NPASS Compound

Structure

CID78307 OpenBabel06191715412D 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 -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 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 2.5981 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 -0.8660 1.5000 0.0000 C 0 0 1 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 3.4641 0.0000 0.0000 O 0 0 0 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 15 2 0 0 0 0 11 12 1 0 0 0 0 12 15 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 18 1 0 0 0 0 17 23 1 1 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	3.988
LogD:	1.801
LogS:	-3.479
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.815
Synthetic Accessibility Score:	4.102
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.669
MDCK Permeability:	1.9608492948464118e-05
Pgp-inhibitor:	0.362
Pgp-substrate:	0.153
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.911
30% Bioavailability (F30%):	0.8

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.537
Plasma Protein Binding (PPB):	91.26435089111328%
Volume Distribution (VD):	2.788
Pgp-substrate:	15.692180633544922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.822
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.385
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.208
CYP2D6-substrate:	0.489
CYP3A4-inhibitor:	0.217
CYP3A4-substrate:	0.587

ADMET: Excretion

Clearance (CL):	4.572
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.474
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.538
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.702
Carcinogencity:	0.017
Eye Corrosion:	0.004
Eye Irritation:	0.834
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC78307

Natural Product ID:	NPC78307
*Common Name:**	6-Alpha-Hydroxysugiol
IUPAC Name:	(4aS,10R,10aS)-6,10-dihydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
Synonyms:
Standard InCHIKey:	VQGOEQIXFUUUQP-CMKODMSKSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-11(2)12-9-13-14(10-15(12)21)20(5)8-6-7-19(3,4)18(20)17(23)16(13)22/h9-11,17-18,21,23H,6-8H2,1-5H3/t17-,18-,20+/m0/s1
SMILES:	CC(C)c1cc2c(cc1O)[C@@]1(C)CCCC(C)(C)[C@@H]1[C@H](C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3814903
PubChem CID:	12114761
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
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17869103]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26905523]
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]
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]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
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[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	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]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	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]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	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	4
Others	2

Activity Type	# Activity
Cell Line	2
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	36000.0	nM	PMID[502704]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7700.0	nM	PMID[502705]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	24600.0	nM	PMID[502704]
NPT2	Others	Unspecified		Ratio IC50	=	1.5	n.a.	PMID[502704]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	17100.0	nM	PMID[502704]
NPT2	Others	Unspecified		Ratio IC50	=	2.1	n.a.	PMID[502704]

