NPASS Compound

Structure

CID273366 OpenBabel06191716082D 32 36 0 0 1 0 0 0 0 0999 V2000 4.3963 -5.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0028 -4.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8849 -3.1634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6913 2.9607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5645 2.4564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 -1.9838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 1.0090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4914 -2.6410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7930 -3.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3813 -0.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5356 0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3810 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6905 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 -1.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0488 -4.6985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5373 -2.4385 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5370 -1.4631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7471 -3.7710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 1.4642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5359 1.4637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6911 1.9521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6914 -0.9752 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6911 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8457 0.4879 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 5.3995 -3.0460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4021 1.9634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 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 20 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 22 1 0 0 0 0 20 3 1 1 0 0 0 20 21 1 0 0 0 0 21 27 1 6 0 0 0 22 31 2 0 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 32 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 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.38
Volume:	499.598
LogP:	6.563
LogD:	5.356
LogS:	-5.623
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	5.361
Fsp3:	0.967
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:	-5.101
MDCK Permeability:	1.3094826499582268e-05
Pgp-inhibitor:	0.153
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	95.60161590576172%
Volume Distribution (VD):	1.395
Pgp-substrate:	1.5363142490386963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.379
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.956
CYP2C9-inhibitor:	0.223
CYP2C9-substrate:	0.246
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.615
CYP3A4-inhibitor:	0.818
CYP3A4-substrate:	0.789

ADMET: Excretion

Clearance (CL):	8.714
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.276
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.112
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.809
Carcinogencity:	0.094
Eye Corrosion:	0.041
Eye Irritation:	0.047
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC273366

Natural Product ID:	NPC273366
*Common Name:**	IQGSJIIKMZFWSP-XLWCLXEDSA-N
IUPAC Name:	n.a.
Synonyms:	24-Oxocycloartanol
Standard InCHIKey:	IQGSJIIKMZFWSP-XLWCLXEDSA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-19(2)22(31)9-8-20(3)21-12-14-28(7)24-11-10-23-26(4,5)25(32)13-15-29(23)18-30(24,29)17-16-27(21,28)6/h19-21,23-25,32H,8-18H2,1-7H3/t20-,21-,23+,24+,25+,27-,28+,29-,30+/m1/s1
SMILES:	O=C(C(C)C)CC[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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225869
PubChem CID:	44423570
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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO33132	bryonia dioica	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11858752]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO33132	bryonia dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17503850]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	Asteraceae	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
ED50	1
IC50	1
Others	7

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	5
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[463841]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ratio	=	4.0	n.a.	PMID[463842]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[463841]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	19.8	%	PMID[463841]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	62.7	%	PMID[463841]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	90.5	%	PMID[463841]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	8.1	nM	PMID[463841]
NPT2	Others	Unspecified		Activity	=	2.0	n.a.	PMID[463841]
NPT2	Others	Unspecified		ED50	=	4.0	ug ml-1	PMID[463843]

