NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	227.06
Volume:	226.647
LogP:	2.638
LogD:	2.421
LogS:	-4.377
# Rotatable Bonds:	1
TPSA:	73.32
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	2.455
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.141
MDCK Permeability:	5.454936399473809e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	93.96853637695312%
Volume Distribution (VD):	0.67
Pgp-substrate:	3.6671862602233887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.318
CYP2C9-substrate:	0.823
CYP2D6-inhibitor:	0.731
CYP2D6-substrate:	0.505
CYP3A4-inhibitor:	0.648
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	7.705
Half-life (T1/2):	0.776

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.731
AMES Toxicity:	0.237
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.874
Carcinogencity:	0.052
Eye Corrosion:	0.162
Eye Irritation:	0.984
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC294375

Natural Product ID:	NPC294375
*Common Name:**	Clausine-Z
IUPAC Name:	1,6-dihydroxy-9H-carbazole-3-carbaldehyde
Synonyms:	Clausine-Z
Standard InCHIKey:	FKDULSCBYNXNMP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H9NO3/c15-6-7-3-10-9-5-8(16)1-2-11(9)14-13(10)12(17)4-7/h1-6,14,16-17H
SMILES:	O=Cc1cc(O)c2c(c1)c1cc(O)ccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1927323
PubChem CID:	11436094
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
NPO18135	Clausena vestita	Species	Rutaceae	Eukaryota	whole plants	Yunnan Province, China	2008-JAN	PMID[22093759]
NPO18135	Clausena vestita	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	135000.0	nM	PMID[476734]

☑ 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 NPC294375 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	537
0.1-0.2	3615
0.2-0.3	13449
0.3-0.4	6808
0.4-0.5	13749
0.5-0.6	2537
0.6-0.7	1687
0.7-0.8	269
0.8-0.85	28
0.85-0.9	12
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9786	High Similarity	NPC283117
0.9337	High Similarity	NPC293151
0.9235	High Similarity	NPC118228
0.9109	High Similarity	NPC179287
0.9082	High Similarity	NPC9894
0.8985	High Similarity	NPC187501
0.8905	High Similarity	NPC184408
0.8873	High Similarity	NPC51388
0.8827	High Similarity	NPC45190
0.8768	High Similarity	NPC208084
0.8737	High Similarity	NPC86834
0.8737	High Similarity	NPC210828
0.8708	High Similarity	NPC474701
0.8706	High Similarity	NPC39500
0.8634	High Similarity	NPC225279
0.8607	High Similarity	NPC23294
0.8557	High Similarity	NPC303951
0.8543	High Similarity	NPC300156
0.8458	Intermediate Similarity	NPC39679
0.8436	Intermediate Similarity	NPC274640
0.8404	Intermediate Similarity	NPC88363
0.8373	Intermediate Similarity	NPC144452
0.8357	Intermediate Similarity	NPC247803
0.8357	Intermediate Similarity	NPC46561
0.8357	Intermediate Similarity	NPC477112
0.8326	Intermediate Similarity	NPC39370
0.8317	Intermediate Similarity	NPC249583
0.8317	Intermediate Similarity	NPC321428
0.8278	Intermediate Similarity	NPC150239
0.8244	Intermediate Similarity	NPC87413
0.8241	Intermediate Similarity	NPC128823
0.8233	Intermediate Similarity	NPC473186
0.8227	Intermediate Similarity	NPC270918
0.8223	Intermediate Similarity	NPC276517
0.8186	Intermediate Similarity	NPC474688
0.8186	Intermediate Similarity	NPC171787
0.8173	Intermediate Similarity	NPC3207
0.8165	Intermediate Similarity	NPC6786
0.8136	Intermediate Similarity	NPC475844
0.8116	Intermediate Similarity	NPC308137
0.8116	Intermediate Similarity	NPC310211
0.8079	Intermediate Similarity	NPC476098
0.8073	Intermediate Similarity	NPC478032
0.8061	Intermediate Similarity	NPC246700
0.8058	Intermediate Similarity	NPC325297
