NPASS Compound

Structure

CID205934 OpenBabel06191715592D 25 28 0 0 1 0 0 0 0 0999 V2000 -0.5044 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0173 0.7862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0329 1.9428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0090 -0.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8304 1.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8302 0.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5136 -1.8347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0178 -0.9610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9978 1.9226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9974 -0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6651 -0.9619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5049 -1.8350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8323 -1.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6657 1.9233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5132 -0.0875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8330 1.4426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1646 1.4420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6654 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4988 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1644 0.4799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4986 0.4802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8328 0.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9615 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3317 -0.0008 0.0000 N 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 23 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 8 1 0 0 0 0 7 12 1 0 0 0 0 8 15 2 0 0 0 0 9 17 2 0 0 0 0 10 20 2 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 20 24 1 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 23 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	331.19
Volume:	370.834
LogP:	6.923
LogD:	5.258
LogS:	-6.743
# Rotatable Bonds:	3
TPSA:	25.02
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	3.359
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.008
MDCK Permeability:	1.3953414963907562e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.043
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.325

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	95.56425476074219%
Volume Distribution (VD):	4.365
Pgp-substrate:	3.358393907546997%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.334
CYP2C19-inhibitor:	0.938
CYP2C19-substrate:	0.556
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.965
CYP2D6-substrate:	0.588
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.322

ADMET: Excretion

Clearance (CL):	7.828
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.675
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.409
AMES Toxicity:	0.436
Rat Oral Acute Toxicity:	0.444
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.927
Carcinogencity:	0.736
Eye Corrosion:	0.003
Eye Irritation:	0.173
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC205934

Natural Product ID:	NPC205934
*Common Name:**	Mahanimbine
IUPAC Name:	3,5-dimethyl-3-(4-methylpent-3-enyl)-11H-pyrano[3,2-a]carbazole
Synonyms:	Mahanimbine; Rel-(+)-Mahanimbine
Standard InCHIKey:	HTNVFUBCWIYPJN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H25NO/c1-15(2)8-7-12-23(4)13-11-18-21-19(14-16(3)22(18)25-23)17-9-5-6-10-20(17)24-21/h5-6,8-11,13-14,24H,7,12H2,1-4H3
SMILES:	CC(=CCCC1(C)C=Cc2c3c(cc(C)c2O1)c1ccccc1[nH]3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495873
PubChem CID:	167963
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
