NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	449.24
Volume:	459.963
LogP:	5.534
LogD:	4.848
LogS:	-6.295
# Rotatable Bonds:	5
TPSA:	79.57
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	4.76
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.034
MDCK Permeability:	2.3394559320877306e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	96.75790405273438%
Volume Distribution (VD):	1.989
Pgp-substrate:	1.6180849075317383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.242
CYP2C19-inhibitor:	0.381
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.507
CYP2C9-substrate:	0.231
CYP2D6-inhibitor:	0.222
CYP2D6-substrate:	0.668
CYP3A4-inhibitor:	0.665
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	3.436
Half-life (T1/2):	0.038

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.909
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.303
Carcinogencity:	0.962
Eye Corrosion:	0.007
Eye Irritation:	0.046
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC476917

Natural Product ID:	NPC476917
*Common Name:**	[(E)-[(1R,4aR,4bS,8aS,10aS)-1-[2-(furan-3-yl)ethyl]-4b,8,8,10a-tetramethyl-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-2-ylidene]methyl] sulfate;2-(dimethylamino)-1,3,7,9-tetramethyl-8H-purin-3-ium-6-one
IUPAC Name:	[(E)-[(1R,4aR,4bS,8aS,10aS)-1-[2-(furan-3-yl)ethyl]-4b,8,8,10a-tetramethyl-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-2-ylidene]methyl] sulfate;2-(dimethylamino)-1,3,7,9-tetramethyl-8H-purin-3-ium-6-one
Synonyms:
Standard InCHIKey:	ZQFUWPRQPCRAAQ-VNINRLMRSA-M
Standard InCHI:	InChI=1S/C25H38O5S.C11H20N5O/c1-23(2)12-5-13-25(4)21(23)10-14-24(3)20(8-6-18-11-15-29-16-18)19(7-9-22(24)25)17-30-31(26,27)28;1-12(2)11-15(5)9-8(10(17)16(11)6)13(3)7-14(9)4/h11,15-17,20-22H,5-10,12-14H2,1-4H3,(H,26,27,28);7H2,1-6H3/q;+1/p-1/b19-17+;/t20-,21-,22-,24+,25-;/m0./s1
SMILES:	C[C@]12CCCC([C@@H]1CC[C@]3([C@@H]2CC/C(=C\OS(=O)(=O)[O-])/[C@@H]3CCC4=COC=C4)C)(C)C.CN1CN(C2=C1C(=O)N(C(=[N+]2C)N(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90683055
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO33616	Coscinoderma sp.	Species	Spongiidae	Eukaryota	n.a.	at a depth of 15 m off the coast of Weno Island, Chuuk state, Micronesia	2010-FEB	PMID[24828374]
NPO33616	Coscinoderma sp.	Species	Spongiidae	Eukaryota	n.a.	at a depth of 15 m off the coast of Weno Island, Chuuk state, Federated States of Micronesia	2010-FEB	PMID[24828374]

☑ 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
MIC	8
Others	2

Activity Type	# Activity
Cell Line	2
Organism	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	LC50	=	1.9	ug/ml	PMID[24828374]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	2.2	ug/ml	PMID[24828374]
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	MIC	=	0.78	ug/ml	PMID[24828374]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	0.78	ug/ml	PMID[24828374]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug/ml	PMID[24828374]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	6.25	ug/ml	PMID[24828374]
NPT2	Others	Unspecified		MIC	=	6.25	ug/ml	PMID[24828374]
NPT2	Others	Unspecified		MIC	=	28	ug/ml	PMID[24828374]
NPT2	Others	Unspecified		MIC	=	33	ug/ml	PMID[24828374]
NPT2	Others	Unspecified		IC50	>	100000	nM	PMID[24828374]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100	ug/ml	PMID[24828374]

☑ 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 NPC476917 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	491
0.1-0.2	2241
0.2-0.3	8921
0.3-0.4	15944
0.4-0.5	13189
0.5-0.6	1830
0.6-0.7	80
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC327527
0.9836	High Similarity	NPC476925
0.9672	High Similarity	NPC477040
0.9512	High Similarity	NPC477123
0.9512	High Similarity	NPC477966
0.9355	High Similarity	NPC477039
0.9339	High Similarity	NPC317217
0.9187	High Similarity	NPC477965
0.9187	High Similarity	NPC477038
0.9113	High Similarity	NPC179354
0.9106	High Similarity	NPC16922
