NPASS Compound

Structure

CID84142 OpenBabel06191715422D 28 30 0 0 1 0 0 0 0 0999 V2000 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 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 -3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -3.0000 -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 -2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 0.8660 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 11 1 0 0 0 0 4 5 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 27 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 13 22 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 21 3 1 1 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.11
Volume:	381.27
LogP:	3.067
LogD:	2.356
LogS:	-3.507
# Rotatable Bonds:	4
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	4.069
Fsp3:	0.19
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:	-5.206
MDCK Permeability:	2.1300702428561635e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.897
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.84

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	86.8814468383789%
Volume Distribution (VD):	1.071
Pgp-substrate:	8.86097240447998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.483
CYP2C19-inhibitor:	0.825
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.607
CYP2D6-inhibitor:	0.913
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	1.621
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.832
Rat Oral Acute Toxicity:	0.855
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.949
Carcinogencity:	0.75
Eye Corrosion:	0.003
Eye Irritation:	0.304
Respiratory Toxicity:	0.469

Download Data

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

Natural Product: NPC84142

Natural Product ID:	NPC84142
*Common Name:**	(-)-Mitorubrin
IUPAC Name:	[(7R)-7-methyl-6,8-dioxo-3-[(E)-prop-1-enyl]isochromen-7-yl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:	(-)-Mitorubrin
Standard InCHIKey:	ZLULUXWJVBHEMS-KTBYTZPXSA-N
Standard InCHI:	InChI=1S/C21H18O7/c1-4-5-14-7-12-8-17(24)21(3,19(25)15(12)10-27-14)28-20(26)18-11(2)6-13(22)9-16(18)23/h4-10,22-23H,1-3H3/b5-4+/t21-/m1/s1
SMILES:	C/C=C/C1=CC2=CC(=O)[C@](C)(C(=O)C2=CO1)OC(=O)c1c(C)cc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823114
PubChem CID:	6451554
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003477] Azaphilones

*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
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2010354]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21879714]
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264170]
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26291474]
NPO33693	Talaromyces aculeatus DS-62013	Species	Trichocomaceae	Eukaryota	n.a.	saline-alkali soil, Shandong Province, China	2013-APR	PMID[28749670]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32293887]
NPO5411	Talaromyces austrocalifornicus	Species	Trichocomaceae	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	2
MIC	1

Activity Type	# Activity
Organism	2
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	>	200000.0	nM	PMID[559338]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	=	0.26	ug.mL-1	PMID[559340]
NPT20648	PROTEIN FAMILY	Alpha glucosidase	Homo sapiens	IC50	>	200000.0	nM	PMID[559340]

