NPASS Compound

Structure

NPC223063 OpenBabel07101719252D 26 29 0 0 1 0 0 0 0 0999 V2000 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 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 1 15 1 0 0 0 0 4 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 19 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 21 1 0 0 0 0 11 16 2 0 0 0 0 11 25 1 0 0 0 0 12 17 2 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 23 1 0 0 0 0 14 26 1 0 0 0 0 15 24 2 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 6 0 0 0 18 22 1 0 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 20 2 1 1 0 0 0 21 3 1 6 0 0 0 22 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	382.094
LogP:	3.479
LogD:	2.984
LogS:	-3.655
# Rotatable Bonds:	4
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.819
Synthetic Accessibility Score:	4.61
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.782
MDCK Permeability:	1.9802022507064976e-05
Pgp-inhibitor:	0.926
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.796
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.298
Plasma Protein Binding (PPB):	93.24102020263672%
Volume Distribution (VD):	1.358
Pgp-substrate:	4.467045307159424%

ADMET: Metabolism

CYP1A2-inhibitor:	0.177
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.386
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.657
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	8.838
Half-life (T1/2):	0.361

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.54
Drug-inuced Liver Injury (DILI):	0.223
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.497
Skin Sensitization:	0.406
Carcinogencity:	0.945
Eye Corrosion:	0.004
Eye Irritation:	0.06
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC223063

Natural Product ID:	NPC223063
*Common Name:**	20-Acetoxy-19-Hydroxyspongia-13(16),14-Diene
IUPAC Name:	[(3bR,5aS,6S,9aS,9bS)-6-(hydroxymethyl)-3b,6-dimethyl-5,5a,7,8,9,9b,10,11-octahydro-4H-naphtho[2,1-e][2]benzofuran-9a-yl]methyl acetate
Synonyms:
Standard InCHIKey:	SMXDQQCBDPYKBT-BIRZXAFVSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-15(24)26-14-22-9-4-8-20(2,13-23)18(22)7-10-21(3)17-12-25-11-16(17)5-6-19(21)22/h11-12,18-19,23H,4-10,13-14H2,1-3H3/t18-,19-,20+,21-,22+/m0/s1
SMILES:	CC(=O)OC[C@]12CCC[C@](C)(CO)[C@@H]1CC[C@@]1(C)c3cocc3CC[C@H]21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512825
PubChem CID:	24878743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002550] Isocopalane and spongiane diterpenoids

*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
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tongoa, Vanuatu Islands	1996	PMID[10757711]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662110]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497946]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tong-Yong City in the South Sea, Korea	n.a.	PMID[16905319]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17567172]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988093]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18407692]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[24992702]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3511	Individual Protein	Thyrotropin-releasing hormone receptor 2	Rattus norvegicus	IC50	=	23000.0	nM	PMID[522959]

