NPASS Compound

Structure

CID62867 OpenBabel06191715402D 33 35 0 0 1 0 0 0 0 0999 V2000 -5.1962 -4.0000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 1.5000 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 -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 -4.3301 -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 -6.0622 -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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 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 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -8.6603 -3.0000 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 -2.5981 -1.5000 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 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3923 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 19 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 22 2 0 0 0 0 12 16 1 0 0 0 0 12 23 2 0 0 0 0 13 18 1 0 0 0 0 13 24 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 26 2 0 0 0 0 16 27 1 0 0 0 0 17 28 2 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 24 27 1 0 0 0 0 25 28 1 0 0 0 0 26 32 1 0 0 0 0 27 31 1 6 0 0 0 28 33 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 6 0 0 0 31 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.35
Volume:	520.824
LogP:	7.841
LogD:	5.548
LogS:	-3.952
# Rotatable Bonds:	8
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	4.15
Fsp3:	0.613
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	1.4836856280453503e-05
Pgp-inhibitor:	0.118
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.343
Plasma Protein Binding (PPB):	99.92180633544922%
Volume Distribution (VD):	2.775
Pgp-substrate:	0.6820639371871948%

ADMET: Metabolism

CYP1A2-inhibitor:	0.155
CYP1A2-substrate:	0.243
CYP2C19-inhibitor:	0.579
CYP2C19-substrate:	0.507
CYP2C9-inhibitor:	0.288
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.927
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.724
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	8.694
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.941
Carcinogencity:	0.028
Eye Corrosion:	0.384
Eye Irritation:	0.915
Respiratory Toxicity:	0.753

Download Data

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

Natural Product: NPC62867

Natural Product ID:	NPC62867
*Common Name:**	Coscinoquinol
IUPAC Name:	2-[(2E,7Z)-9-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3,7-dimethylnona-2,7-dienyl]benzene-1,4-diol
Synonyms:	Coscinoquinol
Standard InCHIKey:	FBBXOWQBMFRXRO-MEVHTVKHSA-N
Standard InCHI:	InChI=1S/C31H46O2/c1-22(11-14-25-21-26(32)15-17-28(25)33)9-7-10-23(2)12-16-27-24(3)13-18-29-30(4,5)19-8-20-31(27,29)6/h11-13,15,17,21,27,29,32-33H,7-10,14,16,18-20H2,1-6H3/b22-11+,23-12-/t27-,29-,31+/m0/s1
SMILES:	C/C(=CCc1cc(ccc1O)O)/CCC/C(=CC[C@H]1C(=CC[C@H]2C(C)(C)CCC[C@]12C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818095
PubChem CID:	11744503
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO30318	Coscinoderma	Genus	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21827183]

☑ 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	3
MIC	10
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	10
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	8000.0	nM	PMID[506779]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	200000.0	nM	PMID[506779]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	200000.0	nM	PMID[506779]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	44000.0	nM	PMID[506779]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[506779]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.25	ug.mL-1	PMID[506779]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	25.0	ug.mL-1	PMID[506779]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	25.0	ug.mL-1	PMID[506779]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	6.25	ug.mL-1	PMID[506779]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[506779]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[506779]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[506779]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[506779]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[506779]