☑ 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 NPC273366 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	326
0.1-0.2	3381
0.2-0.3	15072
0.3-0.4	9917
0.4-0.5	5463
0.5-0.6	5053
0.6-0.7	2567
0.7-0.8	740
0.8-0.85	108
0.85-0.9	48
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC475031
0.971	High Similarity	NPC232112
0.9565	High Similarity	NPC320549
0.9565	High Similarity	NPC156277
0.9565	High Similarity	NPC58057
0.9565	High Similarity	NPC151018
0.9437	High Similarity	NPC97534
0.9437	High Similarity	NPC174964
0.9437	High Similarity	NPC195155
0.9306	High Similarity	NPC472486
0.9306	High Similarity	NPC472487
0.9306	High Similarity	NPC475742
0.9306	High Similarity	NPC5767
0.9296	High Similarity	NPC254340
0.9286	High Similarity	NPC89310
0.9275	High Similarity	NPC327728
0.9275	High Similarity	NPC6120
0.9275	High Similarity	NPC131892
0.9275	High Similarity	NPC213178
0.92	High Similarity	NPC469745
0.9178	High Similarity	NPC23884
0.9178	High Similarity	NPC221420
0.9167	High Similarity	NPC21220
0.9167	High Similarity	NPC125767
0.9167	High Similarity	NPC212733
0.9041	High Similarity	NPC4209
0.9028	High Similarity	NPC280026
0.9028	High Similarity	NPC167702
0.9014	High Similarity	NPC473267
0.8947	High Similarity	NPC12933
0.8933	High Similarity	NPC320144
0.8919	High Similarity	NPC143133
0.8919	High Similarity	NPC264602
0.8919	High Similarity	NPC317913
0.8919	High Similarity	NPC207010
0.8919	High Similarity	NPC298168
0.8904	High Similarity	NPC159789
0.8889	High Similarity	NPC310766
0.8846	High Similarity	NPC474996
0.8816	High Similarity	NPC477851
0.88	High Similarity	NPC34046
0.88	High Similarity	NPC185465
0.88	High Similarity	NPC224802
0.88	High Similarity	NPC80089
0.88	High Similarity	NPC171426
0.88	High Similarity	NPC324700
0.8767	High Similarity	NPC133922
0.8734	High Similarity	NPC76518
0.8732	High Similarity	NPC324607
0.8732	High Similarity	NPC321732
0.8714	High Similarity	NPC475884
0.8714	High Similarity	NPC473230
0.8696	High Similarity	NPC474380
0.8696	High Similarity	NPC473276
0.8696	High Similarity	NPC41577
0.8684	High Similarity	NPC201276
0.8684	High Similarity	NPC80891
0.863	High Similarity	NPC477229
0.863	High Similarity	NPC282905
0.863	High Similarity	NPC68426
0.8611	High Similarity	NPC477850
0.8608	High Similarity	NPC319909
0.8592	High Similarity	NPC474954
0.859	High Similarity	NPC61107
0.859	High Similarity	NPC289486
0.859	High Similarity	NPC30583
0.8571	High Similarity	NPC470609
0.8553	High Similarity	NPC478128
0.8551	High Similarity	NPC69149
0.8519	High Similarity	NPC202937
0.8514	High Similarity	NPC159325
0.8514	High Similarity	NPC472854
0.8514	High Similarity	NPC168511
0.8481	Intermediate Similarity	NPC475726
0.8481	Intermediate Similarity	NPC472743
0.8481	Intermediate Similarity	NPC327451
0.8472	Intermediate Similarity	NPC474962
0.8472	Intermediate Similarity	NPC470830
0.8472	Intermediate Similarity	NPC319671
0.8472	Intermediate Similarity	NPC299948
0.8472	Intermediate Similarity	NPC469941
0.8472	Intermediate Similarity	NPC252032
0.8472	Intermediate Similarity	NPC476734
0.8472	Intermediate Similarity	NPC241085
0.8462	Intermediate Similarity	NPC58631
0.8451	Intermediate Similarity	NPC472984
0.8442	Intermediate Similarity	NPC52951
0.8406	Intermediate Similarity	NPC114891
0.84	Intermediate Similarity	NPC267753
0.8395	Intermediate Similarity	NPC302111
0.8378	Intermediate Similarity	NPC81759
0.8378	Intermediate Similarity	NPC474123
0.8375	Intermediate Similarity	NPC474482
0.8375	Intermediate Similarity	NPC475745
0.8375	Intermediate Similarity	NPC50438
0.8375	Intermediate Similarity	NPC473336
0.8375	Intermediate Similarity	NPC471044
0.8356	Intermediate Similarity	NPC476731
0.8356	Intermediate Similarity	NPC477929
0.8354	Intermediate Similarity	NPC268040
0.8354	Intermediate Similarity	NPC477858
0.8354	Intermediate Similarity	NPC121121
0.8354	Intermediate Similarity	NPC317066
0.8354	Intermediate Similarity	NPC328007
