NPASS Compound

Structure

CID198503 OpenBabel06191715582D 23 26 0 0 0 0 0 0 0 0999 V2000 -1.0167 -0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5087 -1.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3623 0.7185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8751 1.4527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0361 1.9373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -0.9693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8387 -1.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 1.9380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0358 -0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 1.9383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 1.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8749 0.4832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1965 1.4530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6781 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5179 1.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1963 0.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5178 0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 -0.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3572 -0.0008 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5692 1.1545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7139 -0.0014 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 19 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 21 2 0 0 0 0 11 18 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 16 2 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.12
Volume:	319.23
LogP:	4.948
LogD:	4.24
LogS:	-4.701
# Rotatable Bonds:	2
TPSA:	51.32
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	2.904
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.954
MDCK Permeability:	1.645717566134408e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.302
Plasma Protein Binding (PPB):	96.74933624267578%
Volume Distribution (VD):	0.572
Pgp-substrate:	1.7080836296081543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.925
CYP2C19-substrate:	0.44
CYP2C9-inhibitor:	0.818
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.906
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.834
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	2.546
Half-life (T1/2):	0.178

ADMET: Toxicity

hERG Blockers:	0.206
Human Hepatotoxicity (H-HT):	0.88
Drug-inuced Liver Injury (DILI):	0.842
AMES Toxicity:	0.832
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.428
Carcinogencity:	0.903
Eye Corrosion:	0.005
Eye Irritation:	0.363
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC198503

Natural Product ID:	NPC198503
*Common Name:**	7-Methoxymurrayanine
IUPAC Name:	9-methoxy-3,3-dimethyl-11H-pyrano[3,2-a]carbazole-5-carbaldehyde
Synonyms:	7-Methoxymurrayanine
Standard InCHIKey:	ULTYRPCVVWZHPO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H17NO3/c1-19(2)7-6-14-17-15(8-11(10-21)18(14)23-19)13-5-4-12(22-3)9-16(13)20-17/h4-10,20H,1-3H3
SMILES:	O=Cc1cc2c(c3c1OC(C)(C)C=C3)[nH]c1c2ccc(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689803
PubChem CID:	14760665
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	>	200000.0	nM	PMID[508021]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	200000.0	nM	PMID[508021]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	200000.0	nM	PMID[508021]

☑ 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 NPC198503 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	522
0.1-0.2	3176
0.2-0.3	12911
0.3-0.4	4049
0.4-0.5	12829
0.5-0.6	7114
0.6-0.7	1598
0.7-0.8	416
0.8-0.85	39
0.85-0.9	28
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC308137
0.9592	High Similarity	NPC310211
0.9453	High Similarity	NPC150239
0.9353	High Similarity	NPC247803
0.9353	High Similarity	NPC46561
0.9337	High Similarity	NPC249583
0.9286	High Similarity	NPC6786
0.9208	High Similarity	NPC169402
0.9204	High Similarity	NPC116238
0.9055	High Similarity	NPC23294
0.9045	High Similarity	NPC4687
0.9005	High Similarity	NPC303951
