NPASS Compound

Structure

NPC11821 OpenBabel07101718322D 23 23 0 0 0 0 0 0 0 0999 V2000 1.5292 3.6917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5237 3.7962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9305 4.7098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3427 5.5188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3482 5.4143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7604 6.2233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2341 6.1187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6409 5.2052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6354 5.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0421 4.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4543 3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8611 2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2733 1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -0.0000 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 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 -3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 -1.5878 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 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 16 19 2 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	353.835
LogP:	1.904
LogD:	2.621
LogS:	-3.116
# Rotatable Bonds:	11
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.567
Synthetic Accessibility Score:	3.189
Fsp3:	0.35
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:	-4.98
MDCK Permeability:	0.00011126744357170537
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	100.46855926513672%
Volume Distribution (VD):	0.852
Pgp-substrate:	0.5232419371604919%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.406
CYP2C19-substrate:	0.395
CYP2C9-inhibitor:	0.757
CYP2C9-substrate:	0.992
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.194
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	2.633
Half-life (T1/2):	0.944

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.97
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.154
Skin Sensitization:	0.883
Carcinogencity:	0.897
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.633

Download Data

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

Natural Product: NPC11821

Natural Product ID:	NPC11821
*Common Name:**	(8Z,11Z,14Z,17Z)-3,6-Epoxyeicos-3,5,8,11,14,17-Hexenoic Acid
IUPAC Name:	2-[5-[(2Z,5Z,8Z,11Z)-tetradeca-2,5,8,11-tetraenyl]furan-2-yl]acetic acid
Synonyms:
Standard InCHIKey:	ASCYUTAWNJPWQT-LTKCOYKYSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-15-16-19(23-18)17-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-
SMILES:	CC/C=CC/C=CC/C=CC/C=CCc1ccc(o1)CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513746
PubChem CID:	10358283
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0001989] Heterocyclic fatty acids [CHEMONTID:0001528] Furanoid fatty acids

*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
NPO23934	Hymeniacidon hauraki	Species	Halichondriidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[7853004]
NPO23934	Hymeniacidon hauraki	Species	Halichondriidae	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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	13.4	ug.mL-1	PMID[540364]
NPT27	Others	Unspecified		Activity	=	2.0	mm	PMID[540364]

