NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	1.912
LogD:	2.291
LogS:	-2.973
# Rotatable Bonds:	0
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	4.246
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:	-4.879
MDCK Permeability:	1.2842716387240216e-05
Pgp-inhibitor:	0.115
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.25
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	83.25344848632812%
Volume Distribution (VD):	1.692
Pgp-substrate:	38.03235626220703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.822
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.488
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.576
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.591

ADMET: Excretion

Clearance (CL):	4.619
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.142
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.371
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.374
Carcinogencity:	0.799
Eye Corrosion:	0.004
Eye Irritation:	0.127
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC238582

Natural Product ID:	NPC238582
*Common Name:**	NOSCKDVJLGMLSG-GZBFAFLISA-N
IUPAC Name:	n.a.
Synonyms:	7,10-Dihydroxydehydrodihydrobotrydia
Standard InCHIKey:	NOSCKDVJLGMLSG-GZBFAFLISA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-5-6-9-11-10(8)12(16)18-7-15(11,4)13(17)14(9,2)3/h5-6,12-13,16-17H,7H2,1-4H3/t12-,13+,15+/m0/s1
SMILES:	O[C@H]1OC[C@@]2(c3c1c(C)ccc3C([C@H]2O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447574
PubChem CID:	11390996
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	isolated from the marine red alga Polysiphonia	n.a.	PMID[15787444]
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917307]

☑ 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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	0.0	mm	PMID[544900]
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	12.0	mm	PMID[544900]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	IZ	=	0.0	mm	PMID[544900]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	IZ	=	6.0	mm	PMID[544900]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	0.0	mm	PMID[544900]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	6.0	mm	PMID[544900]

☑ 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 NPC238582 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	265
0.1-0.2	1236
0.2-0.3	2612
0.3-0.4	7816
0.4-0.5	13538
0.5-0.6	13202
0.6-0.7	3847
0.7-0.8	172
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC146673
0.9735	High Similarity	NPC233923
0.9459	High Similarity	NPC169616
0.8346	Intermediate Similarity	NPC82712
0.8246	Intermediate Similarity	NPC471133
0.8214	Intermediate Similarity	NPC289117
0.8053	Intermediate Similarity	NPC245927
0.8	Intermediate Similarity	NPC315794
0.7951	Intermediate Similarity	NPC472862
0.7778	Intermediate Similarity	NPC152384
0.7778	Intermediate Similarity	NPC37714
0.7737	Intermediate Similarity	NPC164743
0.7731	Intermediate Similarity	NPC64642
0.7731	Intermediate Similarity	NPC472982
0.7731	Intermediate Similarity	NPC149455
0.7721	Intermediate Similarity	NPC156393
0.7672	Intermediate Similarity	NPC60373
0.7672	Intermediate Similarity	NPC154905
0.7615	Intermediate Similarity	NPC100402
0.7615	Intermediate Similarity	NPC9180
0.7612	Intermediate Similarity	NPC321086
0.7612	Intermediate Similarity	NPC51262
0.7607	Intermediate Similarity	NPC19856
0.7603	Intermediate Similarity	NPC264784
0.7603	Intermediate Similarity	NPC30563
0.7594	Intermediate Similarity	NPC72915
0.7557	Intermediate Similarity	NPC5486
0.7557	Intermediate Similarity	NPC321822
0.7557	Intermediate Similarity	NPC325294
0.7544	Intermediate Similarity	NPC21959
0.7542	Intermediate Similarity	NPC148060
0.7521	Intermediate Similarity	NPC474148
