NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.17
Volume:	295.38
LogP:	2.723
LogD:	2.945
LogS:	-3.477
# Rotatable Bonds:	2
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.902
Synthetic Accessibility Score:	4.213
Fsp3:	0.647
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:	-4.706
MDCK Permeability:	1.961742964340374e-05
Pgp-inhibitor:	0.931
Pgp-substrate:	0.588
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	88.8899154663086%
Volume Distribution (VD):	1.779
Pgp-substrate:	21.462888717651367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.277
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.259
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.502
CYP3A4-inhibitor:	0.094
CYP3A4-substrate:	0.634

ADMET: Excretion

Clearance (CL):	5.879
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.365
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.322
Carcinogencity:	0.696
Eye Corrosion:	0.005
Eye Irritation:	0.114
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC146673

Natural Product ID:	NPC146673
*Common Name:**	WVMUFKGZUAMWJW-ZMSDIMECSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WVMUFKGZUAMWJW-ZMSDIMECSA-N
Standard InCHI:	InChI=1S/C17H24O3/c1-6-19-14-12-10(2)7-8-11-13(12)17(5,9-20-14)15(18)16(11,3)4/h7-8,14-15,18H,6,9H2,1-5H3/t14-,15+,17+/m0/s1
SMILES:	CCO[C@H]1OC[C@@]2(c3c1c(C)ccc3C([C@H]2O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480077
PubChem CID:	11265857
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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	5.0	mm	PMID[567531]
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	6.0	mm	PMID[567531]

☑ 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 NPC146673 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	271
0.1-0.2	1249
0.2-0.3	2614
0.3-0.4	7966
0.4-0.5	13838
0.5-0.6	13061
0.6-0.7	3545
0.7-0.8	145
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233923
0.9735	High Similarity	NPC238582
0.9375	High Similarity	NPC169616
0.8281	Intermediate Similarity	NPC82712
0.8174	Intermediate Similarity	NPC471133
0.8142	Intermediate Similarity	NPC245927
0.7982	Intermediate Similarity	NPC289117
0.7886	Intermediate Similarity	NPC472862
0.7863	Intermediate Similarity	NPC152384
0.7863	Intermediate Similarity	NPC37714
0.7833	Intermediate Similarity	NPC264784
0.7833	Intermediate Similarity	NPC30563
0.7829	Intermediate Similarity	NPC9180
0.7829	Intermediate Similarity	NPC100402
0.781	Intermediate Similarity	NPC164743
0.7794	Intermediate Similarity	NPC156393
0.7778	Intermediate Similarity	NPC315794
0.775	Intermediate Similarity	NPC276061
0.775	Intermediate Similarity	NPC474148
0.7687	Intermediate Similarity	NPC159811
0.7687	Intermediate Similarity	NPC321086
0.7669	Intermediate Similarity	NPC72915
0.7667	Intermediate Similarity	NPC149455
0.7667	Intermediate Similarity	NPC472982
0.7667	Intermediate Similarity	NPC64642
0.7627	Intermediate Similarity	NPC148060
0.7607	Intermediate Similarity	NPC60373
0.7607	Intermediate Similarity	NPC154905
0.7542	Intermediate Similarity	NPC19856
0.7538	Intermediate Similarity	NPC470815
0.7538	Intermediate Similarity	NPC307139
0.75	Intermediate Similarity	NPC43000
0.75	Intermediate Similarity	NPC325294
0.75	Intermediate Similarity	NPC120217
0.75	Intermediate Similarity	NPC321822
0.75	Intermediate Similarity	NPC95990
0.75	Intermediate Similarity	NPC100414
0.75	Intermediate Similarity	NPC472706
0.75	Intermediate Similarity	NPC5486
0.7479	Intermediate Similarity	NPC56168
0.7465	Intermediate Similarity	NPC96447
0.7444	Intermediate Similarity	NPC230331
0.7444	Intermediate Similarity	NPC108164
0.7438	Intermediate Similarity	NPC472980
