NPASS Compound

Structure

CID41577 OpenBabel06191715372D 31 35 0 0 1 0 0 0 0 0999 V2000 -4.3932 5.4195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9985 4.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8836 3.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6901 -2.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5626 -2.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6904 1.9823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 -1.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7903 3.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7437 3.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4889 2.6391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 -1.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3788 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5337 -0.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3785 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8453 1.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0451 4.6951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 2.4367 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5352 1.4621 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8453 -1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8448 -0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5340 -1.4627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -1.9507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6901 0.9745 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6899 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8451 -0.4876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4003 -1.9623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 19 29 1 0 0 0 0 19 30 1 0 0 0 0 21 3 1 1 0 0 0 21 22 1 0 0 0 0 22 27 1 6 0 0 0 23 26 1 0 0 0 0 23 29 1 6 0 0 0 24 28 1 1 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 31 1 6 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.4
Volume:	493.444
LogP:	8.404
LogD:	6.31
LogS:	-6.974
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	5.253
Fsp3:	1.0
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:	-5.057
MDCK Permeability:	1.430767497367924e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	95.94793701171875%
Volume Distribution (VD):	1.414
Pgp-substrate:	1.6352689266204834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.953
CYP2C9-inhibitor:	0.159
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.122
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.726
CYP3A4-substrate:	0.555

ADMET: Excretion

Clearance (CL):	8.676
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.738
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.948
Carcinogencity:	0.048
Eye Corrosion:	0.966
Eye Irritation:	0.497
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC41577

Natural Product ID:	NPC41577
*Common Name:**	Cycloartanol
IUPAC Name:	n.a.
Synonyms:	Cycloartanol
Standard InCHIKey:	YABASAWVVRQMEU-YBXTVTTCSA-N
Standard InCHI:	InChI=1S/C30H52O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h20-25,31H,8-19H2,1-7H3/t21-,22-,23+,24+,25+,27-,28+,29-,30+/m1/s1
SMILES:	CC(CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225763
PubChem CID:	12760132
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12932131]
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104489]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20460582]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25172746]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8910532]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16501	Capsicum annuum	Species	Solanaceae	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
MIC	1
Others	7

Activity Type	# Activity
