NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.17
Volume:	286.691
LogP:	2.185
LogD:	3.272
LogS:	-3.959
# Rotatable Bonds:	6
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	3.026
Fsp3:	0.733
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:	-5.774
MDCK Permeability:	9.938092262018472e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.597
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	95.01339721679688%
Volume Distribution (VD):	0.515
Pgp-substrate:	2.1964871883392334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.029

ADMET: Excretion

Clearance (CL):	0.689
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.539
Carcinogencity:	0.025
Eye Corrosion:	0.709
Eye Irritation:	0.536
Respiratory Toxicity:	0.093

Download Data

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

Natural Product: NPC234767

Natural Product ID:	NPC234767
*Common Name:**	Hymenoic Acid
IUPAC Name:	n.a.
Synonyms:	Hymenoic acid
Standard InCHIKey:	LTNNRLSIPOPBOC-YKOULDITSA-N
Standard InCHI:	InChI=1S/C15H24O4/c1-10(4-3-5-11(2)14(16)17)12-6-8-13(9-7-12)15(18)19/h4,11-13H,3,5-9H2,1-2H3,(H,16,17)(H,18,19)/b10-4+/t11-,12-,13-/m0/s1
SMILES:	C/C(=CCC[C@H](C)C(=O)O)/[C@H]1CC[C@@H](CC1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494213
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33121	hymenochaetaceae sp.	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18364258]

☑ 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	4
Others	6

Activity Type	# Activity
Individual Protein	8
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	Vmax	=	48.8	uM	PMID[514842]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	Vmax	=	62.5	uM	PMID[514842]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	Vmax	=	40.8	uM	PMID[514842]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	Vmax	=	40.0	uM	PMID[514842]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	Vmax	=	32.3	uM	PMID[514842]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	Vmax	=	27.0	uM	PMID[514842]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	IC50	<	100000.0	nM	PMID[514842]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	IC50	>	200000.0	nM	PMID[514842]
NPT2	Others	Unspecified		IC50	>	200000.0	nM	PMID[514842]

