NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.13
Volume:	219.233
LogP:	1.827
LogD:	1.533
LogS:	-1.416
# Rotatable Bonds:	4
TPSA:	37.05
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.798
Synthetic Accessibility Score:	1.975
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.756
MDCK Permeability:	7.6244136835157406e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.488
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.839
Plasma Protein Binding (PPB):	30.184280395507812%
Volume Distribution (VD):	3.084
Pgp-substrate:	59.134708404541016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.603
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.739
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.866
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	8.037
Half-life (T1/2):	0.709

ADMET: Toxicity

hERG Blockers:	0.346
Human Hepatotoxicity (H-HT):	0.817
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.146
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.918
Carcinogencity:	0.031
Eye Corrosion:	0.009
Eye Irritation:	0.048
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC76748

Natural Product ID:	NPC76748
*Common Name:**	5-Methoxy-N-Methyltryptamine
IUPAC Name:	2-(5-methoxy-1H-indol-3-yl)-N-methylethanamine
Synonyms:
Standard InCHIKey:	NFDDCRIHMZGWBP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3
SMILES:	CNCCc1c[nH]c2c1cc(OC)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL58579
PubChem CID:	16184
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
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	calyx	n.a.	PMID[21561086]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24086493]
NPO17294	Desmodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17294	Desmodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17294	Desmodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17294	Desmodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	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
IC50	1
Ki	3
Others	2

Activity Type	# Activity
Individual Protein	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT438	Individual Protein	Serotonin 2c (5-HT2c) receptor	Rattus norvegicus	Ki	=	840.0	nM	PMID[543722]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Ki	=	450.0	nM	PMID[543722]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Ki	=	4.1	nM	PMID[543722]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Ratio	=	205.0	n.a.	PMID[543722]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	12500.0	nM	PMID[543723]
NPT2	Others	Unspecified		Ratio	=	110.0	n.a.	PMID[543722]

☑ 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 NPC76748 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	610
0.1-0.2	5751
0.2-0.3	11541
0.3-0.4	12082
0.4-0.5	7471
0.5-0.6	2851
0.6-0.7	1704
0.7-0.8	604
0.8-0.85	52
0.85-0.9	18
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9941	High Similarity	NPC92111
0.994	High Similarity	NPC296527
0.9825	High Similarity	NPC307963
0.9486	High Similarity	NPC251090
0.9274	High Similarity	NPC176538
0.9186	High Similarity	NPC176127
0.9138	High Similarity	NPC171171
0.9133	High Similarity	NPC204717
0.913	High Similarity	NPC476465
0.908	High Similarity	NPC314002
0.9075	High Similarity	NPC220765
0.905	High Similarity	NPC13880
0.8889	High Similarity	NPC266931
0.8883	High Similarity	NPC208284
0.8844	High Similarity	NPC184964
0.8836	High Similarity	NPC316981
0.8778	High Similarity	NPC99666
0.8703	High Similarity	NPC232727
0.8663	High Similarity	NPC285558
0.8649	High Similarity	NPC329793
0.8649	High Similarity	NPC315957
0.8649	High Similarity	NPC121772
0.861	High Similarity	NPC476138
0.861	High Similarity	NPC245816
0.8596	High Similarity	NPC84478
0.8587	High Similarity	NPC156704
0.8548	High Similarity	NPC19872
0.8486	Intermediate Similarity	NPC77555
0.8454	Intermediate Similarity	NPC470549
0.8453	Intermediate Similarity	NPC46580
0.841	Intermediate Similarity	NPC170114
