NPASS Compound

Structure

CID82592 OpenBabel06191715422D 22 23 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 4 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 10 1 0 0 0 0 9 13 1 0 0 0 0 10 17 1 6 0 0 0 11 8 1 6 0 0 0 11 22 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.14
Volume:	310.375
LogP:	2.998
LogD:	2.543
LogS:	-3.432
# Rotatable Bonds:	6
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	3.393
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.769
MDCK Permeability:	4.387423177831806e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.118
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.74
Plasma Protein Binding (PPB):	87.01305389404297%
Volume Distribution (VD):	0.79
Pgp-substrate:	11.993722915649414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.431
CYP1A2-substrate:	0.594
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.401
CYP3A4-inhibitor:	0.304
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	12.871
Half-life (T1/2):	0.749

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.244
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.519
Carcinogencity:	0.869
Eye Corrosion:	0.015
Eye Irritation:	0.43
Respiratory Toxicity:	0.83

Download Data

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

Natural Product: NPC82592

Natural Product ID:	NPC82592
*Common Name:**	Fusarentin 6,7-Dimethylether
IUPAC Name:	(3S)-8-hydroxy-3-[(2S)-2-hydroxypentyl]-6,7-dimethoxy-3,4-dihydroisochromen-1-one
Synonyms:	Fusarentin 6,7-Dimethylether
Standard InCHIKey:	QBCACQPIGRTBHJ-QWRGUYRKSA-N
Standard InCHI:	InChI=1S/C16H22O6/c1-4-5-10(17)8-11-6-9-7-12(20-2)15(21-3)14(18)13(9)16(19)22-11/h7,10-11,17-18H,4-6,8H2,1-3H3/t10-,11-/m0/s1
SMILES:	CCC[C@@H](C[C@@H]1Cc2cc(c(c(c2C(=O)O1)O)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668327
PubChem CID:	11758702
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
NPO32863	colletotrichum sp.	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21174408]
NPO31360	Colletotrichum	Genus	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21174408]

☑ 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	10

Activity Type	# Activity
Cell Line	4
Individual Protein	2
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	120800.0	nM	PMID[541948]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	161100.0	nM	PMID[541948]
NPT793	Cell Line	MOLT-3	Homo sapiens	IC50	=	115300.0	nM	PMID[541948]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	>	16100.0	nM	PMID[541948]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	128000.0	nM	PMID[541948]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	161100.0	nM	PMID[541948]
NPT1	Others	Radical scavenging activity		IC50	>	322000.0	nM	PMID[541948]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	644000.0	nM	PMID[541948]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	>	644000.0	nM	PMID[541948]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14400.0	nM	PMID[541948]

