NPASS Natural Product

Natural Product: NPC18074

Natural Product ID:	NPC18074
Common Name:	(-)-Rosmarinic Acid
IUPAC Name:	(2S)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid
Synonyms:
Molecular Formula:	C18H16O8
Standard InCHIKey:	DOUMFZQKYFQNTF-GIZXNFQBSA-N
Standard InCHI:	InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m0/s1
Canonical SMILES:	O=C(O[C@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c(c1)O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	UNPD*
NPO10155	Stauntonia obovatifoliola	Species	Lardizabalaceae	Eukaryota	UNPD*
NPO10211	Pajanelia multijuga	NA	NA	NA	UNPD*
NPO10263	Alternaria tagetica	Species	Pleosporaceae	Eukaryota	UNPD*
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	TM-MC*
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	UNPD*
NPO10497	Hydrolithon reinboldii	Species	Corallinaceae	Eukaryota	UNPD*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	TM-MC*
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	UNPD*
NPO10946	Scedosporium boydii	Species	Microascaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	20100	nM	24360605

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Similar Natural Products 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 NPC18074 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	208
0.1-0.2	893
0.2-0.3	1952
0.3-0.4	4580
0.4-0.5	7704
0.5-0.6	3910
0.6-0.7	6236
0.7-0.8	4903
0.8-0.85	363
0.85-0.9	93
0.9-0.95	41
0.95-1	6

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Similarity Score	Similarity Level	Natural Product ID
0.8413	Intermediate Similarity	NPC233669
0.8417	Intermediate Similarity	NPC205195
0.8417	Intermediate Similarity	NPC321638
0.8417	Intermediate Similarity	NPC321184
0.8417	Intermediate Similarity	NPC171134

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Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC18074 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	759
0.2-0.3	1430
0.3-0.4	2448
0.4-0.5	2203
0.5-0.6	1301
0.6-0.7	667
0.7-0.8	134
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6831	Remote Similarity	NPD1281	Approved
0.6835	Remote Similarity	NPD3687	Approved
0.6835	Remote Similarity	NPD3686	Approved
0.6839	Remote Similarity	NPD7440	Discontinued
0.6842	Remote Similarity	NPD2355	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID18074 OpenBabel06191715342D 26 27 0 0 1 0 0 0 0 0999 V2000 6.0622 4.5000 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 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 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 3.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 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 4.5000 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 7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 1 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 10 1 0 0 0 0 2 5 2 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 9 1 1 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	639655
ChEMBL	CHEMBL3098862
ZINC

Physicochemical Properties

Molecular Weight:	360.08
ALogP:	-1.9057
MLogP:	2.56
XLogP:	2.083
# Rotatable Bonds:	12
Polar Surface Area:	144.52
# H-Bond Aceptor:	4
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	26

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