0.8333	Intermediate Similarity	NPC261616
0.8333	Intermediate Similarity	NPC473225
0.8313	Intermediate Similarity	NPC122116
0.8312	Intermediate Similarity	NPC329117
0.831	Intermediate Similarity	NPC142712
0.8289	Intermediate Similarity	NPC108840
0.8272	Intermediate Similarity	NPC292553
0.8267	Intermediate Similarity	NPC130011
0.8261	Intermediate Similarity	NPC148174
0.8261	Intermediate Similarity	NPC218585
0.8261	Intermediate Similarity	NPC71460
0.825	Intermediate Similarity	NPC472744
0.8243	Intermediate Similarity	NPC195530
0.8243	Intermediate Similarity	NPC473279
0.8243	Intermediate Similarity	NPC126642
0.8228	Intermediate Similarity	NPC77311
0.8219	Intermediate Similarity	NPC196197
0.8214	Intermediate Similarity	NPC475056
0.8194	Intermediate Similarity	NPC474221
0.8194	Intermediate Similarity	NPC130459
0.8194	Intermediate Similarity	NPC48079
0.8194	Intermediate Similarity	NPC478180
0.8193	Intermediate Similarity	NPC146937
0.8182	Intermediate Similarity	NPC472746
0.8171	Intermediate Similarity	NPC80700
0.8171	Intermediate Similarity	NPC472738
0.8171	Intermediate Similarity	NPC476726
0.8171	Intermediate Similarity	NPC476727
0.8158	Intermediate Similarity	NPC24014
0.8158	Intermediate Similarity	NPC27349
0.8158	Intermediate Similarity	NPC472311
0.8148	Intermediate Similarity	NPC474233
0.8148	Intermediate Similarity	NPC74595
0.8148	Intermediate Similarity	NPC264665
0.8133	Intermediate Similarity	NPC473238
0.8133	Intermediate Similarity	NPC472341
0.8118	Intermediate Similarity	NPC52756
0.8108	Intermediate Similarity	NPC108131
0.8101	Intermediate Similarity	NPC164999
0.8095	Intermediate Similarity	NPC24705
0.8095	Intermediate Similarity	NPC56962
0.8082	Intermediate Similarity	NPC2568
0.8082	Intermediate Similarity	NPC472741
0.8082	Intermediate Similarity	NPC180777
0.8082	Intermediate Similarity	NPC103647
0.8082	Intermediate Similarity	NPC260319
0.8072	Intermediate Similarity	NPC263802
0.8072	Intermediate Similarity	NPC4643
0.8072	Intermediate Similarity	NPC57469
0.8056	Intermediate Similarity	NPC44122
0.8056	Intermediate Similarity	NPC42060
0.8049	Intermediate Similarity	NPC294438
0.8049	Intermediate Similarity	NPC264317
0.8028	Intermediate Similarity	NPC281540
0.8028	Intermediate Similarity	NPC118937
0.8028	Intermediate Similarity	NPC167995
0.8028	Intermediate Similarity	NPC159654
0.8026	Intermediate Similarity	NPC477930
0.8026	Intermediate Similarity	NPC478130
0.8025	Intermediate Similarity	NPC291320
0.8025	Intermediate Similarity	NPC163616
0.8025	Intermediate Similarity	NPC471036
0.8023	Intermediate Similarity	NPC12722
0.8	Intermediate Similarity	NPC469940
0.8	Intermediate Similarity	NPC50658
0.8	Intermediate Similarity	NPC77756
0.7976	Intermediate Similarity	NPC193360
0.7976	Intermediate Similarity	NPC472739
0.7976	Intermediate Similarity	NPC474719
0.7975	Intermediate Similarity	NPC245029
0.7975	Intermediate Similarity	NPC201459
0.7975	Intermediate Similarity	NPC31302
0.7973	Intermediate Similarity	NPC107919
0.7973	Intermediate Similarity	NPC254037
0.7973	Intermediate Similarity	NPC66407
0.7973	Intermediate Similarity	NPC477820
0.7973	Intermediate Similarity	NPC129829
0.7973	Intermediate Similarity	NPC64466
0.7952	Intermediate Similarity	NPC472745
0.7952	Intermediate Similarity	NPC269396
0.7952	Intermediate Similarity	NPC98236
0.7952	Intermediate Similarity	NPC70661
0.7952	Intermediate Similarity	NPC472272
0.7952	Intermediate Similarity	NPC474448
0.7952	Intermediate Similarity	NPC2783
0.7952	Intermediate Similarity	NPC12774
0.7949	Intermediate Similarity	NPC477918
0.7949	Intermediate Similarity	NPC477919
0.7949	Intermediate Similarity	NPC474404
0.7949	Intermediate Similarity	NPC180199
0.7927	Intermediate Similarity	NPC146683
0.7922	Intermediate Similarity	NPC230704
0.7922	Intermediate Similarity	NPC70982
0.7922	Intermediate Similarity	NPC72444
0.7922	Intermediate Similarity	NPC179858
0.7901	Intermediate Similarity	NPC145143

