NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	656.27
Volume:	626.541
LogP:	-0.486
LogD:	-0.096
LogS:	-2.691
# Rotatable Bonds:	14
TPSA:	259.45
# H-Bond Aceptor:	15
# H-Bond Donor:	11
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.1
Synthetic Accessibility Score:	4.739
Fsp3:	0.613
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.519
MDCK Permeability:	2.7676764148054644e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.989
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	92.86751556396484%
Volume Distribution (VD):	0.297
Pgp-substrate:	7.214714527130127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.188
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	1.331
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.423
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.097
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.921
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.009

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC106937

Natural Product ID:	NPC106937
*Common Name:**	Psilocybine
IUPAC Name:	[3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate
Synonyms:	CY-39; Psilocybine
Standard InCHIKey:	QVDSEJDULKLHCG-UHFFFAOYSA-N
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)
SMILES:	CN(CCc1c[nH]c2c1c(ccc2)OP(=O)(O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL194378
PubChem CID:	10624
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000183] Tryptamines and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO19207	Anthenea chinensis	Species	n.a.	n.a.	n.a.	at a depth of 2-20 m, Sanya Bay in the South China Sea	2007-OCT	PMID[20184290]
NPO29771	Psilocybe	Genus	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25007546]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21155	Coleophoma crateriformis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20409	Mostuea buchholzii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5920	Phegopteris decursivipinnata	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20549	Ulmus rubra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20741	Artemisia hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19207	Anthenea chinensis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
AC50	1
EC50	3
ED50	1
Others	1
Potency	1

Activity Type	# Activity
Individual Protein	3
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	EC50	=	3475.0	nM	PMID[553598]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	EC50	=	74.0	nM	PMID[553598]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	EC50	=	506.0	nM	PMID[553598]
NPT2	Others	Unspecified		Potency	n.a.	60537.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Ac50	n.a.	1.122	uM	PMID[553599]
NPT2	Others	Unspecified		AC50	n.a.	1122.0	nM	PMID[553599]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.4	mg.kg-1	PMID[553600]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC106937 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	516
0.1-0.2	6817
0.2-0.3	11027
0.3-0.4	15906
0.4-0.5	3930
0.5-0.6	2359
0.6-0.7	1669
0.7-0.8	433
0.8-0.85	32
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8933	High Similarity	NPC46580
0.8696	High Similarity	NPC242209
0.8696	High Similarity	NPC13880
0.8667	High Similarity	NPC171171
0.8611	High Similarity	NPC314002
0.8588	High Similarity	NPC96890
0.8556	High Similarity	NPC204717
0.85	High Similarity	NPC220765
0.8387	Intermediate Similarity	NPC307963
0.8378	Intermediate Similarity	NPC92111
0.8333	Intermediate Similarity	NPC42979
0.8333	Intermediate Similarity	NPC99666
0.8324	Intermediate Similarity	NPC224764
0.8324	Intermediate Similarity	NPC76748
0.8316	Intermediate Similarity	NPC121772
0.8315	Intermediate Similarity	NPC474409
0.8278	Intermediate Similarity	NPC184964
0.8276	Intermediate Similarity	NPC131718
0.827	Intermediate Similarity	NPC296527
0.8254	Intermediate Similarity	NPC156704
0.8245	Intermediate Similarity	NPC326634