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10757740]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	flower	n.a.	PMID[10757740]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757740]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[10757740]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	stem bark;fruit	n.a.	n.a.	PMID[10924160]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	root bark	Kuantaochi, Nantou Hsien, Taiwan	n.a.	PMID[10924160]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662104]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[23376010]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	fruits	Coimbatore, India	2010-JUN	PMID[23691929]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27136692]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29303577]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2715.1	Murraya paniculata var. exotica	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715.1	Murraya paniculata var. exotica	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3364	Murraya koenigii	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	2
Others	11
Potency	6

Activity Type	# Activity
Individual Protein	10
Others	8
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	8912.5	nM	PMID[553140]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[553140]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	6.2	%	PMID[553141]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	2.7	%	PMID[553141]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	-0.4	%	PMID[553141]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	-3.2	%	PMID[553141]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	-1.3	%	PMID[553141]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[553140]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	3662.6	nM	PMID[553140]
NPT2797	Individual Protein	Pancreatic lipase	Homo sapiens	IC50	=	17900.0	nM	PMID[553142]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	3162.3	nM	PMID[553140]
NPT27	Others	Unspecified		Activity	=	35.1	%	PMID[553141]
NPT27	Others	Unspecified		Activity	=	34.4	%	PMID[553141]
NPT27	Others	Unspecified		Activity	=	68.7	%	PMID[553141]
NPT27	Others	Unspecified		Activity	=	94.3	%	PMID[553141]
NPT2	Others	Unspecified		IC50	=	1400.0	nM	PMID[553141]
NPT2	Others	Unspecified		Inhibition	=	63.9	%	PMID[553141]
NPT2	Others	Unspecified		Inhibition	=	43.3	%	PMID[553141]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[553140]

☑ 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 NPC205934 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	700
0.1-0.2	4021
0.2-0.3	13343
0.3-0.4	5993
0.4-0.5	13500
0.5-0.6	3159
0.6-0.7	1597
0.7-0.8	286
0.8-0.85	54
0.85-0.9	18
0.9-0.95	13
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43787
0.9942	High Similarity	NPC70259
0.9829	High Similarity	NPC72211
0.9609	High Similarity	NPC291535
0.9609	High Similarity	NPC475085
0.9609	High Similarity	NPC475112
0.9556	High Similarity	NPC162484
0.9553	High Similarity	NPC267423
0.9553	High Similarity	NPC476044
0.9451	High Similarity	NPC476106
0.9297	High Similarity	NPC201697
0.9222	High Similarity	NPC70956
0.9222	High Similarity	NPC243834
0.9149	High Similarity	NPC48353
0.9111	High Similarity	NPC131017
0.9081	High Similarity	NPC470930
0.8927	High Similarity	NPC190007
0.8889	High Similarity	NPC209769
0.8876	High Similarity	NPC94943
0.8865	High Similarity	NPC11017
0.882	High Similarity	NPC84478
0.8783	High Similarity	NPC193777
0.8776	High Similarity	NPC198503
0.8776	High Similarity	NPC477532
0.8764	High Similarity	NPC212535
0.8724	High Similarity	NPC477533
0.8663	High Similarity	NPC329747
0.8542	High Similarity	NPC470931
0.8515	High Similarity	NPC252251
0.8482	Intermediate Similarity	NPC285558
0.8473	Intermediate Similarity	NPC209174
0.8431	Intermediate Similarity	NPC475253
0.8431	Intermediate Similarity	NPC477531
0.8424	Intermediate Similarity	NPC242928
0.8404	Intermediate Similarity	NPC153042