0.8051	Intermediate Similarity	NPC160381
0.8049	Intermediate Similarity	NPC4687
0.8029	Intermediate Similarity	NPC219087
0.802	Intermediate Similarity	NPC213308
0.7981	Intermediate Similarity	NPC280799
0.797	Intermediate Similarity	NPC242928
0.7934	Intermediate Similarity	NPC174760
0.7934	Intermediate Similarity	NPC276657
0.7879	Intermediate Similarity	NPC128751
0.7871	Intermediate Similarity	NPC153042
0.7843	Intermediate Similarity	NPC45459
0.7843	Intermediate Similarity	NPC315491
0.7839	Intermediate Similarity	NPC106833
0.7839	Intermediate Similarity	NPC144381
0.7839	Intermediate Similarity	NPC469497
0.783	Intermediate Similarity	NPC469928
0.7816	Intermediate Similarity	NPC165599
0.7816	Intermediate Similarity	NPC134848
0.7814	Intermediate Similarity	NPC198503
0.7811	Intermediate Similarity	NPC230403
0.7806	Intermediate Similarity	NPC212535
0.7789	Intermediate Similarity	NPC221873
0.7788	Intermediate Similarity	NPC183777
0.7788	Intermediate Similarity	NPC244741
0.7788	Intermediate Similarity	NPC53344
0.7788	Intermediate Similarity	NPC88008
0.7783	Intermediate Similarity	NPC141454
0.7783	Intermediate Similarity	NPC116238
0.7758	Intermediate Similarity	NPC15801
0.7754	Intermediate Similarity	NPC76982
0.7745	Intermediate Similarity	NPC306376
0.7727	Intermediate Similarity	NPC94943
0.772	Intermediate Similarity	NPC474409
0.771	Intermediate Similarity	NPC169402
0.7678	Intermediate Similarity	NPC309845
0.7677	Intermediate Similarity	NPC190007
0.7665	Intermediate Similarity	NPC474798
0.7662	Intermediate Similarity	NPC83111
0.7661	Intermediate Similarity	NPC205372
0.7658	Intermediate Similarity	NPC132329
0.7639	Intermediate Similarity	NPC74360
0.7638	Intermediate Similarity	NPC241025
0.7634	Intermediate Similarity	NPC473187
0.7632	Intermediate Similarity	NPC160898
0.7621	Intermediate Similarity	NPC280714
0.7619	Intermediate Similarity	NPC473188
0.7619	Intermediate Similarity	NPC193777
0.761	Intermediate Similarity	NPC156704
0.7606	Intermediate Similarity	NPC12344
0.7604	Intermediate Similarity	NPC132642
0.7598	Intermediate Similarity	NPC131017
0.759	Intermediate Similarity	NPC303225
0.7586	Intermediate Similarity	NPC99666
0.7581	Intermediate Similarity	NPC477110
0.7573	Intermediate Similarity	NPC192315
0.757	Intermediate Similarity	NPC89508
0.7558	Intermediate Similarity	NPC473179
0.755	Intermediate Similarity	NPC314002
0.7547	Intermediate Similarity	NPC209769
0.7546	Intermediate Similarity	NPC314552
0.7542	Intermediate Similarity	NPC89549
0.7538	Intermediate Similarity	NPC220765
0.7536	Intermediate Similarity	NPC476167
0.7524	Intermediate Similarity	NPC243834
0.7524	Intermediate Similarity	NPC70956
0.7512	Intermediate Similarity	NPC5145
0.7512	Intermediate Similarity	NPC264285
0.7512	Intermediate Similarity	NPC194040
0.75	Intermediate Similarity	NPC204717
0.75	Intermediate Similarity	NPC207686
0.75	Intermediate Similarity	NPC477111
0.7488	Intermediate Similarity	NPC31700
0.7488	Intermediate Similarity	NPC472284
0.7488	Intermediate Similarity	NPC477113
0.7478	Intermediate Similarity	NPC477549
0.7468	Intermediate Similarity	NPC473800
0.7465	Intermediate Similarity	NPC312645
0.7465	Intermediate Similarity	NPC472285
0.7463	Intermediate Similarity	NPC475190
0.7442	Intermediate Similarity	NPC94157
0.744	Intermediate Similarity	NPC77555
0.744	Intermediate Similarity	NPC90229
0.743	Intermediate Similarity	NPC471304
0.7429	Intermediate Similarity	NPC135887
0.7429	Intermediate Similarity	NPC199277
0.7426	Intermediate Similarity	NPC171171
0.7424	Intermediate Similarity	NPC184964
0.7419	Intermediate Similarity	NPC330009
0.7416	Intermediate Similarity	NPC249040
