NPASS Compound

Structure

NPC9180 OpenBabel07101718232D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.1619 3.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9327 -1.1510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8665 -0.9008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8728 1.9251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6761 -1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6761 1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6163 1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3247 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1619 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8665 0.4663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6826 1.6502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2492 0.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3247 2.9000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4875 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1619 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3247 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4875 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4875 3.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5682 -0.7820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5682 0.7820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1829 -0.2173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9990 0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4875 4.3500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6504 2.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2695 -1.7014 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2695 1.7014 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 2 21 1 0 0 0 0 3 21 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 21 1 0 0 0 0 12 22 1 0 0 0 0 13 1 1 1 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 1 0 0 0 19 27 1 0 0 0 0 20 26 1 6 0 0 0 20 27 1 0 0 0 0 22 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	396.804
LogP:	3.778
LogD:	2.772
LogS:	-3.874
# Rotatable Bonds:	5
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	4.523
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.818
MDCK Permeability:	1.888833321572747e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.42
Plasma Protein Binding (PPB):	91.98509979248047%
Volume Distribution (VD):	1.427
Pgp-substrate:	5.204384803771973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.545
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	1.016
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.496
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.356
Rat Oral Acute Toxicity:	0.503
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.331
Carcinogencity:	0.208
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC9180

Natural Product ID:	NPC9180
*Common Name:**	Membranolide C
IUPAC Name:	(2R)-2-[(1R,3R)-1,3-dimethoxy-5-[(1S)-1,3,3-trimethylcyclohexyl]-1,3-dihydro-2-benzofuran-4-yl]propanoic acid
Synonyms:	Membranolide C
Standard InCHIKey:	GRCQGWSFSFNRFC-JRQYZAASSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-13(18(23)24)16-15(22(4)11-7-10-21(2,3)12-22)9-8-14-17(16)20(26-6)27-19(14)25-5/h8-9,13,19-20H,7,10-12H2,1-6H3,(H,23,24)/t13-,19-,20-,22+/m1/s1
SMILES:	C[C@H](c1c(ccc2c1[C@H](OC)O[C@H]2OC)[C@@]1(C)CCCC(C)(C)C1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466575
PubChem CID:	10429624
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004191] Isocoumarans

*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
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	antarctic	n.a.	PMID[15270575]
NPO40100	Dendrilla antarctica	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32281798]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	4

Activity Type	# Activity
Cell Line	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	>	133000.0	nM	PMID[532739]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	4.0	mm	PMID[532738]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	8.0	mm	PMID[532738]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	0.0	mm	PMID[532738]
