NPASS Compound

Structure

NPC240622 OpenBabel07101718202D 26 27 0 0 1 0 0 0 0 0999 V2000 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 -0.8660 -1.5000 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 -1.7321 -1.0000 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 -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 -0.0000 -4.0000 0.0000 C 0 0 1 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 -0.8660 -4.5000 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 0.0000 3.0000 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 2.5981 4.5000 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 3 25 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 2 1 6 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	374.286
LogP:	3.357
LogD:	2.846
LogS:	-3.234
# Rotatable Bonds:	10
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	3.12
Fsp3:	0.5
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:	-4.763
MDCK Permeability:	4.011508644907735e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.785
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.138
30% Bioavailability (F30%):	0.633

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	92.82464599609375%
Volume Distribution (VD):	0.627
Pgp-substrate:	13.676617622375488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.634
CYP2C19-inhibitor:	0.944
CYP2C19-substrate:	0.152
CYP2C9-inhibitor:	0.915
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.494
CYP2D6-substrate:	0.384
CYP3A4-inhibitor:	0.729
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	8.504
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.17
AMES Toxicity:	0.292
Rat Oral Acute Toxicity:	0.207
Maximum Recommended Daily Dose:	0.82
Skin Sensitization:	0.62
Carcinogencity:	0.066
Eye Corrosion:	0.005
Eye Irritation:	0.218
Respiratory Toxicity:	0.109

Download Data

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

Natural Product: NPC240622

Natural Product ID:	NPC240622
*Common Name:**	Ethyl 2-[7-Hydroxy-2-[(6S)-6-Hydroxyheptyl]-4-Oxochromen-5-Yl]Acetate
IUPAC Name:	ethyl 2-[7-hydroxy-2-[(6S)-6-hydroxyheptyl]-4-oxochromen-5-yl]acetate
Synonyms:
Standard InCHIKey:	NRXGHYGIYHFZNK-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-3-25-19(24)10-14-9-15(22)11-18-20(14)17(23)12-16(26-18)8-6-4-5-7-13(2)21/h9,11-13,21-22H,3-8,10H2,1-2H3/t13-/m0/s1
SMILES:	CCOC(=O)Cc1cc(cc2c1c(=O)cc(CCCCC[C@H](C)O)o2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3086817
PubChem CID:	72946785
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
IC50	4
MIC	4

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	500.0	ug.mL-1	PMID[525562]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	500.0	ug.mL-1	PMID[525562]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	500.0	ug.mL-1	PMID[525562]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	500.0	ug.mL-1	PMID[525562]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IC50	=	484.0	ug.mL-1	PMID[525562]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IC50	=	440.0	ug.mL-1	PMID[525562]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	500.0	ug.mL-1	PMID[525562]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	>	500.0	ug.mL-1	PMID[525562]