☑ 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 NPC62867 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	306
0.1-0.2	1560
0.2-0.3	3108
0.3-0.4	10009
0.4-0.5	9848
0.5-0.6	11897
0.6-0.7	4790
0.7-0.8	960
0.8-0.85	147
0.85-0.9	57
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC177962
0.9904	High Similarity	NPC470770
0.9904	High Similarity	NPC266937
0.9714	High Similarity	NPC77772
0.9519	High Similarity	NPC320439
0.945	High Similarity	NPC141001
0.9423	High Similarity	NPC155072
0.9286	High Similarity	NPC477037
0.9286	High Similarity	NPC318581
0.9286	High Similarity	NPC325544
0.9266	High Similarity	NPC471534
0.9143	High Similarity	NPC47284
0.9083	High Similarity	NPC250323
0.9074	High Similarity	NPC13482
0.9057	High Similarity	NPC53740
0.9027	High Similarity	NPC323074
0.8952	High Similarity	NPC269212
0.8942	High Similarity	NPC48730
0.8942	High Similarity	NPC248396
0.8942	High Similarity	NPC129373
0.8929	High Similarity	NPC471668
0.8899	High Similarity	NPC296683
0.8899	High Similarity	NPC141782
0.8857	High Similarity	NPC252105
0.8857	High Similarity	NPC477685
0.8857	High Similarity	NPC12221
0.885	High Similarity	NPC477136
0.8846	High Similarity	NPC260775
0.8818	High Similarity	NPC260323
0.8818	High Similarity	NPC469912
0.8818	High Similarity	NPC176279
0.8818	High Similarity	NPC54373
0.8785	High Similarity	NPC117115
0.8774	High Similarity	NPC108497
0.8762	High Similarity	NPC130756
0.8762	High Similarity	NPC12931
0.8762	High Similarity	NPC70677
0.8761	High Similarity	NPC308828
0.8761	High Similarity	NPC92
0.8761	High Similarity	NPC469663
0.875	High Similarity	NPC152097
0.875	High Similarity	NPC268160
0.875	High Similarity	NPC195922
0.8739	High Similarity	NPC228425
0.8727	High Similarity	NPC132720
0.8716	High Similarity	NPC11554
0.8704	High Similarity	NPC469913
0.8696	High Similarity	NPC93071
0.8692	High Similarity	NPC272029
0.8692	High Similarity	NPC475580
0.8679	High Similarity	NPC80800
0.8673	High Similarity	NPC192948
0.8673	High Similarity	NPC147179
0.8673	High Similarity	NPC469719
0.8673	High Similarity	NPC35797
0.8667	High Similarity	NPC299762
0.8667	High Similarity	NPC33675
0.8649	High Similarity	NPC322753
0.8649	High Similarity	NPC95716
0.8624	High Similarity	NPC151477
0.8621	High Similarity	NPC260832
0.8621	High Similarity	NPC135467
0.8609	High Similarity	NPC469609
0.8609	High Similarity	NPC206
0.8598	High Similarity	NPC233827
0.8596	High Similarity	NPC38893
0.8596	High Similarity	NPC219112
0.8596	High Similarity	NPC477137
0.8596	High Similarity	NPC308311
0.8585	High Similarity	NPC72729
0.8571	High Similarity	NPC302371
0.8571	High Similarity	NPC475078
0.8571	High Similarity	NPC79241
0.8571	High Similarity	NPC6597
0.8571	High Similarity	NPC248557
0.8571	High Similarity	NPC46940
0.8559	High Similarity	NPC478058
0.8547	High Similarity	NPC32322
0.8547	High Similarity	NPC259703
0.8534	High Similarity	NPC126002
0.8534	High Similarity	NPC469644
0.8532	High Similarity	NPC21594
0.8532	High Similarity	NPC54765
0.8522	High Similarity	NPC16030
0.8522	High Similarity	NPC172219
0.8522	High Similarity	NPC304510
0.8519	High Similarity	NPC475225
0.8509	High Similarity	NPC84999
0.8509	High Similarity	NPC246760
0.8496	Intermediate Similarity	NPC715
0.8476	Intermediate Similarity	NPC259512
0.8476	Intermediate Similarity	NPC312132
0.8468	Intermediate Similarity	NPC58865
0.8462	Intermediate Similarity	NPC152415
0.8448	Intermediate Similarity	NPC154030
0.8448	Intermediate Similarity	NPC471671
0.8443	Intermediate Similarity	NPC47288
0.8443	Intermediate Similarity	NPC176590
0.844	Intermediate Similarity	NPC138942
0.8435	Intermediate Similarity	NPC474387
0.8435	Intermediate Similarity	NPC154511
0.8435	Intermediate Similarity	NPC137496
0.8435	Intermediate Similarity	NPC257540
0.8435	Intermediate Similarity	NPC474358
0.8435	Intermediate Similarity	NPC247858
