NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	1.758
LogD:	1.686
LogS:	-2.859
# Rotatable Bonds:	0
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.634
Synthetic Accessibility Score:	5.103
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.692
MDCK Permeability:	1.4538447430822998e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.851
Plasma Protein Binding (PPB):	90.9724349975586%
Volume Distribution (VD):	1.779
Pgp-substrate:	11.109308242797852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.235
CYP1A2-substrate:	0.666
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.32
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.436
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	7.038
Half-life (T1/2):	0.674

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.715
Drug-inuced Liver Injury (DILI):	0.804
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.566
Skin Sensitization:	0.689
Carcinogencity:	0.674
Eye Corrosion:	0.054
Eye Irritation:	0.491
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC471185

Natural Product ID:	NPC471185
*Common Name:**	5Beta,10Beta-Dihydroxy-1Alpha,4Betahguai-7(11),8-Dien-12,8-Olide
IUPAC Name:	(5S,5aS,8R,8aS)-5,8a-dihydroxy-1,5,8-trimethyl-6,7,8,9-tetrahydro-5aH-azuleno[6,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	GWHGITGZQCFTQM-QATIJOQPSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8-4-5-12-14(3,17)7-11-10(6-15(8,12)18)9(2)13(16)19-11/h7-8,12,17-18H,4-6H2,1-3H3/t8-,12+,14+,15+/m1/s1
SMILES:	CC1CCC2C1(CC3=C(C(=O)OC3=CC2(C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386507
PubChem CID:	71725780
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	30100.0	nM	PMID[565028]

☑ 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 NPC471185 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	170
0.1-0.2	1224
0.2-0.3	5175
0.3-0.4	15001
0.4-0.5	12955
0.5-0.6	6216
0.6-0.7	1769
0.7-0.8	170
0.8-0.85	11
0.85-0.9	1
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC191283
0.9186	High Similarity	NPC40821
0.9186	High Similarity	NPC32862
0.9186	High Similarity	NPC272293
0.8372	Intermediate Similarity	NPC146850
0.8372	Intermediate Similarity	NPC287015
0.8333	Intermediate Similarity	NPC59994
0.8333	Intermediate Similarity	NPC78677
0.8256	Intermediate Similarity	NPC290052
0.8046	Intermediate Similarity	NPC154893
0.8046	Intermediate Similarity	NPC53011
0.8046	Intermediate Similarity	NPC37005
0.8046	Intermediate Similarity	NPC16887
0.8	Intermediate Similarity	NPC212664
0.8	Intermediate Similarity	NPC225283
0.7955	Intermediate Similarity	NPC245434
0.7935	Intermediate Similarity	NPC472954
0.7912	Intermediate Similarity	NPC3436
0.7895	Intermediate Similarity	NPC64742
0.7889	Intermediate Similarity	NPC260343
0.7826	Intermediate Similarity	NPC2882
0.7826	Intermediate Similarity	NPC470520
0.7812	Intermediate Similarity	NPC469872
0.7812	Intermediate Similarity	NPC469864
0.7766	Intermediate Similarity	NPC469873
0.7742	Intermediate Similarity	NPC59646
0.7684	Intermediate Similarity	NPC9812
0.766	Intermediate Similarity	NPC96541
0.766	Intermediate Similarity	NPC470521
0.7634	Intermediate Similarity	NPC32494
0.7634	Intermediate Similarity	NPC175842
0.7582	Intermediate Similarity	NPC45957
0.7582	Intermediate Similarity	NPC471657
