NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	172.15
Volume:	190.54
LogP:	0.884
LogD:	1.058
LogS:	-0.549
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	2.851
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.288
MDCK Permeability:	1.907146543089766e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.906
Plasma Protein Binding (PPB):	53.64824676513672%
Volume Distribution (VD):	0.833
Pgp-substrate:	55.812686920166016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.317
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.314
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	9.369
Half-life (T1/2):	0.564

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.212
Carcinogencity:	0.291
Eye Corrosion:	0.924
Eye Irritation:	0.983
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC77550

Natural Product ID:	NPC77550
*Common Name:**	Terpin
IUPAC Name:	4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol
Synonyms:	Terpin
Standard InCHIKey:	RBNWAMSGVWEHFP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H20O2/c1-9(2,11)8-4-6-10(3,12)7-5-8/h8,11-12H,4-7H2,1-3H3
SMILES:	CC(C)(C1CCC(C)(CC1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651998
PubChem CID:	6651
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001401] Menthane monoterpenoids

*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
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190854]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	stems and twigs	Beihai, Guangxi province, China	2008-Jan	PMID[22196120]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23387901]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7591	Cedrus deodara	Species	Pinaceae	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
GI50	58
Others	8
Potency	1

Activity Type	# Activity
Cell Line	58
Organism	7
Others	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	504.66	nM	PMID[510072]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	16069.41	nM	PMID[510072]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[510072]
NPT2	Others	Unspecified		Potency	n.a.	4730.8	nM	PubChem BioAssay data set
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	118.7	%	PMID[510071]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	124.7	%	PMID[510071]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	23.8	%	PMID[510071]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	77.9	%	PMID[510071]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-2.43	%	PMID[510073]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	12.71	%	PMID[510074]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.19	%	PMID[510075]

