NPASS Compound

Structure

NPC153042 OpenBabel07101718202D 21 23 0 0 0 0 0 0 0 0999 V2000 1.8171 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 -3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 -1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 10 2 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 13 2 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 11 17 2 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	281.14
Volume:	304.337
LogP:	5.104
LogD:	3.818
LogS:	-3.111
# Rotatable Bonds:	2
TPSA:	56.25
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	2.678
Fsp3:	0.222
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:	-5.097
MDCK Permeability:	1.0867173841688782e-05
Pgp-inhibitor:	0.637
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	97.01782989501953%
Volume Distribution (VD):	1.571
Pgp-substrate:	4.139670372009277%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.599
CYP2C19-inhibitor:	0.864
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.882
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.271
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	12.971
Half-life (T1/2):	0.564

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.441
AMES Toxicity:	0.738
Rat Oral Acute Toxicity:	0.554
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.942
Carcinogencity:	0.652
Eye Corrosion:	0.025
Eye Irritation:	0.967
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC153042

Natural Product ID:	NPC153042
*Common Name:**	Glybomine C
IUPAC Name:	3-methyl-5-(3-methylbut-2-enyl)-9H-carbazole-2,6-diol
Synonyms:	Glybomine C
Standard InCHIKey:	BSVSEIFLTGZOTG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H19NO2/c1-10(2)4-5-12-16(20)7-6-14-18(12)13-8-11(3)17(21)9-15(13)19-14/h4,6-9,19-21H,5H2,1-3H3
SMILES:	CC(=CCc1c(ccc2c1c1cc(C)c(cc1[nH]2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459131
PubChem CID:	11357993
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	8

Activity Type	# Activity
Cell Line	4
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[506317]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[506317]
NPT2	Others	Unspecified		Activity	=	45.6	%	PMID[506317]
NPT2	Others	Unspecified		Activity	=	13.4	%	PMID[506317]
NPT2	Others	Unspecified		Activity	=	68.9	%	PMID[506317]
NPT2	Others	Unspecified		Activity	=	94.6	%	PMID[506317]

☑ 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 NPC153042 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	567
0.1-0.2	4066
0.2-0.3	13309
0.3-0.4	8342
0.4-0.5	11299
0.5-0.6	3082
0.6-0.7	1610
0.7-0.8	334
0.8-0.85	59
0.85-0.9	16
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9598	High Similarity	NPC246700
0.9508	High Similarity	NPC193777
0.9425	High Similarity	NPC94943
0.9375	High Similarity	NPC128751
0.9368	High Similarity	NPC190007
0.9322	High Similarity	NPC106833
0.9322	High Similarity	NPC469497
0.931	High Similarity	NPC212535
0.9255	High Similarity	NPC48353
0.9138	High Similarity	NPC88363
0.9016	High Similarity	NPC70956
0.9016	High Similarity	NPC243834
0.8908	High Similarity	NPC474409
0.8907	High Similarity	NPC131017
0.8895	High Similarity	NPC201697
0.8777	High Similarity	NPC475112
0.8777	High Similarity	NPC291535
0.8777	High Similarity	NPC475085
0.873	High Similarity	NPC162484
0.8705	High Similarity	NPC9894
0.8614	High Similarity	NPC252251
0.8603	High Similarity	NPC72980
0.8571	High Similarity	NPC209174
0.8529	High Similarity	NPC477531
0.8495	Intermediate Similarity	NPC99666
0.8482	Intermediate Similarity	NPC199277
0.8482	Intermediate Similarity	NPC135887
0.8469	Intermediate Similarity	NPC294620
0.8466	Intermediate Similarity	NPC72211
0.8457	Intermediate Similarity	NPC70259
0.8446	Intermediate Similarity	NPC476106
0.8418	Intermediate Similarity	NPC23294
