NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.16
Volume:	278.084
LogP:	2.661
LogD:	2.515
LogS:	-4.429
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	5.02
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.705
MDCK Permeability:	4.3129290133947507e-05
Pgp-inhibitor:	0.507
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	54.28852844238281%
Volume Distribution (VD):	0.688
Pgp-substrate:	61.83037567138672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.651
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.358
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.533
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	8.958
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.344
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.798
Maximum Recommended Daily Dose:	0.471
Skin Sensitization:	0.808
Carcinogencity:	0.831
Eye Corrosion:	0.708
Eye Irritation:	0.338
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC475932

Natural Product ID:	NPC475932
*Common Name:**	GSIXJGGFGLGVPF-BUWBCJGYSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Terrecyclic Acid A Methyl Ester
Standard InCHIKey:	GSIXJGGFGLGVPF-BUWBCJGYSA-N
Standard InCHI:	InChI=1S/C16H22O3/c1-9-13(17)7-12-10-5-6-11(14(18)19-4)16(9,12)8-15(10,2)3/h10-12H,1,5-8H2,2-4H3/t10-,11+,12-,16-/m0/s1
SMILES:	CC1(CC23C(CCC1C2CC(=O)C3=C)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518807
PubChem CID:	23247890
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	from the rhizosphere of Opuntia versicolor of the Sonoran Desert	n.a.	PMID[14695798]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124769]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271552]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22360613]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24534845]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25671343]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2921224]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30207465]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32163285]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32897070]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984154]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	9400.0	nM	PMID[503981]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16700.0	nM	PMID[503981]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	10200.0	nM	PMID[503981]

☑ 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 NPC475932 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	204
0.1-0.2	2097
0.2-0.3	12156
0.3-0.4	12161
0.4-0.5	7357
0.5-0.6	6231
0.6-0.7	2305
0.7-0.8	180
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC74685
0.8228	Intermediate Similarity	NPC471475
0.8101	Intermediate Similarity	NPC63020
0.8072	Intermediate Similarity	NPC142649
0.8049	Intermediate Similarity	NPC271784
0.8	Intermediate Similarity	NPC118987
0.7975	Intermediate Similarity	NPC212661
0.7975	Intermediate Similarity	NPC471035
0.7952	Intermediate Similarity	NPC320801
0.7952	Intermediate Similarity	NPC238197
0.7927	Intermediate Similarity	NPC258153
0.7927	Intermediate Similarity	NPC476458
0.7927	Intermediate Similarity	NPC100297
0.7922	Intermediate Similarity	NPC248567
0.7922	Intermediate Similarity	NPC279241
0.7901	Intermediate Similarity	NPC170038
0.7887	Intermediate Similarity	NPC270042
0.7831	Intermediate Similarity	NPC469561
0.7778	Intermediate Similarity	NPC28319
0.7765	Intermediate Similarity	NPC6247
0.7765	Intermediate Similarity	NPC471042
0.7753	Intermediate Similarity	NPC56525
0.775	Intermediate Similarity	NPC169389
0.7711	Intermediate Similarity	NPC327969
0.7711	Intermediate Similarity	NPC240302
0.7711	Intermediate Similarity	NPC321289
0.7701	Intermediate Similarity	NPC11611
