NPASS Compound

Structure

NPC132228 OpenBabel07101718182D 26 28 0 0 1 0 0 0 0 0999 V2000 3.5981 -0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -0.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 2.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7321 0.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 17 1 0 0 0 0 11 18 2 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 6 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 22 1 6 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 21 3 1 1 0 0 0 22 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	385.377
LogP:	4.097
LogD:	3.72
LogS:	-4.682
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	4.621
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.827
MDCK Permeability:	2.8712578568956815e-05
Pgp-inhibitor:	0.947
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.752
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	95.59141540527344%
Volume Distribution (VD):	0.977
Pgp-substrate:	3.6599860191345215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.69
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.58
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.623
CYP2C9-substrate:	0.597
CYP2D6-inhibitor:	0.924
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.804
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	2.004
Half-life (T1/2):	0.126

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.772
Drug-inuced Liver Injury (DILI):	0.199
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.84
Skin Sensitization:	0.944
Carcinogencity:	0.849
Eye Corrosion:	0.039
Eye Irritation:	0.052
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC132228

Natural Product ID:	NPC132228
*Common Name:**	Bolinaquinone
IUPAC Name:	3-[[(1R,2R,4aS,8aS)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:	Bolinaquinone
Standard InCHIKey:	PYUXUMSQSVWNDS-NSAJDELNSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-13-7-6-8-16-14(2)21(3,9-10-22(13,16)4)12-15-19(24)17(23)11-18(26-5)20(15)25/h7,11,14,16,24H,6,8-10,12H2,1-5H3/t14-,16+,21-,22-/m1/s1
SMILES:	CC1=CCC[C@H]2[C@@H](C)[C@](C)(CC[C@]12C)CC1=C(C(=O)C=C(C1=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477692
PubChem CID:	10066979
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	Hainan, China	n.a.	PMID[19091557]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]
NPO26203	Dysidea villosa	Species	Dysideidae	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	6
Others	8

Activity Type	# Activity
Cell Line	3
Individual Protein	7
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	Inhibition	=	26.0	%	PMID[536672]
NPT2945	Individual Protein	Phospholipase A2 group 1B	Sus scrofa	Inhibition	=	86.4	%	PMID[536672]
NPT2945	Individual Protein	Phospholipase A2 group 1B	Sus scrofa	IC50	=	400.0	nM	PMID[536672]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	Inhibition	=	100.0	%	PMID[536672]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	IC50	=	200.0	nM	PMID[536672]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	99.1	%	PMID[536672]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	100.0	nM	PMID[536672]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	5450.0	nM	PMID[536673]
NPT804	Cell Line	HT-22	Mus musculus	Survival	=	57.0	%	PMID[536674]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5200.0	nM	PMID[536675]
NPT27	Others	Unspecified		Inhibition	=	14.0	%	PMID[536672]
NPT2	Others	Unspecified		Inhibition	=	40.1	%	PMID[536672]
