NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	198.08
Volume:	205.404
LogP:	1.774
LogD:	1.891
LogS:	-3.091
# Rotatable Bonds:	1
TPSA:	48.91
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	2.233
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.699
MDCK Permeability:	1.4246446880861185e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.84

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.855
Plasma Protein Binding (PPB):	69.4288558959961%
Volume Distribution (VD):	1.348
Pgp-substrate:	21.427675247192383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.846
CYP2C19-inhibitor:	0.296
CYP2C19-substrate:	0.207
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.58
CYP2D6-inhibitor:	0.353
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.316
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	6.393
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.83
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.358
Rat Oral Acute Toxicity:	0.805
Maximum Recommended Daily Dose:	0.387
Skin Sensitization:	0.627
Carcinogencity:	0.239
Eye Corrosion:	0.008
Eye Irritation:	0.95
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC48938

Natural Product ID:	NPC48938
*Common Name:**	1-Hydroxymethyl-Beta-Carboline
IUPAC Name:	9H-pyrido[3,4-b]indol-1-ylmethanol
Synonyms:
Standard InCHIKey:	XKCXIUDPGSNQIQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H10N2O/c15-7-11-12-9(5-6-13-11)8-3-1-2-4-10(8)14-12/h1-6,14-15H,7H2
SMILES:	c1ccc2c(c1)c1ccnc(CO)c1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3400674
PubChem CID:	5318284
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000023]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	17.0	%	PMID[549452]

☑ 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 NPC48938 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	594
0.1-0.2	4371
0.2-0.3	13808
0.3-0.4	16429
0.4-0.5	3384
0.5-0.6	1828
0.6-0.7	1600
0.7-0.8	618
0.8-0.85	47
0.85-0.9	14
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9345	High Similarity	NPC284678
0.8963	High Similarity	NPC102423
0.895	High Similarity	NPC470505
0.895	High Similarity	NPC470500
0.8889	High Similarity	NPC314394
0.8841	High Similarity	NPC131718
0.8722	High Similarity	NPC192315
0.871	High Similarity	NPC5145
0.8674	High Similarity	NPC476167
0.8652	High Similarity	NPC324149
0.8647	High Similarity	NPC313791
0.8533	High Similarity	NPC473761
0.8457	Intermediate Similarity	NPC63545
0.8443	Intermediate Similarity	NPC230869
0.8434	Intermediate Similarity	NPC141353
0.8434	Intermediate Similarity	NPC469785
0.8424	Intermediate Similarity	NPC19872
0.8412	Intermediate Similarity	NPC54988
0.8405	Intermediate Similarity	NPC201380
0.8405	Intermediate Similarity	NPC179787
0.8405	Intermediate Similarity	NPC469811
0.8383	Intermediate Similarity	NPC469762
0.8354	Intermediate Similarity	NPC321911
0.8315	Intermediate Similarity	NPC212213
0.8284	Intermediate Similarity	NPC279918
0.8282	Intermediate Similarity	NPC159856
0.8265	Intermediate Similarity	NPC470502
0.8245	Intermediate Similarity	NPC475070
0.8235	Intermediate Similarity	NPC282231
0.8223	Intermediate Similarity	NPC470501
0.822	Intermediate Similarity	NPC123839
0.8216	Intermediate Similarity	NPC265576
0.8211	Intermediate Similarity	NPC266249
0.8204	Intermediate Similarity	NPC259644
0.8204	Intermediate Similarity	NPC469786
0.8204	Intermediate Similarity	NPC469763
0.8204	Intermediate Similarity	NPC25008
0.8204	Intermediate Similarity	NPC73952
0.8204	Intermediate Similarity	NPC469765
0.8204	Intermediate Similarity	NPC325903
0.8204	Intermediate Similarity	NPC469760
0.8191	Intermediate Similarity	NPC245816
0.8191	Intermediate Similarity	NPC476138