0.7399	Intermediate Similarity	NPC478078
0.7399	Intermediate Similarity	NPC473185
0.7397	Intermediate Similarity	NPC288987
0.7393	Intermediate Similarity	NPC223427
0.7387	Intermediate Similarity	NPC72980
0.7363	Intermediate Similarity	NPC176127
0.7361	Intermediate Similarity	NPC48353
0.7358	Intermediate Similarity	NPC132539
0.7354	Intermediate Similarity	NPC470018
0.7352	Intermediate Similarity	NPC131885
0.7352	Intermediate Similarity	NPC96321
0.7349	Intermediate Similarity	NPC199667
0.7339	Intermediate Similarity	NPC322064
0.7339	Intermediate Similarity	NPC74969
0.7328	Intermediate Similarity	NPC208522
0.7321	Intermediate Similarity	NPC157931
0.7315	Intermediate Similarity	NPC82370
0.7313	Intermediate Similarity	NPC314394
0.7311	Intermediate Similarity	NPC162484
0.7308	Intermediate Similarity	NPC251090
0.7302	Intermediate Similarity	NPC473181
0.7297	Intermediate Similarity	NPC16352
0.7294	Intermediate Similarity	NPC16066
0.7281	Intermediate Similarity	NPC473180
0.7281	Intermediate Similarity	NPC182222
0.7277	Intermediate Similarity	NPC470930
0.7269	Intermediate Similarity	NPC474192
0.7269	Intermediate Similarity	NPC475720
0.7264	Intermediate Similarity	NPC475085
0.7264	Intermediate Similarity	NPC291535
0.7264	Intermediate Similarity	NPC475112
0.7248	Intermediate Similarity	NPC250448
0.7244	Intermediate Similarity	NPC140296
0.7244	Intermediate Similarity	NPC257851
0.7243	Intermediate Similarity	NPC472286
0.7243	Intermediate Similarity	NPC472287
0.7241	Intermediate Similarity	NPC473312
0.724	Intermediate Similarity	NPC141353
0.7233	Intermediate Similarity	NPC154339
0.7227	Intermediate Similarity	NPC27041
0.7222	Intermediate Similarity	NPC178858
0.722	Intermediate Similarity	NPC206186
0.722	Intermediate Similarity	NPC220851
0.722	Intermediate Similarity	NPC46580
0.7212	Intermediate Similarity	NPC194740
0.7205	Intermediate Similarity	NPC97902
0.7203	Intermediate Similarity	NPC165964
0.7196	Intermediate Similarity	NPC475070
0.7193	Intermediate Similarity	NPC49547
0.7191	Intermediate Similarity	NPC218388
0.7173	Intermediate Similarity	NPC67401
0.7168	Intermediate Similarity	NPC74575
0.7163	Intermediate Similarity	NPC67551
0.7163	Intermediate Similarity	NPC175602
0.7163	Intermediate Similarity	NPC476106
0.7162	Intermediate Similarity	NPC473182
0.7162	Intermediate Similarity	NPC284888
0.7156	Intermediate Similarity	NPC131887
0.7156	Intermediate Similarity	NPC97746
0.7155	Intermediate Similarity	NPC475816
0.7143	Intermediate Similarity	NPC473183
0.7137	Intermediate Similarity	NPC74619
0.7136	Intermediate Similarity	NPC471944
0.7136	Intermediate Similarity	NPC278434
0.713	Intermediate Similarity	NPC472099
0.7129	Intermediate Similarity	NPC267343

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 NPC294375 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	680
0.2-0.3	970
0.3-0.4	1570
0.4-0.5	3122
0.5-0.6	1829
0.6-0.7	576
0.7-0.8	55
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
0.8286	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3746	Discontinued
0.7843	Intermediate Similarity	NPD484	Approved
0.7692	Intermediate Similarity	NPD5901	Discontinued
0.7652	Intermediate Similarity	NPD3986	Discontinued
0.7546	Intermediate Similarity	NPD5164	Discontinued
0.7467	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6456	Discontinued
0.7443	Intermediate Similarity	NPD6242	Discontinued
0.744	Intermediate Similarity	NPD5003	Discontinued
0.7432	Intermediate Similarity	NPD7603	Discontinued
0.7399	Intermediate Similarity	NPD4845	Discontinued
0.7397	Intermediate Similarity	NPD3258	Approved
0.7395	Intermediate Similarity	NPD5416	Discontinued
