NPASS Compound

Structure

NPC167463 OpenBabel07101718222D 42 45 0 0 1 0 0 0 0 0999 V2000 -6.7776 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6248 4.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7776 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4720 4.8913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4720 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9304 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6248 3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9304 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -0.4891 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.3192 4.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3192 3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0832 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1664 4.8913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1664 2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 3.9130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0832 -0.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 -3.4239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -3.4239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0832 1.9565 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 5 2 0 0 0 0 1 15 1 0 0 0 0 2 6 2 0 0 0 0 2 16 1 0 0 0 0 3 8 2 0 0 0 0 3 15 1 0 0 0 0 4 9 2 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 26 1 0 0 0 0 11 15 2 0 0 0 0 11 22 1 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 17 2 0 0 0 0 13 24 1 0 0 0 0 14 18 2 0 0 0 0 14 25 1 0 0 0 0 17 41 1 0 0 0 0 18 42 1 0 0 0 0 19 27 1 0 0 0 0 19 28 1 0 0 0 0 20 22 2 0 0 0 0 20 31 1 0 0 0 0 21 23 2 0 0 0 0 21 32 1 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 24 27 2 0 0 0 0 24 35 1 0 0 0 0 25 28 2 0 0 0 0 25 36 1 0 0 0 0 26 37 2 0 0 0 0 26 38 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 29 39 2 0 0 0 0 29 41 1 0 0 0 0 30 40 2 0 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.13
Volume:	559.146
LogP:	3.005
LogD:	1.546
LogS:	-3.61
# Rotatable Bonds:	9
TPSA:	219.1
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	3.42
Fsp3:	0.1
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.852
MDCK Permeability:	9.771444638317917e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.952
Human Intestinal Absorption (HIA):	0.467
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	99.24127197265625%
Volume Distribution (VD):	0.227
Pgp-substrate:	1.0903548002243042%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.551
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.449
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	3.833
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.676
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.962
Carcinogencity:	0.214
Eye Corrosion:	0.003
Eye Irritation:	0.251
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC167463

Natural Product ID:	NPC167463
*Common Name:**	4,4-Bis(6-((E)-3,4-Dihydroxystyryl)-4-Hydroxy-2-Oxo-2H-Pyran-3-Yl)-Butanoic Acid
IUPAC Name:	4,4-bis[6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-yl]butanoic acid
Synonyms:
Standard InCHIKey:	BAUBFAJHDIHNIK-IJIVKGSJSA-N
Standard InCHI:	InChI=1S/C30H24O12/c31-20-8-3-15(11-22(20)33)1-5-17-13-24(35)27(29(39)41-17)19(7-10-26(37)38)28-25(36)14-18(42-30(28)40)6-2-16-4-9-21(32)23(34)12-16/h1-6,8-9,11-14,19,31-36H,7,10H2,(H,37,38)/b5-1+,6-2+