0.7579	Intermediate Similarity	NPC220221
0.7579	Intermediate Similarity	NPC67584
0.7579	Intermediate Similarity	NPC52044
0.7576	Intermediate Similarity	NPC183570
0.7576	Intermediate Similarity	NPC280566
0.7561	Intermediate Similarity	NPC315597
0.7561	Intermediate Similarity	NPC316029
0.7551	Intermediate Similarity	NPC206079
0.7529	Intermediate Similarity	NPC476317
0.7526	Intermediate Similarity	NPC221615
0.7526	Intermediate Similarity	NPC244411
0.75	Intermediate Similarity	NPC272632
0.75	Intermediate Similarity	NPC309190
0.75	Intermediate Similarity	NPC471956
0.75	Intermediate Similarity	NPC213078
0.75	Intermediate Similarity	NPC98165
0.7449	Intermediate Similarity	NPC290802
0.7444	Intermediate Similarity	NPC156485
0.7442	Intermediate Similarity	NPC103987
0.7442	Intermediate Similarity	NPC476439
0.7442	Intermediate Similarity	NPC53581
0.7442	Intermediate Similarity	NPC315394
0.7439	Intermediate Similarity	NPC232812
0.7423	Intermediate Similarity	NPC161493
0.7412	Intermediate Similarity	NPC85831
0.7412	Intermediate Similarity	NPC265921
0.7412	Intermediate Similarity	NPC215215
0.7396	Intermediate Similarity	NPC170120
0.7396	Intermediate Similarity	NPC37408
0.7374	Intermediate Similarity	NPC150923
0.7374	Intermediate Similarity	NPC116139
0.7374	Intermediate Similarity	NPC62670
0.7349	Intermediate Similarity	NPC315285
0.7349	Intermediate Similarity	NPC64234
0.7349	Intermediate Similarity	NPC37929
0.7347	Intermediate Similarity	NPC181147
0.734	Intermediate Similarity	NPC129419
0.734	Intermediate Similarity	NPC301969
0.734	Intermediate Similarity	NPC37607
0.734	Intermediate Similarity	NPC471184
0.7327	Intermediate Similarity	NPC121099
0.732	Intermediate Similarity	NPC473333
0.7317	Intermediate Similarity	NPC313444
0.7312	Intermediate Similarity	NPC26078
0.7312	Intermediate Similarity	NPC473658
0.73	Intermediate Similarity	NPC66110
0.7292	Intermediate Similarity	NPC470013
0.7292	Intermediate Similarity	NPC127019
0.7292	Intermediate Similarity	NPC477131
0.7292	Intermediate Similarity	NPC262133
0.7292	Intermediate Similarity	NPC323008
0.7292	Intermediate Similarity	NPC470010
0.7273	Intermediate Similarity	NPC227865
0.7253	Intermediate Similarity	NPC474693
0.7245	Intermediate Similarity	NPC477949
0.7245	Intermediate Similarity	NPC2666
0.7241	Intermediate Similarity	NPC54996
0.7241	Intermediate Similarity	NPC316324
0.7234	Intermediate Similarity	NPC64913
0.7234	Intermediate Similarity	NPC51358
0.7234	Intermediate Similarity	NPC242877
0.7234	Intermediate Similarity	NPC268298
0.7234	Intermediate Similarity	NPC307092
0.7222	Intermediate Similarity	NPC89555
0.7216	Intermediate Similarity	NPC471492
0.7216	Intermediate Similarity	NPC213698
0.7204	Intermediate Similarity	NPC237540
0.72	Intermediate Similarity	NPC477950
0.7174	Intermediate Similarity	NPC475860
0.7174	Intermediate Similarity	NPC474694
0.7174	Intermediate Similarity	NPC78089
0.7174	Intermediate Similarity	NPC473659
0.7174	Intermediate Similarity	NPC165162
0.7159	Intermediate Similarity	NPC470944
0.7157	Intermediate Similarity	NPC200861
0.7157	Intermediate Similarity	NPC472822
0.7143	Intermediate Similarity	NPC238850
0.7129	Intermediate Similarity	NPC197835
0.7129	Intermediate Similarity	NPC140591
0.7129	Intermediate Similarity	NPC303653