0.8404	Intermediate Similarity	NPC205934
0.8404	Intermediate Similarity	NPC43787
0.8367	Intermediate Similarity	NPC303951
0.8333	Intermediate Similarity	NPC267423
0.8316	Intermediate Similarity	NPC209769
0.8308	Intermediate Similarity	NPC473179
0.828	Intermediate Similarity	NPC46580
0.8265	Intermediate Similarity	NPC210828
0.8265	Intermediate Similarity	NPC86834
0.8247	Intermediate Similarity	NPC223427
0.8238	Intermediate Similarity	NPC6786
0.8209	Intermediate Similarity	NPC314552
0.8182	Intermediate Similarity	NPC473182
0.8173	Intermediate Similarity	NPC39679
0.8172	Intermediate Similarity	NPC314002
0.8144	Intermediate Similarity	NPC476044
0.8137	Intermediate Similarity	NPC477532
0.8128	Intermediate Similarity	NPC171171
0.8119	Intermediate Similarity	NPC293151
0.8118	Intermediate Similarity	NPC204717
0.8116	Intermediate Similarity	NPC473185
0.8115	Intermediate Similarity	NPC326634
0.8093	Intermediate Similarity	NPC249040
0.8088	Intermediate Similarity	NPC150239
0.8081	Intermediate Similarity	NPC470931
0.8069	Intermediate Similarity	NPC3207
0.8068	Intermediate Similarity	NPC202503
0.8065	Intermediate Similarity	NPC220765
0.8058	Intermediate Similarity	NPC211416
0.8041	Intermediate Similarity	NPC128823
0.8031	Intermediate Similarity	NPC77555
0.8021	Intermediate Similarity	NPC276517
0.802	Intermediate Similarity	NPC470930
0.8	Intermediate Similarity	NPC11464
0.8	Intermediate Similarity	NPC86078
0.799	Intermediate Similarity	NPC247803
0.799	Intermediate Similarity	NPC306376
0.799	Intermediate Similarity	NPC46561
0.798	Intermediate Similarity	NPC183407
0.7979	Intermediate Similarity	NPC476319
0.7971	Intermediate Similarity	NPC51388
0.797	Intermediate Similarity	NPC478074
0.796	Intermediate Similarity	NPC208284
0.796	Intermediate Similarity	NPC87413
0.7946	Intermediate Similarity	NPC184964
0.7946	Intermediate Similarity	NPC96890
0.7938	Intermediate Similarity	NPC474188
0.7929	Intermediate Similarity	NPC475070
0.7926	Intermediate Similarity	NPC84478
0.791	Intermediate Similarity	NPC199667
0.7887	Intermediate Similarity	NPC242209
0.7874	Intermediate Similarity	NPC280799
0.7872	Intermediate Similarity	NPC176127
0.7871	Intermediate Similarity	NPC294375
0.7861	Intermediate Similarity	NPC473181
0.7857	Intermediate Similarity	NPC470126
0.7853	Intermediate Similarity	NPC242928
0.7833	Intermediate Similarity	NPC473180
0.7833	Intermediate Similarity	NPC316981
0.7826	Intermediate Similarity	NPC174760
0.7822	Intermediate Similarity	NPC5145
0.782	Intermediate Similarity	NPC253580
0.7817	Intermediate Similarity	NPC329747
0.7816	Intermediate Similarity	NPC477609
0.7814	Intermediate Similarity	NPC473183
0.7811	Intermediate Similarity	NPC475910
0.781	Intermediate Similarity	NPC227908
0.7805	Intermediate Similarity	NPC469928
0.7805	Intermediate Similarity	NPC330009
0.7795	Intermediate Similarity	NPC472193
0.7794	Intermediate Similarity	NPC266931
0.7793	Intermediate Similarity	NPC132329
0.7784	Intermediate Similarity	NPC106937
0.7772	Intermediate Similarity	NPC280548
0.7772	Intermediate Similarity	NPC476116
0.7763	Intermediate Similarity	NPC160898
0.7762	Intermediate Similarity	NPC179287
0.7761	Intermediate Similarity	NPC249583
0.7761	Intermediate Similarity	NPC4687
0.7755	Intermediate Similarity	NPC156704
0.7751	Intermediate Similarity	NPC280272
0.7745	Intermediate Similarity	NPC310211
0.7745	Intermediate Similarity	NPC308137
0.7732	Intermediate Similarity	NPC114335
0.7732	Intermediate Similarity	NPC280964
0.7732	Intermediate Similarity	NPC141915
0.7727	Intermediate Similarity	NPC11017
0.7725	Intermediate Similarity	NPC214980
0.7721	Intermediate Similarity	NPC473184
0.7721	Intermediate Similarity	NPC277351
0.7718	Intermediate Similarity	NPC170114
0.7711	Intermediate Similarity	NPC45190
0.7711	Intermediate Similarity	NPC300156
