NPASS Compound

Structure

NPC58219 OpenBabel07101718192D 28 30 0 0 1 0 0 0 0 0999 V2000 -1.3189 1.7065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8448 3.4089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1265 -0.0253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5324 4.1123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1207 -0.9927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3269 2.4389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1080 2.0589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8836 2.5925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9915 0.5336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3349 1.5279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4518 2.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7752 0.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4788 3.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2185 1.0646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5567 0.1536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9189 2.1500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1926 1.6415 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0933 1.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2318 4.4470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0305 -0.7270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0923 1.4377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 2.8079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7332 1.8444 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 12 2 0 0 0 0 3 14 2 0 0 0 0 4 15 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 10 22 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 13 2 1 6 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 11 1 6 0 0 0 16 20 1 0 0 0 0 17 9 1 1 0 0 0 17 28 1 0 0 0 0 18 22 1 1 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 27 1 6 0 0 0 21 25 2 0 0 0 0 21 27 1 0 0 0 0 22 5 1 6 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	405.594
LogP:	2.713
LogD:	2.935
LogS:	-3.957
# Rotatable Bonds:	2
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	5.974
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.828
MDCK Permeability:	6.995028525125235e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.146

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	54.46385192871094%
Volume Distribution (VD):	1.028
Pgp-substrate:	47.236839294433594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.202
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.379
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.186
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.587
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	7.117
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.269
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.687
AMES Toxicity:	0.346
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.542
Carcinogencity:	0.75
Eye Corrosion:	0.08
Eye Irritation:	0.029
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC58219

Natural Product ID:	NPC58219
*Common Name:**	Uprolide E Acetate
IUPAC Name:	n.a.
Synonyms:	Uprolide E Acetate
Standard InCHIKey:	WUFJYPLWWXQZJB-GCGYEZPTSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-12-7-6-8-13(2)19(26-15(4)23)20-16(14(3)21(25)27-20)11-18(24)22(5)10-9-17(12)28-22/h13,16-20,24H,1,3,6-11H2,2,4-5H3/t13-,16-,17-,18+,19+,20+,22-/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@@H](C)CCCC(=C)[C@H]2O[C@@]([C@@H](C[C@@H]3[C@H]1OC(=O)C3=C)O)(C)CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517478
PubChem CID:	10318356
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO8989	Eunicea mammosa	Species	Plexauridae	Eukaryota	n.a.	Caribbean	n.a.	PMID[7595589]
NPO8989	Eunicea mammosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[486600]

☑ 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 NPC58219 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	232