☑ 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 NPC78307 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	314
0.1-0.2	1354
0.2-0.3	2786
0.3-0.4	7127
0.4-0.5	11105
0.5-0.6	7032
0.6-0.7	9638
0.7-0.8	2979
0.8-0.85	280
0.85-0.9	53
0.9-0.95	17
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9692	High Similarity	NPC475957
0.9685	High Similarity	NPC471851
0.9528	High Similarity	NPC171460
0.9524	High Similarity	NPC69424
0.9524	High Similarity	NPC84672
0.9524	High Similarity	NPC176130
0.9524	High Similarity	NPC78364
0.9462	High Similarity	NPC202225
0.9385	High Similarity	NPC477139
0.937	High Similarity	NPC72667
0.9302	High Similarity	NPC108129
0.9297	High Similarity	NPC3009
0.9291	High Similarity	NPC254492
0.9225	High Similarity	NPC303910
0.9225	High Similarity	NPC276238
0.9191	High Similarity	NPC248068
0.9134	High Similarity	NPC199273
0.9134	High Similarity	NPC181334
0.9062	High Similarity	NPC137750
0.9062	High Similarity	NPC123506
0.9055	High Similarity	NPC471187
0.9051	High Similarity	NPC308572
0.9	High Similarity	NPC96024
0.8993	High Similarity	NPC478160
0.8976	High Similarity	NPC282577
0.8947	High Similarity	NPC111845
0.8939	High Similarity	NPC476847
0.8905	High Similarity	NPC471853
0.8898	High Similarity	NPC154696
0.8889	High Similarity	NPC471670
0.8865	High Similarity	NPC5568
0.8849	High Similarity	NPC478164
0.8846	High Similarity	NPC71610
0.8828	High Similarity	NPC11250
0.8806	High Similarity	NPC138472
0.8797	High Similarity	NPC93015
0.8779	High Similarity	NPC262936
0.8779	High Similarity	NPC30491
0.8777	High Similarity	NPC477209
0.8769	High Similarity	NPC87985
0.876	High Similarity	NPC273683
0.876	High Similarity	NPC198014
0.8759	High Similarity	NPC230811
0.8714	High Similarity	NPC100242
0.8682	High Similarity	NPC176208
0.8676	High Similarity	NPC153088
0.8672	High Similarity	NPC259703
0.8672	High Similarity	NPC32322
0.8667	High Similarity	NPC52407
0.8662	High Similarity	NPC143685
0.8657	High Similarity	NPC164295
0.8652	High Similarity	NPC471906
0.8643	High Similarity	NPC135524
0.8605	High Similarity	NPC249340
0.8605	High Similarity	NPC162935
0.8605	High Similarity	NPC253627
0.8593	High Similarity	NPC165612
0.8582	High Similarity	NPC253488
0.8571	High Similarity	NPC229894
0.8571	High Similarity	NPC305845
0.8571	High Similarity	NPC308311
0.8571	High Similarity	NPC204045
0.8571	High Similarity	NPC477137
0.8571	High Similarity	NPC38893
0.8561	High Similarity	NPC15837
0.8551	High Similarity	NPC477592
0.8551	High Similarity	NPC36868
0.855	High Similarity	NPC68756
0.855	High Similarity	NPC152525
0.8529	High Similarity	NPC49742
0.8529	High Similarity	NPC314048
0.8527	High Similarity	NPC472981
0.8521	High Similarity	NPC79627
0.8519	High Similarity	NPC291001
0.8519	High Similarity	NPC41847
0.8519	High Similarity	NPC18798
0.8519	High Similarity	NPC239134
0.8516	High Similarity	NPC473767
0.8516	High Similarity	NPC476645
0.8511	High Similarity	NPC474961
0.8507	High Similarity	NPC117899
0.85	High Similarity	NPC476534
0.8492	Intermediate Similarity	NPC35797
0.8492	Intermediate Similarity	NPC192948
0.8478	Intermediate Similarity	NPC474311
0.8473	Intermediate Similarity	NPC275145
0.8467	Intermediate Similarity	NPC23894
0.8462	Intermediate Similarity	NPC120545
0.8444	Intermediate Similarity	NPC27659
0.8444	Intermediate Similarity	NPC199253
0.8444	Intermediate Similarity	NPC136588
0.8438	Intermediate Similarity	NPC471671
0.8433	Intermediate Similarity	NPC48248
0.8433	Intermediate Similarity	NPC193203
0.8425	Intermediate Similarity	NPC219112
0.8417	Intermediate Similarity	NPC53001
0.8417	Intermediate Similarity	NPC277559
0.8417	Intermediate Similarity	NPC49911
0.8409	Intermediate Similarity	NPC74507
0.8409	Intermediate Similarity	NPC234890
0.8409	Intermediate Similarity	NPC164014
0.8406	Intermediate Similarity	NPC477596
0.8406	Intermediate Similarity	NPC22644
0.8406	Intermediate Similarity	NPC103082
