NPASS Compound

Structure

CID324667 OpenBabel06191716172D 29 30 0 0 1 0 0 0 0 0999 V2000 -6.7047 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5428 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1904 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -3.3871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8666 2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5143 2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8666 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0285 2.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3524 2.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 2.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7047 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1904 2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 2.4194 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6762 -0.9677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6762 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -0.4839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6762 -1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5143 0.4839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8381 0.4839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6762 2.9032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 1.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5143 -2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3524 0.9677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5143 -0.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 27 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 2 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 17 28 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 22 1 1 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 26 1 6 0 0 0 21 28 1 0 0 0 0 22 16 1 6 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.2
Volume:	417.668
LogP:	2.114
LogD:	0.607
LogS:	-3.976
# Rotatable Bonds:	9
TPSA:	105.59
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	4.9
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.598
MDCK Permeability:	2.2219512175070122e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.675
Plasma Protein Binding (PPB):	89.47904205322266%
Volume Distribution (VD):	1.292
Pgp-substrate:	11.923205375671387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	4.743
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.392
Human Hepatotoxicity (H-HT):	0.976
Drug-inuced Liver Injury (DILI):	0.704
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.519
Skin Sensitization:	0.239
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.642

Download Data

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

Natural Product: NPC324667

Natural Product ID:	NPC324667
*Common Name:**	Trichothosporon A
IUPAC Name:	methyl (1R,2R,4R,6R)-4-hydroxy-6-[(2E,4E,6E)-1-hydroxy-3,7,11-trimethyldodeca-2,4,6,10-tetraenyl]-5-oxo-3,7-dioxabicyclo[4.1.0]heptane-2-carboxylate
Synonyms:	Trichothosporon A
Standard InCHIKey:	IREYQNQKCFYKND-ISSAMECVSA-N
Standard InCHI:	InChI=1S/C22H30O7/c1-13(2)8-6-9-14(3)10-7-11-15(4)12-16(23)22-18(24)21(26)28-17(19(22)29-22)20(25)27-5/h7-8,10-12,16-17,19,21,23,26H,6,9H2,1-5H3/b11-7+,14-10+,15-12+/t16?,17-,19-,21-,22+/m1/s1
SMILES:	COC(=O)[C@@H]1O[C@@H](O)C(=O)[C@]2([C@@H]1O2)C(/C=C(/C=C/C=C(/CCC=C(C)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1835974
PubChem CID:	56602067
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO30894	Trichothecium species	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[21978324]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[559739]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	10000.0	nM	PMID[559739]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	10000.0	nM	PMID[559739]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[559739]

