NPASS Compound

Structure

CID164295 OpenBabel06191715532D 23 25 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 18 2 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 14 18 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 6 0 0 0 21 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.22
Volume:	353.137
LogP:	5.976
LogD:	4.68
LogS:	-6.62
# Rotatable Bonds:	2
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	3.431
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.03
MDCK Permeability:	1.4457249562838115e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	96.5604476928711%
Volume Distribution (VD):	0.822
Pgp-substrate:	4.504946231842041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.286
CYP1A2-substrate:	0.904
CYP2C19-inhibitor:	0.618
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.487
CYP2C9-substrate:	0.796
CYP2D6-inhibitor:	0.369
CYP2D6-substrate:	0.677
CYP3A4-inhibitor:	0.68
CYP3A4-substrate:	0.608

ADMET: Excretion

Clearance (CL):	7.415
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.78
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.673
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.128
Carcinogencity:	0.327
Eye Corrosion:	0.013
Eye Irritation:	0.672
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC164295

Natural Product ID:	NPC164295
*Common Name:**	O-Methyl Sugiyl Ether
IUPAC Name:	(4aS,10aS)-6-methoxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
Synonyms:	O-Methyl Sugiyl Ether
Standard InCHIKey:	DMYISGJMGRTXJW-PZJWPPBQSA-N
Standard InCHI:	InChI=1S/C21H30O2/c1-13(2)14-10-15-16(11-18(14)23-6)21(5)9-7-8-20(3,4)19(21)12-17(15)22/h10-11,13,19H,7-9,12H2,1-6H3/t19-,21+/m0/s1
SMILES:	CC(C)c1cc2c(cc1OC)[C@@]1(C)CCCC(C)(C)[C@@H]1CC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376833
PubChem CID:	11186112
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8215	Crepis zacintha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7646	Edgeworthia chrysantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Inhibition	<	0.0	%	PMID[483330]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Inhibition	=	18.1	%	PMID[483330]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Inhibition	=	6.7	%	PMID[483330]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Inhibition	=	19.8	%	PMID[483330]

☑ 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 NPC164295 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	440
0.1-0.2	1625
0.2-0.3	3391
0.3-0.4	9025
0.4-0.5	9668
0.5-0.6	4738
0.6-0.7	9236
0.7-0.8	4366
0.8-0.85	158
0.85-0.9	39
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.984	High Similarity	NPC239134
0.9597	High Similarity	NPC474737
0.9462	High Similarity	NPC471670
0.9453	High Similarity	NPC183103
0.9127	High Similarity	NPC75432
0.9098	High Similarity	NPC186647
0.9084	High Similarity	NPC470406
0.8984	High Similarity	NPC177925
0.8955	High Similarity	NPC290601
0.8947	High Similarity	NPC22644
0.8931	High Similarity	NPC279596
0.8915	High Similarity	NPC78364
0.8915	High Similarity	NPC176130
0.8915	High Similarity	NPC69424
0.8915	High Similarity	NPC84672
0.8913	High Similarity	NPC196941
0.8913	High Similarity	NPC309169
0.8872	High Similarity	NPC213122
0.8806	High Similarity	NPC89504
0.8806	High Similarity	NPC95485
0.8806	High Similarity	NPC88065
0.8788	High Similarity	NPC471851
0.8779	High Similarity	NPC57552
0.8769	High Similarity	NPC72667
0.8769	High Similarity	NPC428300
0.8723	High Similarity	NPC52692
0.8722	High Similarity	NPC312560
0.8712	High Similarity	NPC108129
0.8712	High Similarity	NPC470725
0.8705	High Similarity	NPC167663
0.8692	High Similarity	NPC254492
0.8686	High Similarity	NPC470407
0.8657	High Similarity	NPC78307
0.8657	High Similarity	NPC477139
0.8643	High Similarity	NPC472836
