NPASS Compound

Structure

CID328321 OpenBabel06191716202D 31 33 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 -5.2321 3.8660 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 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 -3.7321 1.2679 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 -0.0000 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 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 -4.7321 1.2679 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 -5.2321 2.1340 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 -2.2321 2.1340 0.0000 O 0 0 0 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 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2321 2.1340 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 9 1 0 0 0 0 4 5 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 11 2 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 11 30 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 16 2 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 24 2 0 0 0 0 15 17 1 0 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 17 31 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 18 27 2 0 0 0 0 19 21 1 6 0 0 0 19 28 1 0 0 0 0 19 30 1 0 0 0 0 20 3 1 1 0 0 0 20 31 1 0 0 0 0 21 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.11
Volume:	410.277
LogP:	1.734
LogD:	1.42
LogS:	-3.44
# Rotatable Bonds:	4
TPSA:	170.82
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	4.805
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.525
MDCK Permeability:	1.6725261957617477e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.133
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.831

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.282
Plasma Protein Binding (PPB):	95.66291046142578%
Volume Distribution (VD):	0.731
Pgp-substrate:	6.354927062988281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.208
CYP1A2-substrate:	0.837
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.265
CYP2C9-substrate:	0.585
CYP2D6-inhibitor:	0.348
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.606
CYP3A4-substrate:	0.717

ADMET: Excretion

Clearance (CL):	1.853
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.908
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.927
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.933
Carcinogencity:	0.751
Eye Corrosion:	0.005
Eye Irritation:	0.669
Respiratory Toxicity:	0.698

Download Data

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

Natural Product: NPC328321

Natural Product ID:	NPC328321
*Common Name:**	Purpurquinone B
IUPAC Name:	[(1S,7R,8aS)-1,8a-dihydroxy-7-methyl-6,8-dioxo-3-[(E)-prop-1-enyl]-1H-isochromen-7-yl] 3,4,6-trihydroxy-2-methylbenzoate
Synonyms:	Purpurquinone B
Standard InCHIKey:	PLTDHXZQZPWZBC-QWOQCBQGSA-N
Standard InCHI:	InChI=1S/C21H20O10/c1-4-5-11-6-10-7-14(24)20(3,18(27)21(10,29)19(28)30-11)31-17(26)15-9(2)16(25)13(23)8-12(15)22/h4-8,19,22-23,25,28-29H,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=C3O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823109
PubChem CID:	54672324
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	=	61300.0	nM	PMID[518923]