0.1-0.2	1553
0.2-0.3	5728
0.3-0.4	12772
0.4-0.5	10874
0.5-0.6	7487
0.6-0.7	3062
0.7-0.8	796
0.8-0.85	143
0.85-0.9	36
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC177629
0.988	High Similarity	NPC92974
0.9878	High Similarity	NPC186148
0.9419	High Similarity	NPC208886
0.9419	High Similarity	NPC12172
0.931	High Similarity	NPC81419
0.931	High Similarity	NPC179746
0.9286	High Similarity	NPC475019
0.9286	High Similarity	NPC474949
0.9277	High Similarity	NPC474780
0.9195	High Similarity	NPC30515
0.9195	High Similarity	NPC184463
0.9186	High Similarity	NPC307411
0.9167	High Similarity	NPC304509
0.9167	High Similarity	NPC47958
0.9167	High Similarity	NPC329749
0.9167	High Similarity	NPC149725
0.908	High Similarity	NPC474323
0.908	High Similarity	NPC206614
0.908	High Similarity	NPC51004
0.907	High Similarity	NPC202672
0.9059	High Similarity	NPC476015
0.9059	High Similarity	NPC474762
0.9048	High Similarity	NPC3464
0.9048	High Similarity	NPC475963
0.9048	High Similarity	NPC151176
0.8953	High Similarity	NPC190753
0.8889	High Similarity	NPC36954
0.8876	High Similarity	NPC476300
0.8876	High Similarity	NPC212486
0.8876	High Similarity	NPC475912
0.8864	High Similarity	NPC474761
0.8864	High Similarity	NPC476004
0.8791	High Similarity	NPC470883
0.8791	High Similarity	NPC39859
0.8791	High Similarity	NPC158416
0.8791	High Similarity	NPC76862
0.8778	High Similarity	NPC474035
0.8778	High Similarity	NPC190294
0.8778	High Similarity	NPC81386
0.8764	High Similarity	NPC70251
0.8764	High Similarity	NPC475881
0.875	High Similarity	NPC173926
0.875	High Similarity	NPC474951
0.8696	High Similarity	NPC328562
0.8696	High Similarity	NPC323421
0.8696	High Similarity	NPC471150
0.8681	High Similarity	NPC270013
0.8681	High Similarity	NPC14961
0.8681	High Similarity	NPC475900
0.8621	High Similarity	NPC470242
0.8621	High Similarity	NPC162071
0.8587	High Similarity	NPC476009
0.8587	High Similarity	NPC31645
0.8587	High Similarity	NPC476315
0.8571	High Similarity	NPC474981
0.8556	High Similarity	NPC329952
0.8523	High Similarity	NPC5130
0.8523	High Similarity	NPC248602
0.8523	High Similarity	NPC118601
0.8488	Intermediate Similarity	NPC11620
0.8488	Intermediate Similarity	NPC257358
0.8488	Intermediate Similarity	NPC474472
0.8427	Intermediate Similarity	NPC178875
0.8404	Intermediate Similarity	NPC187268
0.8404	Intermediate Similarity	NPC473326
0.8404	Intermediate Similarity	NPC474213
0.8333	Intermediate Similarity	NPC295312
0.8333	Intermediate Similarity	NPC324017
0.8333	Intermediate Similarity	NPC474032
0.8333	Intermediate Similarity	NPC320019
0.8316	Intermediate Similarity	NPC471381
0.8316	Intermediate Similarity	NPC186861
0.8315	Intermediate Similarity	NPC231889
0.8298	Intermediate Similarity	NPC474313
0.8295	Intermediate Similarity	NPC137033
0.8295	Intermediate Similarity	NPC21469
0.828	Intermediate Similarity	NPC472873
0.8242	Intermediate Similarity	NPC473619
0.8242	Intermediate Similarity	NPC475748
0.8229	Intermediate Similarity	NPC476270
0.8229	Intermediate Similarity	NPC15993
0.8222	Intermediate Similarity	NPC227379
0.8222	Intermediate Similarity	NPC217983
0.8222	Intermediate Similarity	NPC207114
0.8222	Intermediate Similarity	NPC153805
0.8222	Intermediate Similarity	NPC281516
0.8222	Intermediate Similarity	NPC474471
0.8202	Intermediate Similarity	NPC112685
0.8191	Intermediate Similarity	NPC473859
0.8182	Intermediate Similarity	NPC9868
0.8172	Intermediate Similarity	NPC57405
0.8172	Intermediate Similarity	NPC303942
0.8172	Intermediate Similarity	NPC71589
0.8163	Intermediate Similarity	NPC100487
0.8152	Intermediate Similarity	NPC184063
0.8152	Intermediate Similarity	NPC473321
0.8152	Intermediate Similarity	NPC469627
0.8144	Intermediate Similarity	NPC86077
0.8144	Intermediate Similarity	NPC474747
0.8132	Intermediate Similarity	NPC215556
0.8132	Intermediate Similarity	NPC151770
0.8132	Intermediate Similarity	NPC477011
0.8132	Intermediate Similarity	NPC473564
