NPASS Compound

Structure

CID153990 OpenBabel06191715522D 23 23 0 0 0 0 0 0 0 0999 V2000 6.9282 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 23 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 20 2 3 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	317.2
Volume:	350.172
LogP:	3.224
LogD:	3.473
LogS:	-3.366
# Rotatable Bonds:	11
TPSA:	58.56
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.51
Synthetic Accessibility Score:	2.476
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74
MDCK Permeability:	3.1478739401791245e-05
Pgp-inhibitor:	0.72
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.711

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.815
Plasma Protein Binding (PPB):	96.10350799560547%
Volume Distribution (VD):	1.005
Pgp-substrate:	3.5895369052886963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.889
CYP1A2-substrate:	0.926
CYP2C19-inhibitor:	0.824
CYP2C19-substrate:	0.622
CYP2C9-inhibitor:	0.739
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.907
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.37

ADMET: Excretion

Clearance (CL):	10.712
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.451
Human Hepatotoxicity (H-HT):	0.539
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.567
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.968
Carcinogencity:	0.428
Eye Corrosion:	0.003
Eye Irritation:	0.047
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC153990

Natural Product ID:	NPC153990
*Common Name:**	N-(4-Hydroxy-3-Methoxyphenethyl)Deca-2,4-Dienamide
IUPAC Name:	(2E,4E)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]deca-2,4-dienamide
Synonyms:
Standard InCHIKey:	ZEOWENGRGGSHMT-XBLVEGMJSA-N
Standard InCHI:	InChI=1S/C19H27NO3/c1-3-4-5-6-7-8-9-10-19(22)20-14-13-16-11-12-17(21)18(15-16)23-2/h7-12,15,21H,3-6,13-14H2,1-2H3,(H,20,22)/b8-7+,10-9+
SMILES:	CCCCC/C=C/C=C/C(=NCCc1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669581
PubChem CID:	50994065
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	whole plant	Luxi County, Yunnan Province, China	2008-OCT	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	8

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[548536]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[548536]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	>	40000.0	nM	PMID[548536]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[548536]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[548536]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	40000.0	nM	PMID[548536]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	40000.0	nM	PMID[548536]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[548536]

