NPASS Compound

Structure

NPC472610 OpenBabel07101718242D 24 25 0 0 1 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 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 -0.8660 -2.5000 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 -0.8660 -1.5000 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 -1.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 3.4641 -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 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 -5.1962 -3.0000 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 2.5981 1.5000 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 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 10 1 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 7 23 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 6 1 1 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.14
Volume:	333.825
LogP:	3.791
LogD:	2.681
LogS:	-3.334
# Rotatable Bonds:	8
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.607
Synthetic Accessibility Score:	3.238
Fsp3:	0.529
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:	-4.796
MDCK Permeability:	5.424357368610799e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.14
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.396
30% Bioavailability (F30%):	0.808

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.534
Plasma Protein Binding (PPB):	91.20755767822266%
Volume Distribution (VD):	0.718
Pgp-substrate:	11.02550220489502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.86
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.642
CYP2C19-substrate:	0.102
CYP2C9-inhibitor:	0.586
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.814
CYP2D6-substrate:	0.243
CYP3A4-inhibitor:	0.593
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	13.665
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.481
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.598
Carcinogencity:	0.04
Eye Corrosion:	0.025
Eye Irritation:	0.858
Respiratory Toxicity:	0.439

Download Data

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

Natural Product: NPC472610

Natural Product ID:	NPC472610
*Common Name:**	WWCKZGQUKPCTIF-LLVKDONJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WWCKZGQUKPCTIF-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C17H22O7/c1-10-12-8-11(6-4-3-5-7-23-17(21)22-2)24-16(20)15(12)14(19)9-13(10)18/h9,11,18-19H,3-8H2,1-2H3/t11-/m1/s1
SMILES:	COC(=O)OCCCCC[C@H]1OC(=O)c2c(C1)c(C)c(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581075
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*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
NPO32981	cadophora sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[26035018]

☑ 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
MIC	9

Activity Type	# Activity
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	100.0	ug.mL-1	PMID[459669]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[459669]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[459669]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	100.0	ug.mL-1	PMID[459669]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[459669]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[459669]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	100.0	ug.mL-1	PMID[459669]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[459669]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[459669]

