NPASS Compound

Structure

NPC186113 OpenBabel07101719122D 30 33 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 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 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 -1.7321 -1.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 2.5981 3.5000 0.0000 C 0 0 2 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 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 2 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 2.5981 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 12 2 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 29 1 0 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 16 13 1 1 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 27 1 6 0 0 0 23 28 2 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.18
Volume:	426.953
LogP:	5.79
LogD:	3.453
LogS:	-3.898
# Rotatable Bonds:	3
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	4.031
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.837
MDCK Permeability:	1.1103959877800662e-05
Pgp-inhibitor:	0.786
Pgp-substrate:	0.5
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	0.39
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	86.6405258178711%
Volume Distribution (VD):	0.932
Pgp-substrate:	9.683526992797852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.702
CYP1A2-substrate:	0.67
CYP2C19-inhibitor:	0.82
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.632
CYP2D6-substrate:	0.32
CYP3A4-inhibitor:	0.299
CYP3A4-substrate:	0.142

ADMET: Excretion

Clearance (CL):	2.004
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.934
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.531
Rat Oral Acute Toxicity:	0.403
Maximum Recommended Daily Dose:	0.812
Skin Sensitization:	0.504
Carcinogencity:	0.841
Eye Corrosion:	0.003
Eye Irritation:	0.214
Respiratory Toxicity:	0.197

Download Data

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

Natural Product: NPC186113

Natural Product ID:	NPC186113
*Common Name:**	Shamixanthone
IUPAC Name:	(1R,2S)-1,11-dihydroxy-5-methyl-8-(3-methylbut-2-enyl)-2-prop-1-en-2-yl-2,3-dihydro-1H-pyrano[3,2-a]xanthen-12-one
Synonyms:	Shamixanthone
Standard InCHIKey:	MXGMZMKTWCNKRS-OPAMFIHVSA-N
Standard InCHI:	InChI=1S/C25H26O5/c1-12(2)6-7-15-8-9-17(26)19-23(28)20-18(30-25(15)19)10-14(5)24-21(20)22(27)16(11-29-24)13(3)4/h6,8-10,16,22,26-27H,3,7,11H2,1-2,4-5H3/t16-,22-/m1/s1
SMILES:	CC(=CCc1ccc(c2c1oc1cc(C)c3c(c1c2=O)[C@H](O)[C@H](CO3)C(=C)C)O)C
Synthetic Gene Cluster:	BGC0000101;
ChEMBL Identifier:	CHEMBL469860
PubChem CID:	15596091
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 [CHEMONTID:0003518] 4-prenylated 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
NPO27885.1	Aspergillus nidulans var. acristatus	Varieties	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872131]
NPO33058	emericella sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17323993]
NPO33058	emericella sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19013822]
NPO27885.1	Aspergillus nidulans var. acristatus	Varieties	Aspergillaceae	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
Kd	1
Ki	1
MIC	4

Activity Type	# Activity
Individual Protein	1
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1621	Individual Protein	Calmodulin	Homo sapiens	IC50	=	29160.0	nM	PMID[536128]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	50.0	ug.mL-1	PMID[536126]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[536126]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[536126]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	50.0	ug.mL-1	PMID[536126]
NPT2	Others	Unspecified		Kd	=	28.8	nM	PMID[536130]
NPT2	Others	Unspecified		Ki	=	83.0	nM	PMID[536130]