0.8187	Intermediate Similarity	NPC311276
0.8182	Intermediate Similarity	NPC470503
0.8182	Intermediate Similarity	NPC232727
0.8167	Intermediate Similarity	NPC62749
0.8166	Intermediate Similarity	NPC236711
0.8161	Intermediate Similarity	NPC470498
0.8155	Intermediate Similarity	NPC70922
0.8155	Intermediate Similarity	NPC75540
0.8155	Intermediate Similarity	NPC212376
0.8155	Intermediate Similarity	NPC211572
0.8155	Intermediate Similarity	NPC80597
0.815	Intermediate Similarity	NPC201700
0.815	Intermediate Similarity	NPC63751
0.8128	Intermediate Similarity	NPC176538
0.8125	Intermediate Similarity	NPC150048
0.8125	Intermediate Similarity	NPC203754
0.8118	Intermediate Similarity	NPC239954
0.8118	Intermediate Similarity	NPC135141
0.8118	Intermediate Similarity	NPC92796
0.8111	Intermediate Similarity	NPC15102
0.8101	Intermediate Similarity	NPC220765
0.8098	Intermediate Similarity	NPC198673
0.8092	Intermediate Similarity	NPC49954
0.8092	Intermediate Similarity	NPC474561
0.8084	Intermediate Similarity	NPC24678
0.8084	Intermediate Similarity	NPC105818
0.8061	Intermediate Similarity	NPC314372
0.8056	Intermediate Similarity	NPC204717
0.8049	Intermediate Similarity	NPC190296
0.8046	Intermediate Similarity	NPC317430
0.8041	Intermediate Similarity	NPC118940
0.8033	Intermediate Similarity	NPC95783
0.8022	Intermediate Similarity	NPC46580
0.8011	Intermediate Similarity	NPC314002
0.801	Intermediate Similarity	NPC470799
0.801	Intermediate Similarity	NPC8022
0.8	Intermediate Similarity	NPC165599
0.7989	Intermediate Similarity	NPC24864
0.7989	Intermediate Similarity	NPC160105
0.7978	Intermediate Similarity	NPC59269
0.7978	Intermediate Similarity	NPC151939
0.7977	Intermediate Similarity	NPC40779
0.7967	Intermediate Similarity	NPC171171
0.7965	Intermediate Similarity	NPC470204
0.7965	Intermediate Similarity	NPC122141
0.7955	Intermediate Similarity	NPC158129
0.7947	Intermediate Similarity	NPC57398
0.7946	Intermediate Similarity	NPC99666
0.7944	Intermediate Similarity	NPC233936
0.7937	Intermediate Similarity	NPC470497
0.7926	Intermediate Similarity	NPC168911
0.7919	Intermediate Similarity	NPC470203
0.7917	Intermediate Similarity	NPC475288
0.791	Intermediate Similarity	NPC34508
0.791	Intermediate Similarity	NPC472123
0.791	Intermediate Similarity	NPC314603
0.7901	Intermediate Similarity	NPC163055
0.7889	Intermediate Similarity	NPC193267
0.7889	Intermediate Similarity	NPC213530
0.7887	Intermediate Similarity	NPC185782
0.7877	Intermediate Similarity	NPC184964
0.7876	Intermediate Similarity	NPC244741
0.7876	Intermediate Similarity	NPC473362
0.7876	Intermediate Similarity	NPC166492
0.7874	Intermediate Similarity	NPC317105
0.7874	Intermediate Similarity	NPC194640
0.7872	Intermediate Similarity	NPC141454
0.7872	Intermediate Similarity	NPC267928
0.7857	Intermediate Similarity	NPC26679
0.7857	Intermediate Similarity	NPC470111
0.7846	Intermediate Similarity	NPC123976
0.7846	Intermediate Similarity	NPC167860
0.7833	Intermediate Similarity	NPC215795
0.7833	Intermediate Similarity	NPC176199
0.7833	Intermediate Similarity	NPC42979
0.7831	Intermediate Similarity	NPC474916
0.7829	Intermediate Similarity	NPC274229
0.7822	Intermediate Similarity	NPC229893
0.7821	Intermediate Similarity	NPC224764
0.7818	Intermediate Similarity	NPC115611
0.7814	Intermediate Similarity	NPC188387
0.7814	Intermediate Similarity	NPC163421
0.7811	Intermediate Similarity	NPC288445
0.7802	Intermediate Similarity	NPC102755
0.7791	Intermediate Similarity	NPC96102
0.779	Intermediate Similarity	NPC300688
0.7789	Intermediate Similarity	NPC476041
0.7789	Intermediate Similarity	NPC304926
0.7784	Intermediate Similarity	NPC49217
0.7778	Intermediate Similarity	NPC96890