0.8643	High Similarity	NPC290038
0.8636	High Similarity	NPC303910
0.8636	High Similarity	NPC171460
0.8636	High Similarity	NPC276238
0.8636	High Similarity	NPC206028
0.8633	High Similarity	NPC201297
0.8593	High Similarity	NPC1249
0.8593	High Similarity	NPC202225
0.8582	High Similarity	NPC49282
0.8571	High Similarity	NPC53016
0.8561	High Similarity	NPC3009
0.8551	High Similarity	NPC223336
0.855	High Similarity	NPC474264
0.8538	High Similarity	NPC199273
0.8511	High Similarity	NPC308006
0.8511	High Similarity	NPC260152
0.8492	Intermediate Similarity	NPC469954
0.8478	Intermediate Similarity	NPC233707
0.8462	Intermediate Similarity	NPC478163
0.8456	Intermediate Similarity	NPC324117
0.8456	Intermediate Similarity	NPC209858
0.8451	Intermediate Similarity	NPC478019
0.844	Intermediate Similarity	NPC163948
0.8425	Intermediate Similarity	NPC27615
0.8421	Intermediate Similarity	NPC96024
0.8413	Intermediate Similarity	NPC312105
0.8406	Intermediate Similarity	NPC475957
0.8403	Intermediate Similarity	NPC475848
0.8403	Intermediate Similarity	NPC474306
0.8403	Intermediate Similarity	NPC95526
0.8403	Intermediate Similarity	NPC472841
0.8397	Intermediate Similarity	NPC30216
0.8397	Intermediate Similarity	NPC56332
0.8385	Intermediate Similarity	NPC282577
0.8382	Intermediate Similarity	NPC111845
0.8382	Intermediate Similarity	NPC59459
0.838	Intermediate Similarity	NPC189650
0.8369	Intermediate Similarity	NPC141817
0.8369	Intermediate Similarity	NPC176030
0.8369	Intermediate Similarity	NPC229218
0.8369	Intermediate Similarity	NPC125134
0.8369	Intermediate Similarity	NPC86455
0.8369	Intermediate Similarity	NPC192597
0.8369	Intermediate Similarity	NPC169214
0.8369	Intermediate Similarity	NPC137920
0.8369	Intermediate Similarity	NPC69755
0.8345	Intermediate Similarity	NPC329933
0.8345	Intermediate Similarity	NPC472298
0.8345	Intermediate Similarity	NPC474305
0.8333	Intermediate Similarity	NPC126767
0.8333	Intermediate Similarity	NPC118027
0.8333	Intermediate Similarity	NPC190648
0.8333	Intermediate Similarity	NPC470858
0.8333	Intermediate Similarity	NPC137750
0.8333	Intermediate Similarity	NPC312929
0.8333	Intermediate Similarity	NPC34802
0.8333	Intermediate Similarity	NPC478018
0.8333	Intermediate Similarity	NPC289042
0.8333	Intermediate Similarity	NPC245584
0.8333	Intermediate Similarity	NPC56433
0.8333	Intermediate Similarity	NPC232387
0.8322	Intermediate Similarity	NPC225351
0.8321	Intermediate Similarity	NPC182646
0.8321	Intermediate Similarity	NPC27394
0.8311	Intermediate Similarity	NPC478161
0.8311	Intermediate Similarity	NPC478159
0.831	Intermediate Similarity	NPC3732
0.8309	Intermediate Similarity	NPC474340
0.8309	Intermediate Similarity	NPC165612
0.8308	Intermediate Similarity	NPC154696
0.8296	Intermediate Similarity	NPC253488
0.8296	Intermediate Similarity	NPC245395
0.8288	Intermediate Similarity	NPC474660
0.8288	Intermediate Similarity	NPC470568
0.8286	Intermediate Similarity	NPC476191
0.8286	Intermediate Similarity	NPC1268
0.8281	Intermediate Similarity	NPC171023
0.8276	Intermediate Similarity	NPC472839
0.8276	Intermediate Similarity	NPC472056
0.8273	Intermediate Similarity	NPC470722
0.8273	Intermediate Similarity	NPC470721
0.8273	Intermediate Similarity	NPC6100
0.8273	Intermediate Similarity	NPC156888
0.8273	Intermediate Similarity	NPC301341
0.8248	Intermediate Similarity	NPC138472
0.8235	Intermediate Similarity	NPC301717
0.8231	Intermediate Similarity	NPC124842
0.8231	Intermediate Similarity	NPC472838
0.8231	Intermediate Similarity	NPC306011
0.8231	Intermediate Similarity	NPC470569
0.8214	Intermediate Similarity	NPC23870
0.8203	Intermediate Similarity	NPC25648
0.8201	Intermediate Similarity	NPC307401
0.82	Intermediate Similarity	NPC272196
0.8195	Intermediate Similarity	NPC123506
