NPASS Compound

Structure

NPC212369 OpenBabel07101718222D 24 27 0 0 1 0 0 0 0 0999 V2000 -4.4300 -2.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3336 -1.0086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -3.5000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 1.7321 -2.0000 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 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 2.5981 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 0.0000 0.0000 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 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 16 2 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 18 20 1 6 0 0 0 18 21 1 0 0 0 0 20 3 1 6 0 0 0 21 4 1 1 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.2
Volume:	353.371
LogP:	5.252
LogD:	3.943
LogS:	-3.86
# Rotatable Bonds:	0
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.639
Synthetic Accessibility Score:	4.121
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	2.024173409154173e-05
Pgp-inhibitor:	0.138
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.069
30% Bioavailability (F30%):	0.766

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	97.5885009765625%
Volume Distribution (VD):	3.693
Pgp-substrate:	3.1386799812316895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.173
CYP1A2-substrate:	0.806
CYP2C19-inhibitor:	0.263
CYP2C19-substrate:	0.707
CYP2C9-inhibitor:	0.285
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.331
CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.834
CYP3A4-substrate:	0.732

ADMET: Excretion

Clearance (CL):	20.747
Half-life (T1/2):	0.371

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.176
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.602
Maximum Recommended Daily Dose:	0.817
Skin Sensitization:	0.89
Carcinogencity:	0.903
Eye Corrosion:	0.018
Eye Irritation:	0.565
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC212369

Natural Product ID:	NPC212369
*Common Name:**	Puupehenone
IUPAC Name:	(4aS,6aS,12aR,12bS)-10-hydroxy-4,4,6a,12b-tetramethyl-2,3,4a,5,6,12a-hexahydro-1H-benzo[a]xanthen-9-one
Synonyms:	Puupehenone
Standard InCHIKey:	LOCMLXSTDCXZFJ-YHELAOLJSA-N
Standard InCHI:	InChI=1S/C21H28O3/c1-19(2)7-5-8-20(3)17(19)6-9-21(4)18(20)11-13-10-14(22)15(23)12-16(13)24-21/h10-12,17-18,22H,5-9H2,1-4H3/t17-,18+,20-,21-/m0/s1
SMILES:	O=C1C=C2O[C@@]3(C)CC[C@@H]4[C@]([C@H]3C=C2C=C1O)(C)CCCC4(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL157844
PubChem CID:	72536
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514320]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497952]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17378531]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19167886]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19783432]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	Australian	n.a.	PMID[24973030]
NPO32548	dactylospongia sp.	Species	Thorectidae	Eukaryota	n.a.	Hawaiian	n.a.	PMID[25668638]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28834433]
NPO32541	stronglyophora hartmani	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[3655802]

☑ 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
EC50	1
IC50	30
MIC	6
Others	14