0.7129	Intermediate Similarity	NPC189609
0.7129	Intermediate Similarity	NPC291500
0.7126	Intermediate Similarity	NPC152017
0.7113	Intermediate Similarity	NPC198853
0.7111	Intermediate Similarity	NPC112868
0.7111	Intermediate Similarity	NPC325031
0.71	Intermediate Similarity	NPC280963
0.7097	Intermediate Similarity	NPC107787
0.7097	Intermediate Similarity	NPC67493
0.7093	Intermediate Similarity	NPC470686
0.7083	Intermediate Similarity	NPC131209
0.7083	Intermediate Similarity	NPC475925
0.7083	Intermediate Similarity	NPC133698
0.7079	Intermediate Similarity	NPC471890
0.7079	Intermediate Similarity	NPC66677
0.7079	Intermediate Similarity	NPC84185
0.7073	Intermediate Similarity	NPC230107
0.7073	Intermediate Similarity	NPC315115
0.7071	Intermediate Similarity	NPC471490
0.7071	Intermediate Similarity	NPC202705
0.7065	Intermediate Similarity	NPC165287
0.7059	Intermediate Similarity	NPC124881
0.7041	Intermediate Similarity	NPC304886
0.7024	Intermediate Similarity	NPC265574
0.7011	Intermediate Similarity	NPC329852
0.701	Intermediate Similarity	NPC1108
0.6979	Remote Similarity	NPC77337
0.6979	Remote Similarity	NPC473448
0.697	Remote Similarity	NPC16967
0.6966	Remote Similarity	NPC63445
0.6966	Remote Similarity	NPC222210
0.6966	Remote Similarity	NPC476627
0.6966	Remote Similarity	NPC299235
0.6966	Remote Similarity	NPC315765
0.6961	Remote Similarity	NPC86077
0.6957	Remote Similarity	NPC472377
0.6957	Remote Similarity	NPC245665
0.6957	Remote Similarity	NPC321385
0.6957	Remote Similarity	NPC474809
0.6957	Remote Similarity	NPC472473
0.6947	Remote Similarity	NPC60765
0.6947	Remote Similarity	NPC242448
0.6947	Remote Similarity	NPC79549
0.6939	Remote Similarity	NPC120351
0.6939	Remote Similarity	NPC191521
0.6939	Remote Similarity	NPC166143
0.6939	Remote Similarity	NPC167219
0.6939	Remote Similarity	NPC471994
0.6923	Remote Similarity	NPC81630
0.6923	Remote Similarity	NPC474894
0.6923	Remote Similarity	NPC223450
0.6923	Remote Similarity	NPC243998
0.6923	Remote Similarity	NPC470241
0.6916	Remote Similarity	NPC255401
0.6916	Remote Similarity	NPC471484
0.6916	Remote Similarity	NPC284162
0.6916	Remote Similarity	NPC262083
0.6915	Remote Similarity	NPC305475
0.6915	Remote Similarity	NPC475461
0.6907	Remote Similarity	NPC111114
0.6907	Remote Similarity	NPC300312
0.6907	Remote Similarity	NPC261607
0.6907	Remote Similarity	NPC45579
0.69	Remote Similarity	NPC47834
0.6889	Remote Similarity	NPC182550
0.6889	Remote Similarity	NPC55304
0.6889	Remote Similarity	NPC471537
0.6889	Remote Similarity	NPC472013
0.6889	Remote Similarity	NPC226226
0.6889	Remote Similarity	NPC476624
0.6887	Remote Similarity	NPC137911
0.6887	Remote Similarity	NPC475274
0.6887	Remote Similarity	NPC228477
0.6887	Remote Similarity	NPC75389
0.6882	Remote Similarity	NPC114979
0.6882	Remote Similarity	NPC191476
0.6882	Remote Similarity	NPC475706
0.6882	Remote Similarity	NPC115786
0.6882	Remote Similarity	NPC90446
0.6882	Remote Similarity	NPC82297
0.6881	Remote Similarity	NPC106446
0.6875	Remote Similarity	NPC212598
0.6875	Remote Similarity	NPC215556
0.6875	Remote Similarity	NPC32922
0.6867	Remote Similarity	NPC191233
0.6863	Remote Similarity	NPC219038
0.686	Remote Similarity	NPC106309

