NPASS Compound

Structure

NPC225283 OpenBabel07101718332D 21 23 0 0 1 0 0 0 0 0999 V2000 -0.1428 2.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2539 -1.5576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2826 -0.6029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6040 0.2802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4507 1.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 1.7660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8350 0.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 1.4397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4936 -0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1107 -0.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -0.7660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4410 1.1139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2597 2.0825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0504 -0.8382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0406 1.9992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2816 -1.0554 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 8 1 0 0 0 0 3 4 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 15 1 1 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 1 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 2 1 1 0 0 0 14 21 1 0 0 0 0 15 19 1 1 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.13
Volume:	287.159
LogP:	1.005
LogD:	0.682
LogS:	-2.193
# Rotatable Bonds:	1
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	5.861
Fsp3:	0.667
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:	-5.213
MDCK Permeability:	1.2439552847354207e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.697
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.675
Plasma Protein Binding (PPB):	74.0807876586914%
Volume Distribution (VD):	1.544
Pgp-substrate:	25.276582717895508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.771
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.532
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.157
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.212
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	11.082
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.784
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.789
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.416
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC225283

Natural Product ID:	NPC225283
*Common Name:**	HGVUPZFNJFDVQM-HEQUYQGPSA-N
IUPAC Name:	n.a.
Synonyms:	8Alpha-Hydroxyhirsutinolide
Standard InCHIKey:	HGVUPZFNJFDVQM-HEQUYQGPSA-N
Standard InCHI:	InChI=1S/C15H20O6/c1-8-5-10(17)12-9(7-16)13(18)20-11(12)6-14(2)3-4-15(8,19)21-14/h6,8,10,16-17,19H,3-5,7H2,1-2H3/b11-6+/t8-,10+,14-,15+/m1/s1
SMILES:	OCC1=C2[C@@H](O)C[C@@H](C)[C@]3(O[C@](/C=C2/OC1=O)(C)CC3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2062863
PubChem CID:	70690654
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO33276	vernonia cinerea	Species	Asteraceae	Eukaryota	flower	n.a.	n.a.	PMID[22850207]

☑ 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	2
Others	4

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	82.6	%	PMID[546439]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	121.1	%	PMID[546439]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	24700.0	nM	PMID[546439]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	100.0	%	PMID[546439]
NPT2	Others	Unspecified		Inhibition	=	65.6	%	PMID[546439]
NPT2	Others	Unspecified		IC50	=	1900.0	nM	PMID[546439]

