NPASS Compound

Structure

NPC312789 OpenBabel07101719242D 22 23 0 0 0 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 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 1.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 3.4641 0.0000 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 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 3 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 19 2 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.13
Volume:	313.608
LogP:	3.683
LogD:	3.153
LogS:	-3.463
# Rotatable Bonds:	7
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	2.558
Fsp3:	0.412
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:	-4.735
MDCK Permeability:	2.7118501748191193e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.711
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.168
30% Bioavailability (F30%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	93.70052337646484%
Volume Distribution (VD):	0.654
Pgp-substrate:	10.533496856689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.842
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.276
CYP2C9-inhibitor:	0.883
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.492
CYP2D6-substrate:	0.718
CYP3A4-inhibitor:	0.723
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	6.964
Half-life (T1/2):	0.868

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.461
AMES Toxicity:	0.455
Rat Oral Acute Toxicity:	0.496
Maximum Recommended Daily Dose:	0.625
Skin Sensitization:	0.535
Carcinogencity:	0.056
Eye Corrosion:	0.013
Eye Irritation:	0.197
Respiratory Toxicity:	0.252

Download Data

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

Natural Product: NPC312789

Natural Product ID:	NPC312789
*Common Name:**	Pestalotiopsone F
IUPAC Name:	methyl 2-(7-hydroxy-4-oxo-2-pentylchromen-5-yl)acetate
Synonyms:	pestalotiopsone F
Standard InCHIKey:	LHRHJRDQHAXPSQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O5/c1-3-4-5-6-13-10-14(19)17-11(8-16(20)21-2)7-12(18)9-15(17)22-13/h7,9-10,18H,3-6,8H2,1-2H3
SMILES:	CCCCCc1cc(=O)c2c(o1)cc(cc2CC(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL554131
PubChem CID:	42638627
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19117486]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	chinese mangrove plant Rhizophora mucronata	n.a.	n.a.	PMID[19271764]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	Chinese mangrove plant Rhizophoramucronata	n.a.	n.a.	PMID[19762244]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	Isolated from the branches of Podocarpus macrophyllus	Kunming World Horticultural Exposition Garden, Kunming, China	2002-NOV	PMID[21302965]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24168147]

☑ 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
EC50	1
MIC	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	EC50	=	8.93	ug.mL-1	PMID[538899]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	9.0	ug.mL-1	PMID[538900]
NPT4619	Organism	Raoultella planticola	Raoultella planticola	MIC	=	9.0	ug.mL-1	PMID[538900]