☑ 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 NPC223063 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	225
0.1-0.2	1224
0.2-0.3	2683
0.3-0.4	5891
0.4-0.5	12045
0.5-0.6	13562
0.6-0.7	6221
0.7-0.8	689
0.8-0.85	114
0.85-0.9	29
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC120836
0.9669	High Similarity	NPC230979
0.9587	High Similarity	NPC130275
0.9504	High Similarity	NPC272899
0.9421	High Similarity	NPC36255
0.9365	High Similarity	NPC89133
0.935	High Similarity	NPC303010
0.9268	High Similarity	NPC83115
0.9147	High Similarity	NPC471998
0.9055	High Similarity	NPC198904
0.9008	High Similarity	NPC212918
0.8992	High Similarity	NPC471995
0.8968	High Similarity	NPC138139
0.8968	High Similarity	NPC46536
0.8832	High Similarity	NPC41182
0.8828	High Similarity	NPC207294
0.8828	High Similarity	NPC112706
0.8797	High Similarity	NPC310043
0.8797	High Similarity	NPC4764
0.875	High Similarity	NPC83178
0.874	High Similarity	NPC179354
0.873	High Similarity	NPC16922
0.8722	High Similarity	NPC214572
0.8705	High Similarity	NPC216755
0.8692	High Similarity	NPC476925
0.8682	High Similarity	NPC476917
0.8682	High Similarity	NPC327527
0.8672	High Similarity	NPC23086
0.8672	High Similarity	NPC74612
0.8667	High Similarity	NPC90953
0.8613	High Similarity	NPC121158
0.8593	High Similarity	NPC471996
0.8571	High Similarity	NPC471174
0.8538	High Similarity	NPC477040
0.8529	High Similarity	NPC202260
0.8504	High Similarity	NPC477967
0.8478	Intermediate Similarity	NPC20578
0.8478	Intermediate Similarity	NPC62103
0.8467	Intermediate Similarity	NPC67003
0.8403	Intermediate Similarity	NPC294511
0.8403	Intermediate Similarity	NPC121615
0.8403	Intermediate Similarity	NPC472672
0.8397	Intermediate Similarity	NPC477966
0.8397	Intermediate Similarity	NPC329707
0.8397	Intermediate Similarity	NPC477123
0.8392	Intermediate Similarity	NPC212257
0.837	Intermediate Similarity	NPC476947
0.8357	Intermediate Similarity	NPC476944
0.8357	Intermediate Similarity	NPC251865
0.8346	Intermediate Similarity	NPC61788
0.8345	Intermediate Similarity	NPC237259
0.8345	Intermediate Similarity	NPC302054
0.8345	Intermediate Similarity	NPC98206
0.8345	Intermediate Similarity	NPC34421
0.8345	Intermediate Similarity	NPC253201
0.8322	Intermediate Similarity	NPC125182
0.8322	Intermediate Similarity	NPC69647
0.8322	Intermediate Similarity	NPC472654
0.831	Intermediate Similarity	NPC255414
0.831	Intermediate Similarity	NPC250228
0.8309	Intermediate Similarity	NPC46896
0.8286	Intermediate Similarity	NPC103134
0.8276	Intermediate Similarity	NPC469503
0.8264	Intermediate Similarity	NPC228842
0.8258	Intermediate Similarity	NPC477039
0.8254	Intermediate Similarity	NPC144745
0.8254	Intermediate Similarity	NPC208906
0.8252	Intermediate Similarity	NPC476942
0.8252	Intermediate Similarity	NPC476941
0.8252	Intermediate Similarity	NPC471007
0.8248	Intermediate Similarity	NPC307401
0.8235	Intermediate Similarity	NPC158525
0.8231	Intermediate Similarity	NPC243269
0.8222	Intermediate Similarity	NPC293253
0.8222	Intermediate Similarity	NPC218838
0.8219	Intermediate Similarity	NPC178932
0.8214	Intermediate Similarity	NPC263337
0.8207	Intermediate Similarity	NPC272590
0.8201	Intermediate Similarity	NPC148374
0.8201	Intermediate Similarity	NPC56197
0.8194	Intermediate Similarity	NPC234494
0.8194	Intermediate Similarity	NPC195325
0.8188	Intermediate Similarity	NPC476943
0.8182	Intermediate Similarity	NPC476937
0.8182	Intermediate Similarity	NPC71821
0.8182	Intermediate Similarity	NPC476938
0.8176	Intermediate Similarity	NPC194499
0.8169	Intermediate Similarity	NPC5676
0.8163	Intermediate Similarity	NPC141538
0.8163	Intermediate Similarity	NPC35000
0.8163	Intermediate Similarity	NPC469336
0.8163	Intermediate Similarity	NPC296807
0.8163	Intermediate Similarity	NPC155939
0.8163	Intermediate Similarity	NPC92979
0.8156	Intermediate Similarity	NPC267632
0.8156	Intermediate Similarity	NPC243577
0.8151	Intermediate Similarity	NPC246164
0.814	Intermediate Similarity	NPC97566
0.8138	Intermediate Similarity	NPC470997
0.8121	Intermediate Similarity	NPC474611