0.7701	Intermediate Similarity	NPC473039
0.7692	Intermediate Similarity	NPC52667
0.7692	Intermediate Similarity	NPC177826
0.7647	Intermediate Similarity	NPC470223
0.7647	Intermediate Similarity	NPC473038
0.7625	Intermediate Similarity	NPC20466
0.7619	Intermediate Similarity	NPC472740
0.7595	Intermediate Similarity	NPC475517
0.7595	Intermediate Similarity	NPC474524
0.759	Intermediate Similarity	NPC477372
0.759	Intermediate Similarity	NPC232625
0.7586	Intermediate Similarity	NPC56413
0.7561	Intermediate Similarity	NPC192744
0.7561	Intermediate Similarity	NPC477371
0.7531	Intermediate Similarity	NPC238227
0.7531	Intermediate Similarity	NPC472300
0.7531	Intermediate Similarity	NPC66105
0.7531	Intermediate Similarity	NPC106078
0.7529	Intermediate Similarity	NPC149869
0.7529	Intermediate Similarity	NPC109512
0.7529	Intermediate Similarity	NPC475100
0.7529	Intermediate Similarity	NPC100391
0.7528	Intermediate Similarity	NPC218301
0.75	Intermediate Similarity	NPC132064
0.75	Intermediate Similarity	NPC469868
0.7468	Intermediate Similarity	NPC330659
0.7468	Intermediate Similarity	NPC161187
0.7468	Intermediate Similarity	NPC244708
0.7444	Intermediate Similarity	NPC475700
0.7442	Intermediate Similarity	NPC94531
0.7442	Intermediate Similarity	NPC311702
0.7442	Intermediate Similarity	NPC323765
0.7442	Intermediate Similarity	NPC123319
0.7442	Intermediate Similarity	NPC29447
0.7439	Intermediate Similarity	NPC321690
0.7439	Intermediate Similarity	NPC469996
0.7439	Intermediate Similarity	NPC476810
0.7412	Intermediate Similarity	NPC65350
0.7407	Intermediate Similarity	NPC246445
0.7391	Intermediate Similarity	NPC470387
0.7386	Intermediate Similarity	NPC28227
0.7381	Intermediate Similarity	NPC38350
0.7381	Intermediate Similarity	NPC147066
0.7381	Intermediate Similarity	NPC201912
0.7363	Intermediate Similarity	NPC41649
0.7356	Intermediate Similarity	NPC80590
0.7356	Intermediate Similarity	NPC195640
0.7349	Intermediate Similarity	NPC263951
0.7333	Intermediate Similarity	NPC470230
0.7333	Intermediate Similarity	NPC250753
0.7326	Intermediate Similarity	NPC219011
0.7326	Intermediate Similarity	NPC475509
0.7326	Intermediate Similarity	NPC209882
0.7317	Intermediate Similarity	NPC68828
0.7312	Intermediate Similarity	NPC226986
0.7312	Intermediate Similarity	NPC23680
0.7303	Intermediate Similarity	NPC471043
0.7303	Intermediate Similarity	NPC285982
0.7303	Intermediate Similarity	NPC469546
0.7303	Intermediate Similarity	NPC288699
0.7294	Intermediate Similarity	NPC133391
0.7294	Intermediate Similarity	NPC238991
0.7294	Intermediate Similarity	NPC142683
0.7294	Intermediate Similarity	NPC477270
0.7294	Intermediate Similarity	NPC260956
0.7294	Intermediate Similarity	NPC129080
0.7294	Intermediate Similarity	NPC320514
0.7294	Intermediate Similarity	NPC477271
0.7294	Intermediate Similarity	NPC302661
0.7294	Intermediate Similarity	NPC476935
0.7294	Intermediate Similarity	NPC477269
0.7284	Intermediate Similarity	NPC472311
0.7283	Intermediate Similarity	NPC280877
0.7273	Intermediate Similarity	NPC167877
0.7263	Intermediate Similarity	NPC475867
0.7263	Intermediate Similarity	NPC270155
0.7262	Intermediate Similarity	NPC293418
0.7262	Intermediate Similarity	NPC164999
0.7262	Intermediate Similarity	NPC279667
0.7262	Intermediate Similarity	NPC290508
0.7262	Intermediate Similarity	NPC26139
0.7262	Intermediate Similarity	NPC73052
0.7253	Intermediate Similarity	NPC294263
0.725	Intermediate Similarity	NPC472813
0.7241	Intermediate Similarity	NPC201655
0.7241	Intermediate Similarity	NPC189311
0.7241	Intermediate Similarity	NPC98270
0.7241	Intermediate Similarity	NPC474971
0.7222	Intermediate Similarity	NPC474842
0.7222	Intermediate Similarity	NPC475965
0.7215	Intermediate Similarity	NPC235586
0.7215	Intermediate Similarity	NPC18543