☑ 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 NPC225283 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	185
0.1-0.2	1208
0.2-0.3	4603
0.3-0.4	11644
0.4-0.5	15720
0.5-0.6	6550
0.6-0.7	2500
0.7-0.8	259
0.8-0.85	10
0.85-0.9	5
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC3436
0.9765	High Similarity	NPC470520
0.9651	High Similarity	NPC59646
0.954	High Similarity	NPC470521
0.931	High Similarity	NPC32494
0.931	High Similarity	NPC175842
0.9111	High Similarity	NPC473333
0.9011	High Similarity	NPC2666
0.8864	High Similarity	NPC242877
0.8864	High Similarity	NPC64913
0.8791	High Similarity	NPC471492
0.8602	High Similarity	NPC471490
0.8539	High Similarity	NPC260343
0.8061	Intermediate Similarity	NPC197835
0.8061	Intermediate Similarity	NPC189609
0.8061	Intermediate Similarity	NPC140591
0.8061	Intermediate Similarity	NPC291500
0.8061	Intermediate Similarity	NPC303653
0.8021	Intermediate Similarity	NPC471462
0.8	Intermediate Similarity	NPC471185
0.7907	Intermediate Similarity	NPC315394
0.7895	Intermediate Similarity	NPC474338
0.7857	Intermediate Similarity	NPC469864
0.7857	Intermediate Similarity	NPC469872
0.7767	Intermediate Similarity	NPC38154
0.7755	Intermediate Similarity	NPC187268
0.7684	Intermediate Similarity	NPC2882
0.7609	Intermediate Similarity	NPC130030
0.7604	Intermediate Similarity	NPC472954
0.7604	Intermediate Similarity	NPC471483
0.7558	Intermediate Similarity	NPC470686
0.7556	Intermediate Similarity	NPC112868
0.7551	Intermediate Similarity	NPC301596
0.7551	Intermediate Similarity	NPC299396
0.7527	Intermediate Similarity	NPC475461
0.7527	Intermediate Similarity	NPC305475
0.7526	Intermediate Similarity	NPC469632
0.75	Intermediate Similarity	NPC114979
0.75	Intermediate Similarity	NPC111114
0.75	Intermediate Similarity	NPC191476
0.75	Intermediate Similarity	NPC300312
0.75	Intermediate Similarity	NPC261607
0.75	Intermediate Similarity	NPC475706
0.75	Intermediate Similarity	NPC158061
0.7476	Intermediate Similarity	NPC81630
0.7447	Intermediate Similarity	NPC191283
0.7423	Intermediate Similarity	NPC32862
0.7423	Intermediate Similarity	NPC272293
0.7423	Intermediate Similarity	NPC189651
0.7423	Intermediate Similarity	NPC40821
0.7423	Intermediate Similarity	NPC475098
0.7423	Intermediate Similarity	NPC156553
0.7419	Intermediate Similarity	NPC470755
0.7419	Intermediate Similarity	NPC165162
0.7419	Intermediate Similarity	NPC255307
0.7396	Intermediate Similarity	NPC129419
0.7391	Intermediate Similarity	NPC474809
0.7374	Intermediate Similarity	NPC172998
0.7374	Intermediate Similarity	NPC230800
0.7368	Intermediate Similarity	NPC475819
0.7368	Intermediate Similarity	NPC472378
0.7368	Intermediate Similarity	NPC476805
0.7363	Intermediate Similarity	NPC59994
0.7363	Intermediate Similarity	NPC474894
0.7363	Intermediate Similarity	NPC78677
0.7347	Intermediate Similarity	NPC167219
0.7347	Intermediate Similarity	NPC96541
0.734	Intermediate Similarity	NPC261721
0.734	Intermediate Similarity	NPC311163
0.7312	Intermediate Similarity	NPC96259
0.7312	Intermediate Similarity	NPC141193
0.7312	Intermediate Similarity	NPC158756
0.7294	Intermediate Similarity	NPC475004
0.7294	Intermediate Similarity	NPC232812
0.7292	Intermediate Similarity	NPC212664
0.7292	Intermediate Similarity	NPC51358
0.7292	Intermediate Similarity	NPC295312
0.7292	Intermediate Similarity	NPC268298
0.7292	Intermediate Similarity	NPC212598
0.7292	Intermediate Similarity	NPC307092
0.7283	Intermediate Similarity	NPC89555
0.7283	Intermediate Similarity	NPC229825
0.7273	Intermediate Similarity	NPC234339
0.7273	Intermediate Similarity	NPC273197
0.7273	Intermediate Similarity	NPC469873
0.7273	Intermediate Similarity	NPC220221
0.7273	Intermediate Similarity	NPC304886
0.7263	Intermediate Similarity	NPC72513
0.7263	Intermediate Similarity	NPC160138
0.7255	Intermediate Similarity	NPC469657
0.7255	Intermediate Similarity	NPC46998
0.7255	Intermediate Similarity	NPC128733
0.7255	Intermediate Similarity	NPC110443
0.7255	Intermediate Similarity	NPC133907
0.7255	Intermediate Similarity	NPC185141
0.7255	Intermediate Similarity	NPC244456
0.7255	Intermediate Similarity	NPC469851
0.7245	Intermediate Similarity	NPC125674