NPT2	Others	Unspecified		Ratio IC50	>	166.0	n.a.	PMID[532739]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	800.0	nM	PMID[532739]

☑ 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 NPC9180 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	217
0.1-0.2	1095
0.2-0.3	2102
0.3-0.4	5342
0.4-0.5	10828
0.5-0.6	15727
0.6-0.7	6685
0.7-0.8	675
0.8-0.85	16
0.85-0.9	4
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100402
0.8607	High Similarity	NPC45794
0.8583	High Similarity	NPC470816
0.8387	Intermediate Similarity	NPC254233
0.8361	Intermediate Similarity	NPC221275
0.8284	Intermediate Similarity	NPC473399
0.8284	Intermediate Similarity	NPC473216
0.8281	Intermediate Similarity	NPC307139
0.8231	Intermediate Similarity	NPC253681
0.8156	Intermediate Similarity	NPC208293
0.8154	Intermediate Similarity	NPC470818
0.8092	Intermediate Similarity	NPC5486
0.8085	Intermediate Similarity	NPC469513
0.808	Intermediate Similarity	NPC105141
0.808	Intermediate Similarity	NPC242764
0.803	Intermediate Similarity	NPC51448
0.803	Intermediate Similarity	NPC115797
0.8	Intermediate Similarity	NPC470815
0.7941	Intermediate Similarity	NPC48929
0.7937	Intermediate Similarity	NPC212891
0.7931	Intermediate Similarity	NPC162569
0.7931	Intermediate Similarity	NPC116292
0.7931	Intermediate Similarity	NPC267469
0.7931	Intermediate Similarity	NPC87630
0.7931	Intermediate Similarity	NPC35160
0.7931	Intermediate Similarity	NPC179128
0.7926	Intermediate Similarity	NPC471880
0.7923	Intermediate Similarity	NPC273336
0.7923	Intermediate Similarity	NPC182333
0.7923	Intermediate Similarity	NPC472703
0.7917	Intermediate Similarity	NPC469448
0.791	Intermediate Similarity	NPC82712
0.791	Intermediate Similarity	NPC147561
0.7891	Intermediate Similarity	NPC470814
0.7886	Intermediate Similarity	NPC95126
0.7886	Intermediate Similarity	NPC475002
0.7879	Intermediate Similarity	NPC275576
0.7863	Intermediate Similarity	NPC77691
0.7863	Intermediate Similarity	NPC472704
0.7857	Intermediate Similarity	NPC471862
0.7851	Intermediate Similarity	NPC142326
0.7851	Intermediate Similarity	NPC94751
0.7846	Intermediate Similarity	NPC293831
0.7846	Intermediate Similarity	NPC369
0.7829	Intermediate Similarity	NPC183339
0.7829	Intermediate Similarity	NPC146673
0.7829	Intermediate Similarity	NPC233923
0.7829	Intermediate Similarity	NPC133389
0.7829	Intermediate Similarity	NPC234337
0.782	Intermediate Similarity	NPC169913
0.781	Intermediate Similarity	NPC126516
0.781	Intermediate Similarity	NPC329913
0.7803	Intermediate Similarity	NPC295664
0.7787	Intermediate Similarity	NPC21929
0.7786	Intermediate Similarity	NPC275592
0.7786	Intermediate Similarity	NPC171207
0.7786	Intermediate Similarity	NPC476643
0.7786	Intermediate Similarity	NPC100913
0.7786	Intermediate Similarity	NPC97667
0.7786	Intermediate Similarity	NPC475400
0.7786	Intermediate Similarity	NPC90614
0.7778	Intermediate Similarity	NPC306740
0.7761	Intermediate Similarity	NPC230331
0.776	Intermediate Similarity	NPC469547
0.7755	Intermediate Similarity	NPC133430
0.7755	Intermediate Similarity	NPC472658
0.7755	Intermediate Similarity	NPC469477
0.7755	Intermediate Similarity	NPC472657
0.7754	Intermediate Similarity	NPC477893
0.7754	Intermediate Similarity	NPC212207
0.7754	Intermediate Similarity	NPC471864
0.7752	Intermediate Similarity	NPC202015
0.7744	Intermediate Similarity	NPC470765
0.774	Intermediate Similarity	NPC469415
0.7737	Intermediate Similarity	NPC159811
0.7737	Intermediate Similarity	NPC476644
0.773	Intermediate Similarity	NPC97947
0.773	Intermediate Similarity	NPC87448
0.773	Intermediate Similarity	NPC77493
0.773	Intermediate Similarity	NPC291599
0.773	Intermediate Similarity	NPC472576
0.773	Intermediate Similarity	NPC16912
0.773	Intermediate Similarity	NPC118080
0.773	Intermediate Similarity	NPC41481
0.773	Intermediate Similarity	NPC27377
0.7727	Intermediate Similarity	NPC138798
0.7727	Intermediate Similarity	NPC85511
0.7721	Intermediate Similarity	NPC72915
0.7718	Intermediate Similarity	NPC469417
0.7703	Intermediate Similarity	NPC34066
0.7703	Intermediate Similarity	NPC469456
0.7703	Intermediate Similarity	NPC469422
0.7698	Intermediate Similarity	NPC307651
0.7698	Intermediate Similarity	NPC472374
