NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	241.11
Volume:	255.085
LogP:	4.068
LogD:	3.647
LogS:	-5.723
# Rotatable Bonds:	2
TPSA:	34.25
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	1.937
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.958
MDCK Permeability:	1.6663949281792156e-05
Pgp-inhibitor:	0.375
Pgp-substrate:	0.9
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.678
30% Bioavailability (F30%):	0.766

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.502
Plasma Protein Binding (PPB):	94.2648696899414%
Volume Distribution (VD):	0.724
Pgp-substrate:	4.424070358276367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.755
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.364
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.678
CYP2D6-substrate:	0.951
CYP3A4-inhibitor:	0.71
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	7.149
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.897
Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.888
Carcinogencity:	0.857
Eye Corrosion:	0.084
Eye Irritation:	0.985
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC131017

Natural Product ID:	NPC131017
*Common Name:**	Glycozolidine
IUPAC Name:	2,6-dimethoxy-3-methyl-9H-carbazole
Synonyms:	Glycozolidine
Standard InCHIKey:	MKQKWPIESXSKSS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H15NO2/c1-9-6-11-12-7-10(17-2)4-5-13(12)16-14(11)8-15(9)18-3/h4-8,16H,1-3H3
SMILES:	COc1ccc2c(c1)c1cc(C)c(cc1[nH]2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463555
PubChem CID:	147297
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO17936	Glycosmis arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387647]
NPO17936	Glycosmis arborea	Species	Rutaceae	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	9

Activity Type	# Activity
Cell Line	4
Organism	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[501763]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[501763]
NPT2	Others	Unspecified		Activity	=	24.3	%	PMID[501763]
NPT2	Others	Unspecified		Activity	=	51.3	%	PMID[501763]
NPT2	Others	Unspecified		Activity	=	76.0	%	PMID[501763]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[501763]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	>	50000.0	nM	PMID[501764]

☑ 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 NPC131017 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	754
0.1-0.2	4628
0.2-0.3	12763
0.3-0.4	6489
0.4-0.5	12969
0.5-0.6	3093
0.6-0.7	1509
0.7-0.8	366
0.8-0.85	72
0.85-0.9	33
0.9-0.95	18
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC162484
0.9399	High Similarity	NPC193777
0.933	High Similarity	NPC243834
0.933	High Similarity	NPC70956
0.9278	High Similarity	NPC72211
0.9194	High Similarity	NPC201697
0.9167	High Similarity	NPC70259
0.9111	High Similarity	NPC205934
0.9111	High Similarity	NPC43787
0.9048	High Similarity	NPC48353
0.8973	High Similarity	NPC291535
0.8973	High Similarity	NPC135887
0.8973	High Similarity	NPC475085
0.8973	High Similarity	NPC199277
0.8973	High Similarity	NPC475112
0.8927	High Similarity	NPC84478
0.8919	High Similarity	NPC267423
0.8912	High Similarity	NPC46561
0.8907	High Similarity	NPC153042
0.887	High Similarity	NPC176127
0.887	High Similarity	NPC212535
0.8833	High Similarity	NPC242928
0.883	High Similarity	NPC476106
0.8817	High Similarity	NPC476044
0.8777	High Similarity	NPC470930
0.8771	High Similarity	NPC94943
0.8715	High Similarity	NPC190007
0.8701	High Similarity	NPC88363
0.8684	High Similarity	NPC4687
0.8684	High Similarity	NPC249583
0.8653	High Similarity	NPC310211
0.8653	High Similarity	NPC308137
0.8632	High Similarity	NPC45190
0.8632	High Similarity	NPC300156
0.861	High Similarity	NPC128823
0.8579	High Similarity	NPC473179
0.8564	High Similarity	NPC329747
0.8564	High Similarity	NPC116238
0.8526	High Similarity	NPC223427
0.8525	High Similarity	NPC246700
