NPASS Compound

Structure

NPC476049 OpenBabel07101719152D 24 25 0 0 1 0 0 0 0 0999 V2000 -4.9917 -2.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8748 1.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 -1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5677 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 0.4397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9917 1.0825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 13 1 0 0 0 0 2 14 2 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 9 2 0 0 0 0 6 17 2 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 24 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 6 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 12 1 6 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	359.342
LogP:	2.9
LogD:	2.465
LogS:	-3.995
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	4.994
Fsp3:	0.55
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:	-4.474
MDCK Permeability:	2.4981103706522845e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.178
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.181

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.403
Plasma Protein Binding (PPB):	78.17327117919922%
Volume Distribution (VD):	0.687
Pgp-substrate:	14.771434783935547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.284
CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.24
CYP2C19-substrate:	0.649
CYP2C9-inhibitor:	0.313
CYP2C9-substrate:	0.275
CYP2D6-inhibitor:	0.254
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.402
CYP3A4-substrate:	0.329

ADMET: Excretion

Clearance (CL):	9.143
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.635
AMES Toxicity:	0.155
Rat Oral Acute Toxicity:	0.754
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.491
Carcinogencity:	0.47
Eye Corrosion:	0.003
Eye Irritation:	0.046
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC476049

Natural Product ID:	NPC476049
*Common Name:**	Isoxeniolide A
IUPAC Name:	(4Z,4aS,7E,9R,11aR)-9-hydroxy-4-[(E)-4-hydroxy-4-methylpent-2-enylidene]-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydro-1H-cyclonona[c]pyran-3-one
Synonyms:	Isoxeniolide A
Standard InCHIKey:	ZHNTWXWAMWPYNI-VRKFFOFISA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-13-7-8-16-17(6-5-9-20(3,4)23)19(22)24-12-18(16)14(2)11-15(21)10-13/h5-6,9-10,15-16,18,21,23H,2,7-8,11-12H2,1,3-4H3/b9-5+,13-10+,17-6-/t15-,16+,18-/m0/s1
SMILES:	CC1=CC(CC(=C)C2COC(=O)C(=CC=CC(C)(C)O)C2CC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523377
PubChem CID:	12082166
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO33424	xenia sp.	Species	Xeniidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[12027764]

☑ 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

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	1.0	ug.mL-1	PMID[473789]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[473789]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[473789]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[473789]