0.8125	Intermediate Similarity	NPC288876
0.8125	Intermediate Similarity	NPC70865
0.8105	Intermediate Similarity	NPC181151
0.8085	Intermediate Similarity	NPC475659
0.8085	Intermediate Similarity	NPC163228
0.8085	Intermediate Similarity	NPC476053
0.8081	Intermediate Similarity	NPC243998
0.8081	Intermediate Similarity	NPC54737
0.8068	Intermediate Similarity	NPC272814
0.8065	Intermediate Similarity	NPC153590
0.8065	Intermediate Similarity	NPC162205
0.8065	Intermediate Similarity	NPC273579
0.8065	Intermediate Similarity	NPC288240
0.8065	Intermediate Similarity	NPC135776
0.8065	Intermediate Similarity	NPC295204
0.8061	Intermediate Similarity	NPC475945
0.8061	Intermediate Similarity	NPC475871
0.8043	Intermediate Similarity	NPC297474
0.8043	Intermediate Similarity	NPC54065
0.8043	Intermediate Similarity	NPC19087
0.8043	Intermediate Similarity	NPC216284
0.8041	Intermediate Similarity	NPC47880
0.8041	Intermediate Similarity	NPC133907
0.8041	Intermediate Similarity	NPC185141
0.8041	Intermediate Similarity	NPC128733
0.8041	Intermediate Similarity	NPC201718
0.8041	Intermediate Similarity	NPC46998
0.8041	Intermediate Similarity	NPC110443
0.8023	Intermediate Similarity	NPC19841
0.8022	Intermediate Similarity	NPC234077
0.8022	Intermediate Similarity	NPC151403
0.8022	Intermediate Similarity	NPC39754
0.8022	Intermediate Similarity	NPC171135
0.8022	Intermediate Similarity	NPC169511
0.8022	Intermediate Similarity	NPC133730
0.8022	Intermediate Similarity	NPC172821
0.8022	Intermediate Similarity	NPC79549
0.8022	Intermediate Similarity	NPC287164
0.8022	Intermediate Similarity	NPC61257
0.8022	Intermediate Similarity	NPC473715
0.8022	Intermediate Similarity	NPC81045
0.8022	Intermediate Similarity	NPC100454
0.8022	Intermediate Similarity	NPC476708
0.8022	Intermediate Similarity	NPC191929
0.8022	Intermediate Similarity	NPC274446
0.8022	Intermediate Similarity	NPC242364
0.8022	Intermediate Similarity	NPC261952
0.8022	Intermediate Similarity	NPC320569
0.8021	Intermediate Similarity	NPC471144
0.8	Intermediate Similarity	NPC171174
0.8	Intermediate Similarity	NPC284902
0.8	Intermediate Similarity	NPC309757
0.8	Intermediate Similarity	NPC142117
0.8	Intermediate Similarity	NPC91771
0.8	Intermediate Similarity	NPC232555
0.8	Intermediate Similarity	NPC114694
0.8	Intermediate Similarity	NPC164393
0.8	Intermediate Similarity	NPC142529
0.8	Intermediate Similarity	NPC62118
0.8	Intermediate Similarity	NPC240695
0.8	Intermediate Similarity	NPC236692
0.8	Intermediate Similarity	NPC279621
0.8	Intermediate Similarity	NPC107717
0.8	Intermediate Similarity	NPC475581
0.8	Intermediate Similarity	NPC187661
0.8	Intermediate Similarity	NPC231096
0.798	Intermediate Similarity	NPC203659
0.7979	Intermediate Similarity	NPC474338
0.7979	Intermediate Similarity	NPC473316
0.7979	Intermediate Similarity	NPC473330
0.7978	Intermediate Similarity	NPC224386
0.7978	Intermediate Similarity	NPC194859
0.7978	Intermediate Similarity	NPC470238
0.7978	Intermediate Similarity	NPC138647
0.7976	Intermediate Similarity	NPC217725
0.7959	Intermediate Similarity	NPC225353
0.7959	Intermediate Similarity	NPC149371
0.7959	Intermediate Similarity	NPC80144
0.7957	Intermediate Similarity	NPC470379
0.7957	Intermediate Similarity	NPC133888
0.7957	Intermediate Similarity	NPC470373
0.7957	Intermediate Similarity	NPC35959
0.7957	Intermediate Similarity	NPC171360
0.7957	Intermediate Similarity	NPC293001
0.7957	Intermediate Similarity	NPC131209
0.7957	Intermediate Similarity	NPC57304
0.7957	Intermediate Similarity	NPC29821
0.7957	Intermediate Similarity	NPC63193
0.7957	Intermediate Similarity	NPC133698
0.7955	Intermediate Similarity	NPC246076
0.7935	Intermediate Similarity	NPC155935
0.7935	Intermediate Similarity	NPC81778
0.7935	Intermediate Similarity	NPC42598
0.7935	Intermediate Similarity	NPC93794
0.7935	Intermediate Similarity	NPC38392
0.7935	Intermediate Similarity	NPC91067