0.8407	Intermediate Similarity	NPC32771
0.8378	Intermediate Similarity	NPC131017
0.8351	Intermediate Similarity	NPC315491
0.8351	Intermediate Similarity	NPC45459
0.8342	Intermediate Similarity	NPC167860
0.8342	Intermediate Similarity	NPC123976
0.8324	Intermediate Similarity	NPC106937
0.829	Intermediate Similarity	NPC185782
0.8272	Intermediate Similarity	NPC475070
0.8256	Intermediate Similarity	NPC26679
0.8254	Intermediate Similarity	NPC213308
0.8247	Intermediate Similarity	NPC11464
0.8247	Intermediate Similarity	NPC471304
0.8238	Intermediate Similarity	NPC82548
0.822	Intermediate Similarity	NPC475774
0.822	Intermediate Similarity	NPC223427
0.8208	Intermediate Similarity	NPC131718
0.8207	Intermediate Similarity	NPC242928
0.8182	Intermediate Similarity	NPC326634
0.8158	Intermediate Similarity	NPC329747
0.8138	Intermediate Similarity	NPC222018
0.8125	Intermediate Similarity	NPC162484
0.8122	Intermediate Similarity	NPC476287
0.8114	Intermediate Similarity	NPC102423
0.8111	Intermediate Similarity	NPC96890
0.8109	Intermediate Similarity	NPC310118
0.81	Intermediate Similarity	NPC193267
0.81	Intermediate Similarity	NPC213530
0.81	Intermediate Similarity	NPC74360
0.8093	Intermediate Similarity	NPC88008
0.8077	Intermediate Similarity	NPC474798
0.8073	Intermediate Similarity	NPC135887
0.8073	Intermediate Similarity	NPC199277
0.8071	Intermediate Similarity	NPC94157
0.8066	Intermediate Similarity	NPC88363
0.8063	Intermediate Similarity	NPC234197
0.8061	Intermediate Similarity	NPC5145
0.8056	Intermediate Similarity	NPC224764
0.8046	Intermediate Similarity	NPC230869
0.8045	Intermediate Similarity	NPC313791
0.8042	Intermediate Similarity	NPC242209
0.804	Intermediate Similarity	NPC470799
0.804	Intermediate Similarity	NPC8022
0.803	Intermediate Similarity	NPC478074
0.802	Intermediate Similarity	NPC60621
0.8011	Intermediate Similarity	NPC311276
0.801	Intermediate Similarity	NPC287437
0.8	Intermediate Similarity	NPC193777
0.8	Intermediate Similarity	NPC267928
0.799	Intermediate Similarity	NPC295228
0.799	Intermediate Similarity	NPC274291
0.799	Intermediate Similarity	NPC118832
0.799	Intermediate Similarity	NPC264166
0.799	Intermediate Similarity	NPC47059
0.799	Intermediate Similarity	NPC165349
0.799	Intermediate Similarity	NPC329708
0.7989	Intermediate Similarity	NPC284678
0.7979	Intermediate Similarity	NPC195268
0.7979	Intermediate Similarity	NPC133140
0.7967	Intermediate Similarity	NPC42979
0.796	Intermediate Similarity	NPC96321
0.7959	Intermediate Similarity	NPC171787
0.7949	Intermediate Similarity	NPC300156
0.7949	Intermediate Similarity	NPC45190
0.794	Intermediate Similarity	NPC477610
0.7937	Intermediate Similarity	NPC84853
0.7933	Intermediate Similarity	NPC469554
0.7921	Intermediate Similarity	NPC292958
0.7919	Intermediate Similarity	NPC469760
0.7919	Intermediate Similarity	NPC469786
0.7919	Intermediate Similarity	NPC469763
0.7919	Intermediate Similarity	NPC259644
0.7919	Intermediate Similarity	NPC26872
0.7919	Intermediate Similarity	NPC73952
0.7919	Intermediate Similarity	NPC469765
0.7919	Intermediate Similarity	NPC25008
0.7917	Intermediate Similarity	NPC476167
0.7917	Intermediate Similarity	NPC128823
0.7913	Intermediate Similarity	NPC110151
0.7906	Intermediate Similarity	NPC70956
0.7906	Intermediate Similarity	NPC243834
0.7892	Intermediate Similarity	NPC280272
0.7889	Intermediate Similarity	NPC219087
0.7884	Intermediate Similarity	NPC324149
0.7876	Intermediate Similarity	NPC249040
0.7874	Intermediate Similarity	NPC75540
0.7874	Intermediate Similarity	NPC212376
0.7874	Intermediate Similarity	NPC70922
0.7874	Intermediate Similarity	NPC211572
0.7874	Intermediate Similarity	NPC80597
0.7869	Intermediate Similarity	NPC72980
0.7868	Intermediate Similarity	NPC475910
0.7865	Intermediate Similarity	NPC192315
0.7865	Intermediate Similarity	NPC72211
0.7857	Intermediate Similarity	NPC472111
0.7854	Intermediate Similarity	NPC122436