0.7245	Intermediate Similarity	NPC228451
0.7245	Intermediate Similarity	NPC469692
0.7245	Intermediate Similarity	NPC475838
0.7245	Intermediate Similarity	NPC469645
0.7238	Intermediate Similarity	NPC475074
0.7234	Intermediate Similarity	NPC67081
0.7234	Intermediate Similarity	NPC471223
0.7234	Intermediate Similarity	NPC261380
0.7234	Intermediate Similarity	NPC11804
0.7228	Intermediate Similarity	NPC141191
0.7228	Intermediate Similarity	NPC203627
0.7216	Intermediate Similarity	NPC475855
0.7216	Intermediate Similarity	NPC475879
0.7216	Intermediate Similarity	NPC232426
0.7216	Intermediate Similarity	NPC473448
0.7216	Intermediate Similarity	NPC281942
0.7209	Intermediate Similarity	NPC4299
0.7209	Intermediate Similarity	NPC315597
0.7209	Intermediate Similarity	NPC315285
0.7209	Intermediate Similarity	NPC316029
0.7209	Intermediate Similarity	NPC64234
0.7209	Intermediate Similarity	NPC37929
0.7204	Intermediate Similarity	NPC472377
0.7204	Intermediate Similarity	NPC131669
0.7204	Intermediate Similarity	NPC169575
0.7204	Intermediate Similarity	NPC473390
0.7204	Intermediate Similarity	NPC475714
0.7204	Intermediate Similarity	NPC40746
0.7204	Intermediate Similarity	NPC44261
0.72	Intermediate Similarity	NPC288350
0.72	Intermediate Similarity	NPC165632
0.72	Intermediate Similarity	NPC16967
0.72	Intermediate Similarity	NPC173329
0.72	Intermediate Similarity	NPC98165
0.7188	Intermediate Similarity	NPC26078
0.7188	Intermediate Similarity	NPC472809
0.7188	Intermediate Similarity	NPC476803
0.7188	Intermediate Similarity	NPC473658
0.7188	Intermediate Similarity	NPC471956
0.7188	Intermediate Similarity	NPC472810
0.7176	Intermediate Similarity	NPC474823
0.7176	Intermediate Similarity	NPC238223
0.7174	Intermediate Similarity	NPC315731
0.7174	Intermediate Similarity	NPC475944
0.7174	Intermediate Similarity	NPC52861
0.7174	Intermediate Similarity	NPC325031
0.7174	Intermediate Similarity	NPC24417
0.7172	Intermediate Similarity	NPC121825
0.7172	Intermediate Similarity	NPC470255
0.7172	Intermediate Similarity	NPC191521
0.7172	Intermediate Similarity	NPC474247
0.7158	Intermediate Similarity	NPC469910
0.7158	Intermediate Similarity	NPC469483
0.7158	Intermediate Similarity	NPC150755
0.7158	Intermediate Similarity	NPC116575
0.7157	Intermediate Similarity	NPC288876
0.7143	Intermediate Similarity	NPC471537
0.7143	Intermediate Similarity	NPC114345
0.7143	Intermediate Similarity	NPC469852
0.7143	Intermediate Similarity	NPC141831
0.7143	Intermediate Similarity	NPC303230
0.7143	Intermediate Similarity	NPC6099
0.7129	Intermediate Similarity	NPC53844
0.7129	Intermediate Similarity	NPC169205
0.7129	Intermediate Similarity	NPC475709
0.7128	Intermediate Similarity	NPC471301
0.7128	Intermediate Similarity	NPC154893
0.7128	Intermediate Similarity	NPC476804
0.7128	Intermediate Similarity	NPC16887
0.7128	Intermediate Similarity	NPC290052
0.7128	Intermediate Similarity	NPC53011
0.7128	Intermediate Similarity	NPC37005
0.7128	Intermediate Similarity	NPC82297
0.7115	Intermediate Similarity	NPC471938
0.7113	Intermediate Similarity	NPC470734
0.7113	Intermediate Similarity	NPC473564
0.7111	Intermediate Similarity	NPC474278
0.71	Intermediate Similarity	NPC90121
0.71	Intermediate Similarity	NPC476487
0.71	Intermediate Similarity	NPC275960
0.71	Intermediate Similarity	NPC48803
0.71	Intermediate Similarity	NPC13924
0.71	Intermediate Similarity	NPC193645
0.71	Intermediate Similarity	NPC476488
0.7097	Intermediate Similarity	NPC474028
0.7097	Intermediate Similarity	NPC475046
0.7097	Intermediate Similarity	NPC471298
0.7097	Intermediate Similarity	NPC310450
0.7097	Intermediate Similarity	NPC474959
0.7097	Intermediate Similarity	NPC11383
0.7097	Intermediate Similarity	NPC474439
0.7097	Intermediate Similarity	NPC323251
0.7093	Intermediate Similarity	NPC101622
0.7083	Intermediate Similarity	NPC237540
0.7083	Intermediate Similarity	NPC45409
0.7083	Intermediate Similarity	NPC313658
0.7083	Intermediate Similarity	NPC316138
0.7079	Intermediate Similarity	NPC329852
0.7075	Intermediate Similarity	NPC469853
0.7071	Intermediate Similarity	NPC475912
0.7071	Intermediate Similarity	NPC152778
0.7071	Intermediate Similarity	NPC29798