☑ 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 NPC82592 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	354
0.1-0.2	1479
0.2-0.3	3744
0.3-0.4	8159
0.4-0.5	10080
0.5-0.6	3511
0.6-0.7	5054
0.7-0.8	6823
0.8-0.85	2605
0.85-0.9	789
0.9-0.95	87
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC16082
0.9932	High Similarity	NPC281477
0.9866	High Similarity	NPC77679
0.9866	High Similarity	NPC84935
0.9866	High Similarity	NPC190020
0.9799	High Similarity	NPC150227
0.9732	High Similarity	NPC199926
0.96	High Similarity	NPC79998
0.9536	High Similarity	NPC227062
0.953	High Similarity	NPC70016
0.953	High Similarity	NPC215921
0.9463	High Similarity	NPC96501
0.9404	High Similarity	NPC116850
0.9404	High Similarity	NPC144801
0.9404	High Similarity	NPC197188
0.9404	High Similarity	NPC238672
0.9404	High Similarity	NPC291510
0.9404	High Similarity	NPC43872
0.9351	High Similarity	NPC24627
0.9338	High Similarity	NPC295646
0.9281	High Similarity	NPC54928
0.9272	High Similarity	NPC200773
0.9272	High Similarity	NPC228662
0.9272	High Similarity	NPC240768
0.9267	High Similarity	NPC270160
0.9267	High Similarity	NPC237440
0.9252	High Similarity	NPC51106
0.9252	High Similarity	NPC469542
0.9211	High Similarity	NPC167903
0.9205	High Similarity	NPC469670
0.9205	High Similarity	NPC469619
0.9189	High Similarity	NPC210425
0.9189	High Similarity	NPC86373
0.9189	High Similarity	NPC280404
0.9189	High Similarity	NPC277426
0.9184	High Similarity	NPC469579
0.9177	High Similarity	NPC20237
0.9172	High Similarity	NPC249181
0.9161	High Similarity	NPC470339
0.9161	High Similarity	NPC329091
0.9145	High Similarity	NPC473732
0.9145	High Similarity	NPC204350
0.9122	High Similarity	NPC472006
0.9119	High Similarity	NPC283041
0.9116	High Similarity	NPC67650
0.9116	High Similarity	NPC1704
0.9114	High Similarity	NPC191930
0.9108	High Similarity	NPC215612
0.9108	High Similarity	NPC472964
0.9103	High Similarity	NPC36217
0.9103	High Similarity	NPC472055
0.9103	High Similarity	NPC200594
0.9103	High Similarity	NPC472902
0.9097	High Similarity	NPC241904
0.9097	High Similarity	NPC300727
0.9091	High Similarity	NPC38898
0.9091	High Similarity	NPC16286
0.9091	High Similarity	NPC67396
0.9091	High Similarity	NPC20541
0.9085	High Similarity	NPC475116
0.9079	High Similarity	NPC179178
0.9067	High Similarity	NPC260946
0.9067	High Similarity	NPC107625
0.9067	High Similarity	NPC32058
0.9067	High Similarity	NPC85734
0.9067	High Similarity	NPC138978
0.906	High Similarity	NPC27106
0.9057	High Similarity	NPC472452
0.9054	High Similarity	NPC474385
0.9051	High Similarity	NPC7483
0.9051	High Similarity	NPC475985
0.9045	High Similarity	NPC473106
0.9045	High Similarity	NPC103201
0.9045	High Similarity	NPC349525
0.9038	High Similarity	NPC476242
0.9038	High Similarity	NPC238381
0.9038	High Similarity	NPC477410
0.9032	High Similarity	NPC24640
0.9032	High Similarity	NPC274730
0.9032	High Similarity	NPC197751
0.9026	High Similarity	NPC18727
0.9007	High Similarity	NPC476463
0.9007	High Similarity	NPC210320
0.9	High Similarity	NPC83272
0.9	High Similarity	NPC6588
0.9	High Similarity	NPC477154
0.9	High Similarity	NPC117854
0.8994	High Similarity	NPC475888
0.8994	High Similarity	NPC326520
0.8994	High Similarity	NPC471788
0.8987	High Similarity	NPC211107
0.8987	High Similarity	NPC201800
0.8987	High Similarity	NPC48860
0.8981	High Similarity	NPC228785
0.8981	High Similarity	NPC14353
0.8981	High Similarity	NPC155302