☑ 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 NPC186113 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	430
0.1-0.2	1615
0.2-0.3	3567
0.3-0.4	8827
0.4-0.5	9845
0.5-0.6	3695
0.6-0.7	5452
0.7-0.8	4807
0.8-0.85	2740
0.85-0.9	1554
0.9-0.95	160
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC473961
0.9733	High Similarity	NPC135522
0.9554	High Similarity	NPC225419
0.9434	High Similarity	NPC241874
0.9434	High Similarity	NPC474004
0.9408	High Similarity	NPC474843
0.9333	High Similarity	NPC71055
0.929	High Similarity	NPC44199
0.9281	High Similarity	NPC87708
0.9276	High Similarity	NPC202595
0.9276	High Similarity	NPC227122
0.9245	High Similarity	NPC178173
0.9221	High Similarity	NPC95842
0.9221	High Similarity	NPC280530
0.9221	High Similarity	NPC178964
0.9216	High Similarity	NPC72958
0.9216	High Similarity	NPC232645
0.9182	High Similarity	NPC25361
0.9172	High Similarity	NPC471976
0.9156	High Similarity	NPC281272
0.915	High Similarity	NPC37348
0.9145	High Similarity	NPC5537
0.9139	High Similarity	NPC469758
0.9119	High Similarity	NPC197168
0.9114	High Similarity	NPC18380
0.9114	High Similarity	NPC3629
0.9085	High Similarity	NPC266499
0.9085	High Similarity	NPC473016
0.9079	High Similarity	NPC308200
0.9073	High Similarity	NPC469764
0.9068	High Similarity	NPC117854
0.9068	High Similarity	NPC6588
0.9068	High Similarity	NPC477154
0.9057	High Similarity	NPC472402
0.9057	High Similarity	NPC15374
0.9051	High Similarity	NPC184326
0.9051	High Similarity	NPC292863
0.9045	High Similarity	NPC281137
0.9045	High Similarity	NPC282390
0.9038	High Similarity	NPC55662
0.9038	High Similarity	NPC166054
0.9032	High Similarity	NPC154683
0.9032	High Similarity	NPC40356
0.9026	High Similarity	NPC29777
0.9026	High Similarity	NPC471115
0.9026	High Similarity	NPC472633
0.902	High Similarity	NPC37135
0.902	High Similarity	NPC39195
0.902	High Similarity	NPC145467
0.902	High Similarity	NPC186397
0.9013	High Similarity	NPC290133
0.9013	High Similarity	NPC24136
0.9013	High Similarity	NPC187282
0.9013	High Similarity	NPC472629
0.9006	High Similarity	NPC128293
0.9006	High Similarity	NPC120593
0.9	High Similarity	NPC207690
0.9	High Similarity	NPC273959
0.9	High Similarity	NPC290160
0.8994	High Similarity	NPC474187
0.8994	High Similarity	NPC137232
0.8994	High Similarity	NPC474186
0.8987	High Similarity	NPC195167
0.8987	High Similarity	NPC329091
0.8987	High Similarity	NPC85121
0.8981	High Similarity	NPC164427
0.8974	High Similarity	NPC193200
0.8974	High Similarity	NPC210942
0.8974	High Similarity	NPC329844
0.8974	High Similarity	NPC169990
0.897	High Similarity	NPC324220
0.897	High Similarity	NPC312630
0.8968	High Similarity	NPC470675
0.8968	High Similarity	NPC46564
0.8968	High Similarity	NPC39819
0.8968	High Similarity	NPC207346
0.8968	High Similarity	NPC149526
0.8968	High Similarity	NPC478148
0.8968	High Similarity	NPC470569
0.8968	High Similarity	NPC473131
0.8968	High Similarity	NPC474417
0.8963	High Similarity	NPC154986
0.8961	High Similarity	NPC97029
0.8961	High Similarity	NPC223988
0.8961	High Similarity	NPC288036
0.8961	High Similarity	NPC65589
0.8961	High Similarity	NPC471114
0.8961	High Similarity	NPC158338
0.8961	High Similarity	NPC100985
0.8961	High Similarity	NPC97028
0.8951	High Similarity	NPC474024
0.8947	High Similarity	NPC87486
0.8947	High Similarity	NPC311144
0.8947	High Similarity	NPC124780
0.8947	High Similarity	NPC470890
0.8947	High Similarity	NPC271288