0.7438	Intermediate Similarity	NPC27252
0.7438	Intermediate Similarity	NPC472979
0.7426	Intermediate Similarity	NPC51262
0.7424	Intermediate Similarity	NPC470816
0.7424	Intermediate Similarity	NPC124030
0.7417	Intermediate Similarity	NPC243601
0.7415	Intermediate Similarity	NPC469456
0.7407	Intermediate Similarity	NPC325003
0.7402	Intermediate Similarity	NPC216605
0.7402	Intermediate Similarity	NPC266389
0.7402	Intermediate Similarity	NPC122245
0.7402	Intermediate Similarity	NPC45794
0.7394	Intermediate Similarity	NPC471139
0.7388	Intermediate Similarity	NPC223912
0.7379	Intermediate Similarity	NPC476173
0.7373	Intermediate Similarity	NPC469481
0.7368	Intermediate Similarity	NPC253681
0.7364	Intermediate Similarity	NPC68339
0.7357	Intermediate Similarity	NPC476643
0.735	Intermediate Similarity	NPC262826
0.7348	Intermediate Similarity	NPC145287
0.7344	Intermediate Similarity	NPC254233
0.7333	Intermediate Similarity	NPC47286
0.7328	Intermediate Similarity	NPC273336
0.7328	Intermediate Similarity	NPC21959
0.7328	Intermediate Similarity	NPC182333
0.7313	Intermediate Similarity	NPC186889
0.7308	Intermediate Similarity	NPC328504
0.7302	Intermediate Similarity	NPC221275
0.7287	Intermediate Similarity	NPC20230
0.7287	Intermediate Similarity	NPC38181
0.7287	Intermediate Similarity	NPC470814
0.7281	Intermediate Similarity	NPC79917
0.7273	Intermediate Similarity	NPC77691
0.7267	Intermediate Similarity	NPC476784
0.725	Intermediate Similarity	NPC469527
0.7248	Intermediate Similarity	NPC469699
0.7239	Intermediate Similarity	NPC267733
0.7239	Intermediate Similarity	NPC276047
0.723	Intermediate Similarity	NPC77310
0.7226	Intermediate Similarity	NPC233692
0.7226	Intermediate Similarity	NPC239358
0.7217	Intermediate Similarity	NPC314690
0.7214	Intermediate Similarity	NPC262324
0.7214	Intermediate Similarity	NPC243893
0.7209	Intermediate Similarity	NPC164649
0.7209	Intermediate Similarity	NPC48342
0.7206	Intermediate Similarity	NPC25729
0.7206	Intermediate Similarity	NPC474494
0.7206	Intermediate Similarity	NPC27712
0.72	Intermediate Similarity	NPC471188
0.72	Intermediate Similarity	NPC111108
0.7197	Intermediate Similarity	NPC476142
0.7197	Intermediate Similarity	NPC472703
0.7194	Intermediate Similarity	NPC471864
0.7192	Intermediate Similarity	NPC474564
0.719	Intermediate Similarity	NPC208676
0.719	Intermediate Similarity	NPC130489
0.7188	Intermediate Similarity	NPC148055
0.7188	Intermediate Similarity	NPC470820
0.7188	Intermediate Similarity	NPC175771
0.7185	Intermediate Similarity	NPC175333
0.7183	Intermediate Similarity	NPC221134
0.7176	Intermediate Similarity	NPC229600
0.7174	Intermediate Similarity	NPC472248
0.7174	Intermediate Similarity	NPC476644
0.7164	Intermediate Similarity	NPC252962
0.7153	Intermediate Similarity	NPC196193
0.7143	Intermediate Similarity	NPC472704
0.7143	Intermediate Similarity	NPC475561
0.7143	Intermediate Similarity	NPC137580
0.7143	Intermediate Similarity	NPC475447
0.7143	Intermediate Similarity	NPC475218
0.7143	Intermediate Similarity	NPC476092
0.7143	Intermediate Similarity	NPC70236
0.7143	Intermediate Similarity	NPC475417
0.7133	Intermediate Similarity	NPC137501
0.7133	Intermediate Similarity	NPC154262
0.7133	Intermediate Similarity	NPC257847
0.7133	Intermediate Similarity	NPC7518
0.7133	Intermediate Similarity	NPC159387
0.7132	Intermediate Similarity	NPC476266
0.7122	Intermediate Similarity	NPC470143
0.7122	Intermediate Similarity	NPC28836
0.7122	Intermediate Similarity	NPC311492
0.7122	Intermediate Similarity	NPC48929
0.7122	Intermediate Similarity	NPC322503
0.7121	Intermediate Similarity	NPC77569
0.7121	Intermediate Similarity	NPC142198