☑ 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 NPC234767 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	130
0.1-0.2	1094
0.2-0.3	6533
0.3-0.4	16922
0.4-0.5	8417
0.5-0.6	6932
0.6-0.7	2308
0.7-0.8	337
0.8-0.85	18
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8529	High Similarity	NPC35656
0.8382	Intermediate Similarity	NPC160817
0.8333	Intermediate Similarity	NPC472875
0.8286	Intermediate Similarity	NPC192540
0.8286	Intermediate Similarity	NPC279666
0.8286	Intermediate Similarity	NPC476795
0.8194	Intermediate Similarity	NPC321514
0.8194	Intermediate Similarity	NPC110094
0.8194	Intermediate Similarity	NPC280654
0.8194	Intermediate Similarity	NPC260385
0.8182	Intermediate Similarity	NPC322035
0.8182	Intermediate Similarity	NPC100719
0.8182	Intermediate Similarity	NPC166791
0.8169	Intermediate Similarity	NPC180886
0.8169	Intermediate Similarity	NPC69143
0.8169	Intermediate Similarity	NPC309399
0.8143	Intermediate Similarity	NPC103958
0.8143	Intermediate Similarity	NPC251970
0.8143	Intermediate Similarity	NPC3753
0.8143	Intermediate Similarity	NPC241854
0.8143	Intermediate Similarity	NPC183503
0.8143	Intermediate Similarity	NPC283908
0.8143	Intermediate Similarity	NPC237591
0.8143	Intermediate Similarity	NPC301065
0.8143	Intermediate Similarity	NPC161923
0.8143	Intermediate Similarity	NPC476046
0.8125	Intermediate Similarity	NPC174560
0.8125	Intermediate Similarity	NPC125312
0.8082	Intermediate Similarity	NPC199595
0.8082	Intermediate Similarity	NPC327674
0.8056	Intermediate Similarity	NPC471899
0.8056	Intermediate Similarity	NPC471897
0.8056	Intermediate Similarity	NPC61952
0.8056	Intermediate Similarity	NPC107039
0.8028	Intermediate Similarity	NPC476844
0.8028	Intermediate Similarity	NPC472327
0.7973	Intermediate Similarity	NPC37038
0.7973	Intermediate Similarity	NPC104545
0.7945	Intermediate Similarity	NPC179028
0.7945	Intermediate Similarity	NPC74410
0.7945	Intermediate Similarity	NPC198240
0.7941	Intermediate Similarity	NPC290445
0.7941	Intermediate Similarity	NPC36616
0.7917	Intermediate Similarity	NPC89294
0.7867	Intermediate Similarity	NPC221647
0.7867	Intermediate Similarity	NPC327002
0.7867	Intermediate Similarity	NPC278459
0.7838	Intermediate Similarity	NPC274996
0.7838	Intermediate Similarity	NPC231431
0.7838	Intermediate Similarity	NPC477371
0.7838	Intermediate Similarity	NPC16394
0.7838	Intermediate Similarity	NPC196827
0.7838	Intermediate Similarity	NPC158846
0.7833	Intermediate Similarity	NPC281245
0.7826	Intermediate Similarity	NPC67608
0.7808	Intermediate Similarity	NPC165711
0.7808	Intermediate Similarity	NPC97377
0.7778	Intermediate Similarity	NPC201027
0.7763	Intermediate Similarity	NPC133391
0.7733	Intermediate Similarity	NPC477057
0.7714	Intermediate Similarity	NPC235586
0.7705	Intermediate Similarity	NPC36061
0.7705	Intermediate Similarity	NPC294548
0.7705	Intermediate Similarity	NPC139029
0.7705	Intermediate Similarity	NPC1813
0.7703	Intermediate Similarity	NPC59436
0.7703	Intermediate Similarity	NPC239098
0.7703	Intermediate Similarity	NPC169095
0.7681	Intermediate Similarity	NPC476614
0.7681	Intermediate Similarity	NPC53302
0.7671	Intermediate Similarity	NPC469514
0.7662	Intermediate Similarity	NPC200752
0.7662	Intermediate Similarity	NPC167103
0.7662	Intermediate Similarity	NPC97913
0.7662	Intermediate Similarity	NPC477373
0.7656	Intermediate Similarity	NPC329819
0.7647	Intermediate Similarity	NPC142423
0.7647	Intermediate Similarity	NPC308294
0.7639	Intermediate Similarity	NPC472966
0.7639	Intermediate Similarity	NPC55527
0.7639	Intermediate Similarity	NPC213223
0.7632	Intermediate Similarity	NPC90055
0.7632	Intermediate Similarity	NPC162632
0.7632	Intermediate Similarity	NPC477372
0.7632	Intermediate Similarity	NPC147066
0.7632	Intermediate Similarity	NPC473420
0.7632	Intermediate Similarity	NPC40228
0.7632	Intermediate Similarity	NPC229584
0.7632	Intermediate Similarity	NPC38350
0.7632	Intermediate Similarity	NPC142244
0.7632	Intermediate Similarity	NPC471898
0.7632	Intermediate Similarity	NPC274050
0.7632	Intermediate Similarity	NPC201912
0.7632	Intermediate Similarity	NPC263272
0.7632	Intermediate Similarity	NPC14203
0.7632	Intermediate Similarity	NPC267691