Activity Type	# Activity
Cell Line	11
Individual Protein	8
NON-MOLECULAR	2
Organism	22
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.0	ug.mL-1	PMID[464314]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[464314]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[464314]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[464314]
NPT168	Cell Line	P388	Mus musculus	T/C	=	119.0	%	PMID[464314]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.2	ug.mL-1	PMID[464315]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.4	ug.mL-1	PMID[464315]
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.3	ug.mL-1	PMID[464315]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	27000.0	nM	PMID[464316]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	=	2400.0	nM	PMID[464317]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.5	ug.mL-1	PMID[464318]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	680.0	nM	PMID[464320]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	=	22000.0	nM	PMID[464320]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	FC	=	4.0	n.a.	PMID[464321]
NPT401	Cell Line	786-0	Homo sapiens	IC50	=	17700.0	nM	PMID[464321]
NPT3973	Individual Protein	Endothelial PAS domain-containing protein 1	Homo sapiens	EC50	=	3300.0	nM	PMID[464321]
NPT910	Individual Protein	Cholesteryl ester transfer protein	Homo sapiens	IC50	=	6000.0	nM	PMID[464313]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	3.0	ug.mL-1	PMID[464314]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	=	760.0	nM	PMID[464317]
NPT2	Others	Unspecified		IC50	=	8300.0	nM	PMID[464317]
NPT2	Others	Unspecified		Ratio IC50	=	11.0	n.a.	PMID[464317]
NPT2	Others	Unspecified		Ratio IC50	=	4.0	n.a.	PMID[464317]
NPT2	Others	Unspecified		Ratio IC50	=	0.2	n.a.	PMID[464317]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.5	ug.mL-1	PMID[464318]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	20.0	ug.mL-1	PMID[464318]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.6	ug.mL-1	PMID[464318]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.1	ug.mL-1	PMID[464318]
NPT554	Organism	Candida glabrata	Candida glabrata	MFC	=	10.0	ug ml-1	PMID[464319]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MFC	=	2.5	ug ml-1	PMID[464319]
NPT20	Organism	Candida albicans	Candida albicans	MFC	=	10.0	ug ml-1	PMID[464319]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MFC	=	1.25	ug ml-1	PMID[464319]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	10.0	ug.mL-1	PMID[464319]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	10.0	ug.mL-1	PMID[464319]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	2.5	ug.mL-1	PMID[464319]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	10.0	ug.mL-1	PMID[464319]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	0.63	ug.mL-1	PMID[464319]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC50	=	5.63	ug.mL-1	PMID[464319]
NPT554	Organism	Candida glabrata	Candida glabrata	IC50	=	2.67	ug.mL-1	PMID[464319]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	IC50	=	1.49	ug.mL-1	PMID[464319]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	3.02	ug.mL-1	PMID[464319]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	0.38	ug.mL-1	PMID[464319]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	=	6000.0	nM	PMID[464320]
NPT2	Others	Unspecified		IC50	=	9000.0	nM	PMID[464320]
NPT2	Others	Unspecified		IC50	=	32000.0	nM	PMID[464320]
NPT2	Others	Unspecified		IC50	=	0.9	ug.mL-1	PMID[464320]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15500.0	nM	PMID[464321]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18000.0	nM	PMID[464321]
NPT35	Others	n.a.		Activity	=	2600.0	uM	PMID[464322]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	4.0	mm	PMID[464322]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	=	3.0	mm	PMID[464322]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	99.0	%	PMID[464323]