0.9083	High Similarity	NPC212918
0.904	High Similarity	NPC74612
0.9024	High Similarity	NPC36255
0.896	High Similarity	NPC230979
0.8917	High Similarity	NPC150895
0.8889	High Similarity	NPC46536
0.8889	High Similarity	NPC23086
0.8889	High Similarity	NPC138139
0.888	High Similarity	NPC83115
0.8837	High Similarity	NPC89133
0.881	High Similarity	NPC303010
0.88	High Similarity	NPC272899
0.875	High Similarity	NPC207294
0.875	High Similarity	NPC112706
0.873	High Similarity	NPC130275
0.872	High Similarity	NPC477967
0.8699	High Similarity	NPC243704
0.8682	High Similarity	NPC120836
0.8682	High Similarity	NPC223063
0.8682	High Similarity	NPC198904
0.8672	High Similarity	NPC83178
0.8582	High Similarity	NPC307401
0.8571	High Similarity	NPC476947
0.8561	High Similarity	NPC471006
0.855	High Similarity	NPC61788
0.8529	High Similarity	NPC56197
0.8519	High Similarity	NPC476943
0.8456	Intermediate Similarity	NPC202260
0.8444	Intermediate Similarity	NPC310830
0.8444	Intermediate Similarity	NPC42400
0.8421	Intermediate Similarity	NPC218838
0.8409	Intermediate Similarity	NPC298190
0.8397	Intermediate Similarity	NPC59502
0.8394	Intermediate Similarity	NPC67003
0.837	Intermediate Similarity	NPC146872
0.837	Intermediate Similarity	NPC46896
0.8346	Intermediate Similarity	NPC471817
0.8346	Intermediate Similarity	NPC97566
0.8321	Intermediate Similarity	NPC26532
0.8296	Intermediate Similarity	NPC158525
0.8296	Intermediate Similarity	NPC92941
0.8286	Intermediate Similarity	NPC238843
0.8286	Intermediate Similarity	NPC142113
0.8286	Intermediate Similarity	NPC199044
0.8284	Intermediate Similarity	NPC470740
0.8273	Intermediate Similarity	NPC121158
0.8273	Intermediate Similarity	NPC263337
0.8258	Intermediate Similarity	NPC208389
0.8254	Intermediate Similarity	NPC87466
0.8248	Intermediate Similarity	NPC220094
0.8244	Intermediate Similarity	NPC290955
0.8244	Intermediate Similarity	NPC246392
0.8239	Intermediate Similarity	NPC71821
0.8239	Intermediate Similarity	NPC216755
0.8231	Intermediate Similarity	NPC473885
0.8231	Intermediate Similarity	NPC471074
0.8227	Intermediate Similarity	NPC185456
0.8214	Intermediate Similarity	NPC476946
0.8209	Intermediate Similarity	NPC471995
0.8201	Intermediate Similarity	NPC205765
0.8188	Intermediate Similarity	NPC90953
0.8182	Intermediate Similarity	NPC471007
0.8175	Intermediate Similarity	NPC144745
0.8175	Intermediate Similarity	NPC208906
0.8175	Intermediate Similarity	NPC310043
0.8175	Intermediate Similarity	NPC470742
0.8169	Intermediate Similarity	NPC470999
0.8169	Intermediate Similarity	NPC471292
0.8156	Intermediate Similarity	NPC476944
0.8154	Intermediate Similarity	NPC178382
0.8154	Intermediate Similarity	NPC243269
0.8143	Intermediate Similarity	NPC52412
0.813	Intermediate Similarity	NPC277525
0.8116	Intermediate Similarity	NPC236532
0.8112	Intermediate Similarity	NPC302987
0.8112	Intermediate Similarity	NPC471174
0.8102	Intermediate Similarity	NPC214572
0.8099	Intermediate Similarity	NPC5676
0.8085	Intermediate Similarity	NPC243577
0.8085	Intermediate Similarity	NPC267632
0.8074	Intermediate Similarity	NPC473982
0.8069	Intermediate Similarity	NPC212257
0.8047	Intermediate Similarity	NPC473969
0.8045	Intermediate Similarity	NPC329707
0.8045	Intermediate Similarity	NPC279877
0.8043	Intermediate Similarity	NPC4764
0.8042	Intermediate Similarity	NPC262198
0.8042	Intermediate Similarity	NPC233763
0.8028	Intermediate Similarity	NPC251865
0.8016	Intermediate Similarity	NPC28054
0.8014	Intermediate Similarity	NPC473152
0.8	Intermediate Similarity	NPC234494
0.8	Intermediate Similarity	NPC471001
0.8	Intermediate Similarity	NPC90296
0.8	Intermediate Similarity	NPC470998
0.7986	Intermediate Similarity	NPC470941
0.7986	Intermediate Similarity	NPC255414
0.7972	Intermediate Similarity	NPC290038
0.7972	Intermediate Similarity	NPC56731
0.7959	Intermediate Similarity	NPC472672
0.7959	Intermediate Similarity	NPC294511
0.7959	Intermediate Similarity	NPC121615