Cell Line	2
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[541999]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	102.4	ug.mL-1	PMID[542000]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[541999]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	30.2	%	PMID[541999]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	70.2	%	PMID[541999]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	95.0	%	PMID[541999]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	9.4	nM	PMID[541999]
NPT2	Others	Unspecified		Activity	=	1.8	n.a.	PMID[541999]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	8.0	ug.mL-1	PMID[542000]
NPT2	Others	Unspecified		Ratio	=	12.8	n.a.	PMID[542000]

☑ 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 NPC41577 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	413
0.1-0.2	5540
0.2-0.3	18442
0.3-0.4	7405
0.4-0.5	4813
0.5-0.6	4002
0.6-0.7	1515
0.7-0.8	428
0.8-0.85	77
0.85-0.9	43
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473276
1.0	High Similarity	NPC474380
0.9833	High Similarity	NPC69149
0.9677	High Similarity	NPC473230
0.9677	High Similarity	NPC475884
0.95	High Similarity	NPC148174
0.95	High Similarity	NPC71460
0.95	High Similarity	NPC218585
0.9375	High Similarity	NPC299948
0.9375	High Similarity	NPC241085
0.9375	High Similarity	NPC470830
0.9344	High Similarity	NPC114891
0.9206	High Similarity	NPC142712
0.9091	High Similarity	NPC195530
0.9091	High Similarity	NPC473279
0.9062	High Similarity	NPC48079
0.8955	High Similarity	NPC473238
0.8955	High Similarity	NPC472341
0.8923	High Similarity	NPC472741
0.8906	High Similarity	NPC44122
0.8889	High Similarity	NPC159654
0.8889	High Similarity	NPC167995
0.8889	High Similarity	NPC281540
0.8889	High Similarity	NPC118937
0.8852	High Similarity	NPC95958
0.8824	High Similarity	NPC478130
0.8824	High Similarity	NPC254509
0.8824	High Similarity	NPC49168
0.8824	High Similarity	NPC196358
0.8824	High Similarity	NPC5046
0.8824	High Similarity	NPC145552
0.8788	High Similarity	NPC254037
0.8788	High Similarity	NPC66407
0.8788	High Similarity	NPC129829
0.8788	High Similarity	NPC477820
0.8788	High Similarity	NPC107919
0.8696	High Similarity	NPC230704
0.8696	High Similarity	NPC273366
0.8696	High Similarity	NPC200243
0.8696	High Similarity	NPC70982
0.8689	High Similarity	NPC476735
0.8676	High Similarity	NPC195489
0.8657	High Similarity	NPC282454
0.8657	High Similarity	NPC63588
0.8657	High Similarity	NPC231945
0.8657	High Similarity	NPC192192
0.8657	High Similarity	NPC232925
0.8657	High Similarity	NPC251201
0.8571	High Similarity	NPC95804
0.8571	High Similarity	NPC185547
0.8529	High Similarity	NPC252182
0.8529	High Similarity	NPC157422
0.8529	High Similarity	NPC1340
0.8529	High Similarity	NPC187471
0.8529	High Similarity	NPC127094
0.8529	High Similarity	NPC111234
0.8529	High Similarity	NPC100586
0.8529	High Similarity	NPC478103
0.8529	High Similarity	NPC109457
0.8529	High Similarity	NPC470071
0.8485	Intermediate Similarity	NPC63190
0.8451	Intermediate Similarity	NPC331618
0.8451	Intermediate Similarity	NPC475031
0.8451	Intermediate Similarity	NPC257191
0.8438	Intermediate Similarity	NPC292419
0.8438	Intermediate Similarity	NPC290791
0.8406	Intermediate Similarity	NPC232112
0.8406	Intermediate Similarity	NPC153719
0.8406	Intermediate Similarity	NPC470610
0.8382	Intermediate Similarity	NPC45296
0.8333	Intermediate Similarity	NPC65897
0.8333	Intermediate Similarity	NPC147993
0.8333	Intermediate Similarity	NPC85346
0.8333	Intermediate Similarity	NPC471769
0.8333	Intermediate Similarity	NPC472342
0.8333	Intermediate Similarity	NPC302041
0.831	Intermediate Similarity	NPC470145
0.8286	Intermediate Similarity	NPC228994