SMILES:	OC(=O)CCC(c1c(O)cc(oc1=O)/C=C/c1ccc(c(c1)O)O)c1c(O)cc(oc1=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408935
PubChem CID:	72192261
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO19202	Phaeolus schweinitzii	Species	Hymenochaetaceae	Eukaryota	fruits	Tibetan Plateau	n.a.	PMID[23869482]
NPO19202	Phaeolus schweinitzii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	4

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.	TAC	=	6.82	U	PMID[483068]
NPT35	Others	n.a.	TAC	=	8.41	U	PMID[483068]
NPT35	Others	n.a.	TAC	=	9.74	U	PMID[483068]
NPT35	Others	n.a.	TAC	=	10.74	U	PMID[483068]
NPT1	Others	Radical scavenging activity	IC50	=	88700.0	nM	PMID[483068]

☑ 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 NPC167463 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	405
0.1-0.2	1702
0.2-0.3	4152
0.3-0.4	9752
0.4-0.5	8442
0.5-0.6	3942
0.6-0.7	5900
0.7-0.8	6326
0.8-0.85	1910
0.85-0.9	145
0.9-0.95	16
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC64111
0.9837	High Similarity	NPC285361
0.9836	High Similarity	NPC46192
0.9756	High Similarity	NPC208536
0.8968	High Similarity	NPC197832
0.896	High Similarity	NPC285345
0.896	High Similarity	NPC306100
0.8881	High Similarity	NPC191280
0.8819	High Similarity	NPC67951
0.8815	High Similarity	NPC9218
0.875	High Similarity	NPC91546
0.875	High Similarity	NPC118584
0.8692	High Similarity	NPC477300
0.8686	High Similarity	NPC285550
0.8676	High Similarity	NPC290664
0.8623	High Similarity	NPC470130
0.8623	High Similarity	NPC183824
0.8595	High Similarity	NPC131530
0.8516	High Similarity	NPC212541
0.8511	High Similarity	NPC155910
0.8511	High Similarity	NPC17042
0.8504	High Similarity	NPC147654
0.8504	High Similarity	NPC472271
0.8496	Intermediate Similarity	NPC61
0.8496	Intermediate Similarity	NPC18074
0.8496	Intermediate Similarity	NPC25581
0.8496	Intermediate Similarity	NPC5419
0.845	Intermediate Similarity	NPC85565
0.845	Intermediate Similarity	NPC288945
0.8444	Intermediate Similarity	NPC311742
0.8433	Intermediate Similarity	NPC168799
0.8433	Intermediate Similarity	NPC155209
0.8421	Intermediate Similarity	NPC198388
0.8413	Intermediate Similarity	NPC141791
0.8413	Intermediate Similarity	NPC263386
0.8409	Intermediate Similarity	NPC94810
0.838	Intermediate Similarity	NPC1580
0.837	Intermediate Similarity	NPC106406
0.8333	Intermediate Similarity	NPC275519
0.8309	Intermediate Similarity	NPC476870
0.8309	Intermediate Similarity	NPC477301
0.8284	Intermediate Similarity	NPC318799
0.8281	Intermediate Similarity	NPC470849
0.8281	Intermediate Similarity	NPC470848
0.8276	Intermediate Similarity	NPC270268
0.8268	Intermediate Similarity	NPC241634
0.8248	Intermediate Similarity	NPC156307
0.824	Intermediate Similarity	NPC474967
0.8235	Intermediate Similarity	NPC248150
0.8214	Intermediate Similarity	NPC477335
0.8214	Intermediate Similarity	NPC471027
0.8214	Intermediate Similarity	NPC35702
0.8214	Intermediate Similarity	NPC297517
0.8214	Intermediate Similarity	NPC206095
0.8214	Intermediate Similarity	NPC13818
0.8214	Intermediate Similarity	NPC224389
0.8214	Intermediate Similarity	NPC296643
0.8201	Intermediate Similarity	NPC289690
0.8201	Intermediate Similarity	NPC288452
0.8182	Intermediate Similarity	NPC276014
0.8175	Intermediate Similarity	NPC281277
0.8175	Intermediate Similarity	NPC277394
0.8175	Intermediate Similarity	NPC299252
0.8175	Intermediate Similarity	NPC61062
0.8169	Intermediate Similarity	NPC477333