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 NPC273366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	3658
0.2-0.3	3634
0.3-0.4	906
0.4-0.5	213
0.5-0.6	199
0.6-0.7	131
0.7-0.8	16
0.8-0.85	4
0.85-0.9	14
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9565	High Similarity	NPD4809	Clinical (unspecified phase)
0.9565	High Similarity	NPD4808	Clinical (unspecified phase)
0.9275	High Similarity	NPD3700	Clinical (unspecified phase)
0.9275	High Similarity	NPD3699	Clinical (unspecified phase)
0.9041	High Similarity	NPD6117	Approved
0.9028	High Similarity	NPD6113	Clinical (unspecified phase)
0.8919	High Similarity	NPD6116	Phase 1
0.8904	High Similarity	NPD3703	Phase 2
0.8873	High Similarity	NPD4244	Approved
0.8873	High Similarity	NPD4245	Approved
0.8873	High Similarity	NPD4789	Approved
0.8857	High Similarity	NPD5360	Phase 3
0.8857	High Similarity	NPD5361	Clinical (unspecified phase)
0.88	High Similarity	NPD6118	Approved
0.88	High Similarity	NPD6115	Approved
0.88	High Similarity	NPD6114	Approved
0.88	High Similarity	NPD6697	Approved
0.8732	High Similarity	NPD3698	Phase 2
0.8696	High Similarity	NPD3171	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD3671	Phase 1
0.8243	Intermediate Similarity	NPD4758	Discontinued
0.8056	Intermediate Similarity	NPD4224	Phase 2
0.8049	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6081	Approved
0.7973	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5364	Discontinued
0.7763	Intermediate Similarity	NPD5777	Approved
0.7711	Intermediate Similarity	NPD4786	Approved
0.7674	Intermediate Similarity	NPD5328	Approved
0.7632	Intermediate Similarity	NPD4787	Phase 1
0.759	Intermediate Similarity	NPD4788	Approved
0.7529	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD6079	Approved
0.747	Intermediate Similarity	NPD3667	Approved
0.7468	Intermediate Similarity	NPD3702	Approved
0.7303	Intermediate Similarity	NPD8034	Phase 2
0.7303	Intermediate Similarity	NPD8035	Phase 2
0.7222	Intermediate Similarity	NPD4202	Approved
0.7093	Intermediate Similarity	NPD3133	Approved
0.7093	Intermediate Similarity	NPD3666	Approved
0.7093	Intermediate Similarity	NPD3665	Phase 1
0.7024	Intermediate Similarity	NPD7525	Registered
0.6989	Remote Similarity	NPD5221	Approved
0.6989	Remote Similarity	NPD5222	Approved
0.6989	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD8418	Phase 2
0.6923	Remote Similarity	NPD7515	Phase 2
0.6915	Remote Similarity	NPD5173	Approved
0.6915	Remote Similarity	NPD4755	Approved
0.6848	Remote Similarity	NPD6399	Phase 3
0.6824	Remote Similarity	NPD6928	Phase 2
0.6786	Remote Similarity	NPD3617	Approved
0.6771	Remote Similarity	NPD4700	Approved
0.6771	Remote Similarity	NPD4696	Approved
0.6771	Remote Similarity	NPD5286	Approved
0.6771	Remote Similarity	NPD5285	Approved
0.6757	Remote Similarity	NPD3198	Approved
0.6742	Remote Similarity	NPD5279	Phase 3
0.6705	Remote Similarity	NPD3668	Phase 3
0.6703	Remote Similarity	NPD4753	Phase 2
0.6701	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5226	Approved
0.6633	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD4633	Approved
0.6633	Remote Similarity	NPD5211	Phase 2
0.6633	Remote Similarity	NPD5224	Approved
0.6629	Remote Similarity	NPD5329	Approved
0.6627	Remote Similarity	NPD6942	Approved
0.6627	Remote Similarity	NPD7339	Approved
0.66	Remote Similarity	NPD5739	Approved
0.66	Remote Similarity	NPD6920	Discontinued
0.66	Remote Similarity	NPD6402	Approved
0.66	Remote Similarity	NPD7128	Approved
0.66	Remote Similarity	NPD6675	Approved
0.6596	Remote Similarity	NPD7748	Approved
0.6566	Remote Similarity	NPD5175	Approved
0.6566	Remote Similarity	NPD5174	Approved
0.6566	Remote Similarity	NPD4754	Approved
0.6556	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4692	Approved
0.6552	Remote Similarity	NPD4139	Approved
0.6517	Remote Similarity	NPD4197	Approved
0.65	Remote Similarity	NPD6705	Phase 1
0.65	Remote Similarity	NPD5141	Approved
0.6495	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6471	Remote Similarity	NPD6415	Discontinued
0.6436	Remote Similarity	NPD4768	Approved
0.6436	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD7640	Approved