0.7521	Intermediate Similarity	NPC276061
0.75	Intermediate Similarity	NPC27252
0.75	Intermediate Similarity	NPC472979
0.75	Intermediate Similarity	NPC472980
0.75	Intermediate Similarity	NPC79917
0.7481	Intermediate Similarity	NPC124030
0.7481	Intermediate Similarity	NPC159811
0.7479	Intermediate Similarity	NPC243601
0.7463	Intermediate Similarity	NPC325003
0.7462	Intermediate Similarity	NPC470815
0.7462	Intermediate Similarity	NPC307139
0.7436	Intermediate Similarity	NPC469481
0.7434	Intermediate Similarity	NPC314690
0.7424	Intermediate Similarity	NPC253681
0.7424	Intermediate Similarity	NPC43000
0.7424	Intermediate Similarity	NPC472706
0.7424	Intermediate Similarity	NPC100414
0.7422	Intermediate Similarity	NPC68339
0.7419	Intermediate Similarity	NPC120217
0.7398	Intermediate Similarity	NPC111108
0.7395	Intermediate Similarity	NPC56168
0.7394	Intermediate Similarity	NPC96447
0.7385	Intermediate Similarity	NPC182333
0.7385	Intermediate Similarity	NPC273336
0.7368	Intermediate Similarity	NPC108164
0.7368	Intermediate Similarity	NPC230331
0.7364	Intermediate Similarity	NPC328504
0.7348	Intermediate Similarity	NPC470816
0.7348	Intermediate Similarity	NPC252962
0.7328	Intermediate Similarity	NPC77691
0.7323	Intermediate Similarity	NPC45794
0.7321	Intermediate Similarity	NPC1793
0.7313	Intermediate Similarity	NPC223912
0.731	Intermediate Similarity	NPC95990
0.7287	Intermediate Similarity	NPC133302
0.7286	Intermediate Similarity	NPC476643
0.7281	Intermediate Similarity	NPC128645
0.7279	Intermediate Similarity	NPC233692
0.7266	Intermediate Similarity	NPC164649
0.7266	Intermediate Similarity	NPC243893
0.7266	Intermediate Similarity	NPC262324
0.7266	Intermediate Similarity	NPC48342
0.7266	Intermediate Similarity	NPC254233
0.7265	Intermediate Similarity	NPC262826
0.7259	Intermediate Similarity	NPC25729
0.7259	Intermediate Similarity	NPC474494
0.7258	Intermediate Similarity	NPC471188
0.7246	Intermediate Similarity	NPC471864
0.7244	Intermediate Similarity	NPC175771
0.7244	Intermediate Similarity	NPC470820
0.7239	Intermediate Similarity	NPC186889
0.7239	Intermediate Similarity	NPC469386
0.7234	Intermediate Similarity	NPC221134
0.723	Intermediate Similarity	NPC469456
0.7222	Intermediate Similarity	NPC221275
0.7218	Intermediate Similarity	NPC293801
0.7209	Intermediate Similarity	NPC38181
0.7209	Intermediate Similarity	NPC20230
0.7206	Intermediate Similarity	NPC196193
0.7203	Intermediate Similarity	NPC471139
0.7197	Intermediate Similarity	NPC228739
0.7192	Intermediate Similarity	NPC476173
0.7188	Intermediate Similarity	NPC266389
0.7188	Intermediate Similarity	NPC216605
0.7188	Intermediate Similarity	NPC122245
0.7188	Intermediate Similarity	NPC476266
0.7176	Intermediate Similarity	NPC77569
0.7176	Intermediate Similarity	NPC142198
0.7174	Intermediate Similarity	NPC311492
0.7174	Intermediate Similarity	NPC28836
0.7164	Intermediate Similarity	NPC276047
0.7164	Intermediate Similarity	NPC267733
0.7163	Intermediate Similarity	NPC79921
0.7162	Intermediate Similarity	NPC77310
0.7154	Intermediate Similarity	NPC282255
0.7154	Intermediate Similarity	NPC133389
0.7154	Intermediate Similarity	NPC3239
0.7154	Intermediate Similarity	NPC234337
0.7154	Intermediate Similarity	NPC183339
0.7153	Intermediate Similarity	NPC78575
0.7153	Intermediate Similarity	NPC239358
0.7143	Intermediate Similarity	NPC176730
0.7143	Intermediate Similarity	NPC123175
0.7143	Intermediate Similarity	NPC145287
0.7132	Intermediate Similarity	NPC288290
0.7124	Intermediate Similarity	NPC130489
0.7124	Intermediate Similarity	NPC208676
0.7121	Intermediate Similarity	NPC472703
0.7121	Intermediate Similarity	NPC223351
0.7111	Intermediate Similarity	NPC471077
0.7109	Intermediate Similarity	NPC247858
0.7109	Intermediate Similarity	NPC148055