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 NPC471185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1643
0.2-0.3	3995
0.3-0.4	2452
0.4-0.5	625
0.5-0.6	243
0.6-0.7	37
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
0.6989	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4249	Approved
0.6852	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD4250	Approved
0.6842	Remote Similarity	NPD4251	Approved
0.6813	Remote Similarity	NPD4820	Approved
0.6813	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4822	Approved
0.6813	Remote Similarity	NPD4821	Approved
0.6813	Remote Similarity	NPD4819	Approved
0.6774	Remote Similarity	NPD5362	Discontinued
0.6633	Remote Similarity	NPD7838	Discovery
0.6596	Remote Similarity	NPD7154	Phase 3
0.6596	Remote Similarity	NPD5332	Approved
0.6596	Remote Similarity	NPD5331	Approved
0.6593	Remote Similarity	NPD4268	Approved
0.6593	Remote Similarity	NPD4271	Approved
0.6559	Remote Similarity	NPD4790	Discontinued
0.6542	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1695	Approved
0.6514	Remote Similarity	NPD6371	Approved
0.6465	Remote Similarity	NPD5785	Approved
0.64	Remote Similarity	NPD5281	Approved
0.64	Remote Similarity	NPD7637	Suspended
0.64	Remote Similarity	NPD5284	Approved
0.6354	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5363	Approved
0.6286	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.6238	Remote Similarity	NPD5693	Phase 1
0.6214	Remote Similarity	NPD5695	Phase 3
0.619	Remote Similarity	NPD4225	Approved
0.619	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4269	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6146	Remote Similarity	NPD6435	Approved
0.6146	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4270	Approved
0.6139	Remote Similarity	NPD46	Approved
0.6139	Remote Similarity	NPD5692	Phase 3
0.6139	Remote Similarity	NPD5207	Approved
0.6139	Remote Similarity	NPD6698	Approved
0.6132	Remote Similarity	NPD7640	Approved
0.6132	Remote Similarity	NPD7639	Approved
0.6129	Remote Similarity	NPD4756	Discovery
0.6102	Remote Similarity	NPD7503	Approved
0.6095	Remote Similarity	NPD6084	Phase 2
0.6095	Remote Similarity	NPD6083	Phase 2
0.6078	Remote Similarity	NPD6050	Approved
0.6078	Remote Similarity	NPD5694	Approved
0.6075	Remote Similarity	NPD5344	Discontinued
0.6064	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5786	Approved
0.6042	Remote Similarity	NPD5369	Approved
0.604	Remote Similarity	NPD6051	Approved
0.6038	Remote Similarity	NPD5696	Approved
0.6038	Remote Similarity	NPD7638	Approved
0.6019	Remote Similarity	NPD5779	Approved
0.6019	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD7524	Approved
0.5983	Remote Similarity	NPD7328	Approved
0.5983	Remote Similarity	NPD7327	Approved
0.5966	Remote Similarity	NPD8033	Approved
0.5962	Remote Similarity	NPD5282	Discontinued
0.5941	Remote Similarity	NPD4518	Approved
0.5938	Remote Similarity	NPD4252	Approved
0.5938	Remote Similarity	NPD6931	Approved
0.5938	Remote Similarity	NPD5368	Approved
0.5938	Remote Similarity	NPD6930	Phase 2
0.5932	Remote Similarity	NPD7516	Approved
0.5922	Remote Similarity	NPD7983	Approved
0.5905	Remote Similarity	NPD5654	Approved
0.59	Remote Similarity	NPD5280	Approved
0.59	Remote Similarity	NPD4694	Approved
0.5897	Remote Similarity	NPD7115	Discovery