0.7778	Intermediate Similarity	NPC77555
0.7778	Intermediate Similarity	NPC68354
0.7778	Intermediate Similarity	NPC248454
0.7772	Intermediate Similarity	NPC94752
0.7771	Intermediate Similarity	NPC476118
0.7765	Intermediate Similarity	NPC149155
0.7765	Intermediate Similarity	NPC110500
0.7765	Intermediate Similarity	NPC37423
0.7765	Intermediate Similarity	NPC203468
0.7765	Intermediate Similarity	NPC275305
0.7751	Intermediate Similarity	NPC471957
0.7747	Intermediate Similarity	NPC71037
0.7744	Intermediate Similarity	NPC84911
0.7744	Intermediate Similarity	NPC105127
0.774	Intermediate Similarity	NPC78020
0.7737	Intermediate Similarity	NPC470499
0.7735	Intermediate Similarity	NPC283219
0.7735	Intermediate Similarity	NPC270009
0.7735	Intermediate Similarity	NPC126709
0.7735	Intermediate Similarity	NPC248041
0.7733	Intermediate Similarity	NPC470507
0.773	Intermediate Similarity	NPC278434
0.773	Intermediate Similarity	NPC317030
0.7727	Intermediate Similarity	NPC476287
0.7725	Intermediate Similarity	NPC242209
0.7725	Intermediate Similarity	NPC251090
0.7723	Intermediate Similarity	NPC60621
0.7723	Intermediate Similarity	NPC310118
0.7722	Intermediate Similarity	NPC267885
0.772	Intermediate Similarity	NPC53144
0.7714	Intermediate Similarity	NPC225018
0.7707	Intermediate Similarity	NPC110151
0.77	Intermediate Similarity	NPC27041
0.7697	Intermediate Similarity	NPC97343
0.7697	Intermediate Similarity	NPC314940
0.7697	Intermediate Similarity	NPC473764
0.7692	Intermediate Similarity	NPC288838
0.7683	Intermediate Similarity	NPC29886
0.7683	Intermediate Similarity	NPC261195
0.7676	Intermediate Similarity	NPC315555
0.7676	Intermediate Similarity	NPC474707
0.7672	Intermediate Similarity	NPC195314
0.7672	Intermediate Similarity	NPC133366
0.767	Intermediate Similarity	NPC478184
0.7668	Intermediate Similarity	NPC211813
0.7656	Intermediate Similarity	NPC249040
0.7656	Intermediate Similarity	NPC182222
0.7654	Intermediate Similarity	NPC82331
0.7654	Intermediate Similarity	NPC256893
0.7651	Intermediate Similarity	NPC73767
0.7651	Intermediate Similarity	NPC110126
0.765	Intermediate Similarity	NPC191415
0.765	Intermediate Similarity	NPC192270
0.7644	Intermediate Similarity	NPC473640
0.7638	Intermediate Similarity	NPC89508
0.7637	Intermediate Similarity	NPC72980
0.7635	Intermediate Similarity	NPC471506
0.7634	Intermediate Similarity	NPC204565
0.7629	Intermediate Similarity	NPC200836
0.7626	Intermediate Similarity	NPC82370
0.7624	Intermediate Similarity	NPC134586
0.7622	Intermediate Similarity	NPC198988
0.7621	Intermediate Similarity	NPC476492
0.7621	Intermediate Similarity	NPC6215
0.7619	Intermediate Similarity	NPC474177
0.7619	Intermediate Similarity	NPC307963
0.7616	Intermediate Similarity	NPC216713

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 NPC48938 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	677
0.2-0.3	785
0.3-0.4	1680
0.4-0.5	2593
0.5-0.6	1926
0.6-0.7	1019
0.7-0.8	170
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8706	High Similarity	NPD5065	Approved
0.8371	Intermediate Similarity	NPD706	Phase 1
0.8256	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD6595	Phase 3
0.7989	Intermediate Similarity	NPD424	Approved
0.7989	Intermediate Similarity	NPD425	Approved
0.7949	Intermediate Similarity	NPD3330	Phase 1
0.7912	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1326	Approved
0.7898	Intermediate Similarity	NPD1325	Approved
0.7879	Intermediate Similarity	NPD1722	Approved
0.7872	Intermediate Similarity	NPD7948	Phase 1
0.7849	Intermediate Similarity	NPD3404	Approved
0.7833	Intermediate Similarity	NPD4079	Approved
0.7833	Intermediate Similarity	NPD4076	Approved
0.7824	Intermediate Similarity	NPD2882	Phase 1