0.8403	Intermediate Similarity	NPC477208
0.8397	Intermediate Similarity	NPC91478
0.8397	Intermediate Similarity	NPC121168
0.8394	Intermediate Similarity	NPC4170
0.8394	Intermediate Similarity	NPC59459
0.8392	Intermediate Similarity	NPC309169
0.8392	Intermediate Similarity	NPC244691
0.8392	Intermediate Similarity	NPC196941
0.8385	Intermediate Similarity	NPC241001
0.838	Intermediate Similarity	NPC201297
0.8372	Intermediate Similarity	NPC469644
0.8369	Intermediate Similarity	NPC181560
0.8369	Intermediate Similarity	NPC169452
0.8359	Intermediate Similarity	NPC304510
0.8359	Intermediate Similarity	NPC477136
0.8359	Intermediate Similarity	NPC172219
0.8359	Intermediate Similarity	NPC174087
0.8357	Intermediate Similarity	NPC477593
0.8357	Intermediate Similarity	NPC87723
0.8356	Intermediate Similarity	NPC474310
0.8346	Intermediate Similarity	NPC147179
0.8345	Intermediate Similarity	NPC86524
0.8345	Intermediate Similarity	NPC478163
0.8345	Intermediate Similarity	NPC472308
0.8345	Intermediate Similarity	NPC315275
0.8345	Intermediate Similarity	NPC191976
0.8333	Intermediate Similarity	NPC50924
0.8333	Intermediate Similarity	NPC477594
0.8333	Intermediate Similarity	NPC12070
0.8333	Intermediate Similarity	NPC34482
0.8321	Intermediate Similarity	NPC70622
0.8321	Intermediate Similarity	NPC312560
0.831	Intermediate Similarity	NPC2681
0.831	Intermediate Similarity	NPC272907
0.8309	Intermediate Similarity	NPC31799
0.8309	Intermediate Similarity	NPC470725
0.8308	Intermediate Similarity	NPC478121
0.8308	Intermediate Similarity	NPC190501
0.8308	Intermediate Similarity	NPC318552
0.8298	Intermediate Similarity	NPC138099
0.8298	Intermediate Similarity	NPC242994
0.8298	Intermediate Similarity	NPC190457
0.8286	Intermediate Similarity	NPC119542
0.8286	Intermediate Similarity	NPC471905
0.8284	Intermediate Similarity	NPC269598
0.8284	Intermediate Similarity	NPC474737
0.8281	Intermediate Similarity	NPC469663
0.8281	Intermediate Similarity	NPC92
0.8281	Intermediate Similarity	NPC308828
0.8276	Intermediate Similarity	NPC136878
0.8276	Intermediate Similarity	NPC470570
0.8276	Intermediate Similarity	NPC314437
0.8273	Intermediate Similarity	NPC249272
0.8273	Intermediate Similarity	NPC283088
0.8273	Intermediate Similarity	NPC80035
0.8271	Intermediate Similarity	NPC142956
0.8271	Intermediate Similarity	NPC173978
0.8271	Intermediate Similarity	NPC12818
0.8268	Intermediate Similarity	NPC268160
0.8264	Intermediate Similarity	NPC48762
0.8264	Intermediate Similarity	NPC29932
0.8261	Intermediate Similarity	NPC18982
0.8261	Intermediate Similarity	NPC225051
0.8261	Intermediate Similarity	NPC267205
0.8261	Intermediate Similarity	NPC114183
0.8261	Intermediate Similarity	NPC475346
0.8261	Intermediate Similarity	NPC115458
0.8261	Intermediate Similarity	NPC475457
0.8261	Intermediate Similarity	NPC475627
0.8252	Intermediate Similarity	NPC193555
0.8252	Intermediate Similarity	NPC85310
0.8252	Intermediate Similarity	NPC469855
0.8252	Intermediate Similarity	NPC184935
0.8252	Intermediate Similarity	NPC471971
0.8252	Intermediate Similarity	NPC469520
0.8252	Intermediate Similarity	NPC30846
0.8252	Intermediate Similarity	NPC471972
0.8248	Intermediate Similarity	NPC72669
0.8248	Intermediate Similarity	NPC85342
0.8248	Intermediate Similarity	NPC474517
0.8244	Intermediate Similarity	NPC216216
0.8244	Intermediate Similarity	NPC190971
0.8235	Intermediate Similarity	NPC99731
0.8231	Intermediate Similarity	NPC477221
0.8231	Intermediate Similarity	NPC42657
0.8227	Intermediate Similarity	NPC4214
0.8227	Intermediate Similarity	NPC13715
0.8222	Intermediate Similarity	NPC19432
0.8219	Intermediate Similarity	NPC472135
0.8219	Intermediate Similarity	NPC52692
0.8214	Intermediate Similarity	NPC38158
0.8214	Intermediate Similarity	NPC254847
0.8207	Intermediate Similarity	NPC478019
0.8207	Intermediate Similarity	NPC170055
0.8203	Intermediate Similarity	NPC322197
0.8201	Intermediate Similarity	NPC474659