0.7114	Intermediate Similarity	NPC472658
0.7114	Intermediate Similarity	NPC472657
0.7113	Intermediate Similarity	NPC79921
0.7109	Intermediate Similarity	NPC9274
0.7105	Intermediate Similarity	NPC1793
0.7103	Intermediate Similarity	NPC184464
0.7103	Intermediate Similarity	NPC251062
0.7101	Intermediate Similarity	NPC233860
0.7101	Intermediate Similarity	NPC78575
0.7101	Intermediate Similarity	NPC475824
0.7099	Intermediate Similarity	NPC133302
0.7099	Intermediate Similarity	NPC234337
0.7099	Intermediate Similarity	NPC133389
0.7099	Intermediate Similarity	NPC469702
0.7099	Intermediate Similarity	NPC183339
0.7099	Intermediate Similarity	NPC282255
0.7099	Intermediate Similarity	NPC282409
0.7095	Intermediate Similarity	NPC298072
0.7095	Intermediate Similarity	NPC478123
0.7095	Intermediate Similarity	NPC62792
0.7092	Intermediate Similarity	NPC475628
0.709	Intermediate Similarity	NPC57607
0.7087	Intermediate Similarity	NPC123175
0.7087	Intermediate Similarity	NPC176730
0.708	Intermediate Similarity	NPC288290
0.7071	Intermediate Similarity	NPC200154
0.7071	Intermediate Similarity	NPC473399
0.7071	Intermediate Similarity	NPC473216
0.7069	Intermediate Similarity	NPC128645
0.7068	Intermediate Similarity	NPC152946
0.7063	Intermediate Similarity	NPC471862
0.7059	Intermediate Similarity	NPC469386
0.7059	Intermediate Similarity	NPC472707
0.7059	Intermediate Similarity	NPC471077
0.7055	Intermediate Similarity	NPC478263
0.7054	Intermediate Similarity	NPC474387
0.7054	Intermediate Similarity	NPC474358
0.7054	Intermediate Similarity	NPC257540
0.7054	Intermediate Similarity	NPC105141
0.7054	Intermediate Similarity	NPC247858
0.7054	Intermediate Similarity	NPC137496
0.7054	Intermediate Similarity	NPC242764
0.7054	Intermediate Similarity	NPC154511
0.705	Intermediate Similarity	NPC59239
0.7047	Intermediate Similarity	NPC183380
0.7045	Intermediate Similarity	NPC476448
0.7045	Intermediate Similarity	NPC469412
0.7045	Intermediate Similarity	NPC198734
0.7045	Intermediate Similarity	NPC469548
0.7045	Intermediate Similarity	NPC476445
0.7042	Intermediate Similarity	NPC473301
0.7037	Intermediate Similarity	NPC293801
0.7037	Intermediate Similarity	NPC4286
0.7037	Intermediate Similarity	NPC76119
0.7034	Intermediate Similarity	NPC204644
0.7034	Intermediate Similarity	NPC186296
0.7031	Intermediate Similarity	NPC157338
0.7031	Intermediate Similarity	NPC313193
0.7029	Intermediate Similarity	NPC99795
0.7027	Intermediate Similarity	NPC222102
0.7027	Intermediate Similarity	NPC303429
0.7027	Intermediate Similarity	NPC469448
0.7023	Intermediate Similarity	NPC14950
0.7021	Intermediate Similarity	NPC79957
0.7021	Intermediate Similarity	NPC202729
0.7015	Intermediate Similarity	NPC138798
0.7015	Intermediate Similarity	NPC228739

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 NPC146673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	858
0.2-0.3	1535
0.3-0.4	3096
0.4-0.5	2143
0.5-0.6	1096
0.6-0.7	166
0.7-0.8	3
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
0.8512	High Similarity	NPD5126	Approved
0.8512	High Similarity	NPD5125	Phase 3
0.8197	Intermediate Similarity	NPD7741	Discontinued
0.725	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3091	Approved
0.7206	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4140	Approved
0.7122	Intermediate Similarity	NPD5735	Approved
0.7121	Intermediate Similarity	NPD3092	Approved
0.7099	Intermediate Similarity	NPD3095	Discontinued
0.7054	Intermediate Similarity	NPD4230	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3094	Phase 2
0.7015	Intermediate Similarity	NPD5327	Phase 3
0.6993	Remote Similarity	NPD5763	Approved
