NPASS Compound

Structure

CID137296 OpenBabel06191715492D 23 24 0 0 0 0 0 0 0 0999 V2000 -5.8690 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6010 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4670 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4670 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3331 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 22 1 0 0 0 0 4 6 1 0 0 0 0 4 9 2 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 23 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.11
Volume:	319.761
LogP:	4.027
LogD:	2.764
LogS:	-3.424
# Rotatable Bonds:	5
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	3.49
Fsp3:	0.235
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:	-5.014
MDCK Permeability:	1.2661042092076968e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	98.3375473022461%
Volume Distribution (VD):	0.276
Pgp-substrate:	5.171384811401367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.565
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.746
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	7.337
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.729
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.692
Skin Sensitization:	0.774
Carcinogencity:	0.828
Eye Corrosion:	0.003
Eye Irritation:	0.228
Respiratory Toxicity:	0.416

Download Data

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

Natural Product: NPC137296

Natural Product ID:	NPC137296
*Common Name:**	4-Hydroxy-6-Methoxy-Gamma-7-Dimethyl-3-Oxo-Pthalansorbic Acid
IUPAC Name:	(2E,4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhexa-2,4-dienoic acid
Synonyms:
Standard InCHIKey:	CDBFUCVJNKRICB-PGWPIGLESA-N
Standard InCHI:	InChI=1S/C17H18O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4-5,7,20H,6,8H2,1-3H3,(H,18,19)/b7-5+,9-4+
SMILES:	COc1c(C/C=C(/C=C/C(=O)O)C)c(O)c2c(c1C)COC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256762
PubChem CID:	44448288
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004191] Isocoumarans [CHEMONTID:0003409] Isobenzofuranones [CHEMONTID:0001873] Phthalides

*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
NPO29389	Haplophyllum tuberculatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)82500-5]
NPO33349	penicillium rugulosum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO29464	Kyllinga brevifolia	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29464	Kyllinga brevifolia	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29216	Toddaliopsis bremekampii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19761	Talaromyces rugulosus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29389	Haplophyllum tuberculatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29216	Toddaliopsis bremekampii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29464	Kyllinga brevifolia	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29410	Cedrus libanotica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29500	Athanasia calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	Activity	=	0.11	ug ml-1	PMID[506582]

