NPASS Compound

Structure

NPC69647 OpenBabel07101719512D 27 29 0 0 1 0 0 0 0 0999 V2000 -0.8372 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4781 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9948 0.3538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -1.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4341 -2.1176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0724 -1.5853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5004 -1.8675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5113 -0.7240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9664 -0.4793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5115 2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1176 -1.4341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 1.4500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6743 0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6743 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5115 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -0.4833 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 1.6743 2.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 2.4167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7669 0.5885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8277 -0.0405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 1.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 13 16 2 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 6 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 21 1 1 0 0 0 21 22 1 6 0 0 0 22 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	399.441
LogP:	3.652
LogD:	3.613
LogS:	-4.42
# Rotatable Bonds:	5
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.781
Synthetic Accessibility Score:	4.591
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.719
MDCK Permeability:	2.9672453820239753e-05
Pgp-inhibitor:	0.774
Pgp-substrate:	0.138
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.382

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	93.35021209716797%
Volume Distribution (VD):	2.271
Pgp-substrate:	8.672378540039062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.643
CYP2C9-inhibitor:	0.59
CYP2C9-substrate:	0.289
CYP2D6-inhibitor:	0.095
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.656
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	8.341
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.464
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.118
Carcinogencity:	0.497
Eye Corrosion:	0.006
Eye Irritation:	0.019
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: NPC69647

Natural Product ID:	NPC69647
*Common Name:**	(5S,6S,7R,8R,9R,10S)-6Beta-Acetoxy-15,16-Epoxylabda-13(16),14-Diene-7Beta,9Alpha-Diol
IUPAC Name:	[(1S,2R,3R,4R,4aS,8aS)-4-[2-(furan-3-yl)ethyl]-2,4-dihydroxy-3,4a,8,8-tetramethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
Synonyms:
Standard InCHIKey:	NVKGCFXLVZVUOR-PHCOHBDUSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-14-17(24)18(27-15(2)23)19-20(3,4)9-6-10-21(19,5)22(14,25)11-7-16-8-12-26-13-16/h8,12-14,17-19,24-25H,6-7,9-11H2,1-5H3/t14-,17-,18-,19+,21+,22-/m1/s1
SMILES:	CC(=O)O[C@@H]1[C@H](O)[C@@H](C)[C@]([C@@]2([C@@H]1C(C)(C)CCC2)C)(O)CCc1cocc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234597
PubChem CID:	90670460
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[551615]

☑ 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 NPC69647 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	304
0.1-0.2	1201
0.2-0.3	2908
0.3-0.4	4941
0.4-0.5	9506
0.5-0.6	10059
0.6-0.7	10251
0.7-0.8	2960
0.8-0.85	342
0.85-0.9	171
0.9-0.95	50
