NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	406.19
Volume:	423.804
LogP:	6.846
LogD:	4.489
LogS:	-4.258
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	4.221
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.653
MDCK Permeability:	2.20E-05
Pgp-inhibitor:	0.47
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	100.58%
Volume Distribution (VD):	3.759
Pgp-substrate:	1.71%

ADMET: Metabolism

CYP1A2-inhibitor:	0.376
CYP1A2-substrate:	0.272
CYP2C19-inhibitor:	0.665
CYP2C19-substrate:	0.673
CYP2C9-inhibitor:	0.752
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.542
CYP2D6-substrate:	0.329
CYP3A4-inhibitor:	0.354
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	8.542
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.269
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.753
Skin Sensitization:	0.807
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.616
Respiratory Toxicity:	0.72

Download Data

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

Natural Product: NPC477568

Natural Product ID:	NPC477568
*Common Name:**	7-chloro-4-hydroxy-2-[(5E)-2-hydroxy-6,10-dimethylundeca-5,9-dien-2-yl]-6-methyl-2,3-dihydro-1-benzofuran-5-carbaldehyde
IUPAC Name:	7-chloro-4-hydroxy-2-[(5E)-2-hydroxy-6,10-dimethylundeca-5,9-dien-2-yl]-6-methyl-2,3-dihydro-1-benzofuran-5-carbaldehyde
Synonyms:
Standard InCHIKey:	AKZMNMUPGWZYPW-XNTDXEJSSA-N
Standard InCHI:	InChI=1S/C23H31ClO4/c1-14(2)8-6-9-15(3)10-7-11-23(5,27)19-12-17-21(26)18(13-25)16(4)20(24)22(17)28-19/h8,10,13,19,26-27H,6-7,9,11-12H2,1-5H3/b15-10+
SMILES:	CC1=C(C(=C2CC(OC2=C1Cl)C(C)(CC/C=C(\C)/CCC=C(C)C)O)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118724833
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
NPO33613	Neonectria discophora	Species	Nectriaceae	Eukaryota	n.a.	Rmire-Montjoly, French Guiana	2011-JUL	PMID[25478997]

☑ 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	3
MIC	6

Activity Type	# Activity
Cell Line	2
Organism	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	15100	nM	PMID[25478997]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	16500	nM	PMID[25478997]
NPT2	Others	Unspecified		IC50	=	16400	nM	PMID[25478997]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128	ug/ml	PMID[25478997]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64	ug/ml	PMID[25478997]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	128	ug/ml	PMID[25478997]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	128	ug/ml	PMID[25478997]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	128	ug/ml	PMID[25478997]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	128	ug/ml	PMID[25478997]