☑ 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 NPC472610 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	325
0.1-0.2	1455
0.2-0.3	3324
0.3-0.4	7866
0.4-0.5	11057
0.5-0.6	3909
0.6-0.7	6688
0.7-0.8	6729
0.8-0.85	1082
0.85-0.9	196
0.9-0.95	58
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9779	High Similarity	NPC472601
0.9779	High Similarity	NPC472600
0.9708	High Similarity	NPC472604
0.9708	High Similarity	NPC472603
0.9708	High Similarity	NPC472605
0.9568	High Similarity	NPC159721
0.9562	High Similarity	NPC88269
0.95	High Similarity	NPC42540
0.95	High Similarity	NPC151607
0.9489	High Similarity	NPC472602
0.9437	High Similarity	NPC471734
0.9429	High Similarity	NPC471731
0.9424	High Similarity	NPC53649
0.9416	High Similarity	NPC70380
0.9366	High Similarity	NPC471735
0.9366	High Similarity	NPC473023
0.9357	High Similarity	NPC471733
0.9348	High Similarity	NPC191835
0.9348	High Similarity	NPC94248
0.9348	High Similarity	NPC212693
0.9343	High Similarity	NPC235115
0.9275	High Similarity	NPC194579
0.9209	High Similarity	NPC478200
0.9209	High Similarity	NPC221104
0.9209	High Similarity	NPC33144
0.9203	High Similarity	NPC472599
0.9203	High Similarity	NPC291454
0.9203	High Similarity	NPC50455
0.9155	High Similarity	NPC478202
0.9155	High Similarity	NPC469542
0.9149	High Similarity	NPC313123
0.9149	High Similarity	NPC478217
0.9149	High Similarity	NPC67650
0.9149	High Similarity	NPC158634
0.9149	High Similarity	NPC1704
0.9143	High Similarity	NPC275356
0.9143	High Similarity	NPC105456
0.9143	High Similarity	NPC32360
0.9143	High Similarity	NPC139634
0.9137	High Similarity	NPC71256
0.9124	High Similarity	NPC153783
0.9085	High Similarity	NPC82913
0.9085	High Similarity	NPC469579
0.9078	High Similarity	NPC158472
0.9078	High Similarity	NPC155205
0.9065	High Similarity	NPC156967
0.9065	High Similarity	NPC158481
0.9058	High Similarity	NPC475645
0.9051	High Similarity	NPC476389
0.9028	High Similarity	NPC473692
0.9021	High Similarity	NPC472006
0.9021	High Similarity	NPC51106
0.9014	High Similarity	NPC472035
0.9014	High Similarity	NPC37530
0.9014	High Similarity	NPC470842
0.9014	High Similarity	NPC478201
0.9007	High Similarity	NPC268052
0.9	High Similarity	NPC178467
0.9	High Similarity	NPC149372
0.9	High Similarity	NPC65837
0.9	High Similarity	NPC245058
0.9	High Similarity	NPC474849
0.9	High Similarity	NPC474771
0.8993	High Similarity	NPC142027
0.8993	High Similarity	NPC27407
0.8978	High Similarity	NPC219892
0.8978	High Similarity	NPC189823
0.8951	High Similarity	NPC474385
0.8951	High Similarity	NPC322112
0.8944	High Similarity	NPC64664
0.8944	High Similarity	NPC99441
0.8936	High Similarity	NPC475974
0.8921	High Similarity	NPC175943
0.8897	High Similarity	NPC83272
0.8881	High Similarity	NPC244923
0.8881	High Similarity	NPC475730
0.8865	High Similarity	NPC135837
0.8865	High Similarity	NPC261292
0.8865	High Similarity	NPC301915
0.8844	High Similarity	NPC221352
0.8841	High Similarity	NPC214702
0.8841	High Similarity	NPC470831
0.8836	High Similarity	NPC225173
0.8836	High Similarity	NPC107625
0.8836	High Similarity	NPC163846
0.8836	High Similarity	NPC260946
0.8828	High Similarity	NPC126882
0.8828	High Similarity	NPC478203
0.8828	High Similarity	NPC210425
0.8828	High Similarity	NPC86373
0.8828	High Similarity	NPC277426
0.8828	High Similarity	NPC280404
0.8828	High Similarity	NPC210966
0.8819	High Similarity	NPC250755
0.8811	High Similarity	NPC165172