0.8515	High Similarity	NPC252251
0.8505	High Similarity	NPC87413
0.85	High Similarity	NPC474798
0.8497	Intermediate Similarity	NPC209769
0.8477	Intermediate Similarity	NPC169402
0.8475	Intermediate Similarity	NPC474409
0.8442	Intermediate Similarity	NPC86078
0.8434	Intermediate Similarity	NPC247803
0.8431	Intermediate Similarity	NPC477531
0.8426	Intermediate Similarity	NPC170114
0.8424	Intermediate Similarity	NPC296527
0.84	Intermediate Similarity	NPC477532
0.8392	Intermediate Similarity	NPC208084
0.8382	Intermediate Similarity	NPC209174
0.8378	Intermediate Similarity	NPC76748
0.8376	Intermediate Similarity	NPC470549
0.8374	Intermediate Similarity	NPC473185
0.8368	Intermediate Similarity	NPC329793
0.8351	Intermediate Similarity	NPC13880
0.8351	Intermediate Similarity	NPC251090
0.835	Intermediate Similarity	NPC174760
0.835	Intermediate Similarity	NPC477533
0.835	Intermediate Similarity	NPC150239
0.8342	Intermediate Similarity	NPC307963
0.8333	Intermediate Similarity	NPC92111
0.8325	Intermediate Similarity	NPC232727
0.8324	Intermediate Similarity	NPC128751
0.8316	Intermediate Similarity	NPC208284
0.8308	Intermediate Similarity	NPC198503
0.829	Intermediate Similarity	NPC285558
0.828	Intermediate Similarity	NPC469497
0.828	Intermediate Similarity	NPC106833
0.8272	Intermediate Similarity	NPC11017
0.8272	Intermediate Similarity	NPC176538
0.8265	Intermediate Similarity	NPC199667
0.8265	Intermediate Similarity	NPC11464
0.8256	Intermediate Similarity	NPC475910
0.8256	Intermediate Similarity	NPC39679
0.8252	Intermediate Similarity	NPC475253
0.8235	Intermediate Similarity	NPC227908
0.8232	Intermediate Similarity	NPC478074
0.823	Intermediate Similarity	NPC6786
0.8218	Intermediate Similarity	NPC280799
0.8214	Intermediate Similarity	NPC473181
0.8187	Intermediate Similarity	NPC72980
0.8186	Intermediate Similarity	NPC179287
0.8182	Intermediate Similarity	NPC316981
0.8182	Intermediate Similarity	NPC473180
0.8182	Intermediate Similarity	NPC94157
0.8173	Intermediate Similarity	NPC471304
0.8163	Intermediate Similarity	NPC470931
0.815	Intermediate Similarity	NPC3207
0.8086	Intermediate Similarity	NPC473182
0.8081	Intermediate Similarity	NPC123976
0.8081	Intermediate Similarity	NPC167860
0.8057	Intermediate Similarity	NPC473183
0.8053	Intermediate Similarity	NPC475190
0.805	Intermediate Similarity	NPC266931
0.805	Intermediate Similarity	NPC39500
0.804	Intermediate Similarity	NPC187501
0.8011	Intermediate Similarity	NPC26850
0.799	Intermediate Similarity	NPC121772
0.798	Intermediate Similarity	NPC210828
0.798	Intermediate Similarity	NPC96321
0.798	Intermediate Similarity	NPC473041
0.798	Intermediate Similarity	NPC86834
0.7971	Intermediate Similarity	NPC202503
0.7962	Intermediate Similarity	NPC277351
0.7962	Intermediate Similarity	NPC473184
0.796	Intermediate Similarity	NPC469592
0.796	Intermediate Similarity	NPC471080
0.795	Intermediate Similarity	NPC23294
0.7943	Intermediate Similarity	NPC26872
0.7941	Intermediate Similarity	NPC193267
0.7941	Intermediate Similarity	NPC213530
0.7926	Intermediate Similarity	NPC204385
0.7925	Intermediate Similarity	NPC473187
0.7923	Intermediate Similarity	NPC312872
0.7913	Intermediate Similarity	NPC144452
0.7906	Intermediate Similarity	NPC99666
0.7902	Intermediate Similarity	NPC132642
0.7902	Intermediate Similarity	NPC225279
0.79	Intermediate Similarity	NPC303951
0.7892	Intermediate Similarity	NPC184408
0.7884	Intermediate Similarity	NPC46580
0.7861	Intermediate Similarity	NPC9894
0.7826	Intermediate Similarity	NPC280272
0.7819	Intermediate Similarity	NPC62069
0.7812	Intermediate Similarity	NPC280964
0.7812	Intermediate Similarity	NPC141915
0.7812	Intermediate Similarity	NPC114335
0.7807	Intermediate Similarity	NPC206201
0.7806	Intermediate Similarity	NPC315957
0.7805	Intermediate Similarity	NPC469594
0.7794	Intermediate Similarity	NPC152768
