NPASS Compound

Structure

CID281272 OpenBabel06191716092D 23 25 0 0 0 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 -0.8660 -1.5000 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 1.7321 -0.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 7 2 0 0 0 0 4 9 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.06
Volume:	300.063
LogP:	2.76
LogD:	2.155
LogS:	-4.036
# Rotatable Bonds:	3
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	2.626
Fsp3:	0.125
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:	-4.988
MDCK Permeability:	7.62014542488032e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.133
Human Intestinal Absorption (HIA):	0.65
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	89.0607681274414%
Volume Distribution (VD):	0.878
Pgp-substrate:	12.478191375732422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.732
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.653
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.38
CYP3A4-substrate:	0.111

ADMET: Excretion

Clearance (CL):	3.199
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.532
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.537
Carcinogencity:	0.025
Eye Corrosion:	0.008
Eye Irritation:	0.953
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC281272

Natural Product ID:	NPC281272
*Common Name:**	Sydowinin B
IUPAC Name:	methyl 2,8-dihydroxy-6-(hydroxymethyl)-9-oxoxanthene-1-carboxylate
Synonyms:	Sydowinin B
Standard InCHIKey:	SSBSKLSIZKVBFF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O7/c1-22-16(21)13-8(18)2-3-10-14(13)15(20)12-9(19)4-7(6-17)5-11(12)23-10/h2-5,17-19H,6H2,1H3
SMILES:	COC(=O)c1c(ccc2c1c(=O)c1c(cc(cc1o2)CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812029
PubChem CID:	45359153
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]
NPO40032	Aspergillus austroafricanus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27070198]

☑ 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
Others	2

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	85.03	%	PMID[572575]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12620.0	nM	PMID[572575]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	66.25	%	PMID[572575]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21200.0	nM	PMID[572575]