0.8426	Intermediate Similarity	NPC235762
0.8426	Intermediate Similarity	NPC471228
0.8411	Intermediate Similarity	NPC225506
0.8381	Intermediate Similarity	NPC32714
0.8381	Intermediate Similarity	NPC222146
0.8378	Intermediate Similarity	NPC95344
0.8378	Intermediate Similarity	NPC64586
0.8376	Intermediate Similarity	NPC151197
0.8376	Intermediate Similarity	NPC51341
0.8365	Intermediate Similarity	NPC162314
0.8365	Intermediate Similarity	NPC55903
0.8365	Intermediate Similarity	NPC210497
0.8365	Intermediate Similarity	NPC3358
0.8365	Intermediate Similarity	NPC147284
0.8365	Intermediate Similarity	NPC306884
0.8365	Intermediate Similarity	NPC94139
0.8365	Intermediate Similarity	NPC29373
0.8364	Intermediate Similarity	NPC271274
0.8364	Intermediate Similarity	NPC67250
0.8364	Intermediate Similarity	NPC310456
0.8349	Intermediate Similarity	NPC238696
0.8349	Intermediate Similarity	NPC288411
0.8349	Intermediate Similarity	NPC323810
0.8333	Intermediate Similarity	NPC51015
0.8319	Intermediate Similarity	NPC154696
0.8319	Intermediate Similarity	NPC275627
0.8319	Intermediate Similarity	NPC224527
0.8319	Intermediate Similarity	NPC151537
0.8318	Intermediate Similarity	NPC122005
0.8318	Intermediate Similarity	NPC252821
0.8318	Intermediate Similarity	NPC92730
0.8306	Intermediate Similarity	NPC472793
0.8304	Intermediate Similarity	NPC186385
0.8304	Intermediate Similarity	NPC282855
0.8304	Intermediate Similarity	NPC299568
0.8304	Intermediate Similarity	NPC26013
0.8291	Intermediate Similarity	NPC48342
0.8291	Intermediate Similarity	NPC164649
0.8288	Intermediate Similarity	NPC474352
0.8288	Intermediate Similarity	NPC66834
0.8286	Intermediate Similarity	NPC289769
0.8286	Intermediate Similarity	NPC76938
0.8286	Intermediate Similarity	NPC245187
0.8273	Intermediate Similarity	NPC99557
0.8273	Intermediate Similarity	NPC219286
0.8269	Intermediate Similarity	NPC306074
0.8257	Intermediate Similarity	NPC168829
0.8246	Intermediate Similarity	NPC98372
0.8241	Intermediate Similarity	NPC211885
0.8241	Intermediate Similarity	NPC174911
0.824	Intermediate Similarity	NPC153019
0.824	Intermediate Similarity	NPC473047
0.8235	Intermediate Similarity	NPC328504
0.8235	Intermediate Similarity	NPC241001
0.8235	Intermediate Similarity	NPC129176
0.823	Intermediate Similarity	NPC208229
0.8224	Intermediate Similarity	NPC77492
0.8224	Intermediate Similarity	NPC225464
0.8224	Intermediate Similarity	NPC156313
0.822	Intermediate Similarity	NPC42657
0.822	Intermediate Similarity	NPC471449
0.8214	Intermediate Similarity	NPC68260
0.8214	Intermediate Similarity	NPC279887
0.8214	Intermediate Similarity	NPC306295
0.8211	Intermediate Similarity	NPC471530
0.8205	Intermediate Similarity	NPC320864
0.8205	Intermediate Similarity	NPC299180
0.8182	Intermediate Similarity	NPC471187
0.8174	Intermediate Similarity	NPC23804
0.8173	Intermediate Similarity	NPC192
0.8167	Intermediate Similarity	NPC162935
0.8167	Intermediate Similarity	NPC475839
0.8167	Intermediate Similarity	NPC48623
0.8167	Intermediate Similarity	NPC253627
0.8167	Intermediate Similarity	NPC168707
0.8167	Intermediate Similarity	NPC249340
0.8151	Intermediate Similarity	NPC475245
0.8151	Intermediate Similarity	NPC99734
0.8151	Intermediate Similarity	NPC68339
0.8151	Intermediate Similarity	NPC190501
0.8151	Intermediate Similarity	NPC318552
0.8142	Intermediate Similarity	NPC19808
0.8142	Intermediate Similarity	NPC314187
0.8142	Intermediate Similarity	NPC33728
0.8131	Intermediate Similarity	NPC473388
0.8131	Intermediate Similarity	NPC292730
0.8131	Intermediate Similarity	NPC132271
0.8131	Intermediate Similarity	NPC82664
0.8131	Intermediate Similarity	NPC216520
0.8125	Intermediate Similarity	NPC204901
0.8125	Intermediate Similarity	NPC158253
0.8125	Intermediate Similarity	NPC232523
0.8115	Intermediate Similarity	NPC61685
0.8113	Intermediate Similarity	NPC27323
0.8113	Intermediate Similarity	NPC316301

