NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	359.576
LogP:	3.141
LogD:	2.403
LogS:	-3.972
# Rotatable Bonds:	4
TPSA:	84.58
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	4.813
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.811
MDCK Permeability:	2.6158339096582495e-05
Pgp-inhibitor:	0.131
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146
Plasma Protein Binding (PPB):	80.09392547607422%
Volume Distribution (VD):	0.321
Pgp-substrate:	4.883237361907959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.257
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.493
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.444
CYP3A4-inhibitor:	0.323
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	8.896
Half-life (T1/2):	0.508

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.135
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.25
Maximum Recommended Daily Dose:	0.464
Skin Sensitization:	0.652
Carcinogencity:	0.069
Eye Corrosion:	0.032
Eye Irritation:	0.219
Respiratory Toxicity:	0.829

Download Data

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

Natural Product: NPC208084

Natural Product ID:	NPC208084
*Common Name:**	Claurailas A
IUPAC Name:	1,7-dimethoxy-9H-carbazole-3-carbaldehyde
Synonyms:	Claurailas A
Standard InCHIKey:	LEYWMXGGVZTHDM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H13NO3/c1-18-10-3-4-11-12-5-9(8-17)6-14(19-2)15(12)16-13(11)7-10/h3-8,16H,1-2H3
SMILES:	COc1ccc2c(c1)[nH]c1c2cc(cc1OC)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689795
PubChem CID:	51039825
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
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21302964]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3236015]
NPO21978	Clausena harmandiana	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	13500.0	nM	PMID[534691]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	200000.0	nM	PMID[534691]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	200000.0	nM	PMID[534691]

☑ 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 NPC208084 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	640
0.1-0.2	3835
0.2-0.3	13296
0.3-0.4	3997
0.4-0.5	15848
0.5-0.6	3184
0.6-0.7	1374
0.7-0.8	454
0.8-0.85	34
0.85-0.9	21
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC179287
0.9639	High Similarity	NPC187501
0.945	High Similarity	NPC225279
0.9433	High Similarity	NPC249583
0.9343	High Similarity	NPC39500
0.9196	High Similarity	NPC310211
0.9196	High Similarity	NPC308137
0.9167	High Similarity	NPC144452
0.9158	High Similarity	NPC46561
0.9158	High Similarity	NPC184408
0.9137	High Similarity	NPC4687
0.9086	High Similarity	NPC45190
0.8971	High Similarity	NPC247803
0.8955	High Similarity	NPC87413
0.8952	High Similarity	NPC474688
0.8947	High Similarity	NPC274640
0.8883	High Similarity	NPC150239
0.885	High Similarity	NPC283117
0.8841	High Similarity	NPC198503
0.8826	High Similarity	NPC39370
0.8824	High Similarity	NPC118228
0.8824	High Similarity	NPC116238
0.88	High Similarity	NPC300156
0.8768	High Similarity	NPC294375
0.8738	High Similarity	NPC169402
0.8738	High Similarity	NPC293151
0.8732	High Similarity	NPC473186
0.8713	High Similarity	NPC39679
0.8667	High Similarity	NPC51388
0.8624	High Similarity	NPC475844
0.8612	High Similarity	NPC174760
0.8608	High Similarity	NPC242928
0.8529	High Similarity	NPC86834
0.8529	High Similarity	NPC210828
0.8512	High Similarity	NPC474701
0.85	High Similarity	NPC128823
0.8495	Intermediate Similarity	NPC23294
0.8486	Intermediate Similarity	NPC6786
0.8447	Intermediate Similarity	NPC303951
0.8421	Intermediate Similarity	NPC3207
0.8392	Intermediate Similarity	NPC131017
