NPASS Compound

Structure

NPC5676 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 -0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4648 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9833 0.3525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4286 -2.1095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0606 -1.5793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4985 -1.8603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4978 -0.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9589 -0.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1095 -1.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6679 0.9630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6679 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5019 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 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 0.8340 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 1.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7640 0.5862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8169 -0.0403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 24 1 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 6 0 0 0 15 16 1 0 0 0 0 15 21 1 1 0 0 0 16 17 1 0 0 0 0 16 22 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 1 0 0 0 19 20 1 6 0 0 0 20 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	358.695
LogP:	3.495
LogD:	3.642
LogS:	-4.368
# Rotatable Bonds:	3
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.793
Synthetic Accessibility Score:	4.608
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.688
MDCK Permeability:	2.7404197680880316e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.162
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.157
Plasma Protein Binding (PPB):	95.1143569946289%
Volume Distribution (VD):	1.848
Pgp-substrate:	5.444964408874512%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.517
CYP2C9-substrate:	0.46
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.298
CYP3A4-inhibitor:	0.31
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	10.257
Half-life (T1/2):	0.38

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.191
Carcinogencity:	0.703
Eye Corrosion:	0.006
Eye Irritation:	0.035
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC5676

Natural Product ID:	NPC5676
*Common Name:**	(5S,6S,7R,8R,9R,10S)-15,16-Epoxylabda-13(16),14-Diene-6Beta,7Beta,9Alpha-Triol
IUPAC Name:	(1S,2R,3R,4R,4aS,8aS)-4-[2-(furan-3-yl)ethyl]-3,4a,8,8-tetramethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalene-1,2,4-triol
Synonyms:
Standard InCHIKey:	NFEYELMBFDLTKE-DWIQROTPSA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-13-15(21)16(22)17-18(2,3)8-5-9-19(17,4)20(13,23)10-6-14-7-11-24-12-14/h7,11-13,15-17,21-23H,5-6,8-10H2,1-4H3/t13-,15-,16-,17+,19+,20-/m1/s1
SMILES:	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:	CHEMBL3234608
PubChem CID:	25137130
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[573294]

☑ 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 NPC5676 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	330
0.1-0.2	1230
0.2-0.3	2850
0.3-0.4	5518
0.4-0.5	10549
0.5-0.6	9365
0.6-0.7	10213
0.7-0.8	2231
0.8-0.85	294
0.85-0.9	99
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC125182
0.9716	High Similarity	NPC69647
0.9635	High Similarity	NPC67003
0.9574	High Similarity	NPC255414
0.9357	High Similarity	NPC121158
0.9291	High Similarity	NPC243577
0.927	High Similarity	NPC476947
0.9247	High Similarity	NPC268905
0.9155	High Similarity	NPC476946