0.8938	High Similarity	NPC229632
0.8931	High Similarity	NPC474287
0.8931	High Similarity	NPC470810
0.8931	High Similarity	NPC119224
0.8931	High Similarity	NPC475886
0.8931	High Similarity	NPC321399
0.8931	High Similarity	NPC472618
0.8924	High Similarity	NPC165977
0.8924	High Similarity	NPC196448
0.8924	High Similarity	NPC272196
0.8924	High Similarity	NPC217677
0.8924	High Similarity	NPC475184
0.8917	High Similarity	NPC175192
0.891	High Similarity	NPC273483
0.891	High Similarity	NPC475790
0.8903	High Similarity	NPC290954
0.8903	High Similarity	NPC294646
0.8903	High Similarity	NPC470568
0.8903	High Similarity	NPC255641
0.8903	High Similarity	NPC147735
0.8903	High Similarity	NPC101957
0.8903	High Similarity	NPC120105
0.8896	High Similarity	NPC7025
0.8896	High Similarity	NPC106328
0.8896	High Similarity	NPC27221
0.8896	High Similarity	NPC256672
0.8896	High Similarity	NPC35150
0.8889	High Similarity	NPC43319
0.8889	High Similarity	NPC470676
0.8889	High Similarity	NPC272502
0.8889	High Similarity	NPC299011
0.8889	High Similarity	NPC473132
0.8889	High Similarity	NPC37870
0.8889	High Similarity	NPC473135
0.8889	High Similarity	NPC251336
0.8882	High Similarity	NPC77794
0.8882	High Similarity	NPC85162
0.8882	High Similarity	NPC125894
0.8882	High Similarity	NPC223812
0.8882	High Similarity	NPC152659
0.8882	High Similarity	NPC278249
0.8882	High Similarity	NPC248638
0.8882	High Similarity	NPC81697
0.8882	High Similarity	NPC7483
0.8882	High Similarity	NPC113770
0.8882	High Similarity	NPC107177
0.8882	High Similarity	NPC236521
0.8882	High Similarity	NPC236132
0.8875	High Similarity	NPC66288
0.8875	High Similarity	NPC475883
0.8875	High Similarity	NPC32694
0.8875	High Similarity	NPC474351
0.8868	High Similarity	NPC210459
0.8868	High Similarity	NPC226287
0.8868	High Similarity	NPC324736
0.8868	High Similarity	NPC472617
0.8868	High Similarity	NPC51760
0.8861	High Similarity	NPC69531
0.8861	High Similarity	NPC78492
0.8861	High Similarity	NPC208152
0.8861	High Similarity	NPC142339
0.8855	High Similarity	NPC475246
0.8854	High Similarity	NPC477691
0.8846	High Similarity	NPC312549
0.8846	High Similarity	NPC474023
0.8846	High Similarity	NPC209142
0.8846	High Similarity	NPC178484
0.8846	High Similarity	NPC474021
0.8841	High Similarity	NPC477572
0.8841	High Similarity	NPC477573
0.8841	High Similarity	NPC477571
0.8841	High Similarity	NPC251144
0.8841	High Similarity	NPC103307
0.8841	High Similarity	NPC241387
0.8839	High Similarity	NPC70764
0.8839	High Similarity	NPC65775
0.8839	High Similarity	NPC329933
0.8839	High Similarity	NPC10027
0.8839	High Similarity	NPC5173
0.8834	High Similarity	NPC218226
0.8831	High Similarity	NPC473077
0.8831	High Similarity	NPC300988
0.8831	High Similarity	NPC296998
0.8831	High Similarity	NPC7943
0.8831	High Similarity	NPC22005
0.8831	High Similarity	NPC10990
0.8831	High Similarity	NPC123202
0.8827	High Similarity	NPC473286
0.8827	High Similarity	NPC239752
0.8827	High Similarity	NPC472450
0.8827	High Similarity	NPC326520
0.8827	High Similarity	NPC275780
0.8827	High Similarity	NPC469664
0.8827	High Similarity	NPC293319
0.8824	High Similarity	NPC473015
0.8824	High Similarity	NPC131568
0.8824	High Similarity	NPC224714
0.8824	High Similarity	NPC184649
0.8824	High Similarity	NPC131579
0.8824	High Similarity	NPC473013
0.8824	High Similarity	NPC303185
0.8824	High Similarity	NPC235217
0.8824	High Similarity	NPC473014
0.882	High Similarity	NPC329760

