NPASS Compound

Structure

NPC470357 OpenBabel07101719512D 25 26 0 0 1 0 0 0 0 0999 V2000 -5.8690 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6010 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6010 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6010 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4670 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 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 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 5 9 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 25 1 0 0 0 0 9 13 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 13 19 1 6 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.14
Volume:	348.484
LogP:	1.78
LogD:	1.263
LogS:	-3.481
# Rotatable Bonds:	7
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.573
Synthetic Accessibility Score:	3.474
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.341
MDCK Permeability:	1.3679876246897038e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.625
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	89.30670928955078%
Volume Distribution (VD):	0.516
Pgp-substrate:	7.949526786804199%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.715
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.719
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.795
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	9.436
Half-life (T1/2):	0.765

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.554
AMES Toxicity:	0.482
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.357
Carcinogencity:	0.611
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.739

Download Data

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

Natural Product: NPC470357

Natural Product ID:	NPC470357
*Common Name:**	Penicacid A
IUPAC Name:	(E,3S)-6-(4,6-dimethoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-3-hydroxy-4-methylhex-4-enoic acid
Synonyms:	Penicacid A
Standard InCHIKey:	FLHIJSDWAVXPEH-NEXMIYJRSA-N
Standard InCHI:	InChI=1S/C18H22O7/c1-9(13(19)7-14(20)21)5-6-11-16(23-3)10(2)12-8-25-18(22)15(12)17(11)24-4/h5,13,19H,6-8H2,1-4H3,(H,20,21)/b9-5+/t13-/m0/s1
SMILES:	CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)C(CC(=O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2017524
PubChem CID:	59053796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004191] Isocoumarans [CHEMONTID:0003409] Isobenzofuranones [CHEMONTID:0001873] Phthalides

*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
NPO33088	penicillium sp. sof07	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22464133]

☑ 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

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2817	Individual Protein	Inosine-5'-monophosphate dehydrogenase 2	Homo sapiens	IC50	=	28860.0	nM	PMID[544249]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2460.0	nM	PMID[544249]