☑ 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 NPC77550 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	353
0.1-0.2	5768
0.2-0.3	20031
0.3-0.4	10231
0.4-0.5	5300
0.5-0.6	899
0.6-0.7	93
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC108441
0.82	Intermediate Similarity	NPC102336
0.82	Intermediate Similarity	NPC36002
0.7857	Intermediate Similarity	NPC328441
0.7826	Intermediate Similarity	NPC144891
0.7755	Intermediate Similarity	NPC316035
0.7708	Intermediate Similarity	NPC223468
0.7708	Intermediate Similarity	NPC176309
0.7708	Intermediate Similarity	NPC147343
0.7708	Intermediate Similarity	NPC287550
0.7708	Intermediate Similarity	NPC84030
0.7708	Intermediate Similarity	NPC198540
0.7447	Intermediate Similarity	NPC302939
0.7447	Intermediate Similarity	NPC287331
0.74	Intermediate Similarity	NPC294858
0.7358	Intermediate Similarity	NPC202146
0.7358	Intermediate Similarity	NPC32222
0.7347	Intermediate Similarity	NPC14552
0.7292	Intermediate Similarity	NPC313795
0.7273	Intermediate Similarity	NPC135438
0.7273	Intermediate Similarity	NPC236588
0.7222	Intermediate Similarity	NPC471269
0.72	Intermediate Similarity	NPC100445
0.7143	Intermediate Similarity	NPC47663
0.7119	Intermediate Similarity	NPC94897
0.7091	Intermediate Similarity	NPC170780
0.7037	Intermediate Similarity	NPC53209
0.7018	Intermediate Similarity	NPC185116
0.6949	Remote Similarity	NPC209686
0.6949	Remote Similarity	NPC236099
0.6949	Remote Similarity	NPC249078
0.6939	Remote Similarity	NPC240994
0.6909	Remote Similarity	NPC45387
0.6889	Remote Similarity	NPC177022
0.6875	Remote Similarity	NPC82843
0.6842	Remote Similarity	NPC215671
0.6842	Remote Similarity	NPC87296
0.6842	Remote Similarity	NPC475515
0.6809	Remote Similarity	NPC160261
0.6809	Remote Similarity	NPC469759
0.6792	Remote Similarity	NPC307022
0.6786	Remote Similarity	NPC3025
0.6786	Remote Similarity	NPC39068
0.6786	Remote Similarity	NPC179024
0.6786	Remote Similarity	NPC264779
0.678	Remote Similarity	NPC95804
0.678	Remote Similarity	NPC185547
0.6774	Remote Similarity	NPC88454
0.6774	Remote Similarity	NPC253303
0.6774	Remote Similarity	NPC117607
0.6774	Remote Similarity	NPC101307
0.6774	Remote Similarity	NPC269077
0.6731	Remote Similarity	NPC127997
0.6731	Remote Similarity	NPC95969
0.6724	Remote Similarity	NPC95958
0.6667	Remote Similarity	NPC245795
0.6667	Remote Similarity	NPC119425
0.6667	Remote Similarity	NPC474756
0.661	Remote Similarity	NPC475412
0.6596	Remote Similarity	NPC221022
0.6562	Remote Similarity	NPC254037
0.6562	Remote Similarity	NPC470833
0.6562	Remote Similarity	NPC66407
0.6562	Remote Similarity	NPC129829
0.6552	Remote Similarity	NPC474769
0.6552	Remote Similarity	NPC162685
0.6552	Remote Similarity	NPC189290
0.6545	Remote Similarity	NPC161473
0.6538	Remote Similarity	NPC314087
0.65	Remote Similarity	NPC282694
0.65	Remote Similarity	NPC194208
0.65	Remote Similarity	NPC79576
0.6481	Remote Similarity	NPC274261
0.6481	Remote Similarity	NPC291724
0.6462	Remote Similarity	NPC192192
0.6452	Remote Similarity	NPC19311
0.6452	Remote Similarity	NPC230047
0.6452	Remote Similarity	NPC471200
0.6452	Remote Similarity	NPC80463
0.6452	Remote Similarity	NPC260116
0.6441	Remote Similarity	NPC310228
0.6441	Remote Similarity	NPC475968
0.6441	Remote Similarity	NPC52431
0.6406	Remote Similarity	NPC469987
0.6406	Remote Similarity	NPC266578
0.6393	Remote Similarity	NPC114891
0.6364	Remote Similarity	NPC476149
0.6364	Remote Similarity	NPC252182
0.6364	Remote Similarity	NPC179169
0.6364	Remote Similarity	NPC187471
0.6364	Remote Similarity	NPC157781
0.6364	Remote Similarity	NPC244869
0.6364	Remote Similarity	NPC35519
0.6364	Remote Similarity	NPC306195
0.6364	Remote Similarity	NPC311102
0.6364	Remote Similarity	NPC300235
0.6364	Remote Similarity	NPC476136
0.6364	Remote Similarity	NPC470071
0.6364	Remote Similarity	NPC1340
0.6364	Remote Similarity	NPC127094
0.6364	Remote Similarity	NPC181255
0.6333	Remote Similarity	NPC240506
0.6316	Remote Similarity	NPC84824
0.6316	Remote Similarity	NPC300189
0.6316	Remote Similarity	NPC67508
0.6308	Remote Similarity	NPC234511
0.6308	Remote Similarity	NPC477820
0.6296	Remote Similarity	NPC131623
0.629	Remote Similarity	NPC128608
0.629	Remote Similarity	NPC118937
0.629	Remote Similarity	NPC159654
0.629	Remote Similarity	NPC101128
0.629	Remote Similarity	NPC281540
0.629	Remote Similarity	NPC167995
0.6271	Remote Similarity	NPC476735
0.6269	Remote Similarity	NPC95165
0.6269	Remote Similarity	NPC153719
0.625	Remote Similarity	NPC41542
0.625	Remote Similarity	NPC476928
0.625	Remote Similarity	NPC185874
0.625	Remote Similarity	NPC139207
0.625	Remote Similarity	NPC48079
0.625	Remote Similarity	NPC192962
0.623	Remote Similarity	NPC71460
0.623	Remote Similarity	NPC63111
0.623	Remote Similarity	NPC148174
0.623	Remote Similarity	NPC218585
0.623	Remote Similarity	NPC475807
0.623	Remote Similarity	NPC172622
0.6222	Remote Similarity	NPC283682
0.6212	Remote Similarity	NPC283316
0.6212	Remote Similarity	NPC63588
0.6212	Remote Similarity	NPC251201
0.6212	Remote Similarity	NPC232925
0.6207	Remote Similarity	NPC24443
0.619	Remote Similarity	NPC243469
0.619	Remote Similarity	NPC64123
0.619	Remote Similarity	NPC190827
0.619	Remote Similarity	NPC475943
0.619	Remote Similarity	NPC300442
0.619	Remote Similarity	NPC472946
0.619	Remote Similarity	NPC258595
0.6182	Remote Similarity	NPC26906
0.6182	Remote Similarity	NPC214584
0.6176	Remote Similarity	NPC470151
0.6176	Remote Similarity	NPC166250
0.6176	Remote Similarity	NPC192501
0.6176	Remote Similarity	NPC228994
0.6176	Remote Similarity	NPC475458
0.6176	Remote Similarity	NPC304499
0.6176	Remote Similarity	NPC10476
0.6154	Remote Similarity	NPC473914
0.6154	Remote Similarity	NPC2648
0.6154	Remote Similarity	NPC472741
0.6154	Remote Similarity	NPC276616
0.6154	Remote Similarity	NPC244790
0.6154	Remote Similarity	NPC314679
0.6154	Remote Similarity	NPC475893
0.6129	Remote Similarity	NPC50435
0.6129	Remote Similarity	NPC292419
0.6129	Remote Similarity	NPC174956
0.6129	Remote Similarity	NPC290791
0.6111	Remote Similarity	NPC224987
0.6102	Remote Similarity	NPC291147
0.6094	Remote Similarity	NPC142712
0.6094	Remote Similarity	NPC44122
0.6094	Remote Similarity	NPC103734
0.6087	Remote Similarity	NPC472952
0.6087	Remote Similarity	NPC472950
0.6087	Remote Similarity	NPC158208
0.6087	Remote Similarity	NPC91387
0.6087	Remote Similarity	NPC186851
0.6087	Remote Similarity	NPC231680
0.6087	Remote Similarity	NPC270306
0.6087	Remote Similarity	NPC317242
0.6087	Remote Similarity	NPC243027
0.6087	Remote Similarity	NPC196136
0.6078	Remote Similarity	NPC15162
0.6071	Remote Similarity	NPC71506
0.6071	Remote Similarity	NPC177112
0.6066	Remote Similarity	NPC66020
0.6061	Remote Similarity	NPC210323
0.6061	Remote Similarity	NPC107919
0.6061	Remote Similarity	NPC299948
0.6061	Remote Similarity	NPC470830
0.6061	Remote Similarity	NPC241085
0.6034	Remote Similarity	NPC283655
0.6034	Remote Similarity	NPC178223
0.6034	Remote Similarity	NPC166894
0.6034	Remote Similarity	NPC89069
0.6034	Remote Similarity	NPC277917
0.6032	Remote Similarity	NPC199937
0.6032	Remote Similarity	NPC69149
0.6032	Remote Similarity	NPC68656
0.6032	Remote Similarity	NPC476702
0.6032	Remote Similarity	NPC219940
0.6032	Remote Similarity	NPC144650
0.6029	Remote Similarity	NPC470610
0.6	Remote Similarity	NPC204233
0.6	Remote Similarity	NPC82337

