NPASS Natural Product

Natural Product: NPC10572

Natural Product ID:	NPC10572
Common Name:	Caucanolide A
IUPAC Name:	2-[2-[(2S)-2-[(1R)-1-[(2R)-2-methoxy-4-methyl-5-oxofuran-2-yl]-2-methylprop-2-enyl]-5-oxo-2H-furan-4-yl]ethyl]-3-methylbut-2-enal
Synonyms:
Molecular Formula:	C21H26O6
Standard InCHIKey:	IYTPQKWQKYLEMT-WAOWUJCRSA-N
Standard InCHI:	InChI=1S/C21H26O6/c1-12(2)16(11-22)8-7-15-9-17(26-20(15)24)18(13(3)4)21(25-6)10-14(5)19(23)27-21/h9-11,17-18H,3,7-8H2,1-2,4-6H3/t17-,18+,21+/m0/s1
Canonical SMILES:	O=CC(=C(C)C)CCC1=C[C@H](OC1=O)[C@H]([C@]1(OC)OC(=O)C(=C1)C)C(=C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO24562	Saussurea petrovii	Species	Asteraceae	Eukaryota	UNPD*
NPO24654	Curculigo crassifolia	Species	Hypoxidaceae	Eukaryota	UNPD*
NPO25544	Encyclia michuacana	Species	Orchidaceae	Eukaryota	UNPD*
NPO25930	Cystoseira balearica	Species	Sargassaceae	Eukaryota	UNPD*
NPO26421	Urtica laetevirens	Species	Urticaceae	Eukaryota	UNPD*
NPO3843	Rhododendron metternichii	Species	Ericaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	5
Others	1

Activity Type	# Activity
Cell Line	4
Organism	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	25.8	ug/ml	16252918
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	12.5	ug/ml	16252918
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	25.5	ug/ml	16252918
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	17	ug/ml	16252918
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7.6	ug/ml	16252918
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Activity	=	21	%	16252918

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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 NPC10572 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	107
0.1-0.2	1004
0.2-0.3	4528
0.3-0.4	11976
0.4-0.5	7463
0.5-0.6	4245
0.6-0.7	1403
0.7-0.8	153
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.6932	Remote Similarity	NPC149869
0.6932	Remote Similarity	NPC475100
0.6932	Remote Similarity	NPC163093
0.6932	Remote Similarity	NPC159635
0.6932	Remote Similarity	NPC191476

Showing 1 to 5 of 200 entries

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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 NPC10572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	1707
0.2-0.3	4335
0.3-0.4	2195
0.4-0.5	581
0.5-0.6	184
0.6-0.7	28
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.56	Remote Similarity	NPD5693	Phase 1
0.56	Remote Similarity	NPD7637	Suspended
0.5612	Remote Similarity	NPD5737	Approved
0.5612	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6672	Approved

Showing 1 to 5 of 71 entries

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Structure

CID10572 OpenBabel06191715332D 27 28 0 0 1 0 0 0 0 0999 V2000 8.0584 1.7416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7713 2.9006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9675 -1.2791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2449 -1.0980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0351 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2887 2.6152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7639 0.6712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4330 1.4143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0426 0.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2531 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7202 0.2554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0803 1.9496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1585 -0.6913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1441 1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7857 0.8791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4111 1.2064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1766 0.7100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2630 0.3032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9877 0.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3790 1.7926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4540 0.8910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0510 -0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6948 -0.5507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8790 2.6587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8691 1.8008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3845 1.6881 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 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 25 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 22 2 0 0 0 0 12 16 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 17 18 1 1 0 0 0 17 26 1 0 0 0 0 18 13 1 1 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 1 0 0 0 21 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11624964
ChEMBL	CHEMBL463760
ZINC

Physicochemical Properties

Molecular Weight:	374.17
ALogP:	3.0628
MLogP:	3.11
XLogP:	2.034
# Rotatable Bonds:	13
Polar Surface Area:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	27

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