☑ 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 NPC312789 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	356
0.1-0.2	1646
0.2-0.3	3967
0.3-0.4	9602
0.4-0.5	8915
0.5-0.6	3675
0.6-0.7	5656
0.7-0.8	5022
0.8-0.85	2774
0.85-0.9	914
0.9-0.95	154
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC240253
0.9787	High Similarity	NPC240622
0.9787	High Similarity	NPC471641
0.9787	High Similarity	NPC471642
0.9565	High Similarity	NPC57380
0.9514	High Similarity	NPC60413
0.9504	High Similarity	NPC95123
0.9504	High Similarity	NPC66404
0.95	High Similarity	NPC471644
0.95	High Similarity	NPC471640
0.9444	High Similarity	NPC6923
0.9437	High Similarity	NPC472034
0.9437	High Similarity	NPC134621
0.9371	High Similarity	NPC237208
0.9371	High Similarity	NPC472033
0.9362	High Similarity	NPC105648
0.9348	High Similarity	NPC242712
0.9306	High Similarity	NPC472036
0.9301	High Similarity	NPC29577
0.9296	High Similarity	NPC478202
0.9296	High Similarity	NPC471639
0.9296	High Similarity	NPC472006
0.9296	High Similarity	NPC471643
0.9291	High Similarity	NPC220106
0.9291	High Similarity	NPC1704
0.9291	High Similarity	NPC67650
0.9286	High Similarity	NPC92655
0.9281	High Similarity	NPC135837
0.9275	High Similarity	NPC180905
0.9275	High Similarity	NPC182496
0.9247	High Similarity	NPC295036
0.9247	High Similarity	NPC158866
0.9241	High Similarity	NPC37139
0.9225	High Similarity	NPC474385
0.9225	High Similarity	NPC250755
0.9203	High Similarity	NPC175943
0.9184	High Similarity	NPC133856
0.9178	High Similarity	NPC473978
0.9178	High Similarity	NPC291049
0.9178	High Similarity	NPC233267
0.9172	High Similarity	NPC259632
0.9172	High Similarity	NPC12305
0.9167	High Similarity	NPC473692
0.9161	High Similarity	NPC51106
0.9161	High Similarity	NPC310340
0.9161	High Similarity	NPC469542
0.9155	High Similarity	NPC478201
0.9155	High Similarity	NPC16455
0.9155	High Similarity	NPC158634
0.9155	High Similarity	NPC307990
0.9155	High Similarity	NPC478217
0.9155	High Similarity	NPC475730
0.9155	High Similarity	NPC313123
0.9155	High Similarity	NPC472035
0.9149	High Similarity	NPC32360
0.9149	High Similarity	NPC268052
0.913	High Similarity	NPC10971
0.911	High Similarity	NPC153417
0.911	High Similarity	NPC105415
0.9103	High Similarity	NPC267509
0.9103	High Similarity	NPC107625
0.9097	High Similarity	NPC277426
0.9097	High Similarity	NPC210425
0.9097	High Similarity	NPC280404
0.9097	High Similarity	NPC86373
0.9091	High Similarity	NPC469579
0.9091	High Similarity	NPC96692
0.9078	High Similarity	NPC33144
0.9078	High Similarity	NPC191835
0.9078	High Similarity	NPC478200
0.9058	High Similarity	NPC31872
0.9058	High Similarity	NPC473584
0.9058	High Similarity	NPC475589
0.9048	High Similarity	NPC97028
0.9048	High Similarity	NPC288036
0.9048	High Similarity	NPC97029
0.9048	High Similarity	NPC100985
0.9048	High Similarity	NPC158338
0.9048	High Similarity	NPC65589
0.9041	High Similarity	NPC210320
0.9034	High Similarity	NPC32470
0.9021	High Similarity	NPC90411
0.9021	High Similarity	NPC275734
0.9014	High Similarity	NPC131130
0.9007	High Similarity	NPC178467
0.9007	High Similarity	NPC174999
0.9007	High Similarity	NPC263483
0.9007	High Similarity	NPC474771
0.9007	High Similarity	NPC149372
0.9007	High Similarity	NPC474849
0.9007	High Similarity	NPC65837
0.9007	High Similarity	NPC70380
0.9	High Similarity	NPC89625
0.9	High Similarity	NPC149618
0.8993	High Similarity	NPC273483
0.8993	High Similarity	NPC25937