0.8382	Intermediate Similarity	NPC470930
0.8299	Intermediate Similarity	NPC474798
0.8224	Intermediate Similarity	NPC280799
0.8223	Intermediate Similarity	NPC160381
0.8216	Intermediate Similarity	NPC473179
0.8213	Intermediate Similarity	NPC321428
0.8158	Intermediate Similarity	NPC473188
0.8143	Intermediate Similarity	NPC146418
0.8143	Intermediate Similarity	NPC9894
0.8128	Intermediate Similarity	NPC70956
0.8128	Intermediate Similarity	NPC243834
0.8108	Intermediate Similarity	NPC473187
0.8095	Intermediate Similarity	NPC199667
0.8088	Intermediate Similarity	NPC72211
0.8073	Intermediate Similarity	NPC470018
0.8069	Intermediate Similarity	NPC475190
0.8068	Intermediate Similarity	NPC162484
0.8048	Intermediate Similarity	NPC209769
0.8048	Intermediate Similarity	NPC473181
0.8	Intermediate Similarity	NPC131885
0.799	Intermediate Similarity	NPC70259
0.7963	Intermediate Similarity	NPC288987
0.7955	Intermediate Similarity	NPC473185
0.7952	Intermediate Similarity	NPC193777
0.7941	Intermediate Similarity	NPC205934
0.7941	Intermediate Similarity	NPC43787
0.794	Intermediate Similarity	NPC84478
0.7934	Intermediate Similarity	NPC94157
0.7928	Intermediate Similarity	NPC260434
0.7919	Intermediate Similarity	NPC194740
0.7917	Intermediate Similarity	NPC473041
0.7892	Intermediate Similarity	NPC49547
0.7873	Intermediate Similarity	NPC74575
0.785	Intermediate Similarity	NPC473180
0.7848	Intermediate Similarity	NPC475253
0.7847	Intermediate Similarity	NPC475112
0.7847	Intermediate Similarity	NPC475085
0.7847	Intermediate Similarity	NPC291535
0.7839	Intermediate Similarity	NPC89549
0.7838	Intermediate Similarity	NPC471762
0.7834	Intermediate Similarity	NPC303658
0.7822	Intermediate Similarity	NPC34770
0.782	Intermediate Similarity	NPC476106
0.7818	Intermediate Similarity	NPC122436
0.7799	Intermediate Similarity	NPC267423
0.7798	Intermediate Similarity	NPC298436
0.7793	Intermediate Similarity	NPC201697
0.7778	Intermediate Similarity	NPC473182
0.7763	Intermediate Similarity	NPC132642
0.7762	Intermediate Similarity	NPC199277
0.7762	Intermediate Similarity	NPC135887
0.7742	Intermediate Similarity	NPC148183
0.7742	Intermediate Similarity	NPC152768
0.7738	Intermediate Similarity	NPC205372
0.7725	Intermediate Similarity	NPC134848
0.7714	Intermediate Similarity	NPC476044
0.7713	Intermediate Similarity	NPC257851
0.7713	Intermediate Similarity	NPC140296
0.7711	Intermediate Similarity	NPC212535
0.7706	Intermediate Similarity	NPC305984
0.7703	Intermediate Similarity	NPC21638
0.7696	Intermediate Similarity	NPC16066
0.7685	Intermediate Similarity	NPC48353
0.7685	Intermediate Similarity	NPC264176
0.7679	Intermediate Similarity	NPC66777
0.7675	Intermediate Similarity	NPC473183
0.7674	Intermediate Similarity	NPC269367
0.7674	Intermediate Similarity	NPC471304
0.7671	Intermediate Similarity	NPC96321
0.7667	Intermediate Similarity	NPC329747
0.7665	Intermediate Similarity	NPC473184
0.7656	Intermediate Similarity	NPC306376
0.7647	Intermediate Similarity	NPC60621
0.7635	Intermediate Similarity	NPC94943
0.7634	Intermediate Similarity	NPC478078
0.7632	Intermediate Similarity	NPC470017
0.7629	Intermediate Similarity	NPC208522
0.7628	Intermediate Similarity	NPC325297
0.7624	Intermediate Similarity	NPC176127
0.7623	Intermediate Similarity	NPC97746
0.7621	Intermediate Similarity	NPC329631
0.7619	Intermediate Similarity	NPC166712
0.7617	Intermediate Similarity	NPC183777
0.7607	Intermediate Similarity	NPC270515
0.7606	Intermediate Similarity	NPC132539
0.7598	Intermediate Similarity	NPC235685
0.7593	Intermediate Similarity	NPC470020
0.7589	Intermediate Similarity	NPC202503
0.7586	Intermediate Similarity	NPC190007
0.7586	Intermediate Similarity	NPC208364