0.8811	High Similarity	NPC168471
0.8803	High Similarity	NPC472403
0.8803	High Similarity	NPC177307
0.8803	High Similarity	NPC9121
0.88	High Similarity	NPC472799
0.8792	High Similarity	NPC70016
0.8792	High Similarity	NPC215921
0.8784	High Similarity	NPC291049
0.8784	High Similarity	NPC233267
0.8784	High Similarity	NPC237440
0.8784	High Similarity	NPC270160
0.8776	High Similarity	NPC53362
0.8776	High Similarity	NPC166583
0.8776	High Similarity	NPC125801
0.8768	High Similarity	NPC296158
0.8767	High Similarity	NPC472034
0.8767	High Similarity	NPC257558
0.8767	High Similarity	NPC134621
0.875	High Similarity	NPC257309
0.8741	High Similarity	NPC52358
0.8741	High Similarity	NPC474655
0.8741	High Similarity	NPC247409
0.8741	High Similarity	NPC92655
0.8733	High Similarity	NPC273483
0.8725	High Similarity	NPC150928
0.8725	High Similarity	NPC179178
0.8723	High Similarity	NPC290803
0.8723	High Similarity	NPC180905
0.8723	High Similarity	NPC182496
0.8716	High Similarity	NPC471641
0.8716	High Similarity	NPC37139
0.8716	High Similarity	NPC105415
0.8716	High Similarity	NPC240622
0.8716	High Similarity	NPC240253
0.8716	High Similarity	NPC471642
0.8714	High Similarity	NPC180261
0.8714	High Similarity	NPC37299
0.8707	High Similarity	NPC472033
0.8707	High Similarity	NPC237208
0.8707	High Similarity	NPC470570
0.8699	High Similarity	NPC95123
0.8699	High Similarity	NPC66404
0.8675	High Similarity	NPC470102
0.8667	High Similarity	NPC232645
0.8667	High Similarity	NPC133856
0.8667	High Similarity	NPC72958
0.8662	High Similarity	NPC118919
0.8658	High Similarity	NPC247219
0.8658	High Similarity	NPC77325
0.8658	High Similarity	NPC4423
0.8658	High Similarity	NPC476684
0.8652	High Similarity	NPC474394
0.8649	High Similarity	NPC210320
0.8649	High Similarity	NPC476463
0.8649	High Similarity	NPC472036
0.8649	High Similarity	NPC8817
0.8639	High Similarity	NPC29577
0.8639	High Similarity	NPC34482
0.8639	High Similarity	NPC75694
0.8639	High Similarity	NPC312789
0.8636	High Similarity	NPC470358
0.8633	High Similarity	NPC247477
0.8633	High Similarity	NPC17840
0.863	High Similarity	NPC471639
0.863	High Similarity	NPC354984
0.863	High Similarity	NPC471643
0.8621	High Similarity	NPC90411
0.8621	High Similarity	NPC149533
0.8618	High Similarity	NPC149618
0.8618	High Similarity	NPC82592
0.8618	High Similarity	NPC89625
0.8618	High Similarity	NPC16082
0.8609	High Similarity	NPC167903
0.8609	High Similarity	NPC87708
0.8609	High Similarity	NPC115249
0.8609	High Similarity	NPC217447
0.86	High Similarity	NPC56204
0.86	High Similarity	NPC469670
0.86	High Similarity	NPC119929
0.86	High Similarity	NPC472891
0.86	High Similarity	NPC325983
0.86	High Similarity	NPC158866
0.86	High Similarity	NPC469619
0.8592	High Similarity	NPC278375
0.8592	High Similarity	NPC470844
0.8591	High Similarity	NPC73411
0.8591	High Similarity	NPC215711
0.8582	High Similarity	NPC470988
0.8581	High Similarity	NPC24136
0.8581	High Similarity	NPC187282
0.8581	High Similarity	NPC290133
0.8581	High Similarity	NPC267509
0.8581	High Similarity	NPC470357
0.8581	High Similarity	NPC69868
0.8571	High Similarity	NPC48762
0.8562	High Similarity	NPC472050
0.8562	High Similarity	NPC105648
0.8562	High Similarity	NPC150227
0.8553	High Similarity	NPC477571
0.8553	High Similarity	NPC471695
0.8553	High Similarity	NPC137301
0.8553	High Similarity	NPC192189
0.8553	High Similarity	NPC298778
0.8553	High Similarity	NPC477572
0.8553	High Similarity	NPC281477