0.8993	High Similarity	NPC153783
0.8993	High Similarity	NPC203817
0.8986	High Similarity	NPC307780
0.8986	High Similarity	NPC219892
0.8986	High Similarity	NPC189823
0.8986	High Similarity	NPC150928
0.8986	High Similarity	NPC309979
0.8986	High Similarity	NPC470107
0.8986	High Similarity	NPC5515
0.8986	High Similarity	NPC270369
0.898	High Similarity	NPC2569
0.898	High Similarity	NPC256672
0.898	High Similarity	NPC27221
0.898	High Similarity	NPC73411
0.898	High Similarity	NPC172329
0.898	High Similarity	NPC215711
0.898	High Similarity	NPC7025
0.8973	High Similarity	NPC225173
0.8973	High Similarity	NPC163846
0.8966	High Similarity	NPC126882
0.8966	High Similarity	NPC478203
0.8966	High Similarity	NPC210966
0.8958	High Similarity	NPC49108
0.8951	High Similarity	NPC165172
0.8951	High Similarity	NPC230902
0.8944	High Similarity	NPC94248
0.8944	High Similarity	NPC472602
0.8944	High Similarity	NPC177307
0.8944	High Similarity	NPC9121
0.8944	High Similarity	NPC472403
0.8944	High Similarity	NPC475974
0.8944	High Similarity	NPC212693
0.8936	High Similarity	NPC50455
0.8936	High Similarity	NPC235115
0.8933	High Similarity	NPC472799
0.8929	High Similarity	NPC223457
0.8919	High Similarity	NPC10027
0.8919	High Similarity	NPC65775
0.8919	High Similarity	NPC476684
0.8912	High Similarity	NPC14098
0.8912	High Similarity	NPC22005
0.8912	High Similarity	NPC125801
0.8912	High Similarity	NPC7943
0.8912	High Similarity	NPC123202
0.8904	High Similarity	NPC257558
0.8889	High Similarity	NPC53649
0.8889	High Similarity	NPC243701
0.8889	High Similarity	NPC472603
0.8881	High Similarity	NPC199458
0.8881	High Similarity	NPC247409
0.8881	High Similarity	NPC183639
0.8873	High Similarity	NPC29353
0.8873	High Similarity	NPC234133
0.8873	High Similarity	NPC47815
0.8873	High Similarity	NPC476333
0.8873	High Similarity	NPC473887
0.8873	High Similarity	NPC473391
0.8873	High Similarity	NPC194281
0.8873	High Similarity	NPC127447
0.8873	High Similarity	NPC472364
0.8873	High Similarity	NPC231772
0.8873	High Similarity	NPC472367
0.8873	High Similarity	NPC124784
0.8873	High Similarity	NPC194579
0.8873	High Similarity	NPC13408
0.8867	High Similarity	NPC271681
0.8867	High Similarity	NPC217447
0.8865	High Similarity	NPC125920
0.8865	High Similarity	NPC236974
0.8865	High Similarity	NPC144027
0.8865	High Similarity	NPC298900
0.8844	High Similarity	NPC473927
0.8844	High Similarity	NPC470322
0.8844	High Similarity	NPC154217
0.8836	High Similarity	NPC470216
0.8819	High Similarity	NPC472600
0.8819	High Similarity	NPC139554
0.8819	High Similarity	NPC158472
0.8819	High Similarity	NPC19476
0.8819	High Similarity	NPC23257
0.8819	High Similarity	NPC472601
0.8819	High Similarity	NPC241975
0.8816	High Similarity	NPC4547
0.8816	High Similarity	NPC146211
0.8816	High Similarity	NPC54928
0.8811	High Similarity	NPC474624
0.8811	High Similarity	NPC250266
0.8811	High Similarity	NPC266597
0.8811	High Similarity	NPC188879
0.8811	High Similarity	NPC138047
0.8811	High Similarity	NPC131782
0.8808	High Similarity	NPC329844
0.8808	High Similarity	NPC169990
0.8808	High Similarity	NPC210942
0.8808	High Similarity	NPC214632
0.8803	High Similarity	NPC60667
0.88	High Similarity	NPC232645
0.88	High Similarity	NPC227166
0.88	High Similarity	NPC215921
0.88	High Similarity	NPC478148
0.88	High Similarity	NPC72958
0.88	High Similarity	NPC70016
0.88	High Similarity	NPC106372
0.88	High Similarity	NPC58668

