NPASS Compound

Structure

CID133698 OpenBabel06191715492D 22 24 0 0 1 0 0 0 0 0999 V2000 1.9297 0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2410 -1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7159 -4.5347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3565 -3.9919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9002 -1.0288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6923 -2.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2560 -3.1923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0342 -0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2946 -0.9705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5249 -3.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 -2.1115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5068 -2.5457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2910 -1.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4769 -1.5461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3232 -0.9463 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9999 -0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2371 -2.9990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4385 -4.3537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5997 0.7852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1567 -3.3921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4204 -2.9524 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 8 1 0 0 0 0 2 9 2 0 0 0 0 3 10 1 0 0 0 0 5 6 1 0 0 0 0 5 8 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 17 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 1 0 0 0 12 14 1 0 0 0 0 12 21 1 6 0 0 0 13 8 1 1 0 0 0 13 15 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 15 22 1 6 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 4 1 1 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.15
Volume:	310.324
LogP:	0.956
LogD:	1.618
LogS:	-2.641
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	4.607
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.759
MDCK Permeability:	9.911535744322464e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.748
20% Bioavailability (F20%):	0.152
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	59.34906005859375%
Volume Distribution (VD):	1.41
Pgp-substrate:	25.157556533813477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.602
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	5.131
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.946
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.555
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.506
Carcinogencity:	0.068
Eye Corrosion:	0.465
Eye Irritation:	0.518
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC133698

Natural Product ID:	NPC133698
*Common Name:**	Cumambrin A
IUPAC Name:	[(3aR,4S,6R,6aR,9aR,9bR)-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] acetate
Synonyms:
Standard InCHIKey:	XMJROHDIQQOWTO-NRPXGKOBSA-N
Standard InCHI:	InChI=1S/C17H22O5/c1-8-5-6-11-13(8)15-14(9(2)16(19)22-15)12(21-10(3)18)7-17(11,4)20/h5,11-15,20H,2,6-7H2,1,3-4H3/t11-,12+,13+,14-,15-,17-/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@@](C)(O)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)C(=CC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL190755
PubChem CID:	174867
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/JMPR.9000078]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[12130858]
NPO23451	Polytrichum commune	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19572610]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21875046]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	whole plant	Taitung County, Taiwan	2009-MAY	PMID[21875046]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26099993]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27715048]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28156114]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29400471]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30726671]
