NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	484.25
Volume:	487.418
LogP:	4.591
LogD:	4.17
LogS:	-2.444
# Rotatable Bonds:	10
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	4.79
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:	-5.25
MDCK Permeability:	9.599577424523886e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.645
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	97.94388580322266%
Volume Distribution (VD):	1.547
Pgp-substrate:	1.6073607206344604%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.417
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.337
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.385
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	2.784
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.608
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.704
Carcinogencity:	0.866
Eye Corrosion:	0.476
Eye Irritation:	0.586
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC477122

Natural Product ID:	NPC477122
*Common Name:**	25-Hydroxyhalisulfate 9
IUPAC Name:	[2-[2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl]-5-(2-hydroxy-5-oxo-2H-furan-3-yl)pentyl] hydrogen sulfate
Synonyms:	25-Hydroxyhalisulfate 9
Standard InCHIKey:	UTGHYWBAVNHHJG-TYMBNJMISA-N
Standard InCHI:	InChI=1S/C25H40O7S/c1-17-10-11-20-21(9-6-13-24(20,2)3)25(17,4)14-12-18(16-31-33(28,29)30)7-5-8-19-15-22(26)32-23(19)27/h9,15,17-18,20,23,27H,5-8,10-14,16H2,1-4H3,(H,28,29,30)/t17-,18?,20-,23?,25-/m0/s1
SMILES:	C[C@H]1CC[C@H]2C(=CCCC2(C)C)[C@@]1(C)CCC(CCCC3=CC(=O)OC3O)COS(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	25242870
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
NPO33581	Fasciospongia sp.	Species	Thorectidae	Eukaryota	n.a.	at a depth of 1 m in Palau	2003-DEC	PMID[19178162]

☑ 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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	19	mm	PMID[19178162]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	13	mm	PMID[19178162]

☑ 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 NPC477122 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	169
0.1-0.2	1299
0.2-0.3	5116
0.3-0.4	14813
0.4-0.5	9762
0.5-0.6	7463
0.6-0.7	3488
0.7-0.8	540
0.8-0.85	31
0.85-0.9	10
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9326	High Similarity	NPC324078
0.9294	High Similarity	NPC473251
0.9294	High Similarity	NPC42586
0.9091	High Similarity	NPC470734
0.9059	High Similarity	NPC477124
0.8901	High Similarity	NPC104925
0.8901	High Similarity	NPC298973
0.8837	High Similarity	NPC472440
0.8764	High Similarity	NPC472809
0.8764	High Similarity	NPC472810
0.8696	High Similarity	NPC469697
0.8636	High Similarity	NPC472442
0.8571	High Similarity	NPC477782
0.8556	High Similarity	NPC474629
0.8523	High Similarity	NPC471302
0.8523	High Similarity	NPC471301
0.8511	High Similarity	NPC162346
0.8506	High Similarity	NPC471298
0.8478	Intermediate Similarity	NPC477783
0.8478	Intermediate Similarity	NPC472811
0.8421	Intermediate Similarity	NPC477719
0.8421	Intermediate Similarity	NPC477718
0.8409	Intermediate Similarity	NPC471297
0.8404	Intermediate Similarity	NPC472441
0.8387	Intermediate Similarity	NPC472812
0.8353	Intermediate Similarity	NPC473756
0.8333	Intermediate Similarity	NPC474062
0.8315	Intermediate Similarity	NPC470800
0.8315	Intermediate Similarity	NPC318515
0.8298	Intermediate Similarity	NPC470255
0.828	Intermediate Similarity	NPC329842
0.8261	Intermediate Similarity	NPC251528
0.8247	Intermediate Similarity	NPC324841
0.8247	Intermediate Similarity	NPC477716
0.8247	Intermediate Similarity	NPC477720
0.8247	Intermediate Similarity	NPC477721
