NPASS Compound

Structure

CID317544 OpenBabel06191716142D 30 32 0 0 1 0 0 0 0 0999 V2000 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 3.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 1.2679 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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2321 2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 2.1340 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 -4.7321 1.2679 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 -4.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 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 -5.2321 0.4019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2321 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 4.7321 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -2.2321 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 10 1 0 0 0 0 4 5 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 29 1 0 0 0 0 14 16 2 0 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 15 24 2 0 0 0 0 16 17 1 0 0 0 0 17 25 2 0 0 0 0 17 30 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 18 26 2 0 0 0 0 19 21 1 6 0 0 0 19 27 1 0 0 0 0 19 29 1 0 0 0 0 20 3 1 1 0 0 0 20 30 1 0 0 0 0 21 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.11
Volume:	401.487
LogP:	2.446
LogD:	2.005
LogS:	-3.674
# Rotatable Bonds:	4
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.417
Synthetic Accessibility Score:	4.694
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:	-5.331
MDCK Permeability:	1.857017559814267e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.552
Plasma Protein Binding (PPB):	91.62613677978516%
Volume Distribution (VD):	0.825
Pgp-substrate:	7.404660224914551%

ADMET: Metabolism

CYP1A2-inhibitor:	0.722
CYP1A2-substrate:	0.827
CYP2C19-inhibitor:	0.174
CYP2C19-substrate:	0.361
CYP2C9-inhibitor:	0.271
CYP2C9-substrate:	0.301
CYP2D6-inhibitor:	0.54
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.765
CYP3A4-substrate:	0.785

ADMET: Excretion

Clearance (CL):	1.837
Half-life (T1/2):	0.622

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.908
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.914
Rat Oral Acute Toxicity:	0.775
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.927
Carcinogencity:	0.792
Eye Corrosion:	0.004
Eye Irritation:	0.352
Respiratory Toxicity:	0.845

Download Data

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

Natural Product: NPC317544

Natural Product ID:	NPC317544
*Common Name:**	Purpurquinone A
IUPAC Name:	[(1S,7R,8aS)-1,8a-dihydroxy-7-methyl-6,8-dioxo-3-[(E)-prop-1-enyl]-1H-isochromen-7-yl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:	Purpurquinone A
Standard InCHIKey:	AWAFQUDYYMTSLY-QWOQCBQGSA-N
Standard InCHI:	InChI=1S/C21H20O9/c1-4-5-13-7-11-8-15(24)20(3,18(26)21(11,28)19(27)29-13)30-17(25)16-10(2)6-12(22)9-14(16)23/h4-9,19,22-23,27-28H,1-3H3/b5-4+/t19-,20+,21+/m0/s1
SMILES:	CC=CC1=CC2=CC(=O)C(C(=O)C2(C(O1)O)O)(C)OC(=O)C3=C(C=C(C=C3C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823108
PubChem CID:	54672171
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	>	200000.0	nM	PMID[572128]