☑ 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 NPC212369 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	201
0.1-0.2	1476
0.2-0.3	4266
0.3-0.4	8747
0.4-0.5	16334
0.5-0.6	7589
0.6-0.7	3719
0.7-0.8	360
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9318	High Similarity	NPC242637
0.8667	High Similarity	NPC38952
0.8556	High Similarity	NPC210216
0.809	Intermediate Similarity	NPC288281
0.8046	Intermediate Similarity	NPC170394
0.7921	Intermediate Similarity	NPC478052
0.7882	Intermediate Similarity	NPC22134
0.7879	Intermediate Similarity	NPC472637
0.7872	Intermediate Similarity	NPC280149
0.7872	Intermediate Similarity	NPC221111
0.7872	Intermediate Similarity	NPC223093
0.7802	Intermediate Similarity	NPC53385
0.7766	Intermediate Similarity	NPC68148
0.7766	Intermediate Similarity	NPC65615
0.7723	Intermediate Similarity	NPC476848
0.7723	Intermediate Similarity	NPC171014
0.7717	Intermediate Similarity	NPC241512
0.7717	Intermediate Similarity	NPC6185
0.7692	Intermediate Similarity	NPC75389
0.7692	Intermediate Similarity	NPC309309
0.7692	Intermediate Similarity	NPC291999
0.7684	Intermediate Similarity	NPC474209
0.7684	Intermediate Similarity	NPC475823
0.7684	Intermediate Similarity	NPC310479
0.767	Intermediate Similarity	NPC43063
0.767	Intermediate Similarity	NPC79298
0.7653	Intermediate Similarity	NPC16967
0.7629	Intermediate Similarity	NPC191521
0.7604	Intermediate Similarity	NPC472975
0.7596	Intermediate Similarity	NPC275060
0.7573	Intermediate Similarity	NPC266570
0.7573	Intermediate Similarity	NPC295843
0.7556	Intermediate Similarity	NPC108955
0.7556	Intermediate Similarity	NPC476809
0.7551	Intermediate Similarity	NPC295347
0.7549	Intermediate Similarity	NPC179208
0.7528	Intermediate Similarity	NPC476808
0.7527	Intermediate Similarity	NPC133652
0.7527	Intermediate Similarity	NPC132228
0.7527	Intermediate Similarity	NPC263997
0.7527	Intermediate Similarity	NPC8518
0.7526	Intermediate Similarity	NPC205034
0.7526	Intermediate Similarity	NPC152778
0.7526	Intermediate Similarity	NPC162615
0.75	Intermediate Similarity	NPC280592
0.75	Intermediate Similarity	NPC253177
0.75	Intermediate Similarity	NPC182136
0.75	Intermediate Similarity	NPC213636
0.75	Intermediate Similarity	NPC476927
0.75	Intermediate Similarity	NPC278673
0.75	Intermediate Similarity	NPC292589
0.75	Intermediate Similarity	NPC112680
0.75	Intermediate Similarity	NPC92275
0.7477	Intermediate Similarity	NPC44537
0.7475	Intermediate Similarity	NPC260796
0.7474	Intermediate Similarity	NPC48107
0.7474	Intermediate Similarity	NPC478261
0.7474	Intermediate Similarity	NPC478259
0.7474	Intermediate Similarity	NPC229612
0.7474	Intermediate Similarity	NPC7280
0.7474	Intermediate Similarity	NPC60765
0.7474	Intermediate Similarity	NPC478260
0.7473	Intermediate Similarity	NPC473217
0.7473	Intermediate Similarity	NPC55869
0.7473	Intermediate Similarity	NPC225515
0.7453	Intermediate Similarity	NPC103491
0.7453	Intermediate Similarity	NPC16270
0.7449	Intermediate Similarity	NPC23170
0.7449	Intermediate Similarity	NPC474328
0.7447	Intermediate Similarity	NPC471219
0.7444	Intermediate Similarity	NPC27817
0.7429	Intermediate Similarity	NPC304276
0.7429	Intermediate Similarity	NPC137462
0.7423	Intermediate Similarity	NPC296114
0.7423	Intermediate Similarity	NPC471329
0.7416	Intermediate Similarity	NPC132542
0.7404	Intermediate Similarity	NPC189863
0.7404	Intermediate Similarity	NPC81630
0.7404	Intermediate Similarity	NPC471206
0.74	Intermediate Similarity	NPC170131
0.74	Intermediate Similarity	NPC208094
0.7396	Intermediate Similarity	NPC474918
0.7396	Intermediate Similarity	NPC472688
0.7396	Intermediate Similarity	NPC472676
0.7396	Intermediate Similarity	NPC82876
0.7396	Intermediate Similarity	NPC118011
0.7396	Intermediate Similarity	NPC36668
0.7391	Intermediate Similarity	NPC304285
0.7391	Intermediate Similarity	NPC92226
0.7374	Intermediate Similarity	NPC147232
0.7363	Intermediate Similarity	NPC469637
0.7358	Intermediate Similarity	NPC228477
0.7358	Intermediate Similarity	NPC137911
0.7353	Intermediate Similarity	NPC168319
0.7353	Intermediate Similarity	NPC194028
0.7347	Intermediate Similarity	NPC263780
0.7347	Intermediate Similarity	NPC211230