0.7209	Intermediate Similarity	NPC471037
0.7209	Intermediate Similarity	NPC168188
0.7209	Intermediate Similarity	NPC175410
0.7209	Intermediate Similarity	NPC477373
0.7209	Intermediate Similarity	NPC470015
0.7209	Intermediate Similarity	NPC102197
0.7209	Intermediate Similarity	NPC69279
0.7209	Intermediate Similarity	NPC194637
0.7209	Intermediate Similarity	NPC54468
0.7209	Intermediate Similarity	NPC245866
0.7209	Intermediate Similarity	NPC170862
0.7209	Intermediate Similarity	NPC118800
0.7209	Intermediate Similarity	NPC83569
0.7204	Intermediate Similarity	NPC58052
0.7204	Intermediate Similarity	NPC111684
0.7204	Intermediate Similarity	NPC472941
0.7204	Intermediate Similarity	NPC456
0.7204	Intermediate Similarity	NPC3772
0.7204	Intermediate Similarity	NPC125622
0.7195	Intermediate Similarity	NPC92489
0.7191	Intermediate Similarity	NPC254572
0.7191	Intermediate Similarity	NPC183374
0.7191	Intermediate Similarity	NPC48824
0.7191	Intermediate Similarity	NPC472870
0.7191	Intermediate Similarity	NPC211162
0.7191	Intermediate Similarity	NPC250687
0.7191	Intermediate Similarity	NPC190718
0.7191	Intermediate Similarity	NPC229407
0.7176	Intermediate Similarity	NPC38642
0.7174	Intermediate Similarity	NPC470385
0.7174	Intermediate Similarity	NPC470386
0.7174	Intermediate Similarity	NPC100257
0.7174	Intermediate Similarity	NPC224410
0.7174	Intermediate Similarity	NPC475118
0.7159	Intermediate Similarity	NPC12774
0.7159	Intermediate Similarity	NPC264127
0.7159	Intermediate Similarity	NPC70661
0.7158	Intermediate Similarity	NPC287833
0.7143	Intermediate Similarity	NPC472490
0.7143	Intermediate Similarity	NPC473986
0.7143	Intermediate Similarity	NPC304665
0.7143	Intermediate Similarity	NPC154728
0.7143	Intermediate Similarity	NPC198242
0.7143	Intermediate Similarity	NPC474018
0.7143	Intermediate Similarity	NPC211403
0.7143	Intermediate Similarity	NPC201459
0.7143	Intermediate Similarity	NPC126899
0.7143	Intermediate Similarity	NPC158846
0.7128	Intermediate Similarity	NPC106557
0.7128	Intermediate Similarity	NPC216904
0.7128	Intermediate Similarity	NPC43747
0.7128	Intermediate Similarity	NPC292133
0.7128	Intermediate Similarity	NPC121339
0.7126	Intermediate Similarity	NPC165064
0.7126	Intermediate Similarity	NPC164577
0.7126	Intermediate Similarity	NPC470011
0.7126	Intermediate Similarity	NPC263974
0.7126	Intermediate Similarity	NPC146683
0.7125	Intermediate Similarity	NPC472309
0.7125	Intermediate Similarity	NPC197701
0.7113	Intermediate Similarity	NPC474207
0.7113	Intermediate Similarity	NPC474330
0.7111	Intermediate Similarity	NPC66344
0.7111	Intermediate Similarity	NPC262043
0.7111	Intermediate Similarity	NPC474570
0.7111	Intermediate Similarity	NPC269267
0.7111	Intermediate Similarity	NPC116146
0.7111	Intermediate Similarity	NPC305039
0.7111	Intermediate Similarity	NPC24772
0.7097	Intermediate Similarity	NPC255809
0.7097	Intermediate Similarity	NPC317586
0.7097	Intermediate Similarity	NPC470232
0.7097	Intermediate Similarity	NPC470229
0.7097	Intermediate Similarity	NPC241156
0.7097	Intermediate Similarity	NPC266431
0.7097	Intermediate Similarity	NPC470016
0.7097	Intermediate Similarity	NPC37646
0.7097	Intermediate Similarity	NPC98639
0.7093	Intermediate Similarity	NPC170985
0.7093	Intermediate Similarity	NPC226988
0.7089	Intermediate Similarity	NPC475952

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 NPC475932 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	2757
0.2-0.3	4252
0.3-0.4	1261
0.4-0.5	339
0.5-0.6	202
0.6-0.7	128
0.7-0.8	11
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
0.7586	Intermediate Similarity	NPD6903	Approved
0.7386	Intermediate Similarity	NPD5737	Approved
0.7386	Intermediate Similarity	NPD6672	Approved
0.7356	Intermediate Similarity	NPD6684	Approved