0.7956	Intermediate Similarity	NPC471998
0.7955	Intermediate Similarity	NPC300098
0.7955	Intermediate Similarity	NPC290193
0.7945	Intermediate Similarity	NPC228842
0.7945	Intermediate Similarity	NPC159927
0.7945	Intermediate Similarity	NPC46551
0.7945	Intermediate Similarity	NPC196864
0.7945	Intermediate Similarity	NPC476122
0.7945	Intermediate Similarity	NPC196846
0.7945	Intermediate Similarity	NPC469335
0.7945	Intermediate Similarity	NPC477404
0.7945	Intermediate Similarity	NPC470997
0.7943	Intermediate Similarity	NPC20500
0.7917	Intermediate Similarity	NPC346
0.7914	Intermediate Similarity	NPC215109
0.7914	Intermediate Similarity	NPC170604
0.7907	Intermediate Similarity	NPC137710
0.7905	Intermediate Similarity	NPC237259
0.7905	Intermediate Similarity	NPC302054
0.7905	Intermediate Similarity	NPC253201
0.7905	Intermediate Similarity	NPC98206
0.7905	Intermediate Similarity	NPC34421
0.7891	Intermediate Similarity	NPC217180
0.7891	Intermediate Similarity	NPC272590
0.7891	Intermediate Similarity	NPC471000
0.7891	Intermediate Similarity	NPC131801
0.7891	Intermediate Similarity	NPC312525
0.7886	Intermediate Similarity	NPC471521
0.7886	Intermediate Similarity	NPC473356
0.7883	Intermediate Similarity	NPC293253
0.7879	Intermediate Similarity	NPC118853
0.7879	Intermediate Similarity	NPC188377
0.7879	Intermediate Similarity	NPC65735
0.7877	Intermediate Similarity	NPC470791
0.7877	Intermediate Similarity	NPC69647
0.7877	Intermediate Similarity	NPC472654
0.7877	Intermediate Similarity	NPC125182
0.7877	Intermediate Similarity	NPC470790
0.7877	Intermediate Similarity	NPC95526
0.7872	Intermediate Similarity	NPC148374
0.7862	Intermediate Similarity	NPC10088
0.7862	Intermediate Similarity	NPC250228
0.7862	Intermediate Similarity	NPC221809
0.7857	Intermediate Similarity	NPC471996
0.7852	Intermediate Similarity	NPC25351
0.7847	Intermediate Similarity	NPC114513
0.7847	Intermediate Similarity	NPC245522
0.784	Intermediate Similarity	NPC105249
0.7838	Intermediate Similarity	NPC33938
0.7838	Intermediate Similarity	NPC246164
0.7838	Intermediate Similarity	NPC470996
0.7838	Intermediate Similarity	NPC476201
0.7838	Intermediate Similarity	NPC469503
0.7836	Intermediate Similarity	NPC95567
0.7836	Intermediate Similarity	NPC476016
0.7836	Intermediate Similarity	NPC319140
0.7832	Intermediate Similarity	NPC223415
0.7832	Intermediate Similarity	NPC470741
0.7823	Intermediate Similarity	NPC472298
0.7823	Intermediate Similarity	NPC156189
0.782	Intermediate Similarity	NPC71274
0.782	Intermediate Similarity	NPC75557
0.7812	Intermediate Similarity	NPC45536
0.7808	Intermediate Similarity	NPC476942
0.7808	Intermediate Similarity	NPC93666
0.7808	Intermediate Similarity	NPC476941
0.7801	Intermediate Similarity	NPC474722
0.78	Intermediate Similarity	NPC41880
0.78	Intermediate Similarity	NPC107646
0.7793	Intermediate Similarity	NPC478166
0.7793	Intermediate Similarity	NPC276676
0.7785	Intermediate Similarity	NPC282445
0.7785	Intermediate Similarity	NPC30222
0.7785	Intermediate Similarity	NPC178932
0.7785	Intermediate Similarity	NPC471863
0.7778	Intermediate Similarity	NPC474279
0.7778	Intermediate Similarity	NPC474438
0.777	Intermediate Similarity	NPC18135
0.7762	Intermediate Similarity	NPC62103
0.7762	Intermediate Similarity	NPC20578
0.7761	Intermediate Similarity	NPC474260
0.7761	Intermediate Similarity	NPC81912
0.7761	Intermediate Similarity	NPC329694
0.7761	Intermediate Similarity	NPC329922
0.7755	Intermediate Similarity	NPC195325
0.7748	Intermediate Similarity	NPC195954
0.7748	Intermediate Similarity	NPC194499

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 NPC476917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	643
0.2-0.3	870
0.3-0.4	2759
0.4-0.5	3250
0.5-0.6	1235
0.6-0.7	123
0.7-0.8	0
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
0.7852	Intermediate Similarity	NPD5761	Phase 2
0.7852	Intermediate Similarity	NPD5760	Phase 2
