NPASS Compound

Structure

NPC473180 OpenBabel07101718292D 32 37 0 0 0 0 0 0 0 0999 V2000 -0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2701 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6989 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6934 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5768 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2921 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.0181 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 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8799 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8744 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -0.8090 0.0000 N 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 -5.4041 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 18 2 0 0 0 0 9 19 2 0 0 0 0 10 23 2 0 0 0 0 11 24 2 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 25 2 0 0 0 0 16 20 1 0 0 0 0 18 21 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 28 2 0 0 0 0 21 27 2 0 0 0 0 22 26 2 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 31 1 0 0 0 0 26 29 1 0 0 0 0 27 28 1 0 0 0 0 27 30 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	449.442
LogP:	6.643
LogD:	4.753
LogS:	-6.875
# Rotatable Bonds:	4
TPSA:	50.04
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	2.562
Fsp3:	0.143
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:	-5.74
MDCK Permeability:	1.3281121027830523e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.34
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.581
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	98.20751190185547%
Volume Distribution (VD):	0.959
Pgp-substrate:	1.2124276161193848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.904
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.889
CYP2C19-substrate:	0.197
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.797
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.722
CYP3A4-substrate:	0.9

ADMET: Excretion

Clearance (CL):	4.981
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.883
Rat Oral Acute Toxicity:	0.482
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.544
Carcinogencity:	0.88
Eye Corrosion:	0.003
Eye Irritation:	0.58
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC473180

Natural Product ID:	NPC473180
*Common Name:**	1-Methoxy-2-[(1-Methoxy-9H-Carbazol-3-Yl)Methyl]-3-Methyl-9H-Carbazole
IUPAC Name:	1-methoxy-2-[(1-methoxy-9H-carbazol-3-yl)methyl]-3-methyl-9H-carbazole
Synonyms:
Standard InCHIKey:	RZLICGQJNCVOPS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H24N2O2/c1-16-12-21-18-8-4-7-11-24(18)30-27(21)28(32-3)20(16)13-17-14-22-19-9-5-6-10-23(19)29-26(22)25(15-17)31-2/h4-12,14-15,29-30H,13H2,1-3H3
SMILES:	CC1=CC2=C(C(=C1CC3=CC4=C(C(=C3)OC)NC5=CC=CC=C54)OC)NC6=CC=CC=C62
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633076
PubChem CID:	60155041
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
NPO33199	murraya tetramera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26327273]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11400.0	nM	PMID[483226]

☑ 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 NPC473180 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	758
0.1-0.2	4276
0.2-0.3	13170
0.3-0.4	8363
0.4-0.5	11547
0.5-0.6	2966
0.6-0.7	1291
0.7-0.8	273
0.8-0.85	39
0.85-0.9	9
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC199667
0.9632	High Similarity	NPC473181
0.9184	High Similarity	NPC94157
0.91	High Similarity	NPC473179
0.8942	High Similarity	NPC473182
0.8927	High Similarity	NPC202503
0.8883	High Similarity	NPC242928
0.8867	High Similarity	NPC132642
0.8792	High Similarity	NPC473185
0.8667	High Similarity	NPC475253
0.8571	High Similarity	NPC128823
0.8564	High Similarity	NPC474798
0.8465	Intermediate Similarity	NPC473183
0.8458	Intermediate Similarity	NPC473184
0.8451	Intermediate Similarity	NPC473186
0.845	Intermediate Similarity	NPC470930