☑ 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 NPC477568 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	464
0.1-0.2	1954
0.2-0.3	5087
0.3-0.4	12305
0.4-0.5	6769
0.5-0.6	5835
0.6-0.7	7635
0.7-0.8	2583
0.8-0.85	54
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8976	High Similarity	NPC245122
0.8757	High Similarity	NPC474499
0.8722	High Similarity	NPC247104
0.8667	High Similarity	NPC221185
0.8659	High Similarity	NPC470100
0.8626	High Similarity	NPC198163
0.8619	High Similarity	NPC214901
0.8613	High Similarity	NPC474857
0.8571	High Similarity	NPC45072
0.8564	High Similarity	NPC220369
0.8556	High Similarity	NPC470099
0.8486	Intermediate Similarity	NPC108744
0.847	Intermediate Similarity	NPC48822
0.8436	Intermediate Similarity	NPC99937
0.8432	Intermediate Similarity	NPC154720
0.8424	Intermediate Similarity	NPC193676
0.8409	Intermediate Similarity	NPC264922
0.8343	Intermediate Similarity	NPC277865
0.8343	Intermediate Similarity	NPC280497
0.8333	Intermediate Similarity	NPC472032
0.8313	Intermediate Similarity	NPC477567
0.8313	Intermediate Similarity	NPC477566
0.8303	Intermediate Similarity	NPC477569
0.8287	Intermediate Similarity	NPC470103
0.8256	Intermediate Similarity	NPC472405
0.8239	Intermediate Similarity	NPC107283
0.8239	Intermediate Similarity	NPC470562
0.8221	Intermediate Similarity	NPC74397
0.8218	Intermediate Similarity	NPC68850
0.8208	Intermediate Similarity	NPC474096
0.8198	Intermediate Similarity	NPC470810
0.8192	Intermediate Similarity	NPC470560
0.8187	Intermediate Similarity	NPC191606
0.8167	Intermediate Similarity	NPC471801
0.8161	Intermediate Similarity	NPC470081
0.815	Intermediate Similarity	NPC298401
0.8146	Intermediate Similarity	NPC470422
0.8136	Intermediate Similarity	NPC470565
0.8122	Intermediate Similarity	NPC151292
0.8114	Intermediate Similarity	NPC58653
0.8114	Intermediate Similarity	NPC173352
0.8103	Intermediate Similarity	NPC473696
0.8084	Intermediate Similarity	NPC8817
0.8079	Intermediate Similarity	NPC148480
0.8072	Intermediate Similarity	NPC75694
0.8068	Intermediate Similarity	NPC28669
0.8054	Intermediate Similarity	NPC39409
0.8036	Intermediate Similarity	NPC470359
0.8024	Intermediate Similarity	NPC470357
0.8011	Intermediate Similarity	NPC234053
0.8	Intermediate Similarity	NPC471804
0.8	Intermediate Similarity	NPC471812
0.8	Intermediate Similarity	NPC471803
0.8	Intermediate Similarity	NPC313386
0.7977	Intermediate Similarity	NPC472404
0.7976	Intermediate Similarity	NPC137296
0.7966	Intermediate Similarity	NPC474061
0.7955	Intermediate Similarity	NPC470563
0.7955	Intermediate Similarity	NPC100849
0.7952	Intermediate Similarity	NPC200207
0.7941	Intermediate Similarity	NPC179178
0.7941	Intermediate Similarity	NPC476509
0.7937	Intermediate Similarity	NPC313541
0.7914	Intermediate Similarity	NPC471807
0.7914	Intermediate Similarity	NPC471806
0.7914	Intermediate Similarity	NPC471810
0.7912	Intermediate Similarity	NPC471802
0.7904	Intermediate Similarity	NPC18886
0.7903	Intermediate Similarity	NPC316091
0.7898	Intermediate Similarity	NPC470561
0.7892	Intermediate Similarity	NPC471809
0.7892	Intermediate Similarity	NPC471811
0.7889	Intermediate Similarity	NPC188618
0.7886	Intermediate Similarity	NPC470358
0.787	Intermediate Similarity	NPC202494
0.7861	Intermediate Similarity	NPC471805
0.7861	Intermediate Similarity	NPC121100
0.7861	Intermediate Similarity	NPC471813
0.7853	Intermediate Similarity	NPC475055
0.7849	Intermediate Similarity	NPC271681
0.7844	Intermediate Similarity	NPC276565
0.7841	Intermediate Similarity	NPC117985
0.7838	Intermediate Similarity	NPC471808
0.7838	Intermediate Similarity	NPC471814
0.7838	Intermediate Similarity	NPC195675
0.7836	Intermediate Similarity	NPC327059
0.7836	Intermediate Similarity	NPC470908
0.7836	Intermediate Similarity	NPC321387
0.7836	Intermediate Similarity	NPC472421
0.7829	Intermediate Similarity	NPC85121
0.7814	Intermediate Similarity	NPC472606
0.7814	Intermediate Similarity	NPC28160
0.7809	Intermediate Similarity	NPC477834
0.7807	Intermediate Similarity	NPC136411
0.7797	Intermediate Similarity	NPC472402
0.7791	Intermediate Similarity	NPC200773
0.7791	Intermediate Similarity	NPC474744
0.7791	Intermediate Similarity	NPC472423