0.7395	Intermediate Similarity	NPD5936	Approved
0.7395	Intermediate Similarity	NPD5939	Approved
0.7368	Intermediate Similarity	NPD2176	Approved
0.7368	Intermediate Similarity	NPD2175	Phase 3
0.7368	Intermediate Similarity	NPD2177	Approved
0.7358	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD6376	Discontinued
0.7328	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2565	Phase 2
0.7317	Intermediate Similarity	NPD2564	Approved
0.7294	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3257	Approved
0.7291	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5632	Approved
0.7273	Intermediate Similarity	NPD4429	Discontinued
0.7259	Intermediate Similarity	NPD1326	Approved
0.7259	Intermediate Similarity	NPD1325	Approved
0.7257	Intermediate Similarity	NPD5479	Discontinued
0.7256	Intermediate Similarity	NPD2916	Discontinued
0.722	Intermediate Similarity	NPD4948	Discontinued
0.7209	Intermediate Similarity	NPD6290	Phase 2
0.7208	Intermediate Similarity	NPD2844	Phase 3
0.7182	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5612	Discontinued
0.7181	Intermediate Similarity	NPD5022	Discontinued
0.7169	Intermediate Similarity	NPD3243	Approved
0.7168	Intermediate Similarity	NPD4328	Approved
0.7149	Intermediate Similarity	NPD1466	Phase 3
0.7149	Intermediate Similarity	NPD1467	Approved
0.7136	Intermediate Similarity	NPD4511	Phase 1
0.7129	Intermediate Similarity	NPD1038	Approved
0.7123	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7395	Discontinued
0.7117	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7948	Phase 1
0.7095	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6159	Phase 2
0.7078	Intermediate Similarity	NPD4502	Phase 2
0.7062	Intermediate Similarity	NPD5512	Phase 3
0.7059	Intermediate Similarity	NPD3809	Discontinued
0.7056	Intermediate Similarity	NPD2951	Discontinued
0.7043	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD8395	Approved
0.7042	Intermediate Similarity	NPD8396	Approved
0.7037	Intermediate Similarity	NPD6530	Approved
0.7037	Intermediate Similarity	NPD6531	Approved
0.7031	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3945	Discontinued
0.7013	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1505	Phase 2
0.7	Intermediate Similarity	NPD1867	Approved
0.6982	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7453	Approved
0.6972	Remote Similarity	NPD7222	Phase 2
0.6972	Remote Similarity	NPD5429	Discontinued
0.6972	Remote Similarity	NPD7452	Approved
0.6967	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3006	Discontinued
0.6944	Remote Similarity	NPD2779	Approved
0.6938	Remote Similarity	NPD1534	Approved
0.6927	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3003	Approved
0.6917	Remote Similarity	NPD5482	Discontinued
0.6916	Remote Similarity	NPD6995	Phase 1
0.6912	Remote Similarity	NPD2920	Discontinued
0.6897	Remote Similarity	NPD9690	Approved
0.6881	Remote Similarity	NPD5426	Phase 3
0.6878	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6716	Phase 1
0.6875	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5913	Phase 3
0.6864	Remote Similarity	NPD4561	Discontinued
0.6864	Remote Similarity	NPD5658	Approved
0.6862	Remote Similarity	NPD5488	Discontinued
0.6847	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8363	Approved
0.684	Remote Similarity	NPD8364	Approved
0.6837	Remote Similarity	NPD2727	Phase 2
0.6835	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD8463	Approved
0.6827	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3330	Phase 1
0.6814	Remote Similarity	NPD482	Approved
0.6814	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3354	Phase 2