0.8394	Intermediate Similarity	NPC4687
0.8394	Intermediate Similarity	NPC249583
0.8392	Intermediate Similarity	NPC473179
0.8367	Intermediate Similarity	NPC310211
0.8367	Intermediate Similarity	NPC308137
0.8291	Intermediate Similarity	NPC169402
0.8283	Intermediate Similarity	NPC470549
0.8283	Intermediate Similarity	NPC116238
0.8268	Intermediate Similarity	NPC474409
0.8259	Intermediate Similarity	NPC150239
0.8256	Intermediate Similarity	NPC475910
0.8251	Intermediate Similarity	NPC176127
0.8241	Intermediate Similarity	NPC170114
0.8223	Intermediate Similarity	NPC87413
0.8218	Intermediate Similarity	NPC280799
0.8187	Intermediate Similarity	NPC72980
0.8187	Intermediate Similarity	NPC135887
0.8187	Intermediate Similarity	NPC199277
0.8159	Intermediate Similarity	NPC247803
0.8159	Intermediate Similarity	NPC46561
0.8143	Intermediate Similarity	NPC6786
0.8135	Intermediate Similarity	NPC232727
0.8128	Intermediate Similarity	NPC246700
0.8125	Intermediate Similarity	NPC128823
0.8122	Intermediate Similarity	NPC473181
0.8107	Intermediate Similarity	NPC473185
0.8098	Intermediate Similarity	NPC474798
0.8087	Intermediate Similarity	NPC88363
0.8081	Intermediate Similarity	NPC199667
0.8081	Intermediate Similarity	NPC123976
0.8081	Intermediate Similarity	NPC11464
0.8081	Intermediate Similarity	NPC167860
0.8079	Intermediate Similarity	NPC174760
0.8079	Intermediate Similarity	NPC86078
0.8063	Intermediate Similarity	NPC13880
0.8053	Intermediate Similarity	NPC475190
0.8051	Intermediate Similarity	NPC223427
0.8011	Intermediate Similarity	NPC26850
0.8	Intermediate Similarity	NPC473180
0.799	Intermediate Similarity	NPC329793
0.798	Intermediate Similarity	NPC39679
0.798	Intermediate Similarity	NPC473041
0.7968	Intermediate Similarity	NPC473189
0.7962	Intermediate Similarity	NPC277351
0.795	Intermediate Similarity	NPC208284
0.7941	Intermediate Similarity	NPC208084
0.7937	Intermediate Similarity	NPC128751
0.7915	Intermediate Similarity	NPC473182
0.791	Intermediate Similarity	NPC94157
0.79	Intermediate Similarity	NPC303951
0.7895	Intermediate Similarity	NPC469497
0.7895	Intermediate Similarity	NPC106833
0.7885	Intermediate Similarity	NPC227908
0.7882	Intermediate Similarity	NPC3207
0.788	Intermediate Similarity	NPC288943
0.7879	Intermediate Similarity	NPC300156
0.7879	Intermediate Similarity	NPC45190
0.7877	Intermediate Similarity	NPC473184
0.7871	Intermediate Similarity	NPC471080
0.7871	Intermediate Similarity	NPC469592
0.7861	Intermediate Similarity	NPC23294
0.7841	Intermediate Similarity	NPC26872
0.784	Intermediate Similarity	NPC473187
0.7805	Intermediate Similarity	NPC469594
0.7804	Intermediate Similarity	NPC473183
0.7801	Intermediate Similarity	NPC76748
0.7799	Intermediate Similarity	NPC202503
0.7783	Intermediate Similarity	NPC478074
0.7767	Intermediate Similarity	NPC213530
0.7767	Intermediate Similarity	NPC193267
0.776	Intermediate Similarity	NPC92111
0.7756	Intermediate Similarity	NPC305984
0.7751	Intermediate Similarity	NPC179287
0.7749	Intermediate Similarity	NPC296527
0.7742	Intermediate Similarity	NPC283152
0.7737	Intermediate Similarity	NPC204385
0.773	Intermediate Similarity	NPC312872
0.7723	Intermediate Similarity	NPC471304
0.7718	Intermediate Similarity	NPC303658
0.7716	Intermediate Similarity	NPC121772
0.7711	Intermediate Similarity	NPC86834
0.7711	Intermediate Similarity	NPC210828
0.7707	Intermediate Similarity	NPC152768
0.7707	Intermediate Similarity	NPC148183
0.7692	Intermediate Similarity	NPC310118
0.768	Intermediate Similarity	NPC307963
0.7656	Intermediate Similarity	NPC144452
0.7644	Intermediate Similarity	NPC225279
0.7644	Intermediate Similarity	NPC132642
0.7638	Intermediate Similarity	NPC295898
0.7629	Intermediate Similarity	NPC280964
0.7629	Intermediate Similarity	NPC141915
0.7629	Intermediate Similarity	NPC114335