NPO23093	Blumea obliqua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7494149]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23451	Polytrichum commune	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24213	Strophanthus thollonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18436	Agave ghiesbreghtii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21202	Galeopsis pubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26367	Muriceopsis flavida	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24213	Strophanthus thollonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26758	Forsythia x intermedia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23687	Delphinium hybridum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24326	Adenocalymma alliaceum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23451	Polytrichum commune	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18699	Baccharis articulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23093	Blumea obliqua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22967	Maytenus blepharodes	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21955	Salvia deserta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20909	Astragalus amarus	Species	Fabaceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	20.0	uM	PMID[547823]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	pIC100	=	-1.3	n.a.	PMID[547823]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	20.0	uM	PMID[547824]

☑ 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 NPC133698 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	202
0.1-0.2	1195
0.2-0.3	5045
0.3-0.4	11623
0.4-0.5	11942
0.5-0.6	7511
0.6-0.7	3907
0.7-0.8	1029
0.8-0.85	201
0.85-0.9	21
0.9-0.95	8
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC477131
0.977	High Similarity	NPC198853
0.9767	High Similarity	NPC131209
0.9545	High Similarity	NPC470010
0.9545	High Similarity	NPC262133
0.9545	High Similarity	NPC470013
0.9545	High Similarity	NPC323008
0.9419	High Similarity	NPC91248
0.9222	High Similarity	NPC67584
0.9222	High Similarity	NPC304886
0.9121	High Similarity	NPC213078
0.9091	High Similarity	NPC4986
0.9043	High Similarity	NPC86077
0.9022	High Similarity	NPC161493
0.9011	High Similarity	NPC52044
0.9	High Similarity	NPC135776
0.8977	High Similarity	NPC79549
0.8901	High Similarity	NPC127019
0.8876	High Similarity	NPC215556
0.8804	High Similarity	NPC213698
0.8778	High Similarity	NPC216284
0.8778	High Similarity	NPC37607
0.8778	High Similarity	NPC301969
0.8764	High Similarity	NPC207114
0.8764	High Similarity	NPC178875
0.8764	High Similarity	NPC217983
0.8763	High Similarity	NPC223450
0.8763	High Similarity	NPC243998
0.8763	High Similarity	NPC166115
0.875	High Similarity	NPC67493
0.8723	High Similarity	NPC221615
0.8706	High Similarity	NPC276356
0.8681	High Similarity	NPC155215
0.8681	High Similarity	NPC475925
0.8681	High Similarity	NPC184063
0.8667	High Similarity	NPC32922
0.8652	High Similarity	NPC118601
0.8636	High Similarity	NPC204105
0.8636	High Similarity	NPC284534
0.8636	High Similarity	NPC235792
0.8636	High Similarity	NPC300082
0.8602	High Similarity	NPC163228
0.8602	High Similarity	NPC472873
0.8602	High Similarity	NPC170120
0.8587	High Similarity	NPC258216
0.8571	High Similarity	NPC54065
0.8571	High Similarity	NPC297474
0.8571	High Similarity	NPC19087
0.8556	High Similarity	NPC202672
0.8542	High Similarity	NPC150923
0.8539	High Similarity	NPC64153
0.8539	High Similarity	NPC187661
0.8539	High Similarity	NPC107787
0.8523	High Similarity	NPC156485
0.8523	High Similarity	NPC115786
0.8511	High Similarity	NPC18019
0.8511	High Similarity	NPC24956
0.8506	High Similarity	NPC246076
0.8495	Intermediate Similarity	NPC474338
0.8485	Intermediate Similarity	NPC26617
0.8478	Intermediate Similarity	NPC12172
0.8478	Intermediate Similarity	NPC35959
0.8478	Intermediate Similarity	NPC293001
0.8478	Intermediate Similarity	NPC184463
0.8478	Intermediate Similarity	NPC171360
0.8478	Intermediate Similarity	NPC208886
0.8478	Intermediate Similarity	NPC133888
0.8478	Intermediate Similarity	NPC63193
0.8478	Intermediate Similarity	NPC29821
0.8478	Intermediate Similarity	NPC57304
0.8462	Intermediate Similarity	NPC38392
0.8462	Intermediate Similarity	NPC155935
0.8462	Intermediate Similarity	NPC472872
0.8462	Intermediate Similarity	NPC307411
0.8444	Intermediate Similarity	NPC160138
0.8427	Intermediate Similarity	NPC78089
0.8421	Intermediate Similarity	NPC213947
0.8421	Intermediate Similarity	NPC170143
0.8421	Intermediate Similarity	NPC108475