0.8232	Intermediate Similarity	NPC72980
0.8201	Intermediate Similarity	NPC251090
0.81	Intermediate Similarity	NPC170114
0.8083	Intermediate Similarity	NPC232727
0.8079	Intermediate Similarity	NPC102423
0.8075	Intermediate Similarity	NPC32771
0.8063	Intermediate Similarity	NPC77555
0.8051	Intermediate Similarity	NPC285558
0.805	Intermediate Similarity	NPC470549
0.804	Intermediate Similarity	NPC316981
0.804	Intermediate Similarity	NPC128084
0.803	Intermediate Similarity	NPC11464
0.8011	Intermediate Similarity	NPC230869
0.8011	Intermediate Similarity	NPC313791
0.8011	Intermediate Similarity	NPC94943
0.8	Intermediate Similarity	NPC212535
0.7959	Intermediate Similarity	NPC475070
0.7957	Intermediate Similarity	NPC190007
0.7957	Intermediate Similarity	NPC84478
0.7938	Intermediate Similarity	NPC213308
0.7938	Intermediate Similarity	NPC315491
0.7938	Intermediate Similarity	NPC45459
0.7902	Intermediate Similarity	NPC310118
0.7889	Intermediate Similarity	NPC80596
0.7889	Intermediate Similarity	NPC160105
0.7886	Intermediate Similarity	NPC469786
0.7886	Intermediate Similarity	NPC25008
0.7886	Intermediate Similarity	NPC469763
0.7886	Intermediate Similarity	NPC259644
0.7886	Intermediate Similarity	NPC73952
0.7886	Intermediate Similarity	NPC469765
0.7886	Intermediate Similarity	NPC469760
0.7877	Intermediate Similarity	NPC311276
0.7853	Intermediate Similarity	NPC324149
0.7846	Intermediate Similarity	NPC176538
0.7841	Intermediate Similarity	NPC75540
0.7841	Intermediate Similarity	NPC212376
0.7841	Intermediate Similarity	NPC80597
0.7841	Intermediate Similarity	NPC70922
0.7841	Intermediate Similarity	NPC211572
0.7821	Intermediate Similarity	NPC282231
0.7817	Intermediate Similarity	NPC200836
0.7814	Intermediate Similarity	NPC314603
0.7799	Intermediate Similarity	NPC110151
0.779	Intermediate Similarity	NPC474561
0.779	Intermediate Similarity	NPC49954
0.7789	Intermediate Similarity	NPC183777
0.7789	Intermediate Similarity	NPC88008
0.7784	Intermediate Similarity	NPC153042
0.7771	Intermediate Similarity	NPC105818
0.7771	Intermediate Similarity	NPC24678
0.7765	Intermediate Similarity	NPC279918
0.7761	Intermediate Similarity	NPC167860
0.7761	Intermediate Similarity	NPC123976
0.7761	Intermediate Similarity	NPC5145
0.7756	Intermediate Similarity	NPC264285
0.7755	Intermediate Similarity	NPC19872
0.7753	Intermediate Similarity	NPC469762
0.7746	Intermediate Similarity	NPC314372
0.7746	Intermediate Similarity	NPC159856
0.7734	Intermediate Similarity	NPC266931
0.7733	Intermediate Similarity	NPC190296
0.7718	Intermediate Similarity	NPC213530
0.7718	Intermediate Similarity	NPC193267
0.7713	Intermediate Similarity	NPC176127
0.7704	Intermediate Similarity	NPC476167
0.7697	Intermediate Similarity	NPC469785
0.7692	Intermediate Similarity	NPC243834
0.7692	Intermediate Similarity	NPC70956
0.7692	Intermediate Similarity	NPC16352
0.768	Intermediate Similarity	NPC131017
0.7665	Intermediate Similarity	NPC329747
0.7665	Intermediate Similarity	NPC249040
0.7665	Intermediate Similarity	NPC315957
0.7662	Intermediate Similarity	NPC476465
0.7661	Intermediate Similarity	NPC73767
0.7653	Intermediate Similarity	NPC192315
0.7653	Intermediate Similarity	NPC306376
0.765	Intermediate Similarity	NPC63751
0.7647	Intermediate Similarity	NPC88363
0.7644	Intermediate Similarity	NPC60621
0.7641	Intermediate Similarity	NPC222018
0.7635	Intermediate Similarity	NPC246518
0.7632	Intermediate Similarity	NPC188387
0.7632	Intermediate Similarity	NPC163421
0.7624	Intermediate Similarity	NPC174672
0.7619	Intermediate Similarity	NPC469358
0.7604	Intermediate Similarity	NPC128751
0.7604	Intermediate Similarity	NPC246700
0.7596	Intermediate Similarity	NPC54988
0.7594	Intermediate Similarity	NPC111275
0.7582	Intermediate Similarity	NPC194640
0.7582	Intermediate Similarity	NPC40779
0.7574	Intermediate Similarity	NPC475910
0.7573	Intermediate Similarity	NPC142901