0.6993	Remote Similarity	NPD5762	Approved
0.6985	Remote Similarity	NPD4624	Approved
0.6977	Remote Similarity	NPD4198	Discontinued
0.695	Remote Similarity	NPD6353	Approved
0.6935	Remote Similarity	NPD6685	Approved
0.6934	Remote Similarity	NPD5736	Approved
0.6901	Remote Similarity	NPD41	Approved
0.6901	Remote Similarity	NPD5886	Approved
0.6897	Remote Similarity	NPD6674	Discontinued
0.6866	Remote Similarity	NPD1091	Approved
0.6861	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6010	Discontinued
0.6813	Remote Similarity	NPD7799	Discontinued
0.6809	Remote Similarity	NPD3620	Phase 2
0.6809	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6002	Phase 3
0.6759	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6004	Phase 3
0.6759	Remote Similarity	NPD6005	Phase 3
0.6757	Remote Similarity	NPD7236	Approved
0.6739	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6085	Phase 2
0.6738	Remote Similarity	NPD6663	Approved
0.6716	Remote Similarity	NPD4059	Approved
0.6716	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6696	Suspended
0.6714	Remote Similarity	NPD7008	Discontinued
0.6714	Remote Similarity	NPD4625	Phase 3
0.6694	Remote Similarity	NPD5765	Approved
0.6692	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD969	Suspended
0.6645	Remote Similarity	NPD7239	Suspended
0.6641	Remote Similarity	NPD2629	Approved
0.664	Remote Similarity	NPD3047	Approved
0.664	Remote Similarity	NPD3048	Approved
0.664	Remote Similarity	NPD3046	Approved
0.6621	Remote Similarity	NPD4108	Discontinued
0.6618	Remote Similarity	NPD3705	Approved
0.6589	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2861	Phase 2
0.6567	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6912	Phase 3
0.6533	Remote Similarity	NPD5058	Phase 3
0.6531	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5691	Approved
0.6519	Remote Similarity	NPD1357	Approved
0.6515	Remote Similarity	NPD5951	Approved
0.6513	Remote Similarity	NPD6273	Approved
0.6496	Remote Similarity	NPD5618	Discontinued
0.6489	Remote Similarity	NPD6858	Approved
0.6489	Remote Similarity	NPD7094	Approved
0.6475	Remote Similarity	NPD8651	Approved
0.6471	Remote Similarity	NPD4626	Approved
0.6466	Remote Similarity	NPD7157	Approved
0.6447	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD3898	Approved
0.6423	Remote Similarity	NPD3897	Approved
0.6423	Remote Similarity	NPD3896	Approved
0.6423	Remote Similarity	NPD3895	Approved
0.6419	Remote Similarity	NPD7266	Discontinued
0.6403	Remote Similarity	NPD4749	Approved
0.64	Remote Similarity	NPD2558	Approved
0.64	Remote Similarity	NPD2553	Approved
0.64	Remote Similarity	NPD2550	Approved
0.64	Remote Similarity	NPD2555	Approved
0.64	Remote Similarity	NPD2549	Approved
0.64	Remote Similarity	NPD2552	Approved
0.6389	Remote Similarity	NPD4404	Approved
0.6387	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.637	Remote Similarity	NPD4097	Suspended
0.6364	Remote Similarity	NPD1138	Approved
0.6364	Remote Similarity	NPD7635	Approved
0.6364	Remote Similarity	NPD5699	Approved
0.6357	Remote Similarity	NPD6406	Approved
0.635	Remote Similarity	NPD3019	Approved
0.635	Remote Similarity	NPD2932	Approved
0.635	Remote Similarity	NPD1778	Approved
0.635	Remote Similarity	NPD7725	Approved
0.6349	Remote Similarity	NPD4189	Approved
0.6349	Remote Similarity	NPD4188	Approved
0.6346	Remote Similarity	NPD7028	Phase 2
0.6345	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.634	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5048	Discontinued
0.6312	Remote Similarity	NPD6362	Approved
0.6308	Remote Similarity	NPD2684	Approved
0.6301	Remote Similarity	NPD3657	Discovery
0.6294	Remote Similarity	NPD4908	Phase 1