0.8416	Intermediate Similarity	NPC471884
0.8409	Intermediate Similarity	NPC245665
0.8409	Intermediate Similarity	NPC250315
0.8404	Intermediate Similarity	NPC476053
0.8387	Intermediate Similarity	NPC228451
0.8387	Intermediate Similarity	NPC473273
0.8387	Intermediate Similarity	NPC476300
0.8387	Intermediate Similarity	NPC475912
0.8387	Intermediate Similarity	NPC308656
0.8387	Intermediate Similarity	NPC473234
0.8387	Intermediate Similarity	NPC475838
0.8387	Intermediate Similarity	NPC179746
0.8387	Intermediate Similarity	NPC473263
0.8387	Intermediate Similarity	NPC81419
0.8387	Intermediate Similarity	NPC212486
0.8387	Intermediate Similarity	NPC125674
0.8387	Intermediate Similarity	NPC60386
0.837	Intermediate Similarity	NPC35809
0.837	Intermediate Similarity	NPC129419
0.837	Intermediate Similarity	NPC51004
0.837	Intermediate Similarity	NPC144133
0.837	Intermediate Similarity	NPC179394
0.837	Intermediate Similarity	NPC475855
0.8367	Intermediate Similarity	NPC124881
0.8352	Intermediate Similarity	NPC224652
0.8333	Intermediate Similarity	NPC162071
0.8333	Intermediate Similarity	NPC50637
0.8333	Intermediate Similarity	NPC304558
0.8333	Intermediate Similarity	NPC470242
0.8333	Intermediate Similarity	NPC236692
0.8333	Intermediate Similarity	NPC309757
0.8315	Intermediate Similarity	NPC165287
0.8315	Intermediate Similarity	NPC224386
0.8315	Intermediate Similarity	NPC194859
0.8298	Intermediate Similarity	NPC474247
0.8298	Intermediate Similarity	NPC167219
0.8295	Intermediate Similarity	NPC89555
0.8283	Intermediate Similarity	NPC203659
0.8283	Intermediate Similarity	NPC100487
0.828	Intermediate Similarity	NPC30515
0.8276	Intermediate Similarity	NPC69271
0.8276	Intermediate Similarity	NPC74673
0.8265	Intermediate Similarity	NPC474747
0.8265	Intermediate Similarity	NPC225353
0.8261	Intermediate Similarity	NPC268298
0.8261	Intermediate Similarity	NPC295312
0.8252	Intermediate Similarity	NPC258711
0.8252	Intermediate Similarity	NPC95290
0.8252	Intermediate Similarity	NPC35069
0.8252	Intermediate Similarity	NPC189338
0.8247	Intermediate Similarity	NPC70865
0.8247	Intermediate Similarity	NPC186861
0.8242	Intermediate Similarity	NPC190753
0.8242	Intermediate Similarity	NPC24728
0.8229	Intermediate Similarity	NPC471150
0.8229	Intermediate Similarity	NPC474313
0.8229	Intermediate Similarity	NPC169205
0.8229	Intermediate Similarity	NPC181151
0.8222	Intermediate Similarity	NPC255307
0.8222	Intermediate Similarity	NPC215364
0.8222	Intermediate Similarity	NPC165162
0.8211	Intermediate Similarity	NPC224689
0.8211	Intermediate Similarity	NPC48803
0.8211	Intermediate Similarity	NPC90121
0.8211	Intermediate Similarity	NPC270013
0.8211	Intermediate Similarity	NPC14961
0.8211	Intermediate Similarity	NPC193645
0.8211	Intermediate Similarity	NPC275960
0.8211	Intermediate Similarity	NPC36954
0.8202	Intermediate Similarity	NPC272814
0.8202	Intermediate Similarity	NPC128246
0.8202	Intermediate Similarity	NPC111409
0.82	Intermediate Similarity	NPC475217
0.82	Intermediate Similarity	NPC54737
0.8191	Intermediate Similarity	NPC472874
0.8191	Intermediate Similarity	NPC153590
0.8182	Intermediate Similarity	NPC301477
0.8182	Intermediate Similarity	NPC25684
0.8182	Intermediate Similarity	NPC110989
0.8182	Intermediate Similarity	NPC475945
0.8182	Intermediate Similarity	NPC39411
0.8182	Intermediate Similarity	NPC255580
0.8182	Intermediate Similarity	NPC475871
0.8182	Intermediate Similarity	NPC141810
0.8182	Intermediate Similarity	NPC281949
0.8173	Intermediate Similarity	NPC209058
0.8172	Intermediate Similarity	NPC62815
0.8163	Intermediate Similarity	NPC474742
0.8163	Intermediate Similarity	NPC171759
0.8161	Intermediate Similarity	NPC617
0.8161	Intermediate Similarity	NPC470239
0.8161	Intermediate Similarity	NPC182550
0.8161	Intermediate Similarity	NPC470244
0.8152	Intermediate Similarity	NPC471149
0.8144	Intermediate Similarity	NPC45125
0.8144	Intermediate Similarity	NPC187268
0.8144	Intermediate Similarity	NPC141191
0.814	Intermediate Similarity	NPC470240
0.814	Intermediate Similarity	NPC476794
0.8132	Intermediate Similarity	NPC475461
0.8132	Intermediate Similarity	NPC56593
0.8132	Intermediate Similarity	NPC150755
0.8132	Intermediate Similarity	NPC305475
0.8132	Intermediate Similarity	NPC284902
0.8125	Intermediate Similarity	NPC230800