NPT2	Others	Unspecified		Inhibition	=	68.1	%	PMID[536672]
NPT2	Others	Unspecified		IC50	=	5200.0	nM	PMID[536672]

☑ 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 NPC132228 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	175
0.1-0.2	1180
0.2-0.3	4803
0.3-0.4	12783
0.4-0.5	12003
0.5-0.6	6993
0.6-0.7	3717
0.7-0.8	966
0.8-0.85	51
0.85-0.9	13
0.9-0.95	7
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC8518
1.0	High Similarity	NPC263997
0.975	High Similarity	NPC241512
0.975	High Similarity	NPC6185
0.9494	High Similarity	NPC474085
0.9494	High Similarity	NPC55869
0.9367	High Similarity	NPC108955
0.925	High Similarity	NPC99308
0.9136	High Similarity	NPC103486
0.9036	High Similarity	NPC133652
0.9036	High Similarity	NPC474680
0.8953	High Similarity	NPC474209
0.8953	High Similarity	NPC475823
0.8875	High Similarity	NPC30321
0.8861	High Similarity	NPC92080
0.8861	High Similarity	NPC26504
0.8795	High Similarity	NPC105803
0.878	High Similarity	NPC225515
0.8765	High Similarity	NPC27817
0.8642	High Similarity	NPC189485
0.8625	High Similarity	NPC1254
0.8608	High Similarity	NPC147438
0.8571	High Similarity	NPC53733
0.8554	High Similarity	NPC116797
0.8539	High Similarity	NPC263780
0.8523	High Similarity	NPC223093
0.8506	High Similarity	NPC53454
0.8444	Intermediate Similarity	NPC23170
0.8434	Intermediate Similarity	NPC2482
0.8427	Intermediate Similarity	NPC174167
0.8427	Intermediate Similarity	NPC470036
0.8415	Intermediate Similarity	NPC74410
0.8395	Intermediate Similarity	NPC110725
0.8395	Intermediate Similarity	NPC470525
0.8372	Intermediate Similarity	NPC33663
0.8372	Intermediate Similarity	NPC32037
0.8333	Intermediate Similarity	NPC278459
0.8333	Intermediate Similarity	NPC121984
0.8333	Intermediate Similarity	NPC475833
0.8313	Intermediate Similarity	NPC475681
0.8313	Intermediate Similarity	NPC192329
0.8295	Intermediate Similarity	NPC307298
0.8276	Intermediate Similarity	NPC94666
0.8272	Intermediate Similarity	NPC175079
0.8256	Intermediate Similarity	NPC237712
0.8222	Intermediate Similarity	NPC99380
0.8222	Intermediate Similarity	NPC26865
0.8214	Intermediate Similarity	NPC476809
0.8202	Intermediate Similarity	NPC65615
0.8202	Intermediate Similarity	NPC68148
0.8202	Intermediate Similarity	NPC112454
0.8193	Intermediate Similarity	NPC23778
0.8193	Intermediate Similarity	NPC476808
0.8182	Intermediate Similarity	NPC272039
0.8182	Intermediate Similarity	NPC220930
0.8182	Intermediate Similarity	NPC470523
0.8171	Intermediate Similarity	NPC180886
0.8161	Intermediate Similarity	NPC469993
0.8161	Intermediate Similarity	NPC90287
0.8152	Intermediate Similarity	NPC777
0.8152	Intermediate Similarity	NPC147232
0.814	Intermediate Similarity	NPC49019
0.8132	Intermediate Similarity	NPC211230
0.8125	Intermediate Similarity	NPC179208
0.8125	Intermediate Similarity	NPC474539
0.8118	Intermediate Similarity	NPC472684
0.8118	Intermediate Similarity	NPC44963
0.8111	Intermediate Similarity	NPC113393
0.8111	Intermediate Similarity	NPC129913
0.8095	Intermediate Similarity	NPC472490
0.8095	Intermediate Similarity	NPC476177
0.809	Intermediate Similarity	NPC470524
0.8072	Intermediate Similarity	NPC283087
0.8072	Intermediate Similarity	NPC476811
0.8072	Intermediate Similarity	NPC165711
0.8072	Intermediate Similarity	NPC472300
0.8068	Intermediate Similarity	NPC327115
0.8068	Intermediate Similarity	NPC203795
0.8068	Intermediate Similarity	NPC472974
0.8046	Intermediate Similarity	NPC144258
