NPASS Compound

Structure

NPC255414 OpenBabel07101719252D 30 32 0 0 1 0 0 0 0 0999 V2000 0.8398 -1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3591 -2.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4890 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0042 -0.3549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 1.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4386 2.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0820 1.5903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5020 1.8733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5223 0.7263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9726 0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 -2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1243 1.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 -1.4545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6796 -0.9697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6796 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5193 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 0.4848 0.0000 C 0 0 2 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 -0.0000 -3.8788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 -2.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7693 -0.5903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8366 0.0406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 -2.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 -1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 18 2 0 0 0 0 14 28 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 6 0 0 0 16 25 2 0 0 0 0 16 29 1 0 0 0 0 17 26 2 0 0 0 0 17 30 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 1 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 21 23 1 1 0 0 0 23 24 1 6 0 0 0 24 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.25
Volume:	440.186
LogP:	3.868
LogD:	3.632
LogS:	-4.597
# Rotatable Bonds:	7
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	4.561
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.791
MDCK Permeability:	2.8693008061964065e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	91.03803253173828%
Volume Distribution (VD):	2.729
Pgp-substrate:	10.52977180480957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.151
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.262
CYP2C19-substrate:	0.32
CYP2C9-inhibitor:	0.666
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.904
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.786
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	6.405
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.885
Drug-inuced Liver Injury (DILI):	0.382
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.956
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.125
Carcinogencity:	0.239
Eye Corrosion:	0.008
Eye Irritation:	0.015
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: NPC255414

Natural Product ID:	NPC255414
*Common Name:**	(5S,6S,7R,8R,9R,10S)-6Beta,7Beta-Diacetoxy-15,16-Epoxylabda-13(16),14-Diene-9Alpha-Ol
IUPAC Name:	[(1S,2R,3R,4R,4aS,8aS)-1-acetyloxy-4-[2-(furan-3-yl)ethyl]-4-hydroxy-3,4a,8,8-tetramethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalen-2-yl] acetate
Synonyms:
Standard InCHIKey:	JVNDWNJCKQLUBH-WHRQKLDXSA-N
Standard InCHI:	InChI=1S/C24H36O6/c1-15-19(29-16(2)25)20(30-17(3)26)21-22(4,5)10-7-11-23(21,6)24(15,27)12-8-18-9-13-28-14-18/h9,13-15,19-21,27H,7-8,10-12H2,1-6H3/t15-,19-,20-,21+,23+,24-/m1/s1
SMILES:	C[C@@H]1[C@H]([C@H]([C@H]2C(C)(C)CCC[C@]2(C)[C@]1(CCc1ccoc1)O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234598
PubChem CID:	90670461
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24707938]
NPO17287	Lagopsis supina	Species	Lamiaceae	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