0.7704	Intermediate Similarity	NPC251090
0.7704	Intermediate Similarity	NPC205403
0.77	Intermediate Similarity	NPC134848
0.77	Intermediate Similarity	NPC477135
0.77	Intermediate Similarity	NPC476098
0.7692	Intermediate Similarity	NPC307963
0.7685	Intermediate Similarity	NPC473187
0.7681	Intermediate Similarity	NPC169402
0.7673	Intermediate Similarity	NPC283117
0.7672	Intermediate Similarity	NPC478032
0.767	Intermediate Similarity	NPC470549
0.767	Intermediate Similarity	NPC116238
0.7667	Intermediate Similarity	NPC162748
0.7665	Intermediate Similarity	NPC89549
0.7664	Intermediate Similarity	NPC474701
0.7656	Intermediate Similarity	NPC477533
0.7653	Intermediate Similarity	NPC195314
0.7653	Intermediate Similarity	NPC274640
0.7638	Intermediate Similarity	NPC329793
0.7638	Intermediate Similarity	NPC213308
0.7621	Intermediate Similarity	NPC471080
0.7621	Intermediate Similarity	NPC469592
0.7619	Intermediate Similarity	NPC198503
0.7608	Intermediate Similarity	NPC193267
0.7608	Intermediate Similarity	NPC213530
0.7596	Intermediate Similarity	NPC16667
0.7594	Intermediate Similarity	NPC34508
0.7592	Intermediate Similarity	NPC19679
0.7585	Intermediate Similarity	NPC118228
0.7583	Intermediate Similarity	NPC144452
0.7581	Intermediate Similarity	NPC475253
0.7577	Intermediate Similarity	NPC32771
0.7574	Intermediate Similarity	NPC285558
0.7571	Intermediate Similarity	NPC225279
0.7571	Intermediate Similarity	NPC132642
0.757	Intermediate Similarity	NPC477608
0.7569	Intermediate Similarity	NPC184476
0.7565	Intermediate Similarity	NPC314573
0.756	Intermediate Similarity	NPC264285
0.7559	Intermediate Similarity	NPC200888
0.7554	Intermediate Similarity	NPC159319
0.7551	Intermediate Similarity	NPC324149
0.755	Intermediate Similarity	NPC45459
0.755	Intermediate Similarity	NPC315491
0.7549	Intermediate Similarity	NPC477111
0.7539	Intermediate Similarity	NPC474798
0.7538	Intermediate Similarity	NPC76748
0.7536	Intermediate Similarity	NPC477610
0.7527	Intermediate Similarity	NPC154293
0.7524	Intermediate Similarity	NPC208084
0.7512	Intermediate Similarity	NPC476041
0.7512	Intermediate Similarity	NPC304926
0.7512	Intermediate Similarity	NPC325297
0.75	Intermediate Similarity	NPC259545
0.75	Intermediate Similarity	NPC476175
0.75	Intermediate Similarity	NPC92111
0.75	Intermediate Similarity	NPC270918
0.7488	Intermediate Similarity	NPC12344
0.7488	Intermediate Similarity	NPC94157
0.7487	Intermediate Similarity	NPC296527
0.7476	Intermediate Similarity	NPC469594
0.7476	Intermediate Similarity	NPC471304
0.7473	Intermediate Similarity	NPC141353
0.7464	Intermediate Similarity	NPC74969
0.7459	Intermediate Similarity	NPC32028
0.7448	Intermediate Similarity	NPC314394
0.7437	Intermediate Similarity	NPC13880
0.7435	Intermediate Similarity	NPC270009
0.7435	Intermediate Similarity	NPC472443
0.7426	Intermediate Similarity	NPC232727
0.7423	Intermediate Similarity	NPC473189
0.7421	Intermediate Similarity	NPC477861
0.7415	Intermediate Similarity	NPC88008
0.7413	Intermediate Similarity	NPC476167
0.7413	Intermediate Similarity	NPC32200

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 NPC153042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	722
0.2-0.3	862
0.3-0.4	1560
0.4-0.5	2960
0.5-0.6	1985
0.6-0.7	631
0.7-0.8	84
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8429	Intermediate Similarity	NPD4511	Phase 1
0.827	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD5164	Discontinued
0.8158	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD1326	Approved
0.8066	Intermediate Similarity	NPD1325	Approved
0.799	Intermediate Similarity	NPD5658	Approved
0.7846	Intermediate Similarity	NPD7948	Phase 1
0.7811	Intermediate Similarity	NPD2916	Discontinued
0.78	Intermediate Similarity	NPD3003	Approved