0.8116	Intermediate Similarity	NPC310830
0.8116	Intermediate Similarity	NPC42400
0.8108	Intermediate Similarity	NPC41880
0.8095	Intermediate Similarity	NPC30222
0.8095	Intermediate Similarity	NPC150895
0.8095	Intermediate Similarity	NPC282445
0.8092	Intermediate Similarity	NPC178382
0.8092	Intermediate Similarity	NPC477965
0.8092	Intermediate Similarity	NPC477038
0.8077	Intermediate Similarity	NPC317217
0.8074	Intermediate Similarity	NPC298190
0.8069	Intermediate Similarity	NPC211625
0.8067	Intermediate Similarity	NPC335761
0.8054	Intermediate Similarity	NPC195954
0.8054	Intermediate Similarity	NPC7059
0.8054	Intermediate Similarity	NPC304692
0.8054	Intermediate Similarity	NPC88007
0.8054	Intermediate Similarity	NPC472772
0.8045	Intermediate Similarity	NPC290955
0.8043	Intermediate Similarity	NPC146872
0.8042	Intermediate Similarity	NPC185456
0.8028	Intermediate Similarity	NPC476946
0.8027	Intermediate Similarity	NPC475777
0.8027	Intermediate Similarity	NPC75906
0.8027	Intermediate Similarity	NPC33938
0.8015	Intermediate Similarity	NPC471817
0.8014	Intermediate Similarity	NPC205765
0.8013	Intermediate Similarity	NPC470792
0.8013	Intermediate Similarity	NPC79571
0.8	Intermediate Similarity	NPC93666
0.7987	Intermediate Similarity	NPC104736
0.7986	Intermediate Similarity	NPC346
0.7985	Intermediate Similarity	NPC26532
0.7973	Intermediate Similarity	NPC114880
0.7973	Intermediate Similarity	NPC57998
0.7972	Intermediate Similarity	NPC142113
0.7972	Intermediate Similarity	NPC199044
0.7972	Intermediate Similarity	NPC238843
0.7971	Intermediate Similarity	NPC92941
0.7961	Intermediate Similarity	NPC39986
0.7961	Intermediate Similarity	NPC302369
0.7961	Intermediate Similarity	NPC134254
0.7958	Intermediate Similarity	NPC52412
0.7956	Intermediate Similarity	NPC470740
0.7947	Intermediate Similarity	NPC8389
0.7945	Intermediate Similarity	NPC471001
0.7943	Intermediate Similarity	NPC90296
0.7933	Intermediate Similarity	NPC475066
0.7933	Intermediate Similarity	NPC214495
0.7933	Intermediate Similarity	NPC45101
0.7933	Intermediate Similarity	NPC470119
0.7933	Intermediate Similarity	NPC249021
0.7931	Intermediate Similarity	NPC302987
0.7931	Intermediate Similarity	NPC470941
0.7929	Intermediate Similarity	NPC220094
0.7926	Intermediate Similarity	NPC208389
0.7919	Intermediate Similarity	NPC75310
0.7919	Intermediate Similarity	NPC264943
0.7919	Intermediate Similarity	NPC281258
0.791	Intermediate Similarity	NPC474830
0.791	Intermediate Similarity	NPC471554
0.791	Intermediate Similarity	NPC473355
0.791	Intermediate Similarity	NPC471501
0.791	Intermediate Similarity	NPC471573
0.791	Intermediate Similarity	NPC476016
0.791	Intermediate Similarity	NPC246392
0.7907	Intermediate Similarity	NPC243704
0.7905	Intermediate Similarity	NPC268905
0.7905	Intermediate Similarity	NPC476939
0.7905	Intermediate Similarity	NPC476940
0.7902	Intermediate Similarity	NPC64568
0.7895	Intermediate Similarity	NPC207978
0.7895	Intermediate Similarity	NPC18986
0.7895	Intermediate Similarity	NPC263432
0.7895	Intermediate Similarity	NPC474829
0.7895	Intermediate Similarity	NPC5079
0.7895	Intermediate Similarity	NPC68848
0.7895	Intermediate Similarity	NPC472771
0.7895	Intermediate Similarity	NPC69028
0.7895	Intermediate Similarity	NPC200782
0.7891	Intermediate Similarity	NPC196846
0.7891	Intermediate Similarity	NPC159927
0.7891	Intermediate Similarity	NPC476122
0.7891	Intermediate Similarity	NPC469335
0.7891	Intermediate Similarity	NPC477404
0.7891	Intermediate Similarity	NPC196864
0.7887	Intermediate Similarity	NPC20500
0.7883	Intermediate Similarity	NPC473982
0.7881	Intermediate Similarity	NPC307383
0.7881	Intermediate Similarity	NPC140952
0.7881	Intermediate Similarity	NPC475226
0.7881	Intermediate Similarity	NPC472671
0.7881	Intermediate Similarity	NPC262872
0.7881	Intermediate Similarity	NPC475967
0.7862	Intermediate Similarity	NPC471292
0.7862	Intermediate Similarity	NPC62799
0.7857	Intermediate Similarity	NPC215109
0.7857	Intermediate Similarity	NPC170604
0.7857	Intermediate Similarity	NPC470742
0.7857	Intermediate Similarity	NPC186626

