NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	2.781
LogD:	1.256
LogS:	-3.308
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.754
Synthetic Accessibility Score:	4.576
Fsp3:	0.667
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:	-5.101
MDCK Permeability:	2.0558487449306995e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.333
Human Intestinal Absorption (HIA):	0.268
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.658

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.776
Plasma Protein Binding (PPB):	87.87862396240234%
Volume Distribution (VD):	0.647
Pgp-substrate:	13.707076072692871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.209
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.069

ADMET: Excretion

Clearance (CL):	5.707
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.468
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.515
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.14
Carcinogencity:	0.511
Eye Corrosion:	0.011
Eye Irritation:	0.479
Respiratory Toxicity:	0.774

Download Data

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

Natural Product: NPC472326

Natural Product ID:	NPC472326
*Common Name:**	FDIVBBVUHYDHDS-COMQUAJESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FDIVBBVUHYDHDS-COMQUAJESA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9(2)5-4-6-15(3)11-7-10(14(17)18)8-12(16)13(11)15/h5,7,11-13,16H,4,6,8H2,1-3H3,(H,17,18)/t11-,12+,13-,15+/m1/s1
SMILES:	CC(=CCC[C@]1(C)[C@@H]2[C@H]1C=C(C[C@@H]2O)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359153
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
NPO33267	eupenicillium sp. lg41	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25356913]

☑ 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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	MIC	>	10.0	ug.mL-1	PMID[568755]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5.0	ug.mL-1	PMID[568755]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	10.0	ug.mL-1	PMID[568755]
NPT4080	Organism	Acinetobacter sp.	Acinetobacter sp.	MIC	=	5.0	ug.mL-1	PMID[568755]

