NPASS Compound

Structure

NPC81912 OpenBabel07101719152D 29 30 0 0 1 0 0 0 0 0999 V2000 4.2541 -1.9499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6812 -3.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2091 -2.9890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8541 -4.5267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4271 -2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2992 -4.8888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9586 -3.5322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6631 -5.1145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2361 -3.3511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3857 -5.2955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5135 -3.1701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4038 -3.8943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1833 -3.9876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9265 -3.3184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5252 -2.5094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1496 -2.9444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5767 -4.7078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7045 -2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3173 -3.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5197 -2.4049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 17 22 2 0 0 0 0 17 28 1 0 0 0 0 18 1 1 6 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 23 16 1 6 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 25 27 2 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.25
Volume:	440.549
LogP:	4.555
LogD:	4.307
LogS:	-4.923
# Rotatable Bonds:	11
TPSA:	66.74
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	4.094
Fsp3:	0.44
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:	-4.749
MDCK Permeability:	2.708600732148625e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	99.63579559326172%
Volume Distribution (VD):	3.023
Pgp-substrate:	0.8083695769309998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.343
CYP1A2-substrate:	0.834
CYP2C19-inhibitor:	0.783
CYP2C19-substrate:	0.176
CYP2C9-inhibitor:	0.831
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.868
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.727
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	8.882
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.762
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.563
Skin Sensitization:	0.4
Carcinogencity:	0.851
Eye Corrosion:	0.003
Eye Irritation:	0.06
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: NPC81912

Natural Product ID:	NPC81912
*Common Name:**	Epi-Sarcotin A
IUPAC Name:	(2R)-2-[(2Z,6S,7E,9E)-13-(furan-3-yl)-2,6,10-trimethyltrideca-2,7,9-trienyl]-3-hydroxy-4-methyl-2H-furan-5-one
Synonyms:
Standard InCHIKey:	UXFNAATUJSSAHF-CNGQNWGCSA-N
Standard InCHI:	InChI=1S/C25H34O4/c1-18(8-5-9-19(2)11-7-13-22-14-15-28-17-22)10-6-12-20(3)16-23-24(26)21(4)25(27)29-23/h5,8-9,12,14-15,17-18,23,26H,6-7,10-11,13,16H2,1-4H3/b8-5+,19-9+,20-12-/t18-,23-/m1/s1
SMILES:	C[C@H](/C=C/C=C(C)/CCCc1ccoc1)CC/C=C(/C)C[C@@H]1C(=C(C)C(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482611
PubChem CID:	54718147
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678655]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350153]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341287]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	12.3	ug ml-1	PMID[545397]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	9.6	ug ml-1	PMID[545397]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	5.6	ug ml-1	PMID[545397]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	9.8	ug ml-1	PMID[545397]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	6.5	ug ml-1	PMID[545397]

☑ 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 NPC81912 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	231
0.1-0.2	1088
0.2-0.3	3373
0.3-0.4	8615