0.8182	Intermediate Similarity	NPC11799
0.8182	Intermediate Similarity	NPC84266
0.8182	Intermediate Similarity	NPC215451
0.8182	Intermediate Similarity	NPC474691
0.8182	Intermediate Similarity	NPC471187
0.8182	Intermediate Similarity	NPC100242
0.8182	Intermediate Similarity	NPC277369
0.8182	Intermediate Similarity	NPC141252
0.8176	Intermediate Similarity	NPC44606
0.8176	Intermediate Similarity	NPC164912
0.8176	Intermediate Similarity	NPC40356
0.8176	Intermediate Similarity	NPC10429
0.8176	Intermediate Similarity	NPC154683
0.8169	Intermediate Similarity	NPC149780
0.8169	Intermediate Similarity	NPC124365
0.8169	Intermediate Similarity	NPC263337
0.8163	Intermediate Similarity	NPC255641
0.8163	Intermediate Similarity	NPC290954
0.8163	Intermediate Similarity	NPC473466
0.8163	Intermediate Similarity	NPC294646
0.8163	Intermediate Similarity	NPC147735
0.8163	Intermediate Similarity	NPC225854
0.816	Intermediate Similarity	NPC23332
0.816	Intermediate Similarity	NPC470723
0.8148	Intermediate Similarity	NPC181675
0.8146	Intermediate Similarity	NPC472299
0.8143	Intermediate Similarity	NPC24394
0.8143	Intermediate Similarity	NPC119542
0.8143	Intermediate Similarity	NPC284184
0.8138	Intermediate Similarity	NPC281398
0.8138	Intermediate Similarity	NPC39361
0.8138	Intermediate Similarity	NPC473927
0.8133	Intermediate Similarity	NPC474360
0.8129	Intermediate Similarity	NPC153088
0.8125	Intermediate Similarity	NPC19896
0.8125	Intermediate Similarity	NPC245522
0.8125	Intermediate Similarity	NPC471451
0.8125	Intermediate Similarity	NPC114513
0.8125	Intermediate Similarity	NPC471305
0.8121	Intermediate Similarity	NPC62051
0.812	Intermediate Similarity	NPC181334
0.812	Intermediate Similarity	NPC111088
0.8112	Intermediate Similarity	NPC11314
0.8112	Intermediate Similarity	NPC308572
0.8112	Intermediate Similarity	NPC94076
0.8112	Intermediate Similarity	NPC182255
0.8108	Intermediate Similarity	NPC474414
0.8108	Intermediate Similarity	NPC478148
0.8108	Intermediate Similarity	NPC144283
0.8108	Intermediate Similarity	NPC473201
0.8108	Intermediate Similarity	NPC474417
0.8108	Intermediate Similarity	NPC118427
0.8108	Intermediate Similarity	NPC149526
0.8108	Intermediate Similarity	NPC302783
0.8108	Intermediate Similarity	NPC48671
0.8106	Intermediate Similarity	NPC152946
0.8106	Intermediate Similarity	NPC176208
0.8106	Intermediate Similarity	NPC11250
0.8102	Intermediate Similarity	NPC470976
0.8102	Intermediate Similarity	NPC470977
0.8102	Intermediate Similarity	NPC196979
0.8102	Intermediate Similarity	NPC477412
0.8102	Intermediate Similarity	NPC258073
0.8099	Intermediate Similarity	NPC471853
0.8099	Intermediate Similarity	NPC109007
0.8099	Intermediate Similarity	NPC109232
0.8095	Intermediate Similarity	NPC158338
0.8095	Intermediate Similarity	NPC100985
0.8095	Intermediate Similarity	NPC300983
0.8095	Intermediate Similarity	NPC97028

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 NPC164295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	979
0.2-0.3	1281
0.3-0.4	2548
0.4-0.5	2149
0.5-0.6	1126
0.6-0.7	561
0.7-0.8	109
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8819	High Similarity	NPD3972	Approved
0.8561	High Similarity	NPD7003	Approved
0.8504	High Similarity	NPD1651	Approved
0.8308	Intermediate Similarity	NPD1281	Approved
0.8258	Intermediate Similarity	NPD1876	Approved
0.8219	Intermediate Similarity	NPD7458	Discontinued
0.812	Intermediate Similarity	NPD1283	Approved
0.8102	Intermediate Similarity	NPD8032	Phase 2
0.8077	Intermediate Similarity	NPD5691	Approved
0.8015	Intermediate Similarity	NPD4626	Approved
0.8015	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6273	Approved
0.8	Intermediate Similarity	NPD2798	Approved
0.7958	Intermediate Similarity	NPD2346	Discontinued