0.7612	Intermediate Similarity	NPC53642
0.7612	Intermediate Similarity	NPC470325
0.7606	Intermediate Similarity	NPC288667
0.76	Intermediate Similarity	NPC308545
0.76	Intermediate Similarity	NPC82488
0.7581	Intermediate Similarity	NPC88966
0.7581	Intermediate Similarity	NPC87564
0.7581	Intermediate Similarity	NPC154245
0.7581	Intermediate Similarity	NPC281972
0.7581	Intermediate Similarity	NPC6095
0.7581	Intermediate Similarity	NPC261831
0.7581	Intermediate Similarity	NPC85813
0.7581	Intermediate Similarity	NPC290563
0.7581	Intermediate Similarity	NPC25417
0.7581	Intermediate Similarity	NPC424
0.7581	Intermediate Similarity	NPC32467
0.7571	Intermediate Similarity	NPC469914
0.7564	Intermediate Similarity	NPC472864
0.7564	Intermediate Similarity	NPC164577
0.7564	Intermediate Similarity	NPC96095
0.7564	Intermediate Similarity	NPC19849
0.7564	Intermediate Similarity	NPC472865
0.7564	Intermediate Similarity	NPC248758
0.7564	Intermediate Similarity	NPC156981
0.7541	Intermediate Similarity	NPC216407
0.7536	Intermediate Similarity	NPC476626
0.7536	Intermediate Similarity	NPC60120
0.7536	Intermediate Similarity	NPC278895
0.7534	Intermediate Similarity	NPC60718
0.7534	Intermediate Similarity	NPC199445
0.7532	Intermediate Similarity	NPC260956
0.7532	Intermediate Similarity	NPC296367
0.7532	Intermediate Similarity	NPC69101
0.7532	Intermediate Similarity	NPC251779
0.75	Intermediate Similarity	NPC271104
0.75	Intermediate Similarity	NPC103634
0.75	Intermediate Similarity	NPC244708
0.75	Intermediate Similarity	NPC330659
0.75	Intermediate Similarity	NPC36310
0.75	Intermediate Similarity	NPC321017
0.75	Intermediate Similarity	NPC161187
0.7468	Intermediate Similarity	NPC269638
0.7468	Intermediate Similarity	NPC142649
0.7467	Intermediate Similarity	NPC121200
0.7465	Intermediate Similarity	NPC67183
0.7465	Intermediate Similarity	NPC91369
0.7436	Intermediate Similarity	NPC310470
0.7436	Intermediate Similarity	NPC70834
0.7436	Intermediate Similarity	NPC49019
0.7436	Intermediate Similarity	NPC83569
0.7436	Intermediate Similarity	NPC69279
0.7436	Intermediate Similarity	NPC215893
0.7436	Intermediate Similarity	NPC105803
0.7432	Intermediate Similarity	NPC899
0.7432	Intermediate Similarity	NPC186554
0.7432	Intermediate Similarity	NPC472305
0.7432	Intermediate Similarity	NPC246445
0.7432	Intermediate Similarity	NPC76966
0.7432	Intermediate Similarity	NPC61863
0.7419	Intermediate Similarity	NPC321062
0.7419	Intermediate Similarity	NPC70387
0.7403	Intermediate Similarity	NPC14044
0.7403	Intermediate Similarity	NPC117960
0.7403	Intermediate Similarity	NPC172309
0.7397	Intermediate Similarity	NPC166797
0.7397	Intermediate Similarity	NPC255168
0.7397	Intermediate Similarity	NPC46610
0.7397	Intermediate Similarity	NPC306928
0.7397	Intermediate Similarity	NPC18819
0.7391	Intermediate Similarity	NPC197089
0.7391	Intermediate Similarity	NPC103734
0.7377	Intermediate Similarity	NPC48162
0.7375	Intermediate Similarity	NPC262085
0.7375	Intermediate Similarity	NPC73038
0.7375	Intermediate Similarity	NPC186975
0.7375	Intermediate Similarity	NPC473226
0.7375	Intermediate Similarity	NPC324063
0.7375	Intermediate Similarity	NPC472869
0.7368	Intermediate Similarity	NPC192329
0.7368	Intermediate Similarity	NPC28319
0.7368	Intermediate Similarity	NPC113363
0.7361	Intermediate Similarity	NPC29328
0.7361	Intermediate Similarity	NPC72343
0.7344	Intermediate Similarity	NPC18951
0.7344	Intermediate Similarity	NPC477201
0.7344	Intermediate Similarity	NPC179764
0.7344	Intermediate Similarity	NPC187777
0.7342	Intermediate Similarity	NPC477289
0.7342	Intermediate Similarity	NPC476038
0.7342	Intermediate Similarity	NPC165064
0.7342	Intermediate Similarity	NPC194937
0.7333	Intermediate Similarity	NPC472014
0.7333	Intermediate Similarity	NPC34110
0.7333	Intermediate Similarity	NPC197659
0.7333	Intermediate Similarity	NPC281296
0.7333	Intermediate Similarity	NPC266193
0.7333	Intermediate Similarity	NPC257666
0.7333	Intermediate Similarity	NPC238227
0.7333	Intermediate Similarity	NPC472300
0.7333	Intermediate Similarity	NPC316324
0.7308	Intermediate Similarity	NPC238991
0.7308	Intermediate Similarity	NPC73882
0.7308	Intermediate Similarity	NPC302661
0.7308	Intermediate Similarity	NPC320514