0.4-0.5	11499
0.5-0.6	9821
0.6-0.7	7353
0.7-0.8	602
0.8-0.85	69
0.85-0.9	25
0.9-0.95	10
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329922
1.0	High Similarity	NPC329694
1.0	High Similarity	NPC474260
0.975	High Similarity	NPC476016
0.9748	High Similarity	NPC75557
0.9748	High Similarity	NPC71274
0.9746	High Similarity	NPC475818
0.9669	High Similarity	NPC474438
0.9669	High Similarity	NPC474279
0.9587	High Similarity	NPC474830
0.958	High Similarity	NPC476351
0.9496	High Similarity	NPC289911
0.9496	High Similarity	NPC283284
0.9492	High Similarity	NPC474817
0.9421	High Similarity	NPC474829
0.9412	High Similarity	NPC474136
0.9244	High Similarity	NPC473969
0.9237	High Similarity	NPC144745
0.9237	High Similarity	NPC208906
0.9127	High Similarity	NPC17681
0.9106	High Similarity	NPC471559
0.9076	High Similarity	NPC131801
0.9055	High Similarity	NPC97740
0.896	High Similarity	NPC471554
0.896	High Similarity	NPC471573
0.896	High Similarity	NPC473355
0.896	High Similarity	NPC471501
0.8906	High Similarity	NPC45358
0.8862	High Similarity	NPC473379
0.8862	High Similarity	NPC471549
0.8855	High Similarity	NPC215109
0.8855	High Similarity	NPC170604
0.8837	High Similarity	NPC474426
0.8837	High Similarity	NPC474425
0.8837	High Similarity	NPC474407
0.881	High Similarity	NPC137570
0.8729	High Similarity	NPC105249
0.872	High Similarity	NPC243269
0.8702	High Similarity	NPC14650
0.8655	High Similarity	NPC1811
0.8655	High Similarity	NPC26157
0.8636	High Similarity	NPC303217
0.8626	High Similarity	NPC288209
0.848	Intermediate Similarity	NPC1848
0.8475	Intermediate Similarity	NPC473356
0.8475	Intermediate Similarity	NPC471521
0.8468	Intermediate Similarity	NPC4898
0.8444	Intermediate Similarity	NPC107571
0.8443	Intermediate Similarity	NPC28054
0.8438	Intermediate Similarity	NPC138139
0.8438	Intermediate Similarity	NPC46536
0.8425	Intermediate Similarity	NPC188377
0.8425	Intermediate Similarity	NPC118853
0.8425	Intermediate Similarity	NPC65735
0.8413	Intermediate Similarity	NPC477967
0.8397	Intermediate Similarity	NPC89133
0.8387	Intermediate Similarity	NPC21831
0.8387	Intermediate Similarity	NPC187547
0.8372	Intermediate Similarity	NPC83178
0.8333	Intermediate Similarity	NPC471545
0.8333	Intermediate Similarity	NPC471544
0.8333	Intermediate Similarity	NPC473344
0.8308	Intermediate Similarity	NPC112706
0.8308	Intermediate Similarity	NPC207294
0.8296	Intermediate Similarity	NPC473268
0.8284	Intermediate Similarity	NPC159786
0.8273	Intermediate Similarity	NPC218712
0.8273	Intermediate Similarity	NPC267004
0.8273	Intermediate Similarity	NPC261733
0.8273	Intermediate Similarity	NPC307346
0.8268	Intermediate Similarity	NPC263870
0.825	Intermediate Similarity	NPC177331
0.8217	Intermediate Similarity	NPC179354
0.8203	Intermediate Similarity	NPC16922
0.8195	Intermediate Similarity	NPC471817
0.8195	Intermediate Similarity	NPC473982
0.8189	Intermediate Similarity	NPC79557
0.8175	Intermediate Similarity	NPC90953
0.816	Intermediate Similarity	NPC217180
0.816	Intermediate Similarity	NPC312525
0.8156	Intermediate Similarity	NPC104924
0.8148	Intermediate Similarity	NPC476947
0.814	Intermediate Similarity	NPC477038
0.814	Intermediate Similarity	NPC477965
0.8134	Intermediate Similarity	NPC218838
0.8125	Intermediate Similarity	NPC317217
0.812	Intermediate Similarity	NPC298190
0.812	Intermediate Similarity	NPC136340
0.8112	Intermediate Similarity	NPC234494
0.8095	Intermediate Similarity	NPC243704
0.8095	Intermediate Similarity	NPC291619
0.8095	Intermediate Similarity	NPC254958
0.8092	Intermediate Similarity	NPC95567
0.8092	Intermediate Similarity	NPC319140
0.808	Intermediate Similarity	NPC45536
0.8071	Intermediate Similarity	NPC254198
0.8071	Intermediate Similarity	NPC80635
0.8029	Intermediate Similarity	NPC186626
0.8016	Intermediate Similarity	NPC227660
0.8015	Intermediate Similarity	NPC74612
0.8015	Intermediate Similarity	NPC23086
0.8015	Intermediate Similarity	NPC92941
0.8	Intermediate Similarity	NPC150895