☑ 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 NPC11821 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	253
0.1-0.2	2053
0.2-0.3	5653
0.3-0.4	11524
0.4-0.5	7778
0.5-0.6	8912
0.6-0.7	6088
0.7-0.8	414
0.8-0.85	13
0.85-0.9	4
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC76844
0.887	High Similarity	NPC254958
0.887	High Similarity	NPC291619
0.8696	High Similarity	NPC476014
0.8696	High Similarity	NPC476031
0.8534	High Similarity	NPC474987
0.8468	Intermediate Similarity	NPC42471
0.839	Intermediate Similarity	NPC21831
0.839	Intermediate Similarity	NPC187547
0.8362	Intermediate Similarity	NPC292036
0.8281	Intermediate Similarity	NPC159786
0.8131	Intermediate Similarity	NPC233791
0.813	Intermediate Similarity	NPC118853
0.8115	Intermediate Similarity	NPC270807
0.8115	Intermediate Similarity	NPC174915
0.811	Intermediate Similarity	NPC136340
0.8018	Intermediate Similarity	NPC156768
0.8017	Intermediate Similarity	NPC67345
0.8017	Intermediate Similarity	NPC244862
0.8	Intermediate Similarity	NPC144745
0.8	Intermediate Similarity	NPC208906
0.7983	Intermediate Similarity	NPC205523
0.7982	Intermediate Similarity	NPC298087
0.7967	Intermediate Similarity	NPC323118
0.7923	Intermediate Similarity	NPC106247
0.7917	Intermediate Similarity	NPC328451
0.7903	Intermediate Similarity	NPC311219
0.7895	Intermediate Similarity	NPC107571
0.7851	Intermediate Similarity	NPC312525
0.7851	Intermediate Similarity	NPC227660
0.7851	Intermediate Similarity	NPC217180
0.7823	Intermediate Similarity	NPC272487
0.7794	Intermediate Similarity	NPC254198
0.7778	Intermediate Similarity	NPC474829
0.7744	Intermediate Similarity	NPC473268
0.7742	Intermediate Similarity	NPC79557
0.7731	Intermediate Similarity	NPC1811
0.7731	Intermediate Similarity	NPC26157
0.7724	Intermediate Similarity	NPC473969
0.7717	Intermediate Similarity	NPC81912
0.7717	Intermediate Similarity	NPC329694
0.7717	Intermediate Similarity	NPC216810
0.7717	Intermediate Similarity	NPC474260
0.7717	Intermediate Similarity	NPC329922
0.7698	Intermediate Similarity	NPC243269
0.7669	Intermediate Similarity	NPC303217
0.7661	Intermediate Similarity	NPC474874
0.7661	Intermediate Similarity	NPC230951
0.7661	Intermediate Similarity	NPC470092
0.7658	Intermediate Similarity	NPC146316
0.7656	Intermediate Similarity	NPC474830
0.7647	Intermediate Similarity	NPC105249
0.7638	Intermediate Similarity	NPC75557
0.7638	Intermediate Similarity	NPC71274
0.7638	Intermediate Similarity	NPC221798
0.7634	Intermediate Similarity	NPC473982
0.763	Intermediate Similarity	NPC474615
0.763	Intermediate Similarity	NPC202260
0.7626	Intermediate Similarity	NPC104924
0.7623	Intermediate Similarity	NPC470860
0.7623	Intermediate Similarity	NPC45536
0.7619	Intermediate Similarity	NPC476351
0.7612	Intermediate Similarity	NPC170604
0.7612	Intermediate Similarity	NPC215109
0.76	Intermediate Similarity	NPC1848
0.7597	Intermediate Similarity	NPC474438
0.7597	Intermediate Similarity	NPC474279
0.7581	Intermediate Similarity	NPC244293
0.7576	Intermediate Similarity	NPC474425
0.7576	Intermediate Similarity	NPC474407
0.7576	Intermediate Similarity	NPC474426
0.7574	Intermediate Similarity	NPC148374
0.7571	Intermediate Similarity	NPC308799
0.7563	Intermediate Similarity	NPC229387
0.7561	Intermediate Similarity	NPC217423
0.7561	Intermediate Similarity	NPC131801
0.7559	Intermediate Similarity	NPC188377
0.7559	Intermediate Similarity	NPC65735
0.7557	Intermediate Similarity	NPC475092
0.7557	Intermediate Similarity	NPC183348
0.7557	Intermediate Similarity	NPC282230
0.7556	Intermediate Similarity	NPC472376
0.7542	Intermediate Similarity	NPC473356
0.7542	Intermediate Similarity	NPC471521
0.7541	Intermediate Similarity	NPC28054
0.7541	Intermediate Similarity	NPC188907
0.754	Intermediate Similarity	NPC263870
0.7521	Intermediate Similarity	NPC311987
0.7519	Intermediate Similarity	NPC477536
0.7519	Intermediate Similarity	NPC476016
0.7518	Intermediate Similarity	NPC113428
0.7518	Intermediate Similarity	NPC61284
0.75	Intermediate Similarity	NPC293424
0.75	Intermediate Similarity	NPC193805
0.75	Intermediate Similarity	NPC15083
0.75	Intermediate Similarity	NPC324488
0.75	Intermediate Similarity	NPC470977