0.8046	Intermediate Similarity	NPC473246
0.8043	Intermediate Similarity	NPC474882
0.8043	Intermediate Similarity	NPC474328
0.8	Intermediate Similarity	NPC472478
0.8	Intermediate Similarity	NPC474918
0.8	Intermediate Similarity	NPC310010
0.8	Intermediate Similarity	NPC326627
0.8	Intermediate Similarity	NPC477973
0.8	Intermediate Similarity	NPC18955
0.7978	Intermediate Similarity	NPC230016
0.7976	Intermediate Similarity	NPC471409
0.7976	Intermediate Similarity	NPC478247
0.7976	Intermediate Similarity	NPC469996
0.7976	Intermediate Similarity	NPC321514
0.7976	Intermediate Similarity	NPC62336
0.7976	Intermediate Similarity	NPC275494
0.7976	Intermediate Similarity	NPC478246
0.7957	Intermediate Similarity	NPC295347
0.7955	Intermediate Similarity	NPC474537
0.7955	Intermediate Similarity	NPC255174
0.7955	Intermediate Similarity	NPC469948
0.7952	Intermediate Similarity	NPC263582
0.7935	Intermediate Similarity	NPC271652
0.7931	Intermediate Similarity	NPC8091
0.7931	Intermediate Similarity	NPC470015
0.7931	Intermediate Similarity	NPC168188
0.7927	Intermediate Similarity	NPC264178
0.7912	Intermediate Similarity	NPC38952
0.7907	Intermediate Similarity	NPC471898
0.7907	Intermediate Similarity	NPC475863
0.7907	Intermediate Similarity	NPC473217
0.7907	Intermediate Similarity	NPC149237
0.7907	Intermediate Similarity	NPC470034
0.7907	Intermediate Similarity	NPC189237
0.7907	Intermediate Similarity	NPC90055
0.7895	Intermediate Similarity	NPC147954
0.7889	Intermediate Similarity	NPC471722
0.7889	Intermediate Similarity	NPC58271
0.7889	Intermediate Similarity	NPC185059
0.7889	Intermediate Similarity	NPC72397
0.7889	Intermediate Similarity	NPC475001
0.7875	Intermediate Similarity	NPC262673
0.7865	Intermediate Similarity	NPC145879
0.7865	Intermediate Similarity	NPC20688
0.7865	Intermediate Similarity	NPC474732
0.7865	Intermediate Similarity	NPC474778
0.7865	Intermediate Similarity	NPC474733
0.7865	Intermediate Similarity	NPC118648
0.7865	Intermediate Similarity	NPC51014
0.7865	Intermediate Similarity	NPC31564
0.7865	Intermediate Similarity	NPC222613
0.7865	Intermediate Similarity	NPC475022
0.7857	Intermediate Similarity	NPC197659
0.7857	Intermediate Similarity	NPC257666
0.7857	Intermediate Similarity	NPC40170
0.7857	Intermediate Similarity	NPC266193
0.7857	Intermediate Similarity	NPC97377
0.7849	Intermediate Similarity	NPC245972
0.7849	Intermediate Similarity	NPC196485
0.7848	Intermediate Similarity	NPC243272
0.7841	Intermediate Similarity	NPC53385
0.7841	Intermediate Similarity	NPC321187
0.7841	Intermediate Similarity	NPC96095
0.7841	Intermediate Similarity	NPC85774
0.7841	Intermediate Similarity	NPC476412
0.7841	Intermediate Similarity	NPC58841
0.7841	Intermediate Similarity	NPC161423
0.7841	Intermediate Similarity	NPC329043
0.7841	Intermediate Similarity	NPC227064
0.7841	Intermediate Similarity	NPC214043
0.7826	Intermediate Similarity	NPC168027
0.7826	Intermediate Similarity	NPC185936
0.7826	Intermediate Similarity	NPC248913
0.7816	Intermediate Similarity	NPC327969
0.7816	Intermediate Similarity	NPC212083
0.7816	Intermediate Similarity	NPC302661
0.7816	Intermediate Similarity	NPC310989
0.7816	Intermediate Similarity	NPC321289
0.7816	Intermediate Similarity	NPC238991
0.7816	Intermediate Similarity	NPC260956
0.7816	Intermediate Similarity	NPC48362
0.7816	Intermediate Similarity	NPC193347
0.7816	Intermediate Similarity	NPC151519
0.7812	Intermediate Similarity	NPC472972
0.7812	Intermediate Similarity	NPC474720