0.7109	Intermediate Similarity	NPC105141
0.7109	Intermediate Similarity	NPC137496
0.7109	Intermediate Similarity	NPC154511
0.7109	Intermediate Similarity	NPC474387
0.7109	Intermediate Similarity	NPC474358
0.7109	Intermediate Similarity	NPC257540
0.7109	Intermediate Similarity	NPC242764
0.7107	Intermediate Similarity	NPC47286
0.7101	Intermediate Similarity	NPC472248
0.7101	Intermediate Similarity	NPC59239
0.7092	Intermediate Similarity	NPC473301
0.709	Intermediate Similarity	NPC76119
0.709	Intermediate Similarity	NPC4286
0.7087	Intermediate Similarity	NPC306740
0.7087	Intermediate Similarity	NPC157338
0.7087	Intermediate Similarity	NPC313193
0.7086	Intermediate Similarity	NPC476784
0.708	Intermediate Similarity	NPC99795
0.7077	Intermediate Similarity	NPC470814
0.7071	Intermediate Similarity	NPC137580
0.7071	Intermediate Similarity	NPC202729
0.7068	Intermediate Similarity	NPC472704
0.7067	Intermediate Similarity	NPC257847
0.7067	Intermediate Similarity	NPC469699
0.7063	Intermediate Similarity	NPC137501
0.7063	Intermediate Similarity	NPC290353
0.7063	Intermediate Similarity	NPC153795
0.7063	Intermediate Similarity	NPC7518
0.7063	Intermediate Similarity	NPC42911
0.7063	Intermediate Similarity	NPC154262
0.7063	Intermediate Similarity	NPC159387
0.7054	Intermediate Similarity	NPC93843
0.7054	Intermediate Similarity	NPC243166
0.7054	Intermediate Similarity	NPC474211
0.705	Intermediate Similarity	NPC470143
0.705	Intermediate Similarity	NPC310662
0.705	Intermediate Similarity	NPC48929
0.705	Intermediate Similarity	NPC322503
0.7045	Intermediate Similarity	NPC293831
0.7045	Intermediate Similarity	NPC369
0.7045	Intermediate Similarity	NPC475328
0.704	Intermediate Similarity	NPC133308
0.7034	Intermediate Similarity	NPC251062
0.7034	Intermediate Similarity	NPC184464
0.7031	Intermediate Similarity	NPC469719
0.7031	Intermediate Similarity	NPC9274
0.7029	Intermediate Similarity	NPC233860
0.7029	Intermediate Similarity	NPC475824
0.7027	Intermediate Similarity	NPC304538
0.7025	Intermediate Similarity	NPC469527
0.7023	Intermediate Similarity	NPC282409
0.7023	Intermediate Similarity	NPC469702
0.7021	Intermediate Similarity	NPC475628
0.7021	Intermediate Similarity	NPC27721
0.7018	Intermediate Similarity	NPC199567
0.7016	Intermediate Similarity	NPC306295
0.7007	Intermediate Similarity	NPC474564
0.7007	Intermediate Similarity	NPC27712
0.7007	Intermediate Similarity	NPC49272
0.7	Intermediate Similarity	NPC154030
0.7	Intermediate Similarity	NPC200154
0.7	Intermediate Similarity	NPC471671
0.6993	Remote Similarity	NPC242355
0.6992	Remote Similarity	NPC474376
0.6992	Remote Similarity	NPC152946
0.6992	Remote Similarity	NPC472316
0.6992	Remote Similarity	NPC475203
0.6992	Remote Similarity	NPC57199
0.6992	Remote Similarity	NPC136962
0.6992	Remote Similarity	NPC472315
0.6992	Remote Similarity	NPC476142
0.6986	Remote Similarity	NPC478263
0.6985	Remote Similarity	NPC472707
0.6985	Remote Similarity	NPC175333
0.698	Remote Similarity	NPC183380
0.6978	Remote Similarity	NPC85595

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 NPC238582 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	851
0.2-0.3	1520
0.3-0.4	3057
0.4-0.5	2152
0.5-0.6	1129
0.6-0.7	186
0.7-0.8	4
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8279	Intermediate Similarity	NPD5125	Phase 3
0.8279	Intermediate Similarity	NPD5126	Approved
0.8264	Intermediate Similarity	NPD7741	Discontinued
0.7311	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3091	Approved
0.7176	Intermediate Similarity	NPD3092	Approved
0.7132	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4140	Approved
0.709	Intermediate Similarity	NPD3094	Phase 2
0.705	Intermediate Similarity	NPD5735	Approved
0.7023	Intermediate Similarity	NPD3095	Discontinued