Others	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.	Inhibition	<	50.0	%	PMID[549850]

☑ 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 NPC255414 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	302
0.1-0.2	1268
0.2-0.3	2793
0.3-0.4	5096
0.4-0.5	9691
0.5-0.6	9960
0.6-0.7	10266
0.7-0.8	2754
0.8-0.85	333
0.85-0.9	205
0.9-0.95	23
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9858	High Similarity	NPC69647
0.9858	High Similarity	NPC125182
0.964	High Similarity	NPC121158
0.9574	High Similarity	NPC5676
0.9517	High Similarity	NPC268905
0.9392	High Similarity	NPC195954
0.9366	High Similarity	NPC251865
0.9357	High Similarity	NPC67003
0.9262	High Similarity	NPC194499
0.9262	High Similarity	NPC88007
0.9205	High Similarity	NPC200782
0.9133	High Similarity	NPC214495
0.9133	High Similarity	NPC475066
0.9133	High Similarity	NPC470119
0.9133	High Similarity	NPC299038
0.9128	High Similarity	NPC476262
0.9122	High Similarity	NPC472672
0.9122	High Similarity	NPC476201
0.9116	High Similarity	NPC212257
0.9079	High Similarity	NPC472771
0.9079	High Similarity	NPC68848
0.9079	High Similarity	NPC82851
0.9073	High Similarity	NPC475226
0.9073	High Similarity	NPC475967
0.9073	High Similarity	NPC472671
0.906	High Similarity	NPC237259
0.906	High Similarity	NPC98206
0.906	High Similarity	NPC253201
0.906	High Similarity	NPC34421
0.906	High Similarity	NPC282445
0.906	High Similarity	NPC302054
0.9054	High Similarity	NPC18135
0.9048	High Similarity	NPC472654
0.9028	High Similarity	NPC243577
0.9026	High Similarity	NPC472141
0.902	High Similarity	NPC472773
0.9013	High Similarity	NPC8389
0.9013	High Similarity	NPC472653
0.9007	High Similarity	NPC470118
0.8993	High Similarity	NPC469503
0.8993	High Similarity	NPC29695
0.8993	High Similarity	NPC121615
0.8993	High Similarity	NPC308205
0.8993	High Similarity	NPC322546
0.8993	High Similarity	NPC294511
0.8993	High Similarity	NPC182427
0.8986	High Similarity	NPC228842
0.8986	High Similarity	NPC476122
0.8968	High Similarity	NPC472774
0.8968	High Similarity	NPC472775
0.8961	High Similarity	NPC470182
0.8954	High Similarity	NPC188649
0.8954	High Similarity	NPC149896
0.8954	High Similarity	NPC79571
0.8954	High Similarity	NPC18347
0.8954	High Similarity	NPC470792
0.894	High Similarity	NPC41880
0.8919	High Similarity	NPC195325
0.8912	High Similarity	NPC216755
0.8912	High Similarity	NPC71821
0.8912	High Similarity	NPC471174
0.8903	High Similarity	NPC97574
0.8903	High Similarity	NPC93172
0.8896	High Similarity	NPC288602
0.8896	High Similarity	NPC134254
0.8896	High Similarity	NPC234660
0.8896	High Similarity	NPC469338
0.8896	High Similarity	NPC283209
0.8896	High Similarity	NPC292389
0.8896	High Similarity	NPC472139
0.8896	High Similarity	NPC285567
0.8896	High Similarity	NPC302369
0.8896	High Similarity	NPC39986
0.8896	High Similarity	NPC88841
0.8896	High Similarity	NPC51568
0.8889	High Similarity	NPC335761
0.8889	High Similarity	NPC470789
0.8882	High Similarity	NPC7059
0.8882	High Similarity	NPC261597
0.8882	High Similarity	NPC472776
0.8882	High Similarity	NPC249021
0.8882	High Similarity	NPC472777
0.8882	High Similarity	NPC472772
0.8882	High Similarity	NPC167142
0.8882	High Similarity	NPC472778
0.8874	High Similarity	NPC141538
0.8874	High Similarity	NPC214541
0.8874	High Similarity	NPC264943
0.8874	High Similarity	NPC296807
0.8874	High Similarity	NPC155939
0.8874	High Similarity	NPC44675
0.8874	High Similarity	NPC92979
0.8867	High Similarity	NPC33938
0.8865	High Similarity	NPC476947
0.8859	High Similarity	NPC470997
0.8846	High Similarity	NPC270312
0.8846	High Similarity	NPC173516
0.8839	High Similarity	NPC476857
0.8839	High Similarity	NPC271657
0.8839	High Similarity	NPC56358
0.8839	High Similarity	NPC470940
0.8839	High Similarity	NPC476858