0.8168	Intermediate Similarity	NPC246704
0.8162	Intermediate Similarity	NPC471749
0.816	Intermediate Similarity	NPC261453
0.816	Intermediate Similarity	NPC328593
0.816	Intermediate Similarity	NPC33749
0.8156	Intermediate Similarity	NPC192831
0.8156	Intermediate Similarity	NPC303090
0.8156	Intermediate Similarity	NPC258469
0.8156	Intermediate Similarity	NPC277315
0.8156	Intermediate Similarity	NPC284948
0.8156	Intermediate Similarity	NPC472016
0.8156	Intermediate Similarity	NPC37331
0.8156	Intermediate Similarity	NPC319628
0.8156	Intermediate Similarity	NPC43158
0.8156	Intermediate Similarity	NPC220664
0.8145	Intermediate Similarity	NPC51698
0.8143	Intermediate Similarity	NPC477279
0.8143	Intermediate Similarity	NPC38473
0.8134	Intermediate Similarity	NPC241354
0.8129	Intermediate Similarity	NPC142703
0.8129	Intermediate Similarity	NPC302857
0.8129	Intermediate Similarity	NPC219428
0.8129	Intermediate Similarity	NPC152942
0.8129	Intermediate Similarity	NPC37250
0.8129	Intermediate Similarity	NPC278068
0.8125	Intermediate Similarity	NPC23677
0.8116	Intermediate Similarity	NPC471283
0.8116	Intermediate Similarity	NPC90431
0.8106	Intermediate Similarity	NPC289459
0.8099	Intermediate Similarity	NPC160378
0.8095	Intermediate Similarity	NPC233669
0.8085	Intermediate Similarity	NPC477278
0.8085	Intermediate Similarity	NPC477277
0.808	Intermediate Similarity	NPC95381
0.8074	Intermediate Similarity	NPC237506
0.8074	Intermediate Similarity	NPC32626
0.8074	Intermediate Similarity	NPC329344
0.8074	Intermediate Similarity	NPC217052
0.8071	Intermediate Similarity	NPC205751
0.8071	Intermediate Similarity	NPC476820
0.8071	Intermediate Similarity	NPC26241
0.8071	Intermediate Similarity	NPC274891
0.8071	Intermediate Similarity	NPC303683
0.8071	Intermediate Similarity	NPC474875
0.8071	Intermediate Similarity	NPC134969
0.8071	Intermediate Similarity	NPC295492
0.8071	Intermediate Similarity	NPC476819
0.8065	Intermediate Similarity	NPC226250
0.8062	Intermediate Similarity	NPC2058
0.8058	Intermediate Similarity	NPC471152
0.8047	Intermediate Similarity	NPC311091
0.8047	Intermediate Similarity	NPC203124
0.8047	Intermediate Similarity	NPC471033
0.8047	Intermediate Similarity	NPC309434
0.8045	Intermediate Similarity	NPC84076
0.8045	Intermediate Similarity	NPC90128
0.8045	Intermediate Similarity	NPC120225
0.8045	Intermediate Similarity	NPC213552
0.8045	Intermediate Similarity	NPC303680
0.8016	Intermediate Similarity	NPC217472
0.8014	Intermediate Similarity	NPC326065
0.8014	Intermediate Similarity	NPC69367
0.8	Intermediate Similarity	NPC83062
0.8	Intermediate Similarity	NPC294361
0.8	Intermediate Similarity	NPC257173
0.8	Intermediate Similarity	NPC158949
0.8	Intermediate Similarity	NPC236520
0.8	Intermediate Similarity	NPC284409
0.8	Intermediate Similarity	NPC226855
0.7985	Intermediate Similarity	NPC123722
0.7985	Intermediate Similarity	NPC5018
0.7985	Intermediate Similarity	NPC158654
0.7985	Intermediate Similarity	NPC276466
0.7985	Intermediate Similarity	NPC151167
0.7985	Intermediate Similarity	NPC123228
0.7984	Intermediate Similarity	NPC70084
0.7984	Intermediate Similarity	NPC222084
0.7972	Intermediate Similarity	NPC190587
0.7972	Intermediate Similarity	NPC22176
0.7972	Intermediate Similarity	NPC121573
0.7972	Intermediate Similarity	NPC226738
0.7971	Intermediate Similarity	NPC300776
0.7971	Intermediate Similarity	NPC5310