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 NPC223063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	928
0.2-0.3	1848
0.3-0.4	2739
0.4-0.5	2154
0.5-0.6	1052
0.6-0.7	210
0.7-0.8	9
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
0.7919	Intermediate Similarity	NPD5760	Phase 2
0.7919	Intermediate Similarity	NPD5761	Phase 2
0.7622	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6273	Approved
0.7466	Intermediate Similarity	NPD4628	Phase 3
0.7195	Intermediate Similarity	NPD6765	Approved
0.7195	Intermediate Similarity	NPD6764	Approved
0.7186	Intermediate Similarity	NPD8434	Phase 2
0.7162	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD8032	Phase 2
0.7114	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7003	Approved
0.7113	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4140	Approved
0.7078	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2346	Discontinued
0.7024	Intermediate Similarity	NPD6784	Approved
0.7024	Intermediate Similarity	NPD6785	Approved
0.7007	Intermediate Similarity	NPD2799	Discontinued
0.6978	Remote Similarity	NPD1608	Approved
0.6968	Remote Similarity	NPD7458	Discontinued
0.6957	Remote Similarity	NPD8127	Discontinued
0.695	Remote Similarity	NPD2797	Approved
0.6944	Remote Similarity	NPD2313	Discontinued
0.6944	Remote Similarity	NPD3764	Approved
0.6918	Remote Similarity	NPD6355	Discontinued
0.6913	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6005	Phase 3
0.6913	Remote Similarity	NPD6004	Phase 3
0.6913	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6002	Phase 3
0.6899	Remote Similarity	NPD7819	Suspended
0.6859	Remote Similarity	NPD3226	Approved
0.6846	Remote Similarity	NPD1551	Phase 2
0.6828	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3268	Approved
0.6818	Remote Similarity	NPD2533	Approved
0.6818	Remote Similarity	NPD2532	Approved
0.6818	Remote Similarity	NPD2534	Approved
0.6813	Remote Similarity	NPD7768	Phase 2
0.6806	Remote Similarity	NPD6832	Phase 2
0.6779	Remote Similarity	NPD4308	Phase 3
0.6776	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4110	Phase 3
0.6776	Remote Similarity	NPD3750	Approved
0.6763	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1778	Approved
0.6763	Remote Similarity	NPD17	Approved
0.6761	Remote Similarity	NPD1283	Approved
0.6759	Remote Similarity	NPD7095	Approved
0.675	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6099	Approved
0.6733	Remote Similarity	NPD6100	Approved
0.6712	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6798	Discontinued
0.6709	Remote Similarity	NPD6599	Discontinued
0.6691	Remote Similarity	NPD5585	Approved
0.6691	Remote Similarity	NPD5951	Approved
0.6689	Remote Similarity	NPD5735	Approved
0.6689	Remote Similarity	NPD5763	Approved
0.6689	Remote Similarity	NPD5762	Approved
0.6688	Remote Similarity	NPD7236	Approved
0.6687	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD7411	Suspended
0.6646	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7008	Discontinued
0.6625	Remote Similarity	NPD37	Approved
0.6624	Remote Similarity	NPD920	Approved
0.6623	Remote Similarity	NPD4477	Approved
0.6623	Remote Similarity	NPD4476	Approved
0.6622	Remote Similarity	NPD4307	Phase 2
0.6622	Remote Similarity	NPD2979	Phase 3
0.6621	Remote Similarity	NPD5736	Approved
0.662	Remote Similarity	NPD3972	Approved
0.6619	Remote Similarity	NPD1894	Discontinued
0.6607	Remote Similarity	NPD5844	Phase 1
0.6605	Remote Similarity	NPD4966	Approved
0.6605	Remote Similarity	NPD4965	Approved
0.6605	Remote Similarity	NPD4967	Phase 2
0.6601	Remote Similarity	NPD2800	Approved
0.6597	Remote Similarity	NPD3266	Approved
0.6597	Remote Similarity	NPD3267	Approved
0.6581	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7440	Discontinued
0.6579	Remote Similarity	NPD2344	Approved
0.6579	Remote Similarity	NPD1471	Phase 3
0.6573	Remote Similarity	NPD5327	Phase 3
0.6564	Remote Similarity	NPD7075	Discontinued
0.6562	Remote Similarity	NPD6677	Suspended
0.6554	Remote Similarity	NPD6233	Phase 2