0.7802	Intermediate Similarity	NPC36668
0.7802	Intermediate Similarity	NPC5509
0.7802	Intermediate Similarity	NPC184663
0.7802	Intermediate Similarity	NPC119416
0.7802	Intermediate Similarity	NPC1015
0.7802	Intermediate Similarity	NPC474245
0.7802	Intermediate Similarity	NPC280833
0.7802	Intermediate Similarity	NPC31985
0.7802	Intermediate Similarity	NPC118011
0.7791	Intermediate Similarity	NPC287063
0.7791	Intermediate Similarity	NPC104545
0.7791	Intermediate Similarity	NPC26139
0.7791	Intermediate Similarity	NPC469637
0.7789	Intermediate Similarity	NPC208094
0.7778	Intermediate Similarity	NPC291062
0.7778	Intermediate Similarity	NPC475740
0.7778	Intermediate Similarity	NPC94743
0.7778	Intermediate Similarity	NPC93778
0.7778	Intermediate Similarity	NPC58063
0.7778	Intermediate Similarity	NPC136548
0.7766	Intermediate Similarity	NPC280725
0.7765	Intermediate Similarity	NPC207772
0.7765	Intermediate Similarity	NPC475994
0.7755	Intermediate Similarity	NPC111323
0.7755	Intermediate Similarity	NPC131366
0.7753	Intermediate Similarity	NPC29447
0.7753	Intermediate Similarity	NPC79573
0.7753	Intermediate Similarity	NPC33881
0.7753	Intermediate Similarity	NPC311702
0.7753	Intermediate Similarity	NPC123319
0.7753	Intermediate Similarity	NPC476426
0.7753	Intermediate Similarity	NPC94531
0.775	Intermediate Similarity	NPC188292
0.775	Intermediate Similarity	NPC260474
0.775	Intermediate Similarity	NPC146376

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 NPC132228 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1560
0.2-0.3	3820
0.3-0.4	2484
0.4-0.5	699
0.5-0.6	201
0.6-0.7	140
0.7-0.8	80
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9125	High Similarity	NPD4695	Discontinued
0.8276	Intermediate Similarity	NPD5690	Phase 2
0.8202	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3617	Approved
0.8152	Intermediate Similarity	NPD5695	Phase 3
0.8068	Intermediate Similarity	NPD5279	Phase 3
0.8068	Intermediate Similarity	NPD5280	Approved
0.8068	Intermediate Similarity	NPD4694	Approved
0.8046	Intermediate Similarity	NPD4197	Approved
0.8	Intermediate Similarity	NPD4753	Phase 2
0.7955	Intermediate Similarity	NPD5329	Approved
0.7889	Intermediate Similarity	NPD5737	Approved
0.7889	Intermediate Similarity	NPD6672	Approved
0.7841	Intermediate Similarity	NPD3133	Approved
0.7841	Intermediate Similarity	NPD3666	Approved
0.7841	Intermediate Similarity	NPD3665	Phase 1
0.7816	Intermediate Similarity	NPD4223	Phase 3
0.7816	Intermediate Similarity	NPD4221	Approved
0.7816	Intermediate Similarity	NPD3667	Approved
0.7789	Intermediate Similarity	NPD6084	Phase 2
0.7789	Intermediate Similarity	NPD6083	Phase 2
0.7766	Intermediate Similarity	NPD4629	Approved
0.7766	Intermediate Similarity	NPD5210	Approved
0.7717	Intermediate Similarity	NPD5692	Phase 3
0.7708	Intermediate Similarity	NPD5696	Approved
0.7684	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5221	Approved
0.7684	Intermediate Similarity	NPD5222	Approved
0.7667	Intermediate Similarity	NPD3618	Phase 1
0.7667	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4786	Approved
0.7634	Intermediate Similarity	NPD6050	Approved
0.7634	Intermediate Similarity	NPD5694	Approved
0.7609	Intermediate Similarity	NPD6080	Approved
0.7609	Intermediate Similarity	NPD6673	Approved
0.7609	Intermediate Similarity	NPD6904	Approved
0.7604	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.7474	Intermediate Similarity	NPD7748	Approved
0.7473	Intermediate Similarity	NPD4689	Approved