0.7586	Intermediate Similarity	NPC160100
0.7565	Intermediate Similarity	NPC101350
0.7563	Intermediate Similarity	NPC53534
0.7559	Intermediate Similarity	NPC476138
0.7559	Intermediate Similarity	NPC245816
0.7556	Intermediate Similarity	NPC157931
0.7548	Intermediate Similarity	NPC230403
0.7533	Intermediate Similarity	NPC217176
0.7524	Intermediate Similarity	NPC153042
0.7523	Intermediate Similarity	NPC323969
0.7522	Intermediate Similarity	NPC472061
0.7521	Intermediate Similarity	NPC58209
0.7521	Intermediate Similarity	NPC152620
0.75	Intermediate Similarity	NPC148889
0.75	Intermediate Similarity	NPC165964
0.75	Intermediate Similarity	NPC475910
0.75	Intermediate Similarity	NPC118511
0.7489	Intermediate Similarity	NPC89508
0.7475	Intermediate Similarity	NPC88363
0.7474	Intermediate Similarity	NPC76982
0.7469	Intermediate Similarity	NPC185197
0.7467	Intermediate Similarity	NPC473105
0.7465	Intermediate Similarity	NPC232727
0.7465	Intermediate Similarity	NPC185782
0.7458	Intermediate Similarity	NPC173250
0.7449	Intermediate Similarity	NPC132385
0.7446	Intermediate Similarity	NPC470022
0.7446	Intermediate Similarity	NPC184680
0.7444	Intermediate Similarity	NPC472099
0.7443	Intermediate Similarity	NPC12344
0.7443	Intermediate Similarity	NPC26679
0.7442	Intermediate Similarity	NPC285558
0.7426	Intermediate Similarity	NPC203373
0.7424	Intermediate Similarity	NPC132329
0.7421	Intermediate Similarity	NPC330009
0.7418	Intermediate Similarity	NPC315634
0.7418	Intermediate Similarity	NPC100734
0.7418	Intermediate Similarity	NPC88923
0.7414	Intermediate Similarity	NPC470785
0.7409	Intermediate Similarity	NPC476287
0.7395	Intermediate Similarity	NPC67401
0.7395	Intermediate Similarity	NPC223427
0.7395	Intermediate Similarity	NPC165599
0.7387	Intermediate Similarity	NPC312645
0.7382	Intermediate Similarity	NPC41501
0.738	Intermediate Similarity	NPC477112
0.7379	Intermediate Similarity	NPC42591
0.7373	Intermediate Similarity	NPC475666
0.7371	Intermediate Similarity	NPC15801
0.7368	Intermediate Similarity	NPC311906
0.7364	Intermediate Similarity	NPC474428
0.7364	Intermediate Similarity	NPC118940
0.7355	Intermediate Similarity	NPC284685
0.7348	Intermediate Similarity	NPC475720
0.7348	Intermediate Similarity	NPC474192
0.7346	Intermediate Similarity	NPC276517
0.7342	Intermediate Similarity	NPC170114
0.7339	Intermediate Similarity	NPC470784
0.7336	Intermediate Similarity	NPC19872
0.7333	Intermediate Similarity	NPC477532
0.7331	Intermediate Similarity	NPC81939
0.733	Intermediate Similarity	NPC469592
0.733	Intermediate Similarity	NPC471080
0.7314	Intermediate Similarity	NPC258048
0.7311	Intermediate Similarity	NPC251090
0.7308	Intermediate Similarity	NPC168922
0.7304	Intermediate Similarity	NPC72980
0.7303	Intermediate Similarity	NPC303374
0.7297	Intermediate Similarity	NPC470549

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 NPC208084 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	693
0.2-0.3	991
0.3-0.4	1483
0.4-0.5	2982
0.5-0.6	1881
0.6-0.7	648
0.7-0.8	91
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD6160	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5632	Approved
0.7778	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD4429	Discontinued
0.7723	Intermediate Similarity	NPD5479	Discontinued
0.7706	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6242	Discontinued
0.765	Intermediate Similarity	NPD5482	Discontinued
0.7621	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD5658	Approved
0.7534	Intermediate Similarity	NPD3257	Approved
0.7533	Intermediate Similarity	NPD1505	Phase 2
0.7489	Intermediate Similarity	NPD5022	Discontinued
0.7489	Intermediate Similarity	NPD3945	Discontinued