0.75	Intermediate Similarity	NPC196979
0.75	Intermediate Similarity	NPC471559
0.75	Intermediate Similarity	NPC470976
0.7481	Intermediate Similarity	NPC66246
0.7481	Intermediate Similarity	NPC170546
0.7481	Intermediate Similarity	NPC187907
0.7481	Intermediate Similarity	NPC473019
0.7481	Intermediate Similarity	NPC238309
0.748	Intermediate Similarity	NPC69403
0.748	Intermediate Similarity	NPC475818
0.748	Intermediate Similarity	NPC291189
0.7479	Intermediate Similarity	NPC177331
0.746	Intermediate Similarity	NPC474136
0.7458	Intermediate Similarity	NPC219969
0.7445	Intermediate Similarity	NPC282973
0.7444	Intermediate Similarity	NPC470740
0.7442	Intermediate Similarity	NPC138139
0.7442	Intermediate Similarity	NPC4164
0.7442	Intermediate Similarity	NPC46536
0.744	Intermediate Similarity	NPC328459
0.744	Intermediate Similarity	NPC90522
0.744	Intermediate Similarity	NPC54243
0.744	Intermediate Similarity	NPC4898
0.744	Intermediate Similarity	NPC264976
0.7438	Intermediate Similarity	NPC22678
0.7426	Intermediate Similarity	NPC477534
0.7424	Intermediate Similarity	NPC477645
0.7422	Intermediate Similarity	NPC93730
0.7419	Intermediate Similarity	NPC240664
0.7407	Intermediate Similarity	NPC204592
0.7402	Intermediate Similarity	NPC473379
0.7402	Intermediate Similarity	NPC283284
0.7402	Intermediate Similarity	NPC471549
0.7402	Intermediate Similarity	NPC289911
0.7398	Intermediate Similarity	NPC51345
0.7388	Intermediate Similarity	NPC287533
0.7385	Intermediate Similarity	NPC473355
0.7385	Intermediate Similarity	NPC474476
0.7385	Intermediate Similarity	NPC83178
0.7385	Intermediate Similarity	NPC471573
0.7385	Intermediate Similarity	NPC471554
0.7385	Intermediate Similarity	NPC319140
0.7385	Intermediate Similarity	NPC471501
0.7385	Intermediate Similarity	NPC95567
0.7385	Intermediate Similarity	NPC184391
0.7381	Intermediate Similarity	NPC474817
0.7381	Intermediate Similarity	NPC246214
0.7381	Intermediate Similarity	NPC72977
0.7364	Intermediate Similarity	NPC473885
0.7364	Intermediate Similarity	NPC471074
0.736	Intermediate Similarity	NPC94637
0.736	Intermediate Similarity	NPC243704
0.736	Intermediate Similarity	NPC32298
0.736	Intermediate Similarity	NPC206007
0.7353	Intermediate Similarity	NPC307401
0.7348	Intermediate Similarity	NPC939
0.7339	Intermediate Similarity	NPC128825
0.7339	Intermediate Similarity	NPC33717
0.7333	Intermediate Similarity	NPC209111
0.7333	Intermediate Similarity	NPC259554
0.7333	Intermediate Similarity	NPC234639
0.7333	Intermediate Similarity	NPC265793
0.7328	Intermediate Similarity	NPC207294
0.7328	Intermediate Similarity	NPC329707
0.7328	Intermediate Similarity	NPC112706
0.7328	Intermediate Similarity	NPC217226
0.7319	Intermediate Similarity	NPC473988
0.731	Intermediate Similarity	NPC474219
0.731	Intermediate Similarity	NPC474378
0.7308	Intermediate Similarity	NPC52035
0.7305	Intermediate Similarity	NPC105381
0.7305	Intermediate Similarity	NPC195920
0.7305	Intermediate Similarity	NPC37488
0.7305	Intermediate Similarity	NPC10302
0.7302	Intermediate Similarity	NPC137710
0.7302	Intermediate Similarity	NPC61779
0.7302	Intermediate Similarity	NPC35744
0.7293	Intermediate Similarity	NPC327457
0.7293	Intermediate Similarity	NPC86774
0.7293	Intermediate Similarity	NPC17681
0.7286	Intermediate Similarity	NPC22248
0.7286	Intermediate Similarity	NPC110305
0.728	Intermediate Similarity	NPC107482
0.728	Intermediate Similarity	NPC45104
0.7279	Intermediate Similarity	NPC298900
0.7279	Intermediate Similarity	NPC474542
0.7279	Intermediate Similarity	NPC66705
0.7273	Intermediate Similarity	NPC2596
0.7266	Intermediate Similarity	NPC477967
0.7266	Intermediate Similarity	NPC477537
0.7254	Intermediate Similarity	NPC475864
0.7252	Intermediate Similarity	NPC141059
0.7252	Intermediate Similarity	NPC475236
0.7246	Intermediate Similarity	NPC332594
0.7246	Intermediate Similarity	NPC62735
0.7239	Intermediate Similarity	NPC97740
0.7239	Intermediate Similarity	NPC45358
0.7239	Intermediate Similarity	NPC125153
0.7234	Intermediate Similarity	NPC261733
0.7234	Intermediate Similarity	NPC307346
0.7234	Intermediate Similarity	NPC267004
0.7234	Intermediate Similarity	NPC218712
0.7231	Intermediate Similarity	NPC89630