0.8413	Intermediate Similarity	NPC86078
0.8396	Intermediate Similarity	NPC252251
0.8382	Intermediate Similarity	NPC208284
0.8372	Intermediate Similarity	NPC39370
0.8325	Intermediate Similarity	NPC225279
0.8318	Intermediate Similarity	NPC477531
0.8284	Intermediate Similarity	NPC201697
0.8276	Intermediate Similarity	NPC193777
0.8271	Intermediate Similarity	NPC209174
0.8246	Intermediate Similarity	NPC144452
0.8223	Intermediate Similarity	NPC475190
0.8216	Intermediate Similarity	NPC227908
0.8209	Intermediate Similarity	NPC267423
0.8182	Intermediate Similarity	NPC131017
0.815	Intermediate Similarity	NPC72211
0.8144	Intermediate Similarity	NPC473189
0.8128	Intermediate Similarity	NPC162484
0.8116	Intermediate Similarity	NPC187501
0.8113	Intermediate Similarity	NPC477532
0.8107	Intermediate Similarity	NPC209769
0.81	Intermediate Similarity	NPC243834
0.81	Intermediate Similarity	NPC70956
0.8077	Intermediate Similarity	NPC48353
0.8066	Intermediate Similarity	NPC477533
0.8065	Intermediate Similarity	NPC474688
0.8056	Intermediate Similarity	NPC274640
0.805	Intermediate Similarity	NPC70259
0.8039	Intermediate Similarity	NPC475774
0.8038	Intermediate Similarity	NPC39500
0.802	Intermediate Similarity	NPC128751
0.802	Intermediate Similarity	NPC246700
0.8	Intermediate Similarity	NPC43787
0.8	Intermediate Similarity	NPC205934
0.798	Intermediate Similarity	NPC469497
0.798	Intermediate Similarity	NPC106833
0.7952	Intermediate Similarity	NPC478074
0.7951	Intermediate Similarity	NPC476138
0.7951	Intermediate Similarity	NPC245816
0.7945	Intermediate Similarity	NPC101543
0.7945	Intermediate Similarity	NPC469554
0.7902	Intermediate Similarity	NPC475085
0.7902	Intermediate Similarity	NPC475112
0.7902	Intermediate Similarity	NPC291535
0.7887	Intermediate Similarity	NPC184408
0.7864	Intermediate Similarity	NPC223427
0.786	Intermediate Similarity	NPC280799
0.7857	Intermediate Similarity	NPC176127
0.7854	Intermediate Similarity	NPC476044
0.785	Intermediate Similarity	NPC208084
0.784	Intermediate Similarity	NPC314552
0.7833	Intermediate Similarity	NPC153042
0.7793	Intermediate Similarity	NPC170114
0.7788	Intermediate Similarity	NPC476106
0.7788	Intermediate Similarity	NPC51388
0.7784	Intermediate Similarity	NPC56618
0.7778	Intermediate Similarity	NPC475844
0.7778	Intermediate Similarity	NPC477066
0.7746	Intermediate Similarity	NPC470549
0.7743	Intermediate Similarity	NPC478081
0.7739	Intermediate Similarity	NPC473188
0.7737	Intermediate Similarity	NPC118511
0.7736	Intermediate Similarity	NPC26679
0.7718	Intermediate Similarity	NPC329793
0.7703	Intermediate Similarity	NPC304183
0.7689	Intermediate Similarity	NPC11408
0.7679	Intermediate Similarity	NPC473187
0.7678	Intermediate Similarity	NPC185782
0.7674	Intermediate Similarity	NPC293151
0.767	Intermediate Similarity	NPC18487
0.7668	Intermediate Similarity	NPC180504
0.7665	Intermediate Similarity	NPC477067
0.7665	Intermediate Similarity	NPC478082
0.7656	Intermediate Similarity	NPC285558
0.7653	Intermediate Similarity	NPC294620
0.7647	Intermediate Similarity	NPC314954
0.7638	Intermediate Similarity	NPC84478
0.7636	Intermediate Similarity	NPC200888
0.7635	Intermediate Similarity	NPC114335
0.7635	Intermediate Similarity	NPC280964
0.7635	Intermediate Similarity	NPC141915
0.7633	Intermediate Similarity	NPC11017
0.7633	Intermediate Similarity	NPC329747
0.7623	Intermediate Similarity	NPC49547
0.7621	Intermediate Similarity	NPC217554
0.7619	Intermediate Similarity	NPC300156
0.7619	Intermediate Similarity	NPC45190
0.7617	Intermediate Similarity	NPC476287
0.7614	Intermediate Similarity	NPC88363
0.76	Intermediate Similarity	NPC94943
0.7591	Intermediate Similarity	NPC179287
0.7588	Intermediate Similarity	NPC473540
0.7581	Intermediate Similarity	NPC118228
0.7578	Intermediate Similarity	NPC474701
0.7559	Intermediate Similarity	NPC471304
0.7557	Intermediate Similarity	NPC470018
0.7556	Intermediate Similarity	NPC277351
0.755	Intermediate Similarity	NPC190007