0.8981	High Similarity	NPC174760
0.8929	High Similarity	NPC72211
0.8905	High Similarity	NPC210828
0.8905	High Similarity	NPC86834
0.8867	High Similarity	NPC87413
0.8846	High Similarity	NPC280799
0.8841	High Similarity	NPC208084
0.8827	High Similarity	NPC70259
0.8806	High Similarity	NPC45190
0.8786	High Similarity	NPC3207
0.8776	High Similarity	NPC43787
0.8776	High Similarity	NPC205934
0.8706	High Similarity	NPC162484
0.8704	High Similarity	NPC473187
0.8657	High Similarity	NPC475112
0.8657	High Similarity	NPC475085
0.8657	High Similarity	NPC291535
0.8632	High Similarity	NPC179287
0.8627	High Similarity	NPC39679
0.8621	High Similarity	NPC476106
0.8531	High Similarity	NPC225279
0.8529	High Similarity	NPC300156
0.8502	High Similarity	NPC187501
0.8424	Intermediate Similarity	NPC267423
0.8424	Intermediate Similarity	NPC476044
0.8408	Intermediate Similarity	NPC243834
0.8408	Intermediate Similarity	NPC70956
0.8406	Intermediate Similarity	NPC201697
0.8308	Intermediate Similarity	NPC131017
0.8301	Intermediate Similarity	NPC470930
0.8286	Intermediate Similarity	NPC48353
0.8279	Intermediate Similarity	NPC144452
0.8265	Intermediate Similarity	NPC474688
0.8246	Intermediate Similarity	NPC39500
0.8238	Intermediate Similarity	NPC9894
0.8233	Intermediate Similarity	NPC89549
0.8174	Intermediate Similarity	NPC274640
0.8141	Intermediate Similarity	NPC160381
0.814	Intermediate Similarity	NPC298436
0.8093	Intermediate Similarity	NPC473041
0.8093	Intermediate Similarity	NPC184408
0.8084	Intermediate Similarity	NPC148183
0.8084	Intermediate Similarity	NPC152768
0.8072	Intermediate Similarity	NPC39370
0.8065	Intermediate Similarity	NPC477532
0.8063	Intermediate Similarity	NPC473186
0.8057	Intermediate Similarity	NPC209769
0.8053	Intermediate Similarity	NPC475844
0.8048	Intermediate Similarity	NPC193777
0.8028	Intermediate Similarity	NPC264176
0.8019	Intermediate Similarity	NPC269367
0.8018	Intermediate Similarity	NPC477533
0.8009	Intermediate Similarity	NPC471762
0.7963	Intermediate Similarity	NPC293151
0.7955	Intermediate Similarity	NPC21638
0.7955	Intermediate Similarity	NPC97746
0.795	Intermediate Similarity	NPC84478
0.7931	Intermediate Similarity	NPC473188
0.7928	Intermediate Similarity	NPC194740
0.791	Intermediate Similarity	NPC94943
0.7909	Intermediate Similarity	NPC51388
0.7897	Intermediate Similarity	NPC146418
0.788	Intermediate Similarity	NPC305984
0.7877	Intermediate Similarity	NPC283117
0.787	Intermediate Similarity	NPC16066
0.787	Intermediate Similarity	NPC118228
0.7861	Intermediate Similarity	NPC190007
0.7857	Intermediate Similarity	NPC474701
0.7848	Intermediate Similarity	NPC252251
0.7848	Intermediate Similarity	NPC66777
0.7847	Intermediate Similarity	NPC329747
0.7847	Intermediate Similarity	NPC11017
0.7844	Intermediate Similarity	NPC303658
0.7814	Intermediate Similarity	NPC294375
0.7811	Intermediate Similarity	NPC212535
0.7778	Intermediate Similarity	NPC477531
0.7778	Intermediate Similarity	NPC475253
0.7757	Intermediate Similarity	NPC470931
0.7748	Intermediate Similarity	NPC122436
0.7733	Intermediate Similarity	NPC209174
0.7729	Intermediate Similarity	NPC101350
0.7727	Intermediate Similarity	NPC473179
0.771	Intermediate Similarity	NPC321428
0.77	Intermediate Similarity	NPC285558
0.7699	Intermediate Similarity	NPC217176
0.7692	Intermediate Similarity	NPC323969
0.7686	Intermediate Similarity	NPC235685
0.7685	Intermediate Similarity	NPC471304
0.7682	Intermediate Similarity	NPC96321
0.7682	Intermediate Similarity	NPC475666
0.7674	Intermediate Similarity	NPC475910
0.7672	Intermediate Similarity	NPC188400
0.7653	Intermediate Similarity	NPC134848
0.7652	Intermediate Similarity	NPC131486
0.7645	Intermediate Similarity	NPC100734
0.7645	Intermediate Similarity	NPC88923
0.7645	Intermediate Similarity	NPC315634
0.7644	Intermediate Similarity	NPC478078
0.7639	Intermediate Similarity	NPC81939
0.7637	Intermediate Similarity	NPC244543
0.7632	Intermediate Similarity	NPC473105
0.7627	Intermediate Similarity	NPC133609
0.7621	Intermediate Similarity	NPC242928