0.7971	Intermediate Similarity	NPC4982
0.7971	Intermediate Similarity	NPC886
0.7971	Intermediate Similarity	NPC135127
0.7971	Intermediate Similarity	NPC34293
0.7971	Intermediate Similarity	NPC68779
0.7971	Intermediate Similarity	NPC474895
0.7971	Intermediate Similarity	NPC176814
0.7971	Intermediate Similarity	NPC287597
0.797	Intermediate Similarity	NPC280767
0.7969	Intermediate Similarity	NPC200988
0.7969	Intermediate Similarity	NPC145023
0.7969	Intermediate Similarity	NPC175799
0.7969	Intermediate Similarity	NPC610
0.7959	Intermediate Similarity	NPC243891
0.7955	Intermediate Similarity	NPC229084
0.7955	Intermediate Similarity	NPC160900
0.7955	Intermediate Similarity	NPC106659
0.7955	Intermediate Similarity	NPC18984
0.7953	Intermediate Similarity	NPC4665
0.7951	Intermediate Similarity	NPC294902
0.7951	Intermediate Similarity	NPC1075
0.7951	Intermediate Similarity	NPC1786
0.7943	Intermediate Similarity	NPC179505
0.7943	Intermediate Similarity	NPC471875
0.7943	Intermediate Similarity	NPC156709
0.7939	Intermediate Similarity	NPC70752
0.7937	Intermediate Similarity	NPC148969
0.7931	Intermediate Similarity	NPC322660
0.7929	Intermediate Similarity	NPC100558
0.7929	Intermediate Similarity	NPC84789
0.7929	Intermediate Similarity	NPC260425
0.7929	Intermediate Similarity	NPC78363
0.7929	Intermediate Similarity	NPC308976
0.7929	Intermediate Similarity	NPC67349
0.7929	Intermediate Similarity	NPC310252
0.7929	Intermediate Similarity	NPC279676
0.7929	Intermediate Similarity	NPC302583
0.7926	Intermediate Similarity	NPC110313
0.792	Intermediate Similarity	NPC297657
0.7917	Intermediate Similarity	NPC53520
0.7917	Intermediate Similarity	NPC257025
0.7914	Intermediate Similarity	NPC113295
0.7914	Intermediate Similarity	NPC123988
0.791	Intermediate Similarity	NPC179777
0.7907	Intermediate Similarity	NPC86198
0.7905	Intermediate Similarity	NPC267091
0.7899	Intermediate Similarity	NPC475468
0.7895	Intermediate Similarity	NPC229113
0.7891	Intermediate Similarity	NPC32197
0.7891	Intermediate Similarity	NPC221091
0.7891	Intermediate Similarity	NPC259576
0.7881	Intermediate Similarity	NPC187205

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 NPC167463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	962
0.2-0.3	1664
0.3-0.4	2651
0.4-0.5	1909
0.5-0.6	1070
0.6-0.7	389
0.7-0.8	112
0.8-0.85	34
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8156	Intermediate Similarity	NPD6190	Approved
0.7955	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3225	Approved
0.7872	Intermediate Similarity	NPD7266	Discontinued
0.7832	Intermediate Similarity	NPD8166	Discontinued
0.7671	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD230	Phase 1
0.7619	Intermediate Similarity	NPD3021	Approved
0.7619	Intermediate Similarity	NPD3022	Approved
0.7582	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1511	Approved
0.745	Intermediate Similarity	NPD1512	Approved
0.7429	Intermediate Similarity	NPD3268	Approved
0.7429	Intermediate Similarity	NPD3764	Approved
0.7424	Intermediate Similarity	NPD5536	Phase 2
0.7368	Intermediate Similarity	NPD9545	Approved
0.7353	Intermediate Similarity	NPD9269	Phase 2
0.7353	Intermediate Similarity	NPD1608	Approved
0.7338	Intermediate Similarity	NPD9494	Approved
0.7338	Intermediate Similarity	NPD2801	Approved
0.7319	Intermediate Similarity	NPD2797	Approved
0.7301	Intermediate Similarity	NPD7685	Pre-registration