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 NPC186113 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	966
0.2-0.3	1588
0.3-0.4	2614
0.4-0.5	1966
0.5-0.6	1020
0.6-0.7	399
0.7-0.8	163
0.8-0.85	43
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8994	High Similarity	NPD6959	Discontinued
0.8734	High Similarity	NPD2393	Clinical (unspecified phase)
0.8696	High Similarity	NPD5494	Approved
0.8679	High Similarity	NPD8443	Clinical (unspecified phase)
0.8616	High Similarity	NPD7819	Suspended
0.8581	High Similarity	NPD4378	Clinical (unspecified phase)
0.8554	High Similarity	NPD5844	Phase 1
0.8544	High Similarity	NPD4380	Phase 2
0.8487	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD1934	Approved
0.8431	Intermediate Similarity	NPD1549	Phase 2
0.8385	Intermediate Similarity	NPD2801	Approved
0.8373	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD6166	Phase 2
0.8344	Intermediate Similarity	NPD2533	Approved
0.8344	Intermediate Similarity	NPD2532	Approved
0.8344	Intermediate Similarity	NPD2534	Approved
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8294	Intermediate Similarity	NPD6559	Discontinued
0.8261	Intermediate Similarity	NPD7411	Suspended
0.8253	Intermediate Similarity	NPD6232	Discontinued
0.8247	Intermediate Similarity	NPD2346	Discontinued
0.8232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7075	Discontinued
0.8228	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5402	Approved
0.8205	Intermediate Similarity	NPD3750	Approved
0.8198	Intermediate Similarity	NPD8312	Approved
0.8198	Intermediate Similarity	NPD8313	Approved
0.8182	Intermediate Similarity	NPD2796	Approved
0.8182	Intermediate Similarity	NPD2935	Discontinued
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8171	Intermediate Similarity	NPD7768	Phase 2
0.816	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3226	Approved
0.8118	Intermediate Similarity	NPD7054	Approved
0.8117	Intermediate Similarity	NPD1510	Phase 2
0.8105	Intermediate Similarity	NPD1607	Approved
0.8079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7472	Approved
0.805	Intermediate Similarity	NPD1511	Approved
0.8047	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6801	Discontinued
0.7977	Intermediate Similarity	NPD7251	Discontinued
0.7974	Intermediate Similarity	NPD1240	Approved
0.7961	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3818	Discontinued
0.7952	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3882	Suspended
0.795	Intermediate Similarity	NPD1512	Approved
0.7949	Intermediate Similarity	NPD6099	Approved
0.7949	Intermediate Similarity	NPD6100	Approved
0.7949	Intermediate Similarity	NPD1551	Phase 2
0.7937	Intermediate Similarity	NPD7390	Discontinued
0.7931	Intermediate Similarity	NPD7808	Phase 3
0.7911	Intermediate Similarity	NPD2800	Approved
0.7895	Intermediate Similarity	NPD4625	Phase 3
0.7885	Intermediate Similarity	NPD3748	Approved
0.7885	Intermediate Similarity	NPD2799	Discontinued
0.7866	Intermediate Similarity	NPD6599	Discontinued
0.7862	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4908	Phase 1
0.7824	Intermediate Similarity	NPD5711	Approved
0.7824	Intermediate Similarity	NPD5710	Approved
0.7791	Intermediate Similarity	NPD5403	Approved
0.7784	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD6777	Approved
0.7772	Intermediate Similarity	NPD6776	Approved
0.7772	Intermediate Similarity	NPD6779	Approved
0.7772	Intermediate Similarity	NPD6778	Approved
0.7772	Intermediate Similarity	NPD6781	Approved
0.7772	Intermediate Similarity	NPD6782	Approved
0.7772	Intermediate Similarity	NPD6780	Approved
0.7765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7697	Approved
0.7742	Intermediate Similarity	NPD7696	Phase 3
0.7742	Intermediate Similarity	NPD7698	Approved
0.7727	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD1465	Phase 2
0.7716	Intermediate Similarity	NPD6799	Approved
0.7714	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4363	Phase 3
0.7692	Intermediate Similarity	NPD4360	Phase 2
0.7688	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6823	Phase 2
0.7669	Intermediate Similarity	NPD5401	Approved