0.8286	Intermediate Similarity	NPC192501
0.8286	Intermediate Similarity	NPC477508
0.8286	Intermediate Similarity	NPC192638
0.8286	Intermediate Similarity	NPC25511
0.8286	Intermediate Similarity	NPC304499
0.8286	Intermediate Similarity	NPC62657
0.8286	Intermediate Similarity	NPC10476
0.8286	Intermediate Similarity	NPC48795
0.8261	Intermediate Similarity	NPC8004
0.8261	Intermediate Similarity	NPC131506
0.8261	Intermediate Similarity	NPC156277
0.8261	Intermediate Similarity	NPC320549
0.8261	Intermediate Similarity	NPC127283
0.8261	Intermediate Similarity	NPC151018
0.8261	Intermediate Similarity	NPC58057
0.8261	Intermediate Similarity	NPC157777
0.8226	Intermediate Similarity	NPC135438
0.8219	Intermediate Similarity	NPC287452
0.8194	Intermediate Similarity	NPC476233
0.8182	Intermediate Similarity	NPC260116
0.8182	Intermediate Similarity	NPC190827
0.8182	Intermediate Similarity	NPC80463
0.8182	Intermediate Similarity	NPC243469
0.8182	Intermediate Similarity	NPC475943
0.8169	Intermediate Similarity	NPC158208
0.8169	Intermediate Similarity	NPC91387
0.8169	Intermediate Similarity	NPC212879
0.8169	Intermediate Similarity	NPC174964
0.8169	Intermediate Similarity	NPC196136
0.8169	Intermediate Similarity	NPC185536
0.8169	Intermediate Similarity	NPC97534
0.8169	Intermediate Similarity	NPC231680
0.8169	Intermediate Similarity	NPC317242
0.8169	Intermediate Similarity	NPC240235
0.8169	Intermediate Similarity	NPC195155
0.8169	Intermediate Similarity	NPC243027
0.8169	Intermediate Similarity	NPC104387
0.8169	Intermediate Similarity	NPC178383
0.8169	Intermediate Similarity	NPC212733
0.8169	Intermediate Similarity	NPC231256
0.8169	Intermediate Similarity	NPC3403
0.8169	Intermediate Similarity	NPC270306
0.8154	Intermediate Similarity	NPC249078
0.8154	Intermediate Similarity	NPC236099
0.8154	Intermediate Similarity	NPC209686
0.8095	Intermediate Similarity	NPC162685
0.8088	Intermediate Similarity	NPC474756
0.8082	Intermediate Similarity	NPC312328
0.8056	Intermediate Similarity	NPC5767
0.8056	Intermediate Similarity	NPC14112
0.8056	Intermediate Similarity	NPC4209
0.8056	Intermediate Similarity	NPC93662
0.8056	Intermediate Similarity	NPC278091
0.8056	Intermediate Similarity	NPC477601
0.8056	Intermediate Similarity	NPC472486
0.8056	Intermediate Similarity	NPC163597
0.8056	Intermediate Similarity	NPC91573
0.8056	Intermediate Similarity	NPC472487
0.8056	Intermediate Similarity	NPC475742
0.8056	Intermediate Similarity	NPC477602
0.8056	Intermediate Similarity	NPC237460
0.8056	Intermediate Similarity	NPC473916
0.8056	Intermediate Similarity	NPC78067
0.8056	Intermediate Similarity	NPC86305
0.8028	Intermediate Similarity	NPC308440
0.8028	Intermediate Similarity	NPC472503
0.8028	Intermediate Similarity	NPC167702
0.8028	Intermediate Similarity	NPC254340
0.8028	Intermediate Similarity	NPC280026
0.8	Intermediate Similarity	NPC89310
0.8	Intermediate Similarity	NPC12933
0.8	Intermediate Similarity	NPC469745
0.7971	Intermediate Similarity	NPC327728
0.7971	Intermediate Similarity	NPC99264
0.7971	Intermediate Similarity	NPC131892
0.7971	Intermediate Similarity	NPC213178
0.7971	Intermediate Similarity	NPC6120
0.7945	Intermediate Similarity	NPC202540
0.7945	Intermediate Similarity	NPC207010
0.7945	Intermediate Similarity	NPC317913
0.7945	Intermediate Similarity	NPC474574
0.7945	Intermediate Similarity	NPC119355
0.7945	Intermediate Similarity	NPC477227
0.7945	Intermediate Similarity	NPC143133
0.7945	Intermediate Similarity	NPC11907
0.7945	Intermediate Similarity	NPC105208
0.7945	Intermediate Similarity	NPC298168
0.7945	Intermediate Similarity	NPC248830
0.7945	Intermediate Similarity	NPC185915
0.7945	Intermediate Similarity	NPC128951