0.8	Intermediate Similarity	NPC205523
0.8	Intermediate Similarity	NPC121158
0.8	Intermediate Similarity	NPC470740
0.7986	Intermediate Similarity	NPC125182
0.7986	Intermediate Similarity	NPC69647
0.7985	Intermediate Similarity	NPC61788
0.7972	Intermediate Similarity	NPC255414
0.7958	Intermediate Similarity	NPC34056
0.7956	Intermediate Similarity	NPC146872
0.7945	Intermediate Similarity	NPC33938
0.7945	Intermediate Similarity	NPC121615
0.7945	Intermediate Similarity	NPC294511
0.7943	Intermediate Similarity	NPC267632
0.7941	Intermediate Similarity	NPC106247
0.7937	Intermediate Similarity	NPC476031
0.7937	Intermediate Similarity	NPC476014
0.7931	Intermediate Similarity	NPC470997
0.7917	Intermediate Similarity	NPC7388
0.7914	Intermediate Similarity	NPC202260
0.791	Intermediate Similarity	NPC21460
0.7899	Intermediate Similarity	NPC470742
0.7895	Intermediate Similarity	NPC477123
0.7895	Intermediate Similarity	NPC477039
0.7895	Intermediate Similarity	NPC477040
0.7895	Intermediate Similarity	NPC477966
0.7891	Intermediate Similarity	NPC237259
0.7891	Intermediate Similarity	NPC34421
0.7891	Intermediate Similarity	NPC302054
0.7891	Intermediate Similarity	NPC253201
0.7891	Intermediate Similarity	NPC98206
0.7887	Intermediate Similarity	NPC137295
0.7887	Intermediate Similarity	NPC251865
0.7879	Intermediate Similarity	NPC216810
0.7863	Intermediate Similarity	NPC130275
0.7857	Intermediate Similarity	NPC56197
0.7852	Intermediate Similarity	NPC475092
0.7852	Intermediate Similarity	NPC472778
0.7852	Intermediate Similarity	NPC472776
0.7852	Intermediate Similarity	NPC472777
0.7847	Intermediate Similarity	NPC216755
0.7847	Intermediate Similarity	NPC471174
0.7842	Intermediate Similarity	NPC236532
0.7838	Intermediate Similarity	NPC141538
0.7838	Intermediate Similarity	NPC296807
0.7838	Intermediate Similarity	NPC155939
0.7836	Intermediate Similarity	NPC120836
0.7836	Intermediate Similarity	NPC223063
0.7832	Intermediate Similarity	NPC195920
0.7823	Intermediate Similarity	NPC472672
0.7823	Intermediate Similarity	NPC474219
0.7823	Intermediate Similarity	NPC268905
0.7823	Intermediate Similarity	NPC474378
0.7817	Intermediate Similarity	NPC22248
0.7817	Intermediate Similarity	NPC476946
0.7812	Intermediate Similarity	NPC293424
0.7808	Intermediate Similarity	NPC228842
0.7795	Intermediate Similarity	NPC474987
0.7795	Intermediate Similarity	NPC76844
0.7793	Intermediate Similarity	NPC93666
0.7793	Intermediate Similarity	NPC471007
0.7778	Intermediate Similarity	NPC346
0.7778	Intermediate Similarity	NPC476925
0.777	Intermediate Similarity	NPC310830
0.7762	Intermediate Similarity	NPC476944
0.7761	Intermediate Similarity	NPC26532
0.7761	Intermediate Similarity	NPC329707
0.7761	Intermediate Similarity	NPC476917
0.7761	Intermediate Similarity	NPC327527
0.7746	Intermediate Similarity	NPC52412
0.774	Intermediate Similarity	NPC472654
0.7733	Intermediate Similarity	NPC197137
0.7733	Intermediate Similarity	NPC194499
0.7733	Intermediate Similarity	NPC88007
0.7733	Intermediate Similarity	NPC7059
0.773	Intermediate Similarity	NPC201370
0.773	Intermediate Similarity	NPC282973
0.773	Intermediate Similarity	NPC473983
0.773	Intermediate Similarity	NPC67003
0.773	Intermediate Similarity	NPC148374
0.7724	Intermediate Similarity	NPC302987
0.7724	Intermediate Similarity	NPC71821
0.7724	Intermediate Similarity	NPC476937
0.7724	Intermediate Similarity	NPC250228
0.7724	Intermediate Similarity	NPC476938
0.7721	Intermediate Similarity	NPC477645
0.7718	Intermediate Similarity	NPC281258
0.7718	Intermediate Similarity	NPC92979
0.7718	Intermediate Similarity	NPC214541
0.7718	Intermediate Similarity	NPC44675
0.7717	Intermediate Similarity	NPC11821
0.7714	Intermediate Similarity	NPC220094
0.7714	Intermediate Similarity	NPC476943
0.771	Intermediate Similarity	NPC36255
0.7708	Intermediate Similarity	NPC5676
0.7704	Intermediate Similarity	NPC198904
0.7704	Intermediate Similarity	NPC208389
0.7703	Intermediate Similarity	NPC147168