☑ 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 NPC240622 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	346
0.1-0.2	1526
0.2-0.3	3632
0.3-0.4	8384
0.4-0.5	10360
0.5-0.6	3679
0.6-0.7	5622
0.7-0.8	5210
0.8-0.85	2881
0.85-0.9	919
0.9-0.95	123
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471641
1.0	High Similarity	NPC240253
1.0	High Similarity	NPC471642
0.9787	High Similarity	NPC312789
0.9574	High Similarity	NPC471640
0.9574	High Similarity	NPC471644
0.9514	High Similarity	NPC472036
0.951	High Similarity	NPC472034
0.9444	High Similarity	NPC472033
0.9437	High Similarity	NPC474385
0.9371	High Similarity	NPC472006
0.9371	High Similarity	NPC478202
0.9371	High Similarity	NPC471639
0.9371	High Similarity	NPC51106
0.9371	High Similarity	NPC471643
0.9371	High Similarity	NPC469542
0.9366	High Similarity	NPC158634
0.9366	High Similarity	NPC67650
0.9366	High Similarity	NPC1704
0.9362	High Similarity	NPC268052
0.9362	High Similarity	NPC32360
0.9362	High Similarity	NPC57380
0.932	High Similarity	NPC60413
0.9315	High Similarity	NPC153417
0.9306	High Similarity	NPC210425
0.9306	High Similarity	NPC277426
0.9306	High Similarity	NPC66404
0.9306	High Similarity	NPC95123
0.9306	High Similarity	NPC280404
0.9306	High Similarity	NPC86373
0.9301	High Similarity	NPC469579
0.9252	High Similarity	NPC6923
0.9247	High Similarity	NPC210320
0.9241	High Similarity	NPC134621
0.9231	High Similarity	NPC478201
0.9231	High Similarity	NPC478217
0.9231	High Similarity	NPC313123
0.9231	High Similarity	NPC472035
0.9231	High Similarity	NPC475730
0.9225	High Similarity	NPC92655
0.922	High Similarity	NPC135837
0.9184	High Similarity	NPC215711
0.9184	High Similarity	NPC73411
0.9178	High Similarity	NPC237208
0.9178	High Similarity	NPC107625
0.9167	High Similarity	NPC105648
0.9155	High Similarity	NPC191835
0.9155	High Similarity	NPC212693
0.9155	High Similarity	NPC94248
0.9155	High Similarity	NPC478200
0.9155	High Similarity	NPC475974
0.9155	High Similarity	NPC33144
0.9149	High Similarity	NPC242712
0.9122	High Similarity	NPC476684
0.9116	High Similarity	NPC14098
0.911	High Similarity	NPC473692
0.911	High Similarity	NPC29577
0.911	High Similarity	NPC257558
0.9097	High Similarity	NPC307990
0.9097	High Similarity	NPC16455
0.9097	High Similarity	NPC220106
0.9085	High Similarity	NPC65837
0.9085	High Similarity	NPC178467
0.9085	High Similarity	NPC474771
0.9085	High Similarity	NPC474849
0.9085	High Similarity	NPC70380
0.9085	High Similarity	NPC149372
0.9078	High Similarity	NPC182496
0.9078	High Similarity	NPC180905
0.9067	High Similarity	NPC273483
0.906	High Similarity	NPC295036
0.906	High Similarity	NPC158866
0.9054	High Similarity	NPC37139
0.9041	High Similarity	NPC126882
0.9041	High Similarity	NPC478203
0.9041	High Similarity	NPC210966
0.9034	High Similarity	NPC96692
0.9034	High Similarity	NPC250755
0.9028	High Similarity	NPC139554
0.9028	High Similarity	NPC158472
0.9021	High Similarity	NPC177307
0.9021	High Similarity	NPC472403
0.9021	High Similarity	NPC472602
0.9021	High Similarity	NPC9121
0.9014	High Similarity	NPC235115
0.9007	High Similarity	NPC175943
0.9007	High Similarity	NPC223457
0.9	High Similarity	NPC133856
0.9	High Similarity	NPC70016
0.9	High Similarity	NPC215921
0.8993	High Similarity	NPC473978
0.8993	High Similarity	NPC77325
0.8993	High Similarity	NPC291049
0.8993	High Similarity	NPC270160
0.8993	High Similarity	NPC233267
0.8993	High Similarity	NPC237440