0.7784	Intermediate Similarity	NPD802	Phase 2
0.7783	Intermediate Similarity	NPD5936	Approved
0.7783	Intermediate Similarity	NPD5939	Approved
0.7766	Intermediate Similarity	NPD2177	Approved
0.7766	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD2176	Approved
0.7766	Intermediate Similarity	NPD2175	Phase 3
0.7692	Intermediate Similarity	NPD1038	Approved
0.7677	Intermediate Similarity	NPD8396	Approved
0.7677	Intermediate Similarity	NPD8395	Approved
0.7633	Intermediate Similarity	NPD5612	Discontinued
0.7592	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6975	Discontinued
0.755	Intermediate Similarity	NPD484	Approved
0.7537	Intermediate Similarity	NPD5530	Phase 1
0.7513	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3814	Phase 1
0.75	Intermediate Similarity	NPD5902	Approved
0.75	Intermediate Similarity	NPD5903	Approved
0.75	Intermediate Similarity	NPD7222	Phase 2
0.75	Intermediate Similarity	NPD7452	Approved
0.75	Intermediate Similarity	NPD1768	Approved
0.75	Intermediate Similarity	NPD6290	Phase 2
0.75	Intermediate Similarity	NPD7453	Approved
0.7488	Intermediate Similarity	NPD2794	Discontinued
0.7475	Intermediate Similarity	NPD4418	Discontinued
0.7464	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4502	Phase 2
0.7405	Intermediate Similarity	NPD1685	Approved
0.7405	Intermediate Similarity	NPD1684	Approved
0.7402	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD2727	Phase 2
0.7347	Intermediate Similarity	NPD2383	Phase 1
0.7344	Intermediate Similarity	NPD3920	Phase 2
0.734	Intermediate Similarity	NPD1921	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4795	Phase 2
0.7311	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6159	Phase 2
0.7273	Intermediate Similarity	NPD7558	Phase 2
0.7273	Intermediate Similarity	NPD6494	Phase 2
0.7247	Intermediate Similarity	NPD1592	Phase 3
0.7246	Intermediate Similarity	NPD1392	Approved
0.7243	Intermediate Similarity	NPD5930	Phase 3
0.7238	Intermediate Similarity	NPD3330	Phase 1
0.7236	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5913	Phase 3
0.723	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6985	Discontinued
0.722	Intermediate Similarity	NPD3928	Approved
0.722	Intermediate Similarity	NPD3931	Approved
0.7206	Intermediate Similarity	NPD1739	Approved
0.7206	Intermediate Similarity	NPD1740	Approved
0.7205	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7194	Discontinued
0.7192	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5065	Approved
0.7181	Intermediate Similarity	NPD5140	Approved
0.7181	Intermediate Similarity	NPD5138	Approved
0.7176	Intermediate Similarity	NPD7221	Approved
0.7176	Intermediate Similarity	NPD7219	Approved
0.7165	Intermediate Similarity	NPD8386	Phase 2
0.7165	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4463	Approved
0.7158	Intermediate Similarity	NPD2844	Phase 3
0.7158	Intermediate Similarity	NPD4462	Approved
0.7157	Intermediate Similarity	NPD2762	Phase 2
0.7149	Intermediate Similarity	NPD3746	Discontinued
0.7143	Intermediate Similarity	NPD5003	Discontinued
0.712	Intermediate Similarity	NPD6158	Phase 2
0.712	Intermediate Similarity	NPD2882	Phase 1
0.712	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD3127	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3825	Phase 3
0.7072	Intermediate Similarity	NPD5254	Discontinued
0.707	Intermediate Similarity	NPD5632	Approved
0.7067	Intermediate Similarity	NPD5901	Discontinued
0.7056	Intermediate Similarity	NPD7112	Discontinued
0.7053	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5506	Approved
0.7051	Intermediate Similarity	NPD5507	Approved
0.7048	Intermediate Similarity	NPD2187	Approved
0.7048	Intermediate Similarity	NPD6376	Discontinued
0.7048	Intermediate Similarity	NPD2189	Approved