0.7356	Intermediate Similarity	NPD6409	Approved
0.7356	Intermediate Similarity	NPD7146	Approved
0.7356	Intermediate Similarity	NPD5330	Approved
0.7356	Intermediate Similarity	NPD7521	Approved
0.7356	Intermediate Similarity	NPD7334	Approved
0.7222	Intermediate Similarity	NPD5207	Approved
0.7209	Intermediate Similarity	NPD4788	Approved
0.7191	Intermediate Similarity	NPD5208	Approved
0.7191	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6098	Approved
0.7125	Intermediate Similarity	NPD6081	Approved
0.7111	Intermediate Similarity	NPD6080	Approved
0.7111	Intermediate Similarity	NPD6673	Approved
0.7111	Intermediate Similarity	NPD6904	Approved
0.7097	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5696	Approved
0.7045	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5692	Phase 3
0.6989	Remote Similarity	NPD6001	Approved
0.6957	Remote Similarity	NPD6050	Approved
0.6957	Remote Similarity	NPD5694	Approved
0.6957	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD4224	Phase 2
0.6915	Remote Similarity	NPD5695	Phase 3
0.6914	Remote Similarity	NPD5777	Approved
0.6897	Remote Similarity	NPD4223	Phase 3
0.6897	Remote Similarity	NPD4221	Approved
0.6897	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3573	Approved
0.6882	Remote Similarity	NPD6399	Phase 3
0.6867	Remote Similarity	NPD3702	Approved
0.6842	Remote Similarity	NPD7732	Phase 3
0.6824	Remote Similarity	NPD3617	Approved
0.6795	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4691	Approved
0.679	Remote Similarity	NPD4747	Approved
0.6778	Remote Similarity	NPD5690	Phase 2
0.6774	Remote Similarity	NPD6079	Approved
0.6774	Remote Similarity	NPD8035	Phase 2
0.6774	Remote Similarity	NPD5281	Approved
0.6774	Remote Similarity	NPD8034	Phase 2
0.6774	Remote Similarity	NPD5284	Approved
0.6771	Remote Similarity	NPD6084	Phase 2
0.6771	Remote Similarity	NPD6083	Phase 2
0.6742	Remote Similarity	NPD3665	Phase 1
0.6742	Remote Similarity	NPD4786	Approved
0.6742	Remote Similarity	NPD3666	Approved
0.6742	Remote Similarity	NPD4197	Approved
0.6742	Remote Similarity	NPD3133	Approved
0.6739	Remote Similarity	NPD5328	Approved
0.6737	Remote Similarity	NPD4629	Approved
0.6737	Remote Similarity	NPD5210	Approved
0.6737	Remote Similarity	NPD5654	Approved
0.6705	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4137	Phase 3
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6634	Remote Similarity	NPD6008	Approved
0.6598	Remote Similarity	NPD5959	Approved
0.6593	Remote Similarity	NPD3618	Phase 1
0.6593	Remote Similarity	NPD5205	Approved
0.6593	Remote Similarity	NPD4693	Phase 3
0.6593	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4694	Approved
0.6593	Remote Similarity	NPD4690	Approved
0.6593	Remote Similarity	NPD4688	Approved
0.6593	Remote Similarity	NPD5280	Approved
0.6593	Remote Similarity	NPD5279	Phase 3
0.6593	Remote Similarity	NPD4689	Approved
0.6593	Remote Similarity	NPD4138	Approved
0.6591	Remote Similarity	NPD4692	Approved
0.6591	Remote Similarity	NPD4139	Approved
0.6569	Remote Similarity	NPD5697	Approved
0.6569	Remote Similarity	NPD6614	Approved
0.6559	Remote Similarity	NPD4753	Phase 2
0.6556	Remote Similarity	NPD3668	Phase 3
0.6548	Remote Similarity	NPD5733	Approved
0.6548	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4687	Approved
0.6548	Remote Similarity	NPD4058	Approved
0.6506	Remote Similarity	NPD5276	Approved
0.6505	Remote Similarity	NPD6881	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD6899	Approved
0.6495	Remote Similarity	NPD7614	Phase 1
0.6495	Remote Similarity	NPD5222	Approved
0.6495	Remote Similarity	NPD5221	Approved
0.6495	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6436	Remote Similarity	NPD6052	Approved
0.6429	Remote Similarity	NPD5173	Approved
0.6408	Remote Similarity	NPD5701	Approved