0.7548	Intermediate Similarity	NPC19872
0.7547	Intermediate Similarity	NPC470931
0.7537	Intermediate Similarity	NPC76748
0.7532	Intermediate Similarity	NPC17437
0.7523	Intermediate Similarity	NPC74575
0.7522	Intermediate Similarity	NPC208522
0.7522	Intermediate Similarity	NPC284141
0.7512	Intermediate Similarity	NPC307963
0.7511	Intermediate Similarity	NPC89549
0.75	Intermediate Similarity	NPC212535
0.75	Intermediate Similarity	NPC92111
0.7488	Intermediate Similarity	NPC137929
0.7488	Intermediate Similarity	NPC164374
0.7488	Intermediate Similarity	NPC296527
0.7476	Intermediate Similarity	NPC195314
0.7465	Intermediate Similarity	NPC8022
0.7465	Intermediate Similarity	NPC470799
0.7464	Intermediate Similarity	NPC176538
0.7454	Intermediate Similarity	NPC469592
0.7454	Intermediate Similarity	NPC471080
0.7442	Intermediate Similarity	NPC9894
0.7438	Intermediate Similarity	NPC473177
0.7426	Intermediate Similarity	NPC42591
0.7418	Intermediate Similarity	NPC4687
0.7418	Intermediate Similarity	NPC249583
0.7418	Intermediate Similarity	NPC283117
0.7415	Intermediate Similarity	NPC478080
0.7407	Intermediate Similarity	NPC308137
0.7407	Intermediate Similarity	NPC310211
0.74	Intermediate Similarity	NPC478032
0.7397	Intermediate Similarity	NPC46561
0.7395	Intermediate Similarity	NPC167860
0.7395	Intermediate Similarity	NPC123976
0.7393	Intermediate Similarity	NPC199277
0.7393	Intermediate Similarity	NPC135887
0.7393	Intermediate Similarity	NPC26543
0.7383	Intermediate Similarity	NPC475910
0.7376	Intermediate Similarity	NPC198503
0.7374	Intermediate Similarity	NPC312872
0.7364	Intermediate Similarity	NPC46451
0.7364	Intermediate Similarity	NPC292958
0.7356	Intermediate Similarity	NPC251090
0.7352	Intermediate Similarity	NPC169402
0.7344	Intermediate Similarity	NPC26850
0.7342	Intermediate Similarity	NPC280272
0.734	Intermediate Similarity	NPC476319
0.7339	Intermediate Similarity	NPC116238
0.7339	Intermediate Similarity	NPC235076
0.7336	Intermediate Similarity	NPC6786
0.7333	Intermediate Similarity	NPC32200
0.733	Intermediate Similarity	NPC150239
0.7327	Intermediate Similarity	NPC474428
0.7327	Intermediate Similarity	NPC251160
0.7327	Intermediate Similarity	NPC38237
0.7318	Intermediate Similarity	NPC469594
0.7318	Intermediate Similarity	NPC96321
0.7318	Intermediate Similarity	NPC23614
0.7318	Intermediate Similarity	NPC100079
0.7315	Intermediate Similarity	NPC188420
0.7311	Intermediate Similarity	NPC53534
0.7294	Intermediate Similarity	NPC149471
0.7294	Intermediate Similarity	NPC271215
0.7289	Intermediate Similarity	NPC470126
0.7281	Intermediate Similarity	NPC294375
0.7281	Intermediate Similarity	NPC329631
0.7281	Intermediate Similarity	NPC87413
0.7273	Intermediate Similarity	NPC13880
0.7265	Intermediate Similarity	NPC475666
0.7264	Intermediate Similarity	NPC232727
0.726	Intermediate Similarity	NPC473178
0.7257	Intermediate Similarity	NPC253580
0.7251	Intermediate Similarity	NPC476167
0.724	Intermediate Similarity	NPC247803
0.724	Intermediate Similarity	NPC303658
0.7238	Intermediate Similarity	NPC478083
0.7236	Intermediate Similarity	NPC474409
0.7235	Intermediate Similarity	NPC11464
0.7222	Intermediate Similarity	NPC477111
0.7222	Intermediate Similarity	NPC81939
0.722	Intermediate Similarity	NPC204385
0.7215	Intermediate Similarity	NPC266931
0.7215	Intermediate Similarity	NPC324361
0.7207	Intermediate Similarity	NPC213530
0.7207	Intermediate Similarity	NPC193267
0.7204	Intermediate Similarity	NPC192315
0.7203	Intermediate Similarity	NPC270515
0.7202	Intermediate Similarity	NPC132385

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 NPC473180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	433
0.1-0.2	717
0.2-0.3	882
0.3-0.4	1635
0.4-0.5	2892
0.5-0.6	1955
0.6-0.7	558
0.7-0.8	77
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8075	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5164	Discontinued