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 NPC62867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	961
0.2-0.3	1164
0.3-0.4	2877
0.4-0.5	2136
0.5-0.6	1290
0.6-0.7	339
0.7-0.8	75
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9083	High Similarity	NPD7635	Approved
0.8942	High Similarity	NPD289	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD288	Approved
0.8381	Intermediate Similarity	NPD844	Approved
0.8318	Intermediate Similarity	NPD3020	Approved
0.8305	Intermediate Similarity	NPD2932	Approved
0.8304	Intermediate Similarity	NPD4750	Phase 3
0.8291	Intermediate Similarity	NPD3091	Approved
0.8288	Intermediate Similarity	NPD2342	Discontinued
0.819	Intermediate Similarity	NPD845	Approved
0.8151	Intermediate Similarity	NPD4059	Approved
0.8151	Intermediate Similarity	NPD3019	Approved
0.8113	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1809	Phase 2
0.8037	Intermediate Similarity	NPD2859	Approved
0.8037	Intermediate Similarity	NPD2860	Approved
0.8034	Intermediate Similarity	NPD6671	Approved
0.8017	Intermediate Similarity	NPD3092	Approved
0.7982	Intermediate Similarity	NPD3021	Approved
0.7982	Intermediate Similarity	NPD3022	Approved
0.7944	Intermediate Similarity	NPD2934	Approved
0.7944	Intermediate Similarity	NPD2933	Approved
0.7903	Intermediate Similarity	NPD3094	Phase 2
0.7851	Intermediate Similarity	NPD3095	Discontinued
0.7826	Intermediate Similarity	NPD1792	Phase 2
0.7823	Intermediate Similarity	NPD6696	Suspended
0.7797	Intermediate Similarity	NPD497	Approved
0.7778	Intermediate Similarity	NPD5736	Approved
0.7724	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD496	Approved
0.7712	Intermediate Similarity	NPD498	Approved
0.7712	Intermediate Similarity	NPD495	Approved
0.7705	Intermediate Similarity	NPD1751	Approved
0.7698	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7340	Approved
0.7667	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD4093	Discontinued
0.76	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD1445	Approved
0.7565	Intermediate Similarity	NPD1444	Approved
0.7542	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6663	Approved
0.7522	Intermediate Similarity	NPD940	Approved
0.7522	Intermediate Similarity	NPD846	Approved
0.75	Intermediate Similarity	NPD3635	Approved
0.75	Intermediate Similarity	NPD3636	Approved
0.75	Intermediate Similarity	NPD3637	Approved
0.75	Intermediate Similarity	NPD3023	Approved
0.75	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD3026	Approved
0.748	Intermediate Similarity	NPD3024	Approved
0.748	Intermediate Similarity	NPD3025	Approved
0.746	Intermediate Similarity	NPD4749	Approved
0.7442	Intermediate Similarity	NPD2606	Approved
0.7442	Intermediate Similarity	NPD2605	Approved
0.744	Intermediate Similarity	NPD1201	Approved
0.7422	Intermediate Similarity	NPD4624	Approved
0.7422	Intermediate Similarity	NPD2194	Approved
0.7422	Intermediate Similarity	NPD2195	Approved
0.7419	Intermediate Similarity	NPD2286	Discontinued
0.7419	Intermediate Similarity	NPD4589	Approved
0.7417	Intermediate Similarity	NPD2229	Approved
0.7417	Intermediate Similarity	NPD2228	Approved
0.7417	Intermediate Similarity	NPD2234	Approved
0.7417	Intermediate Similarity	NPD1398	Phase 1
0.7417	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7330	Discontinued
0.7398	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4625	Phase 3
0.7385	Intermediate Similarity	NPD5155	Approved
0.7385	Intermediate Similarity	NPD5156	Approved
0.7381	Intermediate Similarity	NPD2233	Approved
0.7381	Intermediate Similarity	NPD2232	Approved
0.7381	Intermediate Similarity	NPD2230	Approved
0.7368	Intermediate Similarity	NPD4097	Suspended
0.7323	Intermediate Similarity	NPD5327	Phase 3
0.7308	Intermediate Similarity	NPD3595	Approved
0.7308	Intermediate Similarity	NPD3594	Approved
0.7281	Intermediate Similarity	NPD1242	Phase 1
0.728	Intermediate Similarity	NPD4626	Approved
0.7264	Intermediate Similarity	NPD111	Approved
0.7259	Intermediate Similarity	NPD7742	Approved
0.7259	Intermediate Similarity	NPD7743	Approved
0.7258	Intermediate Similarity	NPD5303	Approved
0.7258	Intermediate Similarity	NPD5304	Approved
0.7236	Intermediate Similarity	NPD7636	Approved
0.7218	Intermediate Similarity	NPD3620	Phase 2
0.7218	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1791	Approved