☑ 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 NPC472326 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	195
0.1-0.2	1182
0.2-0.3	5322
0.3-0.4	13919
0.4-0.5	10516
0.5-0.6	6434
0.6-0.7	4351
0.7-0.8	747
0.8-0.85	26
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8608	High Similarity	NPC472327
0.8537	High Similarity	NPC271104
0.8372	Intermediate Similarity	NPC473226
0.8333	Intermediate Similarity	NPC93590
0.8313	Intermediate Similarity	NPC172013
0.8293	Intermediate Similarity	NPC475994
0.8276	Intermediate Similarity	NPC312561
0.8202	Intermediate Similarity	NPC469368
0.8193	Intermediate Similarity	NPC308038
0.8193	Intermediate Similarity	NPC281138
0.8182	Intermediate Similarity	NPC473229
0.8161	Intermediate Similarity	NPC82979
0.8111	Intermediate Similarity	NPC233345
0.8111	Intermediate Similarity	NPC186363
0.8072	Intermediate Similarity	NPC169095
0.8046	Intermediate Similarity	NPC52628
0.8043	Intermediate Similarity	NPC183012
0.8	Intermediate Similarity	NPC473420
0.8	Intermediate Similarity	NPC232426
0.8	Intermediate Similarity	NPC281942
0.7979	Intermediate Similarity	NPC478056
0.7978	Intermediate Similarity	NPC136879
0.7978	Intermediate Similarity	NPC104560
0.7978	Intermediate Similarity	NPC277771
0.7976	Intermediate Similarity	NPC19900
0.7955	Intermediate Similarity	NPC6979
0.7952	Intermediate Similarity	NPC97377
0.7952	Intermediate Similarity	NPC471061
0.7952	Intermediate Similarity	NPC197659
0.7931	Intermediate Similarity	NPC7927
0.7931	Intermediate Similarity	NPC230527
0.7931	Intermediate Similarity	NPC82297
0.7927	Intermediate Similarity	NPC476795
0.7912	Intermediate Similarity	NPC141831
0.7907	Intermediate Similarity	NPC158411
0.7907	Intermediate Similarity	NPC38796
0.7895	Intermediate Similarity	NPC470074
0.7895	Intermediate Similarity	NPC476274
0.7889	Intermediate Similarity	NPC472983
0.7889	Intermediate Similarity	NPC168131
0.7889	Intermediate Similarity	NPC218927
0.7889	Intermediate Similarity	NPC206001
0.7872	Intermediate Similarity	NPC170131
0.7857	Intermediate Similarity	NPC62336
0.7849	Intermediate Similarity	NPC476174
0.7849	Intermediate Similarity	NPC53565
0.7841	Intermediate Similarity	NPC28887
0.7841	Intermediate Similarity	NPC179006
0.7841	Intermediate Similarity	NPC476426
0.7841	Intermediate Similarity	NPC474853
0.7831	Intermediate Similarity	NPC470525
0.7831	Intermediate Similarity	NPC263582
0.7826	Intermediate Similarity	NPC166346
0.7826	Intermediate Similarity	NPC115021
0.7821	Intermediate Similarity	NPC166791
0.7821	Intermediate Similarity	NPC322035
0.7821	Intermediate Similarity	NPC100719
0.7816	Intermediate Similarity	NPC49019
0.7812	Intermediate Similarity	NPC476223
0.7812	Intermediate Similarity	NPC115862
0.7812	Intermediate Similarity	NPC81530
0.7812	Intermediate Similarity	NPC224720
0.7812	Intermediate Similarity	NPC476240
0.7805	Intermediate Similarity	NPC215050
0.7802	Intermediate Similarity	NPC134321
0.7789	Intermediate Similarity	NPC316598
0.7789	Intermediate Similarity	NPC23364
0.7778	Intermediate Similarity	NPC48107
0.7778	Intermediate Similarity	NPC249889
0.7778	Intermediate Similarity	NPC477302
0.7778	Intermediate Similarity	NPC193843
0.7753	Intermediate Similarity	NPC194417
0.7753	Intermediate Similarity	NPC477920
0.7753	Intermediate Similarity	NPC472974
0.7753	Intermediate Similarity	NPC202394
0.7753	Intermediate Similarity	NPC475461
0.7753	Intermediate Similarity	NPC250981
0.7753	Intermediate Similarity	NPC305475
0.7742	Intermediate Similarity	NPC53685
0.7742	Intermediate Similarity	NPC196227
0.7738	Intermediate Similarity	NPC74995
0.7738	Intermediate Similarity	NPC203403
0.7738	Intermediate Similarity	NPC476007
0.7732	Intermediate Similarity	NPC136289
0.7727	Intermediate Similarity	NPC114979
0.7727	Intermediate Similarity	NPC470812
0.7727	Intermediate Similarity	NPC191476
0.7727	Intermediate Similarity	NPC165064
0.7722	Intermediate Similarity	NPC472875
0.7717	Intermediate Similarity	NPC116726
0.7717	Intermediate Similarity	NPC252433
0.7711	Intermediate Similarity	NPC474885
0.7711	Intermediate Similarity	NPC114236
0.7701	Intermediate Similarity	NPC279186
0.7701	Intermediate Similarity	NPC73882
0.7692	Intermediate Similarity	NPC214387
0.7692	Intermediate Similarity	NPC50488