☑ 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 NPC153990 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	176
0.1-0.2	1515
0.2-0.3	8355
0.3-0.4	10218
0.4-0.5	5659
0.5-0.6	10289
0.6-0.7	4932
0.7-0.8	1377
0.8-0.85	110
0.85-0.9	36
0.9-0.95	24
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC214869
0.9593	High Similarity	NPC155838
0.952	High Similarity	NPC93882
0.952	High Similarity	NPC130595
0.9516	High Similarity	NPC52029
0.9516	High Similarity	NPC35961
0.9516	High Similarity	NPC195749
0.9444	High Similarity	NPC6854
0.9444	High Similarity	NPC285078
0.9444	High Similarity	NPC313737
0.944	High Similarity	NPC114102
0.9431	High Similarity	NPC301713
0.937	High Similarity	NPC218530
0.9355	High Similarity	NPC251571
0.9286	High Similarity	NPC255550
0.9286	High Similarity	NPC308885
0.92	High Similarity	NPC186898
0.9154	High Similarity	NPC312770
0.9154	High Similarity	NPC14600
0.9154	High Similarity	NPC41473
0.9154	High Similarity	NPC204848
0.9154	High Similarity	NPC160607
0.9084	High Similarity	NPC299583
0.9032	High Similarity	NPC140359
0.9032	High Similarity	NPC13020
0.8939	High Similarity	NPC296898
0.8833	High Similarity	NPC142599
0.875	High Similarity	NPC99798
0.875	High Similarity	NPC157740
0.8686	High Similarity	NPC5462
0.8682	High Similarity	NPC246974
0.8682	High Similarity	NPC147247
0.8672	High Similarity	NPC156944
0.8672	High Similarity	NPC251466
0.8618	High Similarity	NPC283468
0.8605	High Similarity	NPC291449
0.8605	High Similarity	NPC191302
0.8605	High Similarity	NPC41331
0.8603	High Similarity	NPC222039
0.8603	High Similarity	NPC100478
0.8594	High Similarity	NPC170583
0.8594	High Similarity	NPC246133
0.8594	High Similarity	NPC182147
0.8594	High Similarity	NPC207541
0.8594	High Similarity	NPC71105
0.8594	High Similarity	NPC152186
0.8583	High Similarity	NPC156840
0.8583	High Similarity	NPC8547
0.8583	High Similarity	NPC173746
0.8583	High Similarity	NPC257124
0.8561	High Similarity	NPC277857
0.8561	High Similarity	NPC115144
0.855	High Similarity	NPC329595
0.855	High Similarity	NPC326599
0.8548	High Similarity	NPC122009
0.8516	High Similarity	NPC300955
0.85	High Similarity	NPC471032
0.85	High Similarity	NPC470935
0.848	Intermediate Similarity	NPC268572
0.848	Intermediate Similarity	NPC43275
0.8473	Intermediate Similarity	NPC470706
0.8468	Intermediate Similarity	NPC164386
0.8468	Intermediate Similarity	NPC120075
0.843	Intermediate Similarity	NPC166837
0.8417	Intermediate Similarity	NPC36108
0.8417	Intermediate Similarity	NPC7097
0.8417	Intermediate Similarity	NPC246358
0.8417	Intermediate Similarity	NPC233731
0.8413	Intermediate Similarity	NPC53596
0.8413	Intermediate Similarity	NPC471308
0.8413	Intermediate Similarity	NPC160120
0.8413	Intermediate Similarity	NPC289330
0.8413	Intermediate Similarity	NPC17388
0.84	Intermediate Similarity	NPC470626
0.8397	Intermediate Similarity	NPC469977
0.8369	Intermediate Similarity	NPC153644
0.8359	Intermediate Similarity	NPC298486
0.8333	Intermediate Similarity	NPC311595
0.8333	Intermediate Similarity	NPC24474
0.8333	Intermediate Similarity	NPC310338
0.8333	Intermediate Similarity	NPC281298
0.8322	Intermediate Similarity	NPC127402
0.8321	Intermediate Similarity	NPC477838
0.8321	Intermediate Similarity	NPC477837
0.832	Intermediate Similarity	NPC293619
0.8309	Intermediate Similarity	NPC254610
0.8279	Intermediate Similarity	NPC139617
0.8279	Intermediate Similarity	NPC195873
0.8279	Intermediate Similarity	NPC78918
0.8268	Intermediate Similarity	NPC232316
0.8268	Intermediate Similarity	NPC263835
0.8268	Intermediate Similarity	NPC227217
0.8268	Intermediate Similarity	NPC242885
0.8268	Intermediate Similarity	NPC95614
0.8268	Intermediate Similarity	NPC56214
0.8268	Intermediate Similarity	NPC117780
0.8268	Intermediate Similarity	NPC165133
0.8264	Intermediate Similarity	NPC275027
0.8248	Intermediate Similarity	NPC231572
0.824	Intermediate Similarity	NPC221049
0.8235	Intermediate Similarity	NPC131204
0.8235	Intermediate Similarity	NPC301050