☑ 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 NPC328321 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	387
0.1-0.2	1671
0.2-0.3	4106
0.3-0.4	8847
0.4-0.5	9138
0.5-0.6	4696
0.6-0.7	6323
0.7-0.8	6391
0.8-0.85	1089
0.85-0.9	32
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC317544
0.9304	High Similarity	NPC317585
0.9207	High Similarity	NPC283041
0.9146	High Similarity	NPC20237
0.9085	High Similarity	NPC191930
0.9068	High Similarity	NPC472889
0.9068	High Similarity	NPC478226
0.9062	High Similarity	NPC208173
0.9062	High Similarity	NPC69043
0.9062	High Similarity	NPC478230
0.9062	High Similarity	NPC170189
0.9057	High Similarity	NPC478224
0.9024	High Similarity	NPC249181
0.9	High Similarity	NPC137301
0.9	High Similarity	NPC478231
0.8994	High Similarity	NPC91809
0.8944	High Similarity	NPC472890
0.8944	High Similarity	NPC478221
0.8938	High Similarity	NPC76041
0.8938	High Similarity	NPC115249
0.8938	High Similarity	NPC184284
0.8931	High Similarity	NPC164762
0.8931	High Similarity	NPC472891
0.8882	High Similarity	NPC472385
0.8882	High Similarity	NPC198324
0.8868	High Similarity	NPC84142
0.8834	High Similarity	NPC478225
0.8834	High Similarity	NPC246466
0.8824	High Similarity	NPC115760
0.8824	High Similarity	NPC101191
0.8824	High Similarity	NPC49344
0.8824	High Similarity	NPC210094
0.8824	High Similarity	NPC264735
0.8824	High Similarity	NPC237435
0.8824	High Similarity	NPC477848
0.8824	High Similarity	NPC43211
0.8824	High Similarity	NPC135277
0.8817	High Similarity	NPC175107
0.8817	High Similarity	NPC190003
0.8795	High Similarity	NPC327809
0.8772	High Similarity	NPC233994
0.8772	High Similarity	NPC211532
0.8765	High Similarity	NPC24043
0.8765	High Similarity	NPC45522
0.8765	High Similarity	NPC101026
0.8765	High Similarity	NPC4390
0.8765	High Similarity	NPC169977
0.8765	High Similarity	NPC21666
0.8765	High Similarity	NPC42773
0.8757	High Similarity	NPC244776
0.8757	High Similarity	NPC155763
0.8757	High Similarity	NPC116864
0.8757	High Similarity	NPC235260
0.8757	High Similarity	NPC20505
0.8706	High Similarity	NPC476405
0.8706	High Similarity	NPC254540
0.8706	High Similarity	NPC153755
0.8706	High Similarity	NPC172807
0.8706	High Similarity	NPC211594
0.8706	High Similarity	NPC117260
0.8698	High Similarity	NPC476771
0.8698	High Similarity	NPC138927
0.8683	High Similarity	NPC94777
0.8678	High Similarity	NPC470447
0.8678	High Similarity	NPC470446
0.8678	High Similarity	NPC470449
0.8678	High Similarity	NPC36138
0.8678	High Similarity	NPC470445
0.8675	High Similarity	NPC474779
0.8663	High Similarity	NPC65563
0.8663	High Similarity	NPC472380
0.8663	High Similarity	NPC268533
0.8663	High Similarity	NPC472384
0.8663	High Similarity	NPC470949
0.8663	High Similarity	NPC472382
0.8647	High Similarity	NPC282987
0.8647	High Similarity	NPC245014
0.8647	High Similarity	NPC84265
0.8639	High Similarity	NPC52550
0.8639	High Similarity	NPC84362
0.8639	High Similarity	NPC223424
0.8639	High Similarity	NPC317489
0.8639	High Similarity	NPC173637
0.8639	High Similarity	NPC127546
0.8639	High Similarity	NPC76482
0.8629	High Similarity	NPC470455
0.8629	High Similarity	NPC470416
0.8629	High Similarity	NPC470451
0.8623	High Similarity	NPC474763
0.8621	High Similarity	NPC222674
0.8613	High Similarity	NPC168584
0.8613	High Similarity	NPC35167
0.8605	High Similarity	NPC253685
0.8605	High Similarity	NPC171706
0.8596	High Similarity	NPC245452
0.8596	High Similarity	NPC476772