0.734	Intermediate Similarity	NPC109528
0.734	Intermediate Similarity	NPC474680
0.734	Intermediate Similarity	NPC469993
0.734	Intermediate Similarity	NPC477578
0.7333	Intermediate Similarity	NPC189485
0.7327	Intermediate Similarity	NPC478056
0.7327	Intermediate Similarity	NPC181147
0.732	Intermediate Similarity	NPC113393
0.732	Intermediate Similarity	NPC273199
0.732	Intermediate Similarity	NPC78973
0.7312	Intermediate Similarity	NPC105803
0.7312	Intermediate Similarity	NPC57370
0.7312	Intermediate Similarity	NPC53733
0.7308	Intermediate Similarity	NPC40170
0.7308	Intermediate Similarity	NPC472868
0.7308	Intermediate Similarity	NPC165969
0.73	Intermediate Similarity	NPC73858
0.73	Intermediate Similarity	NPC473153
0.73	Intermediate Similarity	NPC190713
0.7297	Intermediate Similarity	NPC146786
0.7292	Intermediate Similarity	NPC307298
0.7292	Intermediate Similarity	NPC58271
0.7292	Intermediate Similarity	NPC472302
0.729	Intermediate Similarity	NPC12795
0.7283	Intermediate Similarity	NPC121984
0.7283	Intermediate Similarity	NPC6663
0.7283	Intermediate Similarity	NPC474085
0.7282	Intermediate Similarity	NPC273668
0.7273	Intermediate Similarity	NPC474882
0.7273	Intermediate Similarity	NPC38830
0.7264	Intermediate Similarity	NPC50124
0.7263	Intermediate Similarity	NPC472974
0.7263	Intermediate Similarity	NPC131813
0.7263	Intermediate Similarity	NPC203795
0.7255	Intermediate Similarity	NPC474012
0.7255	Intermediate Similarity	NPC474190
0.7255	Intermediate Similarity	NPC476299
0.7248	Intermediate Similarity	NPC241977
0.7248	Intermediate Similarity	NPC171126
0.7245	Intermediate Similarity	NPC470036
0.7245	Intermediate Similarity	NPC72845
0.7245	Intermediate Similarity	NPC329842
0.7245	Intermediate Similarity	NPC174167
0.7245	Intermediate Similarity	NPC45579
0.7238	Intermediate Similarity	NPC32006
0.7238	Intermediate Similarity	NPC477125
0.7238	Intermediate Similarity	NPC85529
0.7234	Intermediate Similarity	NPC470077
0.7234	Intermediate Similarity	NPC302360
0.7234	Intermediate Similarity	NPC306951
0.7228	Intermediate Similarity	NPC99726
0.7228	Intermediate Similarity	NPC141401
0.7222	Intermediate Similarity	NPC183603
0.7222	Intermediate Similarity	NPC266193
0.7222	Intermediate Similarity	NPC474315
0.7222	Intermediate Similarity	NPC54996
0.7222	Intermediate Similarity	NPC219809
0.7222	Intermediate Similarity	NPC470750
0.7222	Intermediate Similarity	NPC257666
0.7216	Intermediate Similarity	NPC472973
0.7216	Intermediate Similarity	NPC173042
0.7216	Intermediate Similarity	NPC50488
0.7216	Intermediate Similarity	NPC112454
0.7216	Intermediate Similarity	NPC474396
0.7212	Intermediate Similarity	NPC45897
0.7212	Intermediate Similarity	NPC131366
0.7212	Intermediate Similarity	NPC297617
0.7209	Intermediate Similarity	NPC476431
0.7207	Intermediate Similarity	NPC157380
0.7207	Intermediate Similarity	NPC185287
0.7204	Intermediate Similarity	NPC5985
0.7204	Intermediate Similarity	NPC256112
0.7204	Intermediate Similarity	NPC155521
0.7204	Intermediate Similarity	NPC470049
0.7204	Intermediate Similarity	NPC2524
0.72	Intermediate Similarity	NPC171395
0.72	Intermediate Similarity	NPC474909
0.72	Intermediate Similarity	NPC280725
0.72	Intermediate Similarity	NPC276110
0.7196	Intermediate Similarity	NPC300026
0.7188	Intermediate Similarity	NPC476079
0.7188	Intermediate Similarity	NPC103743
0.7188	Intermediate Similarity	NPC473097
0.7188	Intermediate Similarity	NPC477228
0.7188	Intermediate Similarity	NPC113370
0.7188	Intermediate Similarity	NPC30421
0.7188	Intermediate Similarity	NPC471792
0.7188	Intermediate Similarity	NPC181327
0.7184	Intermediate Similarity	NPC473160
0.7172	Intermediate Similarity	NPC7349
0.7172	Intermediate Similarity	NPC38232
0.7172	Intermediate Similarity	NPC271652
0.717	Intermediate Similarity	NPC475294
0.7158	Intermediate Similarity	NPC274448
0.7158	Intermediate Similarity	NPC307112
0.7158	Intermediate Similarity	NPC474013
0.7158	Intermediate Similarity	NPC32037
0.7158	Intermediate Similarity	NPC157257
0.7157	Intermediate Similarity	NPC108368
0.7157	Intermediate Similarity	NPC474440
0.7157	Intermediate Similarity	NPC57079
0.7157	Intermediate Similarity	NPC218107
0.7157	Intermediate Similarity	NPC316598