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 NPC78307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	934
0.2-0.3	1334
0.3-0.4	2583
0.4-0.5	2189
0.5-0.6	1261
0.6-0.7	499
0.7-0.8	60
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8308	Intermediate Similarity	NPD3019	Approved
0.8231	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD2932	Approved
0.8045	Intermediate Similarity	NPD1201	Approved
0.7941	Intermediate Similarity	NPD1470	Approved
0.7931	Intermediate Similarity	NPD7003	Approved
0.7891	Intermediate Similarity	NPD7390	Discontinued
0.7879	Intermediate Similarity	NPD3091	Approved
0.7857	Intermediate Similarity	NPD6663	Approved
0.7826	Intermediate Similarity	NPD5736	Approved
0.7778	Intermediate Similarity	NPD5408	Approved
0.7778	Intermediate Similarity	NPD5404	Approved
0.7778	Intermediate Similarity	NPD5406	Approved
0.7778	Intermediate Similarity	NPD5405	Approved
0.7748	Intermediate Similarity	NPD7458	Discontinued
0.7718	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD5951	Approved
0.7704	Intermediate Similarity	NPD3026	Approved
0.7704	Intermediate Similarity	NPD3023	Approved
0.7687	Intermediate Similarity	NPD3024	Approved
0.7687	Intermediate Similarity	NPD3025	Approved
0.7667	Intermediate Similarity	NPD6273	Approved
0.7647	Intermediate Similarity	NPD3092	Approved
0.7594	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD3972	Approved
0.7586	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8166	Discontinued
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3095	Discontinued
0.7467	Intermediate Similarity	NPD3300	Phase 2
0.745	Intermediate Similarity	NPD4628	Phase 3
0.7429	Intermediate Similarity	NPD3094	Phase 2
0.74	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6959	Discontinued
0.7372	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1283	Approved
0.7351	Intermediate Similarity	NPD7236	Approved
0.7344	Intermediate Similarity	NPD1237	Approved
0.7343	Intermediate Similarity	NPD7008	Discontinued
0.7308	Intermediate Similarity	NPD2342	Discontinued
0.7305	Intermediate Similarity	NPD1164	Approved
0.7299	Intermediate Similarity	NPD1651	Approved
0.7297	Intermediate Similarity	NPD6099	Approved
0.7297	Intermediate Similarity	NPD6100	Approved
0.7297	Intermediate Similarity	NPD2935	Discontinued
0.7293	Intermediate Similarity	NPD7635	Approved
0.7273	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2346	Discontinued
0.7246	Intermediate Similarity	NPD4059	Approved
0.7246	Intermediate Similarity	NPD4626	Approved
0.723	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7239	Suspended
0.7222	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7819	Suspended
0.7212	Intermediate Similarity	NPD5844	Phase 1
0.7211	Intermediate Similarity	NPD1607	Approved
0.7195	Intermediate Similarity	NPD7473	Discontinued
0.7192	Intermediate Similarity	NPD943	Approved
0.7185	Intermediate Similarity	NPD2629	Approved
0.7179	Intermediate Similarity	NPD3226	Approved
0.7176	Intermediate Similarity	NPD8150	Discontinued
0.7172	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7133	Intermediate Similarity	NPD2798	Approved
0.7117	Intermediate Similarity	NPD6232	Discontinued
0.7114	Intermediate Similarity	NPD1510	Phase 2
0.7114	Intermediate Similarity	NPD2799	Discontinued
0.7113	Intermediate Similarity	NPD1876	Approved
0.7107	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD9545	Approved
0.7086	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7075	Discontinued
0.7075	Intermediate Similarity	NPD4060	Phase 1
0.7075	Intermediate Similarity	NPD3620	Phase 2
0.7075	Intermediate Similarity	NPD4140	Approved
0.7075	Intermediate Similarity	NPD1240	Approved
0.7075	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1809	Phase 2
0.705	Intermediate Similarity	NPD5691	Approved
0.7045	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1755	Approved
0.7031	Intermediate Similarity	NPD3020	Approved