0.8588	High Similarity	NPC475942
0.8588	High Similarity	NPC120099
0.8588	High Similarity	NPC93337
0.8588	High Similarity	NPC223747
0.8588	High Similarity	NPC203050
0.8588	High Similarity	NPC219904
0.8588	High Similarity	NPC201292
0.8588	High Similarity	NPC469931
0.8588	High Similarity	NPC45638
0.8588	High Similarity	NPC226294
0.8588	High Similarity	NPC58053
0.8588	High Similarity	NPC225434
0.8588	High Similarity	NPC105025
0.8588	High Similarity	NPC186807
0.858	High Similarity	NPC118284
0.858	High Similarity	NPC113968
0.858	High Similarity	NPC255615
0.858	High Similarity	NPC281131
0.858	High Similarity	NPC88789
0.858	High Similarity	NPC67037
0.858	High Similarity	NPC179950
0.858	High Similarity	NPC181616
0.858	High Similarity	NPC274618
0.858	High Similarity	NPC328940
0.858	High Similarity	NPC276222
0.858	High Similarity	NPC145038
0.858	High Similarity	NPC253662
0.858	High Similarity	NPC99957
0.858	High Similarity	NPC56077
0.858	High Similarity	NPC308404
0.858	High Similarity	NPC73855
0.858	High Similarity	NPC277174
0.858	High Similarity	NPC135599
0.8571	High Similarity	NPC107987
0.8571	High Similarity	NPC317781
0.8563	High Similarity	NPC473571
0.8563	High Similarity	NPC126784
0.8563	High Similarity	NPC470443
0.8563	High Similarity	NPC470444
0.8563	High Similarity	NPC110941
0.8563	High Similarity	NPC241423
0.8563	High Similarity	NPC473682
0.8555	High Similarity	NPC154741
0.8555	High Similarity	NPC61904
0.8555	High Similarity	NPC296018
0.8555	High Similarity	NPC89127
0.8555	High Similarity	NPC169733
0.8555	High Similarity	NPC471669
0.8555	High Similarity	NPC8573
0.8555	High Similarity	NPC144097
0.8554	High Similarity	NPC130894
0.8554	High Similarity	NPC300943
0.8554	High Similarity	NPC191459
0.8554	High Similarity	NPC176300
0.8554	High Similarity	NPC253634
0.8554	High Similarity	NPC105242
0.8554	High Similarity	NPC152166
0.8554	High Similarity	NPC22472
0.8554	High Similarity	NPC204854
0.8554	High Similarity	NPC4481
0.8554	High Similarity	NPC9609
0.8554	High Similarity	NPC19687
0.8554	High Similarity	NPC115798
0.8554	High Similarity	NPC7846
0.8554	High Similarity	NPC18607
0.8554	High Similarity	NPC261004
0.8554	High Similarity	NPC18772
0.8554	High Similarity	NPC143828
0.8554	High Similarity	NPC288669
0.8554	High Similarity	NPC25495
0.8538	High Similarity	NPC206123
0.8538	High Similarity	NPC95866
0.8538	High Similarity	NPC475058
0.8529	High Similarity	NPC146792
0.8529	High Similarity	NPC45618
0.8529	High Similarity	NPC226304
0.8529	High Similarity	NPC116745
0.8529	High Similarity	NPC58716
0.8529	High Similarity	NPC325555
0.8529	High Similarity	NPC265530
0.8521	High Similarity	NPC327652
0.8521	High Similarity	NPC277205
0.8521	High Similarity	NPC470735
0.8521	High Similarity	NPC88243
0.8521	High Similarity	NPC240431
0.8521	High Similarity	NPC55786
0.8521	High Similarity	NPC329647
0.8521	High Similarity	NPC34531
0.8521	High Similarity	NPC19388
0.8514	High Similarity	NPC473073
0.8514	High Similarity	NPC473071
0.8512	High Similarity	NPC215612
0.8512	High Similarity	NPC48860
0.8506	High Similarity	NPC217520
0.8506	High Similarity	NPC217387
0.8506	High Similarity	NPC173837
0.8506	High Similarity	NPC113836
0.8506	High Similarity	NPC258044
0.8506	High Similarity	NPC293626
0.8506	High Similarity	NPC37668
0.8506	High Similarity	NPC476773
0.8506	High Similarity	NPC139571
0.8506	High Similarity	NPC253521
0.8506	High Similarity	NPC196127

