similarity	NPD2344	Approved
0.7294	Intermediate Similarity	NPD6234	Discontinued
0.7283	Intermediate Similarity	NPD6166	Phase 2
0.7283	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD3748	Approved
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD7239	Suspended
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD6232	Discontinued
0.7262	Intermediate Similarity	NPD8455	Phase 2
0.7253	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1549	Phase 2
0.7238	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1551	Phase 2
0.7226	Intermediate Similarity	NPD2313	Discontinued
0.7226	Intermediate Similarity	NPD3268	Approved
0.7219	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5402	Approved
0.7216	Intermediate Similarity	NPD7074	Phase 3
0.7205	Intermediate Similarity	NPD1243	Approved
0.72	Intermediate Similarity	NPD7799	Discontinued
0.72	Intermediate Similarity	NPD7228	Approved
0.72	Intermediate Similarity	NPD7177	Discontinued
0.7195	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2532	Approved
0.7195	Intermediate Similarity	NPD2534	Approved
0.7195	Intermediate Similarity	NPD2533	Approved
0.7188	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6005	Phase 3
0.7188	Intermediate Similarity	NPD6004	Phase 3
0.7188	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6002	Phase 3
0.7184	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3057	Approved
0.7181	Intermediate Similarity	NPD1778	Approved
0.7179	Intermediate Similarity	NPD6233	Phase 2
0.7168	Intermediate Similarity	NPD7229	Phase 3
0.7166	Intermediate Similarity	NPD4107	Approved
0.716	Intermediate Similarity	NPD2801	Approved
0.7159	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7497	Discontinued
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6677	Suspended
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7124	Intermediate Similarity	NPD2797	Approved
0.7119	Intermediate Similarity	NPD7472	Approved
0.7117	Intermediate Similarity	NPD3887	Approved
0.7117	Intermediate Similarity	NPD2309	Approved
0.7117	Intermediate Similarity	NPD2354	Approved
0.711	Intermediate Similarity	NPD1247	Approved
0.711	Intermediate Similarity	NPD6959	Discontinued
0.7107	Intermediate Similarity	NPD7097	Phase 1
0.7097	Intermediate Similarity	NPD6832	Phase 2
0.7091	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3533	Approved
0.709	Intermediate Similarity	NPD2972	Approved
0.7083	Intermediate Similarity	NPD7028	Phase 2
0.7078	Intermediate Similarity	NPD5647	Approved
0.7078	Intermediate Similarity	NPD2798	Approved
0.707	Intermediate Similarity	NPD6663	Approved
0.7063	Intermediate Similarity	NPD1510	Phase 2
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7059	Intermediate Similarity	NPD8651	Approved
0.7059	Intermediate Similarity	NPD1465	Phase 2
0.7059	Intermediate Similarity	NPD1283	Approved
0.7047	Intermediate Similarity	NPD9545	Approved
0.7044	Intermediate Similarity	NPD6653	Approved
0.7039	Intermediate Similarity	NPD7251	Discontinued
0.7039	Intermediate Similarity	NPD7240	Approved
0.7037	Intermediate Similarity	NPD4534	Discontinued
0.7037	Intermediate Similarity	NPD4482	Phase 3
0.7032	Intermediate Similarity	NPD5736	Approved
0.7032	Intermediate Similarity	NPD9494	Approved
0.703	Intermediate Similarity	NPD1511	Approved
0.7029	Intermediate Similarity	NPD3926	Phase 2
0.7019	Intermediate Similarity	NPD2438	Suspended
0.7019	Intermediate Similarity	NPD2935	Discontinued
0.7017	Intermediate Similarity	NPD8407	Phase 2
0.7013	Intermediate Similarity	NPD3266	Approved
0.7013	Intermediate Similarity	NPD3267	Approved
0.7012	Intermediate Similarity	NPD6190	Approved
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7006	Intermediate Similarity	NPD2163	Approved
0.7	Intermediate Similarity	NPD2491	Approved
0.7	Intermediate Similarity	NPD7808	Phase 3
0.7	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2800	Approved
0.6993	Remote Similarity	NPD5327	Phase 3
0.6983	Remote Similarity	NPD6797	Phase 2
0.6974	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3787	Discontinued
0.6968	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4062	Phase 3
0.6959	Remote Similarity	NPD7157	Approved
0.6954	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1876	Approved
0.6946	Remote Similarity	NPD1512	Approved
0.6946	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5049	Phase 3
0.6944	Remote Similarity	NPD8368	Discontinued
0.6944	Remote Similarity	NPD7038	Approved
0.6944	Remote Similarity	NPD7039	Approved
0.6941	Remote Similarity	NPD6385	Approved
0.6941	Remote Similarity	NPD6386	Approved
0.6937	Remote Similarity	NPD1607	Approved
0.6933	Remote Similarity	NPD5958	Discontinued
0.6923	Remote Similarity	NPD2649	Approved
0.6923	Remote Similarity	NPD2651	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