0.7814	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7773	Intermediate Similarity	NPD4502	Phase 2
0.7664	Intermediate Similarity	NPD5902	Approved
0.7664	Intermediate Similarity	NPD5903	Approved
0.7662	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3003	Approved
0.7619	Intermediate Similarity	NPD5530	Phase 1
0.7606	Intermediate Similarity	NPD5939	Approved
0.7606	Intermediate Similarity	NPD5936	Approved
0.7586	Intermediate Similarity	NPD5913	Phase 3
0.7586	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD5429	Discontinued
0.7561	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5658	Approved
0.7532	Intermediate Similarity	NPD8358	Approved
0.7512	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD1038	Approved
0.75	Intermediate Similarity	NPD8395	Approved
0.75	Intermediate Similarity	NPD7222	Phase 2
0.75	Intermediate Similarity	NPD8396	Approved
0.7476	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3746	Discontinued
0.7463	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD8403	Phase 1
0.7429	Intermediate Similarity	NPD4511	Phase 1
0.7418	Intermediate Similarity	NPD7452	Approved
0.7418	Intermediate Similarity	NPD7453	Approved
0.7397	Intermediate Similarity	NPD6985	Discontinued
0.7378	Intermediate Similarity	NPD5479	Discontinued
0.7371	Intermediate Similarity	NPD6150	Discontinued
0.7364	Intermediate Similarity	NPD7194	Discontinued
0.7364	Intermediate Similarity	NPD3763	Approved
0.7364	Intermediate Similarity	NPD3875	Discontinued
0.7355	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD3920	Phase 2
0.7333	Intermediate Similarity	NPD2175	Phase 3
0.7333	Intermediate Similarity	NPD2176	Approved
0.7333	Intermediate Similarity	NPD1768	Approved
0.7333	Intermediate Similarity	NPD2177	Approved
0.7333	Intermediate Similarity	NPD3825	Phase 3
0.7318	Intermediate Similarity	NPD7395	Discontinued
0.7281	Intermediate Similarity	NPD5066	Phase 2
0.7281	Intermediate Similarity	NPD5067	Phase 2
0.7281	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6290	Phase 2
0.7248	Intermediate Similarity	NPD4927	Discontinued
0.724	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8244	Phase 2
0.723	Intermediate Similarity	NPD6208	Discontinued
0.7227	Intermediate Similarity	NPD5612	Discontinued
0.722	Intermediate Similarity	NPD5256	Discontinued
0.7214	Intermediate Similarity	NPD5810	Discontinued
0.7207	Intermediate Similarity	NPD3402	Phase 1
0.7205	Intermediate Similarity	NPD7558	Phase 2
0.7202	Intermediate Similarity	NPD6220	Phase 3
0.719	Intermediate Similarity	NPD6550	Discontinued
0.7189	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7219	Approved
0.7188	Intermediate Similarity	NPD7221	Approved
0.7181	Intermediate Similarity	NPD7555	Discontinued
0.7181	Intermediate Similarity	NPD5559	Phase 2
0.7181	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7592	Phase 2
0.7173	Intermediate Similarity	NPD3835	Phase 3
0.7173	Intermediate Similarity	NPD3833	Phase 3
0.7162	Intermediate Similarity	NPD5632	Approved
0.715	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6590	Discontinued
0.7143	Intermediate Similarity	NPD4418	Discontinued
0.7143	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3945	Discontinued
0.7136	Intermediate Similarity	NPD1325	Approved
0.7136	Intermediate Similarity	NPD1326	Approved
0.7129	Intermediate Similarity	NPD6159	Phase 2
0.7124	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD2951	Discontinued
0.7098	Intermediate Similarity	NPD6242	Discontinued
0.7097	Intermediate Similarity	NPD1392	Approved
0.7089	Intermediate Similarity	NPD4548	Discontinued
0.7087	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4885	Approved
0.7085	Intermediate Similarity	NPD4429	Discontinued
0.7075	Intermediate Similarity	NPD6988	Phase 1
0.7075	Intermediate Similarity	NPD5003	Discontinued
0.7075	Intermediate Similarity	NPD7948	Phase 1
0.7073	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD2187	Approved
0.7064	Intermediate Similarity	NPD7672	Approved
0.7064	Intermediate Similarity	NPD7671	Approved
