NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.16
Volume:	245.946
LogP:	1.484
LogD:	1.228
LogS:	-2.075
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	4.218
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.365
MDCK Permeability:	2.019227758864872e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.464
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.885
Plasma Protein Binding (PPB):	62.685523986816406%
Volume Distribution (VD):	0.7
Pgp-substrate:	38.32753372192383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.575
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.294
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.493

ADMET: Excretion

Clearance (CL):	6.947
Half-life (T1/2):	0.703

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.138
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.696
Skin Sensitization:	0.707
Carcinogencity:	0.865
Eye Corrosion:	0.742
Eye Irritation:	0.975
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC85105

Natural Product ID:	NPC85105
*Common Name:**	Boscialin
IUPAC Name:	(E)-4-[(1S,4S,6R)-1,4-dihydroxy-2,2,6-trimethylcyclohexyl]but-3-en-2-one
Synonyms:
Standard InCHIKey:	CWLKAPCFJXJCEO-SGEPYOGPSA-N
Standard InCHI:	InChI=1S/C13H22O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-6,9,11,15-16H,7-8H2,1-4H3/b6-5+/t9-,11+,13-/m1/s1
SMILES:	O[C@H]1C[C@@H](C)[C@](C(C1)(C)C)(O)/C=C/C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517695
PubChem CID:	6442487
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/JMPR.9000078]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	fruit	n.a.	PMID[10820058]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[12130858]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16441086]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26099993]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28156114]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
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]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Unripe fruit	n.a.	n.a.	PMID[9644064]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29067	Spondias dulcis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10669	Cousinia pterocaulos	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20117	Leucas lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22906	Bouchardatia neurococca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22204	Tylostylis discolor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4954	Eleutherococcus divaricatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3683.1	Pteridium aquilinum subsp. latiusculum	Subspecies	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22779	Sphagnum magellanicum	Species	Sphagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23009	Udotea flabellum	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22962	Coussarea hydrangeifolia	Species	Rubiaceae	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
MIC	3
Others	7

Activity Type	# Activity
Cell Line	2
Organism	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	MIC	>	100.0	ug.mL-1	PMID[570270]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	43.0	ug.mL-1	PMID[570270]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	MIC	=	11.0	ug.mL-1	PMID[570270]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	1.9	ug.mL-1	PMID[570270]
NPT2	Others	Unspecified		Ratio IC50	=	23.0	n.a.	PMID[570270]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	2.5	mm	PMID[570270]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	=	0.0	mm	PMID[570270]
NPT3987	Organism	Corynebacterium xerosis	Corynebacterium xerosis	IZ	=	2.0	mm	PMID[570270]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	1.0	mm	PMID[570270]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	5.0	mm	PMID[570270]
NPT3988	Organism	Corynebacterium minutissimum	Corynebacterium minutissimum	IZ	=	9.5	mm	PMID[570270]

☑ 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 NPC85105 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	158
0.1-0.2	1342
0.2-0.3	5571