0.7488	Intermediate Similarity	NPD3003	Approved
0.7478	Intermediate Similarity	NPD3259	Approved
0.7478	Intermediate Similarity	NPD3006	Discontinued
0.7476	Intermediate Similarity	NPD5512	Phase 3
0.7456	Intermediate Similarity	NPD1867	Approved
0.7454	Intermediate Similarity	NPD5429	Discontinued
0.7432	Intermediate Similarity	NPD7395	Discontinued
0.7425	Intermediate Similarity	NPD6790	Phase 1
0.7418	Intermediate Similarity	NPD7803	Approved
0.7412	Intermediate Similarity	NPD4952	Phase 3
0.7399	Intermediate Similarity	NPD3258	Approved
0.7397	Intermediate Similarity	NPD5416	Discontinued
0.7371	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5003	Discontinued
0.7355	Intermediate Similarity	NPD7955	Approved
0.7355	Intermediate Similarity	NPD7956	Approved
0.7348	Intermediate Similarity	NPD3746	Discontinued
0.7342	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7853	Phase 2
0.7328	Intermediate Similarity	NPD8363	Approved
0.7328	Intermediate Similarity	NPD8364	Approved
0.7316	Intermediate Similarity	NPD4373	Phase 2
0.7304	Intermediate Similarity	NPD6962	Phase 2
0.7304	Intermediate Similarity	NPD1467	Approved
0.7304	Intermediate Similarity	NPD1466	Phase 3
0.7301	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5902	Approved
0.7297	Intermediate Similarity	NPD5903	Approved
0.729	Intermediate Similarity	NPD1768	Approved
0.728	Intermediate Similarity	NPD3986	Discontinued
0.7276	Intermediate Similarity	NPD5450	Discontinued
0.7273	Intermediate Similarity	NPD4885	Approved
0.7269	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7708	Approved
0.7249	Intermediate Similarity	NPD4328	Approved
0.7249	Intermediate Similarity	NPD7994	Phase 2
0.7246	Intermediate Similarity	NPD6716	Phase 1
0.7238	Intermediate Similarity	NPD2564	Approved
0.7238	Intermediate Similarity	NPD2565	Phase 2
0.7232	Intermediate Similarity	NPD5164	Discontinued
0.7222	Intermediate Similarity	NPD4368	Phase 2
0.7217	Intermediate Similarity	NPD1038	Approved
0.7217	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2778	Approved
0.7183	Intermediate Similarity	NPD4418	Discontinued
0.7162	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4502	Phase 2
0.7154	Intermediate Similarity	NPD8467	Approved
0.7154	Intermediate Similarity	NPD8465	Approved
0.7154	Intermediate Similarity	NPD8466	Approved
0.7154	Intermediate Similarity	NPD8429	Approved
0.7154	Intermediate Similarity	NPD8427	Approved
0.7154	Intermediate Similarity	NPD8428	Approved
0.7149	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD2951	Discontinued
0.7123	Intermediate Similarity	NPD5901	Discontinued
0.7119	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5612	Discontinued
0.711	Intermediate Similarity	NPD2779	Approved
0.7109	Intermediate Similarity	NPD8459	Approved
0.7109	Intermediate Similarity	NPD8460	Approved
0.7103	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5488	Discontinued
0.7081	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7180	Phase 3
0.7059	Intermediate Similarity	NPD7417	Discontinued
0.7059	Intermediate Similarity	NPD7452	Approved
0.7059	Intermediate Similarity	NPD1392	Approved
0.7059	Intermediate Similarity	NPD7222	Phase 2
0.7059	Intermediate Similarity	NPD7453	Approved
0.7048	Intermediate Similarity	NPD6985	Discontinued
0.7043	Intermediate Similarity	NPD8426	Approved
0.7043	Intermediate Similarity	NPD8425	Approved
0.7042	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5913	Phase 3
0.7033	Intermediate Similarity	NPD8091	Phase 3
0.7018	Intermediate Similarity	NPD6770	Approved
0.7014	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5256	Discontinued
0.7004	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD4506	Discontinued