0.6985	Remote Similarity	NPD5736	Approved
0.6977	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5327	Phase 3
0.6923	Remote Similarity	NPD5763	Approved
0.6923	Remote Similarity	NPD5762	Approved
0.6917	Remote Similarity	NPD1091	Approved
0.6912	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4624	Approved
0.6912	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4198	Discontinued
0.6879	Remote Similarity	NPD6353	Approved
0.6857	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3620	Phase 2
0.6855	Remote Similarity	NPD6685	Approved
0.6835	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD41	Approved
0.6831	Remote Similarity	NPD5886	Approved
0.6806	Remote Similarity	NPD6004	Phase 3
0.6806	Remote Similarity	NPD6002	Phase 3
0.6806	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6005	Phase 3
0.6806	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6085	Phase 2
0.6786	Remote Similarity	NPD6663	Approved
0.6767	Remote Similarity	NPD4059	Approved
0.6765	Remote Similarity	NPD6696	Suspended
0.6763	Remote Similarity	NPD7008	Discontinued
0.6763	Remote Similarity	NPD4625	Phase 3
0.6744	Remote Similarity	NPD6010	Discontinued
0.6744	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6674	Discontinued
0.6692	Remote Similarity	NPD2629	Approved
0.6689	Remote Similarity	NPD7236	Approved
0.6646	Remote Similarity	NPD7799	Discontinued
0.6642	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD2861	Phase 2
0.6613	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5765	Approved
0.6599	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD969	Suspended
0.6579	Remote Similarity	NPD7239	Suspended
0.6575	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD1357	Approved
0.6565	Remote Similarity	NPD5951	Approved
0.656	Remote Similarity	NPD3047	Approved
0.656	Remote Similarity	NPD3048	Approved
0.656	Remote Similarity	NPD3046	Approved
0.6519	Remote Similarity	NPD4626	Approved
0.6512	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6912	Phase 3
0.6449	Remote Similarity	NPD4749	Approved
0.6447	Remote Similarity	NPD6273	Approved
0.6446	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1710	Approved
0.6444	Remote Similarity	NPD5691	Approved
0.6441	Remote Similarity	NPD689	Discontinued
0.6438	Remote Similarity	NPD4108	Discontinued
0.6429	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5618	Discontinued
0.6423	Remote Similarity	NPD1610	Phase 2
0.6423	Remote Similarity	NPD3705	Approved
0.6414	Remote Similarity	NPD4097	Suspended
0.6412	Remote Similarity	NPD6858	Approved
0.6412	Remote Similarity	NPD1138	Approved
0.6412	Remote Similarity	NPD7635	Approved
0.6412	Remote Similarity	NPD7094	Approved
0.6406	Remote Similarity	NPD6406	Approved
0.6403	Remote Similarity	NPD8651	Approved
0.6397	Remote Similarity	NPD3019	Approved
0.6397	Remote Similarity	NPD2932	Approved
0.6397	Remote Similarity	NPD7725	Approved
0.6397	Remote Similarity	NPD1778	Approved
0.6396	Remote Similarity	NPD9294	Approved
0.6393	Remote Similarity	NPD1809	Phase 2
0.6391	Remote Similarity	NPD7157	Approved
0.6378	Remote Similarity	NPD5048	Discontinued
0.637	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD845	Approved
0.6364	Remote Similarity	NPD1398	Phase 1
0.6358	Remote Similarity	NPD5058	Phase 3
0.6351	Remote Similarity	NPD7266	Discontinued
0.635	Remote Similarity	NPD3897	Approved
0.635	Remote Similarity	NPD3896	Approved
0.635	Remote Similarity	NPD3898	Approved
0.635	Remote Similarity	NPD3895	Approved
0.6338	Remote Similarity	NPD4908	Phase 1
0.6336	Remote Similarity	NPD1137	Approved
0.6336	Remote Similarity	NPD1139	Approved
0.6333	Remote Similarity	NPD4628	Phase 3
0.6327	Remote Similarity	NPD7743	Approved
0.6327	Remote Similarity	NPD7305	Phase 1
0.6327	Remote Similarity	NPD7742	Approved