0.6395	Remote Similarity	NPD6117	Approved
0.6386	Remote Similarity	NPD4789	Approved
0.6381	Remote Similarity	NPD7102	Approved
0.6381	Remote Similarity	NPD6883	Approved
0.6381	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD4195	Approved
0.6354	Remote Similarity	NPD4202	Approved
0.6341	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5360	Phase 3
0.6341	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4697	Phase 3
0.6322	Remote Similarity	NPD6116	Phase 1
0.6321	Remote Similarity	NPD6869	Approved
0.6321	Remote Similarity	NPD6617	Approved
0.6321	Remote Similarity	NPD8130	Phase 1
0.6321	Remote Similarity	NPD6649	Approved
0.6321	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD6847	Approved
0.631	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5286	Approved
0.63	Remote Similarity	NPD4696	Approved
0.63	Remote Similarity	NPD5285	Approved
0.6292	Remote Similarity	NPD4695	Discontinued
0.6289	Remote Similarity	NPD7900	Approved
0.6289	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7748	Approved
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6265	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3698	Phase 2
0.6263	Remote Similarity	NPD4755	Approved
0.6262	Remote Similarity	NPD6882	Approved
0.6262	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD6118	Approved
0.625	Remote Similarity	NPD6115	Approved
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6697	Approved
0.625	Remote Similarity	NPD6114	Approved
0.6238	Remote Similarity	NPD5223	Approved
0.6211	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD4245	Approved
0.619	Remote Similarity	NPD4244	Approved
0.6186	Remote Similarity	NPD5133	Approved
0.6176	Remote Similarity	NPD4633	Approved
0.6176	Remote Similarity	NPD5225	Approved
0.6176	Remote Similarity	NPD5091	Approved
0.6176	Remote Similarity	NPD5224	Approved
0.6176	Remote Similarity	NPD5211	Phase 2
0.6176	Remote Similarity	NPD5226	Approved
0.6168	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4096	Approved
0.6139	Remote Similarity	NPD6404	Discontinued
0.6139	Remote Similarity	NPD4700	Approved
0.6133	Remote Similarity	NPD9298	Approved
0.6118	Remote Similarity	NPD4758	Discontinued
0.6117	Remote Similarity	NPD5174	Approved
0.6117	Remote Similarity	NPD5175	Approved
0.61	Remote Similarity	NPD7902	Approved
0.6092	Remote Similarity	NPD3703	Phase 2
0.6091	Remote Similarity	NPD6274	Approved
0.6091	Remote Similarity	NPD6868	Approved
0.6087	Remote Similarity	NPD5362	Discontinued
0.6064	Remote Similarity	NPD4623	Approved
0.6064	Remote Similarity	NPD4519	Discontinued
0.6058	Remote Similarity	NPD5141	Approved
0.6056	Remote Similarity	NPD344	Approved
0.6056	Remote Similarity	NPD345	Approved
0.6056	Remote Similarity	NPD343	Approved
0.6042	Remote Similarity	NPD6051	Approved
0.604	Remote Similarity	NPD7638	Approved
0.6036	Remote Similarity	NPD6009	Approved
0.6036	Remote Similarity	NPD6317	Approved
0.5982	Remote Similarity	NPD6314	Approved
0.5982	Remote Similarity	NPD6313	Approved
0.5982	Remote Similarity	NPD6335	Approved
0.598	Remote Similarity	NPD7639	Approved
0.598	Remote Similarity	NPD7640	Approved
0.5979	Remote Similarity	NPD5785	Approved
0.5978	Remote Similarity	NPD6435	Approved
0.5976	Remote Similarity	NPD7341	Phase 2
0.5965	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4754	Approved
0.5938	Remote Similarity	NPD4518	Approved
0.5934	Remote Similarity	NPD5368	Approved
0.5929	Remote Similarity	NPD7100	Approved
0.5929	Remote Similarity	NPD7101	Approved
0.5921	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8039	Approved
0.59	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7115	Discovery
0.5888	Remote Similarity	NPD4730	Approved
0.5888	Remote Similarity	NPD5128	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