0.7853	Intermediate Similarity	NPC177404
0.7853	Intermediate Similarity	NPC70259
0.7853	Intermediate Similarity	NPC282231
0.7847	Intermediate Similarity	NPC101543
0.7829	Intermediate Similarity	NPC469785
0.7828	Intermediate Similarity	NPC201697
0.7824	Intermediate Similarity	NPC476582
0.7824	Intermediate Similarity	NPC4071
0.7824	Intermediate Similarity	NPC476578
0.7822	Intermediate Similarity	NPC476041
0.7822	Intermediate Similarity	NPC304926
0.7821	Intermediate Similarity	NPC160105
0.7821	Intermediate Similarity	NPC49954
0.7821	Intermediate Similarity	NPC474561
0.7819	Intermediate Similarity	NPC246700
0.7819	Intermediate Similarity	NPC128751
0.781	Intermediate Similarity	NPC180504
0.7803	Intermediate Similarity	NPC24678
0.7803	Intermediate Similarity	NPC105818
0.7801	Intermediate Similarity	NPC205934
0.7801	Intermediate Similarity	NPC43787
0.7797	Intermediate Similarity	NPC279918
0.7794	Intermediate Similarity	NPC472099
0.7794	Intermediate Similarity	NPC132642
0.7788	Intermediate Similarity	NPC314954
0.7784	Intermediate Similarity	NPC477019
0.7784	Intermediate Similarity	NPC469762
0.7783	Intermediate Similarity	NPC477609
0.7778	Intermediate Similarity	NPC106833
0.7778	Intermediate Similarity	NPC469497
0.7778	Intermediate Similarity	NPC314372
0.7778	Intermediate Similarity	NPC153467
0.7778	Intermediate Similarity	NPC159856
0.7766	Intermediate Similarity	NPC323345
0.7766	Intermediate Similarity	NPC470164
0.7765	Intermediate Similarity	NPC190296
0.7761	Intermediate Similarity	NPC162530
0.7761	Intermediate Similarity	NPC469592
0.7761	Intermediate Similarity	NPC471080
0.7754	Intermediate Similarity	NPC163421
0.7754	Intermediate Similarity	NPC188387
0.7746	Intermediate Similarity	NPC11408
0.7739	Intermediate Similarity	NPC174672
0.7739	Intermediate Similarity	NPC174758
0.7737	Intermediate Similarity	NPC138370
0.7727	Intermediate Similarity	NPC321428
0.7727	Intermediate Similarity	NPC313189
0.7727	Intermediate Similarity	NPC193238
0.7722	Intermediate Similarity	NPC54988
0.7716	Intermediate Similarity	NPC16452
0.7716	Intermediate Similarity	NPC36229
0.7716	Intermediate Similarity	NPC476581
0.7711	Intermediate Similarity	NPC48353
0.7709	Intermediate Similarity	NPC118511
0.7708	Intermediate Similarity	NPC276517
0.77	Intermediate Similarity	NPC15801
0.7692	Intermediate Similarity	NPC73767
0.7685	Intermediate Similarity	NPC288349
0.7684	Intermediate Similarity	NPC26850
0.768	Intermediate Similarity	NPC63751
0.7679	Intermediate Similarity	NPC84911
0.7674	Intermediate Similarity	NPC217554
0.7668	Intermediate Similarity	NPC194967
0.7665	Intermediate Similarity	NPC476098
0.7656	Intermediate Similarity	NPC478078
0.7653	Intermediate Similarity	NPC267423
0.765	Intermediate Similarity	NPC474409
0.765	Intermediate Similarity	NPC314603
0.765	Intermediate Similarity	NPC473181
0.765	Intermediate Similarity	NPC476116
0.7647	Intermediate Similarity	NPC469767
0.7647	Intermediate Similarity	NPC469779
0.7647	Intermediate Similarity	NPC469783

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 NPC76748 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	722
0.2-0.3	768
0.3-0.4	1349
0.4-0.5	2502
0.5-0.6	2255
0.6-0.7	979
0.7-0.8	215
0.8-0.85	18
0.85-0.9	9
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9825	High Similarity	NPD1304	Clinical (unspecified phase)
0.9825	High Similarity	NPD1038	Approved
0.913	High Similarity	NPD2189	Approved
0.913	High Similarity	NPD2187	Approved
0.8901	High Similarity	NPD3825	Phase 3
0.8789	High Similarity	NPD1322	Clinical (unspecified phase)
0.8729	High Similarity	NPD5575	Clinical (unspecified phase)
0.8698	High Similarity	NPD5612	Discontinued
0.8696	High Similarity	NPD4118	Clinical (unspecified phase)
0.8681	High Similarity	NPD3324	Clinical (unspecified phase)
0.8663	High Similarity	NPD4795	Phase 2
0.8649	High Similarity	NPD1740	Approved
0.8649	High Similarity	NPD1739	Approved
0.8615	High Similarity	NPD6242	Discontinued