0.7794	Intermediate Similarity	NPC148183
0.7789	Intermediate Similarity	NPC66083
0.7778	Intermediate Similarity	NPC473189
0.7778	Intermediate Similarity	NPC314002
0.7778	Intermediate Similarity	NPC310118
0.7778	Intermediate Similarity	NPC60621
0.7756	Intermediate Similarity	NPC305984
0.7756	Intermediate Similarity	NPC314552
0.775	Intermediate Similarity	NPC321428
0.7737	Intermediate Similarity	NPC160381
0.7732	Intermediate Similarity	NPC326634
0.7725	Intermediate Similarity	NPC274640
0.7725	Intermediate Similarity	NPC204717
0.7718	Intermediate Similarity	NPC303658
0.7716	Intermediate Similarity	NPC19872
0.7711	Intermediate Similarity	NPC476465
0.7688	Intermediate Similarity	NPC245816
0.7688	Intermediate Similarity	NPC476138
0.768	Intermediate Similarity	NPC106937
0.7673	Intermediate Similarity	NPC185782
0.7672	Intermediate Similarity	NPC220765
0.7659	Intermediate Similarity	NPC118228
0.7653	Intermediate Similarity	NPC474688
0.7647	Intermediate Similarity	NPC294620
0.7644	Intermediate Similarity	NPC171171
0.7641	Intermediate Similarity	NPC276517
0.7638	Intermediate Similarity	NPC295898
0.7637	Intermediate Similarity	NPC118511
0.7636	Intermediate Similarity	NPC475666
0.7626	Intermediate Similarity	NPC249040
0.7626	Intermediate Similarity	NPC234197
0.7619	Intermediate Similarity	NPC122436
0.7619	Intermediate Similarity	NPC211416
0.7614	Intermediate Similarity	NPC306376
0.7598	Intermediate Similarity	NPC294375
0.7594	Intermediate Similarity	NPC110151
0.7591	Intermediate Similarity	NPC81939
0.7582	Intermediate Similarity	NPC177404
0.7577	Intermediate Similarity	NPC89549
0.7576	Intermediate Similarity	NPC18487
0.7563	Intermediate Similarity	NPC77555
0.7562	Intermediate Similarity	NPC36229
0.7562	Intermediate Similarity	NPC476581
0.7562	Intermediate Similarity	NPC16452
0.7561	Intermediate Similarity	NPC26679
0.7559	Intermediate Similarity	NPC311906
0.7559	Intermediate Similarity	NPC471762
0.7553	Intermediate Similarity	NPC96890
0.7553	Intermediate Similarity	NPC184964
0.7536	Intermediate Similarity	NPC51388
0.7535	Intermediate Similarity	NPC474192
0.7535	Intermediate Similarity	NPC475720
0.7534	Intermediate Similarity	NPC477066
0.7525	Intermediate Similarity	NPC472111
0.7513	Intermediate Similarity	NPC242209
0.7512	Intermediate Similarity	NPC478078
0.7512	Intermediate Similarity	NPC157931
0.75	Intermediate Similarity	NPC174758
0.75	Intermediate Similarity	NPC477067
0.75	Intermediate Similarity	NPC42591
0.75	Intermediate Similarity	NPC21638
0.75	Intermediate Similarity	NPC478081
0.75	Intermediate Similarity	NPC469589
0.75	Intermediate Similarity	NPC473540
0.75	Intermediate Similarity	NPC174672

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 NPC131017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	441
0.1-0.2	705
0.2-0.3	853
0.3-0.4	1562
0.4-0.5	2797
0.5-0.6	1984
0.6-0.7	684
0.7-0.8	115
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8737	High Similarity	NPD5658	Approved
0.8511	High Similarity	NPD4118	Clinical (unspecified phase)
0.8342	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8342	Intermediate Similarity	NPD1038	Approved
0.8342	Intermediate Similarity	NPD3003	Approved
0.8298	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1768	Approved
0.8105	Intermediate Similarity	NPD4418	Discontinued
0.801	Intermediate Similarity	NPD5903	Approved
0.801	Intermediate Similarity	NPD5902	Approved
0.7892	Intermediate Similarity	NPD3920	Phase 2
0.7882	Intermediate Similarity	NPD5612	Discontinued
0.7839	Intermediate Similarity	NPD1392	Approved
0.7828	Intermediate Similarity	NPD4795	Phase 2
0.7806	Intermediate Similarity	NPD1739	Approved
0.7806	Intermediate Similarity	NPD1740	Approved
0.7756	Intermediate Similarity	NPD5164	Discontinued
0.7755	Intermediate Similarity	NPD3825	Phase 3
0.775	Intermediate Similarity	NPD7452	Approved
0.775	Intermediate Similarity	NPD7453	Approved