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 NPC81912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	916
0.2-0.3	1944
0.3-0.4	2733
0.4-0.5	1993
0.5-0.6	1041
0.6-0.7	298
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.766	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7338	Intermediate Similarity	NPD6798	Discontinued
0.7319	Intermediate Similarity	NPD6832	Phase 2
0.7299	Intermediate Similarity	NPD5647	Approved
0.7259	Intermediate Similarity	NPD9717	Approved
0.7163	Intermediate Similarity	NPD4062	Phase 3
0.7163	Intermediate Similarity	NPD6233	Phase 2
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD5761	Phase 2
0.7133	Intermediate Similarity	NPD6653	Approved
0.7101	Intermediate Similarity	NPD2797	Approved
0.7075	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1241	Discontinued
0.702	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD6799	Approved
0.698	Remote Similarity	NPD2354	Approved
0.698	Remote Similarity	NPD3887	Approved
0.6978	Remote Similarity	NPD1203	Approved
0.6978	Remote Similarity	NPD6362	Approved
0.6972	Remote Similarity	NPD2313	Discontinued
0.6972	Remote Similarity	NPD3268	Approved
0.697	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1358	Approved
0.6947	Remote Similarity	NPD7843	Approved
0.6944	Remote Similarity	NPD447	Suspended
0.694	Remote Similarity	NPD9092	Discovery
0.6939	Remote Similarity	NPD6004	Phase 3
0.6939	Remote Similarity	NPD6002	Phase 3
0.6939	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6005	Phase 3
0.6934	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1019	Discontinued
0.6918	Remote Similarity	NPD4308	Phase 3
0.6913	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4110	Phase 3
0.6909	Remote Similarity	NPD6765	Approved
0.6909	Remote Similarity	NPD6764	Approved
0.6905	Remote Similarity	NPD8434	Phase 2
0.6899	Remote Similarity	NPD7075	Discontinued
0.6899	Remote Similarity	NPD2684	Approved
0.6892	Remote Similarity	NPD5958	Discontinued
0.6889	Remote Similarity	NPD1894	Discontinued
0.6889	Remote Similarity	NPD9545	Approved
0.6887	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1608	Approved
0.6879	Remote Similarity	NPD9494	Approved
0.6875	Remote Similarity	NPD3134	Approved
0.6871	Remote Similarity	NPD1551	Phase 2
0.6863	Remote Similarity	NPD5403	Approved
0.6853	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7097	Phase 1
0.6846	Remote Similarity	NPD2067	Discontinued
0.6842	Remote Similarity	NPD5401	Approved
0.6839	Remote Similarity	NPD6599	Discontinued
0.6828	Remote Similarity	NPD1933	Approved
0.6824	Remote Similarity	NPD2344	Approved
0.6821	Remote Similarity	NPD7440	Discontinued
0.6809	Remote Similarity	NPD2798	Approved
0.6807	Remote Similarity	NPD6559	Discontinued
0.6797	Remote Similarity	NPD5049	Phase 3
0.6791	Remote Similarity	NPD7157	Approved
0.6783	Remote Similarity	NPD7095	Approved
0.6779	Remote Similarity	NPD4534	Discontinued
0.6774	Remote Similarity	NPD7458	Discontinued
0.6774	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4307	Phase 2
0.6757	Remote Similarity	NPD2935	Discontinued
0.6757	Remote Similarity	NPD2240	Approved
0.6757	Remote Similarity	NPD2239	Approved
0.6753	Remote Similarity	NPD920	Approved
0.6752	Remote Similarity	NPD6801	Discontinued
0.6746	Remote Similarity	NPD6785	Approved
0.6746	Remote Similarity	NPD6784	Approved
0.6741	Remote Similarity	NPD9493	Approved
0.6739	Remote Similarity	NPD3496	Discontinued
0.6738	Remote Similarity	NPD3267	Approved
0.6738	Remote Similarity	NPD3266	Approved
0.6738	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD411	Approved
0.6732	Remote Similarity	NPD4662	Approved
0.6732	Remote Similarity	NPD4661	Approved
0.6712	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2346	Discontinued
0.6711	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5763	Approved
0.6711	Remote Similarity	NPD5762	Approved
0.6711	Remote Similarity	NPD2353	Approved
0.6692	Remote Similarity	NPD290	Approved