0.7821	Intermediate Similarity	NPD2382	Approved
0.7821	Intermediate Similarity	NPD2380	Approved
0.7821	Intermediate Similarity	NPD2381	Approved
0.7812	Intermediate Similarity	NPD4886	Phase 2
0.7803	Intermediate Similarity	NPD5255	Approved
0.7802	Intermediate Similarity	NPD5596	Phase 2
0.7802	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3506	Approved
0.7778	Intermediate Similarity	NPD3505	Approved
0.7771	Intermediate Similarity	NPD5138	Approved
0.7771	Intermediate Similarity	NPD5140	Approved
0.7765	Intermediate Similarity	NPD482	Approved
0.773	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD2144	Approved
0.7674	Intermediate Similarity	NPD2837	Discontinued
0.7667	Intermediate Similarity	NPD6492	Phase 2
0.7665	Intermediate Similarity	NPD1592	Phase 3
0.7653	Intermediate Similarity	NPD4612	Discontinued
0.7651	Intermediate Similarity	NPD786	Approved
0.7647	Intermediate Similarity	NPD4702	Approved
0.7647	Intermediate Similarity	NPD4703	Approved
0.7647	Intermediate Similarity	NPD3321	Discontinued
0.7644	Intermediate Similarity	NPD2581	Approved
0.7644	Intermediate Similarity	NPD2582	Approved
0.7629	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1038	Approved
0.7616	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6158	Phase 2
0.7609	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3813	Approved
0.7573	Intermediate Similarity	NPD7603	Discontinued
0.7569	Intermediate Similarity	NPD9690	Approved
0.7565	Intermediate Similarity	NPD484	Approved
0.7558	Intermediate Similarity	NPD4463	Approved
0.7558	Intermediate Similarity	NPD4462	Approved
0.7557	Intermediate Similarity	NPD112	Approved
0.7557	Intermediate Similarity	NPD9705	Discontinued
0.7554	Intermediate Similarity	NPD3038	Discontinued
0.7551	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD1661	Suspended
0.7543	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5862	Discovery
0.754	Intermediate Similarity	NPD8431	Approved
0.7538	Intermediate Similarity	NPD5067	Phase 2
0.7538	Intermediate Similarity	NPD7470	Discontinued
0.7538	Intermediate Similarity	NPD5066	Phase 2
0.7527	Intermediate Similarity	NPD5100	Phase 3
0.7527	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2095	Phase 2
0.7514	Intermediate Similarity	NPD2094	Phase 2
0.7514	Intermediate Similarity	NPD2092	Phase 2
0.75	Intermediate Similarity	NPD5901	Discontinued
0.75	Intermediate Similarity	NPD8093	Discontinued
0.75	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1274	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5612	Discontinued
0.7473	Intermediate Similarity	NPD2091	Phase 2
0.7473	Intermediate Similarity	NPD2096	Phase 2
0.746	Intermediate Similarity	NPD6281	Approved
0.7459	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7867	Phase 1
0.7448	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4638	Approved
0.7444	Intermediate Similarity	NPD4640	Approved
0.7444	Intermediate Similarity	NPD4639	Approved
0.7437	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD802	Phase 2
0.7433	Intermediate Similarity	NPD3082	Discontinued
0.743	Intermediate Similarity	NPD926	Approved
0.743	Intermediate Similarity	NPD925	Approved
0.7423	Intermediate Similarity	NPD3825	Phase 3
0.7421	Intermediate Similarity	NPD5913	Phase 3
0.7421	Intermediate Similarity	NPD4699	Discontinued
0.7421	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD750	Phase 2
0.7416	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD1915	Phase 1
0.7411	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD8272	Phase 2
0.7402	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3576	Approved
0.7399	Intermediate Similarity	NPD3575	Approved
0.7399	Intermediate Similarity	NPD3100	Discontinued