☑ 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 NPC470357 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	317
0.1-0.2	1387
0.2-0.3	3349
0.3-0.4	7318
0.4-0.5	11223
0.5-0.6	4642
0.6-0.7	6463
0.7-0.8	6588
0.8-0.85	1164
0.85-0.9	214
0.9-0.95	28
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC8817
0.9786	High Similarity	NPC75694
0.9648	High Similarity	NPC137296
0.9444	High Similarity	NPC470359
0.9231	High Similarity	NPC51106
0.9205	High Similarity	NPC470358
0.9184	High Similarity	NPC179178
0.9184	High Similarity	NPC119929
0.9133	High Similarity	NPC477674
0.9122	High Similarity	NPC200773
0.9122	High Similarity	NPC240768
0.911	High Similarity	NPC53362
0.911	High Similarity	NPC166583
0.9097	High Similarity	NPC472006
0.9091	High Similarity	NPC67650
0.9091	High Similarity	NPC1704
0.9091	High Similarity	NPC90411
0.906	High Similarity	NPC271681
0.906	High Similarity	NPC273483
0.9041	High Similarity	NPC107625
0.9028	High Similarity	NPC474385
0.9028	High Similarity	NPC469579
0.9021	High Similarity	NPC165172
0.902	High Similarity	NPC117985
0.9	High Similarity	NPC477669
0.8966	High Similarity	NPC471731
0.8966	High Similarity	NPC469542
0.8966	High Similarity	NPC159721
0.8951	High Similarity	NPC275356
0.894	High Similarity	NPC477671
0.894	High Similarity	NPC477687
0.8926	High Similarity	NPC469619
0.8926	High Similarity	NPC469670
0.8912	High Similarity	NPC225173
0.8912	High Similarity	NPC163846
0.8904	High Similarity	NPC86373
0.8904	High Similarity	NPC280404
0.8904	High Similarity	NPC470932
0.8904	High Similarity	NPC210425
0.8904	High Similarity	NPC277426
0.8904	High Similarity	NPC151607
0.8904	High Similarity	NPC42540
0.8897	High Similarity	NPC471733
0.8882	High Similarity	NPC477675
0.8881	High Similarity	NPC212693
0.8881	High Similarity	NPC94248
0.8873	High Similarity	NPC472599
0.8867	High Similarity	NPC477672
0.8867	High Similarity	NPC215921
0.8867	High Similarity	NPC477673
0.8867	High Similarity	NPC70016
0.8859	High Similarity	NPC291049
0.8859	High Similarity	NPC233267
0.8851	High Similarity	NPC125801
0.8851	High Similarity	NPC472036
0.8836	High Similarity	NPC294432
0.8836	High Similarity	NPC472344
0.8828	High Similarity	NPC472605
0.8828	High Similarity	NPC472604
0.8828	High Similarity	NPC475730
0.8824	High Similarity	NPC84935
0.8824	High Similarity	NPC190020
0.8824	High Similarity	NPC77679
0.8816	High Similarity	NPC79998
0.8811	High Similarity	NPC70380
0.8811	High Similarity	NPC135837
0.8808	High Similarity	NPC175978
0.8792	High Similarity	NPC2569
0.8792	High Similarity	NPC37139
0.8792	High Similarity	NPC172329
0.8792	High Similarity	NPC105415
0.8784	High Similarity	NPC472033
0.8776	High Similarity	NPC184702
0.8776	High Similarity	NPC470909
0.8776	High Similarity	NPC474939
0.8776	High Similarity	NPC184738
0.8776	High Similarity	NPC96216
0.8776	High Similarity	NPC33653
0.8767	High Similarity	NPC297985
0.8766	High Similarity	NPC470339
0.8759	High Similarity	NPC472601
0.8759	High Similarity	NPC472600
0.8758	High Similarity	NPC150227
0.8758	High Similarity	NPC146211
0.875	High Similarity	NPC191835
0.875	High Similarity	NPC472799
0.8742	High Similarity	NPC133856
0.8742	High Similarity	NPC470569
0.8741	High Similarity	NPC158481
0.8741	High Similarity	NPC156967
0.8733	High Similarity	NPC198927
0.8733	High Similarity	NPC270160
0.8733	High Similarity	NPC237440
0.8725	High Similarity	NPC471734
0.8725	High Similarity	NPC210320
0.8716	High Similarity	NPC133060