0.7573	Intermediate Similarity	NPC148183
0.7573	Intermediate Similarity	NPC152768
0.7566	Intermediate Similarity	NPC71037
0.7565	Intermediate Similarity	NPC106833
0.7565	Intermediate Similarity	NPC95783
0.7565	Intermediate Similarity	NPC469497
0.7563	Intermediate Similarity	NPC72211
0.7561	Intermediate Similarity	NPC477610
0.7558	Intermediate Similarity	NPC110126
0.7551	Intermediate Similarity	NPC70259
0.755	Intermediate Similarity	NPC53144
0.7549	Intermediate Similarity	NPC208284
0.7544	Intermediate Similarity	NPC84911
0.7541	Intermediate Similarity	NPC471178
0.7536	Intermediate Similarity	NPC476041
0.7536	Intermediate Similarity	NPC304926
0.7514	Intermediate Similarity	NPC469780
0.7514	Intermediate Similarity	NPC469768
0.7514	Intermediate Similarity	NPC469767
0.7514	Intermediate Similarity	NPC469783
0.7514	Intermediate Similarity	NPC469784
0.7514	Intermediate Similarity	NPC469761
0.7514	Intermediate Similarity	NPC469779
0.7512	Intermediate Similarity	NPC470500
0.7512	Intermediate Similarity	NPC219087
0.75	Intermediate Similarity	NPC24370
0.75	Intermediate Similarity	NPC205934
0.75	Intermediate Similarity	NPC43787
0.75	Intermediate Similarity	NPC141353
0.75	Intermediate Similarity	NPC248454
0.75	Intermediate Similarity	NPC477609
0.75	Intermediate Similarity	NPC14113
0.75	Intermediate Similarity	NPC84827
0.75	Intermediate Similarity	NPC475112
0.75	Intermediate Similarity	NPC475085
0.75	Intermediate Similarity	NPC145885
0.75	Intermediate Similarity	NPC291535
0.75	Intermediate Similarity	NPC276517
0.75	Intermediate Similarity	NPC319232
0.7488	Intermediate Similarity	NPC171787
0.7488	Intermediate Similarity	NPC183407
0.7485	Intermediate Similarity	NPC96102
0.7485	Intermediate Similarity	NPC29886
0.7485	Intermediate Similarity	NPC261195
0.7476	Intermediate Similarity	NPC469592
0.7476	Intermediate Similarity	NPC471080
0.7474	Intermediate Similarity	NPC233936
0.7471	Intermediate Similarity	NPC469766
0.7463	Intermediate Similarity	NPC245816
0.7463	Intermediate Similarity	NPC476138
0.7463	Intermediate Similarity	NPC162484
0.7459	Intermediate Similarity	NPC78020
0.7458	Intermediate Similarity	NPC471957
0.7451	Intermediate Similarity	NPC185782
0.7448	Intermediate Similarity	NPC15102
0.7447	Intermediate Similarity	NPC267885
0.7443	Intermediate Similarity	NPC477861
0.7442	Intermediate Similarity	NPC105127
0.7438	Intermediate Similarity	NPC193777
0.7435	Intermediate Similarity	NPC48938
0.7427	Intermediate Similarity	NPC26679
0.7419	Intermediate Similarity	NPC256828
0.7418	Intermediate Similarity	NPC92796
0.7418	Intermediate Similarity	NPC135141
0.7416	Intermediate Similarity	NPC469594
0.7409	Intermediate Similarity	NPC315555
0.7409	Intermediate Similarity	NPC235684
0.7407	Intermediate Similarity	NPC59269
0.7406	Intermediate Similarity	NPC122436
0.74	Intermediate Similarity	NPC329793
0.74	Intermediate Similarity	NPC470497
0.7396	Intermediate Similarity	NPC284678
0.7395	Intermediate Similarity	NPC326363
0.7394	Intermediate Similarity	NPC110500
0.7394	Intermediate Similarity	NPC149155
0.7394	Intermediate Similarity	NPC203468
0.7393	Intermediate Similarity	NPC473317
0.7391	Intermediate Similarity	NPC476118
0.7389	Intermediate Similarity	NPC200214
0.7387	Intermediate Similarity	NPC470499
0.7381	Intermediate Similarity	NPC74360
0.738	Intermediate Similarity	NPC470498
0.7376	Intermediate Similarity	NPC476098
0.7371	Intermediate Similarity	NPC278434

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC106937 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	751
0.2-0.3	799
0.3-0.4	1486
0.4-0.5	2826
0.5-0.6	2105
0.6-0.7	833
0.7-0.8	96
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD802	Phase 2
0.8387	Intermediate Similarity	NPD1038	Approved
0.8342	Intermediate Similarity	NPD1392	Approved
0.8289	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7948	Phase 1
0.7979	Intermediate Similarity	NPD1768	Approved