0.7665	Intermediate Similarity	NPD6844	Discontinued
0.7665	Intermediate Similarity	NPD37	Approved
0.7654	Intermediate Similarity	NPD8150	Discontinued
0.7647	Intermediate Similarity	NPD2861	Phase 2
0.7647	Intermediate Similarity	NPD7435	Discontinued
0.7644	Intermediate Similarity	NPD7783	Phase 2
0.7644	Intermediate Similarity	NPD7228	Approved
0.7644	Intermediate Similarity	NPD3751	Discontinued
0.7644	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4628	Phase 3
0.7633	Intermediate Similarity	NPD4966	Approved
0.7633	Intermediate Similarity	NPD4965	Approved
0.7633	Intermediate Similarity	NPD4967	Phase 2
0.7622	Intermediate Similarity	NPD6273	Approved
0.7616	Intermediate Similarity	NPD3787	Discontinued
0.7613	Intermediate Similarity	NPD2313	Discontinued
0.7613	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5406	Approved
0.761	Intermediate Similarity	NPD5408	Approved
0.761	Intermediate Similarity	NPD5405	Approved
0.761	Intermediate Similarity	NPD5404	Approved
0.7606	Intermediate Similarity	NPD7870	Phase 2
0.7606	Intermediate Similarity	NPD7871	Phase 2
0.7605	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1610	Phase 2
0.758	Intermediate Similarity	NPD5124	Phase 1
0.758	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7701	Phase 2
0.7578	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD920	Approved
0.7561	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD1247	Approved
0.7544	Intermediate Similarity	NPD6234	Discontinued
0.7539	Intermediate Similarity	NPD8151	Discontinued
0.7532	Intermediate Similarity	NPD6651	Approved
0.7531	Intermediate Similarity	NPD7003	Approved
0.7516	Intermediate Similarity	NPD1613	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1470	Approved
0.7514	Intermediate Similarity	NPD7229	Phase 3
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7483	Intermediate Similarity	NPD1201	Approved
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7700	Phase 2
0.7473	Intermediate Similarity	NPD7699	Phase 2
0.7461	Intermediate Similarity	NPD7801	Approved
0.7455	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2344	Approved
0.7409	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7874	Approved
0.7394	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.7362	Intermediate Similarity	NPD1243	Approved
0.7355	Intermediate Similarity	NPD2798	Approved
0.7338	Intermediate Similarity	NPD1283	Approved
0.7333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5761	Phase 2
0.731	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD5760	Phase 2
0.7308	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4060	Phase 1
0.7296	Intermediate Similarity	NPD2979	Phase 3
0.7296	Intermediate Similarity	NPD943	Approved
0.729	Intermediate Similarity	NPD1203	Approved
0.729	Intermediate Similarity	NPD2797	Approved
0.7285	Intermediate Similarity	NPD1651	Approved
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7278	Intermediate Similarity	NPD7240	Approved
0.7273	Intermediate Similarity	NPD4361	Phase 2
0.7273	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3926	Phase 2
0.7273	Intermediate Similarity	NPD2309	Approved
0.7267	Intermediate Similarity	NPD4288	Approved
0.7261	Intermediate Similarity	NPD6832	Phase 2
0.7261	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6213	Phase 3
0.7258	Intermediate Similarity	NPD6212	Phase 3
0.7258	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7199	Phase 2
0.725	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7177	Discontinued
0.7244	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD919	Approved
0.724	Intermediate Similarity	NPD8320	Phase 1
0.724	Intermediate Similarity	NPD8319	Approved
0.7239	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7222	Intermediate Similarity	NPD4308	Phase 3
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7215	Intermediate Similarity	NPD3027	Phase 3
0.7197	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2424	Discontinued
0.7178	Intermediate Similarity	NPD2438	Suspended
0.717	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD411	Approved
0.7152	Intermediate Similarity	NPD6674	Discontinued

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