0.7431	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6273	Approved
0.7338	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD8032	Phase 2
0.7279	Intermediate Similarity	NPD3972	Approved
0.7192	Intermediate Similarity	NPD1471	Phase 3
0.7185	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1876	Approved
0.7101	Intermediate Similarity	NPD5327	Phase 3
0.7092	Intermediate Similarity	NPD6832	Phase 2
0.708	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7003	Approved
0.7047	Intermediate Similarity	NPD4628	Phase 3
0.7045	Intermediate Similarity	NPD1241	Discontinued
0.6985	Remote Similarity	NPD3025	Approved
0.6985	Remote Similarity	NPD3024	Approved
0.695	Remote Similarity	NPD2798	Approved
0.6939	Remote Similarity	NPD2799	Discontinued
0.6928	Remote Similarity	NPD6765	Approved
0.6928	Remote Similarity	NPD6764	Approved
0.6923	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7458	Discontinued
0.6903	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4307	Phase 2
0.6884	Remote Similarity	NPD3023	Approved
0.6884	Remote Similarity	NPD3026	Approved
0.6867	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5585	Approved
0.6846	Remote Similarity	NPD2344	Approved
0.6846	Remote Similarity	NPD2346	Discontinued
0.6824	Remote Similarity	NPD8434	Phase 2
0.6781	Remote Similarity	NPD2979	Phase 3
0.6781	Remote Similarity	NPD4140	Approved
0.6779	Remote Similarity	NPD2531	Phase 2
0.6779	Remote Similarity	NPD2796	Approved
0.6763	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2797	Approved
0.6761	Remote Similarity	NPD3267	Approved
0.6761	Remote Similarity	NPD3266	Approved
0.6759	Remote Similarity	NPD2313	Discontinued
0.6739	Remote Similarity	NPD1651	Approved
0.6735	Remote Similarity	NPD6355	Discontinued
0.6714	Remote Similarity	NPD1281	Approved
0.6711	Remote Similarity	NPD3748	Approved
0.6711	Remote Similarity	NPD4308	Phase 3
0.6711	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD17	Approved
0.6687	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD3873	Phase 3
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD6784	Approved
0.6667	Remote Similarity	NPD3869	Phase 3
0.6645	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3268	Approved
0.6644	Remote Similarity	NPD3764	Approved
0.6625	Remote Similarity	NPD7819	Suspended
0.6623	Remote Similarity	NPD7440	Discontinued
0.6623	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5735	Approved
0.6622	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4359	Approved
0.6601	Remote Similarity	NPD8166	Discontinued
0.6601	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4110	Phase 3
0.6593	Remote Similarity	NPD5535	Approved
0.6584	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3226	Approved
0.6577	Remote Similarity	NPD6353	Approved
0.6575	Remote Similarity	NPD7095	Approved
0.6573	Remote Similarity	NPD1283	Approved
0.6569	Remote Similarity	NPD7157	Approved
0.6562	Remote Similarity	NPD6279	Approved
0.6562	Remote Similarity	NPD6280	Approved
0.6556	Remote Similarity	NPD6100	Approved
0.6556	Remote Similarity	NPD1551	Phase 2
0.6556	Remote Similarity	NPD2438	Suspended
0.6556	Remote Similarity	NPD6099	Approved
0.6554	Remote Similarity	NPD3142	Approved
0.6554	Remote Similarity	NPD3140	Approved
0.6549	Remote Similarity	NPD1608	Approved
0.6543	Remote Similarity	NPD7768	Phase 2
0.6541	Remote Similarity	NPD6599	Discontinued
0.6541	Remote Similarity	NPD2182	Approved
0.6538	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6798	Discontinued
0.6528	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5494	Approved
0.6519	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3657	Discovery
0.651	Remote Similarity	NPD4622	Approved
0.651	Remote Similarity	NPD1933	Approved
0.651	Remote Similarity	NPD4618	Approved
0.65	Remote Similarity	NPD5691	Approved
0.6496	Remote Similarity	NPD5951	Approved
0.6494	Remote Similarity	NPD3750	Approved
0.6488	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4062	Phase 3