0.7213	Intermediate Similarity	NPD1793	Approved
0.7209	Intermediate Similarity	NPD1470	Approved
0.7206	Intermediate Similarity	NPD6100	Approved
0.7206	Intermediate Similarity	NPD6099	Approved
0.7165	Intermediate Similarity	NPD1611	Approved
0.7164	Intermediate Similarity	NPD5735	Approved
0.7155	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD8166	Discontinued
0.7119	Intermediate Similarity	NPD968	Approved
0.7111	Intermediate Similarity	NPD6353	Approved
0.7101	Intermediate Similarity	NPD4256	Phase 2
0.7101	Intermediate Similarity	NPD4257	Approved
0.7097	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4060	Phase 1
0.709	Intermediate Similarity	NPD4140	Approved
0.709	Intermediate Similarity	NPD6346	Approved
0.7087	Intermediate Similarity	NPD3496	Discontinued
0.7077	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4721	Approved
0.7029	Intermediate Similarity	NPD4725	Approved
0.7029	Intermediate Similarity	NPD4726	Approved
0.7021	Intermediate Similarity	NPD3300	Phase 2
0.7016	Intermediate Similarity	NPD709	Approved
0.7009	Intermediate Similarity	NPD9500	Approved
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5283	Phase 1
0.6983	Remote Similarity	NPD3028	Approved
0.695	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5691	Approved
0.6929	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3638	Discontinued
0.6929	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9088	Approved
0.6923	Remote Similarity	NPD1755	Approved
0.6917	Remote Similarity	NPD4908	Phase 1
0.6905	Remote Similarity	NPD7644	Approved
0.6899	Remote Similarity	NPD1610	Phase 2
0.6889	Remote Similarity	NPD8032	Phase 2
0.688	Remote Similarity	NPD6387	Discontinued
0.688	Remote Similarity	NPD7157	Approved
0.6875	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6090	Discontinued
0.687	Remote Similarity	NPD1283	Approved
0.687	Remote Similarity	NPD8651	Approved
0.6866	Remote Similarity	NPD7095	Approved
0.685	Remote Similarity	NPD7741	Discontinued
0.6838	Remote Similarity	NPD2238	Phase 2
0.6835	Remote Similarity	NPD2935	Discontinued
0.6829	Remote Similarity	NPD228	Approved
0.6822	Remote Similarity	NPD1981	Approved
0.6822	Remote Similarity	NPD1983	Approved
0.6822	Remote Similarity	NPD3143	Discontinued
0.6822	Remote Similarity	NPD1980	Approved
0.6818	Remote Similarity	NPD2797	Approved
0.681	Remote Similarity	NPD9273	Approved
0.6806	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5951	Approved
0.68	Remote Similarity	NPD9614	Approved
0.68	Remote Similarity	NPD9618	Approved
0.6797	Remote Similarity	NPD1651	Approved
0.6797	Remote Similarity	NPD5585	Approved
0.6786	Remote Similarity	NPD5763	Approved
0.6786	Remote Similarity	NPD5762	Approved
0.678	Remote Similarity	NPD4817	Approved
0.678	Remote Similarity	NPD4818	Approved
0.6767	Remote Similarity	NPD6584	Phase 3
0.6761	Remote Similarity	NPD7003	Approved
0.6744	Remote Similarity	NPD1778	Approved
0.6744	Remote Similarity	NPD2668	Approved
0.6744	Remote Similarity	NPD2667	Approved
0.6736	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7041	Phase 2
0.6721	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3070	Discontinued
0.6718	Remote Similarity	NPD2235	Phase 2
0.6718	Remote Similarity	NPD2231	Phase 2
0.6714	Remote Similarity	NPD5406	Approved
0.6714	Remote Similarity	NPD5408	Approved
0.6714	Remote Similarity	NPD5405	Approved
0.6714	Remote Similarity	NPD5404	Approved
0.6713	Remote Similarity	NPD8131	Suspended
0.6692	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9608	Approved
0.6667	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4659	Approved
0.6667	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD9610	Approved
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD1669	Approved
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2798	Approved
0.6641	Remote Similarity	NPD9615	Approved
0.6641	Remote Similarity	NPD1281	Approved
0.6641	Remote Similarity	NPD9616	Approved
0.6641	Remote Similarity	NPD9613	Approved
0.664	Remote Similarity	NPD9379	Approved
0.664	Remote Similarity	NPD1138	Approved
0.664	Remote Similarity	NPD9377	Approved
0.6621	Remote Similarity	NPD2421	Approved
0.6621	Remote Similarity	NPD2420	Approved
0.6621	Remote Similarity	NPD7390	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data