0.7791	Intermediate Similarity	NPC72958
0.7791	Intermediate Similarity	NPC474772
0.7791	Intermediate Similarity	NPC478148
0.7791	Intermediate Similarity	NPC240768
0.7791	Intermediate Similarity	NPC471675
0.7791	Intermediate Similarity	NPC232645
0.7791	Intermediate Similarity	NPC474417
0.7791	Intermediate Similarity	NPC149526
0.7791	Intermediate Similarity	NPC472636
0.7784	Intermediate Similarity	NPC171870
0.7784	Intermediate Similarity	NPC313368
0.7771	Intermediate Similarity	NPC272196
0.7765	Intermediate Similarity	NPC43319
0.7765	Intermediate Similarity	NPC53362
0.7765	Intermediate Similarity	NPC166583
0.7765	Intermediate Similarity	NPC53640
0.7765	Intermediate Similarity	NPC470670
0.7765	Intermediate Similarity	NPC47388
0.7765	Intermediate Similarity	NPC473133
0.7765	Intermediate Similarity	NPC170245
0.7765	Intermediate Similarity	NPC91902
0.776	Intermediate Similarity	NPC108278
0.7759	Intermediate Similarity	NPC149618
0.7759	Intermediate Similarity	NPC89625
0.7751	Intermediate Similarity	NPC297788
0.7747	Intermediate Similarity	NPC98776
0.7746	Intermediate Similarity	NPC87708
0.7746	Intermediate Similarity	NPC327269
0.7746	Intermediate Similarity	NPC31627
0.7746	Intermediate Similarity	NPC473996
0.7746	Intermediate Similarity	NPC273483
0.7746	Intermediate Similarity	NPC476238
0.7738	Intermediate Similarity	NPC130206
0.7735	Intermediate Similarity	NPC474004
0.7735	Intermediate Similarity	NPC315306
0.7735	Intermediate Similarity	NPC313717
0.7722	Intermediate Similarity	NPC218226
0.7722	Intermediate Similarity	NPC474024
0.7719	Intermediate Similarity	NPC37139
0.7714	Intermediate Similarity	NPC164427
0.7714	Intermediate Similarity	NPC180924
0.7714	Intermediate Similarity	NPC477674
0.7709	Intermediate Similarity	NPC326520
0.7701	Intermediate Similarity	NPC472799
0.7701	Intermediate Similarity	NPC477669
0.7701	Intermediate Similarity	NPC169990
0.7701	Intermediate Similarity	NPC210942
0.7692	Intermediate Similarity	NPC5990
0.7688	Intermediate Similarity	NPC472580
0.7684	Intermediate Similarity	NPC304839
0.7684	Intermediate Similarity	NPC472624
0.7684	Intermediate Similarity	NPC328102
0.7684	Intermediate Similarity	NPC143050
0.7684	Intermediate Similarity	NPC36217
0.7684	Intermediate Similarity	NPC220582
0.768	Intermediate Similarity	NPC473202
0.7676	Intermediate Similarity	NPC306240
0.7674	Intermediate Similarity	NPC291049
0.7674	Intermediate Similarity	NPC158338
0.7674	Intermediate Similarity	NPC65589
0.7674	Intermediate Similarity	NPC100985
0.7674	Intermediate Similarity	NPC97028
0.7674	Intermediate Similarity	NPC97029
0.7674	Intermediate Similarity	NPC288036
0.7674	Intermediate Similarity	NPC233267
0.767	Intermediate Similarity	NPC246647
0.767	Intermediate Similarity	NPC212967
0.767	Intermediate Similarity	NPC96342
0.767	Intermediate Similarity	NPC44199
0.767	Intermediate Similarity	NPC164110
0.7667	Intermediate Similarity	NPC165460
0.7667	Intermediate Similarity	NPC272502
0.7667	Intermediate Similarity	NPC178851
0.7663	Intermediate Similarity	NPC312630
0.7663	Intermediate Similarity	NPC478050
0.7663	Intermediate Similarity	NPC475233
0.7663	Intermediate Similarity	NPC324220
0.7661	Intermediate Similarity	NPC85773
0.7661	Intermediate Similarity	NPC14875
0.7661	Intermediate Similarity	NPC469425
0.7657	Intermediate Similarity	NPC108937
0.7657	Intermediate Similarity	NPC279218
0.7657	Intermediate Similarity	NPC79998
0.7657	Intermediate Similarity	NPC175192
0.7654	Intermediate Similarity	NPC173587
0.7654	Intermediate Similarity	NPC186686
0.7654	Intermediate Similarity	NPC208120
0.7654	Intermediate Similarity	NPC475985
0.7654	Intermediate Similarity	NPC197168
0.7647	Intermediate Similarity	NPC470857
0.7644	Intermediate Similarity	NPC470337
0.7644	Intermediate Similarity	NPC470340
0.7644	Intermediate Similarity	NPC477957
0.7644	Intermediate Similarity	NPC113608
0.7644	Intermediate Similarity	NPC268992
0.7644	Intermediate Similarity	NPC154683
0.7644	Intermediate Similarity	NPC285623
0.7644	Intermediate Similarity	NPC217447
0.7644	Intermediate Similarity	NPC40356
0.7644	Intermediate Similarity	NPC51824
0.7644	Intermediate Similarity	NPC470338
0.764	Intermediate Similarity	NPC45124