0.7945	Intermediate Similarity	NPC221420
0.7945	Intermediate Similarity	NPC133596
0.7945	Intermediate Similarity	NPC64081
0.7945	Intermediate Similarity	NPC302578
0.7945	Intermediate Similarity	NPC23884
0.7945	Intermediate Similarity	NPC212241
0.7945	Intermediate Similarity	NPC192046
0.7941	Intermediate Similarity	NPC204233
0.7937	Intermediate Similarity	NPC236588
0.7917	Intermediate Similarity	NPC103822
0.7917	Intermediate Similarity	NPC186851
0.7917	Intermediate Similarity	NPC125767
0.7917	Intermediate Similarity	NPC21220
0.791	Intermediate Similarity	NPC477603
0.791	Intermediate Similarity	NPC472946
0.7895	Intermediate Similarity	NPC475388
0.7887	Intermediate Similarity	NPC201373
0.7867	Intermediate Similarity	NPC16449
0.7867	Intermediate Similarity	NPC477851
0.7838	Intermediate Similarity	NPC224802
0.7838	Intermediate Similarity	NPC244385
0.7838	Intermediate Similarity	NPC34046
0.7838	Intermediate Similarity	NPC67657
0.7838	Intermediate Similarity	NPC102708
0.7838	Intermediate Similarity	NPC285761
0.7838	Intermediate Similarity	NPC18857
0.7838	Intermediate Similarity	NPC324700
0.7838	Intermediate Similarity	NPC477819
0.7838	Intermediate Similarity	NPC138621
0.7838	Intermediate Similarity	NPC171426
0.7838	Intermediate Similarity	NPC167037
0.7838	Intermediate Similarity	NPC31828

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 NPC41577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	424
0.1-0.2	4719
0.2-0.3	2931
0.3-0.4	614
0.4-0.5	189
0.5-0.6	193
0.6-0.7	53
0.7-0.8	21
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8788	High Similarity	NPD4267	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD4787	Phase 1
0.8261	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD6117	Approved
0.8028	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD6116	Phase 1
0.7838	Intermediate Similarity	NPD6697	Approved
0.7838	Intermediate Similarity	NPD6118	Approved
0.7838	Intermediate Similarity	NPD6115	Approved
0.7838	Intermediate Similarity	NPD6114	Approved
0.7671	Intermediate Similarity	NPD3703	Phase 2
0.7632	Intermediate Similarity	NPD7525	Registered
0.7606	Intermediate Similarity	NPD4244	Approved
0.7606	Intermediate Similarity	NPD4245	Approved
0.7606	Intermediate Similarity	NPD4789	Approved
0.7571	Intermediate Similarity	NPD5360	Phase 3
0.7571	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD3698	Phase 2
0.7432	Intermediate Similarity	NPD6942	Approved
0.7432	Intermediate Similarity	NPD7339	Approved
0.7403	Intermediate Similarity	NPD6928	Phase 2
0.7391	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD385	Approved
0.7167	Intermediate Similarity	NPD384	Approved
0.716	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3671	Phase 1
0.7083	Intermediate Similarity	NPD6705	Phase 1
0.7027	Intermediate Similarity	NPD4758	Discontinued
0.6883	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7645	Phase 2
0.6806	Remote Similarity	NPD4224	Phase 2
0.68	Remote Similarity	NPD6081	Approved
0.675	Remote Similarity	NPD4748	Discontinued
0.6744	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6700	Approved
0.6709	Remote Similarity	NPD5364	Discontinued
0.6667	Remote Similarity	NPD6703	Approved
0.6667	Remote Similarity	NPD6702	Approved
0.6628	Remote Similarity	NPD5328	Approved
0.6627	Remote Similarity	NPD4786	Approved
0.6623	Remote Similarity	NPD6924	Approved
0.6623	Remote Similarity	NPD6926	Approved
0.6579	Remote Similarity	NPD7150	Approved
0.6579	Remote Similarity	NPD4243	Approved
0.6579	Remote Similarity	NPD7151	Approved
0.6579	Remote Similarity	NPD5777	Approved
0.6579	Remote Similarity	NPD7152	Approved
0.6538	Remote Similarity	NPD3702	Approved
0.6533	Remote Similarity	NPD6923	Approved