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 NPC312789 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	1001
0.2-0.3	1688
0.3-0.4	2574
0.4-0.5	1846
0.5-0.6	1142
0.6-0.7	388
0.7-0.8	129
0.8-0.85	52
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9424	High Similarity	NPD970	Clinical (unspecified phase)
0.8808	High Similarity	NPD7819	Suspended
0.8649	High Similarity	NPD2534	Approved
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8649	High Similarity	NPD2533	Approved
0.8649	High Similarity	NPD2532	Approved
0.863	High Similarity	NPD3750	Approved
0.8553	High Similarity	NPD7411	Suspended
0.8456	Intermediate Similarity	NPD6799	Approved
0.8456	Intermediate Similarity	NPD1511	Approved
0.8442	Intermediate Similarity	NPD2801	Approved
0.8425	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1510	Phase 2
0.8392	Intermediate Similarity	NPD1240	Approved
0.8387	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD3817	Phase 2
0.8367	Intermediate Similarity	NPD1549	Phase 2
0.8356	Intermediate Similarity	NPD2796	Approved
0.8344	Intermediate Similarity	NPD1512	Approved
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD3748	Approved
0.828	Intermediate Similarity	NPD7075	Discontinued
0.828	Intermediate Similarity	NPD3749	Approved
0.8278	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1607	Approved
0.8258	Intermediate Similarity	NPD1934	Approved
0.8255	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD6599	Discontinued
0.8239	Intermediate Similarity	NPD6959	Discontinued
0.8231	Intermediate Similarity	NPD1551	Phase 2
0.8217	Intermediate Similarity	NPD3882	Suspended
0.8205	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2800	Approved
0.8188	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1243	Approved
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8182	Intermediate Similarity	NPD3226	Approved
0.8148	Intermediate Similarity	NPD7473	Discontinued
0.8141	Intermediate Similarity	NPD6801	Discontinued
0.8108	Intermediate Similarity	NPD2935	Discontinued
0.8101	Intermediate Similarity	NPD7768	Phase 2
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD3268	Approved
0.7987	Intermediate Similarity	NPD6099	Approved
0.7987	Intermediate Similarity	NPD6100	Approved
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5710	Approved
0.7963	Intermediate Similarity	NPD5711	Approved
0.7943	Intermediate Similarity	NPD9717	Approved
0.7939	Intermediate Similarity	NPD7054	Approved
0.7935	Intermediate Similarity	NPD5403	Approved
0.7935	Intermediate Similarity	NPD920	Approved
0.7925	Intermediate Similarity	NPD5402	Approved
0.7919	Intermediate Similarity	NPD2799	Discontinued
0.7908	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6651	Approved
0.7902	Intermediate Similarity	NPD1203	Approved
0.7892	Intermediate Similarity	NPD7472	Approved
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7866	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6166	Phase 2
0.7866	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1465	Phase 2
0.7857	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6797	Phase 2
0.7838	Intermediate Similarity	NPD230	Phase 1
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7806	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD5401	Approved
0.78	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7778	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7755	Intermediate Similarity	NPD411	Approved
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.774	Intermediate Similarity	NPD6832	Phase 2
0.7738	Intermediate Similarity	NPD5953	Discontinued
0.7725	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD447	Suspended
0.7697	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD1608	Approved
0.7655	Intermediate Similarity	NPD2797	Approved
0.7655	Intermediate Similarity	NPD3266	Approved
0.7655	Intermediate Similarity	NPD3267	Approved
0.7635	Intermediate Similarity	NPD2313	Discontinued
0.7628	Intermediate Similarity	NPD7390	Discontinued
0.7622	Intermediate Similarity	NPD5494	Approved
0.7619	Intermediate Similarity	NPD7286	Phase 2
0.76	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2654	Approved
0.7593	Intermediate Similarity	NPD4288	Approved
0.7589	Intermediate Similarity	NPD9545	Approved
0.7588	Intermediate Similarity	NPD6559	Discontinued
0.7586	Intermediate Similarity	NPD3225	Approved
0.7576	Intermediate Similarity	NPD1247	Approved
0.7571	Intermediate Similarity	NPD9493	Approved
0.7566	Intermediate Similarity	NPD7033	Discontinued
0.7566	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD943	Approved
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD2309	Approved
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD17	Approved
0.7483	Intermediate Similarity	NPD2798	Approved
0.747	Intermediate Similarity	NPD7199	Phase 2
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4308	Phase 3
0.7425	Intermediate Similarity	NPD7229	Phase 3
0.7403	Intermediate Similarity	NPD5408	Approved
0.7403	Intermediate Similarity	NPD5404	Approved
0.7403	Intermediate Similarity	NPD5405	Approved
0.7403	Intermediate Similarity	NPD5406	Approved
0.74	Intermediate Similarity	NPD3764	Approved
0.7397	Intermediate Similarity	NPD4749	Approved
0.7391	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4908	Phase 1
0.7381	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7361	Intermediate Similarity	NPD1778	Approved
0.7361	Intermediate Similarity	NPD4626	Approved
0.7355	Intermediate Similarity	NPD1471	Phase 3
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.7337	Intermediate Similarity	NPD2403	Approved
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4287	Approved
0.7285	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1610	Phase 2
0.726	Intermediate Similarity	NPD1201	Approved
0.7256	Intermediate Similarity	NPD37	Approved
0.7255	Intermediate Similarity	NPD1933	Approved
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.7246	Intermediate Similarity	NPD6234	Discontinued
0.723	Intermediate Similarity	NPD1283	Approved
0.7229	Intermediate Similarity	NPD4966	Approved
0.7229	Intermediate Similarity	NPD4965	Approved
0.7229	Intermediate Similarity	NPD4967	Phase 2
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7215	Intermediate Similarity	NPD7003	Approved
0.7211	Intermediate Similarity	NPD9269	Phase 2
0.7205	Intermediate Similarity	NPD6273	Approved
0.7203	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8313	Approved
0.72	Intermediate Similarity	NPD8312	Approved
0.7192	Intermediate Similarity	NPD3496	Discontinued
0.719	Intermediate Similarity	NPD4307	Phase 2
0.7186	Intermediate Similarity	NPD6971	Discontinued
0.7184	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1470	Approved
0.7179	Intermediate Similarity	NPD4477	Approved
0.7179	Intermediate Similarity	NPD4476	Approved
0.7172	Intermediate Similarity	NPD9268	Approved
0.7172	Intermediate Similarity	NPD5691	Approved
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7151	Intermediate Similarity	NPD7177	Discontinued
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7127	Intermediate Similarity	NPD4363	Phase 3
0.7127	Intermediate Similarity	NPD4360	Phase 2
0.7118	Intermediate Similarity	NPD6808	Phase 2
0.7117	Intermediate Similarity	NPD1653	Approved
0.7113	Intermediate Similarity	NPD1241	Discontinued
0.7095	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1481	Phase 2
0.7095	Intermediate Similarity	NPD3972	Approved
0.7091	Intermediate Similarity	NPD5890	Approved
0.7091	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5889	Approved
0.7088	Intermediate Similarity	NPD4361	Phase 2
0.7088	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8434	Phase 2
0.7073	Intermediate Similarity	NPD7458	Discontinued
0.7067	Intermediate Similarity	NPD1164	Approved
0.7066	Intermediate Similarity	NPD5353	Approved
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6585	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