0.9128	High Similarity	NPC194499
0.9091	High Similarity	NPC251865
0.9073	High Similarity	NPC200782
0.9041	High Similarity	NPC470998
0.9	High Similarity	NPC195954
0.9	High Similarity	NPC88007
0.8986	High Similarity	NPC218838
0.8973	High Similarity	NPC471007
0.894	High Similarity	NPC472671
0.894	High Similarity	NPC475967
0.8929	High Similarity	NPC46896
0.8926	High Similarity	NPC34421
0.8926	High Similarity	NPC237259
0.8926	High Similarity	NPC302054
0.8926	High Similarity	NPC98206
0.8926	High Similarity	NPC253201
0.8912	High Similarity	NPC472654
0.8889	High Similarity	NPC472773
0.8874	High Similarity	NPC214495
0.8874	High Similarity	NPC470119
0.8874	High Similarity	NPC475066
0.8874	High Similarity	NPC299038
0.8867	High Similarity	NPC92979
0.8859	High Similarity	NPC472672
0.8859	High Similarity	NPC469503
0.8859	High Similarity	NPC121615
0.8859	High Similarity	NPC294511
0.8851	High Similarity	NPC196846
0.8851	High Similarity	NPC470997
0.8851	High Similarity	NPC212257
0.8841	High Similarity	NPC61788
0.8839	High Similarity	NPC472775
0.8839	High Similarity	NPC472774
0.8824	High Similarity	NPC79571
0.8824	High Similarity	NPC68848
0.8824	High Similarity	NPC472771
0.8824	High Similarity	NPC470792
0.8819	High Similarity	NPC52412
0.8816	High Similarity	NPC475226
0.8811	High Similarity	NPC90296
0.88	High Similarity	NPC282445
0.8784	High Similarity	NPC195325
0.8776	High Similarity	NPC216755
0.8776	High Similarity	NPC471174
0.8776	High Similarity	NPC302987
0.8774	High Similarity	NPC93172
0.8774	High Similarity	NPC97574
0.8774	High Similarity	NPC472141
0.8766	High Similarity	NPC283209
0.8758	High Similarity	NPC470789
0.8758	High Similarity	NPC8389
0.875	High Similarity	NPC472772
0.875	High Similarity	NPC472776
0.875	High Similarity	NPC472777
0.875	High Similarity	NPC472778
0.8742	High Similarity	NPC141538
0.8742	High Similarity	NPC476262
0.8742	High Similarity	NPC264943
0.8742	High Similarity	NPC296807
0.8742	High Similarity	NPC155939
0.8733	High Similarity	NPC476201
0.8733	High Similarity	NPC470996
0.8733	High Similarity	NPC33938
0.8732	High Similarity	NPC4764
0.8725	High Similarity	NPC228842
0.8725	High Similarity	NPC476122
0.8723	High Similarity	NPC158525
0.871	High Similarity	NPC271657
0.871	High Similarity	NPC470182
0.871	High Similarity	NPC276551
0.8701	High Similarity	NPC149896
0.8701	High Similarity	NPC18986
0.8701	High Similarity	NPC188649
0.8701	High Similarity	NPC18347
0.8701	High Similarity	NPC82851
0.869	High Similarity	NPC263337
0.8684	High Similarity	NPC41880
0.8675	High Similarity	NPC178932
0.8675	High Similarity	NPC57998
0.8667	High Similarity	NPC18135
0.8662	High Similarity	NPC271235
0.8662	High Similarity	NPC471397
0.8658	High Similarity	NPC234494
0.8654	High Similarity	NPC121995
0.8654	High Similarity	NPC472670
0.8654	High Similarity	NPC307781
0.8654	High Similarity	NPC470875
0.8645	High Similarity	NPC88841
0.8645	High Similarity	NPC292389
0.8645	High Similarity	NPC288602
0.8645	High Similarity	NPC477405
0.8645	High Similarity	NPC285567
0.8645	High Similarity	NPC469338
0.8645	High Similarity	NPC234660
0.8645	High Similarity	NPC39986
0.8645	High Similarity	NPC472139
0.8645	High Similarity	NPC51568
0.8645	High Similarity	NPC302369
0.8645	High Similarity	NPC134254
0.8636	High Similarity	NPC335761
0.8636	High Similarity	NPC472653
0.8627	High Similarity	NPC470118
0.8627	High Similarity	NPC304692
0.8627	High Similarity	NPC45101
0.8627	High Similarity	NPC261597
0.8627	High Similarity	NPC7059
0.8627	High Similarity	NPC249021
0.8627	High Similarity	NPC197137
0.8618	High Similarity	NPC35000