☑ 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 NPC84142 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	339
0.1-0.2	1553
0.2-0.3	3678
0.3-0.4	8191
0.4-0.5	10173
0.5-0.6	4166
0.6-0.7	6515
0.7-0.8	6830
0.8-0.85	1072
0.85-0.9	149
0.9-0.95	26
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC164762
0.9861	High Similarity	NPC91809
0.9527	High Similarity	NPC317585
0.9521	High Similarity	NPC472891
0.94	High Similarity	NPC472889
0.9396	High Similarity	NPC208173
0.9396	High Similarity	NPC170189
0.9396	High Similarity	NPC478221
0.9396	High Similarity	NPC472890
0.9392	High Similarity	NPC76041
0.9392	High Similarity	NPC115249
0.9392	High Similarity	NPC184284
0.9392	High Similarity	NPC478224
0.9329	High Similarity	NPC137301
0.9296	High Similarity	NPC52358
0.9272	High Similarity	NPC478225
0.9267	High Similarity	NPC69043
0.9267	High Similarity	NPC478230
0.9216	High Similarity	NPC317544
0.92	High Similarity	NPC478231
0.9167	High Similarity	NPC158634
0.9145	High Similarity	NPC246466
0.9091	High Similarity	NPC478200
0.9091	High Similarity	NPC33144
0.9041	High Similarity	NPC478202
0.9034	High Similarity	NPC472035
0.9034	High Similarity	NPC478201
0.9034	High Similarity	NPC244923
0.9028	High Similarity	NPC92655
0.9028	High Similarity	NPC268052
0.9028	High Similarity	NPC32360
0.902	High Similarity	NPC478226
0.8993	High Similarity	NPC73411
0.8993	High Similarity	NPC215711
0.8966	High Similarity	NPC156872
0.8958	High Similarity	NPC191835
0.8944	High Similarity	NPC175943
0.8933	High Similarity	NPC77325
0.8933	High Similarity	NPC4423
0.8926	High Similarity	NPC210320
0.8919	High Similarity	NPC472034
0.8904	High Similarity	NPC478217
0.8904	High Similarity	NPC53649
0.8904	High Similarity	NPC313123
0.8889	High Similarity	NPC70380
0.8873	High Similarity	NPC153783
0.8868	High Similarity	NPC328321
0.8859	High Similarity	NPC472033
0.8851	High Similarity	NPC475201
0.8851	High Similarity	NPC151607
0.8851	High Similarity	NPC42540
0.8851	High Similarity	NPC126882
0.8851	High Similarity	NPC210966
0.8851	High Similarity	NPC478203
0.8844	High Similarity	NPC474385
0.8836	High Similarity	NPC158472
0.8831	High Similarity	NPC472050
0.8828	High Similarity	NPC472602
0.8828	High Similarity	NPC177307
0.8828	High Similarity	NPC9121
0.8828	High Similarity	NPC212693
0.8828	High Similarity	NPC94248
0.8824	High Similarity	NPC471695
0.8819	High Similarity	NPC235115
0.8805	High Similarity	NPC283041
0.88	High Similarity	NPC259632
0.88	High Similarity	NPC472036
0.88	High Similarity	NPC52106
0.8797	High Similarity	NPC191930
0.8792	High Similarity	NPC257558
0.8792	High Similarity	NPC312789
0.8784	High Similarity	NPC472006
0.8784	High Similarity	NPC159721
0.8776	High Similarity	NPC475730
0.8776	High Similarity	NPC67650
0.8776	High Similarity	NPC472603
0.8776	High Similarity	NPC1704
0.8767	High Similarity	NPC247409
0.8759	High Similarity	NPC71256
0.8759	High Similarity	NPC135837
0.875	High Similarity	NPC56204
0.875	High Similarity	NPC158866
0.875	High Similarity	NPC295036
0.8742	High Similarity	NPC240253
0.8742	High Similarity	NPC240622
0.8742	High Similarity	NPC471642
0.8742	High Similarity	NPC20237
0.8742	High Similarity	NPC471641
0.8742	High Similarity	NPC37139
0.8734	High Similarity	NPC249181
0.8733	High Similarity	NPC51513
0.8733	High Similarity	NPC202112
0.8732	High Similarity	NPC219892
0.8732	High Similarity	NPC189823
0.8725	High Similarity	NPC277426
0.8725	High Similarity	NPC86373
0.8725	High Similarity	NPC280404
0.8725	High Similarity	NPC210425