☑ 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 NPC137296 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	327
0.1-0.2	1489
0.2-0.3	3518
0.3-0.4	7726
0.4-0.5	10790
0.5-0.6	4161
0.6-0.7	6257
0.7-0.8	6591
0.8-0.85	1570
0.85-0.9	238
0.9-0.95	26
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC75694
0.9718	High Similarity	NPC8817
0.9648	High Similarity	NPC470357
0.9257	High Similarity	NPC271681
0.9252	High Similarity	NPC119929
0.9247	High Similarity	NPC470359
0.9161	High Similarity	NPC90411
0.911	High Similarity	NPC163846
0.911	High Similarity	NPC225173
0.9091	High Similarity	NPC165172
0.906	High Similarity	NPC200773
0.906	High Similarity	NPC240768
0.9048	High Similarity	NPC125801
0.9034	High Similarity	NPC51106
0.9034	High Similarity	NPC472006
0.9028	High Similarity	NPC67650
0.9028	High Similarity	NPC1704
0.9021	High Similarity	NPC275356
0.902	High Similarity	NPC470358
0.9	High Similarity	NPC273483
0.8993	High Similarity	NPC179178
0.8986	High Similarity	NPC37139
0.8986	High Similarity	NPC172329
0.8986	High Similarity	NPC2569
0.898	High Similarity	NPC472033
0.898	High Similarity	NPC107625
0.8973	High Similarity	NPC151607
0.8973	High Similarity	NPC42540
0.8966	High Similarity	NPC474385
0.894	High Similarity	NPC477669
0.8926	High Similarity	NPC233267
0.8926	High Similarity	NPC291049
0.8919	High Similarity	NPC472036
0.8919	High Similarity	NPC166583
0.8919	High Similarity	NPC53362
0.8912	High Similarity	NPC472034
0.8904	High Similarity	NPC159721
0.8897	High Similarity	NPC475730
0.8889	High Similarity	NPC246647
0.8889	High Similarity	NPC164110
0.8889	High Similarity	NPC96342
0.8889	High Similarity	NPC212967
0.8889	High Similarity	NPC263483
0.8881	High Similarity	NPC135837
0.8874	High Similarity	NPC175978
0.8867	High Similarity	NPC469670
0.8867	High Similarity	NPC158866
0.8867	High Similarity	NPC469619
0.8859	High Similarity	NPC105415
0.8844	High Similarity	NPC470932
0.8844	High Similarity	NPC210425
0.8844	High Similarity	NPC86373
0.8844	High Similarity	NPC184702
0.8844	High Similarity	NPC277426
0.8844	High Similarity	NPC280404
0.8839	High Similarity	NPC117985
0.8836	High Similarity	NPC250755
0.8824	High Similarity	NPC146211
0.8824	High Similarity	NPC477674
0.8824	High Similarity	NPC180924
0.8816	High Similarity	NPC472799
0.8811	High Similarity	NPC472599
0.8811	High Similarity	NPC158481
0.8808	High Similarity	NPC133856
0.8808	High Similarity	NPC70016
0.8808	High Similarity	NPC477672
0.8808	High Similarity	NPC215921
0.8808	High Similarity	NPC477673
0.88	High Similarity	NPC198927
0.8786	High Similarity	NPC296158
0.8776	High Similarity	NPC472344
0.8776	High Similarity	NPC469542
0.8776	High Similarity	NPC471731
0.8774	High Similarity	NPC313368
0.8774	High Similarity	NPC143050
0.8767	High Similarity	NPC37530
0.8758	High Similarity	NPC149618
0.8758	High Similarity	NPC148938
0.8758	High Similarity	NPC79998
0.8758	High Similarity	NPC16286
0.8758	High Similarity	NPC89625
0.8758	High Similarity	NPC99381
0.875	High Similarity	NPC194579
0.875	High Similarity	NPC40356
0.875	High Similarity	NPC217447
0.875	High Similarity	NPC154683
0.875	High Similarity	NPC70380
0.8742	High Similarity	NPC150928
0.8742	High Similarity	NPC147735
0.8742	High Similarity	NPC255641
0.8742	High Similarity	NPC470568
0.8742	High Similarity	NPC290954
0.8741	High Similarity	NPC180905
0.8741	High Similarity	NPC182496
0.8733	High Similarity	NPC215711
0.8733	High Similarity	NPC73411