0.6549	Remote Similarity	NPD1281	Approved
0.6548	Remote Similarity	NPD7177	Discontinued
0.6536	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD1876	Approved
0.6519	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD2935	Discontinued
0.6512	Remote Similarity	NPD8312	Approved
0.6512	Remote Similarity	NPD8313	Approved
0.6506	Remote Similarity	NPD7229	Phase 3
0.6503	Remote Similarity	NPD9717	Approved
0.6497	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1243	Approved
0.6493	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7097	Phase 1
0.6486	Remote Similarity	NPD7985	Registered
0.6486	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD1203	Approved
0.6483	Remote Similarity	NPD6362	Approved
0.6481	Remote Similarity	NPD8455	Phase 2
0.6478	Remote Similarity	NPD7239	Suspended
0.6471	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5124	Phase 1
0.6467	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD2614	Approved
0.6458	Remote Similarity	NPD4359	Approved
0.645	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7199	Phase 2
0.6438	Remote Similarity	NPD5647	Approved
0.6434	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6799	Approved
0.6429	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4534	Discontinued
0.6424	Remote Similarity	NPD6653	Approved
0.6424	Remote Similarity	NPD6651	Approved
0.6424	Remote Similarity	NPD6353	Approved
0.6424	Remote Similarity	NPD6234	Discontinued
0.6423	Remote Similarity	NPD5535	Approved
0.642	Remote Similarity	NPD6801	Discontinued
0.6415	Remote Similarity	NPD5403	Approved
0.6415	Remote Similarity	NPD7427	Discontinued
0.6415	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD3225	Approved
0.641	Remote Similarity	NPD2309	Approved
0.6408	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD2438	Suspended
0.6405	Remote Similarity	NPD2531	Phase 2
0.6405	Remote Similarity	NPD2796	Approved
0.6403	Remote Similarity	NPD7157	Approved
0.6402	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4060	Phase 1
0.6398	Remote Similarity	NPD7028	Phase 2
0.6392	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5401	Approved
0.6391	Remote Similarity	NPD7473	Discontinued
0.6383	Remote Similarity	NPD9545	Approved
0.6377	Remote Similarity	NPD1241	Discontinued
0.637	Remote Similarity	NPD2182	Approved
0.6364	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3496	Discontinued
0.6364	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4622	Approved
0.6358	Remote Similarity	NPD4618	Approved
0.6353	Remote Similarity	NPD7228	Approved
0.6347	Remote Similarity	NPD6959	Discontinued
0.6346	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD5691	Approved
0.6333	Remote Similarity	NPD4062	Phase 3
0.6331	Remote Similarity	NPD2629	Approved
0.6327	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD919	Approved
0.6323	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD1549	Phase 2
0.6323	Remote Similarity	NPD5958	Discontinued
0.6312	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7315	Approved
0.631	Remote Similarity	NPD5710	Approved
0.631	Remote Similarity	NPD5711	Approved
0.631	Remote Similarity	NPD6232	Discontinued
0.6301	Remote Similarity	NPD8651	Approved
0.6301	Remote Similarity	NPD6696	Suspended
0.6294	Remote Similarity	NPD3019	Approved
0.6294	Remote Similarity	NPD4626	Approved
0.6286	Remote Similarity	NPD4198	Discontinued
0.6282	Remote Similarity	NPD6674	Discontinued
0.628	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD1481	Phase 2
0.6275	Remote Similarity	NPD5689	Approved
0.6275	Remote Similarity	NPD5688	Approved
0.6272	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7693	Approved
0.6268	Remote Similarity	NPD7741	Discontinued
0.6267	Remote Similarity	NPD411	Approved
0.6267	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD6667	Approved
0.6266	Remote Similarity	NPD6666	Approved
0.6259	Remote Similarity	NPD1049	Clinical (unspecified phase)

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