0.8993	High Similarity	NPC4423
0.8986	High Similarity	NPC259632
0.8986	High Similarity	NPC12305
0.8973	High Similarity	NPC310340
0.8973	High Similarity	NPC294432
0.8966	High Similarity	NPC472604
0.8966	High Similarity	NPC472603
0.8966	High Similarity	NPC244923
0.8966	High Similarity	NPC53649
0.8966	High Similarity	NPC90411
0.8966	High Similarity	NPC472605
0.8958	High Similarity	NPC474655
0.8958	High Similarity	NPC247409
0.8958	High Similarity	NPC139634
0.8958	High Similarity	NPC105456
0.8954	High Similarity	NPC246466
0.8951	High Similarity	NPC470397
0.8947	High Similarity	NPC89625
0.8947	High Similarity	NPC149618
0.894	High Similarity	NPC474843
0.8936	High Similarity	NPC203817
0.8936	High Similarity	NPC10971
0.8936	High Similarity	NPC153783
0.8933	High Similarity	NPC469670
0.8933	High Similarity	NPC469619
0.8926	High Similarity	NPC105415
0.8919	High Similarity	NPC267509
0.8912	High Similarity	NPC470909
0.8912	High Similarity	NPC474939
0.8912	High Similarity	NPC33653
0.8912	High Similarity	NPC96216
0.8912	High Similarity	NPC184738
0.8897	High Similarity	NPC472601
0.8897	High Similarity	NPC472600
0.8882	High Similarity	NPC472799
0.8874	High Similarity	NPC72958
0.8874	High Similarity	NPC240768
0.8874	High Similarity	NPC200773
0.8874	High Similarity	NPC232645
0.8867	High Similarity	NPC65589
0.8867	High Similarity	NPC97029
0.8867	High Similarity	NPC100985
0.8867	High Similarity	NPC288036
0.8867	High Similarity	NPC158338
0.8867	High Similarity	NPC97028
0.8865	High Similarity	NPC475589
0.8865	High Similarity	NPC31872
0.8865	High Similarity	NPC473584
0.8851	High Similarity	NPC288910
0.8851	High Similarity	NPC470554
0.8851	High Similarity	NPC118059
0.8851	High Similarity	NPC224714
0.8851	High Similarity	NPC133060
0.8851	High Similarity	NPC32470
0.8844	High Similarity	NPC471731
0.8844	High Similarity	NPC73028
0.8844	High Similarity	NPC470556
0.8844	High Similarity	NPC112829
0.8844	High Similarity	NPC159721
0.8836	High Similarity	NPC275734
0.8831	High Similarity	NPC263483
0.8828	High Similarity	NPC131130
0.8824	High Similarity	NPC82592
0.8824	High Similarity	NPC99381
0.8824	High Similarity	NPC16082
0.8819	High Similarity	NPC470398
0.8819	High Similarity	NPC121243
0.8819	High Similarity	NPC240147
0.8819	High Similarity	NPC71256
0.8819	High Similarity	NPC174999
0.8816	High Similarity	NPC256141
0.8816	High Similarity	NPC478224
0.8816	High Similarity	NPC87708
0.8816	High Similarity	NPC271681
0.8816	High Similarity	NPC167903
0.8811	High Similarity	NPC236974
0.8811	High Similarity	NPC144027
0.8808	High Similarity	NPC309979
0.8808	High Similarity	NPC307780
0.8808	High Similarity	NPC37348
0.8808	High Similarity	NPC472891
0.8808	High Similarity	NPC475460
0.8808	High Similarity	NPC150928
0.8808	High Similarity	NPC470107
0.8808	High Similarity	NPC474735
0.8808	High Similarity	NPC180351
0.8803	High Similarity	NPC25937
0.88	High Similarity	NPC7025
0.88	High Similarity	NPC2569
0.88	High Similarity	NPC256672
0.88	High Similarity	NPC172329
0.88	High Similarity	NPC27221
0.88	High Similarity	NPC35150
0.88	High Similarity	NPC106328
0.8794	High Similarity	NPC219892
0.8794	High Similarity	NPC5515
0.8794	High Similarity	NPC270369
0.8794	High Similarity	NPC189823
0.8792	High Similarity	NPC187282
0.8792	High Similarity	NPC470910
0.8792	High Similarity	NPC290133
0.8792	High Similarity	NPC163846
0.8792	High Similarity	NPC225173
0.8792	High Similarity	NPC473023