☑ 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 NPC281272 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	388
0.1-0.2	1758
0.2-0.3	4072
0.3-0.4	9539
0.4-0.5	8963
0.5-0.6	3891
0.6-0.7	5698
0.7-0.8	5101
0.8-0.85	2656
0.85-0.9	608
0.9-0.95	18
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC39819
0.94	High Similarity	NPC135522
0.9392	High Similarity	NPC70764
0.9388	High Similarity	NPC71055
0.9205	High Similarity	NPC474843
0.92	High Similarity	NPC470107
0.9195	High Similarity	NPC5537
0.9195	High Similarity	NPC228012
0.9156	High Similarity	NPC186113
0.911	High Similarity	NPC145673
0.9091	High Similarity	NPC44199
0.9073	High Similarity	NPC202595
0.9073	High Similarity	NPC295036
0.8993	High Similarity	NPC469764
0.8981	High Similarity	NPC473961
0.8973	High Similarity	NPC18457
0.8954	High Similarity	NPC473967
0.8954	High Similarity	NPC273483
0.8954	High Similarity	NPC175978
0.8947	High Similarity	NPC227122
0.894	High Similarity	NPC2569
0.894	High Similarity	NPC172329
0.8933	High Similarity	NPC469758
0.8933	High Similarity	NPC211565
0.8933	High Similarity	NPC300540
0.8896	High Similarity	NPC477691
0.8882	High Similarity	NPC241874
0.8875	High Similarity	NPC234331
0.8859	High Similarity	NPC310340
0.8854	High Similarity	NPC143050
0.8846	High Similarity	NPC477833
0.8839	High Similarity	NPC237560
0.8831	High Similarity	NPC253904
0.8831	High Similarity	NPC217447
0.8831	High Similarity	NPC40356
0.8831	High Similarity	NPC477690
0.8831	High Similarity	NPC154683
0.8831	High Similarity	NPC321363
0.8824	High Similarity	NPC255641
0.8824	High Similarity	NPC147735
0.8824	High Similarity	NPC290954
0.8824	High Similarity	NPC294646
0.8812	High Similarity	NPC29160
0.8808	High Similarity	NPC267509
0.8808	High Similarity	NPC60389
0.88	High Similarity	NPC113770
0.88	High Similarity	NPC274085
0.88	High Similarity	NPC89664
0.879	High Similarity	NPC329091
0.8782	High Similarity	NPC146211
0.8774	High Similarity	NPC280530
0.8774	High Similarity	NPC95842
0.8774	High Similarity	NPC178964
0.8766	High Similarity	NPC72958
0.8766	High Similarity	NPC232645
0.8766	High Similarity	NPC46564
0.8766	High Similarity	NPC207346
0.8758	High Similarity	NPC233267
0.8758	High Similarity	NPC266499
0.8758	High Similarity	NPC291049
0.8758	High Similarity	NPC76647
0.8758	High Similarity	NPC225419
0.875	High Similarity	NPC46941
0.8742	High Similarity	NPC134621
0.8742	High Similarity	NPC303185
0.8742	High Similarity	NPC184649
0.8742	High Similarity	NPC32470
0.8742	High Similarity	NPC311144
0.8733	High Similarity	NPC169479
0.8733	High Similarity	NPC73028
0.8733	High Similarity	NPC159855
0.8733	High Similarity	NPC476473
0.8726	High Similarity	NPC263483
0.8725	High Similarity	NPC275734
0.8725	High Similarity	NPC124365
0.8718	High Similarity	NPC326910
0.8718	High Similarity	NPC175192
0.8716	High Similarity	NPC268691
0.871	High Similarity	NPC75069
0.871	High Similarity	NPC271681
0.871	High Similarity	NPC87708
0.8704	High Similarity	NPC99613
0.8704	High Similarity	NPC165979
0.8704	High Similarity	NPC163130
0.8704	High Similarity	NPC49487
0.8701	High Similarity	NPC213382
0.8701	High Similarity	NPC164527
0.8701	High Similarity	NPC37348
0.8701	High Similarity	NPC225129
0.8701	High Similarity	NPC325983
0.8701	High Similarity	NPC119929
0.8696	High Similarity	NPC30027
0.8693	High Similarity	NPC37135
0.8693	High Similarity	NPC7025
0.8693	High Similarity	NPC191634
0.8693	High Similarity	NPC105415