0.6533	Remote Similarity	NPD6922	Approved
0.6506	Remote Similarity	NPD4788	Approved
0.6477	Remote Similarity	NPD8034	Phase 2
0.6477	Remote Similarity	NPD8035	Phase 2
0.6477	Remote Similarity	NPD6079	Approved
0.6471	Remote Similarity	NPD3618	Phase 1
0.6456	Remote Similarity	NPD6933	Approved
0.6447	Remote Similarity	NPD7143	Approved
0.6447	Remote Similarity	NPD7144	Approved
0.641	Remote Similarity	NPD4784	Approved
0.641	Remote Similarity	NPD4785	Approved
0.6404	Remote Similarity	NPD8171	Discontinued
0.6386	Remote Similarity	NPD3667	Approved
0.6304	Remote Similarity	NPD7920	Phase 3
0.6304	Remote Similarity	NPD7919	Phase 3
0.6279	Remote Similarity	NPD8308	Discontinued
0.6237	Remote Similarity	NPD8088	Phase 1
0.6222	Remote Similarity	NPD4202	Approved
0.622	Remote Similarity	NPD6929	Approved
0.6207	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.617	Remote Similarity	NPD8418	Phase 2
0.6145	Remote Similarity	NPD6931	Approved
0.6145	Remote Similarity	NPD6930	Phase 2
0.6145	Remote Similarity	NPD7509	Discontinued
0.6125	Remote Similarity	NPD4190	Phase 3
0.6125	Remote Similarity	NPD5275	Approved
0.6087	Remote Similarity	NPD7991	Discontinued
0.6081	Remote Similarity	NPD371	Approved
0.6071	Remote Similarity	NPD6902	Approved
0.6064	Remote Similarity	NPD7638	Approved
0.6047	Remote Similarity	NPD3665	Phase 1
0.6047	Remote Similarity	NPD3133	Approved
0.6047	Remote Similarity	NPD3666	Approved
0.6022	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5222	Approved
0.6022	Remote Similarity	NPD5221	Approved
0.6022	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD7639	Approved
0.5976	Remote Similarity	NPD6925	Approved
0.5976	Remote Similarity	NPD6932	Approved
0.5976	Remote Similarity	NPD5776	Phase 2
0.5957	Remote Similarity	NPD5173	Approved
0.5957	Remote Similarity	NPD4755	Approved
0.5938	Remote Similarity	NPD386	Approved
0.5938	Remote Similarity	NPD388	Approved
0.5934	Remote Similarity	NPD7515	Phase 2
0.593	Remote Similarity	NPD6695	Phase 3
0.5904	Remote Similarity	NPD7145	Approved
0.5876	Remote Similarity	NPD7632	Discontinued
0.587	Remote Similarity	NPD6399	Phase 3
0.5862	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5285	Approved
0.5833	Remote Similarity	NPD4195	Approved
0.5833	Remote Similarity	NPD6683	Phase 2
0.5833	Remote Similarity	NPD4700	Approved
0.5833	Remote Similarity	NPD5286	Approved
0.5833	Remote Similarity	NPD4696	Approved
0.5795	Remote Similarity	NPD6893	Approved
0.5775	Remote Similarity	NPD586	Phase 1
0.5773	Remote Similarity	NPD5223	Approved
0.5773	Remote Similarity	NPD4159	Approved
0.5765	Remote Similarity	NPD7514	Phase 3
0.5758	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD3198	Approved
0.573	Remote Similarity	NPD5279	Phase 3
0.5729	Remote Similarity	NPD5290	Discontinued
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD5226	Approved
0.5714	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3617	Approved
0.57	Remote Similarity	NPD6920	Discontinued
0.57	Remote Similarity	NPD7128	Approved
0.57	Remote Similarity	NPD6402	Approved
0.57	Remote Similarity	NPD5739	Approved
0.57	Remote Similarity	NPD6675	Approved
0.5682	Remote Similarity	NPD3668	Phase 3
0.5667	Remote Similarity	NPD7750	Discontinued
0.5667	Remote Similarity	NPD7524	Approved
0.5657	Remote Similarity	NPD4754	Approved
0.5657	Remote Similarity	NPD5175	Approved
0.5657	Remote Similarity	NPD5174	Approved
0.5638	Remote Similarity	NPD7748	Approved
0.5632	Remote Similarity	NPD4221	Approved
0.5632	Remote Similarity	NPD4223	Phase 3
0.5618	Remote Similarity	NPD5329	Approved
0.561	Remote Similarity	NPD1811	Approved
0.561	Remote Similarity	NPD1810	Approved
0.56	Remote Similarity	NPD5141	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