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 NPC240622 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	955
0.2-0.3	1754
0.3-0.4	2505
0.4-0.5	1906
0.5-0.6	1126
0.6-0.7	403
0.7-0.8	136
0.8-0.85	51
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9225	High Similarity	NPD970	Clinical (unspecified phase)
0.8758	High Similarity	NPD7819	Suspended
0.86	High Similarity	NPD2532	Approved
0.86	High Similarity	NPD2534	Approved
0.86	High Similarity	NPD2533	Approved
0.8506	High Similarity	NPD7411	Suspended
0.8503	High Similarity	NPD1552	Clinical (unspecified phase)
0.8503	High Similarity	NPD1550	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD3750	Approved
0.8446	Intermediate Similarity	NPD1549	Phase 2
0.8435	Intermediate Similarity	NPD2796	Approved
0.8411	Intermediate Similarity	NPD6799	Approved
0.8397	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1510	Phase 2
0.8354	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD1934	Approved
0.8313	Intermediate Similarity	NPD6959	Discontinued
0.8289	Intermediate Similarity	NPD1511	Approved
0.828	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD2801	Approved
0.8272	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1240	Approved
0.8207	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4380	Phase 2
0.8205	Intermediate Similarity	NPD6599	Discontinued
0.8188	Intermediate Similarity	NPD1551	Phase 2
0.8182	Intermediate Similarity	NPD1512	Approved
0.8176	Intermediate Similarity	NPD3882	Suspended
0.8146	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD5403	Approved
0.8125	Intermediate Similarity	NPD3749	Approved
0.8121	Intermediate Similarity	NPD3748	Approved
0.8121	Intermediate Similarity	NPD7054	Approved
0.8117	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD5402	Approved
0.8108	Intermediate Similarity	NPD1607	Approved
0.8072	Intermediate Similarity	NPD7472	Approved
0.8063	Intermediate Similarity	NPD7768	Phase 2
0.8063	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD3818	Discontinued
0.8049	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6166	Phase 2
0.8037	Intermediate Similarity	NPD6232	Discontinued
0.8036	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2800	Approved
0.8026	Intermediate Similarity	NPD1243	Approved
0.8025	Intermediate Similarity	NPD3226	Approved
0.8024	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD7473	Discontinued
0.7976	Intermediate Similarity	NPD7251	Discontinued
0.7974	Intermediate Similarity	NPD4628	Phase 3
0.7964	Intermediate Similarity	NPD7074	Phase 3
0.7947	Intermediate Similarity	NPD2935	Discontinued
0.7929	Intermediate Similarity	NPD7808	Phase 3
0.7927	Intermediate Similarity	NPD5710	Approved
0.7927	Intermediate Similarity	NPD5711	Approved
0.7904	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD920	Approved
0.7871	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD3268	Approved
0.7832	Intermediate Similarity	NPD422	Phase 1
0.7829	Intermediate Similarity	NPD6099	Approved
0.7829	Intermediate Similarity	NPD6100	Approved
0.78	Intermediate Similarity	NPD230	Phase 1
0.7778	Intermediate Similarity	NPD9717	Approved
0.7771	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD2799	Discontinued
0.7763	Intermediate Similarity	NPD7033	Discontinued
0.7748	Intermediate Similarity	NPD6651	Approved
0.7744	Intermediate Similarity	NPD919	Approved
0.774	Intermediate Similarity	NPD1203	Approved
0.7716	Intermediate Similarity	NPD1465	Phase 2
0.7706	Intermediate Similarity	NPD5953	Discontinued
0.7706	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6832	Phase 2
0.7697	Intermediate Similarity	NPD5494	Approved
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7658	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD411	Approved
0.7588	Intermediate Similarity	NPD7286	Phase 2
0.7578	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD447	Suspended
0.7566	Intermediate Similarity	NPD5124	Phase 1
0.7566	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD9545	Approved
0.7548	Intermediate Similarity	NPD2344	Approved
0.7545	Intermediate Similarity	NPD7199	Phase 2
0.7545	Intermediate Similarity	NPD1247	Approved
0.7534	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD3266	Approved
0.7484	Intermediate Similarity	NPD7390	Discontinued
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7472	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4288	Approved
0.7452	Intermediate Similarity	NPD2654	Approved
0.7439	Intermediate Similarity	NPD37	Approved
0.7432	Intermediate Similarity	NPD3225	Approved
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7419	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD9493	Approved
0.741	Intermediate Similarity	NPD4966	Approved
0.741	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD4967	Phase 2
0.7396	Intermediate Similarity	NPD7229	Phase 3
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7391	Intermediate Similarity	NPD6273	Approved
0.7386	Intermediate Similarity	NPD943	Approved
0.7371	Intermediate Similarity	NPD8313	Approved
0.7371	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1296	Phase 2
0.7358	Intermediate Similarity	NPD2309	Approved
0.7353	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3926	Phase 2
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1652	Phase 2
0.7333	Intermediate Similarity	NPD1019	Discontinued
0.7333	Intermediate Similarity	NPD2798	Approved
0.7329	Intermediate Similarity	NPD17	Approved
0.7329	Intermediate Similarity	NPD1778	Approved
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.731	Intermediate Similarity	NPD1548	Phase 1
0.7308	Intermediate Similarity	NPD4308	Phase 3
0.7308	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1653	Approved
0.7293	Intermediate Similarity	NPD4363	Phase 3
0.7293	Intermediate Similarity	NPD4360	Phase 2
0.7283	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7261	Intermediate Similarity	NPD5405	Approved
0.7261	Intermediate Similarity	NPD5406	Approved
0.7261	Intermediate Similarity	NPD5404	Approved
0.7261	Intermediate Similarity	NPD5408	Approved
0.7255	Intermediate Similarity	NPD3764	Approved
0.7255	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4749	Approved
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.723	Intermediate Similarity	NPD1610	Phase 2
0.723	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7225	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1471	Phase 3
0.7215	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6004	Phase 3
0.7215	Intermediate Similarity	NPD6002	Phase 3
0.7215	Intermediate Similarity	NPD6005	Phase 3
0.7211	Intermediate Similarity	NPD4626	Approved
0.7209	Intermediate Similarity	NPD2403	Approved
0.7193	Intermediate Similarity	NPD6808	Phase 2
0.719	Intermediate Similarity	NPD4625	Phase 3
0.7169	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4287	Approved
0.7162	Intermediate Similarity	NPD3496	Discontinued
0.7161	Intermediate Similarity	NPD1613	Approved
0.7161	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8151	Discontinued
0.7158	Intermediate Similarity	NPD4361	Phase 2
0.7158	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4476	Approved
0.7152	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD5691	Approved
0.7126	Intermediate Similarity	NPD6844	Discontinued
0.7126	Intermediate Similarity	NPD7228	Approved
0.7126	Intermediate Similarity	NPD7177	Discontinued
0.7124	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1933	Approved
0.7114	Intermediate Similarity	NPD1201	Approved
0.711	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5647	Approved
0.7086	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7081	Intermediate Similarity	NPD7003	Approved
0.7078	Intermediate Similarity	NPD3027	Phase 3
0.7074	Intermediate Similarity	NPD7435	Discontinued
0.7067	Intermediate Similarity	NPD9269	Phase 2

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