0.8716	High Similarity	NPC470554
0.8716	High Similarity	NPC472034
0.8716	High Similarity	NPC83272
0.8716	High Similarity	NPC288910
0.8716	High Similarity	NPC118059
0.8714	High Similarity	NPC296158
0.871	High Similarity	NPC313368
0.871	High Similarity	NPC143050
0.871	High Similarity	NPC470810
0.871	High Similarity	NPC472055
0.8707	High Similarity	NPC112829
0.8707	High Similarity	NPC470556
0.8701	High Similarity	NPC263483
0.8699	High Similarity	NPC37530
0.8699	High Similarity	NPC158634
0.8699	High Similarity	NPC472603
0.8693	High Similarity	NPC82592
0.8693	High Similarity	NPC16082
0.8693	High Similarity	NPC99381
0.8693	High Similarity	NPC199926
0.8693	High Similarity	NPC149618
0.8693	High Similarity	NPC89625
0.869	High Similarity	NPC105456
0.869	High Similarity	NPC139634
0.869	High Similarity	NPC32360
0.8684	High Similarity	NPC217447
0.8681	High Similarity	NPC194579
0.8681	High Similarity	NPC245058
0.8675	High Similarity	NPC96501
0.8675	High Similarity	NPC158866
0.8675	High Similarity	NPC150928
0.8675	High Similarity	NPC147735
0.8675	High Similarity	NPC470568
0.8675	High Similarity	NPC202595
0.8675	High Similarity	NPC470908
0.8671	High Similarity	NPC182496
0.8671	High Similarity	NPC180905
0.8667	High Similarity	NPC471641
0.8667	High Similarity	NPC215711
0.8667	High Similarity	NPC471642
0.8667	High Similarity	NPC240622
0.8667	High Similarity	NPC240253
0.8667	High Similarity	NPC153417
0.8667	High Similarity	NPC73411
0.8662	High Similarity	NPC100849
0.8658	High Similarity	NPC471735
0.8658	High Similarity	NPC260946
0.8658	High Similarity	NPC470910
0.8658	High Similarity	NPC473023
0.8649	High Similarity	NPC471305
0.8649	High Similarity	NPC307895
0.8649	High Similarity	NPC470553
0.8649	High Similarity	NPC27106
0.8639	High Similarity	NPC74397
0.8639	High Similarity	NPC250755
0.8636	High Similarity	NPC472050
0.8636	High Similarity	NPC180924
0.863	High Similarity	NPC187690
0.863	High Similarity	NPC99441
0.863	High Similarity	NPC158472
0.8627	High Similarity	NPC281477
0.8627	High Similarity	NPC471695
0.8625	High Similarity	NPC17219
0.8625	High Similarity	NPC477571
0.8625	High Similarity	NPC477573
0.8625	High Similarity	NPC477572
0.8621	High Similarity	NPC472602
0.8621	High Similarity	NPC33144
0.8621	High Similarity	NPC478200
0.8618	High Similarity	NPC232645
0.8618	High Similarity	NPC72958
0.8616	High Similarity	NPC473094
0.8611	High Similarity	NPC84699
0.8609	High Similarity	NPC77325
0.8609	High Similarity	NPC476684
0.8609	High Similarity	NPC4423
0.86	High Similarity	NPC14098
0.86	High Similarity	NPC285748
0.8591	High Similarity	NPC473692
0.8591	High Similarity	NPC134621
0.8581	High Similarity	NPC473395
0.8581	High Similarity	NPC96342
0.8581	High Similarity	NPC84266
0.8581	High Similarity	NPC164110
0.8581	High Similarity	NPC472610
0.8581	High Similarity	NPC212967
0.8581	High Similarity	NPC246466
0.8581	High Similarity	NPC302258
0.8581	High Similarity	NPC246647
0.8571	High Similarity	NPC149533
0.8571	High Similarity	NPC16286
0.8571	High Similarity	NPC53649
0.8571	High Similarity	NPC244923
0.8571	High Similarity	NPC478217
0.8571	High Similarity	NPC313123
0.8562	High Similarity	NPC113608
0.8562	High Similarity	NPC470338
0.8562	High Similarity	NPC167903
0.8562	High Similarity	NPC473095
0.8562	High Similarity	NPC40356
0.8562	High Similarity	NPC470340
0.8562	High Similarity	NPC154683
0.8562	High Similarity	NPC470337
0.8562	High Similarity	NPC51824