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC125182
0.9858	High Similarity	NPC255414
0.9716	High Similarity	NPC5676
0.9521	High Similarity	NPC268905
0.9504	High Similarity	NPC121158
0.9396	High Similarity	NPC194499
0.9362	High Similarity	NPC67003
0.9338	High Similarity	NPC200782
0.9267	High Similarity	NPC195954
0.9267	High Similarity	NPC88007
0.9236	High Similarity	NPC251865
0.9205	High Similarity	NPC475967
0.9205	High Similarity	NPC472671
0.9195	High Similarity	NPC253201
0.9195	High Similarity	NPC34421
0.9195	High Similarity	NPC237259
0.9195	High Similarity	NPC302054
0.9195	High Similarity	NPC98206
0.915	High Similarity	NPC472773
0.9139	High Similarity	NPC214495
0.9139	High Similarity	NPC470119
0.9139	High Similarity	NPC475066
0.9139	High Similarity	NPC299038
0.9128	High Similarity	NPC121615
0.9128	High Similarity	NPC472672
0.9128	High Similarity	NPC294511
0.9097	High Similarity	NPC472775
0.9097	High Similarity	NPC472774
0.9085	High Similarity	NPC68848
0.9085	High Similarity	NPC472771
0.9085	High Similarity	NPC470792
0.9085	High Similarity	NPC79571
0.9079	High Similarity	NPC475226
0.9054	High Similarity	NPC472654
0.9034	High Similarity	NPC243577
0.9032	High Similarity	NPC97574
0.9032	High Similarity	NPC93172
0.9032	High Similarity	NPC472141
0.9026	High Similarity	NPC283209
0.902	High Similarity	NPC8389
0.902	High Similarity	NPC470789
0.9013	High Similarity	NPC472776
0.9013	High Similarity	NPC472777
0.9013	High Similarity	NPC472778
0.9007	High Similarity	NPC141538
0.9007	High Similarity	NPC92979
0.9007	High Similarity	NPC155939
0.9007	High Similarity	NPC476947
0.9007	High Similarity	NPC476262
0.9007	High Similarity	NPC296807
0.9	High Similarity	NPC469503
0.9	High Similarity	NPC33938
0.9	High Similarity	NPC476201
0.8993	High Similarity	NPC212257
0.8993	High Similarity	NPC228842
0.8993	High Similarity	NPC470997
0.8968	High Similarity	NPC276551
0.8968	High Similarity	NPC470182
0.8968	High Similarity	NPC271657
0.8961	High Similarity	NPC82851
0.8961	High Similarity	NPC18986
0.8961	High Similarity	NPC188649
0.8961	High Similarity	NPC149896
0.8961	High Similarity	NPC18347
0.894	High Similarity	NPC282445
0.8933	High Similarity	NPC18135
0.8926	High Similarity	NPC234494
0.8926	High Similarity	NPC195325
0.8919	High Similarity	NPC216755
0.8919	High Similarity	NPC471174
0.8917	High Similarity	NPC471397
0.8917	High Similarity	NPC271235
0.891	High Similarity	NPC470875
0.891	High Similarity	NPC472670
0.891	High Similarity	NPC121995
0.891	High Similarity	NPC307781
0.8904	High Similarity	NPC476946
0.8903	High Similarity	NPC285567
0.8903	High Similarity	NPC292389
0.8903	High Similarity	NPC234660
0.8903	High Similarity	NPC39986
0.8903	High Similarity	NPC51568
0.8903	High Similarity	NPC88841
0.8903	High Similarity	NPC288602
0.8903	High Similarity	NPC302369
0.8903	High Similarity	NPC134254
0.8903	High Similarity	NPC477405
0.8903	High Similarity	NPC469338
0.8903	High Similarity	NPC472139
0.8896	High Similarity	NPC472653
0.8896	High Similarity	NPC335761
0.8889	High Similarity	NPC7059
0.8889	High Similarity	NPC261597
0.8889	High Similarity	NPC197137
0.8889	High Similarity	NPC45101
0.8889	High Similarity	NPC472772
0.8889	High Similarity	NPC470118
0.8882	High Similarity	NPC264943
0.8882	High Similarity	NPC214541
0.8882	High Similarity	NPC44675
0.8874	High Similarity	NPC182427
0.8874	High Similarity	NPC308205
0.8874	High Similarity	NPC322546
0.8874	High Similarity	NPC29695
0.8867	High Similarity	NPC476122
0.8861	High Similarity	NPC470995
0.8859	High Similarity	NPC471007
0.8854	High Similarity	NPC472651
0.8854	High Similarity	NPC173516