0.6812	Remote Similarity	NPD3178	Discontinued
0.681	Remote Similarity	NPD2383	Phase 1
0.681	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7853	Phase 2
0.6808	Remote Similarity	NPD9695	Approved
0.6806	Remote Similarity	NPD2778	Approved
0.6804	Remote Similarity	NPD6987	Phase 1
0.6802	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4373	Phase 2
0.6786	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD9705	Discontinued
0.6784	Remote Similarity	NPD112	Approved
0.6784	Remote Similarity	NPD4312	Approved
0.6783	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.678	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4418	Discontinued
0.6774	Remote Similarity	NPD4600	Approved
0.6774	Remote Similarity	NPD4601	Approved
0.6773	Remote Similarity	NPD7001	Phase 3
0.6771	Remote Similarity	NPD7470	Discontinued
0.6767	Remote Similarity	NPD5559	Phase 2
0.6763	Remote Similarity	NPD5445	Approved
0.6763	Remote Similarity	NPD9510	Approved
0.6761	Remote Similarity	NPD7708	Approved
0.6758	Remote Similarity	NPD7181	Phase 3
0.6757	Remote Similarity	NPD4506	Discontinued
0.6756	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4885	Approved
0.6746	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4952	Phase 3
0.6736	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4558	Phase 2
0.6728	Remote Similarity	NPD1768	Approved
0.6726	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7726	Phase 1
0.6724	Remote Similarity	NPD3259	Approved
0.6711	Remote Similarity	NPD3875	Discontinued
0.6711	Remote Similarity	NPD6770	Approved
0.6699	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2092	Phase 2
0.6699	Remote Similarity	NPD2095	Phase 2
0.6699	Remote Similarity	NPD2094	Phase 2
0.6698	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7417	Discontinued
0.6694	Remote Similarity	NPD8358	Approved
0.6682	Remote Similarity	NPD6176	Phase 1
0.6681	Remote Similarity	NPD4897	Phase 2
0.6681	Remote Similarity	NPD5903	Approved
0.6681	Remote Similarity	NPD5902	Approved
0.668	Remote Similarity	NPD3962	Phase 2
0.668	Remote Similarity	NPD3959	Phase 2
0.668	Remote Similarity	NPD8467	Approved
0.668	Remote Similarity	NPD8091	Phase 3
0.668	Remote Similarity	NPD8428	Approved
0.668	Remote Similarity	NPD8429	Approved
0.668	Remote Similarity	NPD8427	Approved
0.668	Remote Similarity	NPD8466	Approved
0.668	Remote Similarity	NPD8465	Approved
0.6667	Remote Similarity	NPD8097	Phase 3
0.6667	Remote Similarity	NPD2096	Phase 2
0.6667	Remote Similarity	NPD8093	Discontinued
0.6667	Remote Similarity	NPD8096	Phase 3
0.6667	Remote Similarity	NPD7878	Phase 2
0.6667	Remote Similarity	NPD1592	Phase 3
0.6667	Remote Similarity	NPD2091	Phase 2
0.6667	Remote Similarity	NPD8102	Discontinued
0.6654	Remote Similarity	NPD8349	Phase 1
0.6653	Remote Similarity	NPD7803	Approved
0.6652	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7994	Phase 2
0.6652	Remote Similarity	NPD3947	Discontinued
0.6652	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3814	Phase 1
0.6651	Remote Similarity	NPD3825	Phase 3
0.6651	Remote Similarity	NPD802	Phase 2
0.6641	Remote Similarity	NPD8460	Approved
0.6641	Remote Similarity	NPD8459	Approved
0.664	Remote Similarity	NPD5399	Discovery
0.6639	Remote Similarity	NPD5805	Approved
0.6639	Remote Similarity	NPD4368	Phase 2
0.6638	Remote Similarity	NPD7688	Phase 1
0.6638	Remote Similarity	NPD6962	Phase 2
0.6637	Remote Similarity	NPD2510	Approved
0.6637	Remote Similarity	NPD2509	Approved
0.6636	Remote Similarity	NPD6162	Approved
0.6636	Remote Similarity	NPD6161	Approved
0.6635	Remote Similarity	NPD2762	Phase 2

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