0.8981	High Similarity	NPC56085
0.8981	High Similarity	NPC321399
0.8981	High Similarity	NPC292415
0.8981	High Similarity	NPC161947
0.898	High Similarity	NPC471819
0.8974	High Similarity	NPC475267
0.8974	High Similarity	NPC48208
0.8974	High Similarity	NPC129684
0.8974	High Similarity	NPC474836
0.8974	High Similarity	NPC156057
0.8974	High Similarity	NPC474208
0.8974	High Similarity	NPC108456
0.8974	High Similarity	NPC179732
0.8974	High Similarity	NPC469584
0.8974	High Similarity	NPC474055
0.8974	High Similarity	NPC472598
0.8974	High Similarity	NPC299520
0.8974	High Similarity	NPC162869
0.8968	High Similarity	NPC470327
0.8968	High Similarity	NPC45849
0.8968	High Similarity	NPC200761
0.8968	High Similarity	NPC99381
0.8968	High Similarity	NPC477503
0.8961	High Similarity	NPC199773
0.8961	High Similarity	NPC236637
0.8961	High Similarity	NPC302950
0.8961	High Similarity	NPC219582
0.8961	High Similarity	NPC289968
0.8954	High Similarity	NPC151473
0.8954	High Similarity	NPC338131
0.8951	High Similarity	NPC471181
0.8947	High Similarity	NPC215711
0.8947	High Similarity	NPC73411
0.894	High Similarity	NPC268366
0.894	High Similarity	NPC473023
0.8938	High Similarity	NPC13481
0.8938	High Similarity	NPC207575
0.8938	High Similarity	NPC477517
0.8938	High Similarity	NPC170245
0.8931	High Similarity	NPC186686
0.8931	High Similarity	NPC474350
0.8931	High Similarity	NPC474240
0.8924	High Similarity	NPC87431
0.8924	High Similarity	NPC61010
0.8924	High Similarity	NPC201560
0.8924	High Similarity	NPC117985
0.8924	High Similarity	NPC40491
0.8924	High Similarity	NPC474186
0.8924	High Similarity	NPC278052
0.8924	High Similarity	NPC112418
0.8924	High Similarity	NPC474779
0.8919	High Similarity	NPC158472
0.8917	High Similarity	NPC87317
0.8917	High Similarity	NPC210459
0.8917	High Similarity	NPC315157
0.8917	High Similarity	NPC100123
0.8917	High Similarity	NPC45846
0.8917	High Similarity	NPC85121
0.8912	High Similarity	NPC472602
0.8912	High Similarity	NPC212693
0.8912	High Similarity	NPC94248
0.891	High Similarity	NPC472050
0.891	High Similarity	NPC472626
0.891	High Similarity	NPC317383
0.891	High Similarity	NPC209614
0.891	High Similarity	NPC235165
0.891	High Similarity	NPC35038
0.891	High Similarity	NPC470328
0.891	High Similarity	NPC278778
0.891	High Similarity	NPC195796
0.891	High Similarity	NPC320825
0.891	High Similarity	NPC250922
0.891	High Similarity	NPC326037
0.891	High Similarity	NPC291878
0.891	High Similarity	NPC255106
0.891	High Similarity	NPC13858
0.8903	High Similarity	NPC25127
0.8903	High Similarity	NPC287504
0.8903	High Similarity	NPC89474
0.8903	High Similarity	NPC192189
0.8896	High Similarity	NPC75695
0.8889	High Similarity	NPC4423
0.8889	High Similarity	NPC77325
0.8882	High Similarity	NPC472036
0.8882	High Similarity	NPC116745
0.8882	High Similarity	NPC474024
0.8882	High Similarity	NPC298847
0.8875	High Similarity	NPC293319
0.8875	High Similarity	NPC8070
0.8875	High Similarity	NPC112981
0.8868	High Similarity	NPC471745
0.8868	High Similarity	NPC474763
0.8867	High Similarity	NPC258307
0.8861	High Similarity	NPC472630
0.8861	High Similarity	NPC155101
0.8861	High Similarity	NPC263449
0.8861	High Similarity	NPC287328
0.8861	High Similarity	NPC282009
0.8861	High Similarity	NPC470326
0.8861	High Similarity	NPC299436
0.8861	High Similarity	NPC475886
0.8861	High Similarity	NPC471744
0.8861	High Similarity	NPC200746
0.8861	High Similarity	NPC470183