0.7626	Intermediate Similarity	NPC176538
0.7621	Intermediate Similarity	NPC183407
0.761	Intermediate Similarity	NPC39500
0.7604	Intermediate Similarity	NPC46580
0.7604	Intermediate Similarity	NPC131486
0.7604	Intermediate Similarity	NPC66083
0.7602	Intermediate Similarity	NPC251090
0.7598	Intermediate Similarity	NPC187501
0.7594	Intermediate Similarity	NPC56618
0.759	Intermediate Similarity	NPC279401
0.759	Intermediate Similarity	NPC79293
0.7583	Intermediate Similarity	NPC21638
0.757	Intermediate Similarity	NPC474688
0.7561	Intermediate Similarity	NPC294620
0.7561	Intermediate Similarity	NPC316981
0.7559	Intermediate Similarity	NPC274640
0.7559	Intermediate Similarity	NPC471762
0.7557	Intermediate Similarity	NPC475666
0.7552	Intermediate Similarity	NPC160381
0.7548	Intermediate Similarity	NPC96321
0.7539	Intermediate Similarity	NPC62069
0.7526	Intermediate Similarity	NPC206201
0.7525	Intermediate Similarity	NPC306376
0.7524	Intermediate Similarity	NPC266931
0.7512	Intermediate Similarity	NPC110151
0.7511	Intermediate Similarity	NPC81939
0.75	Intermediate Similarity	NPC106937
0.7476	Intermediate Similarity	NPC264176
0.7464	Intermediate Similarity	NPC184408
0.7461	Intermediate Similarity	NPC61350
0.746	Intermediate Similarity	NPC96890
0.7452	Intermediate Similarity	NPC330009
0.745	Intermediate Similarity	NPC19872
0.7449	Intermediate Similarity	NPC99666
0.7441	Intermediate Similarity	NPC60621
0.743	Intermediate Similarity	NPC187145
0.7426	Intermediate Similarity	NPC469440
0.7424	Intermediate Similarity	NPC242209
0.7419	Intermediate Similarity	NPC180504
0.7419	Intermediate Similarity	NPC473105
0.7416	Intermediate Similarity	NPC314552
0.7415	Intermediate Similarity	NPC174758
0.7415	Intermediate Similarity	NPC469589
0.7413	Intermediate Similarity	NPC470586
0.7406	Intermediate Similarity	NPC280272
0.74	Intermediate Similarity	NPC18487
0.7395	Intermediate Similarity	NPC194740
0.7395	Intermediate Similarity	NPC66777
0.7391	Intermediate Similarity	NPC16667
0.7376	Intermediate Similarity	NPC475844
0.7371	Intermediate Similarity	NPC122436
0.7343	Intermediate Similarity	NPC9894
0.734	Intermediate Similarity	NPC245816
0.734	Intermediate Similarity	NPC476138
0.733	Intermediate Similarity	NPC6093
0.733	Intermediate Similarity	NPC174672
0.732	Intermediate Similarity	NPC476319
0.7313	Intermediate Similarity	NPC32200
0.731	Intermediate Similarity	NPC469390
0.7304	Intermediate Similarity	NPC36229
0.7304	Intermediate Similarity	NPC476581
0.7304	Intermediate Similarity	NPC16452
0.7302	Intermediate Similarity	NPC34508
0.7297	Intermediate Similarity	NPC177404
0.729	Intermediate Similarity	NPC51388
0.7285	Intermediate Similarity	NPC11408
0.7285	Intermediate Similarity	NPC101350
0.7282	Intermediate Similarity	NPC476465
0.7277	Intermediate Similarity	NPC78609
0.7277	Intermediate Similarity	NPC315957
0.7273	Intermediate Similarity	NPC476287
0.7269	Intermediate Similarity	NPC133609

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 NPC205934 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	703
0.2-0.3	843
0.3-0.4	1438
0.4-0.5	2806
0.5-0.6	2104
0.6-0.7	728
0.7-0.8	109
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD3003	Approved
0.8256	Intermediate Similarity	NPD5658	Approved
0.8191	Intermediate Similarity	NPD5902	Approved
0.8191	Intermediate Similarity	NPD5903	Approved
0.8125	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1768	Approved
0.8105	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4418	Discontinued
0.7892	Intermediate Similarity	NPD6985	Discontinued
0.7865	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7854	Intermediate Similarity	NPD7194	Discontinued
0.7839	Intermediate Similarity	NPD1392	Approved
0.7824	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5632	Approved