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 NPC58219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	2376
0.2-0.3	3713
0.3-0.4	1892
0.4-0.5	575
0.5-0.6	266
0.6-0.7	49
0.7-0.8	5
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
0.7692	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6698	Approved
0.766	Intermediate Similarity	NPD46	Approved
0.7647	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7983	Approved
0.7347	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7838	Discovery
0.7264	Intermediate Similarity	NPD6371	Approved
0.7188	Intermediate Similarity	NPD1695	Approved
0.7037	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6686	Approved
0.6818	Remote Similarity	NPD6053	Discontinued
0.6759	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5344	Discontinued
0.6638	Remote Similarity	NPD8516	Approved
0.6638	Remote Similarity	NPD8515	Approved
0.6638	Remote Similarity	NPD8517	Approved
0.6638	Remote Similarity	NPD8513	Phase 3
0.6635	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD5778	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.6633	Remote Similarity	NPD4250	Approved
0.6633	Remote Similarity	NPD4251	Approved
0.6632	Remote Similarity	NPD6435	Approved
0.66	Remote Similarity	NPD5785	Approved
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5282	Discontinued
0.6562	Remote Similarity	NPD5362	Discontinued
0.6562	Remote Similarity	NPD7154	Phase 3
0.6531	Remote Similarity	NPD4249	Approved
0.6531	Remote Similarity	NPD5786	Approved
0.6526	Remote Similarity	NPD5369	Approved
0.6496	Remote Similarity	NPD8268	Approved
0.6496	Remote Similarity	NPD8267	Approved
0.6496	Remote Similarity	NPD8266	Approved
0.6496	Remote Similarity	NPD8269	Approved
0.646	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD5363	Approved
0.6421	Remote Similarity	NPD5368	Approved
0.6417	Remote Similarity	NPD7507	Approved
0.6396	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7909	Approved
0.6364	Remote Similarity	NPD8074	Phase 3
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7638	Approved
0.6316	Remote Similarity	NPD4632	Approved
0.6293	Remote Similarity	NPD7115	Discovery
0.6289	Remote Similarity	NPD4269	Approved
0.6289	Remote Similarity	NPD4270	Approved
0.6286	Remote Similarity	NPD7839	Suspended
0.6273	Remote Similarity	NPD6008	Approved
0.6262	Remote Similarity	NPD7639	Approved
0.6262	Remote Similarity	NPD6648	Approved
0.6262	Remote Similarity	NPD7640	Approved
0.626	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4819	Approved
0.6239	Remote Similarity	NPD7641	Discontinued
0.6214	Remote Similarity	NPD6411	Approved
0.6198	Remote Similarity	NPD7492	Approved
0.6195	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6399	Phase 3
0.6148	Remote Similarity	NPD6616	Approved
0.6148	Remote Similarity	NPD8451	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6134	Remote Similarity	NPD6319	Approved
0.6122	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7830	Approved
0.6116	Remote Similarity	NPD7829	Approved
0.6111	Remote Similarity	NPD6845	Suspended
0.61	Remote Similarity	NPD1694	Approved
0.6098	Remote Similarity	NPD8448	Approved
0.6098	Remote Similarity	NPD7078	Approved
0.6087	Remote Similarity	NPD8297	Approved
0.6083	Remote Similarity	NPD6921	Approved
0.6082	Remote Similarity	NPD4252	Approved
0.6071	Remote Similarity	NPD6412	Phase 2
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6061	Remote Similarity	NPD6110	Phase 1
0.6058	Remote Similarity	NPD8034	Phase 2
0.6058	Remote Similarity	NPD8035	Phase 2
0.6048	Remote Similarity	NPD7736	Approved
0.6042	Remote Similarity	NPD4271	Approved
0.6042	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4268	Approved
0.6036	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6370	Approved
0.6032	Remote Similarity	NPD7260	Phase 2
0.602	Remote Similarity	NPD4790	Discontinued
0.6018	Remote Similarity	NPD7320	Approved
0.6018	Remote Similarity	NPD6881	Approved
0.6018	Remote Similarity	NPD6899	Approved