0.6996	Remote Similarity	NPD5559	Phase 2
0.6991	Remote Similarity	NPD6550	Discontinued
0.6983	Remote Similarity	NPD8358	Approved
0.6983	Remote Similarity	NPD7603	Discontinued
0.6972	Remote Similarity	NPD3825	Phase 3
0.6971	Remote Similarity	NPD3920	Phase 2
0.6968	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5924	Discontinued
0.6962	Remote Similarity	NPD3250	Phase 1
0.6958	Remote Similarity	NPD6517	Phase 3
0.6955	Remote Similarity	NPD4558	Phase 2
0.6943	Remote Similarity	NPD7194	Discontinued
0.6943	Remote Similarity	NPD6974	Phase 3
0.6941	Remote Similarity	NPD484	Approved
0.6937	Remote Similarity	NPD8403	Phase 1
0.6936	Remote Similarity	NPD7688	Phase 1
0.6933	Remote Similarity	NPD5805	Approved
0.6929	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD6995	Phase 1
0.6923	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5293	Phase 2
0.6913	Remote Similarity	NPD5850	Phase 3
0.6911	Remote Similarity	NPD8463	Approved
0.6908	Remote Similarity	NPD6531	Approved
0.6908	Remote Similarity	NPD6530	Approved
0.6903	Remote Similarity	NPD5866	Approved
0.6903	Remote Similarity	NPD7069	Discontinued
0.6892	Remote Similarity	NPD6456	Discontinued
0.6889	Remote Similarity	NPD3392	Approved
0.6878	Remote Similarity	NPD7558	Phase 2
0.6875	Remote Similarity	NPD7467	Discontinued
0.6875	Remote Similarity	NPD2916	Discontinued
0.687	Remote Similarity	NPD3875	Discontinued
0.6866	Remote Similarity	NPD6590	Discontinued
0.6864	Remote Similarity	NPD3289	Phase 3
0.6864	Remote Similarity	NPD3290	Approved
0.6858	Remote Similarity	NPD5939	Approved
0.6858	Remote Similarity	NPD5936	Approved
0.6858	Remote Similarity	NPD5067	Phase 2
0.6858	Remote Similarity	NPD5066	Phase 2
0.6847	Remote Similarity	NPD2920	Discontinued
0.6847	Remote Similarity	NPD6176	Phase 1
0.6842	Remote Similarity	NPD5532	Phase 2
0.6842	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6228	Discontinued
0.6826	Remote Similarity	NPD3354	Phase 2
0.682	Remote Similarity	NPD4454	Phase 2
0.6818	Remote Similarity	NPD2177	Approved
0.6818	Remote Similarity	NPD2176	Approved
0.6818	Remote Similarity	NPD2175	Phase 3
0.6816	Remote Similarity	NPD3947	Discontinued
0.6816	Remote Similarity	NPD8102	Discontinued
0.6816	Remote Similarity	NPD4795	Phase 2
0.6804	Remote Similarity	NPD6988	Phase 1
0.68	Remote Similarity	NPD2510	Approved
0.68	Remote Similarity	NPD2509	Approved
0.68	Remote Similarity	NPD6376	Discontinued
0.6798	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD6961	Discontinued
0.6787	Remote Similarity	NPD4501	Approved
0.6787	Remote Similarity	NPD4500	Approved
0.6787	Remote Similarity	NPD1739	Approved
0.6787	Remote Similarity	NPD1740	Approved
0.6786	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6775	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3263	Phase 3
0.6763	Remote Similarity	NPD1325	Approved
0.6763	Remote Similarity	NPD1326	Approved
0.6757	Remote Similarity	NPD4511	Phase 1
0.6754	Remote Similarity	NPD8489	Phase 1
0.6753	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4948	Discontinued
0.6741	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6494	Phase 2
0.6726	Remote Similarity	NPD2187	Approved
0.6726	Remote Similarity	NPD2189	Approved
0.6723	Remote Similarity	NPD3925	Approved
0.6722	Remote Similarity	NPD946	Discontinued
0.6719	Remote Similarity	NPD5399	Discovery
0.6713	Remote Similarity	NPD2792	Approved
0.6711	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6245	Phase 2
0.6711	Remote Similarity	NPD7470	Discontinued
0.6707	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7426	Phase 1
0.6695	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4724	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