☑ 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 NPC324667 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	225
0.1-0.2	1511
0.2-0.3	5537
0.3-0.4	10591
0.4-0.5	15563
0.5-0.6	7269
0.6-0.7	1877
0.7-0.8	113
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7938	Intermediate Similarity	NPC137368
0.781	Intermediate Similarity	NPC118902
0.781	Intermediate Similarity	NPC469980
0.781	Intermediate Similarity	NPC104161
0.7757	Intermediate Similarity	NPC266514
0.7706	Intermediate Similarity	NPC89408
0.7685	Intermediate Similarity	NPC327106
0.7525	Intermediate Similarity	NPC9447
0.7525	Intermediate Similarity	NPC472199
0.7525	Intermediate Similarity	NPC472197
0.7524	Intermediate Similarity	NPC475949
0.7523	Intermediate Similarity	NPC472507
0.7475	Intermediate Similarity	NPC475037
0.7453	Intermediate Similarity	NPC476270
0.7449	Intermediate Similarity	NPC475034
0.7426	Intermediate Similarity	NPC316228
0.7426	Intermediate Similarity	NPC313670
0.7411	Intermediate Similarity	NPC66108
0.7387	Intermediate Similarity	NPC472508
0.7383	Intermediate Similarity	NPC195510
0.7383	Intermediate Similarity	NPC39996
0.7383	Intermediate Similarity	NPC13171
0.7379	Intermediate Similarity	NPC472198
0.7347	Intermediate Similarity	NPC475035
0.7339	Intermediate Similarity	NPC472749
0.7339	Intermediate Similarity	NPC472751
0.7333	Intermediate Similarity	NPC474194
0.7315	Intermediate Similarity	NPC472750
0.7315	Intermediate Similarity	NPC472747
0.73	Intermediate Similarity	NPC471738
0.73	Intermediate Similarity	NPC86005
0.73	Intermediate Similarity	NPC179659
0.7282	Intermediate Similarity	NPC478037
0.7282	Intermediate Similarity	NPC478036
0.7273	Intermediate Similarity	NPC474285
0.7273	Intermediate Similarity	NPC254538
0.7264	Intermediate Similarity	NPC475284
0.7264	Intermediate Similarity	NPC161855
0.7264	Intermediate Similarity	NPC281608
0.7255	Intermediate Similarity	NPC475879
0.7255	Intermediate Similarity	NPC274075
0.7255	Intermediate Similarity	NPC473311
0.7248	Intermediate Similarity	NPC472748
0.7248	Intermediate Similarity	NPC474741
0.7248	Intermediate Similarity	NPC472756
0.7248	Intermediate Similarity	NPC469869
0.7238	Intermediate Similarity	NPC473291
0.7238	Intermediate Similarity	NPC279722
0.7228	Intermediate Similarity	NPC471756
0.7228	Intermediate Similarity	NPC201046
0.7228	Intermediate Similarity	NPC471755
0.7212	Intermediate Similarity	NPC475927
0.7212	Intermediate Similarity	NPC475832
0.7207	Intermediate Similarity	NPC14862
0.7207	Intermediate Similarity	NPC264819
0.7207	Intermediate Similarity	NPC233379
0.7207	Intermediate Similarity	NPC474664
0.72	Intermediate Similarity	NPC278283
0.7196	Intermediate Similarity	NPC469870
0.7196	Intermediate Similarity	NPC469871
0.7196	Intermediate Similarity	NPC475053
0.7172	Intermediate Similarity	NPC219966
0.717	Intermediate Similarity	NPC40812
0.7156	Intermediate Similarity	NPC475945
0.7156	Intermediate Similarity	NPC475871
0.7154	Intermediate Similarity	NPC476863
0.7154	Intermediate Similarity	NPC476862
0.7143	Intermediate Similarity	NPC214694
0.7143	Intermediate Similarity	NPC15218
0.7143	Intermediate Similarity	NPC38154
0.7143	Intermediate Similarity	NPC270013
0.7143	Intermediate Similarity	NPC170204
0.7143	Intermediate Similarity	NPC14961
0.7131	Intermediate Similarity	NPC476859
0.713	Intermediate Similarity	NPC472753
0.713	Intermediate Similarity	NPC474339
0.713	Intermediate Similarity	NPC164598
0.713	Intermediate Similarity	NPC28304
0.713	Intermediate Similarity	NPC201718
0.713	Intermediate Similarity	NPC298255
0.7129	Intermediate Similarity	NPC477959
0.7128	Intermediate Similarity	NPC473948
0.7117	Intermediate Similarity	NPC324327
0.7117	Intermediate Similarity	NPC194620
0.7117	Intermediate Similarity	NPC474421
0.7117	Intermediate Similarity	NPC72813
0.7117	Intermediate Similarity	NPC477513
0.7117	Intermediate Similarity	NPC326994
0.7115	Intermediate Similarity	NPC61201
0.7115	Intermediate Similarity	NPC320089
0.7103	Intermediate Similarity	NPC187761
0.7103	Intermediate Similarity	NPC307517
0.7103	Intermediate Similarity	NPC300584
0.7103	Intermediate Similarity	NPC83895