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 NPC472610 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	934
0.2-0.3	1817
0.3-0.4	2634
0.4-0.5	1875
0.5-0.6	1120
0.6-0.7	346
0.7-0.8	138
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD970	Clinical (unspecified phase)
0.8639	High Similarity	NPD2534	Approved
0.8639	High Similarity	NPD2533	Approved
0.8639	High Similarity	NPD2532	Approved
0.8553	High Similarity	NPD7819	Suspended
0.8228	Intermediate Similarity	NPD6959	Discontinued
0.8194	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7075	Discontinued
0.8077	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7411	Suspended
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8063	Intermediate Similarity	NPD5711	Approved
0.8063	Intermediate Similarity	NPD5710	Approved
0.8041	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4380	Phase 2
0.7987	Intermediate Similarity	NPD1549	Phase 2
0.7973	Intermediate Similarity	NPD2935	Discontinued
0.7945	Intermediate Similarity	NPD230	Phase 1
0.7925	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7473	Discontinued
0.7905	Intermediate Similarity	NPD1510	Phase 2
0.7898	Intermediate Similarity	NPD1934	Approved
0.7898	Intermediate Similarity	NPD6801	Discontinued
0.7877	Intermediate Similarity	NPD1240	Approved
0.7862	Intermediate Similarity	NPD7768	Phase 2
0.7853	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7390	Discontinued
0.7818	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5844	Phase 1
0.7815	Intermediate Similarity	NPD2800	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD7074	Phase 3
0.777	Intermediate Similarity	NPD6651	Approved
0.777	Intermediate Similarity	NPD1607	Approved
0.7763	Intermediate Similarity	NPD3750	Approved
0.775	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5405	Approved
0.7733	Intermediate Similarity	NPD5406	Approved
0.7733	Intermediate Similarity	NPD5408	Approved
0.7733	Intermediate Similarity	NPD5404	Approved
0.7733	Intermediate Similarity	NPD2796	Approved
0.7727	Intermediate Similarity	NPD6799	Approved
0.7711	Intermediate Similarity	NPD7054	Approved
0.7702	Intermediate Similarity	NPD3749	Approved
0.7698	Intermediate Similarity	NPD9545	Approved
0.7688	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7472	Approved
0.7658	Intermediate Similarity	NPD6599	Discontinued
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7647	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6797	Phase 2
0.7619	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1551	Phase 2
0.7582	Intermediate Similarity	NPD1243	Approved
0.7582	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD920	Approved
0.7578	Intermediate Similarity	NPD3817	Phase 2
0.7574	Intermediate Similarity	NPD7251	Discontinued
0.7562	Intermediate Similarity	NPD37	Approved
0.7554	Intermediate Similarity	NPD9493	Approved
0.7546	Intermediate Similarity	NPD6234	Discontinued
0.7531	Intermediate Similarity	NPD4965	Approved
0.7531	Intermediate Similarity	NPD4966	Approved
0.7531	Intermediate Similarity	NPD3882	Suspended
0.7531	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6166	Phase 2
0.753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7517	Intermediate Similarity	NPD943	Approved
0.7516	Intermediate Similarity	NPD2801	Approved
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD5494	Approved
0.7484	Intermediate Similarity	NPD3226	Approved
0.7451	Intermediate Similarity	NPD2346	Discontinued
0.7436	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2799	Discontinued
0.7434	Intermediate Similarity	NPD3748	Approved
0.7434	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4628	Phase 3
0.7412	Intermediate Similarity	NPD5953	Discontinued
0.7405	Intermediate Similarity	NPD1512	Approved
0.7397	Intermediate Similarity	NPD1164	Approved
0.7396	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD6099	Approved
0.7386	Intermediate Similarity	NPD6100	Approved
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7375	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1201	Approved
0.7358	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8150	Discontinued
0.7351	Intermediate Similarity	NPD8151	Discontinued
0.7349	Intermediate Similarity	NPD7199	Phase 2
0.7342	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7228	Approved
0.7333	Intermediate Similarity	NPD919	Approved
0.7303	Intermediate Similarity	NPD6535	Approved
0.7303	Intermediate Similarity	NPD6534	Approved
0.7279	Intermediate Similarity	NPD1470	Approved
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5402	Approved
0.725	Intermediate Similarity	NPD5403	Approved
0.7237	Intermediate Similarity	NPD5124	Phase 1
0.7237	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8319	Approved
0.7228	Intermediate Similarity	NPD8320	Phase 1
0.7222	Intermediate Similarity	NPD4626	Approved
0.7209	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.7198	Intermediate Similarity	NPD6778	Approved
0.7198	Intermediate Similarity	NPD6779	Approved
0.7198	Intermediate Similarity	NPD6776	Approved
0.7198	Intermediate Similarity	NPD6777	Approved
0.7198	Intermediate Similarity	NPD6782	Approved
0.7198	Intermediate Similarity	NPD6780	Approved
0.7198	Intermediate Similarity	NPD6781	Approved
0.7192	Intermediate Similarity	NPD9269	Phase 2
0.7192	Intermediate Similarity	NPD9717	Approved
0.7182	Intermediate Similarity	NPD7700	Phase 2
0.7182	Intermediate Similarity	NPD7699	Phase 2
0.7162	Intermediate Similarity	NPD1203	Approved
0.7153	Intermediate Similarity	NPD5691	Approved
0.7153	Intermediate Similarity	NPD9268	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7133	Intermediate Similarity	NPD6832	Phase 2
0.7126	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5401	Approved
0.7123	Intermediate Similarity	NPD422	Phase 1
0.7114	Intermediate Similarity	NPD2798	Approved
0.7102	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7095	Intermediate Similarity	NPD1283	Approved
0.709	Intermediate Similarity	NPD7783	Phase 2
0.709	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7081	Intermediate Similarity	NPD7696	Phase 3
0.7081	Intermediate Similarity	NPD7698	Approved
0.7081	Intermediate Similarity	NPD7697	Approved
0.7075	Intermediate Similarity	NPD1608	Approved
0.7073	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4060	Phase 1
0.7056	Intermediate Similarity	NPD6213	Phase 3
0.7056	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6212	Phase 3
0.7044	Intermediate Similarity	NPD6190	Approved
0.7043	Intermediate Similarity	NPD7871	Phase 2
0.7043	Intermediate Similarity	NPD7870	Phase 2
0.7039	Intermediate Similarity	NPD2313	Discontinued
0.7039	Intermediate Similarity	NPD411	Approved
0.7037	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7874	Approved
0.7034	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2654	Approved
0.702	Intermediate Similarity	NPD4908	Phase 1
0.7013	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1933	Approved
0.7013	Intermediate Similarity	NPD447	Suspended
0.7006	Intermediate Similarity	NPD7266	Discontinued
0.7006	Intermediate Similarity	NPD2344	Approved
0.6994	Remote Similarity	NPD1653	Approved
0.6993	Remote Similarity	NPD6663	Approved
0.6988	Remote Similarity	NPD8455	Phase 2
0.6978	Remote Similarity	NPD74	Approved
0.6978	Remote Similarity	NPD9266	Approved
0.6975	Remote Similarity	NPD6273	Approved
0.6971	Remote Similarity	NPD7240	Approved
0.6954	Remote Similarity	NPD5736	Approved
0.6948	Remote Similarity	NPD2979	Phase 3
0.6946	Remote Similarity	NPD5353	Approved
0.6946	Remote Similarity	NPD4288	Approved
0.6943	Remote Similarity	NPD4476	Approved
0.6943	Remote Similarity	NPD2438	Suspended
0.6943	Remote Similarity	NPD4477	Approved
0.6941	Remote Similarity	NPD1247	Approved
0.6936	Remote Similarity	NPD7177	Discontinued
0.6935	Remote Similarity	NPD6823	Phase 2
0.6933	Remote Similarity	NPD2797	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data