0.669	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6646	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD919	Approved
0.6645	Remote Similarity	NPD2309	Approved
0.6644	Remote Similarity	NPD4060	Phase 1
0.6643	Remote Similarity	NPD1481	Phase 2
0.6643	Remote Similarity	NPD3972	Approved
0.6641	Remote Similarity	NPD2182	Approved
0.6625	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3764	Approved
0.6619	Remote Similarity	NPD3847	Discontinued
0.6604	Remote Similarity	NPD7819	Suspended
0.6604	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2614	Approved
0.6594	Remote Similarity	NPD5585	Approved
0.6582	Remote Similarity	NPD6677	Suspended
0.6582	Remote Similarity	NPD7411	Suspended
0.6579	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7003	Approved
0.6579	Remote Similarity	NPD3750	Approved
0.6571	Remote Similarity	NPD1535	Discovery
0.6567	Remote Similarity	NPD5535	Approved
0.6564	Remote Similarity	NPD8127	Discontinued
0.6562	Remote Similarity	NPD5402	Approved
0.6556	Remote Similarity	NPD2424	Discontinued
0.6556	Remote Similarity	NPD1549	Phase 2
0.6549	Remote Similarity	NPD1283	Approved
0.6545	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2438	Suspended
0.6533	Remote Similarity	NPD4476	Approved
0.6533	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6032	Approved
0.6533	Remote Similarity	NPD2796	Approved
0.6533	Remote Similarity	NPD4477	Approved
0.6531	Remote Similarity	NPD3140	Approved
0.6531	Remote Similarity	NPD3142	Approved
0.6528	Remote Similarity	NPD454	Approved
0.6522	Remote Similarity	NPD7768	Phase 2
0.6522	Remote Similarity	NPD3882	Suspended
0.6516	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1243	Approved
0.6503	Remote Similarity	NPD987	Approved
0.6493	Remote Similarity	NPD969	Suspended
0.649	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1471	Phase 3
0.649	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4618	Approved
0.6486	Remote Similarity	NPD4622	Approved
0.6481	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD958	Approved
0.6471	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2629	Approved
0.6467	Remote Similarity	NPD3748	Approved
0.6463	Remote Similarity	NPD8032	Phase 2
0.646	Remote Similarity	NPD3817	Phase 2
0.646	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2651	Approved
0.6456	Remote Similarity	NPD2649	Approved
0.6447	Remote Similarity	NPD2897	Discontinued
0.6447	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1934	Approved
0.6438	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3225	Approved
0.6433	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6808	Phase 2
0.6424	Remote Similarity	NPD5712	Approved
0.6419	Remote Similarity	NPD4140	Approved
0.6419	Remote Similarity	NPD2979	Phase 3
0.6415	Remote Similarity	NPD4380	Phase 2
0.6412	Remote Similarity	NPD9697	Approved
0.6406	Remote Similarity	NPD1238	Approved
0.6405	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5688	Approved
0.64	Remote Similarity	NPD5689	Approved
0.6398	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8455	Phase 2
0.6391	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6647	Phase 2
0.638	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.638	Remote Similarity	NPD3749	Approved
0.6376	Remote Similarity	NPD230	Phase 1
0.6376	Remote Similarity	NPD4340	Discontinued
0.6369	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2163	Approved
0.6369	Remote Similarity	NPD3818	Discontinued
0.6364	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4359	Approved
0.6364	Remote Similarity	NPD8166	Discontinued
0.6364	Remote Similarity	NPD3685	Discontinued
0.6364	Remote Similarity	NPD7199	Phase 2
0.6358	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5691	Approved
0.6352	Remote Similarity	NPD3455	Phase 2
0.6352	Remote Similarity	NPD3226	Approved
0.6341	Remote Similarity	NPD6315	Phase 2
0.634	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD1281	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