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 NPC11821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	1054
0.2-0.3	2062
0.3-0.4	2840
0.4-0.5	1873
0.5-0.6	837
0.6-0.7	220
0.7-0.8	25
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
0.7903	Intermediate Similarity	NPD9717	Approved
0.7578	Intermediate Similarity	NPD1203	Approved
0.7538	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD2344	Approved
0.7481	Intermediate Similarity	NPD2799	Discontinued
0.7424	Intermediate Similarity	NPD2313	Discontinued
0.7372	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD9493	Approved
0.7308	Intermediate Similarity	NPD2797	Approved
0.7293	Intermediate Similarity	NPD411	Approved
0.7286	Intermediate Similarity	NPD2309	Approved
0.728	Intermediate Similarity	NPD9092	Discovery
0.7259	Intermediate Similarity	NPD447	Suspended
0.7252	Intermediate Similarity	NPD5647	Approved
0.7252	Intermediate Similarity	NPD1019	Discontinued
0.7252	Intermediate Similarity	NPD2798	Approved
0.7236	Intermediate Similarity	NPD1241	Discontinued
0.7164	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD1243	Approved
0.7132	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2346	Discontinued
0.7101	Intermediate Similarity	NPD4308	Phase 3
0.7063	Intermediate Similarity	NPD6799	Approved
0.705	Intermediate Similarity	NPD2935	Discontinued
0.7021	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1933	Approved
0.7	Intermediate Similarity	NPD1471	Phase 3
0.6953	Remote Similarity	NPD9545	Approved
0.6953	Remote Similarity	NPD1894	Discontinued
0.6947	Remote Similarity	NPD1608	Approved
0.6947	Remote Similarity	NPD3972	Approved
0.6934	Remote Similarity	NPD4307	Phase 2
0.6929	Remote Similarity	NPD1551	Phase 2
0.6917	Remote Similarity	NPD3266	Approved
0.6917	Remote Similarity	NPD6362	Approved
0.6917	Remote Similarity	NPD3267	Approved
0.6885	Remote Similarity	NPD9263	Approved
0.6885	Remote Similarity	NPD9264	Approved
0.6885	Remote Similarity	NPD9267	Approved
0.6875	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4628	Phase 3
0.6853	Remote Similarity	NPD3750	Approved
0.6853	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7411	Suspended
0.6842	Remote Similarity	NPD1876	Approved
0.6842	Remote Similarity	NPD3749	Approved
0.6829	Remote Similarity	NPD74	Approved
0.6829	Remote Similarity	NPD9266	Approved
0.6818	Remote Similarity	NPD1481	Phase 2
0.6812	Remote Similarity	NPD1240	Approved
0.6809	Remote Similarity	NPD2796	Approved
0.6806	Remote Similarity	NPD2354	Approved
0.6803	Remote Similarity	NPD3134	Approved
0.6803	Remote Similarity	NPD920	Approved
0.6803	Remote Similarity	NPD5403	Approved
0.6791	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5401	Approved
0.6779	Remote Similarity	NPD6599	Discontinued
0.6755	Remote Similarity	NPD7819	Suspended
0.6755	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1535	Discovery
0.6739	Remote Similarity	NPD6233	Phase 2
0.6738	Remote Similarity	NPD3748	Approved
0.6738	Remote Similarity	NPD7033	Discontinued
0.6735	Remote Similarity	NPD6273	Approved
0.6721	Remote Similarity	NPD9697	Approved
0.6718	Remote Similarity	NPD1778	Approved
0.6718	Remote Similarity	NPD17	Approved
0.6716	Remote Similarity	NPD3225	Approved
0.6715	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1607	Approved
0.6713	Remote Similarity	NPD1549	Phase 2
0.6711	Remote Similarity	NPD3226	Approved
0.6711	Remote Similarity	NPD2296	Approved
0.6694	Remote Similarity	NPD9261	Approved
0.6691	Remote Similarity	NPD3140	Approved
0.6691	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6808	Phase 2
0.6644	Remote Similarity	NPD7440	Discontinued
0.6643	Remote Similarity	NPD6355	Discontinued
0.6643	Remote Similarity	NPD2353	Approved
0.6643	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2614	Approved
0.6641	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7075	Discontinued
0.6622	Remote Similarity	NPD5049	Phase 3
0.6619	Remote Similarity	NPD4062	Phase 3