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 NPC234767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	110
0.1-0.2	1641
0.2-0.3	4014
0.3-0.4	2260
0.4-0.5	680
0.5-0.6	322
0.6-0.7	113
0.7-0.8	10
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
0.7705	Intermediate Similarity	NPD3172	Approved
0.7581	Intermediate Similarity	NPD3196	Approved
0.7581	Intermediate Similarity	NPD3194	Approved
0.7581	Intermediate Similarity	NPD4266	Approved
0.7581	Intermediate Similarity	NPD3195	Phase 2
0.7391	Intermediate Similarity	NPD7331	Phase 2
0.7302	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7341	Phase 2
0.7167	Intermediate Similarity	NPD622	Approved
0.7119	Intermediate Similarity	NPD634	Phase 3
0.7097	Intermediate Similarity	NPD29	Approved
0.7097	Intermediate Similarity	NPD28	Approved
0.7051	Intermediate Similarity	NPD4695	Discontinued
0.7049	Intermediate Similarity	NPD3173	Approved
0.6962	Remote Similarity	NPD857	Phase 3
0.6941	Remote Similarity	NPD5281	Approved
0.6941	Remote Similarity	NPD5284	Approved
0.6941	Remote Similarity	NPD7515	Phase 2
0.6905	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4223	Phase 3
0.6875	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3667	Approved
0.6875	Remote Similarity	NPD4221	Approved
0.686	Remote Similarity	NPD6399	Phase 3
0.6835	Remote Similarity	NPD5368	Approved
0.6795	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5362	Discontinued
0.679	Remote Similarity	NPD7154	Phase 3
0.6782	Remote Similarity	NPD7748	Approved
0.675	Remote Similarity	NPD5369	Approved
0.6714	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4786	Approved
0.6707	Remote Similarity	NPD3665	Phase 1
0.6707	Remote Similarity	NPD3666	Approved
0.6707	Remote Similarity	NPD3133	Approved
0.6707	Remote Similarity	NPD4197	Approved
0.6706	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6101	Approved
0.6706	Remote Similarity	NPD800	Approved
0.6705	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD342	Phase 1
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6628	Remote Similarity	NPD1090	Approved
0.6628	Remote Similarity	NPD1089	Approved
0.6628	Remote Similarity	NPD1086	Approved
0.6627	Remote Similarity	NPD5329	Approved
0.6623	Remote Similarity	NPD8039	Approved
0.662	Remote Similarity	NPD3197	Phase 1
0.6588	Remote Similarity	NPD6672	Approved
0.6588	Remote Similarity	NPD5737	Approved
0.6582	Remote Similarity	NPD3617	Approved
0.6557	Remote Similarity	NPD3174	Discontinued
0.6557	Remote Similarity	NPD4222	Approved
0.6556	Remote Similarity	NPD6084	Phase 2
0.6556	Remote Similarity	NPD7902	Approved
0.6556	Remote Similarity	NPD6083	Phase 2
0.6552	Remote Similarity	NPD6411	Approved
0.6548	Remote Similarity	NPD4694	Approved
0.6548	Remote Similarity	NPD6684	Approved
0.6548	Remote Similarity	NPD4138	Approved
0.6548	Remote Similarity	NPD4693	Phase 3
0.6548	Remote Similarity	NPD4519	Discontinued
0.6548	Remote Similarity	NPD7521	Approved
0.6548	Remote Similarity	NPD3618	Phase 1
0.6548	Remote Similarity	NPD5690	Phase 2
0.6548	Remote Similarity	NPD6409	Approved
0.6548	Remote Similarity	NPD6422	Discontinued
0.6548	Remote Similarity	NPD5280	Approved
0.6548	Remote Similarity	NPD4689	Approved
0.6548	Remote Similarity	NPD6098	Approved
0.6548	Remote Similarity	NPD7334	Approved
0.6548	Remote Similarity	NPD4688	Approved
0.6548	Remote Similarity	NPD5205	Approved
0.6548	Remote Similarity	NPD4623	Approved
0.6548	Remote Similarity	NPD4690	Approved
0.6548	Remote Similarity	NPD5330	Approved
0.6548	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7146	Approved
0.6543	Remote Similarity	NPD226	Approved
0.6512	Remote Similarity	NPD6673	Approved
0.6512	Remote Similarity	NPD5347	Phase 2
0.6512	Remote Similarity	NPD6080	Approved
0.6512	Remote Similarity	NPD4753	Phase 2
0.6512	Remote Similarity	NPD5346	Phase 2
0.6512	Remote Similarity	NPD6904	Approved
0.6506	Remote Similarity	NPD3668	Phase 3
0.6484	Remote Similarity	NPD5696	Approved
0.6477	Remote Similarity	NPD5778	Approved
0.6477	Remote Similarity	NPD5779	Approved
0.6477	Remote Similarity	NPD1088	Approved
0.6471	Remote Similarity	NPD3573	Approved
0.6462	Remote Similarity	NPD3186	Phase 1
0.6456	Remote Similarity	NPD4756	Discovery
0.6444	Remote Similarity	NPD7614	Phase 1