0.8716	High Similarity	NPC250755
0.8707	High Similarity	NPC472600
0.8707	High Similarity	NPC49242
0.8707	High Similarity	NPC472601
0.8707	High Similarity	NPC155205
0.8701	High Similarity	NPC472799
0.8699	High Similarity	NPC472403
0.869	High Similarity	NPC50455
0.8684	High Similarity	NPC237440
0.8684	High Similarity	NPC270160
0.8658	High Similarity	NPC354984
0.8658	High Similarity	NPC471731
0.8658	High Similarity	NPC51106
0.8658	High Similarity	NPC469542
0.8649	High Similarity	NPC472605
0.8649	High Similarity	NPC472604
0.8645	High Similarity	NPC99381
0.8639	High Similarity	NPC25427
0.8639	High Similarity	NPC105456
0.8639	High Similarity	NPC295339
0.8639	High Similarity	NPC139634
0.863	High Similarity	NPC474771
0.863	High Similarity	NPC474849
0.863	High Similarity	NPC178467
0.863	High Similarity	NPC65837
0.863	High Similarity	NPC194579
0.863	High Similarity	NPC149372
0.8627	High Similarity	NPC150928
0.8621	High Similarity	NPC27407
0.8621	High Similarity	NPC180905
0.8621	High Similarity	NPC182496
0.8618	High Similarity	NPC2569
0.8618	High Similarity	NPC172329
0.8609	High Similarity	NPC473023
0.8609	High Similarity	NPC107625
0.8609	High Similarity	NPC163846
0.8609	High Similarity	NPC225173
0.86	High Similarity	NPC470216
0.86	High Similarity	NPC66404
0.86	High Similarity	NPC95123
0.8591	High Similarity	NPC49108
0.8591	High Similarity	NPC469579
0.8591	High Similarity	NPC471733
0.8591	High Similarity	NPC82913
0.8581	High Similarity	NPC210942
0.8581	High Similarity	NPC109007
0.8581	High Similarity	NPC169990
0.8581	High Similarity	NPC230902
0.8571	High Similarity	NPC475974
0.8571	High Similarity	NPC61590
0.8571	High Similarity	NPC46882
0.8571	High Similarity	NPC230848
0.8571	High Similarity	NPC132990
0.8562	High Similarity	NPC10027
0.8562	High Similarity	NPC476684
0.8562	High Similarity	NPC158481
0.8562	High Similarity	NPC474052
0.8562	High Similarity	NPC65775
0.8553	High Similarity	NPC473022
0.8553	High Similarity	NPC125801
0.8543	High Similarity	NPC474630
0.8543	High Similarity	NPC83272
0.8543	High Similarity	NPC28632
0.8543	High Similarity	NPC134621
0.8535	High Similarity	NPC263483
0.8533	High Similarity	NPC472610
0.8533	High Similarity	NPC215451
0.8533	High Similarity	NPC277369
0.8526	High Similarity	NPC56786
0.8526	High Similarity	NPC80534
0.8523	High Similarity	NPC90411
0.8523	High Similarity	NPC37530
0.8516	High Similarity	NPC470340
0.8516	High Similarity	NPC271681
0.8514	High Similarity	NPC88269
0.8506	High Similarity	NPC470107
0.8506	High Similarity	NPC85131
0.8503	High Similarity	NPC476333
0.8503	High Similarity	NPC472364
0.8503	High Similarity	NPC473391
0.8503	High Similarity	NPC301915
0.8503	High Similarity	NPC261292
0.8503	High Similarity	NPC472367
0.8497	Intermediate Similarity	NPC153417
0.8497	Intermediate Similarity	NPC221352
0.8497	Intermediate Similarity	NPC211811
0.8493	Intermediate Similarity	NPC142027
0.8491	Intermediate Similarity	NPC117985
0.8487	Intermediate Similarity	NPC196114
0.8487	Intermediate Similarity	NPC237208
0.8487	Intermediate Similarity	NPC153758
0.8487	Intermediate Similarity	NPC470570
0.8483	Intermediate Similarity	NPC43627
0.8481	Intermediate Similarity	NPC470339
0.8477	Intermediate Similarity	NPC193703
0.8477	Intermediate Similarity	NPC257025
0.8477	Intermediate Similarity	NPC184702
0.8477	Intermediate Similarity	NPC21599
0.8472	Intermediate Similarity	NPC198249
0.8472	Intermediate Similarity	NPC470831
0.8472	Intermediate Similarity	NPC214702
0.8467	Intermediate Similarity	NPC136840