0.8693	High Similarity	NPC186397
0.8693	High Similarity	NPC256672
0.8693	High Similarity	NPC27221
0.8688	High Similarity	NPC197168
0.8688	High Similarity	NPC474350
0.8684	High Similarity	NPC163846
0.8684	High Similarity	NPC225173
0.8684	High Similarity	NPC196114
0.8684	High Similarity	NPC237208
0.8684	High Similarity	NPC299011
0.8679	High Similarity	NPC474187
0.8679	High Similarity	NPC24761
0.8675	High Similarity	NPC95123
0.8675	High Similarity	NPC66404
0.8671	High Similarity	NPC477692
0.8667	High Similarity	NPC474300
0.8667	High Similarity	NPC105648
0.8667	High Similarity	NPC250755
0.8662	High Similarity	NPC154341
0.8654	High Similarity	NPC169990
0.8654	High Similarity	NPC299435
0.8654	High Similarity	NPC210942
0.8654	High Similarity	NPC472799
0.8654	High Similarity	NPC89474
0.8654	High Similarity	NPC260604
0.865	High Similarity	NPC474004
0.8645	High Similarity	NPC149526
0.8645	High Similarity	NPC474417
0.8645	High Similarity	NPC470569
0.8645	High Similarity	NPC70016
0.8645	High Similarity	NPC478148
0.8645	High Similarity	NPC215921
0.8645	High Similarity	NPC202157
0.8645	High Similarity	NPC133856
0.8645	High Similarity	NPC117579
0.8636	High Similarity	NPC158338
0.8636	High Similarity	NPC4423
0.8636	High Similarity	NPC97029
0.8636	High Similarity	NPC285527
0.8636	High Similarity	NPC106334
0.8636	High Similarity	NPC77325
0.8636	High Similarity	NPC288036
0.8636	High Similarity	NPC73236
0.8636	High Similarity	NPC200221
0.8636	High Similarity	NPC97028
0.8636	High Similarity	NPC65589
0.8636	High Similarity	NPC223988
0.8636	High Similarity	NPC294502
0.8636	High Similarity	NPC100985
0.8634	High Similarity	NPC25361
0.8634	High Similarity	NPC112981
0.8634	High Similarity	NPC178281
0.8627	High Similarity	NPC126767
0.8627	High Similarity	NPC190648
0.8627	High Similarity	NPC22005
0.8627	High Similarity	NPC125801
0.8627	High Similarity	NPC308200
0.8627	High Similarity	NPC289042
0.8627	High Similarity	NPC7943
0.8627	High Similarity	NPC146884
0.8627	High Similarity	NPC56433
0.8627	High Similarity	NPC312929
0.8627	High Similarity	NPC245584
0.8627	High Similarity	NPC123202
0.8627	High Similarity	NPC118027
0.8618	High Similarity	NPC131766
0.8618	High Similarity	NPC29577
0.8616	High Similarity	NPC475886
0.8616	High Similarity	NPC119224
0.8616	High Similarity	NPC474287
0.8614	High Similarity	NPC477682
0.8614	High Similarity	NPC477683
0.8609	High Similarity	NPC469542
0.8609	High Similarity	NPC1534
0.8609	High Similarity	NPC472006
0.8609	High Similarity	NPC202981
0.8609	High Similarity	NPC51106
0.8608	High Similarity	NPC165977
0.8608	High Similarity	NPC300727
0.8608	High Similarity	NPC181960
0.8608	High Similarity	NPC241904
0.8608	High Similarity	NPC177742
0.8608	High Similarity	NPC217677
0.8606	High Similarity	NPC289147
0.8606	High Similarity	NPC470454
0.8606	High Similarity	NPC68381
0.8606	High Similarity	NPC199533
0.86	High Similarity	NPC182421
0.86	High Similarity	NPC220106
0.8599	High Similarity	NPC472909
0.8599	High Similarity	NPC166054
0.8599	High Similarity	NPC89625
0.8599	High Similarity	NPC67396
0.8599	High Similarity	NPC37392
0.8599	High Similarity	NPC149618
0.8599	High Similarity	NPC55662
0.8598	High Similarity	NPC477836
0.8598	High Similarity	NPC158226
0.8591	High Similarity	NPC1268
0.859	High Similarity	NPC167903
0.8581	High Similarity	NPC158866
0.8581	High Similarity	NPC475717
0.8581	High Similarity	NPC120105
0.8581	High Similarity	NPC474660