☑ 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 NPC476049 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	189
0.1-0.2	945
0.2-0.3	3486
0.3-0.4	6616
0.4-0.5	15424
0.5-0.6	9188
0.6-0.7	5497
0.7-0.8	1304
0.8-0.85	34
0.85-0.9	6
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9551	High Similarity	NPC272050
0.9425	High Similarity	NPC212598
0.914	High Similarity	NPC475053
0.908	High Similarity	NPC234038
0.908	High Similarity	NPC116575
0.907	High Similarity	NPC14575
0.907	High Similarity	NPC196487
0.8989	High Similarity	NPC106040
0.8989	High Similarity	NPC115179
0.875	High Similarity	NPC474369
0.8652	High Similarity	NPC122502
0.8444	Intermediate Similarity	NPC164393
0.8427	Intermediate Similarity	NPC474776
0.837	Intermediate Similarity	NPC295312
0.8352	Intermediate Similarity	NPC160138
0.8333	Intermediate Similarity	NPC137033
0.8316	Intermediate Similarity	NPC107476
0.8316	Intermediate Similarity	NPC304886
0.8315	Intermediate Similarity	NPC53867
0.8315	Intermediate Similarity	NPC250315
0.8295	Intermediate Similarity	NPC325031
0.828	Intermediate Similarity	NPC473448
0.828	Intermediate Similarity	NPC475855
0.828	Intermediate Similarity	NPC476004
0.828	Intermediate Similarity	NPC474761
0.8276	Intermediate Similarity	NPC469617
0.8261	Intermediate Similarity	NPC227379
0.8261	Intermediate Similarity	NPC474471
0.8261	Intermediate Similarity	NPC153805
0.8256	Intermediate Similarity	NPC107668
0.8222	Intermediate Similarity	NPC243618
0.8222	Intermediate Similarity	NPC70424
0.8182	Intermediate Similarity	NPC473596
0.8152	Intermediate Similarity	NPC86005
0.8152	Intermediate Similarity	NPC313658
0.8152	Intermediate Similarity	NPC474765
0.8152	Intermediate Similarity	NPC316138
0.8144	Intermediate Similarity	NPC40812
0.814	Intermediate Similarity	NPC12740
0.814	Intermediate Similarity	NPC61863
0.814	Intermediate Similarity	NPC110461
0.8132	Intermediate Similarity	NPC261380
0.8132	Intermediate Similarity	NPC474547
0.8111	Intermediate Similarity	NPC170377
0.8111	Intermediate Similarity	NPC11620
0.8105	Intermediate Similarity	NPC125674
0.8105	Intermediate Similarity	NPC475838
0.8105	Intermediate Similarity	NPC475912
0.8105	Intermediate Similarity	NPC228451
0.8085	Intermediate Similarity	NPC144133
0.8085	Intermediate Similarity	NPC179394
0.8081	Intermediate Similarity	NPC116139
0.8065	Intermediate Similarity	NPC202672
0.8061	Intermediate Similarity	NPC308567
0.8061	Intermediate Similarity	NPC261377
0.8061	Intermediate Similarity	NPC83895
0.8061	Intermediate Similarity	NPC255592
0.8061	Intermediate Similarity	NPC187761
0.8043	Intermediate Similarity	NPC316426
0.8043	Intermediate Similarity	NPC198314
0.8043	Intermediate Similarity	NPC315395
0.8022	Intermediate Similarity	NPC9868
0.8021	Intermediate Similarity	NPC474247
0.8021	Intermediate Similarity	NPC474338
0.8021	Intermediate Similarity	NPC81386
0.8021	Intermediate Similarity	NPC474035
0.802	Intermediate Similarity	NPC309190
0.8	Intermediate Similarity	NPC30515
0.8	Intermediate Similarity	NPC291500
0.8	Intermediate Similarity	NPC189609
0.8	Intermediate Similarity	NPC197835
0.8	Intermediate Similarity	NPC235369
0.8	Intermediate Similarity	NPC66110
0.8	Intermediate Similarity	NPC303653
0.8	Intermediate Similarity	NPC219874
0.8	Intermediate Similarity	NPC140591
0.7979	Intermediate Similarity	NPC474032
0.7978	Intermediate Similarity	NPC474510
0.7957	Intermediate Similarity	NPC199382
0.7957	Intermediate Similarity	NPC248602
0.7957	Intermediate Similarity	NPC477959
0.7955	Intermediate Similarity	NPC474341
0.7938	Intermediate Similarity	NPC36954
0.7938	Intermediate Similarity	NPC14961
0.7938	Intermediate Similarity	NPC270013
0.7935	Intermediate Similarity	NPC197903
0.7935	Intermediate Similarity	NPC215364
0.7935	Intermediate Similarity	NPC99395
0.7935	Intermediate Similarity	NPC471494
0.7917	Intermediate Similarity	NPC81419
0.7917	Intermediate Similarity	NPC179746
0.7912	Intermediate Similarity	NPC16488
0.79	Intermediate Similarity	NPC62670
0.7895	Intermediate Similarity	NPC51004
0.7889	Intermediate Similarity	NPC8538
0.7889	Intermediate Similarity	NPC184208
0.7889	Intermediate Similarity	NPC315731
0.7879	Intermediate Similarity	NPC475653