0.8725	High Similarity	NPC260946
0.8707	High Similarity	NPC49108
0.8707	High Similarity	NPC469579
0.8707	High Similarity	NPC471733
0.8707	High Similarity	NPC297985
0.8701	High Similarity	NPC197751
0.8701	High Similarity	NPC150227
0.8701	High Similarity	NPC472050
0.8699	High Similarity	NPC187690
0.8699	High Similarity	NPC99441
0.8699	High Similarity	NPC472601
0.8699	High Similarity	NPC472600
0.8693	High Similarity	NPC235333
0.869	High Similarity	NPC191835
0.869	High Similarity	NPC478200
0.869	High Similarity	NPC212693
0.869	High Similarity	NPC33144
0.869	High Similarity	NPC94248
0.8684	High Similarity	NPC470569
0.8681	High Similarity	NPC156967
0.8667	High Similarity	NPC210320
0.8667	High Similarity	NPC289042
0.8667	High Similarity	NPC312929
0.8667	High Similarity	NPC126767
0.8667	High Similarity	NPC190648
0.8667	High Similarity	NPC118027
0.8667	High Similarity	NPC245584
0.8667	High Similarity	NPC56433
0.8658	High Similarity	NPC134621
0.8658	High Similarity	NPC473692
0.8658	High Similarity	NPC83272
0.8654	High Similarity	NPC470810
0.8649	High Similarity	NPC294432
0.8649	High Similarity	NPC112829
0.8649	High Similarity	NPC84266
0.8649	High Similarity	NPC470556
0.8645	High Similarity	NPC190020
0.8645	High Similarity	NPC84935
0.8645	High Similarity	NPC77679
0.8639	High Similarity	NPC472604
0.8639	High Similarity	NPC313123
0.8639	High Similarity	NPC478217
0.8639	High Similarity	NPC158634
0.8639	High Similarity	NPC472035
0.8639	High Similarity	NPC478201
0.8639	High Similarity	NPC472605
0.8639	High Similarity	NPC472603
0.8636	High Similarity	NPC477687
0.8636	High Similarity	NPC199926
0.8636	High Similarity	NPC477671
0.8636	High Similarity	NPC297531
0.8636	High Similarity	NPC213936
0.8627	High Similarity	NPC207624
0.8621	High Similarity	NPC71256
0.8621	High Similarity	NPC245058
0.8618	High Similarity	NPC31132
0.8618	High Similarity	NPC470107
0.8618	High Similarity	NPC294646
0.8618	High Similarity	NPC96501
0.8618	High Similarity	NPC202595
0.8618	High Similarity	NPC295036
0.8609	High Similarity	NPC153417
0.8608	High Similarity	NPC100849
0.8601	High Similarity	NPC153783
0.86	High Similarity	NPC237208
0.8591	High Similarity	NPC478203
0.8591	High Similarity	NPC471305
0.8591	High Similarity	NPC96216
0.8591	High Similarity	NPC126882
0.8591	High Similarity	NPC307895
0.8591	High Similarity	NPC66404
0.8591	High Similarity	NPC470909
0.8591	High Similarity	NPC470553
0.8591	High Similarity	NPC33653
0.8591	High Similarity	NPC210966
0.8591	High Similarity	NPC95123
0.8591	High Similarity	NPC475201
0.8591	High Similarity	NPC184738
0.8591	High Similarity	NPC474939
0.8591	High Similarity	NPC471451
0.859	High Similarity	NPC470339
0.859	High Similarity	NPC324736
0.8581	High Similarity	NPC182255
0.8581	High Similarity	NPC96692
0.8581	High Similarity	NPC477675
0.8581	High Similarity	NPC94076
0.8581	High Similarity	NPC74397
0.8571	High Similarity	NPC210942
0.8571	High Similarity	NPC477691
0.8571	High Similarity	NPC135522
0.8571	High Similarity	NPC472366
0.8571	High Similarity	NPC169990
0.8571	High Similarity	NPC477573
0.8571	High Similarity	NPC137009
0.8571	High Similarity	NPC17219
0.8571	High Similarity	NPC477571
0.8571	High Similarity	NPC477572
0.8571	High Similarity	NPC158472
0.8571	High Similarity	NPC208806
0.8562	High Similarity	NPC149526
0.8562	High Similarity	NPC170169
0.8562	High Similarity	NPC290671
0.8562	High Similarity	NPC474417
0.8562	High Similarity	NPC478148