0.7698	Intermediate Similarity	NPC472551
0.7698	Intermediate Similarity	NPC472372
0.7698	Intermediate Similarity	NPC472545
0.7698	Intermediate Similarity	NPC237366
0.7698	Intermediate Similarity	NPC153053
0.7692	Intermediate Similarity	NPC238861
0.7692	Intermediate Similarity	NPC77000
0.7687	Intermediate Similarity	NPC473220
0.7687	Intermediate Similarity	NPC470753
0.7687	Intermediate Similarity	NPC472706
0.7681	Intermediate Similarity	NPC310662
0.7681	Intermediate Similarity	NPC474608
0.7681	Intermediate Similarity	NPC136608
0.7681	Intermediate Similarity	NPC38420
0.768	Intermediate Similarity	NPC82899
0.768	Intermediate Similarity	NPC270699
0.768	Intermediate Similarity	NPC471188
0.7676	Intermediate Similarity	NPC471856
0.7676	Intermediate Similarity	NPC183540
0.7671	Intermediate Similarity	NPC222102
0.7671	Intermediate Similarity	NPC303429
0.7669	Intermediate Similarity	NPC57607
0.7667	Intermediate Similarity	NPC469399
0.766	Intermediate Similarity	NPC472547
0.766	Intermediate Similarity	NPC79921
0.7647	Intermediate Similarity	NPC131684
0.7643	Intermediate Similarity	NPC243893
0.7643	Intermediate Similarity	NPC262324
0.7643	Intermediate Similarity	NPC39549
0.7634	Intermediate Similarity	NPC50872
0.7627	Intermediate Similarity	NPC226041
0.7626	Intermediate Similarity	NPC195647
0.7626	Intermediate Similarity	NPC66761
0.7626	Intermediate Similarity	NPC472577
0.7626	Intermediate Similarity	NPC291638
0.7626	Intermediate Similarity	NPC477896
0.7626	Intermediate Similarity	NPC17877
0.7622	Intermediate Similarity	NPC163087
0.7622	Intermediate Similarity	NPC91703
0.7615	Intermediate Similarity	NPC204784
0.7615	Intermediate Similarity	NPC238582
0.7603	Intermediate Similarity	NPC191899
0.7603	Intermediate Similarity	NPC246229
0.76	Intermediate Similarity	NPC305912
0.76	Intermediate Similarity	NPC1082
0.7594	Intermediate Similarity	NPC328107
0.7594	Intermediate Similarity	NPC51079
0.7594	Intermediate Similarity	NPC228739
0.7591	Intermediate Similarity	NPC475478
0.7584	Intermediate Similarity	NPC469398
0.7583	Intermediate Similarity	NPC133809
0.7583	Intermediate Similarity	NPC136810
0.7583	Intermediate Similarity	NPC225079
0.7583	Intermediate Similarity	NPC128248
0.7578	Intermediate Similarity	NPC9274
0.7576	Intermediate Similarity	NPC167323
0.7576	Intermediate Similarity	NPC269923
0.7571	Intermediate Similarity	NPC309056
0.7569	Intermediate Similarity	NPC472570
0.7569	Intermediate Similarity	NPC95810
0.7569	Intermediate Similarity	NPC475759
0.7569	Intermediate Similarity	NPC476974
0.7569	Intermediate Similarity	NPC125106
0.7569	Intermediate Similarity	NPC57628
0.7569	Intermediate Similarity	NPC472569
0.7569	Intermediate Similarity	NPC163719
0.7569	Intermediate Similarity	NPC472573
0.7569	Intermediate Similarity	NPC475122
0.7569	Intermediate Similarity	NPC95265
0.7569	Intermediate Similarity	NPC241951
0.7569	Intermediate Similarity	NPC188865
0.7569	Intermediate Similarity	NPC25768
0.7569	Intermediate Similarity	NPC11685
0.7569	Intermediate Similarity	NPC470152
0.7569	Intermediate Similarity	NPC70716
0.7557	Intermediate Similarity	NPC473243
0.7554	Intermediate Similarity	NPC203486
0.7551	Intermediate Similarity	NPC475417
0.7551	Intermediate Similarity	NPC475561
0.754	Intermediate Similarity	NPC66208
0.754	Intermediate Similarity	NPC321852
0.7537	Intermediate Similarity	NPC246166
0.7536	Intermediate Similarity	NPC472394
0.7536	Intermediate Similarity	NPC469499
0.7536	Intermediate Similarity	NPC475493
0.7536	Intermediate Similarity	NPC238370
0.7533	Intermediate Similarity	NPC257847
0.752	Intermediate Similarity	NPC214067
0.752	Intermediate Similarity	NPC196246
0.752	Intermediate Similarity	NPC93084
0.752	Intermediate Similarity	NPC251854
0.7519	Intermediate Similarity	NPC108286
0.7519	Intermediate Similarity	NPC223351
0.7518	Intermediate Similarity	NPC283375
0.7518	Intermediate Similarity	NPC183122
0.7518	Intermediate Similarity	NPC27712
0.7518	Intermediate Similarity	NPC471832
0.7517	Intermediate Similarity	NPC29704
0.7517	Intermediate Similarity	NPC200471
0.7517	Intermediate Similarity	NPC96903
0.7517	Intermediate Similarity	NPC473088
0.7517	Intermediate Similarity	NPC469349