0.8846	High Similarity	NPC476858
0.8846	High Similarity	NPC469849
0.8846	High Similarity	NPC476856
0.8846	High Similarity	NPC470940
0.8846	High Similarity	NPC476857
0.8839	High Similarity	NPC5741
0.8839	High Similarity	NPC329938
0.8839	High Similarity	NPC69028
0.8839	High Similarity	NPC5079
0.8831	High Similarity	NPC307383
0.8824	High Similarity	NPC41880
0.8816	High Similarity	NPC57998
0.8816	High Similarity	NPC178932
0.88	High Similarity	NPC470998
0.8797	High Similarity	NPC296558
0.8797	High Similarity	NPC472652
0.8797	High Similarity	NPC160651
0.8797	High Similarity	NPC472673
0.8792	High Similarity	NPC71821
0.879	High Similarity	NPC277618
0.8774	High Similarity	NPC287559
0.8774	High Similarity	NPC477402
0.8766	High Similarity	NPC36655
0.8766	High Similarity	NPC304692
0.8766	High Similarity	NPC249021
0.8766	High Similarity	NPC167142
0.8766	High Similarity	NPC187149
0.8758	High Similarity	NPC469336
0.8758	High Similarity	NPC35000
0.875	High Similarity	NPC75906
0.8742	High Similarity	NPC196846
0.8742	High Similarity	NPC82602
0.8734	High Similarity	NPC270312
0.8734	High Similarity	NPC476853
0.8734	High Similarity	NPC476861
0.8734	High Similarity	NPC472282
0.8734	High Similarity	NPC476850
0.8732	High Similarity	NPC218838
0.8726	High Similarity	NPC56358
0.8723	High Similarity	NPC89133
0.8718	High Similarity	NPC263432
0.8718	High Similarity	NPC472668
0.8718	High Similarity	NPC207978
0.8718	High Similarity	NPC471166
0.8718	High Similarity	NPC211777
0.8718	High Similarity	NPC471167
0.8716	High Similarity	NPC476944
0.871	High Similarity	NPC474611
0.8701	High Similarity	NPC104736
0.8693	High Similarity	NPC30222
0.8681	High Similarity	NPC46896
0.8679	High Similarity	NPC472766
0.8679	High Similarity	NPC472765
0.8675	High Similarity	NPC470790
0.8675	High Similarity	NPC470791
0.8675	High Similarity	NPC471001
0.8675	High Similarity	NPC211625
0.8671	High Similarity	NPC23387
0.8667	High Similarity	NPC221809
0.8662	High Similarity	NPC472669
0.8662	High Similarity	NPC198047
0.8662	High Similarity	NPC471168
0.8658	High Similarity	NPC41182
0.8654	High Similarity	NPC25255
0.863	High Similarity	NPC90953
0.8627	High Similarity	NPC470996
0.8625	High Similarity	NPC118086
0.8618	High Similarity	NPC477404
0.8618	High Similarity	NPC156189
0.8618	High Similarity	NPC196864
0.8616	High Similarity	NPC472764
0.8616	High Similarity	NPC310572
0.8608	High Similarity	NPC259943
0.8608	High Similarity	NPC476860
0.8608	High Similarity	NPC123088
0.8599	High Similarity	NPC290400
0.8599	High Similarity	NPC96443
0.8599	High Similarity	NPC193798
0.8598	High Similarity	NPC470938
0.8592	High Similarity	NPC61788
0.859	High Similarity	NPC475295
0.859	High Similarity	NPC84349
0.859	High Similarity	NPC473473
0.859	High Similarity	NPC477403
0.8581	High Similarity	NPC126723
0.8581	High Similarity	NPC52412
0.8581	High Similarity	NPC107646
0.8581	High Similarity	NPC209364
0.8581	High Similarity	NPC469485
0.858	High Similarity	NPC471632
0.8571	High Similarity	NPC114880

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 NPC69647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	896
0.2-0.3	2007
0.3-0.4	2572
0.4-0.5	1969
0.5-0.6	1033
0.6-0.7	373
0.7-0.8	35
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8516	High Similarity	NPD5760	Phase 2
0.8516	High Similarity	NPD5761	Phase 2
0.8494	Intermediate Similarity	NPD8434	Phase 2
0.8092	Intermediate Similarity	NPD4628	Phase 3
0.787	Intermediate Similarity	NPD6764	Approved
0.787	Intermediate Similarity	NPD6765	Approved
0.7688	Intermediate Similarity	NPD6785	Approved
0.7688	Intermediate Similarity	NPD6784	Approved