0.8222	Intermediate Similarity	NPC329630
0.8202	Intermediate Similarity	NPC311070
0.8172	Intermediate Similarity	NPC78973
0.8172	Intermediate Similarity	NPC232426
0.8172	Intermediate Similarity	NPC281942
0.8163	Intermediate Similarity	NPC477717
0.8161	Intermediate Similarity	NPC242767
0.8152	Intermediate Similarity	NPC472378
0.8125	Intermediate Similarity	NPC470801
0.8125	Intermediate Similarity	NPC319692
0.8125	Intermediate Similarity	NPC325960
0.8111	Intermediate Similarity	NPC126518
0.8105	Intermediate Similarity	NPC474554
0.809	Intermediate Similarity	NPC324170
0.809	Intermediate Similarity	NPC323251
0.8085	Intermediate Similarity	NPC141831
0.8085	Intermediate Similarity	NPC165904
0.8085	Intermediate Similarity	NPC179517
0.8065	Intermediate Similarity	NPC174342
0.8065	Intermediate Similarity	NPC5509
0.8041	Intermediate Similarity	NPC475709
0.8041	Intermediate Similarity	NPC98112
0.8022	Intermediate Similarity	NPC30984
0.8022	Intermediate Similarity	NPC163606
0.8	Intermediate Similarity	NPC166346
0.8	Intermediate Similarity	NPC324243
0.8	Intermediate Similarity	NPC42476
0.798	Intermediate Similarity	NPC63249
0.7979	Intermediate Similarity	NPC469403
0.7955	Intermediate Similarity	NPC17550
0.7938	Intermediate Similarity	NPC17578
0.7938	Intermediate Similarity	NPC240673
0.7935	Intermediate Similarity	NPC471219
0.7935	Intermediate Similarity	NPC131813
0.7917	Intermediate Similarity	NPC474555
0.7912	Intermediate Similarity	NPC71626
0.79	Intermediate Similarity	NPC472815
0.79	Intermediate Similarity	NPC134077
0.7889	Intermediate Similarity	NPC256112
0.7889	Intermediate Similarity	NPC471218
0.7849	Intermediate Similarity	NPC312561
0.7826	Intermediate Similarity	NPC474860
0.7826	Intermediate Similarity	NPC471795
0.7826	Intermediate Similarity	NPC65661
0.7826	Intermediate Similarity	NPC86316
0.7826	Intermediate Similarity	NPC471300
0.7826	Intermediate Similarity	NPC106416
0.7812	Intermediate Similarity	NPC242069
0.7812	Intermediate Similarity	NPC53555
0.7812	Intermediate Similarity	NPC115021
0.7812	Intermediate Similarity	NPC472303
0.7802	Intermediate Similarity	NPC472377
0.7802	Intermediate Similarity	NPC474809
0.7802	Intermediate Similarity	NPC476927
0.78	Intermediate Similarity	NPC471075
0.7778	Intermediate Similarity	NPC475944
0.7778	Intermediate Similarity	NPC474440
0.7778	Intermediate Similarity	NPC473154
0.7755	Intermediate Similarity	NPC165632
0.7742	Intermediate Similarity	NPC173917
0.7742	Intermediate Similarity	NPC118266
0.7732	Intermediate Similarity	NPC477722
0.7732	Intermediate Similarity	NPC105490
0.7708	Intermediate Similarity	NPC289479
0.7708	Intermediate Similarity	NPC65513
0.77	Intermediate Similarity	NPC477968
0.77	Intermediate Similarity	NPC219285
0.77	Intermediate Similarity	NPC20113
0.77	Intermediate Similarity	NPC228251
0.77	Intermediate Similarity	NPC476767
0.77	Intermediate Similarity	NPC161527
0.77	Intermediate Similarity	NPC472826
0.77	Intermediate Similarity	NPC477971
0.77	Intermediate Similarity	NPC477972
0.7692	Intermediate Similarity	NPC2524
0.7692	Intermediate Similarity	NPC470024
0.7692	Intermediate Similarity	NPC38948
0.7684	Intermediate Similarity	NPC168131
0.7684	Intermediate Similarity	NPC293044
0.7677	Intermediate Similarity	NPC208094
0.7677	Intermediate Similarity	NPC476253
0.7674	Intermediate Similarity	NPC476489
0.7674	Intermediate Similarity	NPC476490
0.767	Intermediate Similarity	NPC172867
0.7667	Intermediate Similarity	NPC10636
0.766	Intermediate Similarity	NPC475678
0.766	Intermediate Similarity	NPC166857
0.766	Intermediate Similarity	NPC471796
0.7653	Intermediate Similarity	NPC276110
0.7647	Intermediate Similarity	NPC120009