0.7692	Intermediate Similarity	NPC118011
0.7692	Intermediate Similarity	NPC314727
0.7692	Intermediate Similarity	NPC5509
0.7692	Intermediate Similarity	NPC474396
0.7692	Intermediate Similarity	NPC36668
0.7692	Intermediate Similarity	NPC310236
0.7692	Intermediate Similarity	NPC477215
0.7692	Intermediate Similarity	NPC476388
0.7692	Intermediate Similarity	NPC477973
0.7684	Intermediate Similarity	NPC70145
0.7684	Intermediate Similarity	NPC91695
0.7684	Intermediate Similarity	NPC474343
0.7683	Intermediate Similarity	NPC35656
0.7683	Intermediate Similarity	NPC186042
0.7674	Intermediate Similarity	NPC148685
0.7674	Intermediate Similarity	NPC104120
0.7674	Intermediate Similarity	NPC471514
0.7674	Intermediate Similarity	NPC472301
0.7674	Intermediate Similarity	NPC157895
0.7674	Intermediate Similarity	NPC45495
0.7667	Intermediate Similarity	NPC470012
0.7667	Intermediate Similarity	NPC477926
0.7667	Intermediate Similarity	NPC237540
0.7653	Intermediate Similarity	NPC476237
0.7647	Intermediate Similarity	NPC172066
0.7647	Intermediate Similarity	NPC239098
0.7647	Intermediate Similarity	NPC192006
0.7647	Intermediate Similarity	NPC198240
0.7647	Intermediate Similarity	NPC74410
0.7647	Intermediate Similarity	NPC178852
0.764	Intermediate Similarity	NPC165162
0.764	Intermediate Similarity	NPC15807
0.764	Intermediate Similarity	NPC177932
0.764	Intermediate Similarity	NPC109528
0.764	Intermediate Similarity	NPC255307
0.7634	Intermediate Similarity	NPC476416
0.7634	Intermediate Similarity	NPC109305
0.7629	Intermediate Similarity	NPC97435
0.7629	Intermediate Similarity	NPC469657
0.7629	Intermediate Similarity	NPC244456
0.7614	Intermediate Similarity	NPC470948
0.7614	Intermediate Similarity	NPC297398
0.7614	Intermediate Similarity	NPC22611
0.7614	Intermediate Similarity	NPC105173
0.7614	Intermediate Similarity	NPC312480
0.7614	Intermediate Similarity	NPC193198
0.7614	Intermediate Similarity	NPC243347
0.7614	Intermediate Similarity	NPC57370
0.7614	Intermediate Similarity	NPC97913
0.7609	Intermediate Similarity	NPC477149
0.7609	Intermediate Similarity	NPC128672
0.7609	Intermediate Similarity	NPC473099
0.7609	Intermediate Similarity	NPC477147
0.7609	Intermediate Similarity	NPC158488
0.7604	Intermediate Similarity	NPC166745
0.7604	Intermediate Similarity	NPC235464
0.7604	Intermediate Similarity	NPC197386
0.7604	Intermediate Similarity	NPC194196
0.7604	Intermediate Similarity	NPC216478
0.7586	Intermediate Similarity	NPC325031
0.7586	Intermediate Similarity	NPC159148
0.7586	Intermediate Similarity	NPC470298
0.7586	Intermediate Similarity	NPC226068
0.7586	Intermediate Similarity	NPC470241
0.7582	Intermediate Similarity	NPC471791
0.7582	Intermediate Similarity	NPC117122
0.7582	Intermediate Similarity	NPC471793
0.7582	Intermediate Similarity	NPC215831
0.7579	Intermediate Similarity	NPC117133
0.7579	Intermediate Similarity	NPC116457
0.7579	Intermediate Similarity	NPC235053
0.7579	Intermediate Similarity	NPC202833
0.7579	Intermediate Similarity	NPC29152
0.7579	Intermediate Similarity	NPC301534
0.7579	Intermediate Similarity	NPC472941
0.7579	Intermediate Similarity	NPC456
0.7579	Intermediate Similarity	NPC250757
0.7576	Intermediate Similarity	NPC118911
0.7561	Intermediate Similarity	NPC474884
0.7558	Intermediate Similarity	NPC246458
0.7558	Intermediate Similarity	NPC89128
0.7558	Intermediate Similarity	NPC152061
0.7558	Intermediate Similarity	NPC470239
0.7558	Intermediate Similarity	NPC470244
0.7558	Intermediate Similarity	NPC7232
0.7556	Intermediate Similarity	NPC198761
0.7556	Intermediate Similarity	NPC85698
0.7556	Intermediate Similarity	NPC476982
0.7556	Intermediate Similarity	NPC472986
0.7556	Intermediate Similarity	NPC186975
0.7556	Intermediate Similarity	NPC472985
0.7556	Intermediate Similarity	NPC185638
0.7556	Intermediate Similarity	NPC470955
0.7556	Intermediate Similarity	NPC322159
0.7553	Intermediate Similarity	NPC476186
0.7553	Intermediate Similarity	NPC181393
0.7553	Intermediate Similarity	NPC217624
0.7553	Intermediate Similarity	NPC477130
0.7553	Intermediate Similarity	NPC477129
0.7553	Intermediate Similarity	NPC475572
0.7553	Intermediate Similarity	NPC250075
0.7551	Intermediate Similarity	NPC195290
0.7551	Intermediate Similarity	NPC118405

