NPASS Compound

Structure

CID317585 OpenBabel06191716142D 29 31 0 0 1 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 0.0000 C 0 0 0 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8660 -0.2321 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3660 0.6340 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 -2.3660 0.6340 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 -3.8660 -0.2321 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 -3.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 2.3660 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 -0.8660 1.5000 0.0000 C 0 0 1 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 -4.3660 -1.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3660 2.3660 0.0000 O 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 -2.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -1.3660 2.3660 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 16 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 10 28 1 0 0 0 0 11 17 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 28 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 17 18 1 0 0 0 0 18 25 2 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 20 3 1 1 0 0 0 20 29 1 0 0 0 0 21 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.12
Volume:	392.696
LogP:	2.825
LogD:	2.487
LogS:	-4.017
# Rotatable Bonds:	4
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.515
Synthetic Accessibility Score:	4.488
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.122
MDCK Permeability:	2.0020879674120806e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.691

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.736
Plasma Protein Binding (PPB):	91.50313568115234%
Volume Distribution (VD):	0.911
Pgp-substrate:	8.981328010559082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.458
CYP2C19-substrate:	0.453
CYP2C9-inhibitor:	0.57
CYP2C9-substrate:	0.339
CYP2D6-inhibitor:	0.658
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	2.86
Half-life (T1/2):	0.488

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.856
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.886
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.913
Carcinogencity:	0.631
Eye Corrosion:	0.01
Eye Irritation:	0.79
Respiratory Toxicity:	0.718

Download Data

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

Natural Product: NPC317585

Natural Product ID:	NPC317585
*Common Name:**	[(7R,8As)-8A-Hydroxy-7-Methyl-6,8-Dioxo-3-[(E)-Prop-1-Enyl]-1H-Isochromen-7-Yl] 2,4-Dihydroxy-6-Methylbenzoate
IUPAC Name:	[(7R,8aS)-8a-hydroxy-7-methyl-6,8-dioxo-3-[(E)-prop-1-enyl]-1H-isochromen-7-yl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:
Standard InCHIKey:	MZHBZSGFVGKNQP-QLAYCGNHSA-N
Standard InCHI:	InChI=1S/C21H20O8/c1-4-5-14-7-12-8-16(24)20(3,19(26)21(12,27)10-28-14)29-18(25)17-11(2)6-13(22)9-15(17)23/h4-9,22-23,27H,10H2,1-3H3/b5-4+/t20-,21-/m1/s1
SMILES:	C/C=C/C1=CC2=CC(=O)[C@@](C(=O)[C@]2(CO1)O)(C)OC(=O)c1c(C)cc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823110
PubChem CID:	54672239
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]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32293887]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	64000.0	nM	PMID[566104]