☑ 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 NPC317544 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	362
0.1-0.2	1521
0.2-0.3	3671
0.3-0.4	8191
0.4-0.5	9720
0.5-0.6	4946
0.6-0.7	6248
0.7-0.8	7201
0.8-0.85	750
0.85-0.9	61
0.9-0.95	22
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9671	High Similarity	NPC317585
0.962	High Similarity	NPC328321
0.9419	High Similarity	NPC478226
0.9419	High Similarity	NPC472889
0.9416	High Similarity	NPC69043
0.9416	High Similarity	NPC208173
0.9416	High Similarity	NPC478230
0.9416	High Similarity	NPC170189
0.9412	High Similarity	NPC478224
0.9351	High Similarity	NPC137301
0.9351	High Similarity	NPC478231
0.9346	High Similarity	NPC91809
0.929	High Similarity	NPC478221
0.929	High Similarity	NPC472890
0.9286	High Similarity	NPC184284
0.9286	High Similarity	NPC76041
0.9286	High Similarity	NPC115249
0.9281	High Similarity	NPC164762
0.9281	High Similarity	NPC472891
0.9216	High Similarity	NPC84142
0.9172	High Similarity	NPC246466
0.9172	High Similarity	NPC478225
0.9074	High Similarity	NPC283041
0.9012	High Similarity	NPC20237
0.8951	High Similarity	NPC191930
0.8889	High Similarity	NPC249181
0.879	High Similarity	NPC56204
0.8742	High Similarity	NPC471695
0.8734	High Similarity	NPC70016
0.8734	High Similarity	NPC215921
0.8718	High Similarity	NPC210320
0.8712	High Similarity	NPC27942
0.8704	High Similarity	NPC472055
0.8696	High Similarity	NPC257309
0.8693	High Similarity	NPC244923
0.8693	High Similarity	NPC158634
0.8688	High Similarity	NPC99381
0.8684	High Similarity	NPC247409
0.8683	High Similarity	NPC190003
0.8683	High Similarity	NPC175107
0.8662	High Similarity	NPC215711
0.8662	High Similarity	NPC73411
0.8659	High Similarity	NPC121703
0.865	High Similarity	NPC117985
0.865	High Similarity	NPC129217
0.865	High Similarity	NPC224530
0.865	High Similarity	NPC259957
0.865	High Similarity	NPC216496
0.865	High Similarity	NPC159579
0.865	High Similarity	NPC48093
0.865	High Similarity	NPC282169
0.865	High Similarity	NPC85707
0.8642	High Similarity	NPC470339
0.8642	High Similarity	NPC279732
0.8634	High Similarity	NPC472050
0.8631	High Similarity	NPC4390
0.8627	High Similarity	NPC158472
0.8623	High Similarity	NPC244776
0.8623	High Similarity	NPC20505
0.8623	High Similarity	NPC116864
0.8623	High Similarity	NPC235260
0.8623	High Similarity	NPC155763
0.8616	High Similarity	NPC200773
0.8616	High Similarity	NPC240768
0.8608	High Similarity	NPC77325
0.8608	High Similarity	NPC237440
0.8608	High Similarity	NPC4423
0.8608	High Similarity	NPC270160
0.8606	High Similarity	NPC470735
0.8606	High Similarity	NPC72016
0.8606	High Similarity	NPC329647
0.8606	High Similarity	NPC294722
0.859	High Similarity	NPC83272
0.858	High Similarity	NPC264735
0.8571	High Similarity	NPC153755
0.8563	High Similarity	NPC476771
0.8563	High Similarity	NPC473095
0.8563	High Similarity	NPC138927
0.8563	High Similarity	NPC473096
0.8562	High Similarity	NPC52358
0.8562	High Similarity	NPC32360
0.8562	High Similarity	NPC268052
0.8553	High Similarity	NPC475407
0.8553	High Similarity	NPC469619
0.8553	High Similarity	NPC469670
0.8537	High Similarity	NPC69868
0.8537	High Similarity	NPC474779
0.8529	High Similarity	NPC472385
0.8529	High Similarity	NPC198324
0.8528	High Similarity	NPC111929
0.8528	High Similarity	NPC104677
0.8528	High Similarity	NPC41121
0.8528	High Similarity	NPC320283
0.8528	High Similarity	NPC472459
0.8526	High Similarity	NPC210425
0.8526	High Similarity	NPC280404
0.8526	High Similarity	NPC277426
0.8526	High Similarity	NPC86373
0.8521	High Similarity	NPC472054
0.8519	High Similarity	NPC272550
0.8516	High Similarity	NPC82913
0.8512	High Similarity	NPC470580
0.8512	High Similarity	NPC298778
0.8509	High Similarity	NPC155686
0.8503	High Similarity	NPC317489
0.8503	High Similarity	NPC84362