0.7879	Intermediate Similarity	NPC187268
0.7879	Intermediate Similarity	NPC203627
0.7879	Intermediate Similarity	NPC244411
0.7879	Intermediate Similarity	NPC23364
0.7872	Intermediate Similarity	NPC281516
0.7865	Intermediate Similarity	NPC139712
0.7857	Intermediate Similarity	NPC230800
0.7857	Intermediate Similarity	NPC473291
0.7857	Intermediate Similarity	NPC476315
0.7857	Intermediate Similarity	NPC202833
0.7857	Intermediate Similarity	NPC279621
0.7849	Intermediate Similarity	NPC311163
0.7849	Intermediate Similarity	NPC475461
0.7849	Intermediate Similarity	NPC305475
0.7849	Intermediate Similarity	NPC284902
0.7843	Intermediate Similarity	NPC239162
0.7835	Intermediate Similarity	NPC71589
0.7835	Intermediate Similarity	NPC477131
0.7835	Intermediate Similarity	NPC469491
0.7826	Intermediate Similarity	NPC72464
0.7826	Intermediate Similarity	NPC472957
0.7826	Intermediate Similarity	NPC472958
0.7822	Intermediate Similarity	NPC478156
0.7812	Intermediate Similarity	NPC470379
0.7812	Intermediate Similarity	NPC12172
0.7812	Intermediate Similarity	NPC111114
0.7812	Intermediate Similarity	NPC472705
0.7812	Intermediate Similarity	NPC470373
0.7812	Intermediate Similarity	NPC208886
0.7812	Intermediate Similarity	NPC184463
0.7812	Intermediate Similarity	NPC300312
0.7812	Intermediate Similarity	NPC475972
0.7812	Intermediate Similarity	NPC261607
0.7802	Intermediate Similarity	NPC85772
0.7802	Intermediate Similarity	NPC475936
0.7802	Intermediate Similarity	NPC474291
0.78	Intermediate Similarity	NPC288876
0.7791	Intermediate Similarity	NPC135703
0.7789	Intermediate Similarity	NPC307411
0.7778	Intermediate Similarity	NPC233377
0.7778	Intermediate Similarity	NPC120299
0.7778	Intermediate Similarity	NPC471462
0.7766	Intermediate Similarity	NPC312561
0.7766	Intermediate Similarity	NPC475703
0.7757	Intermediate Similarity	NPC469454
0.7757	Intermediate Similarity	NPC469496
0.7757	Intermediate Similarity	NPC469463
0.7755	Intermediate Similarity	NPC209355
0.7755	Intermediate Similarity	NPC300710
0.7753	Intermediate Similarity	NPC267231
0.7753	Intermediate Similarity	NPC93763
0.7753	Intermediate Similarity	NPC108816
0.7745	Intermediate Similarity	NPC475945
0.7745	Intermediate Similarity	NPC475871
0.7742	Intermediate Similarity	NPC21469
0.7742	Intermediate Similarity	NPC255307
0.7736	Intermediate Similarity	NPC179798
0.7736	Intermediate Similarity	NPC304180
0.7732	Intermediate Similarity	NPC109406
0.7732	Intermediate Similarity	NPC212486
0.7732	Intermediate Similarity	NPC159092
0.7732	Intermediate Similarity	NPC476300
0.7732	Intermediate Similarity	NPC135776
0.7723	Intermediate Similarity	NPC150923
0.7723	Intermediate Similarity	NPC471412
0.7723	Intermediate Similarity	NPC474742
0.7723	Intermediate Similarity	NPC146822
0.7717	Intermediate Similarity	NPC52609
0.7717	Intermediate Similarity	NPC44261
0.7717	Intermediate Similarity	NPC1761
0.7717	Intermediate Similarity	NPC475842
0.7708	Intermediate Similarity	NPC313670
0.7708	Intermediate Similarity	NPC62815
0.7708	Intermediate Similarity	NPC281942
0.7708	Intermediate Similarity	NPC71533
0.7708	Intermediate Similarity	NPC232426
0.7708	Intermediate Similarity	NPC106510
0.7708	Intermediate Similarity	NPC77337
0.77	Intermediate Similarity	NPC64742
0.77	Intermediate Similarity	NPC316598
0.77	Intermediate Similarity	NPC161855
0.7692	Intermediate Similarity	NPC42470
0.7692	Intermediate Similarity	NPC112868
0.7677	Intermediate Similarity	NPC234993
0.7677	Intermediate Similarity	NPC9812
0.7677	Intermediate Similarity	NPC134072
0.7677	Intermediate Similarity	NPC255410
0.7664	Intermediate Similarity	NPC66108
0.766	Intermediate Similarity	NPC61527
0.766	Intermediate Similarity	NPC261721
0.7653	Intermediate Similarity	NPC262133
0.7653	Intermediate Similarity	NPC198853
0.7653	Intermediate Similarity	NPC470010
0.7653	Intermediate Similarity	NPC303942
0.7653	Intermediate Similarity	NPC475832
0.7653	Intermediate Similarity	NPC57405
0.7653	Intermediate Similarity	NPC475927
0.7653	Intermediate Similarity	NPC470013
0.7653	Intermediate Similarity	NPC323008
0.7653	Intermediate Similarity	NPC475572
0.7647	Intermediate Similarity	NPC86077
0.7647	Intermediate Similarity	NPC273005