0.5893	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD6673	Approved
0.5882	Remote Similarity	NPD6904	Approved
0.5882	Remote Similarity	NPD8294	Approved
0.5882	Remote Similarity	NPD6080	Approved
0.5882	Remote Similarity	NPD8377	Approved
0.5865	Remote Similarity	NPD6399	Phase 3
0.5856	Remote Similarity	NPD5739	Approved
0.5856	Remote Similarity	NPD6402	Approved
0.5856	Remote Similarity	NPD7128	Approved
0.5856	Remote Similarity	NPD6675	Approved
0.5833	Remote Similarity	NPD8380	Approved
0.5833	Remote Similarity	NPD8378	Approved
0.5833	Remote Similarity	NPD8379	Approved
0.5833	Remote Similarity	NPD6929	Approved
0.5833	Remote Similarity	NPD8296	Approved
0.5833	Remote Similarity	NPD4195	Approved
0.5833	Remote Similarity	NPD8335	Approved
0.5816	Remote Similarity	NPD4221	Approved
0.5816	Remote Similarity	NPD4223	Phase 3
0.5806	Remote Similarity	NPD6926	Approved
0.5806	Remote Similarity	NPD6924	Approved
0.5804	Remote Similarity	NPD5697	Approved
0.5804	Remote Similarity	NPD5701	Approved
0.58	Remote Similarity	NPD1694	Approved
0.5794	Remote Similarity	NPD5959	Approved
0.5784	Remote Similarity	NPD5208	Approved
0.5773	Remote Similarity	NPD7514	Phase 3
0.5772	Remote Similarity	NPD7507	Approved
0.5769	Remote Similarity	NPD7087	Discontinued
0.5763	Remote Similarity	NPD7505	Discontinued
0.5755	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6686	Approved
0.5752	Remote Similarity	NPD6899	Approved
0.5752	Remote Similarity	NPD6881	Approved
0.5728	Remote Similarity	NPD4753	Phase 2
0.5728	Remote Similarity	NPD6101	Approved
0.5728	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7632	Discontinued
0.5702	Remote Similarity	NPD6372	Approved
0.5702	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD6014	Approved
0.5702	Remote Similarity	NPD6012	Approved
0.5702	Remote Similarity	NPD6373	Approved
0.5701	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4197	Approved
0.5688	Remote Similarity	NPD6404	Discontinued
0.5684	Remote Similarity	NPD6933	Approved
0.5673	Remote Similarity	NPD4096	Approved
0.566	Remote Similarity	NPD6001	Approved
0.5657	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6883	Approved
0.5652	Remote Similarity	NPD7290	Approved
0.5652	Remote Similarity	NPD7102	Approved
0.5644	Remote Similarity	NPD5329	Approved
0.5644	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6893	Approved
0.5644	Remote Similarity	NPD1696	Phase 3
0.5635	Remote Similarity	NPD7319	Approved
0.5632	Remote Similarity	NPD4192	Approved
0.5632	Remote Similarity	NPD4194	Approved
0.5632	Remote Similarity	NPD4191	Approved
0.5632	Remote Similarity	NPD4193	Approved
0.5631	Remote Similarity	NPD5737	Approved
0.5631	Remote Similarity	NPD6903	Approved
0.5631	Remote Similarity	NPD6672	Approved
0.5625	Remote Similarity	NPD6925	Approved
0.5625	Remote Similarity	NPD5909	Discontinued
0.5625	Remote Similarity	NPD5776	Phase 2
0.5619	Remote Similarity	NPD6411	Approved
0.5614	Remote Similarity	NPD6011	Approved
0.5612	Remote Similarity	NPD7332	Phase 2
0.5603	Remote Similarity	NPD6649	Approved
0.5603	Remote Similarity	NPD6650	Approved
0.5603	Remote Similarity	NPD6617	Approved
0.5603	Remote Similarity	NPD6869	Approved
0.5603	Remote Similarity	NPD6847	Approved
0.5603	Remote Similarity	NPD8130	Phase 1

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