0.8503	High Similarity	NPC223424
0.8503	High Similarity	NPC173637
0.8503	High Similarity	NPC473094
0.8503	High Similarity	NPC52550
0.8503	High Similarity	NPC127546
0.85	High Similarity	NPC205918
0.8497	Intermediate Similarity	NPC478200
0.8497	Intermediate Similarity	NPC33144
0.8494	Intermediate Similarity	NPC472049
0.8494	Intermediate Similarity	NPC478026
0.8494	Intermediate Similarity	NPC7752
0.8494	Intermediate Similarity	NPC475979
0.8485	Intermediate Similarity	NPC474763
0.8485	Intermediate Similarity	NPC150164
0.8481	Intermediate Similarity	NPC52106
0.8481	Intermediate Similarity	NPC471734
0.848	Intermediate Similarity	NPC35167
0.8476	Intermediate Similarity	NPC470358
0.8476	Intermediate Similarity	NPC243701
0.8471	Intermediate Similarity	NPC470454
0.8471	Intermediate Similarity	NPC253685
0.8471	Intermediate Similarity	NPC101191
0.8471	Intermediate Similarity	NPC470583
0.8471	Intermediate Similarity	NPC210094
0.8471	Intermediate Similarity	NPC49344
0.8471	Intermediate Similarity	NPC115760
0.8471	Intermediate Similarity	NPC19056
0.8471	Intermediate Similarity	NPC68381
0.8471	Intermediate Similarity	NPC43211
0.8471	Intermediate Similarity	NPC171706
0.8471	Intermediate Similarity	NPC237435
0.8471	Intermediate Similarity	NPC135277
0.8471	Intermediate Similarity	NPC477848
0.8471	Intermediate Similarity	NPC199533
0.8466	Intermediate Similarity	NPC133671
0.8466	Intermediate Similarity	NPC78263
0.8466	Intermediate Similarity	NPC77672
0.8466	Intermediate Similarity	NPC6985
0.8466	Intermediate Similarity	NPC208651
0.8466	Intermediate Similarity	NPC182634
0.8466	Intermediate Similarity	NPC197304
0.8466	Intermediate Similarity	NPC288084
0.8466	Intermediate Similarity	NPC54802
0.8466	Intermediate Similarity	NPC135391
0.8466	Intermediate Similarity	NPC108831
0.8466	Intermediate Similarity	NPC206641
0.8462	Intermediate Similarity	NPC476772
0.8462	Intermediate Similarity	NPC245452
0.8462	Intermediate Similarity	NPC478202
0.8457	Intermediate Similarity	NPC471456
0.8457	Intermediate Similarity	NPC473241
0.8452	Intermediate Similarity	NPC203050
0.8452	Intermediate Similarity	NPC120099
0.8452	Intermediate Similarity	NPC223747
0.8452	Intermediate Similarity	NPC259905
0.8452	Intermediate Similarity	NPC222455
0.8452	Intermediate Similarity	NPC219904
0.8452	Intermediate Similarity	NPC225434
0.8447	Intermediate Similarity	NPC470340
0.8443	Intermediate Similarity	NPC179950
0.8443	Intermediate Similarity	NPC88789
0.8443	Intermediate Similarity	NPC328940
0.8443	Intermediate Similarity	NPC113968
0.8443	Intermediate Similarity	NPC118284
0.8443	Intermediate Similarity	NPC253662
0.8443	Intermediate Similarity	NPC277174
0.8443	Intermediate Similarity	NPC56077
0.8443	Intermediate Similarity	NPC178851
0.8443	Intermediate Similarity	NPC73855
0.8443	Intermediate Similarity	NPC67037
0.8443	Intermediate Similarity	NPC255615
0.8443	Intermediate Similarity	NPC274618
0.8443	Intermediate Similarity	NPC64425
0.8443	Intermediate Similarity	NPC135599
0.8443	Intermediate Similarity	NPC281131
0.8443	Intermediate Similarity	NPC308404
0.8443	Intermediate Similarity	NPC276222
0.8443	Intermediate Similarity	NPC145038
0.8438	Intermediate Similarity	NPC191154
0.8434	Intermediate Similarity	NPC179198
0.8434	Intermediate Similarity	NPC327809
0.8434	Intermediate Similarity	NPC278419
0.8434	Intermediate Similarity	NPC183672
0.8434	Intermediate Similarity	NPC66087
0.8434	Intermediate Similarity	NPC317781
0.8424	Intermediate Similarity	NPC181465
0.8424	Intermediate Similarity	NPC473438
0.8424	Intermediate Similarity	NPC276377
0.8424	Intermediate Similarity	NPC476215
0.8424	Intermediate Similarity	NPC265885
0.8424	Intermediate Similarity	NPC215710
0.8424	Intermediate Similarity	NPC249281
0.8424	Intermediate Similarity	NPC163242
0.8424	Intermediate Similarity	NPC116458