0.8125	Intermediate Similarity	NPC142529
0.8125	Intermediate Similarity	NPC279621
0.8125	Intermediate Similarity	NPC476315
0.8125	Intermediate Similarity	NPC91771
0.8125	Intermediate Similarity	NPC185553
0.8111	Intermediate Similarity	NPC191476
0.8111	Intermediate Similarity	NPC114979
0.8111	Intermediate Similarity	NPC476804
0.8105	Intermediate Similarity	NPC81386
0.8105	Intermediate Similarity	NPC474035
0.81	Intermediate Similarity	NPC474741
0.8085	Intermediate Similarity	NPC111114
0.8085	Intermediate Similarity	NPC261607
0.8085	Intermediate Similarity	NPC74103
0.8085	Intermediate Similarity	NPC300312
0.8085	Intermediate Similarity	NPC123177

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 NPC133698 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1824
0.2-0.3	3769
0.3-0.4	2323
0.4-0.5	644
0.5-0.6	325
0.6-0.7	65
0.7-0.8	10
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD1695	Approved
0.8485	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6371	Approved
0.7634	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5282	Discontinued
0.7423	Intermediate Similarity	NPD6698	Approved
0.7423	Intermediate Similarity	NPD46	Approved
0.7419	Intermediate Similarity	NPD5362	Discontinued
0.7407	Intermediate Similarity	NPD6053	Discontinued
0.7368	Intermediate Similarity	NPD4249	Approved
0.7292	Intermediate Similarity	NPD4251	Approved
0.7292	Intermediate Similarity	NPD4250	Approved
0.7263	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7154	Phase 3
0.7071	Intermediate Similarity	NPD5785	Approved
0.7071	Intermediate Similarity	NPD7838	Discovery
0.7021	Intermediate Similarity	NPD5369	Approved
0.6947	Remote Similarity	NPD6435	Approved
0.6931	Remote Similarity	NPD6399	Phase 3
0.6915	Remote Similarity	NPD4820	Approved
0.6915	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD4819	Approved
0.6915	Remote Similarity	NPD4821	Approved
0.6907	Remote Similarity	NPD5363	Approved
0.6881	Remote Similarity	NPD6686	Approved
0.6852	Remote Similarity	NPD6008	Approved
0.6847	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7983	Approved
0.6771	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4270	Approved
0.6771	Remote Similarity	NPD4269	Approved
0.6765	Remote Similarity	NPD5778	Approved
0.6765	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD4225	Approved
0.6762	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7638	Approved
0.6737	Remote Similarity	NPD5368	Approved
0.6735	Remote Similarity	NPD1694	Approved
0.6702	Remote Similarity	NPD4268	Approved
0.6702	Remote Similarity	NPD4271	Approved
0.6702	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5331	Approved
0.6701	Remote Similarity	NPD5332	Approved
0.6698	Remote Similarity	NPD7640	Approved
0.6698	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD5786	Approved
0.6636	Remote Similarity	NPD5344	Discontinued
0.6635	Remote Similarity	NPD5695	Phase 3
0.6604	Remote Similarity	NPD5696	Approved
0.6562	Remote Similarity	NPD4252	Approved
0.6552	Remote Similarity	NPD7115	Discovery
0.6542	Remote Similarity	NPD6648	Approved
0.6509	Remote Similarity	NPD6083	Phase 2
0.6509	Remote Similarity	NPD6084	Phase 2
0.6505	Remote Similarity	NPD7637	Suspended
0.6486	Remote Similarity	NPD5697	Approved
0.6471	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6101	Approved
0.6465	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD6881	Approved
0.6429	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD5209	Approved
0.6404	Remote Similarity	NPD6649	Approved
0.6404	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD5739	Approved
0.6396	Remote Similarity	NPD6675	Approved
0.6396	Remote Similarity	NPD7128	Approved
0.6393	Remote Similarity	NPD7507	Approved
0.6372	Remote Similarity	NPD6014	Approved
0.6372	Remote Similarity	NPD6373	Approved
0.6372	Remote Similarity	NPD6012	Approved
0.6372	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6372	Approved
0.6372	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD6695	Phase 3
0.6346	Remote Similarity	NPD5281	Approved
0.6346	Remote Similarity	NPD5693	Phase 1
0.6346	Remote Similarity	NPD6411	Approved
0.6346	Remote Similarity	NPD5284	Approved
0.6339	Remote Similarity	NPD5701	Approved
0.6333	Remote Similarity	NPD8515	Approved
0.6333	Remote Similarity	NPD8516	Approved
0.6333	Remote Similarity	NPD8513	Phase 3