0.6437	Remote Similarity	NPD46	Approved
0.6437	Remote Similarity	NPD5692	Phase 3
0.6437	Remote Similarity	NPD6698	Approved
0.6429	Remote Similarity	NPD1694	Approved
0.6429	Remote Similarity	NPD5363	Approved
0.6429	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4252	Approved
0.642	Remote Similarity	NPD4821	Approved
0.642	Remote Similarity	NPD4819	Approved
0.642	Remote Similarity	NPD4820	Approved
0.642	Remote Similarity	NPD4822	Approved
0.6404	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6903	Approved
0.6395	Remote Similarity	NPD5208	Approved
0.6395	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5331	Approved
0.6386	Remote Similarity	NPD5332	Approved
0.6375	Remote Similarity	NPD4271	Approved
0.6375	Remote Similarity	NPD4268	Approved
0.6375	Remote Similarity	NPD3732	Approved
0.6364	Remote Similarity	NPD5694	Approved
0.6364	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD5693	Phase 1
0.6353	Remote Similarity	NPD5786	Approved
0.6353	Remote Similarity	NPD5279	Phase 3
0.6341	Remote Similarity	NPD4692	Approved
0.6341	Remote Similarity	NPD4790	Discontinued
0.6341	Remote Similarity	NPD4139	Approved
0.6333	Remote Similarity	NPD1693	Approved
0.6322	Remote Similarity	NPD5328	Approved
0.629	Remote Similarity	NPD39	Approved
0.6279	Remote Similarity	NPD1087	Approved
0.6279	Remote Similarity	NPD4793	Discontinued
0.625	Remote Similarity	NPD5207	Approved
0.6237	Remote Similarity	NPD6404	Discontinued
0.6222	Remote Similarity	NPD7900	Approved
0.6222	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4224	Phase 2
0.619	Remote Similarity	NPD9491	Approved
0.6184	Remote Similarity	NPD4137	Phase 3
0.618	Remote Similarity	NPD8035	Phase 2
0.618	Remote Similarity	NPD7983	Approved
0.618	Remote Similarity	NPD8034	Phase 2
0.618	Remote Similarity	NPD6079	Approved
0.6173	Remote Similarity	NPD227	Approved
0.6173	Remote Similarity	NPD225	Approved
0.6154	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4629	Approved
0.6154	Remote Similarity	NPD5210	Approved
0.6154	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7638	Approved
0.6111	Remote Similarity	NPD4194	Approved
0.6111	Remote Similarity	NPD4192	Approved
0.6111	Remote Similarity	NPD4193	Approved
0.6111	Remote Similarity	NPD4202	Approved
0.6111	Remote Similarity	NPD368	Approved
0.6111	Remote Similarity	NPD4191	Approved
0.6104	Remote Similarity	NPD4747	Approved
0.6104	Remote Similarity	NPD4691	Approved
0.6102	Remote Similarity	NPD633	Phase 3
0.6102	Remote Similarity	NPD9448	Phase 2
0.6102	Remote Similarity	NPD77	Approved
0.6102	Remote Similarity	NPD9450	Approved
0.6102	Remote Similarity	NPD9655	Approved
0.6098	Remote Similarity	NPD4195	Approved
0.6087	Remote Similarity	NPD5222	Approved
0.6087	Remote Similarity	NPD7839	Suspended
0.6087	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4697	Phase 3
0.6087	Remote Similarity	NPD5221	Approved
0.6082	Remote Similarity	NPD6402	Approved
0.6082	Remote Similarity	NPD7128	Approved
0.6082	Remote Similarity	NPD5739	Approved
0.6082	Remote Similarity	NPD6675	Approved
0.6067	Remote Similarity	NPD4096	Approved
0.6067	Remote Similarity	NPD5785	Approved
0.6066	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD2066	Phase 3
0.6064	Remote Similarity	NPD7639	Approved
0.6064	Remote Similarity	NPD7640	Approved
0.6053	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD6001	Approved
0.6029	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6081	Approved
0.6026	Remote Similarity	NPD4243	Approved
0.6023	Remote Similarity	NPD4518	Approved
0.6022	Remote Similarity	NPD1565	Approved
0.6022	Remote Similarity	NPD5173	Approved
0.6022	Remote Similarity	NPD4755	Approved
0.6022	Remote Similarity	NPD1566	Phase 3
0.6022	Remote Similarity	NPD1564	Approved
0.602	Remote Similarity	NPD5697	Approved
0.602	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD9439	Approved
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1239	Approved
0.6	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD3704	Approved
0.6	Remote Similarity	NPD9438	Approved
0.5978	Remote Similarity	NPD5654	Approved
0.5972	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD5326	Phase 3

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