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 NPC317544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	931
0.2-0.3	1939
0.3-0.4	2694
0.4-0.5	1871
0.5-0.6	934
0.6-0.7	327
0.7-0.8	134
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD6797	Phase 2
0.8344	Intermediate Similarity	NPD3817	Phase 2
0.8304	Intermediate Similarity	NPD7251	Discontinued
0.8295	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7808	Phase 3
0.8242	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3818	Discontinued
0.8133	Intermediate Similarity	NPD7075	Discontinued
0.8129	Intermediate Similarity	NPD7054	Approved
0.8121	Intermediate Similarity	NPD5402	Approved
0.811	Intermediate Similarity	NPD6801	Discontinued
0.8081	Intermediate Similarity	NPD7472	Approved
0.8063	Intermediate Similarity	NPD6799	Approved
0.8047	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD2532	Approved
0.8012	Intermediate Similarity	NPD2533	Approved
0.8012	Intermediate Similarity	NPD2534	Approved
0.8012	Intermediate Similarity	NPD7473	Discontinued
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD4380	Phase 2
0.7977	Intermediate Similarity	NPD7074	Phase 3
0.7964	Intermediate Similarity	NPD3882	Suspended
0.7952	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7819	Suspended
0.7952	Intermediate Similarity	NPD2801	Approved
0.7914	Intermediate Similarity	NPD5403	Approved
0.7901	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6559	Discontinued
0.7875	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1512	Approved
0.7849	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7435	Discontinued
0.7849	Intermediate Similarity	NPD6166	Phase 2
0.7849	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5401	Approved
0.7784	Intermediate Similarity	NPD1934	Approved
0.7765	Intermediate Similarity	NPD8150	Discontinued
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7738	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1511	Approved
0.7716	Intermediate Similarity	NPD6190	Approved
0.7713	Intermediate Similarity	NPD8320	Phase 1
0.7713	Intermediate Similarity	NPD8319	Approved
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7705	Intermediate Similarity	NPD6534	Approved
0.7705	Intermediate Similarity	NPD6535	Approved
0.7688	Intermediate Similarity	NPD6776	Approved
0.7688	Intermediate Similarity	NPD6782	Approved
0.7688	Intermediate Similarity	NPD6779	Approved
0.7688	Intermediate Similarity	NPD6781	Approved
0.7688	Intermediate Similarity	NPD6778	Approved
0.7688	Intermediate Similarity	NPD6777	Approved
0.7688	Intermediate Similarity	NPD6780	Approved
0.7673	Intermediate Similarity	NPD1510	Phase 2
0.7673	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3750	Approved
0.7647	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3787	Discontinued
0.7604	Intermediate Similarity	NPD7874	Approved
0.7604	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8312	Approved
0.7598	Intermediate Similarity	NPD8313	Approved
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7700	Phase 2
0.7581	Intermediate Similarity	NPD7699	Phase 2
0.7574	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD6959	Discontinued
0.7558	Intermediate Similarity	NPD6234	Discontinued
0.7544	Intermediate Similarity	NPD4965	Approved
0.7544	Intermediate Similarity	NPD4966	Approved
0.7544	Intermediate Similarity	NPD4967	Phase 2
0.7528	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7411	Suspended
0.7514	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD3749	Approved
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7697	Approved
0.7474	Intermediate Similarity	NPD7698	Approved
0.7474	Intermediate Similarity	NPD7696	Phase 3
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.747	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD8151	Discontinued
0.7458	Intermediate Similarity	NPD7228	Approved
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1607	Approved
0.7435	Intermediate Similarity	NPD7871	Phase 2
0.7435	Intermediate Similarity	NPD7870	Phase 2
0.7429	Intermediate Similarity	NPD5711	Approved
0.7429	Intermediate Similarity	NPD5710	Approved
0.7427	Intermediate Similarity	NPD1465	Phase 2
0.7423	Intermediate Similarity	NPD1549	Phase 2