0.6429	Remote Similarity	NPD7639	Approved
0.6413	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6373	Approved
0.6408	Remote Similarity	NPD6372	Approved
0.6392	Remote Similarity	NPD7902	Approved
0.6392	Remote Similarity	NPD6084	Phase 2
0.6392	Remote Similarity	NPD6083	Phase 2
0.6374	Remote Similarity	NPD7146	Approved
0.6374	Remote Similarity	NPD5205	Approved
0.6374	Remote Similarity	NPD4690	Approved
0.6374	Remote Similarity	NPD7521	Approved
0.6374	Remote Similarity	NPD6684	Approved
0.6374	Remote Similarity	NPD5330	Approved
0.6374	Remote Similarity	NPD4688	Approved
0.6374	Remote Similarity	NPD4693	Phase 3
0.6374	Remote Similarity	NPD4138	Approved
0.6374	Remote Similarity	NPD7334	Approved
0.6374	Remote Similarity	NPD6409	Approved
0.6374	Remote Similarity	NPD4689	Approved
0.6373	Remote Similarity	NPD5697	Approved
0.6373	Remote Similarity	NPD5701	Approved
0.6354	Remote Similarity	NPD5210	Approved
0.6354	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4629	Approved
0.6353	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7290	Approved
0.6346	Remote Similarity	NPD7102	Approved
0.6346	Remote Similarity	NPD6883	Approved
0.6322	Remote Similarity	NPD7645	Phase 2
0.6311	Remote Similarity	NPD4729	Approved
0.6311	Remote Similarity	NPD5168	Approved
0.6311	Remote Similarity	NPD5128	Approved
0.6311	Remote Similarity	NPD4730	Approved
0.6311	Remote Similarity	NPD6011	Approved
0.6301	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7632	Discontinued
0.6286	Remote Similarity	NPD6649	Approved
0.6286	Remote Similarity	NPD6847	Approved
0.6286	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6650	Approved
0.6286	Remote Similarity	NPD6617	Approved
0.6286	Remote Similarity	NPD8130	Phase 1
0.6277	Remote Similarity	NPD6700	Approved
0.6277	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD4748	Discontinued
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6237	Remote Similarity	NPD6903	Approved
0.6237	Remote Similarity	NPD6672	Approved
0.6237	Remote Similarity	NPD5737	Approved
0.6232	Remote Similarity	NPD384	Approved
0.6232	Remote Similarity	NPD385	Approved
0.6226	Remote Similarity	NPD8297	Approved
0.6226	Remote Similarity	NPD6882	Approved
0.6211	Remote Similarity	NPD6703	Approved
0.6211	Remote Similarity	NPD6702	Approved
0.6196	Remote Similarity	NPD5690	Phase 2
0.6196	Remote Similarity	NPD4694	Approved
0.6196	Remote Similarity	NPD5280	Approved
0.619	Remote Similarity	NPD5169	Approved
0.619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5135	Approved
0.619	Remote Similarity	NPD5248	Approved
0.619	Remote Similarity	NPD4634	Approved
0.619	Remote Similarity	NPD5247	Approved
0.619	Remote Similarity	NPD5249	Phase 3
0.619	Remote Similarity	NPD5250	Approved
0.6168	Remote Similarity	NPD8298	Phase 2
0.6147	Remote Similarity	NPD7115	Discovery
0.6146	Remote Similarity	NPD5133	Approved
0.6132	Remote Similarity	NPD5127	Approved
0.6132	Remote Similarity	NPD5216	Approved
0.6132	Remote Similarity	NPD5217	Approved
0.6132	Remote Similarity	NPD5215	Approved
0.6118	Remote Similarity	NPD6926	Approved
0.6118	Remote Similarity	NPD6924	Approved
0.6082	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6001	Approved
0.6082	Remote Similarity	NPD7900	Approved
0.6081	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6868	Approved
0.6023	Remote Similarity	NPD4776	Phase 2
0.6023	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4777	Suspended
0.6022	Remote Similarity	NPD6098	Approved
0.602	Remote Similarity	NPD5695	Phase 3
0.6019	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5696	Approved
0.5979	Remote Similarity	NPD8171	Discontinued
0.5977	Remote Similarity	NPD6933	Approved
0.5965	Remote Similarity	NPD7604	Phase 2
0.5963	Remote Similarity	NPD5167	Approved
0.5962	Remote Similarity	NPD6008	Approved
0.5955	Remote Similarity	NPD4195	Approved
0.5952	Remote Similarity	NPD4747	Approved
0.5946	Remote Similarity	NPD6335	Approved
0.5909	Remote Similarity	NPD6940	Discontinued
0.5909	Remote Similarity	NPD6274	Approved
0.5905	Remote Similarity	NPD6412	Phase 2
0.59	Remote Similarity	NPD7920	Phase 3
0.59	Remote Similarity	NPD7919	Phase 3

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