0.7938	Intermediate Similarity	NPD484	Approved
0.7919	Intermediate Similarity	NPD3003	Approved
0.7869	Intermediate Similarity	NPD5065	Approved
0.7802	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4795	Phase 2
0.7723	Intermediate Similarity	NPD5066	Phase 2
0.7723	Intermediate Similarity	NPD5067	Phase 2
0.77	Intermediate Similarity	NPD7558	Phase 2
0.7696	Intermediate Similarity	NPD5902	Approved
0.7696	Intermediate Similarity	NPD5903	Approved
0.7665	Intermediate Similarity	NPD1740	Approved
0.7665	Intermediate Similarity	NPD1739	Approved
0.7662	Intermediate Similarity	NPD2187	Approved
0.7662	Intermediate Similarity	NPD2189	Approved
0.765	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3825	Phase 3
0.7612	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1326	Approved
0.7609	Intermediate Similarity	NPD1325	Approved
0.7585	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5658	Approved
0.7573	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5612	Discontinued
0.7561	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD786	Approved
0.7539	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD2092	Phase 2
0.7435	Intermediate Similarity	NPD2094	Phase 2
0.7435	Intermediate Similarity	NPD2095	Phase 2
0.7429	Intermediate Similarity	NPD6242	Discontinued
0.7421	Intermediate Similarity	NPD6595	Phase 3
0.7407	Intermediate Similarity	NPD2144	Approved
0.7402	Intermediate Similarity	NPD2916	Discontinued
0.7396	Intermediate Similarity	NPD2096	Phase 2
0.7396	Intermediate Similarity	NPD2091	Phase 2
0.7394	Intermediate Similarity	NPD482	Approved
0.7391	Intermediate Similarity	NPD5140	Approved
0.7391	Intermediate Similarity	NPD5138	Approved
0.7371	Intermediate Similarity	NPD1722	Approved
0.7366	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3330	Phase 1
0.7336	Intermediate Similarity	NPD7603	Discontinued
0.7333	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6985	Discontinued
0.7327	Intermediate Similarity	NPD6975	Discontinued
0.7327	Intermediate Similarity	NPD3928	Approved
0.7327	Intermediate Similarity	NPD3931	Approved
0.7323	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD3100	Discontinued
0.7299	Intermediate Similarity	NPD7194	Discontinued
0.7292	Intermediate Similarity	NPD3038	Discontinued
0.7285	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD9705	Discontinued
0.7283	Intermediate Similarity	NPD112	Approved
0.7282	Intermediate Similarity	NPD8431	Approved
0.7277	Intermediate Similarity	NPD4079	Approved
0.7277	Intermediate Similarity	NPD4076	Approved
0.7277	Intermediate Similarity	NPD4511	Phase 1
0.7268	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD3814	Phase 1
0.7255	Intermediate Similarity	NPD5901	Discontinued
0.7251	Intermediate Similarity	NPD5632	Approved
0.7249	Intermediate Similarity	NPD750	Phase 2
0.7225	Intermediate Similarity	NPD3506	Approved
0.7225	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3505	Approved
0.7222	Intermediate Similarity	NPD3404	Approved
0.7198	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2383	Phase 1
0.7189	Intermediate Similarity	NPD1404	Approved
0.7189	Intermediate Similarity	NPD1403	Approved
0.7182	Intermediate Similarity	NPD4462	Approved
0.7182	Intermediate Similarity	NPD2172	Phase 1
0.7182	Intermediate Similarity	NPD4463	Approved
0.7181	Intermediate Similarity	NPD2781	Approved
0.7178	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3816	Phase 1
0.7177	Intermediate Similarity	NPD3815	Phase 1
0.7175	Intermediate Similarity	NPD1592	Phase 3
0.7167	Intermediate Similarity	NPD4703	Approved
0.7167	Intermediate Similarity	NPD4702	Approved
0.7166	Intermediate Similarity	NPD2782	Approved
0.7166	Intermediate Similarity	NPD2780	Approved
0.7165	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8512	Phase 3
0.715	Intermediate Similarity	NPD2509	Approved
0.715	Intermediate Similarity	NPD4418	Discontinued
0.715	Intermediate Similarity	NPD2510	Approved