0.7588	Intermediate Similarity	NPD5844	Phase 1
0.7531	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6559	Discontinued
0.744	Intermediate Similarity	NPD8127	Discontinued
0.7436	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7819	Suspended
0.7391	Intermediate Similarity	NPD6273	Approved
0.7386	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7075	Discontinued
0.7344	Intermediate Similarity	NPD8404	Phase 2
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD6799	Approved
0.7239	Intermediate Similarity	NPD920	Approved
0.7233	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6801	Discontinued
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD919	Approved
0.7186	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7199	Phase 2
0.7126	Intermediate Similarity	NPD37	Approved
0.7126	Intermediate Similarity	NPD3818	Discontinued
0.7126	Intermediate Similarity	NPD1934	Approved
0.7117	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2532	Approved
0.7117	Intermediate Similarity	NPD2534	Approved
0.7117	Intermediate Similarity	NPD2533	Approved
0.7108	Intermediate Similarity	NPD4380	Phase 2
0.7107	Intermediate Similarity	NPD5762	Approved
0.7107	Intermediate Similarity	NPD5763	Approved
0.7101	Intermediate Similarity	NPD4966	Approved
0.7101	Intermediate Similarity	NPD3882	Suspended
0.7101	Intermediate Similarity	NPD4965	Approved
0.7101	Intermediate Similarity	NPD4967	Phase 2
0.7099	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7236	Approved
0.7088	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4110	Phase 3
0.7074	Intermediate Similarity	NPD7497	Discontinued
0.7073	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7473	Discontinued
0.7067	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3749	Approved
0.7048	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6099	Approved
0.7044	Intermediate Similarity	NPD1551	Phase 2
0.7044	Intermediate Similarity	NPD6100	Approved
0.7041	Intermediate Similarity	NPD5402	Approved
0.7035	Intermediate Similarity	NPD1247	Approved
0.7018	Intermediate Similarity	NPD6234	Discontinued
0.7	Intermediate Similarity	NPD6002	Phase 3
0.7	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6005	Phase 3
0.6994	Remote Similarity	NPD6232	Discontinued
0.6983	Remote Similarity	NPD8312	Approved
0.6983	Remote Similarity	NPD8313	Approved
0.6982	Remote Similarity	NPD2801	Approved
0.6981	Remote Similarity	NPD7033	Discontinued
0.6981	Remote Similarity	NPD2799	Discontinued
0.6975	Remote Similarity	NPD3750	Approved
0.6966	Remote Similarity	NPD7685	Pre-registration
0.6964	Remote Similarity	NPD7411	Suspended
0.6957	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7074	Phase 3
0.6946	Remote Similarity	NPD3226	Approved
0.6944	Remote Similarity	NPD8407	Phase 2
0.6941	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2796	Approved
0.6937	Remote Similarity	NPD2935	Discontinued
0.6933	Remote Similarity	NPD6190	Approved
0.6932	Remote Similarity	NPD7228	Approved
0.6928	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5403	Approved
0.6914	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1243	Approved
0.6914	Remote Similarity	NPD6166	Phase 2
0.691	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5401	Approved
0.6909	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7768	Phase 2
0.6897	Remote Similarity	NPD7229	Phase 3
0.6894	Remote Similarity	NPD2346	Discontinued
0.6894	Remote Similarity	NPD1471	Phase 3
0.6893	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7054	Approved
0.6886	Remote Similarity	NPD7239	Suspended
0.6882	Remote Similarity	NPD8455	Phase 2
0.6882	Remote Similarity	NPD1465	Phase 2