0.7517	Intermediate Similarity	NPC470159
0.7517	Intermediate Similarity	NPC472568
0.7517	Intermediate Similarity	NPC472575
0.7517	Intermediate Similarity	NPC476973

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 NPC9180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	778
0.2-0.3	1264
0.3-0.4	2745
0.4-0.5	2400
0.5-0.6	1365
0.6-0.7	379
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5126	Approved
0.7829	Intermediate Similarity	NPD5125	Phase 3
0.7692	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD5951	Approved
0.7518	Intermediate Similarity	NPD7008	Discontinued
0.75	Intermediate Similarity	NPD2629	Approved
0.746	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4198	Discontinued
0.744	Intermediate Similarity	NPD2182	Approved
0.744	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7799	Discontinued
0.7293	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1088	Approved
0.7279	Intermediate Similarity	NPD7236	Approved
0.7279	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD7741	Discontinued
0.725	Intermediate Similarity	NPD1989	Approved
0.7234	Intermediate Similarity	NPD2979	Phase 3
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7167	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6663	Approved
0.7153	Intermediate Similarity	NPD7305	Phase 1
0.7152	Intermediate Similarity	NPD7239	Suspended
0.7122	Intermediate Similarity	NPD5736	Approved
0.712	Intermediate Similarity	NPD164	Approved
0.7119	Intermediate Similarity	NPD1089	Approved
0.7119	Intermediate Similarity	NPD1090	Approved
0.7119	Intermediate Similarity	NPD1086	Approved
0.7113	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2066	Phase 3
0.7059	Intermediate Similarity	NPD5618	Discontinued
0.7059	Intermediate Similarity	NPD1281	Approved
0.7059	Intermediate Similarity	NPD6287	Discontinued
0.705	Intermediate Similarity	NPD6085	Phase 2
0.705	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD800	Approved
0.7027	Intermediate Similarity	NPD4628	Phase 3
0.7025	Intermediate Similarity	NPD1693	Approved
0.7023	Intermediate Similarity	NPD6010	Discontinued
0.7007	Intermediate Similarity	NPD1608	Approved
0.6993	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3764	Approved
0.6968	Remote Similarity	NPD37	Approved
0.6954	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6858	Approved
0.6947	Remote Similarity	NPD7094	Approved
0.6943	Remote Similarity	NPD4965	Approved
0.6943	Remote Similarity	NPD4967	Phase 2
0.6943	Remote Similarity	NPD4966	Approved
0.6939	Remote Similarity	NPD6004	Phase 3
0.6939	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6002	Phase 3
0.6939	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6005	Phase 3
0.6935	Remote Similarity	NPD1238	Approved
0.6923	Remote Similarity	NPD8032	Phase 2
0.6917	Remote Similarity	NPD1239	Approved
0.6913	Remote Similarity	NPD7003	Approved
0.6912	Remote Similarity	NPD1778	Approved
0.6911	Remote Similarity	NPD1566	Phase 3
0.6911	Remote Similarity	NPD1565	Approved
0.6911	Remote Similarity	NPD1564	Approved
0.6905	Remote Similarity	NPD1930	Approved
0.6905	Remote Similarity	NPD1929	Approved
0.6905	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6685	Approved
0.6871	Remote Similarity	NPD2531	Phase 2
0.6871	Remote Similarity	NPD2438	Suspended
0.687	Remote Similarity	NPD969	Suspended
0.6864	Remote Similarity	NPD1087	Approved
0.6855	Remote Similarity	NPD6234	Discontinued
0.6853	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5909	Discontinued
0.6842	Remote Similarity	NPD2532	Approved
0.6842	Remote Similarity	NPD2534	Approved
0.6842	Remote Similarity	NPD2533	Approved
0.6829	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2346	Discontinued
0.6824	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8455	Phase 2
0.6815	Remote Similarity	NPD6065	Approved
0.6812	Remote Similarity	NPD4807	Approved
0.6812	Remote Similarity	NPD4806	Approved
0.6806	Remote Similarity	NPD7714	Approved
0.6806	Remote Similarity	NPD7961	Discontinued
0.6806	Remote Similarity	NPD7715	Approved
0.68	Remote Similarity	NPD8166	Discontinued
0.6797	Remote Similarity	NPD6273	Approved
0.6797	Remote Similarity	NPD5048	Discontinued