0.3-0.4	14653
0.4-0.5	10567
0.5-0.6	6965
0.6-0.7	3011
0.7-0.8	404
0.8-0.85	20
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC149550
0.9028	High Similarity	NPC471272
0.8987	High Similarity	NPC471267
0.8611	High Similarity	NPC471238
0.85	High Similarity	NPC471987
0.8312	Intermediate Similarity	NPC167873
0.8312	Intermediate Similarity	NPC1973
0.8272	Intermediate Similarity	NPC79945
0.8267	Intermediate Similarity	NPC471271
0.8267	Intermediate Similarity	NPC471268
0.8205	Intermediate Similarity	NPC203403
0.8171	Intermediate Similarity	NPC40687
0.8125	Intermediate Similarity	NPC471266
0.8125	Intermediate Similarity	NPC281880
0.8125	Intermediate Similarity	NPC95124
0.8108	Intermediate Similarity	NPC117804
0.8072	Intermediate Similarity	NPC109528
0.8052	Intermediate Similarity	NPC22134
0.8026	Intermediate Similarity	NPC477792
0.8026	Intermediate Similarity	NPC164022
0.8026	Intermediate Similarity	NPC23954
0.8025	Intermediate Similarity	NPC159148
0.8025	Intermediate Similarity	NPC471270
0.8023	Intermediate Similarity	NPC134321
0.8	Intermediate Similarity	NPC471791
0.8	Intermediate Similarity	NPC471793
0.8	Intermediate Similarity	NPC308038
0.8	Intermediate Similarity	NPC470429
0.7976	Intermediate Similarity	NPC472974
0.7975	Intermediate Similarity	NPC470428
0.7927	Intermediate Similarity	NPC93590
0.7927	Intermediate Similarity	NPC2524
0.7907	Intermediate Similarity	NPC472973
0.7907	Intermediate Similarity	NPC472983
0.7901	Intermediate Similarity	NPC471514
0.7901	Intermediate Similarity	NPC236707
0.7875	Intermediate Similarity	NPC476949
0.7848	Intermediate Similarity	NPC265588
0.7848	Intermediate Similarity	NPC250621
0.7831	Intermediate Similarity	NPC251475
0.7831	Intermediate Similarity	NPC57370
0.7831	Intermediate Similarity	NPC169941
0.7821	Intermediate Similarity	NPC476366
0.7821	Intermediate Similarity	NPC78527
0.7821	Intermediate Similarity	NPC201048
0.7816	Intermediate Similarity	NPC128672
0.7792	Intermediate Similarity	NPC95863
0.7778	Intermediate Similarity	NPC170394
0.7765	Intermediate Similarity	NPC475069
0.7765	Intermediate Similarity	NPC472986
0.7765	Intermediate Similarity	NPC472985
0.7765	Intermediate Similarity	NPC175145
0.7753	Intermediate Similarity	NPC299100
0.775	Intermediate Similarity	NPC476007
0.775	Intermediate Similarity	NPC470711
0.775	Intermediate Similarity	NPC470758
0.7738	Intermediate Similarity	NPC302360
0.7727	Intermediate Similarity	NPC473675
0.7727	Intermediate Similarity	NPC472978
0.7711	Intermediate Similarity	NPC92226
0.7711	Intermediate Similarity	NPC259858
0.7701	Intermediate Similarity	NPC257485
0.7692	Intermediate Similarity	NPC186042
0.7692	Intermediate Similarity	NPC220939
0.7692	Intermediate Similarity	NPC265485
0.7683	Intermediate Similarity	NPC148685
0.7683	Intermediate Similarity	NPC104120
0.7683	Intermediate Similarity	NPC157895
0.7683	Intermediate Similarity	NPC96362
0.7683	Intermediate Similarity	NPC172013
0.7667	Intermediate Similarity	NPC180950
0.7667	Intermediate Similarity	NPC476245
0.7662	Intermediate Similarity	NPC92801
0.7654	Intermediate Similarity	NPC11908
0.7654	Intermediate Similarity	NPC475994
0.7654	Intermediate Similarity	NPC62336
0.7647	Intermediate Similarity	NPC476426
0.7647	Intermediate Similarity	NPC22133
0.7634	Intermediate Similarity	NPC115862
0.7632	Intermediate Similarity	NPC96484
0.7625	Intermediate Similarity	NPC263582
0.7625	Intermediate Similarity	NPC470749
0.7625	Intermediate Similarity	NPC253190
0.7619	Intermediate Similarity	NPC64600
0.7619	Intermediate Similarity	NPC476927
0.7619	Intermediate Similarity	NPC185605
0.7614	Intermediate Similarity	NPC230332
0.7595	Intermediate Similarity	NPC306727
0.7595	Intermediate Similarity	NPC227814
0.7595	Intermediate Similarity	NPC144995
0.759	Intermediate Similarity	NPC170303
0.759	Intermediate Similarity	NPC249423
0.759	Intermediate Similarity	NPC6663
0.759	Intermediate Similarity	NPC476646
0.7586	Intermediate Similarity	NPC229612
0.7586	Intermediate Similarity	NPC7280
0.7586	Intermediate Similarity	NPC104560
0.7564	Intermediate Similarity	NPC167706