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 NPC476049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1230
0.2-0.3	3254
0.3-0.4	2685
0.4-0.5	1217
0.5-0.6	436
0.6-0.7	148
0.7-0.8	15
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
0.7917	Intermediate Similarity	NPD5778	Approved
0.7917	Intermediate Similarity	NPD5779	Approved
0.7895	Intermediate Similarity	NPD6698	Approved
0.7895	Intermediate Similarity	NPD46	Approved
0.7879	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7838	Discovery
0.7629	Intermediate Similarity	NPD7983	Approved
0.75	Intermediate Similarity	NPD7839	Suspended
0.7423	Intermediate Similarity	NPD6101	Approved
0.7423	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5785	Approved
0.7282	Intermediate Similarity	NPD6648	Approved
0.7273	Intermediate Similarity	NPD6411	Approved
0.7228	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5344	Discontinued
0.7188	Intermediate Similarity	NPD5363	Approved
0.7158	Intermediate Similarity	NPD5362	Discontinued
0.7158	Intermediate Similarity	NPD7154	Phase 3
0.7156	Intermediate Similarity	NPD6371	Approved
0.713	Intermediate Similarity	NPD6686	Approved
0.7115	Intermediate Similarity	NPD7640	Approved
0.7115	Intermediate Similarity	NPD7639	Approved
0.7053	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6053	Discontinued
0.7019	Intermediate Similarity	NPD7638	Approved
0.701	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5282	Discontinued
0.6939	Remote Similarity	NPD4249	Approved
0.6939	Remote Similarity	NPD5786	Approved
0.6937	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7637	Suspended
0.69	Remote Similarity	NPD1695	Approved
0.6882	Remote Similarity	NPD4756	Discovery
0.6875	Remote Similarity	NPD4269	Approved
0.6875	Remote Similarity	NPD4270	Approved
0.6875	Remote Similarity	NPD5209	Approved
0.6869	Remote Similarity	NPD4251	Approved
0.6869	Remote Similarity	NPD4250	Approved
0.6857	Remote Similarity	NPD4225	Approved
0.6848	Remote Similarity	NPD8039	Approved
0.6842	Remote Similarity	NPD4822	Approved
0.6842	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4821	Approved
0.6842	Remote Similarity	NPD4820	Approved
0.6842	Remote Similarity	NPD4819	Approved
0.6838	Remote Similarity	NPD8516	Approved
0.6838	Remote Similarity	NPD8515	Approved
0.6838	Remote Similarity	NPD8517	Approved
0.6838	Remote Similarity	NPD8513	Phase 3
0.6837	Remote Similarity	NPD1694	Approved
0.6818	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5369	Approved
0.6701	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6638	Remote Similarity	NPD7115	Discovery
0.6633	Remote Similarity	NPD5332	Approved
0.6633	Remote Similarity	NPD5331	Approved
0.6632	Remote Similarity	NPD4271	Approved
0.6632	Remote Similarity	NPD4268	Approved
0.6598	Remote Similarity	NPD4790	Discontinued
0.6591	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7830	Approved
0.6583	Remote Similarity	NPD7829	Approved
0.6557	Remote Similarity	NPD8074	Phase 3
0.6514	Remote Similarity	NPD7632	Discontinued
0.65	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5368	Approved
0.648	Remote Similarity	NPD7260	Phase 2
0.6475	Remote Similarity	NPD8273	Phase 1
0.6465	Remote Similarity	NPD6695	Phase 3
0.6465	Remote Similarity	NPD6110	Phase 1
0.646	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6647	Phase 2
0.6441	Remote Similarity	NPD7641	Discontinued
0.6429	Remote Similarity	NPD5697	Approved
0.64	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4632	Approved
0.6373	Remote Similarity	NPD3573	Approved
0.6372	Remote Similarity	NPD6899	Approved
0.6372	Remote Similarity	NPD6881	Approved
0.6372	Remote Similarity	NPD6011	Approved
0.6357	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7500	Approved
0.6348	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8451	Approved
0.6341	Remote Similarity	NPD7507	Approved
0.6337	Remote Similarity	NPD1696	Phase 3
0.6333	Remote Similarity	NPD7331	Phase 2
0.6322	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7748	Approved
0.6316	Remote Similarity	NPD6013	Approved
0.6316	Remote Similarity	NPD6014	Approved
0.6316	Remote Similarity	NPD6012	Approved