0.7103	Intermediate Similarity	NPC61630
0.7103	Intermediate Similarity	NPC81483
0.7103	Intermediate Similarity	NPC471144
0.7103	Intermediate Similarity	NPC169468
0.7087	Intermediate Similarity	NPC303451
0.7087	Intermediate Similarity	NPC6414
0.7087	Intermediate Similarity	NPC65359
0.7083	Intermediate Similarity	NPC133377
0.708	Intermediate Similarity	NPC46407
0.7075	Intermediate Similarity	NPC306041
0.7075	Intermediate Similarity	NPC195645
0.7075	Intermediate Similarity	NPC165332
0.7075	Intermediate Similarity	NPC473859
0.7075	Intermediate Similarity	NPC180722
0.7075	Intermediate Similarity	NPC241911
0.7073	Intermediate Similarity	NPC476851
0.7073	Intermediate Similarity	NPC476854
0.7071	Intermediate Similarity	NPC52923
0.7064	Intermediate Similarity	NPC471148
0.7064	Intermediate Similarity	NPC474747
0.7064	Intermediate Similarity	NPC472754
0.7064	Intermediate Similarity	NPC149371
0.7059	Intermediate Similarity	NPC470137
0.7059	Intermediate Similarity	NPC473228
0.7059	Intermediate Similarity	NPC183353
0.7059	Intermediate Similarity	NPC469812
0.7059	Intermediate Similarity	NPC470829
0.7059	Intermediate Similarity	NPC170880
0.7059	Intermediate Similarity	NPC472008
0.7054	Intermediate Similarity	NPC55972
0.7054	Intermediate Similarity	NPC473807
0.7054	Intermediate Similarity	NPC193765
0.7054	Intermediate Similarity	NPC327286
0.7054	Intermediate Similarity	NPC169888
0.7054	Intermediate Similarity	NPC475960
0.7054	Intermediate Similarity	NPC117604
0.7053	Intermediate Similarity	NPC229655
0.7048	Intermediate Similarity	NPC294293
0.7048	Intermediate Similarity	NPC81386
0.7048	Intermediate Similarity	NPC474035
0.7048	Intermediate Similarity	NPC71589
0.7037	Intermediate Similarity	NPC22149
0.7037	Intermediate Similarity	NPC288876
0.7037	Intermediate Similarity	NPC255677
0.7037	Intermediate Similarity	NPC306344
0.7034	Intermediate Similarity	NPC268958
0.703	Intermediate Similarity	NPC196381
0.7027	Intermediate Similarity	NPC9303
0.7027	Intermediate Similarity	NPC469852
0.7027	Intermediate Similarity	NPC478038
0.7027	Intermediate Similarity	NPC16313
0.7027	Intermediate Similarity	NPC314244
0.7027	Intermediate Similarity	NPC475802
0.7019	Intermediate Similarity	NPC469627
0.7018	Intermediate Similarity	NPC317107
0.7016	Intermediate Similarity	NPC476852
0.7016	Intermediate Similarity	NPC476855
0.701	Intermediate Similarity	NPC321728
0.7009	Intermediate Similarity	NPC236176
0.7009	Intermediate Similarity	NPC20066
0.7009	Intermediate Similarity	NPC471146
0.7009	Intermediate Similarity	NPC471145
0.7009	Intermediate Similarity	NPC472290
0.7	Intermediate Similarity	NPC475873
0.7	Intermediate Similarity	NPC266718
0.7	Intermediate Similarity	NPC472755
0.7	Intermediate Similarity	NPC309398
0.7	Intermediate Similarity	NPC32676
0.6991	Remote Similarity	NPC313668
0.6991	Remote Similarity	NPC315836
0.699	Remote Similarity	NPC87306
0.699	Remote Similarity	NPC478110
0.6984	Remote Similarity	NPC242486
0.6984	Remote Similarity	NPC15215
0.6983	Remote Similarity	NPC80650
0.6981	Remote Similarity	NPC475659
0.6981	Remote Similarity	NPC474947
0.6981	Remote Similarity	NPC101051
0.6981	Remote Similarity	NPC107476
0.6979	Remote Similarity	NPC110813
0.6972	Remote Similarity	NPC473332
0.6972	Remote Similarity	NPC47880
0.6972	Remote Similarity	NPC474742
0.6972	Remote Similarity	NPC133907
0.6972	Remote Similarity	NPC46998
0.6972	Remote Similarity	NPC128733
0.6972	Remote Similarity	NPC110443
0.6972	Remote Similarity	NPC185141
0.6961	Remote Similarity	NPC45409
0.6961	Remote Similarity	NPC472007
0.6957	Remote Similarity	NPC317687
0.6952	Remote Similarity	NPC475912
0.6952	Remote Similarity	NPC320552
0.6952	Remote Similarity	NPC212486
0.6952	Remote Similarity	NPC165383
0.6944	Remote Similarity	NPC308567
0.6944	Remote Similarity	NPC255592
0.6944	Remote Similarity	NPC261377
0.6937	Remote Similarity	NPC86095
0.6937	Remote Similarity	NPC477510
0.6937	Remote Similarity	NPC220964
0.6937	Remote Similarity	NPC470104
0.6937	Remote Similarity	NPC471143
0.6937	Remote Similarity	NPC475676
0.6931	Remote Similarity	NPC471156
0.6931	Remote Similarity	NPC477747