0.7561	Intermediate Similarity	NPC281138
0.7558	Intermediate Similarity	NPC194417
0.7558	Intermediate Similarity	NPC179591
0.7556	Intermediate Similarity	NPC472976
0.7556	Intermediate Similarity	NPC472977
0.7556	Intermediate Similarity	NPC196227
0.7553	Intermediate Similarity	NPC150463
0.7553	Intermediate Similarity	NPC214277
0.7532	Intermediate Similarity	NPC9942
0.7531	Intermediate Similarity	NPC197659
0.7531	Intermediate Similarity	NPC132542
0.7531	Intermediate Similarity	NPC74995
0.7531	Intermediate Similarity	NPC91594
0.7531	Intermediate Similarity	NPC257666
0.7531	Intermediate Similarity	NPC266193
0.7529	Intermediate Similarity	NPC306951
0.7529	Intermediate Similarity	NPC476412
0.7528	Intermediate Similarity	NPC116726
0.7528	Intermediate Similarity	NPC475806
0.7528	Intermediate Similarity	NPC252433
0.7528	Intermediate Similarity	NPC472975
0.75	Intermediate Similarity	NPC87489
0.75	Intermediate Similarity	NPC472240
0.75	Intermediate Similarity	NPC218616
0.75	Intermediate Similarity	NPC139207
0.75	Intermediate Similarity	NPC314727
0.75	Intermediate Similarity	NPC262858
0.75	Intermediate Similarity	NPC82876
0.75	Intermediate Similarity	NPC256112
0.75	Intermediate Similarity	NPC32832
0.75	Intermediate Similarity	NPC185874
0.75	Intermediate Similarity	NPC133580
0.75	Intermediate Similarity	NPC291503
0.75	Intermediate Similarity	NPC296701
0.7473	Intermediate Similarity	NPC259286
0.7473	Intermediate Similarity	NPC316215
0.747	Intermediate Similarity	NPC472301
0.747	Intermediate Similarity	NPC469637
0.7468	Intermediate Similarity	NPC323437
0.7468	Intermediate Similarity	NPC201562
0.7468	Intermediate Similarity	NPC29542
0.7468	Intermediate Similarity	NPC68443
0.7468	Intermediate Similarity	NPC247586
0.7447	Intermediate Similarity	NPC470184
0.7436	Intermediate Similarity	NPC34834
0.7432	Intermediate Similarity	NPC83200
0.7419	Intermediate Similarity	NPC316598
0.7416	Intermediate Similarity	NPC182136
0.7416	Intermediate Similarity	NPC310479
0.7412	Intermediate Similarity	NPC105173
0.7412	Intermediate Similarity	NPC82623
0.7412	Intermediate Similarity	NPC243347
0.7407	Intermediate Similarity	NPC106432
0.7407	Intermediate Similarity	NPC472305
0.7396	Intermediate Similarity	NPC118911
0.7391	Intermediate Similarity	NPC301534
0.7391	Intermediate Similarity	NPC250757
0.7391	Intermediate Similarity	NPC249954
0.7386	Intermediate Similarity	NPC58271
0.7386	Intermediate Similarity	NPC291665
0.7386	Intermediate Similarity	NPC158778
0.7381	Intermediate Similarity	NPC226068
0.7381	Intermediate Similarity	NPC6434
0.7375	Intermediate Similarity	NPC91858
0.7375	Intermediate Similarity	NPC215050
0.7375	Intermediate Similarity	NPC477138
0.7375	Intermediate Similarity	NPC243342
0.7363	Intermediate Similarity	NPC105490
0.7363	Intermediate Similarity	NPC201725
0.7363	Intermediate Similarity	NPC119562
0.7363	Intermediate Similarity	NPC474690
0.7363	Intermediate Similarity	NPC8993
0.7363	Intermediate Similarity	NPC279410
0.7363	Intermediate Similarity	NPC103527
0.7356	Intermediate Similarity	NPC131813
0.7356	Intermediate Similarity	NPC473226
0.7356	Intermediate Similarity	NPC476043
0.7356	Intermediate Similarity	NPC299068
0.7349	Intermediate Similarity	NPC152061
0.7349	Intermediate Similarity	NPC19900
0.7342	Intermediate Similarity	NPC110799
0.7333	Intermediate Similarity	NPC225415
0.7333	Intermediate Similarity	NPC74296
0.7333	Intermediate Similarity	NPC78594
0.7333	Intermediate Similarity	NPC110923
0.7333	Intermediate Similarity	NPC300593
0.7333	Intermediate Similarity	NPC73457
0.7333	Intermediate Similarity	NPC212948
0.7326	Intermediate Similarity	NPC251170
0.7326	Intermediate Similarity	NPC33913
0.7326	Intermediate Similarity	NPC231310
0.7326	Intermediate Similarity	NPC102048
0.7317	Intermediate Similarity	NPC34110
0.7317	Intermediate Similarity	NPC283619
0.7312	Intermediate Similarity	NPC99726
0.7312	Intermediate Similarity	NPC120446
0.7312	Intermediate Similarity	NPC474785
0.7312	Intermediate Similarity	NPC474938
0.7308	Intermediate Similarity	NPC210323
0.7308	Intermediate Similarity	NPC471560
0.7308	Intermediate Similarity	NPC474248
