EMNPD

NPs Basic Information
NPs Species Source
NPs Content
NPs Biological Activity
NPs Physi-Chem Properties
NPs ADMET Properties
Similar NPs and Drugs

NPs Basic Information

Download MOL File	Name	(+)-Shikonin
	Molecular Formula	C16H16O5
	IUPAC Name*	5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
	SMILES	CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
	InChI	InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1
	InChIKey	NEZONWMXZKDMKF-SNVBAGLBSA-N
	Synonyms	shikonin; 517-89-5; (R)-5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione; Isoarnebin 4; Tokyo Violet; (+)-Shikonin; 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione; NSC 252844; Shikonine; CHEBI:81068; 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione; C.I. 75535; Shikonin S; 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dihydronaphthalene-1,4-dione; SR-05000001466; UNII-3IK6592UBW; CCRIS 6492; HSDB 8100; (R)-Shikonin; Shikonin,(S); BRN 2058010; SCHEMBL33969; BSPBio_001270; MLS006010149; DTXSID30199653; HMS1792P11; HMS1990P11; HMS2089L09; HMS3403P11; AMY39404; HY-N0822; ZINC2015152; MFCD00075680; s8279; (+)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone; AKOS015900416; CCG-208272; CS-5906; NCGC00163489-01; NCGC00163489-02; NCGC00163489-04; NCGC00163489-05; AC-26871; AS-13554; BP-30212; SMR002530673; C15906; 517S895; J-502235; SR-05000001466-1; SR-05000001466-3; Q27155024
	CAS	517-89-5
	PubChem CID	479503
	ChEMBL ID	NA

*Note: the IUPAC Name was collected from PubChem.

Chemical Classification:	Kingdom: Organic compounds Superclass: Benzenoids Class: Naphthalenes Subclass: Naphthoquinones Direct Parent: Naphthoquinones	ClassyFire Version 1.0 PMID:27867422

NPs Species Source

	Endophyte ID	Endophyte Name	Family	Genus	Taxonomy ID	GenBank ID	Closest GenBank ID	Reference
	Endophyte ID	Endophyte Name	Family	Genus	Taxonomy ID	GenBank ID	Closest GenBank ID	Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.

**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

	Bioactivity Name	Target ID	Target Name	Target Type	Target Organism	Target Organism ID	Potency of Bioactivity	Activity Type	Value	Unit	Endophyte ID	Endophyte Name
	Bioactivity Name	Target ID	Target Name	Target Type	Target Organism	Target Organism ID	Potency of Bioactivity	Activity Type	Value	Unit	Endophyte ID	Endophyte Name

NPs Physi-Chem Properties

Molecular Weight:	288.29	ALogp:	3.0
HBD:	3	HBA:	5
Rotatable Bonds:	3	Lipinski's rule of five:	Accepted
Polar Surface Area:	94.8	Aromatic Rings:	2
Heavy Atoms:	21	QED Weighted:	0.587

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability:	-4.909	MDCK Permeability:	0.00000832
Pgp-inhibitor:	0.01	Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.021	20% Bioavailability (F20%):	0.847
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	Plasma Protein Binding (PPB):	96.12%
Volume Distribution (VD):	0.681	Fu:	5.41%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953	CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.259	CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.719	CYP2C9-substrate:	0.741
CYP2D6-inhibitor:	0.716	CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.149	CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):

17.16

Half-life (T1/2):

0.783

ADMET: Toxicity

hERG Blockers:	0.008	Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.805	AMES Toxicity:	0.766
Rat Oral Acute Toxicity:	0.442	Maximum Recommended Daily Dose:	0.294
Skin Sensitization:	0.922	Carcinogencity:	0.454
Eye Corrosion:	0.033	Eye Irritation:	0.942
Respiratory Toxicity:	0.401

*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs					Similar Drugs
NPs ID	NPs 2D Structure	Similarity Score			TTD ID	Drug 2D Structure	Similarity Score
ENC002125		0.403			D04PHC		0.300
ENC004048		0.397			D0I8FI		0.297
ENC005353		0.369			D08FPM		0.296
ENC005576		0.343			D07MOX		0.294
ENC000087		0.342			D0R3JB		0.281
ENC004888		0.342			D08HVR		0.274
ENC005342		0.337			D0BA6T		0.267
ENC000929		0.337			D0I3RO		0.267
ENC000337		0.333			D0V9EN		0.264
ENC000934		0.333			D0U0OT		0.263

*Note: the compound similarity was calculated by RDKIT.