0.7619	Intermediate Similarity	NPC153042
0.7595	Intermediate Similarity	NPC189079
0.7591	Intermediate Similarity	NPC170114
0.7591	Intermediate Similarity	NPC330009
0.7583	Intermediate Similarity	NPC284685
0.7583	Intermediate Similarity	NPC306376
0.7578	Intermediate Similarity	NPC60621
0.7576	Intermediate Similarity	NPC470785
0.7576	Intermediate Similarity	NPC470784
0.7566	Intermediate Similarity	NPC157931
0.7564	Intermediate Similarity	NPC78609
0.7547	Intermediate Similarity	NPC128823
0.7546	Intermediate Similarity	NPC183777
0.7545	Intermediate Similarity	NPC470549
0.7544	Intermediate Similarity	NPC260434
0.7542	Intermediate Similarity	NPC91868
0.7542	Intermediate Similarity	NPC63971
0.7534	Intermediate Similarity	NPC472099
0.7532	Intermediate Similarity	NPC184680
0.7523	Intermediate Similarity	NPC131885
0.7523	Intermediate Similarity	NPC135887
0.7523	Intermediate Similarity	NPC199277
0.7522	Intermediate Similarity	NPC470018
0.75	Intermediate Similarity	NPC472589
0.749	Intermediate Similarity	NPC472588
0.7489	Intermediate Similarity	NPC473185
0.7479	Intermediate Similarity	NPC191489
0.7476	Intermediate Similarity	NPC475190
0.7468	Intermediate Similarity	NPC168922
0.7465	Intermediate Similarity	NPC241263
0.7463	Intermediate Similarity	NPC176127
0.7455	Intermediate Similarity	NPC469439
0.7443	Intermediate Similarity	NPC470020
0.7443	Intermediate Similarity	NPC11464
0.7443	Intermediate Similarity	NPC199667
0.7442	Intermediate Similarity	NPC295898
0.744	Intermediate Similarity	NPC195788
0.744	Intermediate Similarity	NPC237901
0.7435	Intermediate Similarity	NPC132329
0.7426	Intermediate Similarity	NPC1608
0.7407	Intermediate Similarity	NPC223427
0.7406	Intermediate Similarity	NPC67401
0.7404	Intermediate Similarity	NPC166712
0.7398	Intermediate Similarity	NPC76982
0.7397	Intermediate Similarity	NPC473181
0.7395	Intermediate Similarity	NPC232727
0.7391	Intermediate Similarity	NPC260909
0.7389	Intermediate Similarity	NPC84347
0.738	Intermediate Similarity	NPC311906
0.7376	Intermediate Similarity	NPC12344
0.7376	Intermediate Similarity	NPC474409
0.7376	Intermediate Similarity	NPC473180
0.7371	Intermediate Similarity	NPC277351
0.7371	Intermediate Similarity	NPC34770
0.7364	Intermediate Similarity	NPC167860
0.7364	Intermediate Similarity	NPC123976
0.7359	Intermediate Similarity	NPC475720
0.7359	Intermediate Similarity	NPC49547
0.7359	Intermediate Similarity	NPC474192
0.7357	Intermediate Similarity	NPC205372
0.7346	Intermediate Similarity	NPC472113
0.7342	Intermediate Similarity	NPC471080
0.7342	Intermediate Similarity	NPC469592
0.7336	Intermediate Similarity	NPC74575
0.733	Intermediate Similarity	NPC220337
0.733	Intermediate Similarity	NPC474798
0.7328	Intermediate Similarity	NPC473182
0.7324	Intermediate Similarity	NPC13880
0.7322	Intermediate Similarity	NPC270515
0.7317	Intermediate Similarity	NPC72980
0.7314	Intermediate Similarity	NPC303374
0.7311	Intermediate Similarity	NPC469734
0.7311	Intermediate Similarity	NPC58209
0.7308	Intermediate Similarity	NPC473189
0.7301	Intermediate Similarity	NPC86078
0.7301	Intermediate Similarity	NPC128115
0.7297	Intermediate Similarity	NPC94157
0.7294	Intermediate Similarity	NPC301292
0.7294	Intermediate Similarity	NPC313112
0.7292	Intermediate Similarity	NPC203373
0.7292	Intermediate Similarity	NPC165964
0.7291	Intermediate Similarity	NPC471303
0.7289	Intermediate Similarity	NPC469594
0.7289	Intermediate Similarity	NPC264285
0.7286	Intermediate Similarity	NPC246700

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 NPC198503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	696
0.2-0.3	985
0.3-0.4	1422
0.4-0.5	2763
0.5-0.6	2073
0.6-0.7	748
0.7-0.8	106
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
0.8349	Intermediate Similarity	NPD5632	Approved
0.8279	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD6790	Phase 1
0.793	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD3003	Approved
0.7812	Intermediate Similarity	NPD4952	Phase 3
0.7812	Intermediate Similarity	NPD5479	Discontinued