0.8618	High Similarity	NPC214541
0.8618	High Similarity	NPC469336
0.8618	High Similarity	NPC44675
0.8609	High Similarity	NPC322546
0.8609	High Similarity	NPC182427
0.8609	High Similarity	NPC308205
0.8609	High Similarity	NPC29695
0.8609	High Similarity	NPC75906
0.8608	High Similarity	NPC470995
0.8599	High Similarity	NPC173516
0.8599	High Similarity	NPC472651
0.859	High Similarity	NPC476857
0.859	High Similarity	NPC469849
0.859	High Similarity	NPC476856
0.859	High Similarity	NPC470940
0.859	High Similarity	NPC476858
0.8581	High Similarity	NPC5741
0.8581	High Similarity	NPC69028
0.8581	High Similarity	NPC470999
0.8581	High Similarity	NPC5079
0.8581	High Similarity	NPC329938
0.8571	High Similarity	NPC474611
0.8571	High Similarity	NPC307383
0.8571	High Similarity	NPC476944
0.8571	High Similarity	NPC89133
0.8562	High Similarity	NPC104736
0.8562	High Similarity	NPC20578
0.8562	High Similarity	NPC62103
0.8562	High Similarity	NPC475519
0.8553	High Similarity	NPC30222
0.8544	High Similarity	NPC160651
0.8544	High Similarity	NPC472673
0.8544	High Similarity	NPC296558
0.8544	High Similarity	NPC472652
0.8542	High Similarity	NPC471996
0.8535	High Similarity	NPC277618
0.8533	High Similarity	NPC470791
0.8533	High Similarity	NPC211625
0.8533	High Similarity	NPC470790
0.8523	High Similarity	NPC221809
0.8523	High Similarity	NPC71821
0.8516	High Similarity	NPC477402
0.8516	High Similarity	NPC287559
0.8514	High Similarity	NPC185456
0.8514	High Similarity	NPC41182
0.8511	High Similarity	NPC471544
0.8511	High Similarity	NPC473344
0.8506	High Similarity	NPC167142
0.8506	High Similarity	NPC36655
0.8506	High Similarity	NPC187149
0.8493	Intermediate Similarity	NPC205765
0.8491	Intermediate Similarity	NPC82602
0.8483	Intermediate Similarity	NPC90953
0.8481	Intermediate Similarity	NPC472282
0.8481	Intermediate Similarity	NPC476853
0.8481	Intermediate Similarity	NPC476861
0.8481	Intermediate Similarity	NPC270312
0.8481	Intermediate Similarity	NPC476850
0.8477	Intermediate Similarity	NPC477404
0.8477	Intermediate Similarity	NPC156189
0.8477	Intermediate Similarity	NPC196864
0.8471	Intermediate Similarity	NPC56358
0.8462	Intermediate Similarity	NPC471166
0.8462	Intermediate Similarity	NPC211777
0.8462	Intermediate Similarity	NPC471167
0.8462	Intermediate Similarity	NPC472668
0.8462	Intermediate Similarity	NPC207978
0.8462	Intermediate Similarity	NPC263432
0.8431	Intermediate Similarity	NPC114880
0.8428	Intermediate Similarity	NPC472765
0.8428	Intermediate Similarity	NPC472766
0.8418	Intermediate Similarity	NPC23387
0.8411	Intermediate Similarity	NPC471001
0.8408	Intermediate Similarity	NPC472669
0.8408	Intermediate Similarity	NPC198047
0.8408	Intermediate Similarity	NPC471168
0.84	Intermediate Similarity	NPC286038
0.84	Intermediate Similarity	NPC470941
0.84	Intermediate Similarity	NPC250228
0.8397	Intermediate Similarity	NPC25255
0.838	Intermediate Similarity	NPC471545
0.8378	Intermediate Similarity	NPC64568

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 NPC5676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	886
0.2-0.3	1959
0.3-0.4	2658
0.4-0.5	1960
0.5-0.6	1017
0.6-0.7	351
0.7-0.8	19
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD5760	Phase 2
0.8742	High Similarity	NPD5761	Phase 2
0.8253	Intermediate Similarity	NPD8434	Phase 2
0.7829	Intermediate Similarity	NPD4628	Phase 3
0.7633	Intermediate Similarity	NPD6765	Approved
0.7633	Intermediate Similarity	NPD6764	Approved
0.7457	Intermediate Similarity	NPD6785	Approved
0.7457	Intermediate Similarity	NPD6784	Approved
0.7362	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5844	Phase 1