☑ 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 NPC317585 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	361
0.1-0.2	1463
0.2-0.3	3724
0.3-0.4	8061
0.4-0.5	9869
0.5-0.6	4559
0.6-0.7	6272
0.7-0.8	7260
0.8-0.85	973
0.85-0.9	126
0.9-0.95	10
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9671	High Similarity	NPC317544
0.9664	High Similarity	NPC137301
0.9664	High Similarity	NPC478231
0.9603	High Similarity	NPC472889
0.96	High Similarity	NPC208173
0.96	High Similarity	NPC478230
0.96	High Similarity	NPC472890
0.96	High Similarity	NPC478221
0.96	High Similarity	NPC69043
0.96	High Similarity	NPC170189
0.9597	High Similarity	NPC184284
0.9597	High Similarity	NPC478224
0.9597	High Similarity	NPC115249
0.9597	High Similarity	NPC76041
0.9595	High Similarity	NPC472891
0.9595	High Similarity	NPC164762
0.953	High Similarity	NPC91809
0.9527	High Similarity	NPC84142
0.9474	High Similarity	NPC478225
0.9346	High Similarity	NPC478226
0.9346	High Similarity	NPC246466
0.9304	High Similarity	NPC328321
0.9241	High Similarity	NPC283041
0.9236	High Similarity	NPC191930
0.9177	High Similarity	NPC20237
0.9172	High Similarity	NPC249181
0.8954	High Similarity	NPC56204
0.891	High Similarity	NPC472050
0.8903	High Similarity	NPC471695
0.8896	High Similarity	NPC70016
0.8896	High Similarity	NPC215921
0.8882	High Similarity	NPC210320
0.8861	High Similarity	NPC472055
0.8859	High Similarity	NPC244923
0.8859	High Similarity	NPC158634
0.8851	High Similarity	NPC247409
0.8851	High Similarity	NPC52358
0.8846	High Similarity	NPC99381
0.8824	High Similarity	NPC215711
0.8824	High Similarity	NPC73411
0.8805	High Similarity	NPC117985
0.8797	High Similarity	NPC470339
0.8792	High Similarity	NPC158472
0.8784	High Similarity	NPC478200
0.8784	High Similarity	NPC33144
0.8774	High Similarity	NPC200773
0.8774	High Similarity	NPC240768
0.8766	High Similarity	NPC270160
0.8766	High Similarity	NPC4423
0.8766	High Similarity	NPC77325
0.8766	High Similarity	NPC237440
0.8758	High Similarity	NPC52106
0.875	High Similarity	NPC83272
0.8742	High Similarity	NPC478202
0.8742	High Similarity	NPC243701
0.8726	High Similarity	NPC471456
0.8725	High Similarity	NPC268052
0.8725	High Similarity	NPC32360
0.8712	High Similarity	NPC473095
0.8712	High Similarity	NPC473096
0.871	High Similarity	NPC469619
0.871	High Similarity	NPC469670
0.8684	High Similarity	NPC210425
0.8684	High Similarity	NPC86373
0.8684	High Similarity	NPC277426
0.8684	High Similarity	NPC280404
0.8675	High Similarity	NPC322112
0.8675	High Similarity	NPC82913
0.8667	High Similarity	NPC156872
0.8662	High Similarity	NPC155686
0.8662	High Similarity	NPC192189
0.8658	High Similarity	NPC191835
0.8654	High Similarity	NPC205918
0.865	High Similarity	NPC473094
0.8645	High Similarity	NPC280753
0.8645	High Similarity	NPC44378
0.8642	High Similarity	NPC472049
0.8639	High Similarity	NPC175943
0.8636	High Similarity	NPC259632
0.8618	High Similarity	NPC472006
0.8609	High Similarity	NPC478201
0.8609	High Similarity	NPC313123
0.8609	High Similarity	NPC472035
0.8609	High Similarity	NPC478217
0.8609	High Similarity	NPC53649
0.8608	High Similarity	NPC473241
0.8608	High Similarity	NPC80534
0.8608	High Similarity	NPC56786
0.86	High Similarity	NPC92655
0.8599	High Similarity	NPC470340
0.8591	High Similarity	NPC70380
0.859	High Similarity	NPC295036
0.8581	High Similarity	NPC94781
0.8571	High Similarity	NPC202112
0.8571	High Similarity	NPC473023
0.8571	High Similarity	NPC260946
0.8571	High Similarity	NPC107625
0.8571	High Similarity	NPC153783
0.8571	High Similarity	NPC51513
0.8571	High Similarity	NPC112418
0.8571	High Similarity	NPC472033
0.8562	High Similarity	NPC478203
0.8562	High Similarity	NPC475201