0.7303	Intermediate Similarity	NPC146554

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 NPC85105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1868
0.2-0.3	4106
0.3-0.4	2194
0.4-0.5	468
0.5-0.6	241
0.6-0.7	123
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7241	Intermediate Similarity	NPD1696	Phase 3
0.7188	Intermediate Similarity	NPD5211	Phase 2
0.7159	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD6079	Approved
0.7073	Intermediate Similarity	NPD8264	Approved
0.7067	Intermediate Similarity	NPD368	Approved
0.7065	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD7525	Registered
0.7041	Intermediate Similarity	NPD5141	Approved
0.6979	Remote Similarity	NPD5286	Approved
0.6979	Remote Similarity	NPD5285	Approved
0.6979	Remote Similarity	NPD4696	Approved
0.6941	Remote Similarity	NPD4195	Approved
0.6923	Remote Similarity	NPD5328	Approved
0.6907	Remote Similarity	NPD5223	Approved
0.6907	Remote Similarity	NPD5344	Discontinued
0.6875	Remote Similarity	NPD4225	Approved
0.6842	Remote Similarity	NPD5221	Approved
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6837	Remote Similarity	NPD5224	Approved
0.6837	Remote Similarity	NPD5226	Approved
0.6837	Remote Similarity	NPD4633	Approved
0.6837	Remote Similarity	NPD5225	Approved
0.6778	Remote Similarity	NPD4623	Approved
0.6778	Remote Similarity	NPD4519	Discontinued
0.6774	Remote Similarity	NPD7515	Phase 2
0.6771	Remote Similarity	NPD4755	Approved
0.6771	Remote Similarity	NPD5173	Approved
0.6768	Remote Similarity	NPD5174	Approved
0.6768	Remote Similarity	NPD5175	Approved
0.6744	Remote Similarity	NPD7645	Phase 2
0.6742	Remote Similarity	NPD3665	Phase 1
0.6742	Remote Similarity	NPD3133	Approved
0.6742	Remote Similarity	NPD3666	Approved
0.6705	Remote Similarity	NPD3667	Approved
0.6701	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD1694	Approved
0.6633	Remote Similarity	NPD7640	Approved
0.6633	Remote Similarity	NPD7639	Approved
0.6633	Remote Similarity	NPD6648	Approved
0.6633	Remote Similarity	NPD4700	Approved
0.6628	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5279	Phase 3
0.6588	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5697	Approved
0.6556	Remote Similarity	NPD4786	Approved
0.6548	Remote Similarity	NPD6926	Approved
0.6548	Remote Similarity	NPD6924	Approved
0.6531	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4730	Approved
0.6505	Remote Similarity	NPD6881	Approved
0.6505	Remote Similarity	NPD6899	Approved
0.6505	Remote Similarity	NPD4729	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6495	Remote Similarity	NPD4697	Phase 3
0.6477	Remote Similarity	NPD7514	Phase 3
0.6477	Remote Similarity	NPD6930	Phase 2
0.6477	Remote Similarity	NPD7509	Discontinued
0.6477	Remote Similarity	NPD6931	Approved
0.6477	Remote Similarity	NPD4695	Discontinued
0.6477	Remote Similarity	NPD7332	Phase 2
0.6471	Remote Similarity	NPD7339	Approved
0.6471	Remote Similarity	NPD6942	Approved
0.6458	Remote Similarity	NPD7748	Approved
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6437	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4754	Approved
0.6429	Remote Similarity	NPD7902	Approved
0.6413	Remote Similarity	NPD5690	Phase 2
0.6395	Remote Similarity	NPD6933	Approved
0.6392	Remote Similarity	NPD4629	Approved
0.6392	Remote Similarity	NPD5210	Approved
0.6383	Remote Similarity	NPD4753	Phase 2
0.6381	Remote Similarity	NPD7102	Approved
0.6381	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4634	Approved
0.6381	Remote Similarity	NPD5251	Approved
0.6381	Remote Similarity	NPD5135	Approved
0.6381	Remote Similarity	NPD6883	Approved
0.6381	Remote Similarity	NPD5247	Approved
0.6381	Remote Similarity	NPD5249	Phase 3
0.6381	Remote Similarity	NPD7290	Approved
0.6381	Remote Similarity	NPD5248	Approved
0.6381	Remote Similarity	NPD5250	Approved
0.6381	Remote Similarity	NPD5169	Approved
0.6374	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6929	Approved
0.6346	Remote Similarity	NPD5128	Approved
0.6344	Remote Similarity	NPD3573	Approved
0.6333	Remote Similarity	NPD4221	Approved