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 NPC84142 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	960
0.2-0.3	1709
0.3-0.4	2598
0.4-0.5	1959
0.5-0.6	1104
0.6-0.7	374
0.7-0.8	136
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8767	High Similarity	NPD970	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7819	Suspended
0.8355	Intermediate Similarity	NPD6799	Approved
0.8311	Intermediate Similarity	NPD1510	Phase 2
0.8302	Intermediate Similarity	NPD7075	Discontinued
0.8301	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD2534	Approved
0.8301	Intermediate Similarity	NPD2532	Approved
0.8301	Intermediate Similarity	NPD2533	Approved
0.8291	Intermediate Similarity	NPD3817	Phase 2
0.8278	Intermediate Similarity	NPD3750	Approved
0.8269	Intermediate Similarity	NPD6599	Discontinued
0.8228	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD6801	Discontinued
0.8125	Intermediate Similarity	NPD3882	Suspended
0.8054	Intermediate Similarity	NPD1607	Approved
0.8041	Intermediate Similarity	NPD1240	Approved
0.8039	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1549	Phase 2
0.8013	Intermediate Similarity	NPD1512	Approved
0.8013	Intermediate Similarity	NPD2796	Approved
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7987	Intermediate Similarity	NPD7411	Suspended
0.7963	Intermediate Similarity	NPD3749	Approved
0.7962	Intermediate Similarity	NPD5403	Approved
0.7961	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7473	Discontinued
0.795	Intermediate Similarity	NPD5402	Approved
0.7949	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3748	Approved
0.7925	Intermediate Similarity	NPD4380	Phase 2
0.7895	Intermediate Similarity	NPD1551	Phase 2
0.7888	Intermediate Similarity	NPD2801	Approved
0.7888	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1511	Approved
0.7867	Intermediate Similarity	NPD230	Phase 1
0.7834	Intermediate Similarity	NPD5401	Approved
0.7829	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1934	Approved
0.7818	Intermediate Similarity	NPD6959	Discontinued
0.7806	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7765	Intermediate Similarity	NPD6797	Phase 2
0.7746	Intermediate Similarity	NPD9545	Approved
0.7744	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7251	Discontinued
0.7697	Intermediate Similarity	NPD919	Approved
0.7679	Intermediate Similarity	NPD6166	Phase 2
0.7679	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7808	Phase 3
0.7667	Intermediate Similarity	NPD3764	Approved
0.7667	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5710	Approved
0.7665	Intermediate Similarity	NPD5711	Approved
0.7662	Intermediate Similarity	NPD5406	Approved
0.7662	Intermediate Similarity	NPD5404	Approved
0.7662	Intermediate Similarity	NPD5408	Approved
0.7662	Intermediate Similarity	NPD5405	Approved
0.7658	Intermediate Similarity	NPD7390	Discontinued
0.7647	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5844	Phase 1
0.764	Intermediate Similarity	NPD3226	Approved
0.7628	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2800	Approved
0.7606	Intermediate Similarity	NPD9493	Approved
0.76	Intermediate Similarity	NPD8150	Discontinued
0.7588	Intermediate Similarity	NPD3818	Discontinued
0.7582	Intermediate Similarity	NPD6651	Approved
0.7576	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD943	Approved
0.7548	Intermediate Similarity	NPD6099	Approved
0.7548	Intermediate Similarity	NPD6100	Approved
0.7544	Intermediate Similarity	NPD7054	Approved
0.7532	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD1243	Approved
0.7516	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD7472	Approved
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.745	Intermediate Similarity	NPD1470	Approved
0.7415	Intermediate Similarity	NPD1201	Approved
0.7414	Intermediate Similarity	NPD6559	Discontinued
0.7399	Intermediate Similarity	NPD7074	Phase 3
0.7391	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2799	Discontinued
0.7365	Intermediate Similarity	NPD9717	Approved
0.7361	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5953	Discontinued
0.7356	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1465	Phase 2