0.7044	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5488	Discontinued
0.703	Intermediate Similarity	NPD3404	Approved
0.7028	Intermediate Similarity	NPD5066	Phase 2
0.7028	Intermediate Similarity	NPD5067	Phase 2
0.7018	Intermediate Similarity	NPD1954	Phase 1
0.7018	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2564	Approved
0.7015	Intermediate Similarity	NPD2565	Phase 2
0.7014	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6242	Discontinued
0.7005	Intermediate Similarity	NPD2789	Approved
0.7005	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8431	Approved
0.7	Intermediate Similarity	NPD7603	Discontinued
0.6995	Remote Similarity	NPD3816	Phase 1
0.6995	Remote Similarity	NPD3815	Phase 1
0.6991	Remote Similarity	NPD2021	Discontinued
0.699	Remote Similarity	NPD4079	Approved
0.699	Remote Similarity	NPD4076	Approved
0.6985	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5599	Discontinued
0.6979	Remote Similarity	NPD5021	Discontinued
0.6972	Remote Similarity	NPD7726	Phase 1
0.6963	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3763	Approved
0.6959	Remote Similarity	NPD3875	Discontinued
0.6952	Remote Similarity	NPD8403	Phase 1
0.6946	Remote Similarity	NPD3922	Approved
0.6946	Remote Similarity	NPD3924	Approved
0.6946	Remote Similarity	NPD3921	Approved
0.6946	Remote Similarity	NPD3923	Approved
0.6939	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3506	Approved
0.6939	Remote Similarity	NPD3505	Approved
0.6938	Remote Similarity	NPD2920	Discontinued
0.6937	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD8244	Phase 2
0.6927	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD8358	Approved
0.6923	Remote Similarity	NPD6492	Phase 2
0.6919	Remote Similarity	NPD4204	Approved
0.6919	Remote Similarity	NPD4203	Approved
0.6919	Remote Similarity	NPD5429	Discontinued
0.6917	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7069	Discontinued
0.6913	Remote Similarity	NPD6230	Discontinued
0.6913	Remote Similarity	NPD4350	Approved
0.6913	Remote Similarity	NPD4349	Approved
0.6904	Remote Similarity	NPD7479	Phase 2
0.6893	Remote Similarity	NPD1219	Approved
0.6893	Remote Similarity	NPD1218	Approved
0.6888	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD5100	Phase 3
0.6888	Remote Similarity	NPD2380	Approved
0.6888	Remote Similarity	NPD2381	Approved
0.6888	Remote Similarity	NPD2382	Approved
0.6884	Remote Similarity	NPD5596	Phase 2
0.6878	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7418	Discontinued
0.6872	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6220	Phase 3
0.6869	Remote Similarity	NPD6595	Phase 3
0.6866	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6736	Discontinued
0.6863	Remote Similarity	NPD5937	Approved
0.6861	Remote Similarity	NPD5559	Phase 2
0.6861	Remote Similarity	NPD7555	Discontinued
0.686	Remote Similarity	NPD8363	Approved
0.686	Remote Similarity	NPD8364	Approved
0.6856	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6145	Phase 1
0.6832	Remote Similarity	NPD4948	Discontinued
0.6827	Remote Similarity	NPD2151	Approved
0.6816	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6978	Phase 2
0.6814	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2952	Discontinued
0.6812	Remote Similarity	NPD4561	Discontinued
0.6808	Remote Similarity	NPD7671	Approved
0.6808	Remote Similarity	NPD7672	Approved
0.6804	Remote Similarity	NPD3258	Approved
0.6803	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD1534	Approved
0.6796	Remote Similarity	NPD6590	Discontinued
0.6796	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3986	Discontinued
0.6794	Remote Similarity	NPD4600	Approved
0.6794	Remote Similarity	NPD4601	Approved
0.6794	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4044	Discontinued

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