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 NPC212369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1468
0.2-0.3	3715
0.3-0.4	2465
0.4-0.5	929
0.5-0.6	196
0.6-0.7	179
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7556	Intermediate Similarity	NPD4695	Discontinued
0.7253	Intermediate Similarity	NPD4195	Approved
0.7216	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3573	Approved
0.7083	Intermediate Similarity	NPD4694	Approved
0.7083	Intermediate Similarity	NPD5280	Approved
0.7053	Intermediate Similarity	NPD4197	Approved
0.6979	Remote Similarity	NPD5329	Approved
0.6979	Remote Similarity	NPD1696	Phase 3
0.6957	Remote Similarity	NPD3617	Approved
0.6931	Remote Similarity	NPD7748	Approved
0.6907	Remote Similarity	NPD3618	Phase 1
0.6907	Remote Similarity	NPD4519	Discontinued
0.6907	Remote Similarity	NPD5690	Phase 2
0.6907	Remote Similarity	NPD4623	Approved
0.6907	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7115	Discovery
0.69	Remote Similarity	NPD5693	Phase 1
0.6882	Remote Similarity	NPD7645	Phase 2
0.6842	Remote Similarity	NPD4221	Approved
0.6842	Remote Similarity	NPD4223	Phase 3
0.6827	Remote Similarity	NPD4225	Approved
0.6827	Remote Similarity	NPD7638	Approved
0.681	Remote Similarity	NPD7503	Approved
0.6796	Remote Similarity	NPD5222	Approved
0.6796	Remote Similarity	NPD5221	Approved
0.6796	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5211	Phase 2
0.6762	Remote Similarity	NPD7640	Approved
0.6762	Remote Similarity	NPD5285	Approved
0.6762	Remote Similarity	NPD7639	Approved
0.6762	Remote Similarity	NPD4696	Approved
0.6762	Remote Similarity	NPD5286	Approved
0.6735	Remote Similarity	NPD5279	Phase 3
0.6733	Remote Similarity	NPD7515	Phase 2
0.6733	Remote Similarity	NPD6079	Approved
0.6731	Remote Similarity	NPD5173	Approved
0.6731	Remote Similarity	NPD4755	Approved
0.6731	Remote Similarity	NPD7902	Approved
0.67	Remote Similarity	NPD4753	Phase 2
0.67	Remote Similarity	NPD5328	Approved
0.6698	Remote Similarity	NPD5223	Approved
0.6697	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6636	Remote Similarity	NPD6881	Approved
0.6636	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5225	Approved
0.6636	Remote Similarity	NPD6899	Approved
0.6636	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD5224	Approved
0.6635	Remote Similarity	NPD4697	Phase 3
0.6634	Remote Similarity	NPD5692	Phase 3
0.6606	Remote Similarity	NPD5739	Approved
0.6606	Remote Similarity	NPD7128	Approved
0.6606	Remote Similarity	NPD6402	Approved
0.6606	Remote Similarity	NPD6675	Approved
0.6604	Remote Similarity	NPD4700	Approved
0.6577	Remote Similarity	NPD6013	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6577	Remote Similarity	NPD6012	Approved
0.6574	Remote Similarity	NPD5175	Approved
0.6574	Remote Similarity	NPD5174	Approved
0.6571	Remote Similarity	NPD6083	Phase 2
0.6571	Remote Similarity	NPD6084	Phase 2
0.6569	Remote Similarity	NPD6050	Approved
0.6569	Remote Similarity	NPD5694	Approved
0.6566	Remote Similarity	NPD4693	Phase 3
0.6566	Remote Similarity	NPD4690	Approved
0.6566	Remote Similarity	NPD4138	Approved
0.6566	Remote Similarity	NPD5205	Approved
0.6566	Remote Similarity	NPD4688	Approved
0.6566	Remote Similarity	NPD4689	Approved
0.6559	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5701	Approved
0.6538	Remote Similarity	NPD5210	Approved
0.6538	Remote Similarity	NPD4629	Approved
0.6538	Remote Similarity	NPD5695	Phase 3
0.6535	Remote Similarity	NPD6904	Approved
0.6535	Remote Similarity	NPD6673	Approved
0.6535	Remote Similarity	NPD6080	Approved
0.6531	Remote Similarity	NPD3666	Approved
0.6531	Remote Similarity	NPD4786	Approved
0.6531	Remote Similarity	NPD3133	Approved
0.6531	Remote Similarity	NPD3665	Phase 1
0.6522	Remote Similarity	NPD4785	Approved
0.6522	Remote Similarity	NPD4784	Approved
0.6518	Remote Similarity	NPD7290	Approved
0.6518	Remote Similarity	NPD6883	Approved
0.6518	Remote Similarity	NPD7102	Approved
0.6509	Remote Similarity	NPD5696	Approved
0.6505	Remote Similarity	NPD5133	Approved
0.6495	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7320	Approved
0.6484	Remote Similarity	NPD4243	Approved
0.6465	Remote Similarity	NPD1694	Approved
0.646	Remote Similarity	NPD6869	Approved