0.7391	Intermediate Similarity	NPD4181	Approved
0.7387	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD6178	Phase 3
0.7368	Intermediate Similarity	NPD8063	Discontinued
0.7366	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1392	Approved
0.7333	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5426	Phase 3
0.7316	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3525	Discontinued
0.7306	Intermediate Similarity	NPD4999	Phase 3
0.7306	Intermediate Similarity	NPD4998	Phase 3
0.7304	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6957	Approved
0.7304	Intermediate Similarity	NPD6958	Approved
0.73	Intermediate Similarity	NPD2509	Approved
0.73	Intermediate Similarity	NPD2510	Approved
0.7293	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4128	Approved
0.7282	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3323	Discontinued
0.7277	Intermediate Similarity	NPD7558	Phase 2
0.7277	Intermediate Similarity	NPD5117	Phase 2
0.7273	Intermediate Similarity	NPD8072	Approved
0.7273	Intermediate Similarity	NPD715	Phase 3
0.7269	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2383	Phase 1
0.7257	Intermediate Similarity	NPD2172	Phase 1
0.7254	Intermediate Similarity	NPD5428	Discontinued
0.7253	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8322	Phase 2
0.725	Intermediate Similarity	NPD4865	Approved
0.7241	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD2720	Phase 1
0.7238	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4795	Phase 2
0.7231	Intermediate Similarity	NPD5003	Discontinued
0.7228	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6711	Approved
0.7219	Intermediate Similarity	NPD6452	Discontinued
0.7219	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7618	Phase 3
0.7216	Intermediate Similarity	NPD7619	Phase 3
0.7209	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3717	Discontinued
0.7208	Intermediate Similarity	NPD1739	Approved
0.7208	Intermediate Similarity	NPD1740	Approved
0.7207	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD8094	Discontinued
0.7204	Intermediate Similarity	NPD6159	Phase 2
0.7202	Intermediate Similarity	NPD4615	Phase 2
0.7202	Intermediate Similarity	NPD6569	Phase 2
0.72	Intermediate Similarity	NPD7957	Phase 1
0.72	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3402	Phase 1
0.7195	Intermediate Similarity	NPD9080	Approved
0.7193	Intermediate Similarity	NPD1649	Discontinued
0.7188	Intermediate Similarity	NPD1043	Phase 3
0.7184	Intermediate Similarity	NPD7423	Phase 2
0.7184	Intermediate Similarity	NPD7469	Discontinued
0.7181	Intermediate Similarity	NPD3178	Discontinued
0.7181	Intermediate Similarity	NPD1895	Discontinued
0.7174	Intermediate Similarity	NPD3117	Approved
0.7174	Intermediate Similarity	NPD3116	Approved
0.7173	Intermediate Similarity	NPD3961	Discontinued
0.7173	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5413	Phase 2
0.7164	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6227	Discontinued
0.7158	Intermediate Similarity	NPD5555	Phase 1
0.7158	Intermediate Similarity	NPD2640	Approved
0.7158	Intermediate Similarity	NPD5021	Discontinued
0.7158	Intermediate Similarity	NPD2641	Approved
0.7157	Intermediate Similarity	NPD2175	Phase 3
0.7157	Intermediate Similarity	NPD2176	Approved
0.7157	Intermediate Similarity	NPD2177	Approved
0.7151	Intermediate Similarity	NPD416	Approved
0.715	Intermediate Similarity	NPD4038	Approved
0.715	Intermediate Similarity	NPD4122	Approved
0.715	Intermediate Similarity	NPD4034	Approved
0.715	Intermediate Similarity	NPD4036	Approved
0.715	Intermediate Similarity	NPD4039	Approved
0.715	Intermediate Similarity	NPD32	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