0.8839	High Similarity	NPC469849
0.8839	High Similarity	NPC276551
0.8839	High Similarity	NPC476856
0.8831	High Similarity	NPC471167
0.8831	High Similarity	NPC472668
0.8831	High Similarity	NPC471166
0.8831	High Similarity	NPC18986
0.8831	High Similarity	NPC329938
0.8831	High Similarity	NPC5079
0.8816	High Similarity	NPC104736
0.8808	High Similarity	NPC30222
0.8808	High Similarity	NPC178932
0.8808	High Similarity	NPC57998
0.8803	High Similarity	NPC46896
0.8792	High Similarity	NPC470790
0.8792	High Similarity	NPC470791
0.8792	High Similarity	NPC471001
0.8792	High Similarity	NPC234494
0.8792	High Similarity	NPC211625
0.879	High Similarity	NPC160651
0.879	High Similarity	NPC471397
0.879	High Similarity	NPC296558
0.879	High Similarity	NPC271235
0.8784	High Similarity	NPC221809
0.8782	High Similarity	NPC277618
0.8782	High Similarity	NPC121995
0.8782	High Similarity	NPC307781
0.8782	High Similarity	NPC472670
0.8782	High Similarity	NPC470875
0.8774	High Similarity	NPC477405
0.8774	High Similarity	NPC471168
0.8774	High Similarity	NPC472669
0.8767	High Similarity	NPC476946
0.8766	High Similarity	NPC287559
0.8766	High Similarity	NPC25255
0.8758	High Similarity	NPC45101
0.8758	High Similarity	NPC187149
0.8758	High Similarity	NPC197137
0.8758	High Similarity	NPC304692
0.8758	High Similarity	NPC36655
0.875	High Similarity	NPC35000
0.875	High Similarity	NPC469336
0.8742	High Similarity	NPC75906
0.8734	High Similarity	NPC470995
0.8733	High Similarity	NPC477404
0.8733	High Similarity	NPC156189
0.8733	High Similarity	NPC196864
0.8726	High Similarity	NPC472651
0.8726	High Similarity	NPC476850
0.8726	High Similarity	NPC476853
0.8726	High Similarity	NPC476861
0.8725	High Similarity	NPC471007
0.8718	High Similarity	NPC476860
0.8714	High Similarity	NPC89133
0.871	High Similarity	NPC193798
0.871	High Similarity	NPC69028
0.871	High Similarity	NPC5741
0.8707	High Similarity	NPC476944
0.8701	High Similarity	NPC474611
0.8701	High Similarity	NPC475295
0.8701	High Similarity	NPC477403
0.8701	High Similarity	NPC473473
0.8701	High Similarity	NPC307383
0.8693	High Similarity	NPC107646
0.8693	High Similarity	NPC126723
0.8693	High Similarity	NPC209364
0.8675	High Similarity	NPC116717
0.8671	High Similarity	NPC472652
0.8671	High Similarity	NPC291742
0.8671	High Similarity	NPC472673
0.8667	High Similarity	NPC470998
0.8662	High Similarity	NPC308156
0.8662	High Similarity	NPC23387
0.8658	High Similarity	NPC470941
0.8654	High Similarity	NPC476197
0.8654	High Similarity	NPC469846
0.8654	High Similarity	NPC476035
0.8654	High Similarity	NPC475039
0.8654	High Similarity	NPC14499
0.8649	High Similarity	NPC41182
0.8645	High Similarity	NPC477402
0.8636	High Similarity	NPC469847
0.8636	High Similarity	NPC286722
0.8627	High Similarity	NPC471175
0.8621	High Similarity	NPC90953
0.8618	High Similarity	NPC84063
0.8618	High Similarity	NPC246164
0.8616	High Similarity	NPC82602
0.8616	High Similarity	NPC118086
0.8611	High Similarity	NPC310043
0.8609	High Similarity	NPC196846
0.8609	High Similarity	NPC469335
0.8609	High Similarity	NPC159927
0.8608	High Similarity	NPC472764
0.8608	High Similarity	NPC472282
0.8601	High Similarity	NPC158525
0.8599	High Similarity	NPC123088
0.8592	High Similarity	NPC218838

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 NPC255414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	911
0.2-0.3	1960
0.3-0.4	2576
0.4-0.5	1971
0.5-0.6	1073
0.6-0.7	366
0.7-0.8	32
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8506	High Similarity	NPD5761	Phase 2
0.8506	High Similarity	NPD5760	Phase 2
0.8373	Intermediate Similarity	NPD8434	Phase 2
0.7961	Intermediate Similarity	NPD4628	Phase 3
0.7857	Intermediate Similarity	NPD6765	Approved
0.7857	Intermediate Similarity	NPD6764	Approved