0.7914	Intermediate Similarity	NPD2979	Phase 3
0.7847	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2799	Discontinued
0.7803	Intermediate Similarity	NPD3024	Approved
0.7803	Intermediate Similarity	NPD3025	Approved
0.7763	Intermediate Similarity	NPD7819	Suspended
0.7762	Intermediate Similarity	NPD6099	Approved
0.7762	Intermediate Similarity	NPD2935	Discontinued
0.7762	Intermediate Similarity	NPD2796	Approved
0.7762	Intermediate Similarity	NPD6100	Approved
0.7744	Intermediate Similarity	NPD3019	Approved
0.7733	Intermediate Similarity	NPD3226	Approved
0.7733	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD3023	Approved
0.7687	Intermediate Similarity	NPD3026	Approved
0.7676	Intermediate Similarity	NPD1607	Approved
0.7671	Intermediate Similarity	NPD4628	Phase 3
0.7669	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5327	Phase 3
0.7639	Intermediate Similarity	NPD2531	Phase 2
0.7639	Intermediate Similarity	NPD2438	Suspended
0.763	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1241	Discontinued
0.7612	Intermediate Similarity	NPD2932	Approved
0.761	Intermediate Similarity	NPD7473	Discontinued
0.7597	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1471	Phase 3
0.758	Intermediate Similarity	NPD6959	Discontinued
0.7569	Intermediate Similarity	NPD3748	Approved
0.7552	Intermediate Similarity	NPD4097	Suspended
0.7535	Intermediate Similarity	NPD1240	Approved
0.7534	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD1201	Approved
0.7482	Intermediate Similarity	NPD4624	Approved
0.7481	Intermediate Similarity	NPD17	Approved
0.7467	Intermediate Similarity	NPD2532	Approved
0.7467	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2534	Approved
0.7467	Intermediate Similarity	NPD2533	Approved
0.7466	Intermediate Similarity	NPD2344	Approved
0.7462	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6599	Discontinued
0.7448	Intermediate Similarity	NPD1510	Phase 2
0.7432	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4307	Phase 2
0.7413	Intermediate Similarity	NPD4140	Approved
0.741	Intermediate Similarity	NPD3267	Approved
0.741	Intermediate Similarity	NPD1470	Approved
0.741	Intermediate Similarity	NPD3266	Approved
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD5494	Approved
0.74	Intermediate Similarity	NPD7390	Discontinued
0.7394	Intermediate Similarity	NPD2313	Discontinued
0.7391	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD5536	Phase 2
0.7372	Intermediate Similarity	NPD5978	Approved
0.7372	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5977	Approved
0.7368	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1608	Approved
0.7315	Intermediate Similarity	NPD3750	Approved
0.7315	Intermediate Similarity	NPD8166	Discontinued
0.731	Intermediate Similarity	NPD6651	Approved
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5951	Approved
0.7292	Intermediate Similarity	NPD3140	Approved
0.7292	Intermediate Similarity	NPD3142	Approved
0.729	Intermediate Similarity	NPD6873	Phase 2
0.729	Intermediate Similarity	NPD7411	Suspended
0.7286	Intermediate Similarity	NPD2797	Approved
0.7279	Intermediate Similarity	NPD5406	Approved
0.7279	Intermediate Similarity	NPD5404	Approved
0.7279	Intermediate Similarity	NPD5405	Approved
0.7279	Intermediate Similarity	NPD5408	Approved
0.7279	Intermediate Similarity	NPD4476	Approved
0.7279	Intermediate Similarity	NPD5585	Approved
0.7279	Intermediate Similarity	NPD4477	Approved
0.7273	Intermediate Similarity	NPD3268	Approved
0.7267	Intermediate Similarity	NPD2309	Approved
0.7254	Intermediate Similarity	NPD6832	Phase 2
0.7248	Intermediate Similarity	NPD1243	Approved
0.7246	Intermediate Similarity	NPD1611	Approved
0.7239	Intermediate Similarity	NPD7177	Discontinued
0.7226	Intermediate Similarity	NPD1778	Approved