0.7337	Intermediate Similarity	NPD5494	Approved
0.7333	Intermediate Similarity	NPD1203	Approved
0.732	Intermediate Similarity	NPD411	Approved
0.7312	Intermediate Similarity	NPD7435	Discontinued
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3926	Phase 2
0.7305	Intermediate Similarity	NPD4288	Approved
0.7303	Intermediate Similarity	NPD6832	Phase 2
0.7301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD422	Phase 1
0.7294	Intermediate Similarity	NPD1247	Approved
0.7285	Intermediate Similarity	NPD2798	Approved
0.7278	Intermediate Similarity	NPD2344	Approved
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.7261	Intermediate Similarity	NPD7033	Discontinued
0.7251	Intermediate Similarity	NPD3787	Discontinued
0.7241	Intermediate Similarity	NPD7286	Phase 2
0.7222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD2313	Discontinued
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.7181	Intermediate Similarity	NPD8319	Approved
0.7181	Intermediate Similarity	NPD8320	Phase 1
0.7179	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD447	Suspended
0.7178	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1471	Phase 3
0.716	Intermediate Similarity	NPD3300	Phase 2
0.716	Intermediate Similarity	NPD7236	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7158	Intermediate Similarity	NPD6535	Approved
0.7151	Intermediate Similarity	NPD6778	Approved
0.7151	Intermediate Similarity	NPD6781	Approved
0.7151	Intermediate Similarity	NPD6782	Approved
0.7151	Intermediate Similarity	NPD6780	Approved
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6779	Approved
0.7151	Intermediate Similarity	NPD6777	Approved
0.7151	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7133	Intermediate Similarity	NPD9269	Phase 2
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7108	Intermediate Similarity	NPD7458	Discontinued
0.7105	Intermediate Similarity	NPD1164	Approved
0.7105	Intermediate Similarity	NPD2797	Approved
0.7099	Intermediate Similarity	NPD2309	Approved
0.7095	Intermediate Similarity	NPD9268	Approved
0.7093	Intermediate Similarity	NPD7199	Phase 2
0.7086	Intermediate Similarity	NPD4749	Approved
0.7083	Intermediate Similarity	NPD37	Approved
0.7083	Intermediate Similarity	NPD7874	Approved
0.7083	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2654	Approved
0.7076	Intermediate Similarity	NPD6234	Discontinued
0.707	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5124	Phase 1
0.7069	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4967	Phase 2
0.7059	Intermediate Similarity	NPD4965	Approved
0.7059	Intermediate Similarity	NPD4966	Approved
0.7052	Intermediate Similarity	NPD7229	Phase 3
0.7047	Intermediate Similarity	NPD4626	Approved
0.7044	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7699	Phase 2
0.7043	Intermediate Similarity	NPD7700	Phase 2
0.7042	Intermediate Similarity	NPD74	Approved
0.7042	Intermediate Similarity	NPD9266	Approved
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7037	Intermediate Similarity	NPD7696	Phase 3
0.7037	Intermediate Similarity	NPD7698	Approved
0.7037	Intermediate Similarity	NPD7697	Approved
0.7033	Intermediate Similarity	NPD4287	Approved
0.7032	Intermediate Similarity	NPD4625	Phase 3
0.703	Intermediate Similarity	NPD6273	Approved
0.702	Intermediate Similarity	NPD1608	Approved
0.702	Intermediate Similarity	NPD3972	Approved
0.7014	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4307	Phase 2
0.7	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD7870	Phase 2
0.6989	Remote Similarity	NPD7177	Discontinued
0.6987	Remote Similarity	NPD6798	Discontinued
0.6987	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5691	Approved
0.6977	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9263	Approved
0.6972	Remote Similarity	NPD9267	Approved
0.6972	Remote Similarity	NPD9264	Approved
0.6972	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2403	Approved
0.6968	Remote Similarity	NPD4908	Phase 1
0.6962	Remote Similarity	NPD6355	Discontinued
0.6948	Remote Similarity	NPD1019	Discontinued
0.6946	Remote Similarity	NPD7239	Suspended

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