0.6017	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6649	Approved
0.5984	Remote Similarity	NPD7604	Phase 2
0.5982	Remote Similarity	NPD6675	Approved
0.5982	Remote Similarity	NPD5739	Approved
0.5982	Remote Similarity	NPD7128	Approved
0.5982	Remote Similarity	NPD6402	Approved
0.5968	Remote Similarity	NPD8293	Discontinued
0.5965	Remote Similarity	NPD6373	Approved
0.5965	Remote Similarity	NPD6372	Approved
0.596	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7341	Phase 2
0.5952	Remote Similarity	NPD8390	Approved
0.5952	Remote Similarity	NPD8392	Approved
0.5952	Remote Similarity	NPD8391	Approved
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD8444	Approved
0.595	Remote Similarity	NPD5983	Phase 2
0.595	Remote Similarity	NPD6015	Approved
0.5935	Remote Similarity	NPD8342	Approved
0.5935	Remote Similarity	NPD8340	Approved
0.5935	Remote Similarity	NPD8341	Approved
0.5935	Remote Similarity	NPD8299	Approved
0.5929	Remote Similarity	NPD5697	Approved
0.5929	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6883	Approved
0.5913	Remote Similarity	NPD7102	Approved
0.5913	Remote Similarity	NPD7290	Approved
0.5904	Remote Similarity	NPD3730	Approved
0.5904	Remote Similarity	NPD3728	Approved
0.5902	Remote Similarity	NPD5988	Approved
0.5902	Remote Similarity	NPD8080	Discontinued
0.5889	Remote Similarity	NPD7331	Phase 2
0.5887	Remote Similarity	NPD6336	Discontinued
0.5887	Remote Similarity	NPD8273	Phase 1
0.5882	Remote Similarity	NPD6422	Discontinued
0.5882	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6011	Approved
0.5862	Remote Similarity	NPD6847	Approved
0.5862	Remote Similarity	NPD8130	Phase 1
0.5862	Remote Similarity	NPD2204	Approved
0.5862	Remote Similarity	NPD6617	Approved
0.5862	Remote Similarity	NPD6869	Approved
0.5856	Remote Similarity	NPD7632	Discontinued
0.5854	Remote Similarity	NPD8328	Phase 3
0.5843	Remote Similarity	NPD3197	Phase 1
0.5833	Remote Similarity	NPD7327	Approved
0.5833	Remote Similarity	NPD7328	Approved
0.5826	Remote Similarity	NPD6014	Approved
0.5826	Remote Similarity	NPD6012	Approved
0.5826	Remote Similarity	NPD6013	Approved
0.5826	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7524	Approved
0.5824	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.582	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.582	Remote Similarity	NPD8033	Approved
0.5812	Remote Similarity	NPD6882	Approved
0.5789	Remote Similarity	NPD5701	Approved
0.5785	Remote Similarity	NPD7516	Approved
0.5784	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6083	Phase 2
0.578	Remote Similarity	NPD6084	Phase 2
0.578	Remote Similarity	NPD7902	Approved
0.5778	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD1700	Approved
0.5755	Remote Similarity	NPD7637	Suspended
0.5747	Remote Similarity	NPD3198	Approved
0.5743	Remote Similarity	NPD4788	Approved
0.5738	Remote Similarity	NPD8294	Approved
0.5738	Remote Similarity	NPD8377	Approved
0.5729	Remote Similarity	NPD8039	Approved
0.5726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4802	Phase 2
0.5714	Remote Similarity	NPD8139	Approved
0.5714	Remote Similarity	NPD8086	Approved
0.5714	Remote Similarity	NPD8082	Approved
0.5714	Remote Similarity	NPD8085	Approved
0.5714	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8138	Approved
0.5714	Remote Similarity	NPD8084	Approved
0.5714	Remote Similarity	NPD8083	Approved
0.5714	Remote Similarity	NPD5370	Suspended
0.5714	Remote Similarity	NPD4238	Approved
0.5691	Remote Similarity	NPD8296	Approved
0.5691	Remote Similarity	NPD8380	Approved
0.5691	Remote Similarity	NPD8378	Approved
0.5691	Remote Similarity	NPD7503	Approved
0.5691	Remote Similarity	NPD8335	Approved
0.5691	Remote Similarity	NPD8379	Approved
0.5691	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD6033	Approved
0.5664	Remote Similarity	NPD8276	Approved
0.5664	Remote Similarity	NPD8275	Approved
0.5648	Remote Similarity	NPD7748	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