0.729	Intermediate Similarity	NPD3817	Phase 2
0.7234	Intermediate Similarity	NPD7095	Approved
0.723	Intermediate Similarity	NPD3750	Approved
0.723	Intermediate Similarity	NPD4628	Phase 3
0.7226	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1465	Phase 2
0.7203	Intermediate Similarity	NPD943	Approved
0.719	Intermediate Similarity	NPD3455	Phase 2
0.7163	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1934	Approved
0.7153	Intermediate Similarity	NPD1535	Discovery
0.7152	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6234	Discontinued
0.7132	Intermediate Similarity	NPD17	Approved
0.7124	Intermediate Similarity	NPD1653	Approved
0.7117	Intermediate Similarity	NPD7054	Approved
0.7113	Intermediate Similarity	NPD3027	Phase 3
0.7101	Intermediate Similarity	NPD1481	Phase 2
0.7099	Intermediate Similarity	NPD228	Approved
0.7095	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5909	Discontinued
0.7083	Intermediate Similarity	NPD826	Approved
0.7083	Intermediate Similarity	NPD4060	Phase 1
0.7083	Intermediate Similarity	NPD825	Approved
0.7075	Intermediate Similarity	NPD2935	Discontinued
0.7073	Intermediate Similarity	NPD7472	Approved
0.7071	Intermediate Similarity	NPD3266	Approved
0.7071	Intermediate Similarity	NPD3267	Approved
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3818	Discontinued
0.7054	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6166	Phase 2
0.7037	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6355	Discontinued
0.7034	Intermediate Similarity	NPD4340	Discontinued
0.7032	Intermediate Similarity	NPD4380	Phase 2
0.703	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6797	Phase 2
0.7025	Intermediate Similarity	NPD3882	Suspended
0.7024	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD257	Approved
0.7021	Intermediate Similarity	NPD258	Approved
0.7019	Intermediate Similarity	NPD6232	Discontinued
0.7014	Intermediate Similarity	NPD6233	Phase 2
0.7007	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4110	Phase 3
0.7	Intermediate Similarity	NPD1283	Approved
0.6994	Remote Similarity	NPD7473	Discontinued
0.6992	Remote Similarity	NPD5283	Phase 1
0.6988	Remote Similarity	NPD7251	Discontinued
0.6985	Remote Similarity	NPD1894	Discontinued
0.6977	Remote Similarity	NPD3134	Approved
0.6972	Remote Similarity	NPD9569	Approved
0.6972	Remote Similarity	NPD5736	Approved
0.697	Remote Similarity	NPD7074	Phase 3
0.6966	Remote Similarity	NPD1613	Approved
0.6966	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5402	Approved
0.6957	Remote Similarity	NPD3847	Discontinued
0.6957	Remote Similarity	NPD7199	Phase 2
0.6951	Remote Similarity	NPD7228	Approved
0.695	Remote Similarity	NPD1203	Approved
0.6948	Remote Similarity	NPD5403	Approved
0.6943	Remote Similarity	NPD37	Approved
0.6934	Remote Similarity	NPD5585	Approved
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2614	Approved
0.6923	Remote Similarity	NPD1358	Approved
0.6918	Remote Similarity	NPD4966	Approved
0.6918	Remote Similarity	NPD555	Phase 2
0.6918	Remote Similarity	NPD447	Suspended
0.6918	Remote Similarity	NPD4965	Approved
0.6918	Remote Similarity	NPD4967	Phase 2
0.6917	Remote Similarity	NPD5535	Approved
0.6906	Remote Similarity	NPD422	Phase 1
0.6905	Remote Similarity	NPD3020	Approved
0.6897	Remote Similarity	NPD259	Phase 1
0.6897	Remote Similarity	NPD4062	Phase 3
0.6897	Remote Similarity	NPD6663	Approved
0.6892	Remote Similarity	NPD2799	Discontinued