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 NPC477568 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	1151
0.2-0.3	2360
0.3-0.4	2757
0.4-0.5	1571
0.5-0.6	668
0.6-0.7	225
0.7-0.8	20
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
0.8072	Intermediate Similarity	NPD2534	Approved
0.8072	Intermediate Similarity	NPD2533	Approved
0.8072	Intermediate Similarity	NPD2532	Approved
0.8011	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2800	Approved
0.7444	Intermediate Similarity	NPD6959	Discontinued
0.7403	Intermediate Similarity	NPD5711	Approved
0.7403	Intermediate Similarity	NPD5710	Approved
0.7366	Intermediate Similarity	NPD6559	Discontinued
0.7345	Intermediate Similarity	NPD1934	Approved
0.7241	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD3882	Suspended
0.7213	Intermediate Similarity	NPD6232	Discontinued
0.7207	Intermediate Similarity	NPD7819	Suspended
0.7193	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7075	Discontinued
0.7128	Intermediate Similarity	NPD4360	Phase 2
0.7128	Intermediate Similarity	NPD4363	Phase 3
0.7112	Intermediate Similarity	NPD5844	Phase 1
0.7111	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2801	Approved
0.7104	Intermediate Similarity	NPD5494	Approved
0.7097	Intermediate Similarity	NPD7473	Discontinued
0.7092	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4361	Phase 2
0.7072	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3818	Discontinued
0.7045	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6166	Phase 2
0.7043	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6599	Discontinued
0.7035	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1549	Phase 2
0.6989	Remote Similarity	NPD1511	Approved
0.6964	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6801	Discontinued
0.694	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.691	Remote Similarity	NPD1512	Approved
0.6901	Remote Similarity	NPD6651	Approved
0.6901	Remote Similarity	NPD1607	Approved
0.6895	Remote Similarity	NPD7074	Phase 3
0.6893	Remote Similarity	NPD6799	Approved
0.6885	Remote Similarity	NPD3817	Phase 2
0.6882	Remote Similarity	NPD1247	Approved
0.6879	Remote Similarity	NPD2796	Approved
0.6879	Remote Similarity	NPD1551	Phase 2
0.6872	Remote Similarity	NPD920	Approved
0.6865	Remote Similarity	NPD919	Approved
0.6854	Remote Similarity	NPD1578	Phase 2
0.6842	Remote Similarity	NPD7054	Approved
0.6821	Remote Similarity	NPD1510	Phase 2
0.6818	Remote Similarity	NPD4628	Phase 3
0.6813	Remote Similarity	NPD958	Approved
0.6813	Remote Similarity	NPD7411	Suspended
0.6811	Remote Similarity	NPD3749	Approved
0.6806	Remote Similarity	NPD7472	Approved
0.6784	Remote Similarity	NPD1240	Approved
0.6782	Remote Similarity	NPD6099	Approved
0.6782	Remote Similarity	NPD6100	Approved
0.6771	Remote Similarity	NPD6797	Phase 2
0.6768	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.676	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7768	Phase 2
0.6742	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7251	Discontinued
0.6724	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7390	Discontinued
0.6703	Remote Similarity	NPD3226	Approved
0.6701	Remote Similarity	NPD7808	Phase 3
0.6686	Remote Similarity	NPD2935	Discontinued
0.6684	Remote Similarity	NPD6234	Discontinued
0.6684	Remote Similarity	NPD6784	Approved
0.6684	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD1243	Approved
0.665	Remote Similarity	NPD8434	Phase 2
0.6649	Remote Similarity	NPD1465	Phase 2
0.6648	Remote Similarity	NPD957	Approved
0.6648	Remote Similarity	NPD5058	Phase 3
0.6648	Remote Similarity	NPD2346	Discontinued
0.6629	Remote Similarity	NPD5588	Approved
0.6629	Remote Similarity	NPD3750	Approved
0.6615	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5402	Approved
0.6595	Remote Similarity	NPD37	Approved
0.6588	Remote Similarity	NPD454	Approved
0.6582	Remote Similarity	NPD8313	Approved
0.6582	Remote Similarity	NPD8312	Approved
0.6578	Remote Similarity	NPD4967	Phase 2