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 NPC137296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	996
0.2-0.3	1823
0.3-0.4	2546
0.4-0.5	1906
0.5-0.6	1073
0.6-0.7	339
0.7-0.8	162
0.8-0.85	11
0.85-0.9	4
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9857	High Similarity	NPD2534	Approved
0.9857	High Similarity	NPD2533	Approved
0.9857	High Similarity	NPD2532	Approved
0.8903	High Similarity	NPD5710	Approved
0.8903	High Similarity	NPD5711	Approved
0.863	High Similarity	NPD970	Clinical (unspecified phase)
0.8571	High Similarity	NPD7819	Suspended
0.8544	High Similarity	NPD6232	Discontinued
0.8446	Intermediate Similarity	NPD2800	Approved
0.8385	Intermediate Similarity	NPD7473	Discontinued
0.8243	Intermediate Similarity	NPD2935	Discontinued
0.817	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1607	Approved
0.8137	Intermediate Similarity	NPD6959	Discontinued
0.8101	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD7411	Suspended
0.8077	Intermediate Similarity	NPD3226	Approved
0.8067	Intermediate Similarity	NPD2346	Discontinued
0.8065	Intermediate Similarity	NPD920	Approved
0.8063	Intermediate Similarity	NPD7075	Discontinued
0.8063	Intermediate Similarity	NPD3749	Approved
0.8061	Intermediate Similarity	NPD5844	Phase 1
0.8054	Intermediate Similarity	NPD1510	Phase 2
0.8027	Intermediate Similarity	NPD1240	Approved
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8014	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7987	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6651	Approved
0.7917	Intermediate Similarity	NPD6559	Discontinued
0.7908	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD1549	Phase 2
0.7879	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6799	Approved
0.7853	Intermediate Similarity	NPD5494	Approved
0.7852	Intermediate Similarity	NPD230	Phase 1
0.7843	Intermediate Similarity	NPD1243	Approved
0.7829	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6801	Discontinued
0.7812	Intermediate Similarity	NPD1934	Approved
0.7806	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2801	Approved
0.7763	Intermediate Similarity	NPD5405	Approved
0.7763	Intermediate Similarity	NPD5408	Approved
0.7763	Intermediate Similarity	NPD5404	Approved
0.7763	Intermediate Similarity	NPD5406	Approved
0.7763	Intermediate Similarity	NPD2796	Approved
0.7727	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3817	Phase 2
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2799	Discontinued
0.7683	Intermediate Similarity	NPD919	Approved
0.7677	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD7229	Phase 3
0.7651	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5953	Discontinued
0.7643	Intermediate Similarity	NPD7390	Discontinued
0.7643	Intermediate Similarity	NPD1511	Approved
0.7633	Intermediate Similarity	NPD7286	Phase 2
0.7622	Intermediate Similarity	NPD4626	Approved
0.7622	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD37	Approved
0.7582	Intermediate Similarity	NPD3748	Approved
0.7576	Intermediate Similarity	NPD6234	Discontinued
0.7561	Intermediate Similarity	NPD4965	Approved
0.7561	Intermediate Similarity	NPD4967	Phase 2
0.7561	Intermediate Similarity	NPD4966	Approved
0.7552	Intermediate Similarity	NPD5691	Approved
0.7547	Intermediate Similarity	NPD1512	Approved
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7533	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD2313	Discontinued
0.7533	Intermediate Similarity	NPD411	Approved
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.7485	Intermediate Similarity	NPD1247	Approved
0.7484	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD9545	Approved
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD9717	Approved
0.7456	Intermediate Similarity	NPD6166	Phase 2
0.7456	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7003	Approved
0.7427	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6100	Approved
0.7419	Intermediate Similarity	NPD6099	Approved
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7391	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5124	Phase 1
0.7384	Intermediate Similarity	NPD7074	Phase 3
0.7375	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6005	Phase 3
0.7372	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6004	Phase 3
0.7372	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6002	Phase 3
0.7372	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1283	Approved
0.7356	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD9493	Approved
0.7326	Intermediate Similarity	NPD7054	Approved
0.732	Intermediate Similarity	NPD943	Approved
0.732	Intermediate Similarity	NPD2979	Phase 3
0.7315	Intermediate Similarity	NPD1203	Approved
0.7301	Intermediate Similarity	NPD7458	Discontinued
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7296	Intermediate Similarity	NPD2309	Approved
0.7294	Intermediate Similarity	NPD3926	Phase 2
0.7288	Intermediate Similarity	NPD8150	Discontinued
0.7287	Intermediate Similarity	NPD8151	Discontinued
0.7285	Intermediate Similarity	NPD6832	Phase 2
0.7284	Intermediate Similarity	NPD5403	Approved
0.7283	Intermediate Similarity	NPD7472	Approved
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7278	Intermediate Similarity	NPD2654	Approved
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD7177	Discontinued
0.7241	Intermediate Similarity	NPD6797	Phase 2
0.7241	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4625	Phase 3
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6779	Approved
0.7228	Intermediate Similarity	NPD6780	Approved
0.7228	Intermediate Similarity	NPD6781	Approved
0.7228	Intermediate Similarity	NPD6776	Approved
0.7228	Intermediate Similarity	NPD6778	Approved
0.7228	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD6777	Approved
0.7222	Intermediate Similarity	NPD6273	Approved
0.7207	Intermediate Similarity	NPD4287	Approved
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1470	Approved
0.72	Intermediate Similarity	NPD7251	Discontinued
0.7193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8434	Phase 2
0.7162	Intermediate Similarity	NPD1281	Approved
0.7162	Intermediate Similarity	NPD422	Phase 1
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5401	Approved
0.7159	Intermediate Similarity	NPD7808	Phase 3
0.7152	Intermediate Similarity	NPD1019	Discontinued
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD1778	Approved
0.7143	Intermediate Similarity	NPD8366	Approved
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7126	Intermediate Similarity	NPD5761	Phase 2
0.7126	Intermediate Similarity	NPD5760	Phase 2
0.7114	Intermediate Similarity	NPD9269	Phase 2
0.7114	Intermediate Similarity	NPD1608	Approved
0.7112	Intermediate Similarity	NPD7696	Phase 3
0.7112	Intermediate Similarity	NPD7698	Approved
0.7112	Intermediate Similarity	NPD7697	Approved
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7093	Intermediate Similarity	NPD5242	Approved
0.7089	Intermediate Similarity	NPD2438	Suspended
0.7086	Intermediate Similarity	NPD1729	Discontinued
0.7086	Intermediate Similarity	NPD1164	Approved
0.7083	Intermediate Similarity	NPD4288	Approved
0.7078	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD9268	Approved
0.7074	Intermediate Similarity	NPD7871	Phase 2
0.7074	Intermediate Similarity	NPD7870	Phase 2
0.7068	Intermediate Similarity	NPD7874	Approved
0.7068	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6535	Approved
0.7049	Intermediate Similarity	NPD6534	Approved
0.7047	Intermediate Similarity	NPD1201	Approved
0.7043	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2798	Approved
0.7031	Intermediate Similarity	NPD7783	Phase 2
0.7031	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6696	Suspended
0.7013	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8491	Approved
0.7	Intermediate Similarity	NPD3972	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