0.7789	Intermediate Similarity	NPD8403	Phase 1
0.776	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD5913	Phase 3
0.7755	Intermediate Similarity	NPD3825	Phase 3
0.7746	Intermediate Similarity	NPD7558	Phase 2
0.7685	Intermediate Similarity	NPD5067	Phase 2
0.7685	Intermediate Similarity	NPD6220	Phase 3
0.7685	Intermediate Similarity	NPD5066	Phase 2
0.768	Intermediate Similarity	NPD1038	Approved
0.7663	Intermediate Similarity	NPD1325	Approved
0.7663	Intermediate Similarity	NPD1326	Approved
0.7656	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD5612	Discontinued
0.7606	Intermediate Similarity	NPD3920	Phase 2
0.7588	Intermediate Similarity	NPD4511	Phase 1
0.7574	Intermediate Similarity	NPD7453	Approved
0.7574	Intermediate Similarity	NPD7452	Approved
0.7574	Intermediate Similarity	NPD7222	Phase 2
0.756	Intermediate Similarity	NPD5930	Phase 3
0.7551	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD802	Phase 2
0.7462	Intermediate Similarity	NPD6590	Discontinued
0.7462	Intermediate Similarity	NPD6251	Discontinued
0.7461	Intermediate Similarity	NPD5256	Discontinued
0.7438	Intermediate Similarity	NPD6150	Discontinued
0.7424	Intermediate Similarity	NPD5512	Phase 3
0.7416	Intermediate Similarity	NPD5164	Discontinued
0.7411	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4795	Phase 2
0.7387	Intermediate Similarity	NPD7948	Phase 1
0.7387	Intermediate Similarity	NPD5003	Discontinued
0.7346	Intermediate Similarity	NPD3402	Phase 1
0.7344	Intermediate Similarity	NPD4203	Approved
0.7344	Intermediate Similarity	NPD4204	Approved
0.7337	Intermediate Similarity	NPD6550	Discontinued
0.7333	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4889	Approved
0.7315	Intermediate Similarity	NPD5559	Phase 2
0.7311	Intermediate Similarity	NPD6242	Discontinued
0.7304	Intermediate Similarity	NPD3397	Phase 2
0.7293	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD6208	Discontinued
0.7282	Intermediate Similarity	NPD2187	Approved
0.7282	Intermediate Similarity	NPD2189	Approved
0.7277	Intermediate Similarity	NPD4439	Discontinued
0.7277	Intermediate Similarity	NPD1740	Approved
0.7277	Intermediate Similarity	NPD1739	Approved
0.7268	Intermediate Similarity	NPD5530	Phase 1
0.7265	Intermediate Similarity	NPD6473	Phase 1
0.726	Intermediate Similarity	NPD6494	Phase 2
0.7243	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5429	Discontinued
0.7231	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3814	Phase 1
0.7225	Intermediate Similarity	NPD3816	Phase 1
0.7225	Intermediate Similarity	NPD7069	Discontinued
0.7225	Intermediate Similarity	NPD5482	Discontinued
0.7225	Intermediate Similarity	NPD6202	Discontinued
0.7225	Intermediate Similarity	NPD3815	Phase 1
0.7222	Intermediate Similarity	NPD2334	Discontinued
0.7214	Intermediate Similarity	NPD6988	Phase 1
0.7214	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4952	Phase 3
0.72	Intermediate Similarity	NPD4349	Approved
0.72	Intermediate Similarity	NPD4350	Approved
0.7193	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3503	Approved
0.7188	Intermediate Similarity	NPD3504	Approved
0.7186	Intermediate Similarity	NPD3923	Approved
0.7186	Intermediate Similarity	NPD6569	Phase 2
0.7186	Intermediate Similarity	NPD3922	Approved
0.7186	Intermediate Similarity	NPD3924	Approved
0.7186	Intermediate Similarity	NPD3921	Approved
0.7184	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2565	Phase 2
0.7172	Intermediate Similarity	NPD2564	Approved
0.7171	Intermediate Similarity	NPD6324	Phase 1
0.7169	Intermediate Similarity	NPD6962	Phase 2
0.715	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6790	Phase 1
0.7136	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4885	Approved
0.7131	Intermediate Similarity	NPD8364	Approved
0.7131	Intermediate Similarity	NPD8363	Approved