0.8231	Intermediate Similarity	NPC95733
0.8231	Intermediate Similarity	NPC62101
0.8222	Intermediate Similarity	NPC473463
0.8217	Intermediate Similarity	NPC471315
0.8217	Intermediate Similarity	NPC471314
0.8203	Intermediate Similarity	NPC207613
0.8203	Intermediate Similarity	NPC83279
0.8203	Intermediate Similarity	NPC183262
0.8197	Intermediate Similarity	NPC137685
0.8194	Intermediate Similarity	NPC52475
0.8175	Intermediate Similarity	NPC193528
0.8175	Intermediate Similarity	NPC86947
0.8154	Intermediate Similarity	NPC211218
0.8151	Intermediate Similarity	NPC107602
0.814	Intermediate Similarity	NPC312675
0.814	Intermediate Similarity	NPC201777
0.814	Intermediate Similarity	NPC324571
0.814	Intermediate Similarity	NPC54872
0.814	Intermediate Similarity	NPC38996
0.814	Intermediate Similarity	NPC343720
0.814	Intermediate Similarity	NPC470212
0.814	Intermediate Similarity	NPC473853
0.814	Intermediate Similarity	NPC113865
0.814	Intermediate Similarity	NPC262156
0.814	Intermediate Similarity	NPC160380
0.814	Intermediate Similarity	NPC184651
0.8138	Intermediate Similarity	NPC18614
0.8134	Intermediate Similarity	NPC476570
0.811	Intermediate Similarity	NPC255675
0.8099	Intermediate Similarity	NPC142297
0.8088	Intermediate Similarity	NPC284855
0.8088	Intermediate Similarity	NPC282477
0.8077	Intermediate Similarity	NPC85488
0.8065	Intermediate Similarity	NPC146422
0.8062	Intermediate Similarity	NPC284078
0.8058	Intermediate Similarity	NPC77572
0.8056	Intermediate Similarity	NPC182119
0.8047	Intermediate Similarity	NPC299406
0.8047	Intermediate Similarity	NPC181969
0.8047	Intermediate Similarity	NPC20674
0.8047	Intermediate Similarity	NPC320987
0.8045	Intermediate Similarity	NPC172403
0.8042	Intermediate Similarity	NPC179825
0.8042	Intermediate Similarity	NPC191376
0.8042	Intermediate Similarity	NPC321505
0.803	Intermediate Similarity	NPC29477
0.8017	Intermediate Similarity	NPC231705
0.8016	Intermediate Similarity	NPC303370
0.8015	Intermediate Similarity	NPC257976
0.8015	Intermediate Similarity	NPC471693
0.8015	Intermediate Similarity	NPC242372
0.8015	Intermediate Similarity	NPC164778
0.8015	Intermediate Similarity	NPC280704
0.8015	Intermediate Similarity	NPC4181
0.8015	Intermediate Similarity	NPC163083
0.8015	Intermediate Similarity	NPC317769
0.8015	Intermediate Similarity	NPC31344
0.8	Intermediate Similarity	NPC292792
0.8	Intermediate Similarity	NPC290451
0.8	Intermediate Similarity	NPC478189
0.8	Intermediate Similarity	NPC211992
0.8	Intermediate Similarity	NPC476343
0.8	Intermediate Similarity	NPC127389
0.8	Intermediate Similarity	NPC470804
0.8	Intermediate Similarity	NPC66518
0.7987	Intermediate Similarity	NPC329837
0.7986	Intermediate Similarity	NPC135538
0.7986	Intermediate Similarity	NPC428
0.7986	Intermediate Similarity	NPC24233
0.7986	Intermediate Similarity	NPC246587
0.7986	Intermediate Similarity	NPC476571
0.7986	Intermediate Similarity	NPC147390
0.7984	Intermediate Similarity	NPC35071
0.7984	Intermediate Similarity	NPC148615
0.7984	Intermediate Similarity	NPC177475
0.7969	Intermediate Similarity	NPC85276
0.7967	Intermediate Similarity	NPC258056
0.7955	Intermediate Similarity	NPC273686
0.7955	Intermediate Similarity	NPC60517
0.7955	Intermediate Similarity	NPC312404
0.7955	Intermediate Similarity	NPC105513
0.7955	Intermediate Similarity	NPC146886
0.7955	Intermediate Similarity	NPC20443
0.7951	Intermediate Similarity	NPC227894
0.7943	Intermediate Similarity	NPC908
0.7943	Intermediate Similarity	NPC138438
0.7939	Intermediate Similarity	NPC41562
0.7939	Intermediate Similarity	NPC114298
0.7931	Intermediate Similarity	NPC103379
0.7931	Intermediate Similarity	NPC477565
0.7923	Intermediate Similarity	NPC224814
0.7923	Intermediate Similarity	NPC60962
0.7923	Intermediate Similarity	NPC14007
0.7923	Intermediate Similarity	NPC158949
0.7923	Intermediate Similarity	NPC269843
0.7923	Intermediate Similarity	NPC189844
0.7923	Intermediate Similarity	NPC109083
0.792	Intermediate Similarity	NPC165646

