NPASS drugs

Drug Information

Drug ID:	NPD5124
Drug Name:	Calanolide A
Molecular Formula:	C22H26O5
Canonical SMILES:	CCCc1cc(=O)oc2c1c1OC(C)(C)C=Cc1c1c2[C@@H](O)[C@@H]([C@H](O1)C)C
Standard InCHI:	"InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1"
Standard InCHIKey:	NIDRYBLTWYFCFV-FMTVUPSXSA-N
Max Developmental Stage:	Phase 1
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5124

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	70133
0.1-0.2	136985
0.2-0.3	4361
0.3-0.4	186
0.4-0.5	40
0.5-0.6	6
0.6-0.7	15
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	8

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC141822
High Similarity	1.0	NPC1220
High Similarity	1.0	NPC205797
High Similarity	1.0	NPC142563
High Similarity	1.0	NPC241165
High Similarity	1.0	NPC602236
High Similarity	1.0	NPC607427
High Similarity	1.0	NPC607509
Intermediate Similarity	0.7941	NPC505625
Intermediate Similarity	0.7941	NPC513757
Intermediate Similarity	0.7941	NPC603144
Intermediate Similarity	0.7746	NPC571700
Intermediate Similarity	0.7746	NPC596099
Remote Similarity	0.6944	NPC469965
Remote Similarity	0.6933	NPC139595
Remote Similarity	0.6933	NPC60704
Remote Similarity	0.6892	NPC201820
Remote Similarity	0.6667	NPC293642
Remote Similarity	0.6667	NPC495385
Remote Similarity	0.6282	NPC35501
Remote Similarity	0.6282	NPC137262
Remote Similarity	0.6282	NPC144512
Remote Similarity	0.6282	NPC278600
Remote Similarity	0.6282	NPC37428
Remote Similarity	0.6282	NPC47040
Remote Similarity	0.6282	NPC602052
Remote Similarity	0.6282	NPC608910
Remote Similarity	0.6282	NPC610179
Remote Similarity	0.5974	NPC38153
Remote Similarity	0.5974	NPC505233
Remote Similarity	0.5625	NPC273548
Remote Similarity	0.5625	NPC149061
Remote Similarity	0.5625	NPC592156
Remote Similarity	0.5443	NPC291551

Drug Structure

NPD5124 OpenBabel08211706322D 28 31 0 0 1 0 0 0 0 0999 V2000 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 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 -1.7321 0.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -4.3301 -3.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 7 1 0 0 0 0 7 13 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 22 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 2 1 6 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 3 1 1 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 24 1 1 0 0 0 19 25 1 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB04886
ChEMBL	CHEMBL267447
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI	65552
CAS Number	142632-32-4

Drug Properties

Molecular Weight	370.18
ALogP	0.2774
MLogP	3.33
XLogP	3.505
HDA	2
HBD	1
Rotatable Bonds	8
TPSA	64.99
RO5 Violation	0