0.8562	High Similarity	NPC103910
0.8562	High Similarity	NPC257025
0.8562	High Similarity	NPC42540
0.8562	High Similarity	NPC210966
0.8562	High Similarity	NPC126882
0.8562	High Similarity	NPC151607
0.8553	High Similarity	NPC478027
0.8553	High Similarity	NPC474385
0.8544	High Similarity	NPC281703
0.8544	High Similarity	NPC125487
0.8535	High Similarity	NPC46882
0.8535	High Similarity	NPC132990
0.8535	High Similarity	NPC471229
0.8533	High Similarity	NPC472602
0.8533	High Similarity	NPC126739
0.8533	High Similarity	NPC94248
0.8533	High Similarity	NPC197666
0.8533	High Similarity	NPC212693
0.8526	High Similarity	NPC277032
0.8526	High Similarity	NPC120171
0.8523	High Similarity	NPC235115
0.8519	High Similarity	NPC471745
0.8516	High Similarity	NPC81835
0.8516	High Similarity	NPC166583
0.8516	High Similarity	NPC53362
0.8516	High Similarity	NPC472036
0.8509	High Similarity	NPC471744
0.8506	High Similarity	NPC257558
0.8506	High Similarity	NPC312789
0.8506	High Similarity	NPC472034
0.85	High Similarity	NPC263483
0.85	High Similarity	NPC473395
0.8497	Intermediate Similarity	NPC51106
0.8497	Intermediate Similarity	NPC159721
0.8497	Intermediate Similarity	NPC354984
0.8494	Intermediate Similarity	NPC473113
0.8491	Intermediate Similarity	NPC16082
0.8491	Intermediate Similarity	NPC16286
0.8491	Intermediate Similarity	NPC237560
0.8491	Intermediate Similarity	NPC68727
0.8491	Intermediate Similarity	NPC82592
0.8491	Intermediate Similarity	NPC476169
0.8491	Intermediate Similarity	NPC79998
0.8487	Intermediate Similarity	NPC472603
0.8487	Intermediate Similarity	NPC90411
0.8487	Intermediate Similarity	NPC1704
0.8487	Intermediate Similarity	NPC475730
0.8487	Intermediate Similarity	NPC67650
0.8481	Intermediate Similarity	NPC470337
0.8481	Intermediate Similarity	NPC161159
0.8481	Intermediate Similarity	NPC470338
0.8481	Intermediate Similarity	NPC271681
0.8481	Intermediate Similarity	NPC167903
0.8481	Intermediate Similarity	NPC268992
0.8481	Intermediate Similarity	NPC210597
0.8481	Intermediate Similarity	NPC51824
0.8481	Intermediate Similarity	NPC113608
0.8477	Intermediate Similarity	NPC471819
0.8471	Intermediate Similarity	NPC267117
0.8471	Intermediate Similarity	NPC158866
0.8471	Intermediate Similarity	NPC179178
0.8467	Intermediate Similarity	NPC71256
0.8467	Intermediate Similarity	NPC135837
0.8462	Intermediate Similarity	NPC240622
0.8462	Intermediate Similarity	NPC172329
0.8462	Intermediate Similarity	NPC37139
0.8462	Intermediate Similarity	NPC2569
0.8462	Intermediate Similarity	NPC471641
0.8462	Intermediate Similarity	NPC471642
0.8462	Intermediate Similarity	NPC240253
0.8452	Intermediate Similarity	NPC153758
0.8447	Intermediate Similarity	NPC105242
0.8447	Intermediate Similarity	NPC253634
0.8447	Intermediate Similarity	NPC18772
0.8447	Intermediate Similarity	NPC25495
0.8447	Intermediate Similarity	NPC9609
0.8447	Intermediate Similarity	NPC19687
0.8447	Intermediate Similarity	NPC261004
0.8447	Intermediate Similarity	NPC176300
0.8447	Intermediate Similarity	NPC18607
0.8447	Intermediate Similarity	NPC130894
0.8447	Intermediate Similarity	NPC280680
0.8447	Intermediate Similarity	NPC300943
0.8447	Intermediate Similarity	NPC143828
0.8447	Intermediate Similarity	NPC191459
0.8447	Intermediate Similarity	NPC204854
0.8447	Intermediate Similarity	NPC22472
0.8447	Intermediate Similarity	NPC152166
0.8447	Intermediate Similarity	NPC477410
0.8447	Intermediate Similarity	NPC7846
0.8447	Intermediate Similarity	NPC288669
0.8447	Intermediate Similarity	NPC115798
0.8447	Intermediate Similarity	NPC4481
0.8442	Intermediate Similarity	NPC470216
0.8438	Intermediate Similarity	NPC178854
0.8438	Intermediate Similarity	NPC265511
0.8438	Intermediate Similarity	NPC153512