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 NPC324667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1850
0.2-0.3	4019
0.3-0.4	2079
0.4-0.5	786
0.5-0.6	183
0.6-0.7	44
0.7-0.8	2
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
0.7525	Intermediate Similarity	NPD7983	Approved
0.7075	Intermediate Similarity	NPD7839	Suspended
0.7059	Intermediate Similarity	NPD8513	Phase 3
0.7059	Intermediate Similarity	NPD8516	Approved
0.7059	Intermediate Similarity	NPD8517	Approved
0.7059	Intermediate Similarity	NPD8515	Approved
0.6923	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD46	Approved
0.6917	Remote Similarity	NPD8444	Approved
0.6792	Remote Similarity	NPD5778	Approved
0.6792	Remote Similarity	NPD5779	Approved
0.6789	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8299	Approved
0.6748	Remote Similarity	NPD8340	Approved
0.6748	Remote Similarity	NPD8342	Approved
0.6748	Remote Similarity	NPD8341	Approved
0.6733	Remote Similarity	NPD6110	Phase 1
0.6724	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7642	Approved
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD7829	Approved
0.6604	Remote Similarity	NPD7838	Discovery
0.656	Remote Similarity	NPD8451	Approved
0.6559	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7641	Discontinued
0.6508	Remote Similarity	NPD8074	Phase 3
0.6508	Remote Similarity	NPD8448	Approved
0.64	Remote Similarity	NPD8328	Phase 3
0.6383	Remote Similarity	NPD898	Approved
0.6383	Remote Similarity	NPD897	Approved
0.6383	Remote Similarity	NPD896	Approved
0.6357	Remote Similarity	NPD8391	Approved
0.6357	Remote Similarity	NPD8390	Approved
0.6357	Remote Similarity	NPD8392	Approved
0.6356	Remote Similarity	NPD6371	Approved
0.6355	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8961	Approved
0.6273	Remote Similarity	NPD5282	Discontinued
0.624	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6411	Approved
0.6239	Remote Similarity	NPD7637	Suspended
0.6226	Remote Similarity	NPD5786	Approved
0.619	Remote Similarity	NPD8080	Discontinued
0.6186	Remote Similarity	NPD6686	Approved
0.6186	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7329	Approved
0.6172	Remote Similarity	NPD8273	Phase 1
0.6132	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4252	Approved
0.6087	Remote Similarity	NPD5344	Discontinued
0.6077	Remote Similarity	NPD7736	Approved
0.6075	Remote Similarity	NPD4249	Approved
0.6063	Remote Similarity	NPD6370	Approved
0.6033	Remote Similarity	NPD2204	Approved
0.6032	Remote Similarity	NPD6319	Approved
0.6019	Remote Similarity	NPD4250	Approved
0.6019	Remote Similarity	NPD4251	Approved
0.6017	Remote Similarity	NPD5048	Discontinued
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD4269	Approved
0.598	Remote Similarity	NPD4756	Discovery
0.5969	Remote Similarity	NPD7492	Approved
0.5962	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7154	Phase 3
0.5929	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD6616	Approved
0.592	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7115	Discovery
0.5909	Remote Similarity	NPD7319	Approved
0.5906	Remote Similarity	NPD6054	Approved
0.5905	Remote Similarity	NPD5369	Approved
0.5902	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3181	Approved
0.5882	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD7078	Approved
0.5859	Remote Similarity	NPD6015	Approved
0.5859	Remote Similarity	NPD6016	Approved
0.5849	Remote Similarity	NPD6435	Approved
0.5833	Remote Similarity	NPD5363	Approved
0.5833	Remote Similarity	NPD6412	Phase 2
0.5821	Remote Similarity	NPD7260	Phase 2
0.5814	Remote Similarity	NPD5988	Approved
0.581	Remote Similarity	NPD4821	Approved
0.581	Remote Similarity	NPD4819	Approved
0.581	Remote Similarity	NPD4820	Approved
0.581	Remote Similarity	NPD4822	Approved
0.5809	Remote Similarity	NPD8415	Approved
0.5804	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7507	Approved
0.5794	Remote Similarity	NPD6009	Approved
0.5781	Remote Similarity	NPD6059	Approved
0.5776	Remote Similarity	NPD4225	Approved
0.5769	Remote Similarity	NPD4271	Approved
0.5769	Remote Similarity	NPD4268	Approved
0.5766	Remote Similarity	NPD5370	Suspended
0.5761	Remote Similarity	NPD8959	Approved
0.5745	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5785	Approved
0.5701	Remote Similarity	NPD5209	Approved
0.5699	Remote Similarity	NPD6109	Phase 1
0.5691	Remote Similarity	NPD6421	Discontinued
0.568	Remote Similarity	NPD4632	Approved
0.5669	Remote Similarity	NPD7500	Approved
0.566	Remote Similarity	NPD5368	Approved
0.5648	Remote Similarity	NPD5362	Discontinued
0.5619	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD7503	Approved
0.5615	Remote Similarity	NPD6921	Approved
0.56	Remote Similarity	NPD8297	Approved
0.56	Remote Similarity	NPD6882	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