0.6794	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2932	Approved
0.6788	Remote Similarity	NPD5306	Approved
0.6788	Remote Similarity	NPD3019	Approved
0.6788	Remote Similarity	NPD5305	Approved
0.6788	Remote Similarity	NPD17	Approved
0.6772	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6647	Phase 2
0.6768	Remote Similarity	NPD7228	Approved
0.6765	Remote Similarity	NPD4479	Discontinued
0.6763	Remote Similarity	NPD6637	Approved
0.6759	Remote Similarity	NPD4140	Approved
0.6757	Remote Similarity	NPD4476	Approved
0.6757	Remote Similarity	NPD4477	Approved
0.6748	Remote Similarity	NPD6049	Phase 2
0.6748	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2067	Discontinued
0.6716	Remote Similarity	NPD4766	Approved
0.6716	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1651	Approved
0.6715	Remote Similarity	NPD5585	Approved
0.6694	Remote Similarity	NPD3673	Approved
0.6694	Remote Similarity	NPD3672	Approved
0.6689	Remote Similarity	NPD4110	Phase 3
0.6689	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8407	Phase 2
0.6667	Remote Similarity	NPD7199	Phase 2
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD1563	Approved
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6100	Approved
0.6644	Remote Similarity	NPD6099	Approved
0.6643	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD9545	Approved
0.6641	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5765	Approved
0.6627	Remote Similarity	NPD8312	Approved
0.6627	Remote Similarity	NPD8313	Approved
0.6626	Remote Similarity	NPD7229	Phase 3
0.6625	Remote Similarity	NPD7057	Phase 3
0.6625	Remote Similarity	NPD7058	Phase 2
0.6624	Remote Similarity	NPD7028	Phase 2
0.6623	Remote Similarity	NPD6674	Discontinued
0.6623	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3026	Approved
0.6619	Remote Similarity	NPD4135	Approved
0.6619	Remote Similarity	NPD4106	Approved
0.6619	Remote Similarity	NPD4136	Approved
0.6619	Remote Similarity	NPD3023	Approved
0.6617	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5347	Phase 2
0.6612	Remote Similarity	NPD5346	Phase 2
0.6607	Remote Similarity	NPD7240	Approved
0.6607	Remote Similarity	NPD8368	Discontinued
0.6604	Remote Similarity	NPD7819	Suspended
0.66	Remote Similarity	NPD5763	Approved
0.66	Remote Similarity	NPD5762	Approved
0.6594	Remote Similarity	NPD3025	Approved
0.6594	Remote Similarity	NPD3024	Approved
0.6594	Remote Similarity	NPD5691	Approved
0.6587	Remote Similarity	NPD9495	Approved
0.6585	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2799	Discontinued
0.6561	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6696	Suspended
0.6547	Remote Similarity	NPD4199	Phase 3
0.6547	Remote Similarity	NPD4626	Approved
0.6544	Remote Similarity	NPD3317	Approved
0.6531	Remote Similarity	NPD4060	Phase 1
0.6528	Remote Similarity	NPD5204	Approved
0.6525	Remote Similarity	NPD3972	Approved
0.6525	Remote Similarity	NPD9491	Approved
0.6522	Remote Similarity	NPD1894	Discontinued
0.6519	Remote Similarity	NPD2650	Approved
0.6519	Remote Similarity	NPD2652	Approved
0.651	Remote Similarity	NPD7097	Phase 1
0.6507	Remote Similarity	NPD3268	Approved
0.6507	Remote Similarity	NPD2313	Discontinued
0.6503	Remote Similarity	NPD2797	Approved
0.6493	Remote Similarity	NPD6912	Phase 3
0.6483	Remote Similarity	NPD2613	Approved
0.6479	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD4359	Approved
0.6475	Remote Similarity	NPD5981	Approved
0.6475	Remote Similarity	NPD4105	Approved
0.6475	Remote Similarity	NPD4102	Approved
0.6467	Remote Similarity	NPD7033	Discontinued
0.6466	Remote Similarity	NPD5239	Approved
0.6466	Remote Similarity	NPD5236	Approved
0.6466	Remote Similarity	NPD5235	Approved
0.6466	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4234	Approved
0.6466	Remote Similarity	NPD4233	Approved
0.6466	Remote Similarity	NPD5240	Approved
0.6466	Remote Similarity	NPD5237	Approved
0.6463	Remote Similarity	NPD8127	Discontinued
0.6458	Remote Similarity	NPD2798	Approved
0.6457	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD1611	Approved
0.6454	Remote Similarity	NPD3705	Approved
0.6453	Remote Similarity	NPD8055	Clinical (unspecified phase)

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