0.7421	Intermediate Similarity	NPD1240	Approved
0.7418	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7390	Discontinued
0.7409	Intermediate Similarity	NPD7701	Phase 2
0.7407	Intermediate Similarity	NPD2796	Approved
0.7396	Intermediate Similarity	NPD3226	Approved
0.7389	Intermediate Similarity	NPD7685	Pre-registration
0.7384	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2800	Approved
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7356	Intermediate Similarity	NPD919	Approved
0.7346	Intermediate Similarity	NPD3748	Approved
0.7345	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1653	Approved
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7312	Intermediate Similarity	NPD943	Approved
0.7301	Intermediate Similarity	NPD2935	Discontinued
0.7301	Intermediate Similarity	NPD1551	Phase 2
0.7296	Intermediate Similarity	NPD7783	Phase 2
0.7296	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7801	Approved
0.7241	Intermediate Similarity	NPD7768	Phase 2
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7229	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6651	Approved
0.7216	Intermediate Similarity	NPD5494	Approved
0.7191	Intermediate Similarity	NPD3926	Phase 2
0.7188	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3764	Approved
0.7181	Intermediate Similarity	NPD6212	Phase 3
0.7181	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6213	Phase 3
0.7176	Intermediate Similarity	NPD920	Approved
0.7175	Intermediate Similarity	NPD1247	Approved
0.7167	Intermediate Similarity	NPD7799	Discontinued
0.7158	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.7128	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD9545	Approved
0.7104	Intermediate Similarity	NPD8368	Discontinued
0.7104	Intermediate Similarity	NPD7240	Approved
0.7101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7091	Intermediate Similarity	NPD6100	Approved
0.7091	Intermediate Similarity	NPD5405	Approved
0.7091	Intermediate Similarity	NPD5404	Approved
0.7091	Intermediate Similarity	NPD5408	Approved
0.7091	Intermediate Similarity	NPD5406	Approved
0.7091	Intermediate Similarity	NPD6099	Approved
0.7066	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD447	Suspended
0.7049	Intermediate Similarity	NPD5953	Discontinued
0.7041	Intermediate Similarity	NPD3300	Phase 2
0.7006	Intermediate Similarity	NPD9269	Phase 2
0.7005	Intermediate Similarity	NPD7584	Approved
0.6994	Remote Similarity	NPD4060	Phase 1
0.6993	Remote Similarity	NPD9493	Approved
0.6989	Remote Similarity	NPD8407	Phase 2
0.6981	Remote Similarity	NPD1470	Approved
0.6966	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1243	Approved
0.6961	Remote Similarity	NPD2403	Approved
0.6959	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1201	Approved
0.6941	Remote Similarity	NPD643	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7286	Phase 2
0.6937	Remote Similarity	NPD2798	Approved
0.6932	Remote Similarity	NPD8455	Phase 2
0.6931	Remote Similarity	NPD7930	Approved
0.6928	Remote Similarity	NPD2799	Discontinued
0.6928	Remote Similarity	NPD7033	Discontinued
0.689	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6798	Discontinued
0.6871	Remote Similarity	NPD2313	Discontinued
0.6868	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1652	Phase 2
0.686	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD9268	Approved
0.6852	Remote Similarity	NPD6832	Phase 2
0.6851	Remote Similarity	NPD7229	Phase 3
0.6848	Remote Similarity	NPD6355	Discontinued
0.6845	Remote Similarity	NPD2344	Approved
0.6842	Remote Similarity	NPD8361	Approved
0.6842	Remote Similarity	NPD8435	Approved
0.6842	Remote Similarity	NPD8360	Approved
0.6842	Remote Similarity	NPD7236	Approved
0.6835	Remote Similarity	NPD422	Phase 1
0.6829	Remote Similarity	NPD6233	Phase 2
0.6827	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8166	Discontinued
0.6812	Remote Similarity	NPD8366	Approved
0.68	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7585	Approved
0.6798	Remote Similarity	NPD4288	Approved
0.6792	Remote Similarity	NPD9717	Approved
0.6786	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1203	Approved
0.6768	Remote Similarity	NPD411	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