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 NPC470357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	974
0.2-0.3	1909
0.3-0.4	2558
0.4-0.5	1918
0.5-0.6	1003
0.6-0.7	363
0.7-0.8	134
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9786	High Similarity	NPD2534	Approved
0.9786	High Similarity	NPD2532	Approved
0.9786	High Similarity	NPD2533	Approved
0.8839	High Similarity	NPD5711	Approved
0.8839	High Similarity	NPD5710	Approved
0.8562	High Similarity	NPD970	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD7819	Suspended
0.8378	Intermediate Similarity	NPD2800	Approved
0.8365	Intermediate Similarity	NPD6232	Discontinued
0.821	Intermediate Similarity	NPD7473	Discontinued
0.8194	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.811	Intermediate Similarity	NPD5844	Phase 1
0.8038	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4380	Phase 2
0.7933	Intermediate Similarity	NPD2935	Discontinued
0.7925	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7411	Suspended
0.7898	Intermediate Similarity	NPD3226	Approved
0.7888	Intermediate Similarity	NPD7075	Discontinued
0.7885	Intermediate Similarity	NPD920	Approved
0.7881	Intermediate Similarity	NPD2346	Discontinued
0.7862	Intermediate Similarity	NPD6801	Discontinued
0.7862	Intermediate Similarity	NPD37	Approved
0.7857	Intermediate Similarity	NPD6559	Discontinued
0.7852	Intermediate Similarity	NPD6651	Approved
0.7852	Intermediate Similarity	NPD1607	Approved
0.7848	Intermediate Similarity	NPD6599	Discontinued
0.7826	Intermediate Similarity	NPD4966	Approved
0.7826	Intermediate Similarity	NPD4967	Phase 2
0.7826	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD5494	Approved
0.7778	Intermediate Similarity	NPD1243	Approved
0.7778	Intermediate Similarity	NPD3749	Approved
0.7764	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1934	Approved
0.7748	Intermediate Similarity	NPD1510	Phase 2
0.7748	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7725	Intermediate Similarity	NPD3818	Discontinued
0.7718	Intermediate Similarity	NPD1240	Approved
0.7716	Intermediate Similarity	NPD3882	Suspended
0.7716	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7768	Phase 2
0.7712	Intermediate Similarity	NPD1549	Phase 2
0.7697	Intermediate Similarity	NPD1551	Phase 2
0.7697	Intermediate Similarity	NPD2796	Approved
0.7692	Intermediate Similarity	NPD6799	Approved
0.7667	Intermediate Similarity	NPD230	Phase 1
0.7657	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3817	Phase 2
0.7643	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6234	Discontinued
0.7613	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD3750	Approved
0.7605	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2801	Approved
0.759	Intermediate Similarity	NPD7229	Phase 3
0.7584	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7390	Discontinued
0.7562	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4626	Approved
0.755	Intermediate Similarity	NPD5124	Phase 1
0.755	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5402	Approved
0.7532	Intermediate Similarity	NPD6005	Phase 3
0.7532	Intermediate Similarity	NPD6002	Phase 3
0.7532	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6004	Phase 3
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5691	Approved
0.7471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD1511	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.7427	Intermediate Similarity	NPD7074	Phase 3
0.7412	Intermediate Similarity	NPD7228	Approved
0.7403	Intermediate Similarity	NPD3748	Approved
0.7399	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5953	Discontinued
0.7378	Intermediate Similarity	NPD1465	Phase 2
0.7375	Intermediate Similarity	NPD1512	Approved
0.7368	Intermediate Similarity	NPD7054	Approved
0.7368	Intermediate Similarity	NPD7286	Phase 2
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7355	Intermediate Similarity	NPD6099	Approved
0.7355	Intermediate Similarity	NPD6100	Approved
0.7351	Intermediate Similarity	NPD411	Approved
0.7351	Intermediate Similarity	NPD2313	Discontinued
0.7345	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5403	Approved
0.7326	Intermediate Similarity	NPD7472	Approved
0.7326	Intermediate Similarity	NPD8151	Discontinued
0.7325	Intermediate Similarity	NPD2654	Approved
0.7321	Intermediate Similarity	NPD1247	Approved
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD447	Suspended
0.7299	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1283	Approved
0.729	Intermediate Similarity	NPD7033	Discontinued
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6797	Phase 2
0.7279	Intermediate Similarity	NPD9717	Approved
0.7278	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7255	Intermediate Similarity	NPD2979	Phase 3
0.7243	Intermediate Similarity	NPD7435	Discontinued
0.7241	Intermediate Similarity	NPD7251	Discontinued
0.7237	Intermediate Similarity	NPD3764	Approved
0.7232	Intermediate Similarity	NPD8434	Phase 2
0.7232	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5401	Approved
0.72	Intermediate Similarity	NPD7808	Phase 3
0.72	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2344	Approved
0.7197	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6782	Approved
0.7174	Intermediate Similarity	NPD6779	Approved
0.7174	Intermediate Similarity	NPD6777	Approved
0.7174	Intermediate Similarity	NPD6776	Approved
0.7174	Intermediate Similarity	NPD6778	Approved
0.7174	Intermediate Similarity	NPD6781	Approved
0.7174	Intermediate Similarity	NPD6780	Approved
0.7172	Intermediate Similarity	NPD9545	Approved
0.7169	Intermediate Similarity	NPD5761	Phase 2
0.7169	Intermediate Similarity	NPD5760	Phase 2
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3926	Phase 2
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD2438	Suspended
0.711	Intermediate Similarity	NPD7177	Discontinued
0.7105	Intermediate Similarity	NPD6832	Phase 2
0.7101	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1281	Approved
0.7092	Intermediate Similarity	NPD8366	Approved
0.7079	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1778	Approved
0.7068	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7783	Phase 2
0.7059	Intermediate Similarity	NPD7696	Phase 3
0.7059	Intermediate Similarity	NPD7697	Approved
0.7059	Intermediate Similarity	NPD7698	Approved
0.7059	Intermediate Similarity	NPD4625	Phase 3
0.7047	Intermediate Similarity	NPD1608	Approved
0.7034	Intermediate Similarity	NPD9493	Approved
0.7032	Intermediate Similarity	NPD943	Approved
0.7024	Intermediate Similarity	NPD5353	Approved
0.7021	Intermediate Similarity	NPD7871	Phase 2
0.7021	Intermediate Similarity	NPD7870	Phase 2
0.702	Intermediate Similarity	NPD1203	Approved
0.7019	Intermediate Similarity	NPD2309	Approved
0.7016	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7874	Approved
0.7013	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7985	Registered
0.7011	Intermediate Similarity	NPD3751	Discontinued
0.7007	Intermediate Similarity	NPD9268	Approved
0.6995	Remote Similarity	NPD6535	Approved
0.6995	Remote Similarity	NPD6534	Approved
0.6981	Remote Similarity	NPD1471	Phase 3
0.698	Remote Similarity	NPD422	Phase 1
0.6977	Remote Similarity	NPD3787	Discontinued
0.6974	Remote Similarity	NPD1019	Discontinued
0.6974	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4308	Phase 3
0.6961	Remote Similarity	NPD4287	Approved
0.6954	Remote Similarity	NPD6696	Suspended
0.695	Remote Similarity	NPD8491	Approved
0.6949	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5242	Approved
0.6933	Remote Similarity	NPD9269	Phase 2
0.6923	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD4288	Approved
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD4476	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