0.6291	Remote Similarity	NPD4628	Phase 3
0.6291	Remote Similarity	NPD3892	Phase 2
0.6291	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD1137	Approved
0.6288	Remote Similarity	NPD1139	Approved
0.6286	Remote Similarity	NPD6025	Phase 1
0.6284	Remote Similarity	NPD7742	Approved
0.6284	Remote Similarity	NPD7743	Approved
0.6284	Remote Similarity	NPD7305	Phase 1
0.6279	Remote Similarity	NPD3526	Approved
0.6279	Remote Similarity	NPD3524	Approved
0.6277	Remote Similarity	NPD1710	Approved
0.6266	Remote Similarity	NPD37	Approved
0.626	Remote Similarity	NPD4750	Phase 3
0.626	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD1610	Phase 2
0.6259	Remote Similarity	NPD2157	Approved
0.6259	Remote Similarity	NPD6653	Approved
0.625	Remote Similarity	NPD7057	Phase 3
0.625	Remote Similarity	NPD7058	Phase 2
0.625	Remote Similarity	NPD689	Discontinued
0.625	Remote Similarity	NPD4965	Approved
0.625	Remote Similarity	NPD4966	Approved
0.625	Remote Similarity	NPD4967	Phase 2
0.6241	Remote Similarity	NPD1283	Approved
0.6232	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD2342	Discontinued
0.6231	Remote Similarity	NPD290	Approved
0.6226	Remote Similarity	NPD8455	Phase 2
0.6216	Remote Similarity	NPD4536	Approved
0.6216	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4538	Approved
0.6212	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.621	Remote Similarity	NPD1809	Phase 2
0.6207	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4479	Discontinued
0.6196	Remote Similarity	NPD7199	Phase 2
0.6195	Remote Similarity	NPD9294	Approved
0.6194	Remote Similarity	NPD1398	Phase 1
0.619	Remote Similarity	NPD3020	Approved
0.619	Remote Similarity	NPD5124	Phase 1
0.619	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD2182	Approved
0.6183	Remote Similarity	NPD4718	Approved
0.6183	Remote Similarity	NPD4720	Approved
0.6183	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD4717	Approved
0.6179	Remote Similarity	NPD845	Approved
0.6176	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7340	Approved
0.6174	Remote Similarity	NPD5588	Approved
0.6174	Remote Similarity	NPD7033	Discontinued
0.6172	Remote Similarity	NPD6647	Phase 2
0.617	Remote Similarity	NPD3685	Discontinued
0.617	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD531	Approved
0.6165	Remote Similarity	NPD4571	Approved
0.6165	Remote Similarity	NPD4572	Approved
0.6165	Remote Similarity	NPD4573	Approved
0.6164	Remote Similarity	NPD8032	Phase 2
0.6159	Remote Similarity	NPD1651	Approved
0.6159	Remote Similarity	NPD7503	Approved
0.6154	Remote Similarity	NPD2551	Approved
0.6154	Remote Similarity	NPD2559	Approved
0.6138	Remote Similarity	NPD3027	Phase 3
0.6133	Remote Similarity	NPD7137	Phase 2
0.6133	Remote Similarity	NPD6100	Approved
0.6133	Remote Similarity	NPD6099	Approved
0.6129	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6049	Phase 2
0.6129	Remote Similarity	NPD1693	Approved
0.6122	Remote Similarity	NPD2238	Phase 2
0.6122	Remote Similarity	NPD4060	Phase 1
0.6119	Remote Similarity	NPD7843	Approved
0.6108	Remote Similarity	NPD7228	Approved
0.6103	Remote Similarity	NPD6387	Discontinued
0.6103	Remote Similarity	NPD709	Approved
0.6103	Remote Similarity	NPD6671	Approved
0.6099	Remote Similarity	NPD7249	Approved
0.6099	Remote Similarity	NPD7250	Approved
0.6098	Remote Similarity	NPD1088	Approved
0.6096	Remote Similarity	NPD7294	Phase 1
0.6094	Remote Similarity	NPD4719	Phase 2
0.609	Remote Similarity	NPD2201	Approved
0.6087	Remote Similarity	NPD7009	Phase 2
0.608	Remote Similarity	NPD1989	Approved
0.608	Remote Similarity	NPD2859	Approved
0.608	Remote Similarity	NPD2860	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