0.646	Remote Similarity	NPD6649	Approved
0.646	Remote Similarity	NPD6650	Approved
0.646	Remote Similarity	NPD6847	Approved
0.646	Remote Similarity	NPD6617	Approved
0.646	Remote Similarity	NPD8130	Phase 1
0.6458	Remote Similarity	NPD7525	Registered
0.6452	Remote Similarity	NPD7339	Approved
0.6452	Remote Similarity	NPD6942	Approved
0.6452	Remote Similarity	NPD8264	Approved
0.6442	Remote Similarity	NPD7900	Approved
0.6442	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5737	Approved
0.6436	Remote Similarity	NPD6672	Approved
0.6429	Remote Similarity	NPD6373	Approved
0.6429	Remote Similarity	NPD6372	Approved
0.6422	Remote Similarity	NPD4754	Approved
0.6408	Remote Similarity	NPD5284	Approved
0.6408	Remote Similarity	NPD5281	Approved
0.6404	Remote Similarity	NPD6882	Approved
0.6404	Remote Similarity	NPD8297	Approved
0.64	Remote Similarity	NPD6098	Approved
0.6373	Remote Similarity	NPD6051	Approved
0.6355	Remote Similarity	NPD5290	Discontinued
0.6346	Remote Similarity	NPD6399	Phase 3
0.6344	Remote Similarity	NPD4058	Approved
0.6344	Remote Similarity	NPD6926	Approved
0.6344	Remote Similarity	NPD6924	Approved
0.6339	Remote Similarity	NPD5128	Approved
0.6339	Remote Similarity	NPD4730	Approved
0.6339	Remote Similarity	NPD4729	Approved
0.6337	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4096	Approved
0.6311	Remote Similarity	NPD5207	Approved
0.6306	Remote Similarity	NPD4768	Approved
0.6306	Remote Similarity	NPD4767	Approved
0.6296	Remote Similarity	NPD6648	Approved
0.6289	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6001	Approved
0.6277	Remote Similarity	NPD4190	Phase 3
0.6277	Remote Similarity	NPD5275	Approved
0.6275	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4518	Approved
0.6275	Remote Similarity	NPD5208	Approved
0.6263	Remote Similarity	NPD6695	Phase 3
0.6239	Remote Similarity	NPD6274	Approved
0.6239	Remote Similarity	NPD4159	Approved
0.6238	Remote Similarity	NPD6684	Approved
0.6238	Remote Similarity	NPD7521	Approved
0.6238	Remote Similarity	NPD7334	Approved
0.6238	Remote Similarity	NPD7146	Approved
0.6238	Remote Similarity	NPD6409	Approved
0.6238	Remote Similarity	NPD5330	Approved
0.6228	Remote Similarity	NPD5249	Phase 3
0.6228	Remote Similarity	NPD5169	Approved
0.6228	Remote Similarity	NPD5135	Approved
0.6228	Remote Similarity	NPD5251	Approved
0.6228	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4634	Approved
0.6228	Remote Similarity	NPD5247	Approved
0.6228	Remote Similarity	NPD5248	Approved
0.6228	Remote Similarity	NPD5250	Approved
0.6226	Remote Similarity	NPD5654	Approved
0.6226	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6933	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.62	Remote Similarity	NPD3668	Phase 3
0.62	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4691	Approved
0.6195	Remote Similarity	NPD5168	Approved
0.6186	Remote Similarity	NPD6317	Approved
0.6182	Remote Similarity	NPD7632	Discontinued
0.6182	Remote Similarity	NPD5091	Approved
0.6174	Remote Similarity	NPD5216	Approved
0.6174	Remote Similarity	NPD5127	Approved
0.6174	Remote Similarity	NPD5215	Approved
0.6174	Remote Similarity	NPD5217	Approved
0.6146	Remote Similarity	NPD4756	Discovery
0.614	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7327	Approved
0.6134	Remote Similarity	NPD6314	Approved
0.6134	Remote Similarity	NPD6313	Approved
0.6134	Remote Similarity	NPD6335	Approved
0.6134	Remote Similarity	NPD7328	Approved
0.6122	Remote Similarity	NPD7509	Discontinued
0.6122	Remote Similarity	NPD6930	Phase 2
0.6122	Remote Similarity	NPD6931	Approved
0.6117	Remote Similarity	NPD6903	Approved
0.6116	Remote Similarity	NPD8033	Approved
0.6111	Remote Similarity	NPD5959	Approved
0.6102	Remote Similarity	NPD6868	Approved
0.61	Remote Similarity	NPD4788	Approved
0.6091	Remote Similarity	NPD5344	Discontinued
0.6087	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4137	Phase 3
0.6083	Remote Similarity	NPD7101	Approved
0.6083	Remote Similarity	NPD7100	Approved
0.6083	Remote Similarity	NPD7516	Approved
0.6082	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6009	Approved
0.604	Remote Similarity	NPD6400	Clinical (unspecified phase)

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