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 NPC153990 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	761
0.2-0.3	1206
0.3-0.4	2246
0.4-0.5	2439
0.5-0.6	1491
0.6-0.7	681
0.7-0.8	172
0.8-0.85	8
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.952	High Similarity	NPD2674	Phase 3
0.9286	High Similarity	NPD3144	Approved
0.9286	High Similarity	NPD3145	Approved
0.8583	High Similarity	NPD228	Approved
0.8519	High Similarity	NPD2161	Phase 2
0.8394	Intermediate Similarity	NPD7153	Discontinued
0.8273	Intermediate Similarity	NPD6331	Phase 2
0.8154	Intermediate Similarity	NPD1669	Approved
0.8154	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD3060	Approved
0.8065	Intermediate Similarity	NPD9377	Approved
0.8065	Intermediate Similarity	NPD9379	Approved
0.8042	Intermediate Similarity	NPD4739	Approved
0.8042	Intermediate Similarity	NPD4123	Phase 3
0.8014	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5718	Phase 2
0.7955	Intermediate Similarity	NPD2922	Phase 1
0.7929	Intermediate Similarity	NPD1375	Discontinued
0.7926	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1558	Phase 1
0.7862	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7526	Approved
0.7862	Intermediate Similarity	NPD52	Approved
0.7846	Intermediate Similarity	NPD2667	Approved
0.7846	Intermediate Similarity	NPD2668	Approved
0.7832	Intermediate Similarity	NPD5241	Discontinued
0.7817	Intermediate Similarity	NPD4162	Approved
0.781	Intermediate Similarity	NPD839	Approved
0.781	Intermediate Similarity	NPD840	Approved
0.7803	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4675	Approved
0.777	Intermediate Similarity	NPD4678	Approved
0.7761	Intermediate Similarity	NPD3055	Approved
0.7761	Intermediate Similarity	NPD3053	Approved
0.7744	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5773	Approved
0.7733	Intermediate Similarity	NPD5772	Approved
0.7717	Intermediate Similarity	NPD5283	Phase 1
0.7714	Intermediate Similarity	NPD6895	Approved
0.7714	Intermediate Similarity	NPD6896	Approved
0.771	Intermediate Similarity	NPD9384	Approved
0.771	Intermediate Similarity	NPD9381	Approved
0.7703	Intermediate Similarity	NPD4005	Discontinued
0.7687	Intermediate Similarity	NPD5311	Approved
0.7687	Intermediate Similarity	NPD5310	Approved
0.7681	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2233	Approved
0.7669	Intermediate Similarity	NPD2232	Approved
0.7669	Intermediate Similarity	NPD2230	Approved
0.7664	Intermediate Similarity	NPD3027	Phase 3
0.7647	Intermediate Similarity	NPD1712	Approved
0.7643	Intermediate Similarity	NPD2157	Approved
0.7643	Intermediate Similarity	NPD2653	Approved
0.7638	Intermediate Similarity	NPD821	Approved
0.7616	Intermediate Similarity	NPD2978	Approved
0.7616	Intermediate Similarity	NPD2977	Approved
0.7612	Intermediate Similarity	NPD9622	Approved
0.7609	Intermediate Similarity	NPD5111	Phase 2
0.7609	Intermediate Similarity	NPD5110	Phase 2
0.7609	Intermediate Similarity	NPD5109	Approved
0.7586	Intermediate Similarity	NPD2219	Phase 1
0.7574	Intermediate Similarity	NPD9620	Approved
0.7574	Intermediate Similarity	NPD9619	Approved
0.7574	Intermediate Similarity	NPD9621	Approved
0.7574	Intermediate Similarity	NPD6584	Phase 3
0.7569	Intermediate Similarity	NPD4236	Phase 3
0.7569	Intermediate Similarity	NPD4237	Approved
0.7569	Intermediate Similarity	NPD5177	Phase 3
0.7568	Intermediate Similarity	NPD2122	Discontinued
0.7556	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD1024	Discontinued
0.7535	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3687	Approved
0.7517	Intermediate Similarity	NPD3686	Approved
0.75	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD601	Approved
0.7482	Intermediate Similarity	NPD597	Approved
0.7482	Intermediate Similarity	NPD598	Approved
0.7468	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD824	Approved
0.746	Intermediate Similarity	NPD2684	Approved
0.7452	Intermediate Similarity	NPD4083	Discontinued
0.7431	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1132	Approved
0.7429	Intermediate Similarity	NPD1136	Approved
0.7429	Intermediate Similarity	NPD1130	Approved
0.7407	Intermediate Similarity	NPD2231	Phase 2
0.7407	Intermediate Similarity	NPD2235	Phase 2
0.7402	Intermediate Similarity	NPD3021	Approved
0.7402	Intermediate Similarity	NPD3022	Approved
0.7379	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD3059	Approved