0.7349	Intermediate Similarity	NPD5494	Approved
0.7326	Intermediate Similarity	NPD6559	Discontinued
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6599	Discontinued
0.7256	Intermediate Similarity	NPD7819	Suspended
0.7256	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6273	Approved
0.7226	Intermediate Similarity	NPD6100	Approved
0.7226	Intermediate Similarity	NPD6099	Approved
0.7202	Intermediate Similarity	NPD8127	Discontinued
0.7195	Intermediate Similarity	NPD1934	Approved
0.7188	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4380	Phase 2
0.7169	Intermediate Similarity	NPD3882	Suspended
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8404	Phase 2
0.7126	Intermediate Similarity	NPD7075	Discontinued
0.7115	Intermediate Similarity	NPD2796	Approved
0.7108	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1247	Approved
0.7099	Intermediate Similarity	NPD920	Approved
0.7093	Intermediate Similarity	NPD3818	Discontinued
0.7089	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1471	Phase 3
0.7066	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2801	Approved
0.7025	Intermediate Similarity	NPD1549	Phase 2
0.7024	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6799	Approved
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6801	Discontinued
0.6982	Remote Similarity	NPD919	Approved
0.6981	Remote Similarity	NPD2800	Approved
0.6977	Remote Similarity	NPD6166	Phase 2
0.6977	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2532	Approved
0.6975	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2534	Approved
0.6975	Remote Similarity	NPD2533	Approved
0.6968	Remote Similarity	NPD6355	Discontinued
0.6962	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7236	Approved
0.6923	Remote Similarity	NPD3749	Approved
0.6914	Remote Similarity	NPD7074	Phase 3
0.6914	Remote Similarity	NPD1511	Approved
0.6913	Remote Similarity	NPD1608	Approved
0.6913	Remote Similarity	NPD3972	Approved
0.6909	Remote Similarity	NPD7458	Discontinued
0.6909	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3817	Phase 2
0.6901	Remote Similarity	NPD7199	Phase 2
0.6901	Remote Similarity	NPD6959	Discontinued
0.6899	Remote Similarity	NPD1551	Phase 2
0.6886	Remote Similarity	NPD37	Approved
0.6871	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4965	Approved
0.6864	Remote Similarity	NPD4966	Approved
0.6864	Remote Similarity	NPD4967	Phase 2
0.6862	Remote Similarity	NPD7497	Discontinued
0.6859	Remote Similarity	NPD5735	Approved
0.6857	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7054	Approved
0.6855	Remote Similarity	NPD6005	Phase 3
0.6855	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5762	Approved
0.6855	Remote Similarity	NPD6004	Phase 3
0.6855	Remote Similarity	NPD6002	Phase 3
0.6855	Remote Similarity	NPD5763	Approved
0.6839	Remote Similarity	NPD7473	Discontinued
0.6835	Remote Similarity	NPD1510	Phase 2
0.6835	Remote Similarity	NPD7033	Discontinued
0.6835	Remote Similarity	NPD2799	Discontinued
0.6832	Remote Similarity	NPD3750	Approved
0.6832	Remote Similarity	NPD4110	Phase 3
0.6832	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1512	Approved
0.6829	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7411	Suspended
0.6821	Remote Similarity	NPD3926	Phase 2
0.6818	Remote Similarity	NPD7472	Approved
0.6815	Remote Similarity	NPD1607	Approved
0.6813	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3226	Approved
0.6805	Remote Similarity	NPD5402	Approved
0.68	Remote Similarity	NPD3751	Discontinued
0.6795	Remote Similarity	NPD1240	Approved