0.7811	Intermediate Similarity	NPD5482	Discontinued
0.7773	Intermediate Similarity	NPD6242	Discontinued
0.7709	Intermediate Similarity	NPD4373	Phase 2
0.7699	Intermediate Similarity	NPD6962	Phase 2
0.7645	Intermediate Similarity	NPD7803	Approved
0.7626	Intermediate Similarity	NPD5902	Approved
0.7626	Intermediate Similarity	NPD5903	Approved
0.7593	Intermediate Similarity	NPD5658	Approved
0.7583	Intermediate Similarity	NPD7956	Approved
0.7583	Intermediate Similarity	NPD7955	Approved
0.7571	Intermediate Similarity	NPD5512	Phase 3
0.7564	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1768	Approved
0.7545	Intermediate Similarity	NPD5293	Phase 2
0.7536	Intermediate Similarity	NPD5003	Discontinued
0.7511	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD5416	Discontinued
0.7479	Intermediate Similarity	NPD7708	Approved
0.7458	Intermediate Similarity	NPD5488	Discontinued
0.7441	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD8429	Approved
0.744	Intermediate Similarity	NPD8466	Approved
0.744	Intermediate Similarity	NPD8465	Approved
0.744	Intermediate Similarity	NPD8427	Approved
0.744	Intermediate Similarity	NPD8428	Approved
0.744	Intermediate Similarity	NPD8467	Approved
0.7429	Intermediate Similarity	NPD5450	Discontinued
0.7424	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3259	Approved
0.7412	Intermediate Similarity	NPD7994	Phase 2
0.7401	Intermediate Similarity	NPD3925	Approved
0.7391	Intermediate Similarity	NPD8460	Approved
0.7391	Intermediate Similarity	NPD8459	Approved
0.7389	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD3257	Approved
0.7385	Intermediate Similarity	NPD5429	Discontinued
0.7383	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5901	Discontinued
0.7366	Intermediate Similarity	NPD6985	Discontinued
0.7366	Intermediate Similarity	NPD7395	Discontinued
0.7362	Intermediate Similarity	NPD7417	Discontinued
0.7358	Intermediate Similarity	NPD4418	Discontinued
0.7339	Intermediate Similarity	NPD8363	Approved
0.7339	Intermediate Similarity	NPD8364	Approved
0.7336	Intermediate Similarity	NPD6530	Approved
0.7336	Intermediate Similarity	NPD6531	Approved
0.7333	Intermediate Similarity	NPD7194	Discontinued
0.7333	Intermediate Similarity	NPD3258	Approved
0.7333	Intermediate Similarity	NPD2565	Phase 2
0.7333	Intermediate Similarity	NPD2564	Approved
0.7323	Intermediate Similarity	NPD8426	Approved
0.7323	Intermediate Similarity	NPD8425	Approved
0.7306	Intermediate Similarity	NPD1392	Approved
0.7297	Intermediate Similarity	NPD7069	Discontinued
0.7294	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4885	Approved
0.728	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD3945	Discontinued
0.7261	Intermediate Similarity	NPD4328	Approved
0.726	Intermediate Similarity	NPD8403	Phase 1
0.7253	Intermediate Similarity	NPD7558	Phase 2
0.7253	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2916	Discontinued
0.7192	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7853	Phase 2
0.7185	Intermediate Similarity	NPD6716	Phase 1
0.7175	Intermediate Similarity	NPD5067	Phase 2
0.7175	Intermediate Similarity	NPD5066	Phase 2
0.7162	Intermediate Similarity	NPD4506	Discontinued
0.7162	Intermediate Similarity	NPD6995	Phase 1
0.715	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3825	Phase 3
0.7137	Intermediate Similarity	NPD8358	Approved
0.7137	Intermediate Similarity	NPD4429	Discontinued
0.713	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5612	Discontinued
0.7124	Intermediate Similarity	NPD5022	Discontinued
0.7124	Intermediate Similarity	NPD4981	Phase 2
0.711	Intermediate Similarity	NPD3289	Phase 3
0.711	Intermediate Similarity	NPD3290	Approved
0.7104	Intermediate Similarity	NPD6245	Phase 2
0.7103	Intermediate Similarity	NPD5937	Approved
0.7098	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6220	Phase 3
0.7094	Intermediate Similarity	NPD1867	Approved
0.7093	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6550	Discontinued
0.7078	Intermediate Similarity	NPD3986	Discontinued