0.7674	Intermediate Similarity	NPD6784	Approved
0.7674	Intermediate Similarity	NPD6785	Approved
0.7574	Intermediate Similarity	NPD5844	Phase 1
0.7532	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.7515	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD8127	Discontinued
0.7389	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6273	Approved
0.7371	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5494	Approved
0.7349	Intermediate Similarity	NPD7075	Discontinued
0.7341	Intermediate Similarity	NPD6559	Discontinued
0.7329	Intermediate Similarity	NPD920	Approved
0.7325	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD919	Approved
0.7289	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6799	Approved
0.724	Intermediate Similarity	NPD8404	Phase 2
0.7239	Intermediate Similarity	NPD7458	Discontinued
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6355	Discontinued
0.7205	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2532	Approved
0.7205	Intermediate Similarity	NPD2533	Approved
0.7205	Intermediate Similarity	NPD2534	Approved
0.7188	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4110	Phase 3
0.7169	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1608	Approved
0.716	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD3749	Approved
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD1551	Phase 2
0.7134	Intermediate Similarity	NPD6100	Approved
0.7126	Intermediate Similarity	NPD3817	Phase 2
0.7118	Intermediate Similarity	NPD1247	Approved
0.7108	Intermediate Similarity	NPD1934	Approved
0.7108	Intermediate Similarity	NPD37	Approved
0.7108	Intermediate Similarity	NPD6801	Discontinued
0.7083	Intermediate Similarity	NPD3882	Suspended
0.7083	Intermediate Similarity	NPD4967	Phase 2
0.7083	Intermediate Similarity	NPD4965	Approved
0.7083	Intermediate Similarity	NPD4966	Approved
0.7081	Intermediate Similarity	NPD7236	Approved
0.7076	Intermediate Similarity	NPD6232	Discontinued
0.707	Intermediate Similarity	NPD2799	Discontinued
0.7063	Intermediate Similarity	NPD3750	Approved
0.7059	Intermediate Similarity	NPD7497	Discontinued
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7044	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3226	Approved
0.703	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2935	Discontinued
0.7025	Intermediate Similarity	NPD2796	Approved
0.7024	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7199	Phase 2
0.7012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD1243	Approved
0.7	Intermediate Similarity	NPD6234	Discontinued
0.6994	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4380	Phase 2
0.6982	Remote Similarity	NPD7768	Phase 2
0.6981	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2346	Discontinued
0.6981	Remote Similarity	NPD1471	Phase 3
0.6981	Remote Similarity	NPD6002	Phase 3
0.6981	Remote Similarity	NPD5762	Approved
0.6981	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5763	Approved
0.6981	Remote Similarity	NPD6004	Phase 3
0.6981	Remote Similarity	NPD6005	Phase 3
0.6978	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7229	Phase 3
0.6964	Remote Similarity	NPD2801	Approved
0.6962	Remote Similarity	NPD7033	Discontinued
0.6962	Remote Similarity	NPD3748	Approved
0.6959	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD7003	Approved
0.6941	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1549	Phase 2
0.6936	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5402	Approved
0.6914	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3764	Approved
0.6894	Remote Similarity	NPD2800	Approved
0.6883	Remote Similarity	NPD6832	Phase 2
0.6875	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2344	Approved
0.6875	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8313	Approved