0.7029	Intermediate Similarity	NPD7610	Discontinued
0.7025	Intermediate Similarity	NPD6599	Discontinued
0.702	Intermediate Similarity	NPD2344	Approved
0.7011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD288	Approved
0.7007	Intermediate Similarity	NPD8032	Phase 2
0.7	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4097	Suspended
0.6974	Remote Similarity	NPD1549	Phase 2
0.6972	Remote Similarity	NPD4878	Approved
0.6966	Remote Similarity	NPD4208	Discontinued
0.6959	Remote Similarity	NPD2979	Phase 3
0.6954	Remote Similarity	NPD2796	Approved
0.6948	Remote Similarity	NPD6190	Approved
0.694	Remote Similarity	NPD4750	Phase 3
0.6937	Remote Similarity	NPD6801	Discontinued
0.6929	Remote Similarity	NPD844	Approved
0.6928	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6166	Phase 2
0.6923	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7742	Approved
0.6887	Remote Similarity	NPD7743	Approved
0.6883	Remote Similarity	NPD3750	Approved
0.6879	Remote Similarity	NPD2286	Discontinued
0.6875	Remote Similarity	NPD3495	Discontinued
0.6875	Remote Similarity	NPD7411	Suspended
0.687	Remote Similarity	NPD1930	Approved
0.687	Remote Similarity	NPD1929	Approved
0.687	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6651	Approved
0.6861	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD9494	Approved
0.6846	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7177	Discontinued
0.6842	Remote Similarity	NPD5034	Approved
0.6842	Remote Similarity	NPD4955	Approved
0.6842	Remote Similarity	NPD2438	Suspended
0.6842	Remote Similarity	NPD36	Approved
0.6842	Remote Similarity	NPD5026	Approved
0.6842	Remote Similarity	NPD5028	Approved
0.6842	Remote Similarity	NPD4954	Approved
0.6839	Remote Similarity	NPD2309	Approved
0.6838	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6535	Approved
0.6836	Remote Similarity	NPD6534	Approved
0.6835	Remote Similarity	NPD9493	Approved
0.6832	Remote Similarity	NPD1934	Approved
0.6831	Remote Similarity	NPD4879	Approved
0.6824	Remote Similarity	NPD6798	Discontinued
0.6815	Remote Similarity	NPD3022	Approved
0.6815	Remote Similarity	NPD3021	Approved
0.681	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3882	Suspended
0.681	Remote Similarity	NPD7057	Phase 3
0.681	Remote Similarity	NPD7058	Phase 2
0.6809	Remote Similarity	NPD4093	Discontinued
0.6806	Remote Similarity	NPD5327	Phase 3
0.6802	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8313	Approved
0.6802	Remote Similarity	NPD8312	Approved
0.68	Remote Similarity	NPD5735	Approved
0.68	Remote Similarity	NPD6355	Discontinued
0.68	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2860	Approved
0.6797	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2859	Approved
0.6797	Remote Similarity	NPD1471	Phase 3
0.6784	Remote Similarity	NPD5030	Phase 2
0.6783	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4624	Approved
0.6779	Remote Similarity	NPD7961	Discontinued
0.6772	Remote Similarity	NPD845	Approved
0.6769	Remote Similarity	NPD2066	Phase 3
0.6765	Remote Similarity	NPD4956	Approved
0.6763	Remote Similarity	NPD3317	Approved
0.6761	Remote Similarity	NPD1751	Approved
0.6748	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8127	Discontinued
0.6742	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD74	Approved
0.6741	Remote Similarity	NPD9266	Approved
0.674	Remote Similarity	NPD6780	Approved
0.674	Remote Similarity	NPD6776	Approved
0.674	Remote Similarity	NPD6777	Approved
0.674	Remote Similarity	NPD6782	Approved
0.674	Remote Similarity	NPD6779	Approved
0.674	Remote Similarity	NPD6781	Approved
0.674	Remote Similarity	NPD6778	Approved
0.6739	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2531	Phase 2
0.6732	Remote Similarity	NPD4477	Approved
0.6732	Remote Similarity	NPD4476	Approved
0.6728	Remote Similarity	NPD37	Approved
0.6726	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7700	Phase 2

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