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 NPC328321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	980
0.2-0.3	2110
0.3-0.4	2694
0.4-0.5	1756
0.5-0.6	841
0.6-0.7	296
0.7-0.8	117
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD4338	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD6797	Phase 2
0.8439	Intermediate Similarity	NPD7251	Discontinued
0.8373	Intermediate Similarity	NPD3817	Phase 2
0.8314	Intermediate Similarity	NPD3818	Discontinued
0.8313	Intermediate Similarity	NPD2801	Approved
0.8286	Intermediate Similarity	NPD7808	Phase 3
0.8266	Intermediate Similarity	NPD7054	Approved
0.8222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD7472	Approved
0.8114	Intermediate Similarity	NPD7074	Phase 3
0.8107	Intermediate Similarity	NPD3882	Suspended
0.8081	Intermediate Similarity	NPD6232	Discontinued
0.8047	Intermediate Similarity	NPD5402	Approved
0.8046	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD1512	Approved
0.7989	Intermediate Similarity	NPD6166	Phase 2
0.7989	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6190	Approved
0.7955	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1934	Approved
0.7901	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1511	Approved
0.7862	Intermediate Similarity	NPD230	Phase 1
0.7849	Intermediate Similarity	NPD7075	Discontinued
0.7826	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6801	Discontinued
0.7814	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7435	Discontinued
0.7771	Intermediate Similarity	NPD6799	Approved
0.7753	Intermediate Similarity	NPD5844	Phase 1
0.7725	Intermediate Similarity	NPD2534	Approved
0.7725	Intermediate Similarity	NPD2532	Approved
0.7725	Intermediate Similarity	NPD2533	Approved
0.7706	Intermediate Similarity	NPD4380	Phase 2
0.7706	Intermediate Similarity	NPD6599	Discontinued
0.7705	Intermediate Similarity	NPD8150	Discontinued
0.7701	Intermediate Similarity	NPD6234	Discontinued
0.7697	Intermediate Similarity	NPD3751	Discontinued
0.7692	Intermediate Similarity	NPD1653	Approved
0.7674	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7819	Suspended
0.7667	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6535	Approved
0.7647	Intermediate Similarity	NPD6534	Approved
0.7633	Intermediate Similarity	NPD5403	Approved
0.7632	Intermediate Similarity	NPD6778	Approved
0.7632	Intermediate Similarity	NPD6777	Approved
0.7632	Intermediate Similarity	NPD6782	Approved
0.7632	Intermediate Similarity	NPD6776	Approved
0.7632	Intermediate Similarity	NPD6781	Approved
0.7632	Intermediate Similarity	NPD6779	Approved
0.7632	Intermediate Similarity	NPD6780	Approved
0.7627	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6559	Discontinued
0.7619	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD37	Approved
0.7598	Intermediate Similarity	NPD7228	Approved
0.759	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4965	Approved
0.7586	Intermediate Similarity	NPD4967	Phase 2
0.7586	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD1465	Phase 2
0.7571	Intermediate Similarity	NPD3787	Discontinued
0.7551	Intermediate Similarity	NPD7874	Approved
0.7551	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7685	Pre-registration
0.7526	Intermediate Similarity	NPD7699	Phase 2
0.7526	Intermediate Similarity	NPD7700	Phase 2
0.7515	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD7199	Phase 2
0.7474	Intermediate Similarity	NPD8320	Phase 1
0.7474	Intermediate Similarity	NPD8319	Approved
0.7469	Intermediate Similarity	NPD943	Approved
0.7458	Intermediate Similarity	NPD5494	Approved
0.7427	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7698	Approved
0.7423	Intermediate Similarity	NPD7696	Phase 3
0.7423	Intermediate Similarity	NPD7697	Approved
0.7416	Intermediate Similarity	NPD1247	Approved
0.7401	Intermediate Similarity	NPD919	Approved
0.7394	Intermediate Similarity	NPD1510	Phase 2
0.7385	Intermediate Similarity	NPD7870	Phase 2
0.7385	Intermediate Similarity	NPD7871	Phase 2
0.7381	Intermediate Similarity	NPD3750	Approved
0.736	Intermediate Similarity	NPD7701	Phase 2
0.7351	Intermediate Similarity	NPD8312	Approved