0.6879	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD3748	Approved
0.6872	Remote Similarity	NPD8368	Discontinued
0.6871	Remote Similarity	NPD7003	Approved
0.6868	Remote Similarity	NPD8150	Discontinued
0.6867	Remote Similarity	NPD17	Approved
0.6859	Remote Similarity	NPD7095	Approved
0.6855	Remote Similarity	NPD6653	Approved
0.6854	Remote Similarity	NPD7472	Approved
0.6852	Remote Similarity	NPD1549	Phase 2
0.6836	Remote Similarity	NPD7799	Discontinued
0.6836	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD3751	Discontinued
0.6835	Remote Similarity	NPD4140	Approved
0.6833	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6798	Discontinued
0.6815	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3764	Approved
0.681	Remote Similarity	NPD2800	Approved
0.68	Remote Similarity	NPD3787	Discontinued
0.6798	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6832	Phase 2
0.6793	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD230	Phase 1
0.679	Remote Similarity	NPD2344	Approved
0.679	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7251	Discontinued
0.6778	Remote Similarity	NPD7240	Approved
0.6774	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8032	Phase 2
0.677	Remote Similarity	NPD4308	Phase 3
0.6768	Remote Similarity	NPD8166	Discontinued
0.6761	Remote Similarity	NPD3926	Phase 2
0.6755	Remote Similarity	NPD1778	Approved
0.6752	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1511	Approved
0.6743	Remote Similarity	NPD6959	Discontinued
0.674	Remote Similarity	NPD7808	Phase 3
0.6732	Remote Similarity	NPD3972	Approved
0.673	Remote Similarity	NPD4060	Phase 1
0.6728	Remote Similarity	NPD2438	Suspended
0.6727	Remote Similarity	NPD2354	Approved
0.6727	Remote Similarity	NPD3887	Approved
0.6723	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6797	Phase 2
0.6719	Remote Similarity	NPD7435	Discontinued
0.671	Remote Similarity	NPD2797	Approved
0.6709	Remote Similarity	NPD3268	Approved
0.6709	Remote Similarity	NPD2313	Discontinued
0.6708	Remote Similarity	NPD7097	Phase 1
0.6707	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD447	Suspended
0.6687	Remote Similarity	NPD5735	Approved
0.6667	Remote Similarity	NPD6385	Approved
0.6667	Remote Similarity	NPD3057	Approved
0.6667	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD1510	Phase 2
0.6667	Remote Similarity	NPD6386	Approved
0.6649	Remote Similarity	NPD4107	Approved
0.6648	Remote Similarity	NPD7177	Discontinued
0.6647	Remote Similarity	NPD5353	Approved
0.6646	Remote Similarity	NPD4534	Discontinued
0.6646	Remote Similarity	NPD1607	Approved
0.6646	Remote Similarity	NPD2424	Discontinued
0.6645	Remote Similarity	NPD1283	Approved
0.6627	Remote Similarity	NPD2309	Approved
0.6625	Remote Similarity	NPD4307	Phase 2
0.6625	Remote Similarity	NPD2979	Phase 3
0.6625	Remote Similarity	NPD1240	Approved
0.6624	Remote Similarity	NPD9494	Approved
0.6623	Remote Similarity	NPD9545	Approved
0.6613	Remote Similarity	NPD8360	Approved
0.6613	Remote Similarity	NPD8361	Approved
0.6613	Remote Similarity	NPD8435	Approved
0.661	Remote Similarity	NPD5710	Approved
0.661	Remote Similarity	NPD5711	Approved
0.661	Remote Similarity	NPD7315	Approved
0.6608	Remote Similarity	NPD7028	Phase 2
0.6604	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7985	Registered
0.6584	Remote Similarity	NPD5124	Phase 1
0.6584	Remote Similarity	NPD4665	Approved
0.6584	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4111	Phase 1
0.658	Remote Similarity	NPD2972	Approved
0.658	Remote Similarity	NPD3533	Approved
0.6579	Remote Similarity	NPD5585	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