0.6617	Remote Similarity	NPD422	Phase 1
0.6614	Remote Similarity	NPD5535	Approved
0.6613	Remote Similarity	NPD1358	Approved
0.6597	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6279	Approved
0.6579	Remote Similarity	NPD6280	Approved
0.6579	Remote Similarity	NPD6801	Discontinued
0.6575	Remote Similarity	NPD3887	Approved
0.6569	Remote Similarity	NPD454	Approved
0.6562	Remote Similarity	NPD9069	Phase 1
0.656	Remote Similarity	NPD2182	Approved
0.6558	Remote Similarity	NPD7768	Phase 2
0.6558	Remote Similarity	NPD3882	Suspended
0.6554	Remote Similarity	NPD4662	Approved
0.6554	Remote Similarity	NPD4661	Approved
0.6552	Remote Similarity	NPD2800	Approved
0.6541	Remote Similarity	NPD3847	Discontinued
0.6528	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6005	Phase 3
0.6528	Remote Similarity	NPD6004	Phase 3
0.6528	Remote Similarity	NPD6002	Phase 3
0.6528	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5585	Approved
0.6512	Remote Similarity	NPD9281	Approved
0.6507	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7003	Approved
0.6507	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1510	Phase 2
0.65	Remote Similarity	NPD8032	Phase 2
0.6494	Remote Similarity	NPD3817	Phase 2
0.6494	Remote Similarity	NPD5402	Approved
0.649	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.648	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD6653	Approved
0.6474	Remote Similarity	NPD919	Approved
0.6471	Remote Similarity	NPD1283	Approved
0.6467	Remote Similarity	NPD3869	Phase 3
0.6467	Remote Similarity	NPD3873	Phase 3
0.6458	Remote Similarity	NPD4477	Approved
0.6458	Remote Similarity	NPD4476	Approved
0.6447	Remote Similarity	NPD6585	Discontinued
0.6446	Remote Similarity	NPD1238	Approved
0.6443	Remote Similarity	NPD2532	Approved
0.6443	Remote Similarity	NPD2534	Approved
0.6443	Remote Similarity	NPD2533	Approved
0.6442	Remote Similarity	NPD6559	Discontinued
0.6429	Remote Similarity	NPD2684	Approved
0.641	Remote Similarity	NPD9365	Approved
0.6405	Remote Similarity	NPD5890	Approved
0.6405	Remote Similarity	NPD2366	Approved
0.6405	Remote Similarity	NPD5889	Approved
0.6398	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD1511	Approved
0.6375	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD164	Approved
0.6364	Remote Similarity	NPD6844	Discontinued
0.6358	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD7095	Approved
0.6349	Remote Similarity	NPD290	Approved
0.6347	Remote Similarity	NPD8434	Phase 2
0.6345	Remote Similarity	NPD5712	Approved
0.6343	Remote Similarity	NPD4626	Approved
0.6341	Remote Similarity	NPD291	Approved
0.6331	Remote Similarity	NPD9494	Approved
0.6327	Remote Similarity	NPD2654	Approved
0.6325	Remote Similarity	NPD9256	Approved
0.6325	Remote Similarity	NPD9258	Approved
0.6323	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD2801	Approved
0.6312	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD1296	Phase 2
0.6312	Remote Similarity	NPD3926	Phase 2
0.6306	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1164	Approved
0.6301	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4618	Approved
0.6294	Remote Similarity	NPD4622	Approved
0.6294	Remote Similarity	NPD1184	Approved
0.6291	Remote Similarity	NPD1512	Approved
0.6288	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4110	Phase 3
0.6284	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4359	Approved
0.6277	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7458	Discontinued
0.6269	Remote Similarity	NPD5691	Approved
0.6266	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD5958	Discontinued
0.6259	Remote Similarity	NPD4534	Discontinued
0.6258	Remote Similarity	NPD1934	Approved
0.625	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1281	Approved
0.625	Remote Similarity	NPD1670	Discontinued
0.6242	Remote Similarity	NPD6764	Approved
0.6242	Remote Similarity	NPD6765	Approved
0.6241	Remote Similarity	NPD5536	Phase 2

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