0.6872	Remote Similarity	NPD8312	Approved
0.6867	Remote Similarity	NPD7239	Suspended
0.6864	Remote Similarity	NPD1465	Phase 2
0.6859	Remote Similarity	NPD6233	Phase 2
0.6859	Remote Similarity	NPD8032	Phase 2
0.6855	Remote Similarity	NPD4308	Phase 3
0.6854	Remote Similarity	NPD7685	Pre-registration
0.6846	Remote Similarity	NPD1778	Approved
0.6839	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3926	Phase 2
0.6839	Remote Similarity	NPD7095	Approved
0.6836	Remote Similarity	NPD7074	Phase 3
0.6833	Remote Similarity	NPD8407	Phase 2
0.6821	Remote Similarity	NPD3972	Approved
0.6821	Remote Similarity	NPD6959	Discontinued
0.6818	Remote Similarity	NPD7799	Discontinued
0.6818	Remote Similarity	NPD7228	Approved
0.6815	Remote Similarity	NPD4140	Approved
0.6813	Remote Similarity	NPD2438	Suspended
0.681	Remote Similarity	NPD3887	Approved
0.681	Remote Similarity	NPD6190	Approved
0.6807	Remote Similarity	NPD5403	Approved
0.68	Remote Similarity	NPD6166	Phase 2
0.68	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2797	Approved
0.6795	Remote Similarity	NPD3268	Approved
0.6795	Remote Similarity	NPD6798	Discontinued
0.6795	Remote Similarity	NPD2313	Discontinued
0.6792	Remote Similarity	NPD7097	Phase 1
0.6788	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5401	Approved
0.678	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7054	Approved
0.6776	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD447	Suspended
0.6772	Remote Similarity	NPD230	Phase 1
0.6765	Remote Similarity	NPD8455	Phase 2
0.676	Remote Similarity	NPD8368	Discontinued
0.6758	Remote Similarity	NPD8150	Discontinued
0.6753	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1510	Phase 2
0.6748	Remote Similarity	NPD8166	Discontinued
0.6746	Remote Similarity	NPD6386	Approved
0.6746	Remote Similarity	NPD6385	Approved
0.6742	Remote Similarity	NPD7472	Approved
0.6732	Remote Similarity	NPD1283	Approved
0.673	Remote Similarity	NPD6653	Approved
0.673	Remote Similarity	NPD1607	Approved
0.6727	Remote Similarity	NPD1511	Approved
0.6725	Remote Similarity	NPD5353	Approved
0.6723	Remote Similarity	NPD3751	Discontinued
0.6723	Remote Similarity	NPD7177	Discontinued
0.6722	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4107	Approved
0.6711	Remote Similarity	NPD9545	Approved
0.6709	Remote Similarity	NPD1240	Approved
0.6709	Remote Similarity	NPD4307	Phase 2
0.6709	Remote Similarity	NPD4060	Phase 1
0.6709	Remote Similarity	NPD2979	Phase 3
0.6707	Remote Similarity	NPD2309	Approved
0.6707	Remote Similarity	NPD2354	Approved
0.6686	Remote Similarity	NPD3787	Discontinued
0.6686	Remote Similarity	NPD5711	Approved
0.6686	Remote Similarity	NPD5710	Approved
0.6686	Remote Similarity	NPD7028	Phase 2
0.6686	Remote Similarity	NPD7315	Approved
0.6685	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD7240	Approved
0.6667	Remote Similarity	NPD7251	Discontinued
0.6648	Remote Similarity	NPD5242	Approved
0.6647	Remote Similarity	NPD1512	Approved
0.6647	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7808	Phase 3
0.6628	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4534	Discontinued
0.6623	Remote Similarity	NPD6696	Suspended
0.6615	Remote Similarity	NPD7435	Discontinued
0.6611	Remote Similarity	NPD6797	Phase 2
0.661	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4477	Approved
0.6605	Remote Similarity	NPD4476	Approved
0.6603	Remote Similarity	NPD9494	Approved
0.6601	Remote Similarity	NPD9717	Approved
0.6597	Remote Similarity	NPD4482	Phase 3
0.6592	Remote Similarity	NPD7286	Phase 2
0.6591	Remote Similarity	NPD6808	Phase 2
0.6582	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1203	Approved
0.6581	Remote Similarity	NPD3267	Approved
0.6581	Remote Similarity	NPD3266	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