0.775	Intermediate Similarity	NPD7222	Phase 2
0.7729	Intermediate Similarity	NPD5930	Phase 3
0.7718	Intermediate Similarity	NPD5632	Approved
0.7718	Intermediate Similarity	NPD6985	Discontinued
0.7711	Intermediate Similarity	NPD2187	Approved
0.7711	Intermediate Similarity	NPD2189	Approved
0.7684	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD7194	Discontinued
0.768	Intermediate Similarity	NPD802	Phase 2
0.7656	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6242	Discontinued
0.7612	Intermediate Similarity	NPD8403	Phase 1
0.759	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7558	Phase 2
0.7577	Intermediate Similarity	NPD5913	Phase 3
0.7577	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1325	Approved
0.7568	Intermediate Similarity	NPD1326	Approved
0.7568	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5530	Phase 1
0.7524	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5067	Phase 2
0.7512	Intermediate Similarity	NPD5066	Phase 2
0.75	Intermediate Similarity	NPD4511	Phase 1
0.7477	Intermediate Similarity	NPD5559	Phase 2
0.7476	Intermediate Similarity	NPD3815	Phase 1
0.7476	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD3816	Phase 1
0.7449	Intermediate Similarity	NPD3922	Approved
0.7449	Intermediate Similarity	NPD3923	Approved
0.7449	Intermediate Similarity	NPD3921	Approved
0.7449	Intermediate Similarity	NPD3924	Approved
0.7448	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6494	Phase 2
0.7376	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD4885	Approved
0.7366	Intermediate Similarity	NPD8358	Approved
0.7346	Intermediate Similarity	NPD3763	Approved
0.7343	Intermediate Similarity	NPD4502	Phase 2
0.7333	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1954	Phase 1
0.7321	Intermediate Similarity	NPD3257	Approved
0.7303	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7948	Phase 1
0.7286	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5256	Discontinued
0.7264	Intermediate Similarity	NPD3875	Discontinued
0.726	Intermediate Similarity	NPD6220	Phase 3
0.7254	Intermediate Similarity	NPD4203	Approved
0.7254	Intermediate Similarity	NPD4204	Approved
0.7252	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD2749	Discontinued
0.7243	Intermediate Similarity	NPD7221	Approved
0.7243	Intermediate Similarity	NPD7219	Approved
0.7225	Intermediate Similarity	NPD6243	Phase 3
0.7225	Intermediate Similarity	NPD6244	Phase 3
0.7214	Intermediate Similarity	NPD5003	Discontinued
0.7214	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD8364	Approved
0.7203	Intermediate Similarity	NPD8363	Approved
0.72	Intermediate Similarity	NPD6230	Discontinued
0.72	Intermediate Similarity	NPD4349	Approved
0.72	Intermediate Similarity	NPD6590	Discontinued
0.72	Intermediate Similarity	NPD4350	Approved
0.7193	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD484	Approved
0.7183	Intermediate Similarity	NPD3258	Approved
0.7164	Intermediate Similarity	NPD5512	Phase 3
0.7163	Intermediate Similarity	NPD6736	Discontinued
0.7158	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7555	Discontinued
0.7155	Intermediate Similarity	NPD7955	Approved
0.7155	Intermediate Similarity	NPD7956	Approved
0.715	Intermediate Similarity	NPD5429	Discontinued
0.7149	Intermediate Similarity	NPD6963	Approved
0.7149	Intermediate Similarity	NPD6964	Approved
0.7143	Intermediate Similarity	NPD8396	Approved
0.7143	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8395	Approved
0.7143	Intermediate Similarity	NPD6790	Phase 1
0.7143	Intermediate Similarity	NPD7069	Discontinued
0.7136	Intermediate Similarity	NPD3354	Phase 2
0.7136	Intermediate Similarity	NPD3397	Phase 2
0.7124	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4952	Phase 3
0.7123	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2916	Discontinued
0.7114	Intermediate Similarity	NPD6251	Discontinued