0.6311	Remote Similarity	NPD7642	Approved
0.6296	Remote Similarity	NPD6083	Phase 2
0.6296	Remote Similarity	NPD6084	Phase 2
0.629	Remote Similarity	NPD8448	Approved
0.6286	Remote Similarity	NPD5281	Approved
0.6286	Remote Similarity	NPD7515	Phase 2
0.6286	Remote Similarity	NPD5284	Approved
0.6281	Remote Similarity	NPD8444	Approved
0.6281	Remote Similarity	NPD7503	Approved
0.6275	Remote Similarity	NPD6422	Discontinued
0.6275	Remote Similarity	NPD5279	Phase 3
0.6262	Remote Similarity	NPD5695	Phase 3
0.6261	Remote Similarity	NPD6883	Approved
0.6261	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7102	Approved
0.6261	Remote Similarity	NPD7290	Approved
0.626	Remote Similarity	NPD8299	Approved
0.626	Remote Similarity	NPD8342	Approved
0.626	Remote Similarity	NPD8341	Approved
0.626	Remote Similarity	NPD8340	Approved
0.6228	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6399	Phase 3
0.6222	Remote Similarity	NPD7341	Phase 2
0.6218	Remote Similarity	NPD6009	Approved
0.6216	Remote Similarity	NPD5211	Phase 2
0.6214	Remote Similarity	NPD7524	Approved
0.6214	Remote Similarity	NPD7750	Discontinued
0.6207	Remote Similarity	NPD6869	Approved
0.6207	Remote Similarity	NPD6617	Approved
0.6207	Remote Similarity	NPD6649	Approved
0.6207	Remote Similarity	NPD6650	Approved
0.6207	Remote Similarity	NPD6847	Approved
0.6207	Remote Similarity	NPD8130	Phase 1
0.6198	Remote Similarity	NPD6319	Approved
0.6195	Remote Similarity	NPD6675	Approved
0.6195	Remote Similarity	NPD7128	Approved
0.6195	Remote Similarity	NPD6402	Approved
0.6195	Remote Similarity	NPD5048	Discontinued
0.6195	Remote Similarity	NPD6008	Approved
0.6195	Remote Similarity	NPD5739	Approved
0.619	Remote Similarity	NPD7319	Approved
0.6162	Remote Similarity	NPD7514	Phase 3
0.6162	Remote Similarity	NPD7332	Phase 2
0.6162	Remote Similarity	NPD6931	Approved
0.6162	Remote Similarity	NPD4695	Discontinued
0.6162	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6930	Phase 2
0.6154	Remote Similarity	NPD6882	Approved
0.6154	Remote Similarity	NPD8297	Approved
0.6148	Remote Similarity	NPD5983	Phase 2
0.6147	Remote Similarity	NPD7902	Approved
0.6142	Remote Similarity	NPD8392	Approved
0.6142	Remote Similarity	NPD8391	Approved
0.6142	Remote Similarity	NPD8390	Approved
0.614	Remote Similarity	NPD5701	Approved
0.614	Remote Similarity	NPD6412	Phase 2
0.6132	Remote Similarity	NPD5694	Approved
0.6132	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6079	Approved
0.6132	Remote Similarity	NPD5693	Phase 1
0.6117	Remote Similarity	NPD5330	Approved
0.6117	Remote Similarity	NPD4623	Approved
0.6117	Remote Similarity	NPD4519	Discontinued
0.6117	Remote Similarity	NPD7334	Approved
0.6117	Remote Similarity	NPD7146	Approved
0.6117	Remote Similarity	NPD6409	Approved
0.6117	Remote Similarity	NPD6684	Approved
0.6117	Remote Similarity	NPD7521	Approved
0.6106	Remote Similarity	NPD5909	Discontinued
0.6106	Remote Similarity	NPD5141	Approved
0.6095	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5370	Suspended
0.6091	Remote Similarity	NPD5696	Approved
0.6087	Remote Similarity	NPD7320	Approved
0.6078	Remote Similarity	NPD3665	Phase 1
0.6078	Remote Similarity	NPD3666	Approved
0.6078	Remote Similarity	NPD3133	Approved
0.6061	Remote Similarity	NPD6929	Approved
0.6055	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5222	Approved
0.6055	Remote Similarity	NPD5221	Approved
0.6048	Remote Similarity	NPD7604	Phase 2
0.6047	Remote Similarity	NPD6845	Suspended
0.604	Remote Similarity	NPD3667	Approved
0.6038	Remote Similarity	NPD5207	Approved
0.6038	Remote Similarity	NPD5692	Phase 3
0.6036	Remote Similarity	NPD5286	Approved
0.6036	Remote Similarity	NPD4696	Approved
0.6036	Remote Similarity	NPD5285	Approved
0.6034	Remote Similarity	NPD6372	Approved
0.6034	Remote Similarity	NPD6373	Approved
0.6016	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6685	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4518	Approved
0.5982	Remote Similarity	NPD5223	Approved
0.5981	Remote Similarity	NPD6050	Approved
0.5981	Remote Similarity	NPD7087	Discontinued

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