0.7136	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7470	Discontinued
0.7127	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5559	Phase 2
0.7105	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5482	Discontinued
0.7087	Intermediate Similarity	NPD3397	Phase 2
0.7085	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5100	Phase 3
0.7079	Intermediate Similarity	NPD2952	Discontinued
0.7077	Intermediate Similarity	NPD5596	Phase 2
0.7074	Intermediate Similarity	NPD926	Approved
0.7074	Intermediate Similarity	NPD925	Approved
0.705	Intermediate Similarity	NPD3924	Approved
0.705	Intermediate Similarity	NPD3922	Approved
0.705	Intermediate Similarity	NPD3923	Approved
0.705	Intermediate Similarity	NPD3921	Approved
0.7047	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5255	Approved
0.7037	Intermediate Similarity	NPD2639	Approved
0.7037	Intermediate Similarity	NPD2642	Approved
0.7026	Intermediate Similarity	NPD4203	Approved
0.7026	Intermediate Similarity	NPD4204	Approved
0.7021	Intermediate Similarity	NPD8129	Discovery
0.702	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8093	Discontinued
0.7011	Intermediate Similarity	NPD2837	Discontinued
0.701	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8396	Approved
0.701	Intermediate Similarity	NPD2177	Approved
0.701	Intermediate Similarity	NPD2176	Approved
0.701	Intermediate Similarity	NPD2175	Phase 3
0.701	Intermediate Similarity	NPD8395	Approved
0.701	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5426	Phase 3
0.7	Intermediate Similarity	NPD5913	Phase 3
0.7	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2640	Approved
0.7	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2641	Approved
0.7	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7112	Discontinued
0.6995	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8073	Approved
0.6986	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2616	Phase 3
0.6981	Remote Similarity	NPD8094	Discontinued
0.6981	Remote Similarity	NPD2615	Phase 3
0.698	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3402	Phase 1
0.6974	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3570	Phase 2
0.6962	Remote Similarity	NPD8284	Discontinued
0.6947	Remote Similarity	NPD424	Approved
0.6947	Remote Similarity	NPD425	Approved
0.6943	Remote Similarity	NPD4128	Approved
0.6943	Remote Similarity	NPD9690	Approved
0.6931	Remote Similarity	NPD3323	Discontinued
0.6923	Remote Similarity	NPD4037	Approved
0.6923	Remote Similarity	NPD31	Approved
0.6923	Remote Similarity	NPD4034	Approved
0.6923	Remote Similarity	NPD32	Approved
0.6923	Remote Similarity	NPD4122	Approved
0.6923	Remote Similarity	NPD4039	Approved
0.6923	Remote Similarity	NPD4036	Approved
0.6923	Remote Similarity	NPD4038	Approved
0.6923	Remote Similarity	NPD8272	Phase 2
0.6923	Remote Similarity	NPD4035	Approved
0.6923	Remote Similarity	NPD4033	Approved
0.6919	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD2844	Phase 3
0.6907	Remote Similarity	NPD4075	Phase 2
0.6906	Remote Similarity	NPD6494	Phase 2
0.6898	Remote Similarity	NPD2581	Approved
0.6898	Remote Similarity	NPD2582	Approved
0.6897	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8403	Phase 1
0.689	Remote Similarity	NPD7957	Phase 1
0.689	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7067	Approved
0.6886	Remote Similarity	NPD7068	Approved
0.6884	Remote Similarity	NPD5256	Discontinued
0.6884	Remote Similarity	NPD706	Phase 1
0.6881	Remote Similarity	NPD6569	Phase 2
0.6878	Remote Similarity	NPD7555	Discontinued
0.6875	Remote Similarity	NPD8072	Approved
0.6872	Remote Similarity	NPD4071	Approved
0.6872	Remote Similarity	NPD4181	Approved
0.6872	Remote Similarity	NPD4072	Approved
0.6872	Remote Similarity	NPD6159	Phase 2
0.6866	Remote Similarity	NPD5117	Phase 2
0.6866	Remote Similarity	NPD6281	Approved
0.6866	Remote Similarity	NPD5930	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data