0.6892	Remote Similarity	NPD1510	Phase 2
0.6892	Remote Similarity	NPD7033	Discontinued
0.6892	Remote Similarity	NPD3748	Approved
0.6887	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3019	Approved
0.6884	Remote Similarity	NPD2932	Approved
0.6879	Remote Similarity	NPD7411	Suspended
0.6875	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7075	Discontinued
0.6871	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3226	Approved
0.6855	Remote Similarity	NPD2934	Approved
0.6855	Remote Similarity	NPD2933	Approved
0.6852	Remote Similarity	NPD8127	Discontinued
0.685	Remote Similarity	NPD1242	Phase 1
0.6846	Remote Similarity	NPD5406	Approved
0.6846	Remote Similarity	NPD5404	Approved
0.6846	Remote Similarity	NPD5408	Approved
0.6846	Remote Similarity	NPD5405	Approved
0.6845	Remote Similarity	NPD7808	Phase 3
0.6828	Remote Similarity	NPD2313	Discontinued
0.6818	Remote Similarity	NPD5401	Approved
0.6818	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2983	Phase 2
0.6809	Remote Similarity	NPD2982	Phase 2
0.6807	Remote Similarity	NPD5844	Phase 1
0.6802	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2859	Approved
0.68	Remote Similarity	NPD2860	Approved
0.6792	Remote Similarity	NPD7819	Suspended
0.6786	Remote Similarity	NPD1281	Approved
0.6783	Remote Similarity	NPD2798	Approved
0.6779	Remote Similarity	NPD4308	Phase 3
0.6776	Remote Similarity	NPD7003	Approved
0.6774	Remote Similarity	NPD6273	Approved
0.6772	Remote Similarity	NPD6386	Approved
0.6772	Remote Similarity	NPD6385	Approved
0.6763	Remote Similarity	NPD4626	Approved
0.6759	Remote Similarity	NPD9537	Phase 1
0.6759	Remote Similarity	NPD9536	Phase 1
0.6753	Remote Similarity	NPD6799	Approved
0.6753	Remote Similarity	NPD4357	Discontinued
0.6752	Remote Similarity	NPD7458	Discontinued
0.675	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2981	Phase 2
0.6736	Remote Similarity	NPD2861	Phase 2
0.6735	Remote Similarity	NPD2979	Phase 3
0.6735	Remote Similarity	NPD1558	Phase 1
0.6733	Remote Similarity	NPD1551	Phase 2
0.6733	Remote Similarity	NPD2438	Suspended
0.673	Remote Similarity	NPD6801	Discontinued
0.6715	Remote Similarity	NPD9493	Approved
0.6714	Remote Similarity	NPD3496	Discontinued
0.6711	Remote Similarity	NPD7097	Phase 1
0.6709	Remote Similarity	NPD7028	Phase 2
0.669	Remote Similarity	NPD4359	Approved
0.669	Remote Similarity	NPD4908	Phase 1
0.6689	Remote Similarity	NPD274	Approved
0.6689	Remote Similarity	NPD1933	Approved
0.6689	Remote Similarity	NPD275	Approved
0.6689	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5124	Phase 1
0.6689	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1201	Approved
0.6646	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5958	Discontinued
0.6645	Remote Similarity	NPD1549	Phase 2
0.6644	Remote Similarity	NPD6653	Approved
0.6642	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6099	Approved
0.6623	Remote Similarity	NPD2354	Approved
0.6623	Remote Similarity	NPD6100	Approved
0.6623	Remote Similarity	NPD9570	Approved
0.6622	Remote Similarity	NPD3620	Phase 2
0.6622	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1240	Approved
0.6621	Remote Similarity	NPD3018	Phase 2
0.662	Remote Similarity	NPD9717	Approved
0.6619	Remote Similarity	NPD1548	Phase 1
0.6605	Remote Similarity	NPD7768	Phase 2
0.66	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1470	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