0.7351	Intermediate Similarity	NPD8313	Approved
0.7326	Intermediate Similarity	NPD8434	Phase 2
0.7323	Intermediate Similarity	NPD8151	Discontinued
0.7318	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD7266	Discontinued
0.7257	Intermediate Similarity	NPD7411	Suspended
0.725	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7783	Phase 2
0.725	Intermediate Similarity	NPD7801	Approved
0.7247	Intermediate Similarity	NPD3749	Approved
0.7246	Intermediate Similarity	NPD2935	Discontinued
0.7238	Intermediate Similarity	NPD3926	Phase 2
0.7209	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6823	Phase 2
0.7186	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5711	Approved
0.7182	Intermediate Similarity	NPD5710	Approved
0.717	Intermediate Similarity	NPD9269	Phase 2
0.7169	Intermediate Similarity	NPD1607	Approved
0.716	Intermediate Similarity	NPD1549	Phase 2
0.7152	Intermediate Similarity	NPD1240	Approved
0.7151	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7390	Discontinued
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD3226	Approved
0.7135	Intermediate Similarity	NPD6213	Phase 3
0.7135	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6212	Phase 3
0.7135	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2800	Approved
0.711	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD447	Suspended
0.7104	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3748	Approved
0.7076	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD8368	Discontinued
0.7041	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD7768	Phase 2
0.6994	Remote Similarity	NPD3300	Phase 2
0.6977	Remote Similarity	NPD8166	Discontinued
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6651	Approved
0.6952	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8407	Phase 2
0.6939	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7799	Discontinued
0.6932	Remote Similarity	NPD920	Approved
0.6928	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD9268	Approved
0.6901	Remote Similarity	NPD2346	Discontinued
0.6869	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3027	Phase 3
0.6859	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD9545	Approved
0.6854	Remote Similarity	NPD7458	Discontinued
0.6848	Remote Similarity	NPD9494	Approved
0.6845	Remote Similarity	NPD1613	Approved
0.6845	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6099	Approved
0.6842	Remote Similarity	NPD5406	Approved
0.6842	Remote Similarity	NPD5404	Approved
0.6842	Remote Similarity	NPD5408	Approved
0.6842	Remote Similarity	NPD5405	Approved
0.6842	Remote Similarity	NPD6100	Approved
0.6834	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2403	Approved
0.6825	Remote Similarity	NPD5953	Discontinued
0.6821	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7680	Approved
0.6805	Remote Similarity	NPD1933	Approved
0.6804	Remote Similarity	NPD8360	Approved
0.6804	Remote Similarity	NPD8435	Approved
0.6804	Remote Similarity	NPD8361	Approved
0.6798	Remote Similarity	NPD7584	Approved
0.6786	Remote Similarity	NPD6233	Phase 2
0.6777	Remote Similarity	NPD7907	Approved
0.6774	Remote Similarity	NPD5242	Approved
0.6758	Remote Similarity	NPD5353	Approved
0.6746	Remote Similarity	NPD4060	Phase 1
0.6739	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7930	Approved
0.673	Remote Similarity	NPD9493	Approved
0.6727	Remote Similarity	NPD1470	Approved
0.6724	Remote Similarity	NPD1243	Approved
0.672	Remote Similarity	NPD7286	Phase 2
0.672	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8455	Phase 2
0.6687	Remote Similarity	NPD1201	Approved
0.6687	Remote Similarity	NPD2798	Approved
0.6686	Remote Similarity	NPD7033	Discontinued
0.6686	Remote Similarity	NPD2799	Discontinued
0.6683	Remote Similarity	NPD5005	Approved
0.6683	Remote Similarity	NPD5006	Approved
0.6682	Remote Similarity	NPD4665	Approved
0.6682	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD5028	Approved
0.6667	Remote Similarity	NPD5026	Approved
0.6667	Remote Similarity	NPD36	Approved
0.6667	Remote Similarity	NPD4955	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