0.7104	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3402	Phase 1
0.7101	Intermediate Similarity	NPD6150	Discontinued
0.7101	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4995	Approved
0.7091	Intermediate Similarity	NPD4996	Approved
0.7089	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD2565	Phase 2
0.7085	Intermediate Similarity	NPD2564	Approved
0.7083	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6550	Discontinued
0.7075	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5482	Discontinued
0.7054	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4925	Approved
0.7042	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6473	Phase 1
0.7032	Intermediate Similarity	NPD3259	Approved
0.7027	Intermediate Similarity	NPD4373	Phase 2
0.7025	Intermediate Similarity	NPD8428	Approved
0.7025	Intermediate Similarity	NPD8465	Approved
0.7025	Intermediate Similarity	NPD8467	Approved
0.7025	Intermediate Similarity	NPD8427	Approved
0.7025	Intermediate Similarity	NPD8429	Approved
0.7025	Intermediate Similarity	NPD8466	Approved
0.7018	Intermediate Similarity	NPD5488	Discontinued
0.7014	Intermediate Similarity	NPD5939	Approved
0.7014	Intermediate Similarity	NPD5936	Approved
0.701	Intermediate Similarity	NPD2727	Phase 2
0.701	Intermediate Similarity	NPD5810	Discontinued
0.7005	Intermediate Similarity	NPD6324	Phase 1
0.7004	Intermediate Similarity	NPD7803	Approved
0.7	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD774	Phase 3
0.6991	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7051	Phase 3
0.6986	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD2151	Approved
0.6976	Remote Similarity	NPD3814	Phase 1
0.6976	Remote Similarity	NPD2175	Phase 3
0.6976	Remote Similarity	NPD2176	Approved
0.6976	Remote Similarity	NPD2177	Approved
0.6974	Remote Similarity	NPD7479	Phase 2
0.6974	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4035	Approved
0.6971	Remote Similarity	NPD4039	Approved
0.6971	Remote Similarity	NPD4037	Approved
0.6971	Remote Similarity	NPD31	Approved
0.6971	Remote Similarity	NPD4034	Approved
0.6971	Remote Similarity	NPD4033	Approved
0.6971	Remote Similarity	NPD32	Approved
0.6971	Remote Similarity	NPD4122	Approved
0.6971	Remote Similarity	NPD4036	Approved
0.6971	Remote Similarity	NPD4038	Approved
0.697	Remote Similarity	NPD4889	Approved
0.6968	Remote Similarity	NPD8512	Phase 3
0.6963	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6988	Phase 1
0.6961	Remote Similarity	NPD2952	Discontinued
0.696	Remote Similarity	NPD4876	Phase 3
0.696	Remote Similarity	NPD4875	Phase 3
0.6959	Remote Similarity	NPD4354	Approved
0.6957	Remote Similarity	NPD3835	Phase 3
0.6957	Remote Similarity	NPD3833	Phase 3
0.6957	Remote Similarity	NPD6208	Discontinued
0.6955	Remote Similarity	NPD4328	Approved
0.6952	Remote Similarity	NPD7672	Approved
0.6952	Remote Similarity	NPD7671	Approved
0.6948	Remote Similarity	NPD4457	Phase 2
0.6947	Remote Similarity	NPD5905	Phase 1
0.6946	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1592	Phase 3
0.6941	Remote Similarity	NPD7719	Discontinued
0.6937	Remote Similarity	NPD6962	Phase 2
0.6935	Remote Similarity	NPD5617	Suspended
0.6934	Remote Similarity	NPD5416	Discontinued
0.6931	Remote Similarity	NPD6569	Phase 2
0.6923	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6991	Approved
0.6916	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2410	Phase 2
0.6911	Remote Similarity	NPD8460	Approved
0.6911	Remote Similarity	NPD8426	Approved
0.6911	Remote Similarity	NPD8425	Approved
0.6911	Remote Similarity	NPD8459	Approved
0.6904	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3330	Phase 1
0.6901	Remote Similarity	NPD6202	Discontinued
0.69	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD8091	Phase 3
0.6892	Remote Similarity	NPD5801	Clinical (unspecified phase)

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