0.6578	Remote Similarity	NPD4966	Approved
0.6578	Remote Similarity	NPD4965	Approved
0.6575	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4538	Approved
0.6571	Remote Similarity	NPD4536	Approved
0.6571	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5760	Phase 2
0.6559	Remote Similarity	NPD5761	Phase 2
0.6552	Remote Similarity	NPD230	Phase 1
0.6545	Remote Similarity	NPD3926	Phase 2
0.6538	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD6779	Approved
0.6537	Remote Similarity	NPD6781	Approved
0.6537	Remote Similarity	NPD6782	Approved
0.6537	Remote Similarity	NPD6776	Approved
0.6537	Remote Similarity	NPD6777	Approved
0.6537	Remote Similarity	NPD6780	Approved
0.6537	Remote Similarity	NPD6778	Approved
0.6526	Remote Similarity	NPD7199	Phase 2
0.6524	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4625	Phase 3
0.6503	Remote Similarity	NPD5403	Approved
0.65	Remote Similarity	NPD3887	Approved
0.65	Remote Similarity	NPD2354	Approved
0.65	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7229	Phase 3
0.648	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7783	Phase 2
0.6462	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD2344	Approved
0.6458	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5124	Phase 1
0.6457	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD8151	Discontinued
0.6443	Remote Similarity	NPD7228	Approved
0.6443	Remote Similarity	NPD3751	Discontinued
0.6442	Remote Similarity	NPD7435	Discontinued
0.6441	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5960	Phase 3
0.6436	Remote Similarity	NPD3819	Phase 2
0.6432	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5953	Discontinued
0.6421	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6696	Suspended
0.641	Remote Similarity	NPD7286	Phase 2
0.6406	Remote Similarity	NPD3787	Discontinued
0.6404	Remote Similarity	NPD1852	Discontinued
0.64	Remote Similarity	NPD8150	Discontinued
0.6398	Remote Similarity	NPD4972	Discontinued
0.6393	Remote Similarity	NPD5401	Approved
0.6393	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2654	Approved
0.6379	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6535	Approved
0.6373	Remote Similarity	NPD6534	Approved
0.6369	Remote Similarity	NPD6002	Phase 3
0.6369	Remote Similarity	NPD6005	Phase 3
0.6369	Remote Similarity	NPD6004	Phase 3
0.6369	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7696	Phase 3
0.6364	Remote Similarity	NPD7698	Approved
0.6364	Remote Similarity	NPD7697	Approved
0.6364	Remote Similarity	NPD447	Suspended
0.6354	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4749	Approved
0.635	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD3748	Approved
0.6348	Remote Similarity	NPD2799	Discontinued
0.6333	Remote Similarity	NPD7870	Phase 2
0.6333	Remote Similarity	NPD4534	Discontinued
0.6333	Remote Similarity	NPD7871	Phase 2
0.6333	Remote Similarity	NPD5958	Discontinued
0.6333	Remote Similarity	NPD2424	Discontinued
0.6321	Remote Similarity	NPD7701	Phase 2
0.6319	Remote Similarity	NPD2309	Approved
0.6316	Remote Similarity	NPD6823	Phase 2
0.6313	Remote Similarity	NPD5404	Approved
0.6313	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD3303	Discontinued
0.6313	Remote Similarity	NPD5405	Approved
0.6313	Remote Similarity	NPD5408	Approved
0.6313	Remote Similarity	NPD5406	Approved
0.6307	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD4060	Phase 1
0.6307	Remote Similarity	NPD1613	Approved
0.6307	Remote Similarity	NPD943	Approved
0.6302	Remote Similarity	NPD3365	Discontinued
0.6301	Remote Similarity	NPD9494	Approved
0.6298	Remote Similarity	NPD6674	Discontinued
0.6298	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1729	Discontinued
0.6293	Remote Similarity	NPD6312	Discontinued
0.6286	Remote Similarity	NPD411	Approved
0.6286	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7699	Phase 2
0.628	Remote Similarity	NPD7700	Phase 2
0.6278	Remote Similarity	NPD2353	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