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 NPC472326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1822
0.2-0.3	3769
0.3-0.4	2289
0.4-0.5	666
0.5-0.6	318
0.6-0.7	96
0.7-0.8	8
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
0.764	Intermediate Similarity	NPD1694	Approved
0.7444	Intermediate Similarity	NPD5363	Approved
0.7444	Intermediate Similarity	NPD1696	Phase 3
0.7419	Intermediate Similarity	NPD5785	Approved
0.7363	Intermediate Similarity	NPD3618	Phase 1
0.734	Intermediate Similarity	NPD7515	Phase 2
0.7292	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7111	Intermediate Similarity	NPD4269	Approved
0.7111	Intermediate Similarity	NPD4270	Approved
0.7111	Intermediate Similarity	NPD3667	Approved
0.7083	Intermediate Similarity	NPD5779	Approved
0.7083	Intermediate Similarity	NPD5778	Approved
0.7083	Intermediate Similarity	NPD6399	Phase 3
0.7071	Intermediate Similarity	NPD4225	Approved
0.7053	Intermediate Similarity	NPD46	Approved
0.7053	Intermediate Similarity	NPD6698	Approved
0.7048	Intermediate Similarity	NPD6371	Approved
0.7033	Intermediate Similarity	NPD5362	Discontinued
0.701	Intermediate Similarity	NPD7748	Approved
0.6979	Remote Similarity	NPD6079	Approved
0.6979	Remote Similarity	NPD6411	Approved
0.6972	Remote Similarity	NPD7115	Discovery
0.6957	Remote Similarity	NPD4786	Approved
0.6947	Remote Similarity	NPD5328	Approved
0.6923	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4202	Approved
0.6889	Remote Similarity	NPD4252	Approved
0.6889	Remote Similarity	NPD4821	Approved
0.6889	Remote Similarity	NPD4822	Approved
0.6889	Remote Similarity	NPD4819	Approved
0.6889	Remote Similarity	NPD4695	Discontinued
0.6889	Remote Similarity	NPD4820	Approved
0.6875	Remote Similarity	NPD368	Approved
0.6863	Remote Similarity	NPD5211	Phase 2
0.6854	Remote Similarity	NPD4268	Approved
0.6854	Remote Similarity	NPD4271	Approved
0.6848	Remote Similarity	NPD7154	Phase 3
0.6837	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7900	Approved
0.6832	Remote Similarity	NPD7640	Approved
0.6832	Remote Similarity	NPD7639	Approved
0.6809	Remote Similarity	NPD5330	Approved
0.6809	Remote Similarity	NPD5279	Phase 3
0.6809	Remote Similarity	NPD7521	Approved
0.6809	Remote Similarity	NPD4623	Approved
0.6809	Remote Similarity	NPD5786	Approved
0.6809	Remote Similarity	NPD7146	Approved
0.6809	Remote Similarity	NPD4519	Discontinued
0.6809	Remote Similarity	NPD7334	Approved
0.6809	Remote Similarity	NPD6684	Approved
0.6809	Remote Similarity	NPD6409	Approved
0.6804	Remote Similarity	NPD5284	Approved
0.6804	Remote Similarity	NPD5281	Approved
0.6771	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6101	Approved
0.6762	Remote Similarity	NPD5697	Approved
0.6742	Remote Similarity	NPD4756	Discovery
0.6733	Remote Similarity	NPD7638	Approved
0.6731	Remote Similarity	NPD5141	Approved
0.6703	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5222	Approved
0.67	Remote Similarity	NPD5221	Approved
0.67	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4697	Phase 3
0.6698	Remote Similarity	NPD6881	Approved
0.6698	Remote Similarity	NPD6899	Approved
0.6698	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6636	Remote Similarity	NPD6014	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6634	Remote Similarity	NPD5173	Approved
0.6634	Remote Similarity	NPD6083	Phase 2
0.6634	Remote Similarity	NPD4755	Approved
0.6634	Remote Similarity	NPD6084	Phase 2
0.6632	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4790	Discontinued
0.663	Remote Similarity	NPD5369	Approved
0.6604	Remote Similarity	NPD5701	Approved
0.6602	Remote Similarity	NPD5223	Approved
0.66	Remote Similarity	NPD5210	Approved
0.66	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD4629	Approved
0.66	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4753	Phase 2