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 NPC82592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	920
0.2-0.3	1954
0.3-0.4	2567
0.4-0.5	1757
0.5-0.6	972
0.6-0.7	493
0.7-0.8	139
0.8-0.85	28
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8961	High Similarity	NPD1934	Approved
0.879	High Similarity	NPD4868	Clinical (unspecified phase)
0.8782	High Similarity	NPD2393	Clinical (unspecified phase)
0.875	High Similarity	NPD6232	Discontinued
0.8725	High Similarity	NPD970	Clinical (unspecified phase)
0.8662	High Similarity	NPD2801	Approved
0.8642	High Similarity	NPD6166	Phase 2
0.8642	High Similarity	NPD6168	Clinical (unspecified phase)
0.8642	High Similarity	NPD6167	Clinical (unspecified phase)
0.8627	High Similarity	NPD2532	Approved
0.8627	High Similarity	NPD2534	Approved
0.8627	High Similarity	NPD2533	Approved
0.8589	High Similarity	NPD7473	Discontinued
0.8553	High Similarity	NPD3882	Suspended
0.8545	High Similarity	NPD7074	Phase 3
0.8544	High Similarity	NPD1465	Phase 2
0.8537	High Similarity	NPD3818	Discontinued
0.8503	High Similarity	NPD4338	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD3817	Phase 2
0.8485	Intermediate Similarity	NPD7054	Approved
0.8485	Intermediate Similarity	NPD5844	Phase 1
0.8446	Intermediate Similarity	NPD230	Phase 1
0.8434	Intermediate Similarity	NPD7472	Approved
0.8354	Intermediate Similarity	NPD4380	Phase 2
0.8323	Intermediate Similarity	NPD1511	Approved
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8274	Intermediate Similarity	NPD6797	Phase 2
0.8274	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7075	Discontinued
0.8225	Intermediate Similarity	NPD7251	Discontinued
0.8221	Intermediate Similarity	NPD6234	Discontinued
0.8217	Intermediate Similarity	NPD1512	Approved
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7808	Phase 3
0.8171	Intermediate Similarity	NPD5494	Approved
0.816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD37	Approved
0.8098	Intermediate Similarity	NPD4965	Approved
0.8098	Intermediate Similarity	NPD4966	Approved
0.8098	Intermediate Similarity	NPD4967	Phase 2
0.8095	Intermediate Similarity	NPD7228	Approved
0.8089	Intermediate Similarity	NPD6799	Approved
0.8072	Intermediate Similarity	NPD5711	Approved
0.8072	Intermediate Similarity	NPD5710	Approved
0.8052	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD1549	Phase 2
0.7961	Intermediate Similarity	NPD447	Suspended
0.7933	Intermediate Similarity	NPD3027	Phase 3
0.7927	Intermediate Similarity	NPD5402	Approved
0.7925	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1510	Phase 2
0.7922	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7199	Phase 2
0.7898	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4628	Phase 3
0.7895	Intermediate Similarity	NPD943	Approved
0.7895	Intermediate Similarity	NPD1240	Approved
0.7871	Intermediate Similarity	NPD2935	Discontinued
0.7853	Intermediate Similarity	NPD7411	Suspended
0.7836	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD3749	Approved
0.7818	Intermediate Similarity	NPD5353	Approved
0.7818	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7792	Intermediate Similarity	NPD1607	Approved
0.7785	Intermediate Similarity	NPD3750	Approved
0.7784	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1653	Approved
0.7756	Intermediate Similarity	NPD2796	Approved
0.7736	Intermediate Similarity	NPD6190	Approved
0.7727	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2800	Approved
0.7716	Intermediate Similarity	NPD5403	Approved
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD9269	Phase 2
0.7701	Intermediate Similarity	NPD7685	Pre-registration
0.7682	Intermediate Similarity	NPD9494	Approved
0.7665	Intermediate Similarity	NPD7768	Phase 2
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5242	Approved
0.7602	Intermediate Similarity	NPD3926	Phase 2
0.76	Intermediate Similarity	NPD7240	Approved
0.7593	Intermediate Similarity	NPD5401	Approved
0.7588	Intermediate Similarity	NPD1247	Approved
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.7566	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD8151	Discontinued
0.7562	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD920	Approved
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3748	Approved
0.7452	Intermediate Similarity	NPD6651	Approved
0.7432	Intermediate Similarity	NPD9268	Approved
0.7421	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD6100	Approved
0.7419	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7435	Discontinued
0.7391	Intermediate Similarity	NPD1243	Approved
0.7391	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1933	Approved
0.7378	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2799	Discontinued
0.7345	Intermediate Similarity	NPD5953	Discontinued
0.733	Intermediate Similarity	NPD7286	Phase 2
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7321	Intermediate Similarity	NPD6386	Approved
0.7321	Intermediate Similarity	NPD6385	Approved
0.7317	Intermediate Similarity	NPD7390	Discontinued
0.7305	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7284	Intermediate Similarity	NPD1652	Phase 2
0.7278	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7266	Discontinued
0.7256	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7033	Discontinued
0.7249	Intermediate Similarity	NPD5005	Approved
0.7249	Intermediate Similarity	NPD5006	Approved
0.7248	Intermediate Similarity	NPD9545	Approved
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7237	Intermediate Similarity	NPD9717	Approved
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7208	Intermediate Similarity	NPD1203	Approved
0.7197	Intermediate Similarity	NPD3764	Approved
0.719	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8127	Discontinued
0.7179	Intermediate Similarity	NPD6832	Phase 2
0.7171	Intermediate Similarity	NPD422	Phase 1
0.717	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5124	Phase 1
0.717	Intermediate Similarity	NPD6355	Discontinued
0.7165	Intermediate Similarity	NPD7874	Approved
0.7165	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2344	Approved
0.7134	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4110	Phase 3
0.7128	Intermediate Similarity	NPD4420	Approved
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7680	Approved
0.712	Intermediate Similarity	NPD7698	Approved
0.7118	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9493	Approved
0.7099	Intermediate Similarity	NPD5405	Approved
0.7099	Intermediate Similarity	NPD5404	Approved
0.7099	Intermediate Similarity	NPD5408	Approved
0.7099	Intermediate Similarity	NPD5406	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD2313	Discontinued
0.7089	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD7871	Phase 2
0.7083	Intermediate Similarity	NPD7870	Phase 2
0.7074	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6674	Discontinued
0.7073	Intermediate Similarity	NPD2654	Approved
0.7072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4908	Phase 1
0.7068	Intermediate Similarity	NPD6823	Phase 2
0.7062	Intermediate Similarity	NPD2403	Approved
0.7062	Intermediate Similarity	NPD7701	Phase 2
0.7059	Intermediate Similarity	NPD3705	Approved
0.7059	Intermediate Similarity	NPD6535	Approved
0.7059	Intermediate Similarity	NPD6534	Approved
0.7039	Intermediate Similarity	NPD4626	Approved
0.7035	Intermediate Similarity	NPD8455	Phase 2
0.703	Intermediate Similarity	NPD8166	Discontinued
0.7024	Intermediate Similarity	NPD6273	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