NPASS drugs

Drug Information

Drug ID:	NPD802
Drug Name:	Psilocybine
Molecular Formula:	C12H17N2O4P
Canonical SMILES:	CN(CCc1c[nH]c2c1c(ccc2)OP(=O)(O)O)C
Standard InCHI:	InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)
Standard InCHIKey:	QVDSEJDULKLHCG-UHFFFAOYSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD802

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
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	382
0.1-0.2	3327
0.2-0.3	9370
0.3-0.4	11709
0.4-0.5	3050
0.5-0.6	1514
0.6-0.7	1105
0.7-0.8	395
0.8-0.85	29
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC106937
High Similarity	0.8933	NPC46580
High Similarity	0.8696	NPC242209
High Similarity	0.8696	NPC13880
High Similarity	0.8667	NPC171171
High Similarity	0.8611	NPC314002
High Similarity	0.8588	NPC96890
High Similarity	0.8556	NPC204717
High Similarity	0.85	NPC220765
Intermediate Similarity	0.8387	NPC307963
Intermediate Similarity	0.8378	NPC92111
Intermediate Similarity	0.8333	NPC42979
Intermediate Similarity	0.8333	NPC99666
Intermediate Similarity	0.8324	NPC224764
Intermediate Similarity	0.8324	NPC76748
Intermediate Similarity	0.8316	NPC121772
Intermediate Similarity	0.8315	NPC474409
Intermediate Similarity	0.8278	NPC184964
Intermediate Similarity	0.8276	NPC131718
Intermediate Similarity	0.827	NPC296527
Intermediate Similarity	0.8254	NPC156704
Intermediate Similarity	0.8245	NPC326634
Intermediate Similarity	0.8232	NPC72980
Intermediate Similarity	0.8201	NPC251090
Intermediate Similarity	0.81	NPC170114
Intermediate Similarity	0.8083	NPC232727
Intermediate Similarity	0.8079	NPC102423
Intermediate Similarity	0.8075	NPC32771
Intermediate Similarity	0.8063	NPC77555
Intermediate Similarity	0.8051	NPC285558
Intermediate Similarity	0.805	NPC470549
Intermediate Similarity	0.804	NPC316981
Intermediate Similarity	0.804	NPC128084
Intermediate Similarity	0.803	NPC11464
Intermediate Similarity	0.8011	NPC230869
Intermediate Similarity	0.8011	NPC313791
Intermediate Similarity	0.8011	NPC94943
Intermediate Similarity	0.8	NPC212535
Intermediate Similarity	0.7959	NPC475070
Intermediate Similarity	0.7957	NPC190007
Intermediate Similarity	0.7957	NPC84478
Intermediate Similarity	0.7938	NPC213308
Intermediate Similarity	0.7938	NPC315491
Intermediate Similarity	0.7938	NPC45459
Intermediate Similarity	0.7902	NPC310118
Intermediate Similarity	0.7889	NPC80596
Intermediate Similarity	0.7889	NPC160105
Intermediate Similarity	0.7886	NPC469760
Intermediate Similarity	0.7886	NPC469786
Intermediate Similarity	0.7886	NPC469765
Intermediate Similarity	0.7886	NPC25008
Intermediate Similarity	0.7886	NPC259644
Intermediate Similarity	0.7886	NPC73952
Intermediate Similarity	0.7886	NPC469763
Intermediate Similarity	0.7877	NPC311276
Intermediate Similarity	0.7853	NPC324149
Intermediate Similarity	0.7846	NPC176538
Intermediate Similarity	0.7841	NPC75540
Intermediate Similarity	0.7841	NPC70922
Intermediate Similarity	0.7841	NPC211572
Intermediate Similarity	0.7841	NPC212376
Intermediate Similarity	0.7841	NPC80597
Intermediate Similarity	0.7821	NPC282231
Intermediate Similarity	0.7817	NPC200836
Intermediate Similarity	0.7814	NPC314603
Intermediate Similarity	0.7799	NPC110151
Intermediate Similarity	0.779	NPC474561
Intermediate Similarity	0.779	NPC49954
Intermediate Similarity	0.7789	NPC88008
Intermediate Similarity	0.7789	NPC183777
Intermediate Similarity	0.7784	NPC153042
Intermediate Similarity	0.7771	NPC105818
Intermediate Similarity	0.7771	NPC24678
Intermediate Similarity	0.7765	NPC279918
Intermediate Similarity	0.7761	NPC167860
Intermediate Similarity	0.7761	NPC123976
Intermediate Similarity	0.7761	NPC5145
Intermediate Similarity	0.7756	NPC264285
Intermediate Similarity	0.7755	NPC19872
Intermediate Similarity	0.7753	NPC469762
Intermediate Similarity	0.7746	NPC314372
Intermediate Similarity	0.7746	NPC159856
Intermediate Similarity	0.7734	NPC266931
Intermediate Similarity	0.7733	NPC190296
Intermediate Similarity	0.7718	NPC213530
Intermediate Similarity	0.7718	NPC193267
Intermediate Similarity	0.7713	NPC176127
Intermediate Similarity	0.7704	NPC476167
Intermediate Similarity	0.7697	NPC469785
Intermediate Similarity	0.7692	NPC243834
Intermediate Similarity	0.7692	NPC70956
Intermediate Similarity	0.7692	NPC16352
Intermediate Similarity	0.768	NPC131017
Intermediate Similarity	0.7665	NPC329747
Intermediate Similarity	0.7665	NPC249040
Intermediate Similarity	0.7665	NPC315957
Intermediate Similarity	0.7662	NPC476465
Intermediate Similarity	0.7661	NPC73767
Intermediate Similarity	0.7653	NPC192315
Intermediate Similarity	0.7653	NPC306376
Intermediate Similarity	0.765	NPC63751
Intermediate Similarity	0.7647	NPC88363
Intermediate Similarity	0.7644	NPC60621
Intermediate Similarity	0.7641	NPC222018
Intermediate Similarity	0.7635	NPC246518
Intermediate Similarity	0.7632	NPC188387