0.7064	Intermediate Similarity	NPD2189	Approved
0.7062	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6251	Discontinued
0.7061	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD6978	Phase 2
0.7051	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2920	Discontinued
0.7028	Intermediate Similarity	NPD5512	Phase 3
0.7028	Intermediate Similarity	NPD3477	Phase 2
0.7028	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5930	Phase 3
0.7016	Intermediate Similarity	NPD8364	Approved
0.7016	Intermediate Similarity	NPD8363	Approved
0.7014	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6750	Phase 2
0.7005	Intermediate Similarity	NPD4795	Phase 2
0.7004	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD4442	Phase 2
0.7	Intermediate Similarity	NPD6968	Phase 2
0.7	Intermediate Similarity	NPD6969	Phase 2
0.7	Intermediate Similarity	NPD7567	Approved
0.6996	Remote Similarity	NPD3006	Discontinued
0.6996	Remote Similarity	NPD4454	Phase 2
0.6995	Remote Similarity	NPD4354	Approved
0.6992	Remote Similarity	NPD6456	Discontinued
0.6991	Remote Similarity	NPD6975	Discontinued
0.6983	Remote Similarity	NPD6494	Phase 2
0.6981	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD8016	Phase 3
0.697	Remote Similarity	NPD7688	Phase 1
0.6968	Remote Similarity	NPD5416	Discontinued
0.6967	Remote Similarity	NPD3924	Approved
0.6967	Remote Similarity	NPD3923	Approved
0.6967	Remote Similarity	NPD3921	Approved
0.6967	Remote Similarity	NPD3922	Approved
0.6963	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1856	Discontinued
0.696	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6995	Phase 1
0.6948	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD8431	Approved
0.6937	Remote Similarity	NPD6202	Discontinued
0.6937	Remote Similarity	NPD3816	Phase 1
0.6937	Remote Similarity	NPD3815	Phase 1
0.693	Remote Similarity	NPD5999	Phase 2
0.692	Remote Similarity	NPD6473	Phase 1
0.692	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7392	Phase 2
0.6916	Remote Similarity	NPD7726	Phase 1
0.6916	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5488	Discontinued
0.6903	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7659	Discontinued
0.6898	Remote Similarity	NPD1740	Approved
0.6898	Remote Similarity	NPD1739	Approved
0.6893	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD5482	Discontinued
0.6886	Remote Similarity	NPD6736	Discontinued
0.6886	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2564	Approved
0.6872	Remote Similarity	NPD2565	Phase 2
0.6872	Remote Similarity	NPD6281	Approved
0.6872	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7603	Discontinued
0.687	Remote Similarity	NPD7051	Phase 3
0.687	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5044	Phase 2
0.686	Remote Similarity	NPD4203	Approved
0.686	Remote Similarity	NPD4204	Approved
0.6857	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7994	Phase 2
0.6838	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2916	Discontinued
0.6832	Remote Similarity	NPD5021	Discontinued
0.683	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6455	Phase 3
0.6823	Remote Similarity	NPD5254	Discontinued
0.6818	Remote Similarity	NPD6245	Phase 2
0.6816	Remote Similarity	NPD6961	Discontinued
0.6814	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6760	Discontinued
0.6808	Remote Similarity	NPD6569	Phase 2
0.6807	Remote Similarity	NPD7417	Discontinued
0.6804	Remote Similarity	NPD6991	Approved
0.6802	Remote Similarity	NPD6530	Approved
0.6802	Remote Similarity	NPD6531	Approved
0.68	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3330	Phase 1
0.6784	Remote Similarity	NPD8466	Approved
0.6784	Remote Similarity	NPD8465	Approved
0.6784	Remote Similarity	NPD8428	Approved
0.6784	Remote Similarity	NPD8429	Approved
0.6784	Remote Similarity	NPD8427	Approved
0.6784	Remote Similarity	NPD8467	Approved
0.6781	Remote Similarity	NPD5022	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