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 NPC281272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	964
0.2-0.3	1691
0.3-0.4	2579
0.4-0.5	1949
0.5-0.6	1058
0.6-0.7	327
0.7-0.8	145
0.8-0.85	46
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD7819	Suspended
0.8649	High Similarity	NPD2346	Discontinued
0.8636	High Similarity	NPD3226	Approved
0.8581	High Similarity	NPD1551	Phase 2
0.8481	Intermediate Similarity	NPD5402	Approved
0.8477	Intermediate Similarity	NPD3750	Approved
0.84	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8377	Intermediate Similarity	NPD2532	Approved
0.8377	Intermediate Similarity	NPD2533	Approved
0.8377	Intermediate Similarity	NPD2534	Approved
0.8364	Intermediate Similarity	NPD5844	Phase 1
0.8355	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD1934	Approved
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8302	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD2801	Approved
0.8261	Intermediate Similarity	NPD3749	Approved
0.8258	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2935	Discontinued
0.8176	Intermediate Similarity	NPD7411	Suspended
0.8148	Intermediate Similarity	NPD7075	Discontinued
0.8146	Intermediate Similarity	NPD3748	Approved
0.8146	Intermediate Similarity	NPD1510	Phase 2
0.8133	Intermediate Similarity	NPD1607	Approved
0.8117	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.8107	Intermediate Similarity	NPD6559	Discontinued
0.8103	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7768	Phase 2
0.8077	Intermediate Similarity	NPD1511	Approved
0.8075	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5403	Approved
0.8037	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5401	Approved
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.8012	Intermediate Similarity	NPD8313	Approved
0.8012	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD2313	Discontinued
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1512	Approved
0.7974	Intermediate Similarity	NPD2796	Approved
0.7974	Intermediate Similarity	NPD6100	Approved
0.7974	Intermediate Similarity	NPD6099	Approved
0.7964	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6166	Phase 2
0.7964	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6799	Approved
0.7939	Intermediate Similarity	NPD5494	Approved
0.7911	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6801	Discontinued
0.7891	Intermediate Similarity	NPD1203	Approved
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.787	Intermediate Similarity	NPD3818	Discontinued
0.7866	Intermediate Similarity	NPD3882	Suspended
0.7853	Intermediate Similarity	NPD1465	Phase 2
0.7844	Intermediate Similarity	NPD5710	Approved
0.7844	Intermediate Similarity	NPD5711	Approved
0.7829	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7054	Approved
0.78	Intermediate Similarity	NPD4625	Phase 3
0.7799	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7792	Intermediate Similarity	NPD4308	Phase 3
0.7778	Intermediate Similarity	NPD7472	Approved
0.7771	Intermediate Similarity	NPD4628	Phase 3
0.777	Intermediate Similarity	NPD1470	Approved
0.7765	Intermediate Similarity	NPD3751	Discontinued
0.7748	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD411	Approved
0.7733	Intermediate Similarity	NPD6797	Phase 2
0.7733	Intermediate Similarity	NPD6832	Phase 2
0.7719	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD447	Suspended
0.7707	Intermediate Similarity	NPD2800	Approved
0.7707	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD920	Approved
0.7688	Intermediate Similarity	NPD7251	Discontinued
0.7687	Intermediate Similarity	NPD9717	Approved
0.7663	Intermediate Similarity	NPD7435	Discontinued
0.7651	Intermediate Similarity	NPD2797	Approved
0.7644	Intermediate Similarity	NPD7808	Phase 3
0.7632	Intermediate Similarity	NPD3268	Approved
0.7632	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5953	Discontinued
0.7619	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1201	Approved
0.7596	Intermediate Similarity	NPD6781	Approved
0.7596	Intermediate Similarity	NPD6776	Approved
0.7596	Intermediate Similarity	NPD6777	Approved
0.7596	Intermediate Similarity	NPD6782	Approved
0.7596	Intermediate Similarity	NPD6779	Approved
0.7596	Intermediate Similarity	NPD6778	Approved
0.7596	Intermediate Similarity	NPD6780	Approved
0.7584	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2344	Approved
0.7578	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6844	Discontinued
0.7576	Intermediate Similarity	NPD37	Approved
0.7571	Intermediate Similarity	NPD8150	Discontinued
0.7568	Intermediate Similarity	NPD1608	Approved
0.7564	Intermediate Similarity	NPD7033	Discontinued
0.7545	Intermediate Similarity	NPD4967	Phase 2
0.7545	Intermediate Similarity	NPD4965	Approved
0.7545	Intermediate Similarity	NPD4966	Approved
0.7532	Intermediate Similarity	NPD4307	Phase 2
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7517	Intermediate Similarity	NPD4749	Approved
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7516	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5406	Approved
0.7516	Intermediate Similarity	NPD3764	Approved
0.7516	Intermediate Similarity	NPD5408	Approved
0.7516	Intermediate Similarity	NPD5404	Approved
0.7516	Intermediate Similarity	NPD5405	Approved
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7485	Intermediate Similarity	NPD4288	Approved
0.7484	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7483	Intermediate Similarity	NPD2798	Approved
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.7473	Intermediate Similarity	NPD7697	Approved
0.7473	Intermediate Similarity	NPD7698	Approved
0.7472	Intermediate Similarity	NPD8434	Phase 2
0.7456	Intermediate Similarity	NPD6234	Discontinued
0.7453	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7871	Phase 2
0.7433	Intermediate Similarity	NPD7870	Phase 2
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7423	Intermediate Similarity	NPD6273	Approved
0.7421	Intermediate Similarity	NPD7874	Approved
0.7421	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1613	Approved
0.7419	Intermediate Similarity	NPD6823	Phase 2
0.7417	Intermediate Similarity	NPD3266	Approved
0.7417	Intermediate Similarity	NPD3267	Approved
0.741	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2309	Approved
0.7383	Intermediate Similarity	NPD1611	Approved
0.7383	Intermediate Similarity	NPD422	Phase 1
0.7382	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7783	Phase 2
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD1019	Discontinued
0.7368	Intermediate Similarity	NPD8151	Discontinued
0.7368	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD1247	Approved
0.7365	Intermediate Similarity	NPD17	Approved
0.7356	Intermediate Similarity	NPD7228	Approved
0.7356	Intermediate Similarity	NPD7177	Discontinued
0.7353	Intermediate Similarity	NPD919	Approved
0.7351	Intermediate Similarity	NPD1283	Approved
0.7351	Intermediate Similarity	NPD3225	Approved
0.7345	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD9493	Approved
0.7329	Intermediate Similarity	NPD7003	Approved
0.7322	Intermediate Similarity	NPD6534	Approved
0.7322	Intermediate Similarity	NPD6535	Approved
0.732	Intermediate Similarity	NPD2861	Phase 2
0.7316	Intermediate Similarity	NPD7701	Phase 2
0.7315	Intermediate Similarity	NPD3496	Discontinued
0.731	Intermediate Similarity	NPD6746	Phase 2
0.7308	Intermediate Similarity	NPD943	Approved
0.7293	Intermediate Similarity	NPD4287	Approved
0.7283	Intermediate Similarity	NPD3926	Phase 2
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5124	Phase 1
0.725	Intermediate Similarity	NPD1471	Phase 3
0.7248	Intermediate Similarity	NPD1778	Approved
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7229	Intermediate Similarity	NPD1653	Approved
0.7219	Intermediate Similarity	NPD1481	Phase 2
0.7211	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7699	Phase 2
0.7204	Intermediate Similarity	NPD7700	Phase 2
0.7202	Intermediate Similarity	NPD7801	Approved
0.7197	Intermediate Similarity	NPD4060	Phase 1
0.7197	Intermediate Similarity	NPD2979	Phase 3
0.7184	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7985	Registered
0.7174	Intermediate Similarity	NPD6212	Phase 3

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