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 NPC77550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	474
0.1-0.2	4874
0.2-0.3	2764
0.3-0.4	753
0.4-0.5	226
0.5-0.6	52
0.6-0.7	3
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD388	Approved
1.0	High Similarity	NPD386	Approved
0.7708	Intermediate Similarity	NPD385	Approved
0.7708	Intermediate Similarity	NPD384	Approved
0.7447	Intermediate Similarity	NPD367	Approved
0.7119	Intermediate Similarity	NPD371	Approved
0.6727	Remote Similarity	NPD615	Clinical (unspecified phase)
0.62	Remote Similarity	NPD1462	Approved
0.6154	Remote Similarity	NPD5360	Phase 3
0.6154	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD634	Phase 3
0.6122	Remote Similarity	NPD1460	Approved
0.6061	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.597	Remote Similarity	NPD4787	Phase 1
0.5942	Remote Similarity	NPD1811	Approved
0.5942	Remote Similarity	NPD1810	Approved
0.5938	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4758	Discontinued
0.5857	Remote Similarity	NPD3703	Phase 2
0.5846	Remote Similarity	NPD4224	Phase 2
0.5821	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD1145	Discontinued
0.5686	Remote Similarity	NPD9426	Discontinued
0.5652	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD6697	Approved
0.5616	Remote Similarity	NPD6114	Approved
0.5616	Remote Similarity	NPD6115	Approved
0.5616	Remote Similarity	NPD6118	Approved
0.56	Remote Similarity	NPD9450	Approved
0.56	Remote Similarity	NPD77	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