0.8474	Intermediate Similarity	NPD1392	Approved
0.8351	Intermediate Similarity	NPD484	Approved
0.8333	Intermediate Similarity	NPD5658	Approved
0.8324	Intermediate Similarity	NPD802	Phase 2
0.8227	Intermediate Similarity	NPD5559	Phase 2
0.8205	Intermediate Similarity	NPD5067	Phase 2
0.8205	Intermediate Similarity	NPD5066	Phase 2
0.8105	Intermediate Similarity	NPD1768	Approved
0.8095	Intermediate Similarity	NPD7948	Phase 1
0.8085	Intermediate Similarity	NPD4418	Discontinued
0.8041	Intermediate Similarity	NPD3003	Approved
0.8	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD4036	Approved
0.799	Intermediate Similarity	NPD4122	Approved
0.799	Intermediate Similarity	NPD4034	Approved
0.799	Intermediate Similarity	NPD32	Approved
0.799	Intermediate Similarity	NPD31	Approved
0.799	Intermediate Similarity	NPD4039	Approved
0.799	Intermediate Similarity	NPD4035	Approved
0.799	Intermediate Similarity	NPD4033	Approved
0.799	Intermediate Similarity	NPD4038	Approved
0.799	Intermediate Similarity	NPD4037	Approved
0.7979	Intermediate Similarity	NPD3924	Approved
0.7979	Intermediate Similarity	NPD3922	Approved
0.7979	Intermediate Similarity	NPD3921	Approved
0.7979	Intermediate Similarity	NPD3923	Approved
0.7889	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3354	Phase 2
0.7861	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7839	Intermediate Similarity	NPD949	Phase 1
0.7833	Intermediate Similarity	NPD3402	Phase 1
0.7817	Intermediate Similarity	NPD7222	Phase 2
0.7817	Intermediate Similarity	NPD7453	Approved
0.7817	Intermediate Similarity	NPD7452	Approved
0.7802	Intermediate Similarity	NPD5065	Approved
0.7795	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD565	Phase 2
0.7731	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7558	Phase 2
0.7723	Intermediate Similarity	NPD5902	Approved
0.7723	Intermediate Similarity	NPD5903	Approved
0.772	Intermediate Similarity	NPD2952	Discontinued
0.7717	Intermediate Similarity	NPD4071	Approved
0.7717	Intermediate Similarity	NPD4072	Approved
0.7716	Intermediate Similarity	NPD3397	Phase 2
0.7697	Intermediate Similarity	NPD112	Approved
0.7697	Intermediate Similarity	NPD9705	Discontinued
0.7692	Intermediate Similarity	NPD786	Approved
0.7668	Intermediate Similarity	NPD3477	Phase 2
0.7668	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD4548	Discontinued
0.7637	Intermediate Similarity	NPD1326	Approved
0.7637	Intermediate Similarity	NPD1325	Approved
0.7624	Intermediate Similarity	NPD3815	Phase 1
0.7624	Intermediate Similarity	NPD3816	Phase 1
0.7619	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5256	Discontinued
0.76	Intermediate Similarity	NPD5529	Phase 1
0.76	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4204	Approved
0.7594	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4203	Approved
0.7588	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD8403	Phase 1
0.7579	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD1034	Phase 3
0.7572	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4889	Approved
0.7552	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD5913	Phase 3
0.7551	Intermediate Similarity	NPD5999	Phase 2
0.7549	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4558	Phase 2
0.754	Intermediate Similarity	NPD6595	Phase 3
0.7527	Intermediate Similarity	NPD1032	Phase 2
0.7524	Intermediate Similarity	NPD4429	Discontinued
0.7513	Intermediate Similarity	NPD6569	Phase 2
0.7512	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1722	Approved
0.75	Intermediate Similarity	NPD3386	Phase 2
0.75	Intermediate Similarity	NPD8512	Phase 3
0.7488	Intermediate Similarity	NPD3006	Discontinued
0.7488	Intermediate Similarity	NPD4454	Phase 2
0.7487	Intermediate Similarity	NPD3920	Phase 2
0.7487	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6494	Phase 2
0.7475	Intermediate Similarity	NPD4511	Phase 1
0.7473	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD4343	Phase 1