0.6333	Remote Similarity	NPD4223	Phase 3
0.633	Remote Similarity	NPD7115	Discovery
0.6321	Remote Similarity	NPD6649	Approved
0.6321	Remote Similarity	NPD6869	Approved
0.6321	Remote Similarity	NPD5127	Approved
0.6321	Remote Similarity	NPD8130	Phase 1
0.6321	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD6617	Approved
0.6321	Remote Similarity	NPD5216	Approved
0.6321	Remote Similarity	NPD5215	Approved
0.6321	Remote Similarity	NPD6847	Approved
0.6321	Remote Similarity	NPD5217	Approved
0.6316	Remote Similarity	NPD5785	Approved
0.6311	Remote Similarity	NPD5739	Approved
0.6311	Remote Similarity	NPD6402	Approved
0.6311	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD4768	Approved
0.6311	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD7128	Approved
0.631	Remote Similarity	NPD7150	Approved
0.631	Remote Similarity	NPD7152	Approved
0.631	Remote Similarity	NPD7151	Approved
0.6304	Remote Similarity	NPD5363	Approved
0.6292	Remote Similarity	NPD4819	Approved
0.6292	Remote Similarity	NPD4822	Approved
0.6292	Remote Similarity	NPD4748	Discontinued
0.6292	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4821	Approved
0.6292	Remote Similarity	NPD4820	Approved
0.6267	Remote Similarity	NPD342	Phase 1
0.6264	Remote Similarity	NPD6695	Phase 3
0.6262	Remote Similarity	NPD6882	Approved
0.6262	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD7145	Approved
0.6222	Remote Similarity	NPD6902	Approved
0.6204	Remote Similarity	NPD4632	Approved
0.6196	Remote Similarity	NPD4197	Approved
0.619	Remote Similarity	NPD7143	Approved
0.619	Remote Similarity	NPD5168	Approved
0.619	Remote Similarity	NPD7320	Approved
0.619	Remote Similarity	NPD7144	Approved
0.6176	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5167	Approved
0.6136	Remote Similarity	NPD6932	Approved
0.6136	Remote Similarity	NPD6925	Approved
0.6136	Remote Similarity	NPD5776	Phase 2
0.6132	Remote Similarity	NPD6372	Approved
0.6132	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6373	Approved
0.6129	Remote Similarity	NPD6893	Approved
0.6129	Remote Similarity	NPD5329	Approved
0.6122	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7900	Approved
0.6087	Remote Similarity	NPD4788	Approved
0.6082	Remote Similarity	NPD5284	Approved
0.6082	Remote Similarity	NPD5281	Approved
0.6071	Remote Similarity	NPD6923	Approved
0.6071	Remote Similarity	NPD6922	Approved
0.6067	Remote Similarity	NPD4271	Approved
0.6067	Remote Similarity	NPD4268	Approved
0.6067	Remote Similarity	NPD3617	Approved
0.6064	Remote Similarity	NPD4688	Approved
0.6064	Remote Similarity	NPD4690	Approved
0.6064	Remote Similarity	NPD5205	Approved
0.6064	Remote Similarity	NPD4689	Approved
0.6064	Remote Similarity	NPD4694	Approved
0.6064	Remote Similarity	NPD4693	Phase 3
0.6064	Remote Similarity	NPD4138	Approved
0.6064	Remote Similarity	NPD5280	Approved
0.6061	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4732	Discontinued
0.6044	Remote Similarity	NPD6898	Phase 1
0.6036	Remote Similarity	NPD6009	Approved
0.6036	Remote Similarity	NPD6317	Approved
0.6022	Remote Similarity	NPD3668	Phase 3
0.602	Remote Similarity	NPD6399	Phase 3
0.6019	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD4191	Approved
0.5982	Remote Similarity	NPD6314	Approved
0.5982	Remote Similarity	NPD7328	Approved
0.5982	Remote Similarity	NPD6313	Approved
0.5982	Remote Similarity	NPD7327	Approved
0.5982	Remote Similarity	NPD6335	Approved
0.5978	Remote Similarity	NPD4269	Approved
0.5978	Remote Similarity	NPD4270	Approved
0.5977	Remote Similarity	NPD4784	Approved
0.5977	Remote Similarity	NPD4785	Approved
0.5976	Remote Similarity	NPD7341	Phase 2
0.5974	Remote Similarity	NPD4219	Approved
0.596	Remote Similarity	NPD5282	Discontinued
0.5957	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6274	Approved
0.5941	Remote Similarity	NPD6084	Phase 2
0.5941	Remote Similarity	NPD6083	Phase 2
0.5934	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.593	Remote Similarity	NPD4243	Approved
0.5929	Remote Similarity	NPD7516	Approved
0.5929	Remote Similarity	NPD7100	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