Intermediate Similarity	0.7632	NPC163421
Intermediate Similarity	0.7624	NPC174672
Intermediate Similarity	0.7619	NPC469358
Intermediate Similarity	0.7604	NPC128751
Intermediate Similarity	0.7604	NPC246700
Intermediate Similarity	0.7596	NPC54988
Intermediate Similarity	0.7594	NPC111275
Intermediate Similarity	0.7582	NPC194640
Intermediate Similarity	0.7582	NPC40779
Intermediate Similarity	0.7574	NPC475910
Intermediate Similarity	0.7573	NPC142901
Intermediate Similarity	0.7573	NPC148183
Intermediate Similarity	0.7573	NPC152768
Intermediate Similarity	0.7566	NPC71037
Intermediate Similarity	0.7565	NPC106833
Intermediate Similarity	0.7565	NPC95783
Intermediate Similarity	0.7565	NPC469497
Intermediate Similarity	0.7563	NPC72211
Intermediate Similarity	0.7561	NPC477610
Intermediate Similarity	0.7558	NPC110126
Intermediate Similarity	0.7551	NPC70259
Intermediate Similarity	0.755	NPC53144
Intermediate Similarity	0.7549	NPC208284
Intermediate Similarity	0.7544	NPC84911
Intermediate Similarity	0.7541	NPC471178
Intermediate Similarity	0.7536	NPC476041
Intermediate Similarity	0.7536	NPC304926
Intermediate Similarity	0.7514	NPC469780
Intermediate Similarity	0.7514	NPC469767
Intermediate Similarity	0.7514	NPC469761
Intermediate Similarity	0.7514	NPC469783
Intermediate Similarity	0.7514	NPC469784
Intermediate Similarity	0.7514	NPC469768
Intermediate Similarity	0.7514	NPC469779
Intermediate Similarity	0.7512	NPC470500
Intermediate Similarity	0.7512	NPC219087
Intermediate Similarity	0.75	NPC24370
Intermediate Similarity	0.75	NPC205934
Intermediate Similarity	0.75	NPC43787
Intermediate Similarity	0.75	NPC141353
Intermediate Similarity	0.75	NPC248454
Intermediate Similarity	0.75	NPC477609
Intermediate Similarity	0.75	NPC84827
Intermediate Similarity	0.75	NPC14113
Intermediate Similarity	0.75	NPC475112
Intermediate Similarity	0.75	NPC475085
Intermediate Similarity	0.75	NPC145885
Intermediate Similarity	0.75	NPC291535
Intermediate Similarity	0.75	NPC276517
Intermediate Similarity	0.75	NPC319232
Intermediate Similarity	0.7488	NPC171787
Intermediate Similarity	0.7488	NPC183407
Intermediate Similarity	0.7485	NPC96102
Intermediate Similarity	0.7485	NPC29886
Intermediate Similarity	0.7485	NPC261195
Intermediate Similarity	0.7476	NPC471080
Intermediate Similarity	0.7476	NPC469592
Intermediate Similarity	0.7474	NPC233936
Intermediate Similarity	0.7471	NPC469766
Intermediate Similarity	0.7463	NPC245816
Intermediate Similarity	0.7463	NPC476138
Intermediate Similarity	0.7463	NPC162484
Intermediate Similarity	0.7459	NPC78020
Intermediate Similarity	0.7458	NPC471957
Intermediate Similarity	0.7451	NPC185782
Intermediate Similarity	0.7448	NPC15102
Intermediate Similarity	0.7447	NPC267885
Intermediate Similarity	0.7443	NPC477861
Intermediate Similarity	0.7442	NPC105127
Intermediate Similarity	0.7438	NPC193777
Intermediate Similarity	0.7435	NPC48938
Intermediate Similarity	0.7427	NPC26679
Intermediate Similarity	0.7419	NPC256828
Intermediate Similarity	0.7418	NPC92796
Intermediate Similarity	0.7418	NPC135141
Intermediate Similarity	0.7416	NPC469594
Intermediate Similarity	0.7409	NPC315555
Intermediate Similarity	0.7409	NPC235684
Intermediate Similarity	0.7407	NPC59269
Intermediate Similarity	0.7406	NPC122436
Intermediate Similarity	0.74	NPC470497
Intermediate Similarity	0.74	NPC329793
Intermediate Similarity	0.7396	NPC284678
Intermediate Similarity	0.7395	NPC326363
Intermediate Similarity	0.7394	NPC110500
Intermediate Similarity	0.7394	NPC149155
Intermediate Similarity	0.7394	NPC203468
Intermediate Similarity	0.7393	NPC473317
Intermediate Similarity	0.7391	NPC476118
Intermediate Similarity	0.7389	NPC200214
Intermediate Similarity	0.7387	NPC470499
Intermediate Similarity	0.7381	NPC74360
Intermediate Similarity	0.738	NPC470498
Intermediate Similarity	0.7376	NPC476098

Drug Structure

NPD802 OpenBabel08201723412D 22 23 0 0 0 0 0 0 0 0999 V2000 -2.2076 0.0674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3666 -1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7213 -1.2708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -1.5798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0827 -2.9345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0219 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8309 -3.3412 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4155 -0.9107 0.0000 N 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 -1.0000 0.0000 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 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 1.0388 -4.3194 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 13 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 18 19 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	284.09
ALogP	-0.3315
MLogP	2.01
XLogP	-0.053
HDA	5
HBD	3
Rotatable Bonds	9
TPSA	95.6
RO5 Violation	0