0.7115	Intermediate Similarity	NPD2916	Discontinued
0.7104	Intermediate Similarity	NPD4373	Phase 2
0.7095	Intermediate Similarity	NPD4502	Phase 2
0.7081	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6243	Phase 3
0.7074	Intermediate Similarity	NPD6244	Phase 3
0.7071	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2749	Discontinued
0.707	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8395	Approved
0.7059	Intermediate Similarity	NPD8396	Approved
0.7049	Intermediate Similarity	NPD3833	Phase 3
0.7049	Intermediate Similarity	NPD3835	Phase 3
0.7045	Intermediate Similarity	NPD5479	Discontinued
0.7039	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3765	Approved
0.7033	Intermediate Similarity	NPD7672	Approved
0.7033	Intermediate Similarity	NPD7671	Approved
0.703	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8428	Approved
0.7025	Intermediate Similarity	NPD8465	Approved
0.7025	Intermediate Similarity	NPD8467	Approved
0.7025	Intermediate Similarity	NPD8427	Approved
0.7025	Intermediate Similarity	NPD8429	Approved
0.7025	Intermediate Similarity	NPD8466	Approved
0.7023	Intermediate Similarity	NPD3875	Discontinued
0.7023	Intermediate Similarity	NPD3763	Approved
0.7019	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7719	Discontinued
0.7009	Intermediate Similarity	NPD7955	Approved
0.7009	Intermediate Similarity	NPD7956	Approved
0.7005	Intermediate Similarity	NPD6991	Approved
0.7005	Intermediate Similarity	NPD7219	Approved
0.7005	Intermediate Similarity	NPD7221	Approved
0.7	Intermediate Similarity	NPD7555	Discontinued
0.6996	Remote Similarity	NPD6964	Approved
0.6996	Remote Similarity	NPD6963	Approved
0.6995	Remote Similarity	NPD5065	Approved
0.6987	Remote Similarity	NPD8358	Approved
0.6986	Remote Similarity	NPD7051	Phase 3
0.6986	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2794	Discontinued
0.6981	Remote Similarity	NPD3330	Phase 1
0.6976	Remote Similarity	NPD4548	Discontinued
0.6974	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4354	Approved
0.6955	Remote Similarity	NPD3259	Approved
0.6948	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6246	Approved
0.6938	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4995	Approved
0.6937	Remote Similarity	NPD4996	Approved
0.6935	Remote Similarity	NPD4919	Phase 3
0.6935	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4921	Phase 3
0.6934	Remote Similarity	NPD5416	Discontinued
0.6927	Remote Similarity	NPD6736	Discontinued
0.6923	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4071	Approved
0.6923	Remote Similarity	NPD4072	Approved
0.6923	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2882	Phase 1
0.6916	Remote Similarity	NPD5293	Phase 2
0.6911	Remote Similarity	NPD8460	Approved
0.6911	Remote Similarity	NPD8426	Approved
0.6911	Remote Similarity	NPD8425	Approved
0.6911	Remote Similarity	NPD8459	Approved
0.6909	Remote Similarity	NPD7426	Phase 1
0.6909	Remote Similarity	NPD7674	Phase 3
0.6909	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7675	Phase 3
0.6904	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3386	Phase 2
0.6903	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4927	Discontinued
0.69	Remote Similarity	NPD6230	Discontinued
0.6892	Remote Similarity	NPD8512	Phase 3
0.6892	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4925	Approved
0.689	Remote Similarity	NPD5901	Discontinued
0.6888	Remote Similarity	NPD8386	Phase 2
0.6884	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD2952	Discontinued
0.6878	Remote Similarity	NPD7994	Phase 2
0.6875	Remote Similarity	NPD1921	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD4463	Approved
0.6865	Remote Similarity	NPD4462	Approved
0.6862	Remote Similarity	NPD5450	Discontinued
0.6862	Remote Similarity	NPD7803	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