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 NPC317585 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	899
0.2-0.3	1847
0.3-0.4	2666
0.4-0.5	1895
0.5-0.6	1002
0.6-0.7	375
0.7-0.8	141
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8608	High Similarity	NPD3817	Phase 2
0.8477	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7075	Discontinued
0.8323	Intermediate Similarity	NPD6799	Approved
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.8269	Intermediate Similarity	NPD2534	Approved
0.8269	Intermediate Similarity	NPD2532	Approved
0.8269	Intermediate Similarity	NPD2533	Approved
0.8261	Intermediate Similarity	NPD5402	Approved
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.825	Intermediate Similarity	NPD6801	Discontinued
0.8239	Intermediate Similarity	NPD6599	Discontinued
0.821	Intermediate Similarity	NPD3882	Suspended
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD2801	Approved
0.8199	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4380	Phase 2
0.8101	Intermediate Similarity	NPD1512	Approved
0.8059	Intermediate Similarity	NPD6797	Phase 2
0.805	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD1934	Approved
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6166	Phase 2
0.7976	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1511	Approved
0.7965	Intermediate Similarity	NPD7808	Phase 3
0.7961	Intermediate Similarity	NPD230	Phase 1
0.7941	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5401	Approved
0.7922	Intermediate Similarity	NPD1510	Phase 2
0.7922	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3750	Approved
0.7886	Intermediate Similarity	NPD8150	Discontinued
0.7882	Intermediate Similarity	NPD3818	Discontinued
0.7879	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6190	Approved
0.7836	Intermediate Similarity	NPD7054	Approved
0.7798	Intermediate Similarity	NPD6959	Discontinued
0.7791	Intermediate Similarity	NPD7472	Approved
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7411	Suspended
0.7725	Intermediate Similarity	NPD3749	Approved
0.7707	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7074	Phase 3
0.7677	Intermediate Similarity	NPD1607	Approved
0.7674	Intermediate Similarity	NPD3751	Discontinued
0.7662	Intermediate Similarity	NPD1240	Approved
0.7658	Intermediate Similarity	NPD1549	Phase 2
0.7651	Intermediate Similarity	NPD1465	Phase 2
0.7647	Intermediate Similarity	NPD5711	Approved
0.7647	Intermediate Similarity	NPD5710	Approved
0.7644	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2796	Approved
0.764	Intermediate Similarity	NPD7390	Discontinued
0.763	Intermediate Similarity	NPD5844	Phase 1
0.7622	Intermediate Similarity	NPD3226	Approved
0.761	Intermediate Similarity	NPD2800	Approved
0.7605	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6559	Discontinued
0.7581	Intermediate Similarity	NPD7435	Discontinued
0.758	Intermediate Similarity	NPD3748	Approved
0.7574	Intermediate Similarity	NPD919	Approved
0.7558	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD943	Approved
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7471	Intermediate Similarity	NPD6234	Discontinued
0.7456	Intermediate Similarity	NPD7768	Phase 2
0.7453	Intermediate Similarity	NPD4628	Phase 3
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6651	Approved
0.7447	Intermediate Similarity	NPD8320	Phase 1
0.7447	Intermediate Similarity	NPD8319	Approved
0.7432	Intermediate Similarity	NPD6534	Approved
0.7432	Intermediate Similarity	NPD6535	Approved
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5494	Approved
0.7419	Intermediate Similarity	NPD6782	Approved
0.7419	Intermediate Similarity	NPD6778	Approved
0.7419	Intermediate Similarity	NPD6777	Approved
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6776	Approved
0.7419	Intermediate Similarity	NPD6779	Approved
0.7419	Intermediate Similarity	NPD3764	Approved
0.7419	Intermediate Similarity	NPD6780	Approved