0.6486	Remote Similarity	NPD6663	Approved
0.6483	Remote Similarity	NPD1019	Discontinued
0.6463	Remote Similarity	NPD7008	Discontinued
0.646	Remote Similarity	NPD7577	Discontinued
0.6456	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD3019	Approved
0.6452	Remote Similarity	NPD3887	Approved
0.6447	Remote Similarity	NPD4476	Approved
0.6447	Remote Similarity	NPD4477	Approved
0.6447	Remote Similarity	NPD2935	Discontinued
0.6438	Remote Similarity	NPD5736	Approved
0.6438	Remote Similarity	NPD7028	Phase 2
0.6434	Remote Similarity	NPD9717	Approved
0.6433	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6559	Discontinued
0.6429	Remote Similarity	NPD1243	Approved
0.6424	Remote Similarity	NPD5688	Approved
0.6424	Remote Similarity	NPD5689	Approved
0.642	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD1203	Approved
0.641	Remote Similarity	NPD7236	Approved
0.6402	Remote Similarity	NPD3749	Approved
0.6398	Remote Similarity	NPD6873	Phase 2
0.6398	Remote Similarity	NPD6677	Suspended
0.6398	Remote Similarity	NPD7411	Suspended
0.6391	Remote Similarity	NPD3134	Approved
0.6376	Remote Similarity	NPD6233	Phase 2
0.6376	Remote Similarity	NPD4870	Approved
0.637	Remote Similarity	NPD4624	Approved
0.6364	Remote Similarity	NPD1549	Phase 2
0.6364	Remote Similarity	NPD919	Approved
0.6364	Remote Similarity	NPD6287	Discontinued
0.6364	Remote Similarity	NPD2897	Discontinued
0.6352	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7229	Phase 3
0.6347	Remote Similarity	NPD6808	Phase 2
0.6341	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD2932	Approved
0.6338	Remote Similarity	NPD1778	Approved
0.6338	Remote Similarity	NPD3095	Discontinued
0.6331	Remote Similarity	NPD6387	Discontinued
0.6329	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7097	Phase 1
0.6312	Remote Similarity	NPD1894	Discontinued
0.6309	Remote Similarity	NPD7294	Phase 1
0.6309	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD1238	Approved
0.6303	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7075	Discontinued
0.6299	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2353	Approved
0.6299	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6005	Phase 3
0.6299	Remote Similarity	NPD5763	Approved
0.6299	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6004	Phase 3
0.6299	Remote Similarity	NPD6002	Phase 3
0.6299	Remote Similarity	NPD5762	Approved
0.6299	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3496	Discontinued
0.6294	Remote Similarity	NPD7177	Discontinued
0.6287	Remote Similarity	NPD1247	Approved
0.6284	Remote Similarity	NPD2614	Approved
0.6275	Remote Similarity	NPD1510	Phase 2
0.6273	Remote Similarity	NPD2649	Approved
0.6273	Remote Similarity	NPD2651	Approved
0.6267	Remote Similarity	NPD7713	Phase 3
0.6266	Remote Similarity	NPD6799	Approved
0.6266	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6844	Discontinued
0.6258	Remote Similarity	NPD4534	Discontinued
0.6257	Remote Similarity	NPD5844	Phase 1
0.6257	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7427	Discontinued
0.625	Remote Similarity	NPD1611	Approved
0.6242	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD5536	Phase 2
0.6241	Remote Similarity	NPD164	Approved
0.6233	Remote Similarity	NPD8651	Approved
0.6232	Remote Similarity	NPD6858	Approved
0.6232	Remote Similarity	NPD7094	Approved
0.6232	Remote Similarity	NPD7843	Approved
0.6226	Remote Similarity	NPD4662	Approved
0.6226	Remote Similarity	NPD4661	Approved
0.6225	Remote Similarity	NPD4060	Phase 1
0.6224	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4626	Approved
0.6222	Remote Similarity	NPD1358	Approved
0.622	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD2800	Approved
0.6216	Remote Similarity	NPD9494	Approved
0.6215	Remote Similarity	NPD7693	Approved
0.6213	Remote Similarity	NPD3926	Phase 2
0.6211	Remote Similarity	NPD7239	Suspended

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