0.6598	Remote Similarity	NPD1695	Approved
0.6574	Remote Similarity	NPD7102	Approved
0.6574	Remote Similarity	NPD7290	Approved
0.6574	Remote Similarity	NPD6883	Approved
0.6569	Remote Similarity	NPD5696	Approved
0.6562	Remote Similarity	NPD3573	Approved
0.6559	Remote Similarity	NPD4223	Phase 3
0.6559	Remote Similarity	NPD5209	Approved
0.6559	Remote Similarity	NPD4221	Approved
0.6548	Remote Similarity	NPD7331	Phase 2
0.6542	Remote Similarity	NPD7320	Approved
0.6542	Remote Similarity	NPD6686	Approved
0.6538	Remote Similarity	NPD5224	Approved
0.6538	Remote Similarity	NPD342	Phase 1
0.6538	Remote Similarity	NPD5226	Approved
0.6538	Remote Similarity	NPD5225	Approved
0.6538	Remote Similarity	NPD4633	Approved
0.6531	Remote Similarity	NPD7838	Discovery
0.6526	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5368	Approved
0.6517	Remote Similarity	NPD8264	Approved
0.6517	Remote Similarity	NPD8039	Approved
0.6514	Remote Similarity	NPD6847	Approved
0.6514	Remote Similarity	NPD8130	Phase 1
0.6514	Remote Similarity	NPD6617	Approved
0.6514	Remote Similarity	NPD6869	Approved
0.6509	Remote Similarity	NPD6008	Approved
0.6505	Remote Similarity	NPD4700	Approved
0.6505	Remote Similarity	NPD6404	Discontinued
0.65	Remote Similarity	NPD6001	Approved
0.65	Remote Similarity	NPD5282	Discontinued
0.6495	Remote Similarity	NPD6672	Approved
0.6495	Remote Similarity	NPD5737	Approved
0.6481	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5175	Approved
0.6476	Remote Similarity	NPD5174	Approved
0.6465	Remote Similarity	NPD7983	Approved
0.6458	Remote Similarity	NPD5690	Phase 2
0.6455	Remote Similarity	NPD6882	Approved
0.6455	Remote Similarity	NPD8297	Approved
0.6442	Remote Similarity	NPD5344	Discontinued
0.6429	Remote Similarity	NPD7341	Phase 2
0.6422	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3668	Phase 3
0.6421	Remote Similarity	NPD4197	Approved
0.6421	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4632	Approved
0.6383	Remote Similarity	NPD6435	Approved
0.6364	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5329	Approved
0.6354	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4754	Approved
0.6306	Remote Similarity	NPD6053	Discontinued
0.6304	Remote Similarity	NPD3617	Approved
0.63	Remote Similarity	NPD8034	Phase 2
0.63	Remote Similarity	NPD7637	Suspended
0.63	Remote Similarity	NPD8035	Phase 2
0.6296	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4693	Phase 3
0.6289	Remote Similarity	NPD5205	Approved
0.6289	Remote Similarity	NPD5280	Approved
0.6289	Remote Similarity	NPD4694	Approved
0.6289	Remote Similarity	NPD4688	Approved
0.6289	Remote Similarity	NPD4690	Approved
0.6289	Remote Similarity	NPD4689	Approved
0.6289	Remote Similarity	NPD4138	Approved
0.6289	Remote Similarity	NPD4249	Approved
0.6283	Remote Similarity	NPD6274	Approved
0.6265	Remote Similarity	NPD4191	Approved
0.6265	Remote Similarity	NPD4192	Approved
0.6265	Remote Similarity	NPD4194	Approved
0.6265	Remote Similarity	NPD4193	Approved
0.6264	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD5128	Approved
0.6239	Remote Similarity	NPD4730	Approved
0.6235	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6009	Approved
0.6228	Remote Similarity	NPD6317	Approved
0.6226	Remote Similarity	NPD7632	Discontinued
0.6224	Remote Similarity	NPD4250	Approved
0.6224	Remote Similarity	NPD4251	Approved
0.6214	Remote Similarity	NPD7614	Phase 1
0.6214	Remote Similarity	NPD7839	Suspended
0.6204	Remote Similarity	NPD4768	Approved
0.6204	Remote Similarity	NPD4767	Approved
0.62	Remote Similarity	NPD5207	Approved
0.619	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6648	Approved
0.6186	Remote Similarity	NPD7604	Phase 2
0.6174	Remote Similarity	NPD6335	Approved
0.6174	Remote Similarity	NPD6313	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