0.6792	Remote Similarity	NPD2935	Discontinued
0.679	Remote Similarity	NPD2309	Approved
0.6784	Remote Similarity	NPD6234	Discontinued
0.6782	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1243	Approved
0.6765	Remote Similarity	NPD7768	Phase 2
0.6763	Remote Similarity	NPD7229	Phase 3
0.6763	Remote Similarity	NPD6232	Discontinued
0.6763	Remote Similarity	NPD3787	Discontinued
0.676	Remote Similarity	NPD8312	Approved
0.676	Remote Similarity	NPD8313	Approved
0.675	Remote Similarity	NPD2346	Discontinued
0.6747	Remote Similarity	NPD7239	Suspended
0.6742	Remote Similarity	NPD7685	Pre-registration
0.6742	Remote Similarity	NPD7251	Discontinued
0.673	Remote Similarity	NPD3748	Approved
0.6728	Remote Similarity	NPD7003	Approved
0.6724	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8407	Phase 2
0.672	Remote Similarity	NPD3057	Approved
0.6711	Remote Similarity	NPD6696	Suspended
0.6711	Remote Similarity	NPD17	Approved
0.6708	Remote Similarity	NPD2424	Discontinued
0.6707	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7228	Approved
0.6705	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7808	Phase 3
0.6688	Remote Similarity	NPD4140	Approved
0.6688	Remote Similarity	NPD9494	Approved
0.6687	Remote Similarity	NPD6190	Approved
0.6687	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5403	Approved
0.6685	Remote Similarity	NPD6797	Phase 2
0.6685	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6648	Remote Similarity	NPD8150	Discontinued
0.6648	Remote Similarity	NPD8368	Discontinued
0.6647	Remote Similarity	NPD8455	Phase 2
0.6647	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD230	Phase 1
0.6645	Remote Similarity	NPD6832	Phase 2
0.6633	Remote Similarity	NPD4665	Approved
0.6633	Remote Similarity	NPD4111	Phase 1
0.6632	Remote Similarity	NPD3533	Approved
0.6632	Remote Similarity	NPD2972	Approved
0.6626	Remote Similarity	NPD8166	Discontinued
0.6625	Remote Similarity	NPD4308	Phase 3
0.6624	Remote Similarity	NPD8032	Phase 2
0.6624	Remote Similarity	NPD6233	Phase 2
0.6623	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7799	Discontinued
0.661	Remote Similarity	NPD2163	Approved
0.6604	Remote Similarity	NPD6651	Approved
0.6604	Remote Similarity	NPD6653	Approved
0.6603	Remote Similarity	NPD7095	Approved
0.6601	Remote Similarity	NPD1876	Approved
0.6601	Remote Similarity	NPD8651	Approved
0.66	Remote Similarity	NPD1778	Approved
0.6599	Remote Similarity	NPD7157	Approved
0.6591	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2861	Phase 2
0.6576	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7028	Phase 2
0.6567	Remote Similarity	NPD7907	Approved
0.6566	Remote Similarity	NPD7047	Phase 3
0.6561	Remote Similarity	NPD3268	Approved
0.6561	Remote Similarity	NPD6798	Discontinued
0.6561	Remote Similarity	NPD2313	Discontinued
0.6558	Remote Similarity	NPD2797	Approved
0.6556	Remote Similarity	NPD7240	Approved
0.6545	Remote Similarity	NPD2491	Approved
0.6541	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5327	Phase 3
0.6526	Remote Similarity	NPD6778	Approved
0.6526	Remote Similarity	NPD6779	Approved
0.6526	Remote Similarity	NPD6780	Approved
0.6526	Remote Similarity	NPD6776	Approved
0.6526	Remote Similarity	NPD6782	Approved
0.6526	Remote Similarity	NPD6781	Approved
0.6526	Remote Similarity	NPD6777	Approved
0.6517	Remote Similarity	NPD7177	Discontinued
0.6516	Remote Similarity	NPD2798	Approved
0.6513	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7435	Discontinued
0.6509	Remote Similarity	NPD2651	Approved
0.6509	Remote Similarity	NPD2649	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