0.632	Remote Similarity	NPD2553	Approved
0.632	Remote Similarity	NPD2550	Approved
0.632	Remote Similarity	NPD2549	Approved
0.632	Remote Similarity	NPD2558	Approved
0.632	Remote Similarity	NPD2555	Approved
0.632	Remote Similarity	NPD2552	Approved
0.6319	Remote Similarity	NPD4404	Approved
0.6308	Remote Similarity	NPD4750	Phase 3
0.6301	Remote Similarity	NPD6653	Approved
0.6299	Remote Similarity	NPD5699	Approved
0.6286	Remote Similarity	NPD1283	Approved
0.6279	Remote Similarity	NPD2342	Discontinued
0.6279	Remote Similarity	NPD290	Approved
0.6277	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.627	Remote Similarity	NPD4189	Approved
0.627	Remote Similarity	NPD4188	Approved
0.626	Remote Similarity	NPD844	Approved
0.625	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD6362	Approved
0.624	Remote Similarity	NPD3020	Approved
0.6233	Remote Similarity	NPD5124	Phase 1
0.6233	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD3657	Discovery
0.6231	Remote Similarity	NPD4718	Approved
0.6231	Remote Similarity	NPD4720	Approved
0.6231	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD4717	Approved
0.6231	Remote Similarity	NPD2684	Approved
0.6225	Remote Similarity	NPD3892	Phase 2
0.6225	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7340	Approved
0.622	Remote Similarity	NPD6647	Phase 2
0.6218	Remote Similarity	NPD531	Approved
0.6216	Remote Similarity	NPD7033	Discontinued
0.6214	Remote Similarity	NPD6025	Phase 1
0.6214	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.621	Remote Similarity	NPD288	Approved
0.6204	Remote Similarity	NPD1651	Approved
0.6203	Remote Similarity	NPD37	Approved
0.6202	Remote Similarity	NPD3526	Approved
0.6202	Remote Similarity	NPD3524	Approved
0.619	Remote Similarity	NPD289	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2157	Approved
0.619	Remote Similarity	NPD1616	Discontinued
0.6188	Remote Similarity	NPD7057	Phase 3
0.6188	Remote Similarity	NPD4967	Phase 2
0.6188	Remote Similarity	NPD4966	Approved
0.6188	Remote Similarity	NPD7058	Phase 2
0.6188	Remote Similarity	NPD4965	Approved
0.6181	Remote Similarity	NPD3027	Phase 3
0.6179	Remote Similarity	NPD1693	Approved
0.6179	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6049	Phase 2
0.6178	Remote Similarity	NPD7028	Phase 2
0.6174	Remote Similarity	NPD6100	Approved
0.6174	Remote Similarity	NPD7137	Phase 2
0.6174	Remote Similarity	NPD6099	Approved
0.6169	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD2238	Phase 2
0.6164	Remote Similarity	NPD4060	Phase 1
0.6164	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.616	Remote Similarity	NPD9495	Approved
0.6154	Remote Similarity	NPD9532	Phase 3
0.6149	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD4536	Approved
0.6149	Remote Similarity	NPD4538	Approved
0.6148	Remote Similarity	NPD709	Approved
0.6148	Remote Similarity	NPD6671	Approved
0.6148	Remote Similarity	NPD1088	Approved
0.6143	Remote Similarity	NPD7250	Approved
0.6143	Remote Similarity	NPD7249	Approved
0.6142	Remote Similarity	NPD940	Approved
0.6142	Remote Similarity	NPD846	Approved
0.6136	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD1548	Phase 1
0.6131	Remote Similarity	NPD4479	Discontinued
0.6129	Remote Similarity	NPD2859	Approved
0.6129	Remote Similarity	NPD2860	Approved
0.6119	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD5588	Approved
0.6107	Remote Similarity	NPD2182	Approved
0.6103	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD3685	Discontinued
0.6096	Remote Similarity	NPD8032	Phase 2
0.6094	Remote Similarity	NPD3683	Approved
0.6094	Remote Similarity	NPD3681	Approved
0.609	Remote Similarity	NPD4573	Approved
0.609	Remote Similarity	NPD4572	Approved
0.609	Remote Similarity	NPD4571	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