0.764	Intermediate Similarity	NPC474816
0.764	Intermediate Similarity	NPC209135
0.7634	Intermediate Similarity	NPC189311
0.7634	Intermediate Similarity	NPC474694
0.7634	Intermediate Similarity	NPC475860
0.7634	Intermediate Similarity	NPC119001
0.7634	Intermediate Similarity	NPC35933
0.7634	Intermediate Similarity	NPC473659
0.7634	Intermediate Similarity	NPC474013
0.7634	Intermediate Similarity	NPC217394
0.7629	Intermediate Similarity	NPC7349
0.7629	Intermediate Similarity	NPC469939
0.7619	Intermediate Similarity	NPC206618
0.7609	Intermediate Similarity	NPC23748
0.7604	Intermediate Similarity	NPC51486
0.7604	Intermediate Similarity	NPC280149
0.7604	Intermediate Similarity	NPC182136
0.7604	Intermediate Similarity	NPC470817
0.7604	Intermediate Similarity	NPC221111
0.76	Intermediate Similarity	NPC325229
0.76	Intermediate Similarity	NPC275086
0.7596	Intermediate Similarity	NPC109376
0.7596	Intermediate Similarity	NPC475074
0.7582	Intermediate Similarity	NPC40228
0.7582	Intermediate Similarity	NPC229584
0.7582	Intermediate Similarity	NPC14203
0.7582	Intermediate Similarity	NPC170303
0.7576	Intermediate Similarity	NPC190713
0.7551	Intermediate Similarity	NPC475572
0.7549	Intermediate Similarity	NPC238397
0.7549	Intermediate Similarity	NPC471363
0.7528	Intermediate Similarity	NPC262747
0.7527	Intermediate Similarity	NPC474693
0.7526	Intermediate Similarity	NPC234335
0.7526	Intermediate Similarity	NPC472814
0.7526	Intermediate Similarity	NPC177037
0.7525	Intermediate Similarity	NPC38855
0.7525	Intermediate Similarity	NPC472644
0.7524	Intermediate Similarity	NPC224660
0.7524	Intermediate Similarity	NPC476765
0.75	Intermediate Similarity	NPC218158
0.75	Intermediate Similarity	NPC474396
0.75	Intermediate Similarity	NPC257726
0.75	Intermediate Similarity	NPC50488
0.75	Intermediate Similarity	NPC246028
0.75	Intermediate Similarity	NPC200513
0.75	Intermediate Similarity	NPC471296
0.75	Intermediate Similarity	NPC239547
0.75	Intermediate Similarity	NPC122945
0.75	Intermediate Similarity	NPC53844
0.75	Intermediate Similarity	NPC91197
0.75	Intermediate Similarity	NPC125551
0.75	Intermediate Similarity	NPC309503
0.75	Intermediate Similarity	NPC155319
0.75	Intermediate Similarity	NPC109938
0.75	Intermediate Similarity	NPC204054
0.75	Intermediate Similarity	NPC470819
0.75	Intermediate Similarity	NPC51499
0.75	Intermediate Similarity	NPC96597
0.7477	Intermediate Similarity	NPC17791
0.7476	Intermediate Similarity	NPC7613
0.7476	Intermediate Similarity	NPC281378
0.7476	Intermediate Similarity	NPC134270
0.7476	Intermediate Similarity	NPC475889
0.7476	Intermediate Similarity	NPC45897
0.7476	Intermediate Similarity	NPC127933
0.7476	Intermediate Similarity	NPC7644
0.7475	Intermediate Similarity	NPC293052
0.7475	Intermediate Similarity	NPC13924
0.7475	Intermediate Similarity	NPC295347
0.7473	Intermediate Similarity	NPC473685
0.7473	Intermediate Similarity	NPC206062
0.7473	Intermediate Similarity	NPC281880
0.7453	Intermediate Similarity	NPC476759

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 NPC477122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1554
0.2-0.3	4088
0.3-0.4	2439
0.4-0.5	561
0.5-0.6	285
0.6-0.7	82
0.7-0.8	3
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
0.8111	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6686	Approved
0.7353	Intermediate Similarity	NPD7639	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7255	Intermediate Similarity	NPD7638	Approved
0.7087	Intermediate Similarity	NPD4225	Approved
0.697	Remote Similarity	NPD6051	Approved
0.693	Remote Similarity	NPD7328	Approved
0.693	Remote Similarity	NPD7327	Approved