0.7072	Intermediate Similarity	NPD7453	Approved
0.7072	Intermediate Similarity	NPD7222	Phase 2
0.7072	Intermediate Similarity	NPD7452	Approved
0.707	Intermediate Similarity	NPD1038	Approved
0.7069	Intermediate Similarity	NPD7426	Phase 1
0.7067	Intermediate Similarity	NPD5866	Approved
0.7061	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5913	Phase 3
0.7048	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8102	Discontinued
0.7037	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4501	Approved
0.7032	Intermediate Similarity	NPD4500	Approved
0.7031	Intermediate Similarity	NPD6974	Phase 3
0.7031	Intermediate Similarity	NPD6770	Approved
0.7027	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1505	Phase 2
0.7019	Intermediate Similarity	NPD8489	Phase 1
0.7014	Intermediate Similarity	NPD6176	Phase 1
0.7014	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5513	Phase 2
0.7009	Intermediate Similarity	NPD5559	Phase 2
0.7004	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5930	Phase 3
0.6987	Remote Similarity	NPD1926	Approved
0.6986	Remote Similarity	NPD3920	Phase 2
0.6982	Remote Similarity	NPD3947	Discontinued
0.6976	Remote Similarity	NPD8091	Phase 3
0.6972	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4558	Phase 2
0.6964	Remote Similarity	NPD2509	Approved
0.6964	Remote Similarity	NPD2510	Approved
0.6959	Remote Similarity	NPD6590	Discontinued
0.6958	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7688	Phase 1
0.6946	Remote Similarity	NPD5805	Approved
0.6943	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5164	Discontinued
0.6937	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2920	Discontinued
0.6926	Remote Similarity	NPD7180	Phase 3
0.6923	Remote Similarity	NPD5532	Phase 2
0.692	Remote Similarity	NPD6228	Discontinued
0.6909	Remote Similarity	NPD2778	Approved
0.6907	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3006	Discontinued
0.6895	Remote Similarity	NPD6988	Phase 1
0.689	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4356	Discontinued
0.6881	Remote Similarity	NPD6251	Discontinued
0.6878	Remote Similarity	NPD4601	Approved
0.6878	Remote Similarity	NPD4600	Approved
0.6875	Remote Similarity	NPD7689	Approved
0.6875	Remote Similarity	NPD6150	Discontinued
0.6869	Remote Similarity	NPD5256	Discontinued
0.6864	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD2951	Discontinued
0.6855	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4499	Approved
0.6851	Remote Similarity	NPD3263	Phase 3
0.6847	Remote Similarity	NPD4511	Phase 1
0.6842	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4203	Approved
0.684	Remote Similarity	NPD6745	Discontinued
0.684	Remote Similarity	NPD4204	Approved
0.6838	Remote Similarity	NPD7548	Discontinued
0.6837	Remote Similarity	NPD4948	Discontinued
0.6835	Remote Similarity	NPD802	Phase 2
0.6835	Remote Similarity	NPD4539	Phase 1
0.6835	Remote Similarity	NPD5924	Discontinued
0.6831	Remote Similarity	NPD6473	Phase 1
0.683	Remote Similarity	NPD3397	Phase 2
0.6828	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3393	Approved
0.6826	Remote Similarity	NPD3389	Approved
0.6826	Remote Similarity	NPD3394	Approved
0.6822	Remote Similarity	NPD4889	Approved
0.682	Remote Similarity	NPD6494	Phase 2
0.6818	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7626	Approved
0.6816	Remote Similarity	NPD2779	Approved
0.6816	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7627	Approved
0.6814	Remote Similarity	NPD6376	Discontinued
0.6814	Remote Similarity	NPD7467	Discontinued
0.6812	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3402	Phase 1
0.6805	Remote Similarity	NPD4368	Phase 2
0.6797	Remote Similarity	NPD6719	Approved
0.6795	Remote Similarity	NPD8311	Discontinued
0.6794	Remote Similarity	NPD2248	Approved
0.6794	Remote Similarity	NPD2246	Approved
0.6793	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6963	Approved
0.6792	Remote Similarity	NPD6964	Approved
0.6787	Remote Similarity	NPD8463	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data