0.7419	Intermediate Similarity	NPD6781	Approved
0.7399	Intermediate Similarity	NPD3926	Phase 2
0.7394	Intermediate Similarity	NPD920	Approved
0.7384	Intermediate Similarity	NPD1247	Approved
0.7381	Intermediate Similarity	NPD37	Approved
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7365	Intermediate Similarity	NPD9545	Approved
0.7353	Intermediate Similarity	NPD4966	Approved
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD4965	Approved
0.7344	Intermediate Similarity	NPD7874	Approved
0.7344	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD5404	Approved
0.7312	Intermediate Similarity	NPD6100	Approved
0.7312	Intermediate Similarity	NPD6099	Approved
0.7312	Intermediate Similarity	NPD7699	Phase 2
0.7312	Intermediate Similarity	NPD5406	Approved
0.7312	Intermediate Similarity	NPD5405	Approved
0.7312	Intermediate Similarity	NPD7700	Phase 2
0.7312	Intermediate Similarity	NPD5408	Approved
0.7289	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7199	Phase 2
0.7278	Intermediate Similarity	NPD447	Suspended
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3300	Phase 2
0.7247	Intermediate Similarity	NPD5953	Discontinued
0.7237	Intermediate Similarity	NPD9269	Phase 2
0.723	Intermediate Similarity	NPD9493	Approved
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7211	Intermediate Similarity	NPD7696	Phase 3
0.7211	Intermediate Similarity	NPD7698	Approved
0.7211	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD1470	Approved
0.7202	Intermediate Similarity	NPD8151	Discontinued
0.7178	Intermediate Similarity	NPD1243	Approved
0.7175	Intermediate Similarity	NPD7228	Approved
0.7173	Intermediate Similarity	NPD7871	Phase 2
0.7173	Intermediate Similarity	NPD7870	Phase 2
0.7171	Intermediate Similarity	NPD1201	Approved
0.7169	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2403	Approved
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7135	Intermediate Similarity	NPD7286	Phase 2
0.7114	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7685	Pre-registration
0.7089	Intermediate Similarity	NPD2313	Discontinued
0.7089	Intermediate Similarity	NPD6798	Discontinued
0.7086	Intermediate Similarity	NPD9268	Approved
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7062	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7055	Intermediate Similarity	NPD2344	Approved
0.7045	Intermediate Similarity	NPD7229	Phase 3
0.7044	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD7783	Phase 2
0.7041	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1653	Approved
0.7041	Intermediate Similarity	NPD7801	Approved
0.7037	Intermediate Similarity	NPD7033	Discontinued
0.703	Intermediate Similarity	NPD8166	Discontinued
0.7017	Intermediate Similarity	NPD8368	Discontinued
0.7013	Intermediate Similarity	NPD9717	Approved
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6994	Remote Similarity	NPD4288	Approved
0.6987	Remote Similarity	NPD1203	Approved
0.6981	Remote Similarity	NPD411	Approved
0.6981	Remote Similarity	NPD3268	Approved
0.698	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6823	Phase 2
0.6978	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1652	Phase 2
0.6964	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1471	Phase 3
0.6946	Remote Similarity	NPD7236	Approved
0.6943	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4308	Phase 3
0.6918	Remote Similarity	NPD7095	Approved
0.6915	Remote Similarity	NPD6212	Phase 3
0.6915	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6213	Phase 3
0.691	Remote Similarity	NPD5242	Approved
0.6902	Remote Similarity	NPD8407	Phase 2
0.6901	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD9494	Approved
0.6897	Remote Similarity	NPD5353	Approved
0.6889	Remote Similarity	NPD7799	Discontinued
0.6886	Remote Similarity	NPD2309	Approved
0.6886	Remote Similarity	NPD2354	Approved
0.6879	Remote Similarity	NPD2797	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