0.7473	Intermediate Similarity	NPD4138	Approved
0.7473	Intermediate Similarity	NPD4693	Phase 3
0.7473	Intermediate Similarity	NPD4690	Approved
0.7473	Intermediate Similarity	NPD4688	Approved
0.7473	Intermediate Similarity	NPD5205	Approved
0.7473	Intermediate Similarity	NPD4519	Discontinued
0.7473	Intermediate Similarity	NPD4623	Approved
0.7449	Intermediate Similarity	NPD5286	Approved
0.7449	Intermediate Similarity	NPD4696	Approved
0.7449	Intermediate Similarity	NPD5285	Approved
0.7447	Intermediate Similarity	NPD5693	Phase 1
0.7447	Intermediate Similarity	NPD6079	Approved
0.7447	Intermediate Similarity	NPD7515	Phase 2
0.7447	Intermediate Similarity	NPD5284	Approved
0.7447	Intermediate Similarity	NPD5281	Approved
0.7444	Intermediate Similarity	NPD3668	Phase 3
0.7423	Intermediate Similarity	NPD4755	Approved
0.7419	Intermediate Similarity	NPD5328	Approved
0.7374	Intermediate Similarity	NPD5223	Approved
0.7368	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD5133	Approved
0.7353	Intermediate Similarity	NPD5697	Approved
0.7349	Intermediate Similarity	NPD4691	Approved
0.7342	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5224	Approved
0.73	Intermediate Similarity	NPD4633	Approved
0.73	Intermediate Similarity	NPD5226	Approved
0.73	Intermediate Similarity	NPD5225	Approved
0.73	Intermediate Similarity	NPD5211	Phase 2
0.7284	Intermediate Similarity	NPD3704	Approved
0.7284	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7146	Approved
0.7283	Intermediate Similarity	NPD7521	Approved
0.7283	Intermediate Similarity	NPD6684	Approved
0.7283	Intermediate Similarity	NPD5330	Approved
0.7283	Intermediate Similarity	NPD6409	Approved
0.7283	Intermediate Similarity	NPD7334	Approved
0.7283	Intermediate Similarity	NPD6098	Approved
0.7282	Intermediate Similarity	NPD6011	Approved
0.7282	Intermediate Similarity	NPD6899	Approved
0.7282	Intermediate Similarity	NPD6881	Approved
0.7273	Intermediate Similarity	NPD4195	Approved
0.7273	Intermediate Similarity	NPD4700	Approved
0.7255	Intermediate Similarity	NPD6402	Approved
0.7255	Intermediate Similarity	NPD6675	Approved
0.7255	Intermediate Similarity	NPD5739	Approved
0.7255	Intermediate Similarity	NPD7128	Approved
0.7245	Intermediate Similarity	NPD7902	Approved
0.7241	Intermediate Similarity	NPD4756	Discovery
0.7229	Intermediate Similarity	NPD4137	Phase 3
0.7228	Intermediate Similarity	NPD5175	Approved
0.7228	Intermediate Similarity	NPD5174	Approved
0.7216	Intermediate Similarity	NPD5654	Approved
0.7212	Intermediate Similarity	NPD6013	Approved
0.7212	Intermediate Similarity	NPD6014	Approved
0.7212	Intermediate Similarity	NPD6012	Approved
0.7204	Intermediate Similarity	NPD3573	Approved
0.7191	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4202	Approved
0.7184	Intermediate Similarity	NPD5701	Approved
0.7158	Intermediate Similarity	NPD4096	Approved
0.7157	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD7614	Phase 1
0.7143	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD4747	Approved
0.7143	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD6883	Approved
0.7129	Intermediate Similarity	NPD5091	Approved
0.7128	Intermediate Similarity	NPD6903	Approved
0.7128	Intermediate Similarity	NPD4518	Approved
0.7128	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7320	Approved
0.7113	Intermediate Similarity	NPD5282	Discontinued
0.7111	Intermediate Similarity	NPD4139	Approved
0.7111	Intermediate Similarity	NPD4692	Approved