0.7452	Intermediate Similarity	NPD5930	Phase 3
0.744	Intermediate Similarity	NPD5632	Approved
0.744	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD4921	Phase 3
0.7435	Intermediate Similarity	NPD4919	Phase 3
0.7433	Intermediate Similarity	NPD2144	Approved
0.7426	Intermediate Similarity	NPD2510	Approved
0.7426	Intermediate Similarity	NPD2509	Approved
0.7419	Intermediate Similarity	NPD482	Approved
0.7419	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5601	Phase 2
0.7405	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD4502	Phase 2
0.7402	Intermediate Similarity	NPD7470	Discontinued
0.74	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2581	Approved
0.7389	Intermediate Similarity	NPD2582	Approved
0.7385	Intermediate Similarity	NPD4551	Phase 2
0.7371	Intermediate Similarity	NPD7555	Discontinued
0.7368	Intermediate Similarity	NPD2095	Phase 2
0.7368	Intermediate Similarity	NPD2094	Phase 2
0.7368	Intermediate Similarity	NPD2092	Phase 2
0.7361	Intermediate Similarity	NPD6963	Approved
0.7361	Intermediate Similarity	NPD6964	Approved
0.736	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7051	Phase 3
0.7358	Intermediate Similarity	NPD4021	Phase 2
0.7358	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6985	Discontinued
0.7349	Intermediate Similarity	NPD4885	Approved
0.7347	Intermediate Similarity	NPD3395	Approved
0.7347	Intermediate Similarity	NPD3396	Approved
0.7347	Intermediate Similarity	NPD1951	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3100	Discontinued
0.7337	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD7567	Approved
0.7336	Intermediate Similarity	NPD6968	Phase 2
0.7336	Intermediate Similarity	NPD6969	Phase 2
0.733	Intermediate Similarity	NPD2096	Phase 2
0.733	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2091	Phase 2
0.7321	Intermediate Similarity	NPD7194	Discontinued
0.7316	Intermediate Similarity	NPD3038	Discontinued
0.7311	Intermediate Similarity	NPD3938	Phase 1
0.731	Intermediate Similarity	NPD2482	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1418	Phase 2
0.7303	Intermediate Similarity	NPD2172	Phase 1
0.7297	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD2334	Discontinued
0.7282	Intermediate Similarity	NPD3330	Phase 1
0.7277	Intermediate Similarity	NPD5482	Discontinued
0.7263	Intermediate Similarity	NPD2599	Approved
0.7263	Intermediate Similarity	NPD2601	Approved
0.7263	Intermediate Similarity	NPD2600	Approved
0.726	Intermediate Similarity	NPD7112	Discontinued
0.726	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6230	Discontinued
0.7249	Intermediate Similarity	NPD5670	Approved
0.7247	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5530	Phase 1
0.7238	Intermediate Similarity	NPD3763	Approved
0.7234	Intermediate Similarity	NPD9690	Approved
0.7233	Intermediate Similarity	NPD6220	Phase 3
0.723	Intermediate Similarity	NPD4890	Phase 2
0.723	Intermediate Similarity	NPD1258	Discontinued
0.722	Intermediate Similarity	NPD4437	Phase 3
0.7217	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8431	Approved
0.7214	Intermediate Similarity	NPD5259	Phase 3
0.7207	Intermediate Similarity	NPD3835	Phase 3
0.7207	Intermediate Similarity	NPD7067	Approved
0.7207	Intermediate Similarity	NPD3833	Phase 3
0.7207	Intermediate Similarity	NPD7068	Approved
0.7204	Intermediate Similarity	NPD6856	Discontinued
0.72	Intermediate Similarity	NPD2177	Approved
0.72	Intermediate Similarity	NPD3814	Phase 1
0.72	Intermediate Similarity	NPD2175	Phase 3
0.72	Intermediate Similarity	NPD2176	Approved
0.72	Intermediate Similarity	NPD6243	Phase 3
0.72	Intermediate Similarity	NPD1592	Phase 3
0.72	Intermediate Similarity	NPD6244	Phase 3
0.7198	Intermediate Similarity	NPD7069	Discontinued
0.7196	Intermediate Similarity	NPD7603	Discontinued
0.7189	Intermediate Similarity	NPD2782	Approved
0.7189	Intermediate Similarity	NPD2780	Approved

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