0.6333	Remote Similarity	NPD8517	Approved
0.6321	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD7290	Approved
0.6316	Remote Similarity	NPD6883	Approved
0.6311	Remote Similarity	NPD7492	Approved
0.6293	Remote Similarity	NPD4632	Approved
0.6292	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6011	Approved
0.6262	Remote Similarity	NPD7839	Suspended
0.6261	Remote Similarity	NPD8130	Phase 1
0.6261	Remote Similarity	NPD6847	Approved
0.6261	Remote Similarity	NPD6869	Approved
0.6261	Remote Similarity	NPD6617	Approved
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD5207	Approved
0.625	Remote Similarity	NPD6319	Approved
0.624	Remote Similarity	NPD7319	Approved
0.6214	Remote Similarity	NPD6672	Approved
0.6214	Remote Similarity	NPD6903	Approved
0.6214	Remote Similarity	NPD5737	Approved
0.621	Remote Similarity	NPD7078	Approved
0.6207	Remote Similarity	NPD6882	Approved
0.6207	Remote Similarity	NPD8297	Approved
0.6204	Remote Similarity	NPD7902	Approved
0.6198	Remote Similarity	NPD6016	Approved
0.6198	Remote Similarity	NPD6015	Approved
0.6195	Remote Similarity	NPD6412	Phase 2
0.6195	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8035	Phase 2
0.619	Remote Similarity	NPD8034	Phase 2
0.6176	Remote Similarity	NPD5330	Approved
0.6176	Remote Similarity	NPD6684	Approved
0.6176	Remote Similarity	NPD7521	Approved
0.6176	Remote Similarity	NPD7334	Approved
0.6176	Remote Similarity	NPD6409	Approved
0.6176	Remote Similarity	NPD7146	Approved
0.6168	Remote Similarity	NPD5210	Approved
0.6168	Remote Similarity	NPD4629	Approved
0.616	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD4753	Phase 2
0.6148	Remote Similarity	NPD5988	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.6139	Remote Similarity	NPD4786	Approved
0.6134	Remote Similarity	NPD6009	Approved
0.6126	Remote Similarity	NPD5211	Phase 2
0.6126	Remote Similarity	NPD7632	Discontinued
0.6117	Remote Similarity	NPD7524	Approved
0.6117	Remote Similarity	NPD7750	Discontinued
0.6116	Remote Similarity	NPD6059	Approved
0.61	Remote Similarity	NPD3667	Approved
0.6091	Remote Similarity	NPD4696	Approved
0.6091	Remote Similarity	NPD5285	Approved
0.6091	Remote Similarity	NPD5286	Approved
0.6083	Remote Similarity	NPD7328	Approved
0.6083	Remote Similarity	NPD7327	Approved
0.608	Remote Similarity	NPD8293	Discontinued
0.608	Remote Similarity	NPD8074	Phase 3
0.6075	Remote Similarity	NPD6001	Approved
0.6075	Remote Similarity	NPD7748	Approved
0.6066	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5983	Phase 2
0.6066	Remote Similarity	NPD8033	Approved
0.6061	Remote Similarity	NPD6930	Phase 2
0.6061	Remote Similarity	NPD6931	Approved
0.6058	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4755	Approved
0.605	Remote Similarity	NPD6274	Approved
0.6042	Remote Similarity	NPD8039	Approved
0.6033	Remote Similarity	NPD7516	Approved
0.6019	Remote Similarity	NPD3618	Phase 1
0.6019	Remote Similarity	NPD5279	Phase 3
0.6018	Remote Similarity	NPD5141	Approved
0.6017	Remote Similarity	NPD8133	Approved
0.6016	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD8377	Approved
0.5984	Remote Similarity	NPD8294	Approved
0.5983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD2204	Approved
0.5982	Remote Similarity	NPD4633	Approved
0.5982	Remote Similarity	NPD5224	Approved
0.5982	Remote Similarity	NPD5225	Approved
0.5982	Remote Similarity	NPD5226	Approved
0.5981	Remote Similarity	NPD4202	Approved
0.598	Remote Similarity	NPD3665	Phase 1
0.598	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3133	Approved
0.598	Remote Similarity	NPD3666	Approved
0.5969	Remote Similarity	NPD6845	Suspended
0.5968	Remote Similarity	NPD7604	Phase 2
0.596	Remote Similarity	NPD6929	Approved
0.5946	Remote Similarity	NPD4700	Approved
0.5943	Remote Similarity	NPD5692	Phase 3
0.5941	Remote Similarity	NPD4221	Approved
0.5941	Remote Similarity	NPD4223	Phase 3
0.5941	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8296	Approved
0.5935	Remote Similarity	NPD7503	Approved
0.5935	Remote Similarity	NPD8379	Approved
0.5935	Remote Similarity	NPD8380	Approved
0.5935	Remote Similarity	NPD8335	Approved
0.5935	Remote Similarity	NPD8378	Approved
0.5929	Remote Similarity	NPD5174	Approved
0.5929	Remote Similarity	NPD5175	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