0.7093	Intermediate Similarity	NPD5733	Approved
0.7093	Intermediate Similarity	NPD4058	Approved
0.7093	Intermediate Similarity	NPD4687	Approved
0.7075	Intermediate Similarity	NPD6650	Approved
0.7075	Intermediate Similarity	NPD6649	Approved
0.7075	Intermediate Similarity	NPD6869	Approved
0.7075	Intermediate Similarity	NPD6847	Approved
0.7075	Intermediate Similarity	NPD8130	Phase 1
0.7075	Intermediate Similarity	NPD6617	Approved
0.7071	Intermediate Similarity	NPD5959	Approved
0.7059	Intermediate Similarity	NPD5276	Approved
0.7059	Intermediate Similarity	NPD4754	Approved
0.7048	Intermediate Similarity	NPD6372	Approved
0.7048	Intermediate Similarity	NPD6373	Approved
0.7033	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.6979	Remote Similarity	NPD5207	Approved
0.697	Remote Similarity	NPD7732	Phase 3
0.6952	Remote Similarity	NPD5128	Approved
0.6952	Remote Similarity	NPD4729	Approved
0.6952	Remote Similarity	NPD5168	Approved
0.6952	Remote Similarity	NPD4730	Approved
0.6947	Remote Similarity	NPD5208	Approved
0.6939	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7900	Approved
0.6923	Remote Similarity	NPD4767	Approved
0.6923	Remote Similarity	NPD4768	Approved
0.6916	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6411	Approved
0.6869	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7331	Phase 2
0.6822	Remote Similarity	NPD5248	Approved
0.6822	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5247	Approved
0.6822	Remote Similarity	NPD5251	Approved
0.6822	Remote Similarity	NPD5169	Approved
0.6822	Remote Similarity	NPD5250	Approved
0.6822	Remote Similarity	NPD5135	Approved
0.6822	Remote Similarity	NPD4634	Approved
0.6822	Remote Similarity	NPD5249	Phase 3
0.6818	Remote Similarity	NPD6274	Approved
0.6818	Remote Similarity	NPD6868	Approved
0.6809	Remote Similarity	NPD1696	Phase 3
0.6789	Remote Similarity	NPD4632	Approved
0.6759	Remote Similarity	NPD5217	Approved
0.6759	Remote Similarity	NPD5216	Approved
0.6759	Remote Similarity	NPD5215	Approved
0.6759	Remote Similarity	NPD5127	Approved
0.6757	Remote Similarity	NPD6317	Approved
0.6757	Remote Similarity	NPD6009	Approved
0.6747	Remote Similarity	NPD7341	Phase 2
0.6742	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6101	Approved
0.6698	Remote Similarity	NPD6412	Phase 2
0.6698	Remote Similarity	NPD6614	Approved
0.6696	Remote Similarity	NPD6335	Approved
0.6696	Remote Similarity	NPD6314	Approved
0.6696	Remote Similarity	NPD6313	Approved
0.6637	Remote Similarity	NPD7100	Approved
0.6637	Remote Similarity	NPD7101	Approved
0.6632	Remote Similarity	NPD1694	Approved
0.6629	Remote Similarity	NPD6942	Approved
0.6629	Remote Similarity	NPD7339	Approved
0.6602	Remote Similarity	NPD6404	Discontinued
0.66	Remote Similarity	NPD6001	Approved
0.6596	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6319	Approved
0.6579	Remote Similarity	NPD6054	Approved
0.6577	Remote Similarity	NPD5167	Approved
0.6559	Remote Similarity	NPD8028	Phase 2
0.6522	Remote Similarity	NPD6015	Approved
0.6522	Remote Similarity	NPD7645	Phase 2
0.6522	Remote Similarity	NPD6016	Approved
0.6522	Remote Similarity	NPD5983	Phase 2
0.6517	Remote Similarity	NPD4784	Approved
0.6517	Remote Similarity	NPD4785	Approved
0.6505	Remote Similarity	NPD7638	Approved
0.6477	Remote Similarity	NPD4243	Approved
0.6466	Remote Similarity	NPD5988	Approved
0.6466	Remote Similarity	NPD6370	Approved
0.646	Remote Similarity	NPD7115	Discovery

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