0.7226	Intermediate Similarity	NPD4380	Phase 2
0.7226	Intermediate Similarity	NPD7028	Phase 2
0.7222	Intermediate Similarity	NPD6663	Approved
0.7218	Intermediate Similarity	NPD5283	Phase 1
0.7211	Intermediate Similarity	NPD4308	Phase 3
0.7203	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7008	Discontinued
0.7197	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9494	Approved
0.7183	Intermediate Similarity	NPD5736	Approved
0.7181	Intermediate Similarity	NPD1549	Phase 2
0.7172	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4060	Phase 1
0.7172	Intermediate Similarity	NPD3620	Phase 2
0.7153	Intermediate Similarity	NPD3764	Approved
0.7133	Intermediate Similarity	NPD2800	Approved
0.7124	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5735	Approved
0.7123	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3657	Discovery
0.7114	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7095	Approved
0.7077	Intermediate Similarity	NPD3134	Approved
0.7075	Intermediate Similarity	NPD6353	Approved
0.7075	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7075	Discontinued
0.7059	Intermediate Similarity	NPD6799	Approved
0.7059	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3110	Approved
0.7055	Intermediate Similarity	NPD3109	Approved
0.7051	Intermediate Similarity	NPD2649	Approved
0.7051	Intermediate Similarity	NPD2651	Approved
0.7045	Intermediate Similarity	NPD5451	Approved
0.7039	Intermediate Similarity	NPD3887	Approved
0.7039	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8127	Discontinued
0.7034	Intermediate Similarity	NPD6798	Discontinued
0.7034	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7427	Discontinued
0.7025	Intermediate Similarity	NPD1934	Approved
0.7025	Intermediate Similarity	NPD7577	Discontinued
0.7025	Intermediate Similarity	NPD6280	Approved
0.7025	Intermediate Similarity	NPD6279	Approved
0.7025	Intermediate Similarity	NPD6801	Discontinued
0.7021	Intermediate Similarity	NPD4359	Approved
0.7021	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5535	Approved
0.7012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7644	Approved
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD2353	Approved
0.7	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7236	Approved
0.6993	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3495	Discontinued
0.6982	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2801	Approved
0.6978	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4110	Phase 3
0.6972	Remote Similarity	NPD6696	Suspended
0.6966	Remote Similarity	NPD4625	Phase 3
0.6957	Remote Similarity	NPD3091	Approved
0.6957	Remote Similarity	NPD9545	Approved
0.6957	Remote Similarity	NPD3749	Approved
0.6948	Remote Similarity	NPD1511	Approved
0.6937	Remote Similarity	NPD3817	Phase 2
0.6929	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD920	Approved
0.6918	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7294	Phase 1
0.6918	Remote Similarity	NPD37	Approved
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD411	Approved
0.6909	Remote Similarity	NPD6894	Phase 1
0.6908	Remote Similarity	NPD2654	Approved
0.6903	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1669	Approved
0.6897	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3882	Suspended
0.6894	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4618	Approved
0.6892	Remote Similarity	NPD1933	Approved
0.6892	Remote Similarity	NPD4622	Approved
0.689	Remote Similarity	NPD5711	Approved
0.689	Remote Similarity	NPD7229	Phase 3
0.689	Remote Similarity	NPD5710	Approved
0.6882	Remote Similarity	NPD8312	Approved
0.6882	Remote Similarity	NPD8313	Approved
0.6879	Remote Similarity	NPD6287	Discontinued

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