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 NPC225283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1609
0.2-0.3	3810
0.3-0.4	2557
0.4-0.5	735
0.5-0.6	235
0.6-0.7	44
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
0.71	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7838	Discovery
0.6947	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4225	Approved
0.6842	Remote Similarity	NPD7154	Phase 3
0.6804	Remote Similarity	NPD4249	Approved
0.6735	Remote Similarity	NPD4250	Approved
0.6735	Remote Similarity	NPD4251	Approved
0.6634	Remote Similarity	NPD7983	Approved
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5779	Approved
0.6569	Remote Similarity	NPD5778	Approved
0.6538	Remote Similarity	NPD7839	Suspended
0.6535	Remote Similarity	NPD6698	Approved
0.6535	Remote Similarity	NPD5785	Approved
0.6535	Remote Similarity	NPD46	Approved
0.6531	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4822	Approved
0.6526	Remote Similarity	NPD4819	Approved
0.6526	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4821	Approved
0.6526	Remote Similarity	NPD4820	Approved
0.6505	Remote Similarity	NPD5282	Discontinued
0.6471	Remote Similarity	NPD7637	Suspended
0.6437	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6371	Approved
0.6392	Remote Similarity	NPD5209	Approved
0.6364	Remote Similarity	NPD5363	Approved
0.6355	Remote Similarity	NPD6648	Approved
0.6327	Remote Similarity	NPD5362	Discontinued
0.6316	Remote Similarity	NPD6053	Discontinued
0.6316	Remote Similarity	NPD4268	Approved
0.6316	Remote Similarity	NPD4271	Approved
0.6296	Remote Similarity	NPD5344	Discontinued
0.6275	Remote Similarity	NPD1695	Approved
0.6275	Remote Similarity	NPD6101	Approved
0.6275	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6686	Approved
0.6228	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4269	Approved
0.6224	Remote Similarity	NPD4270	Approved
0.6167	Remote Similarity	NPD8516	Approved
0.6167	Remote Similarity	NPD8513	Phase 3
0.6167	Remote Similarity	NPD8517	Approved
0.6167	Remote Similarity	NPD8515	Approved
0.6162	Remote Similarity	NPD5331	Approved
0.6162	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD6411	Approved
0.6139	Remote Similarity	NPD5786	Approved
0.6122	Remote Similarity	NPD4790	Discontinued
0.6122	Remote Similarity	NPD5369	Approved
0.6102	Remote Similarity	NPD7505	Discontinued
0.61	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7639	Approved
0.6055	Remote Similarity	NPD7640	Approved
0.6042	Remote Similarity	NPD4756	Discovery
0.604	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.604	Remote Similarity	NPD1694	Approved
0.6033	Remote Similarity	NPD7503	Approved
0.602	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.5966	Remote Similarity	NPD7115	Discovery
0.5963	Remote Similarity	NPD7638	Approved
0.592	Remote Similarity	NPD8074	Phase 3
0.5917	Remote Similarity	NPD7327	Approved
0.5917	Remote Similarity	NPD7328	Approved
0.5902	Remote Similarity	NPD8033	Approved
0.59	Remote Similarity	NPD6435	Approved
0.5868	Remote Similarity	NPD7516	Approved
0.5827	Remote Similarity	NPD7319	Approved
0.582	Remote Similarity	NPD8294	Approved
0.582	Remote Similarity	NPD8377	Approved
0.5816	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5370	Suspended
0.5776	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD8378	Approved
0.5772	Remote Similarity	NPD8380	Approved
0.5772	Remote Similarity	NPD8296	Approved
0.5772	Remote Similarity	NPD8379	Approved
0.5772	Remote Similarity	NPD8335	Approved
0.5769	Remote Similarity	NPD7524	Approved
0.5769	Remote Similarity	NPD7750	Discontinued
0.5763	Remote Similarity	NPD969	Suspended
0.573	Remote Similarity	NPD368	Approved
0.5728	Remote Similarity	NPD1696	Phase 3
0.5714	Remote Similarity	NPD7507	Approved
0.5701	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5368	Approved
0.57	Remote Similarity	NPD6930	Phase 2
0.57	Remote Similarity	NPD6931	Approved
0.568	Remote Similarity	NPD7829	Approved
0.568	Remote Similarity	NPD7830	Approved
0.567	Remote Similarity	NPD8039	Approved
0.5664	Remote Similarity	NPD7632	Discontinued
0.5652	Remote Similarity	NPD4211	Phase 1
0.5639	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6647	Phase 2
0.56	Remote Similarity	NPD8080	Discontinued
0.56	Remote Similarity	NPD6929	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