0.687	Remote Similarity	NPD7516	Approved
0.6827	Remote Similarity	NPD6084	Phase 2
0.6827	Remote Similarity	NPD6083	Phase 2
0.681	Remote Similarity	NPD8294	Approved
0.681	Remote Similarity	NPD8377	Approved
0.6752	Remote Similarity	NPD8378	Approved
0.6752	Remote Similarity	NPD8033	Approved
0.6752	Remote Similarity	NPD8380	Approved
0.6752	Remote Similarity	NPD7503	Approved
0.6752	Remote Similarity	NPD8296	Approved
0.6752	Remote Similarity	NPD8335	Approved
0.6752	Remote Similarity	NPD8379	Approved
0.6729	Remote Similarity	NPD7632	Discontinued
0.67	Remote Similarity	NPD5737	Approved
0.67	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD5695	Phase 3
0.6602	Remote Similarity	NPD6399	Phase 3
0.6566	Remote Similarity	NPD1694	Approved
0.6552	Remote Similarity	NPD7115	Discovery
0.6535	Remote Similarity	NPD6903	Approved
0.6535	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7507	Approved
0.6509	Remote Similarity	NPD7902	Approved
0.6505	Remote Similarity	NPD5693	Phase 1
0.6505	Remote Similarity	NPD7637	Suspended
0.6465	Remote Similarity	NPD3665	Phase 1
0.6465	Remote Similarity	NPD3668	Phase 3
0.6465	Remote Similarity	NPD3133	Approved
0.6465	Remote Similarity	NPD3666	Approved
0.6449	Remote Similarity	NPD5696	Approved
0.6408	Remote Similarity	NPD5785	Approved
0.6396	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD5739	Approved
0.6396	Remote Similarity	NPD6675	Approved
0.6396	Remote Similarity	NPD7128	Approved
0.6383	Remote Similarity	NPD8039	Approved
0.6383	Remote Similarity	NPD7339	Approved
0.6383	Remote Similarity	NPD6942	Approved
0.6372	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7319	Approved
0.6364	Remote Similarity	NPD6695	Phase 3
0.6364	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6882	Approved
0.6337	Remote Similarity	NPD4519	Discontinued
0.6337	Remote Similarity	NPD4623	Approved
0.6337	Remote Similarity	NPD3618	Phase 1
0.633	Remote Similarity	NPD5344	Discontinued
0.6316	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4753	Phase 2
0.6311	Remote Similarity	NPD5328	Approved
0.6311	Remote Similarity	NPD6904	Approved
0.6311	Remote Similarity	NPD6673	Approved
0.6311	Remote Similarity	NPD6080	Approved
0.63	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4786	Approved
0.6296	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4195	Approved
0.6289	Remote Similarity	NPD7645	Phase 2
0.6286	Remote Similarity	NPD5778	Approved
0.6286	Remote Similarity	NPD5779	Approved
0.6283	Remote Similarity	NPD6881	Approved
0.6283	Remote Similarity	NPD7320	Approved
0.6283	Remote Similarity	NPD6899	Approved
0.6263	Remote Similarity	NPD3667	Approved
0.6261	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6404	Discontinued
0.6238	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6372	Approved
0.6228	Remote Similarity	NPD6373	Approved
0.6226	Remote Similarity	NPD7900	Approved
0.6226	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7525	Registered
0.6211	Remote Similarity	NPD8264	Approved
0.6207	Remote Similarity	NPD6053	Discontinued
0.6195	Remote Similarity	NPD5701	Approved
0.6195	Remote Similarity	NPD5697	Approved
0.619	Remote Similarity	NPD5281	Approved
0.619	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD6050	Approved
0.619	Remote Similarity	NPD5284	Approved
0.619	Remote Similarity	NPD6079	Approved
0.6186	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5279	Phase 3
0.6174	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7290	Approved
0.6174	Remote Similarity	NPD7102	Approved
0.6174	Remote Similarity	NPD6883	Approved
0.6168	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6011	Approved
0.6136	Remote Similarity	NPD4193	Approved
