NPASS Natural Product

Natural Product: NPC209229

Natural Product ID:	NPC209229
Common Name:	Caruilignan C
IUPAC Name:	(3R,3aR,6aR)-3-(3,4,5-trimethoxyphenyl)-3,3a,4,6a-tetrahydro-1H-furo[3,4-c]furan-6-one
Synonyms:	Caruilignan C
Molecular Formula:	C15H18O6
Standard InCHIKey:	BYXOLWYJKZALLQ-KWBADKCTSA-N
Standard InCHI:	InChI=1S/C15H18O6/c1-17-11-4-8(5-12(18-2)14(11)19-3)13-9-6-21-15(16)10(9)7-20-13/h4-5,9-10,13H,6-7H2,1-3H3/t9-,10-,13-/m0/s1
Canonical SMILES:	COc1cc(cc(c1OC)OC)[C@@H]1OC[C@H]2[C@@H]1COC2=O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota				TCMID*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota				TCM_Taiwan*

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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	>	4	ug/ml	12141878

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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 NPC209229 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	246
0.1-0.2	1012
0.2-0.3	2272
0.3-0.4	5306
0.4-0.5	7848
0.5-0.6	3232
0.6-0.7	5799
0.7-0.8	4843
0.8-0.85	240
0.85-0.9	80
0.9-0.95	11
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.8217	Intermediate Similarity	NPC42230
0.8219	Intermediate Similarity	NPC318286
0.8219	Intermediate Similarity	NPC184702
0.8219	Intermediate Similarity	NPC327651
0.8219	Intermediate Similarity	NPC470932

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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 NPC209229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	827
0.2-0.3	1739
0.3-0.4	2675
0.4-0.5	1880
0.5-0.6	1171
0.6-0.7	505
0.7-0.8	117
0.8-0.85	5
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
0.6774	Remote Similarity	NPD5763	Approved
0.6776	Remote Similarity	NPD3657	Discovery
0.6776	Remote Similarity	NPD5124	Phase 1
0.6776	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1008	Clinical (unspecified phase)

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Structure

CID209229 OpenBabel06191716002D 21 23 0 0 1 0 0 0 0 0999 V2000 -0.2044 -3.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3359 0.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7360 -2.4170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0047 -1.1968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6998 0.3855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8239 2.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6319 0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1092 -0.2023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2306 1.1826 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2252 1.2871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9089 -1.6035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6134 -0.0212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0227 0.2045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7179 -1.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4331 2.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3466 2.6720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0134 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4224 0.5666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6315 -1.4225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8888 -0.2955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5670 2.7653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 21 1 0 0 0 0 7 20 1 0 0 0 0 9 6 1 1 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 7 1 1 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 8 1 1 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10685181
ChEMBL	CHEMBL508457
ZINC

Physicochemical Properties

Molecular Weight:	294.11
ALogP:	-0.8786
MLogP:	2.45
XLogP:	0.543
# Rotatable Bonds:	7
Polar Surface Area:	63.22
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	21

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