0.7376	Intermediate Similarity	NPD3062	Approved
0.7376	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD3061	Approved
0.7376	Intermediate Similarity	NPD2238	Phase 2
0.7376	Intermediate Similarity	NPD3620	Phase 2
0.7372	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5089	Approved
0.7368	Intermediate Similarity	NPD5090	Approved
0.7365	Intermediate Similarity	NPD4357	Discontinued
0.7357	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4055	Discovery
0.7353	Intermediate Similarity	NPD6582	Phase 2
0.7353	Intermediate Similarity	NPD6583	Phase 3
0.7353	Intermediate Similarity	NPD3685	Discontinued
0.7347	Intermediate Similarity	NPD3692	Discontinued
0.7344	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6111	Discontinued
0.7338	Intermediate Similarity	NPD596	Approved
0.7338	Intermediate Similarity	NPD600	Approved
0.7333	Intermediate Similarity	NPD9296	Approved
0.731	Intermediate Similarity	NPD3656	Approved
0.7308	Intermediate Similarity	NPD2229	Approved
0.7308	Intermediate Similarity	NPD2228	Approved
0.7308	Intermediate Similarity	NPD2234	Approved
0.7305	Intermediate Similarity	NPD7477	Discontinued
0.7305	Intermediate Similarity	NPD1423	Approved
0.7305	Intermediate Similarity	NPD259	Phase 1
0.7302	Intermediate Similarity	NPD1444	Approved
0.7302	Intermediate Similarity	NPD1445	Approved
0.7297	Intermediate Similarity	NPD7124	Phase 2
0.7292	Intermediate Similarity	NPD4108	Discontinued
0.7273	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5314	Approved
0.7266	Intermediate Similarity	NPD9494	Approved
0.7244	Intermediate Similarity	NPD7833	Phase 2
0.7244	Intermediate Similarity	NPD5604	Discontinued
0.7244	Intermediate Similarity	NPD7831	Phase 2
0.7244	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3111	Phase 1
0.7234	Intermediate Similarity	NPD1039	Discontinued
0.7231	Intermediate Similarity	NPD7843	Approved
0.723	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2563	Approved
0.7226	Intermediate Similarity	NPD2560	Approved
0.7218	Intermediate Similarity	NPD5536	Phase 2
0.7203	Intermediate Similarity	NPD555	Phase 2
0.72	Intermediate Similarity	NPD4584	Approved
0.7197	Intermediate Similarity	NPD7157	Approved
0.7197	Intermediate Similarity	NPD709	Approved
0.7194	Intermediate Similarity	NPD558	Phase 2
0.7194	Intermediate Similarity	NPD7905	Discontinued
0.7188	Intermediate Similarity	NPD2898	Approved
0.7188	Intermediate Similarity	NPD27	Approved
0.7188	Intermediate Similarity	NPD2489	Approved
0.7181	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4010	Discontinued
0.7161	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3052	Approved
0.7153	Intermediate Similarity	NPD823	Approved
0.7153	Intermediate Similarity	NPD3054	Approved
0.7153	Intermediate Similarity	NPD2492	Phase 1
0.7153	Intermediate Similarity	NPD817	Approved
0.7143	Intermediate Similarity	NPD9608	Approved
0.7143	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9569	Approved
0.7143	Intermediate Similarity	NPD9610	Approved
0.7143	Intermediate Similarity	NPD4993	Discontinued
0.7143	Intermediate Similarity	NPD4772	Phase 2
0.7143	Intermediate Similarity	NPD2808	Discontinued
0.7143	Intermediate Similarity	NPD4773	Phase 2
0.7133	Intermediate Similarity	NPD826	Approved
0.7133	Intermediate Similarity	NPD825	Approved
0.7132	Intermediate Similarity	NPD1792	Phase 2
0.7124	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3455	Phase 2
0.7123	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1817	Approved
0.7122	Intermediate Similarity	NPD1818	Approved
0.7122	Intermediate Similarity	NPD1819	Approved
0.7122	Intermediate Similarity	NPD1820	Approved
0.7121	Intermediate Similarity	NPD1793	Approved
0.7121	Intermediate Similarity	NPD595	Approved
0.7121	Intermediate Similarity	NPD1791	Approved
0.7121	Intermediate Similarity	NPD593	Approved
0.7121	Intermediate Similarity	NPD9614	Approved
0.7121	Intermediate Similarity	NPD9618	Approved
0.7114	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1048	Approved
0.7111	Intermediate Similarity	NPD4093	Discontinued
0.7107	Intermediate Similarity	NPD2821	Approved
0.7105	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6031	Approved
0.7105	Intermediate Similarity	NPD6030	Approved
0.7092	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9616	Approved
0.709	Intermediate Similarity	NPD9613	Approved
0.709	Intermediate Similarity	NPD9615	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