0.6136	Remote Similarity	NPD4192	Approved
0.6136	Remote Similarity	NPD4191	Approved
0.6136	Remote Similarity	NPD4194	Approved
0.6122	Remote Similarity	NPD6929	Approved
0.6121	Remote Similarity	NPD6847	Approved
0.6121	Remote Similarity	NPD6649	Approved
0.6121	Remote Similarity	NPD6869	Approved
0.6121	Remote Similarity	NPD8130	Phase 1
0.6121	Remote Similarity	NPD6650	Approved
0.6121	Remote Similarity	NPD6617	Approved
0.6117	Remote Similarity	NPD7524	Approved
0.6117	Remote Similarity	NPD7750	Discontinued
0.6117	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6926	Approved
0.6105	Remote Similarity	NPD6924	Approved
0.61	Remote Similarity	NPD4221	Approved
0.61	Remote Similarity	NPD4223	Phase 3
0.6095	Remote Similarity	NPD7838	Discovery
0.6095	Remote Similarity	NPD46	Approved
0.6095	Remote Similarity	NPD5692	Phase 3
0.6095	Remote Similarity	NPD6698	Approved
0.6091	Remote Similarity	NPD6648	Approved
0.6087	Remote Similarity	NPD6014	Approved
0.6087	Remote Similarity	NPD6012	Approved
0.6087	Remote Similarity	NPD6013	Approved
0.6078	Remote Similarity	NPD5329	Approved
0.6068	Remote Similarity	NPD8297	Approved
0.6064	Remote Similarity	NPD4243	Approved
0.6061	Remote Similarity	NPD6930	Phase 2
0.6061	Remote Similarity	NPD4695	Discontinued
0.6061	Remote Similarity	NPD6931	Approved
0.6061	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5208	Approved
0.604	Remote Similarity	NPD5362	Discontinued
0.604	Remote Similarity	NPD7154	Phase 3
0.6038	Remote Similarity	NPD5694	Approved
0.602	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6098	Approved
0.6019	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4629	Approved
0.6019	Remote Similarity	NPD5210	Approved
0.6017	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD342	Phase 1
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5982	Remote Similarity	NPD5211	Phase 2
0.5981	Remote Similarity	NPD4202	Approved
0.598	Remote Similarity	NPD4197	Approved
0.5979	Remote Similarity	NPD6933	Approved
0.5968	Remote Similarity	NPD8328	Phase 3
0.5968	Remote Similarity	NPD6067	Discontinued
0.5963	Remote Similarity	NPD5221	Approved
0.5963	Remote Similarity	NPD5222	Approved
0.5963	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4697	Phase 3
0.5962	Remote Similarity	NPD3573	Approved
0.5952	Remote Similarity	NPD8293	Discontinued
0.5948	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5207	Approved
0.5941	Remote Similarity	NPD5209	Approved
0.5938	Remote Similarity	NPD4785	Approved
0.5938	Remote Similarity	NPD4784	Approved
0.5938	Remote Similarity	NPD6914	Discontinued
0.5922	Remote Similarity	NPD1696	Phase 3
0.5922	Remote Similarity	NPD5363	Approved
0.5922	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6925	Approved
0.5918	Remote Similarity	NPD5776	Phase 2
0.5917	Remote Similarity	NPD6868	Approved
0.5913	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4755	Approved
0.5909	Remote Similarity	NPD5173	Approved
0.5906	Remote Similarity	NPD7736	Approved
0.59	Remote Similarity	NPD7332	Phase 2
0.59	Remote Similarity	NPD4820	Approved
0.59	Remote Similarity	NPD4819	Approved
0.59	Remote Similarity	NPD4821	Approved
0.59	Remote Similarity	NPD4822	Approved
0.59	Remote Similarity	NPD7514	Phase 3
0.5897	Remote Similarity	NPD6371	Approved
0.5888	Remote Similarity	NPD8035	Phase 2
0.5888	Remote Similarity	NPD8034	Phase 2
0.5888	Remote Similarity	NPD7087	Discontinued
0.5887	Remote Similarity	NPD6370	Approved
0.5882	Remote Similarity	NPD5332	Approved
0.5882	Remote Similarity	NPD5331	Approved
0.5877	Remote Similarity	NPD5141	Approved
0.5868	Remote Similarity	NPD6317	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