NPASS Compound

Structure

CID56091 OpenBabel06191715392D 30 34 0 0 1 0 0 0 0 0999 V2000 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 5.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6369 3.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 5.5388 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 2.4400 5.5170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0491 2.7298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8412 4.7080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0491 4.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 12 2 0 0 0 0 4 15 1 0 0 0 0 5 13 2 0 0 0 0 5 16 1 0 0 0 0 6 12 1 0 0 0 0 6 17 2 0 0 0 0 7 13 1 0 0 0 0 7 18 2 0 0 0 0 8 14 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 9 29 1 0 0 0 0 10 28 1 0 0 0 0 10 30 1 0 0 0 0 11 1 1 1 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 13 19 1 0 0 0 0 14 19 1 1 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 21 1 0 0 0 0 18 28 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 23 1 6 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.15
Volume:	400.789
LogP:	3.34
LogD:	3.437
LogS:	-4.836
# Rotatable Bonds:	5
TPSA:	84.84
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	3.992
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.891
MDCK Permeability:	4.186553996987641e-05
Pgp-inhibitor:	0.077
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	96.40679931640625%
Volume Distribution (VD):	2.03
Pgp-substrate:	2.269899368286133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.161
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.83
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.494
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.848
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.783

ADMET: Excretion

Clearance (CL):	12.445
Half-life (T1/2):	0.206

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.556
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.337
Skin Sensitization:	0.698
Carcinogencity:	0.91
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.255

Download Data

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

Natural Product: NPC56091

Natural Product ID:	NPC56091
*Common Name:**	(2R,3R,4S)-4-[Bis(7-Methoxy-1,3-Benzodioxol-5-Yl)Methyl]-3-Methyloxolan-2-Ol
IUPAC Name:	(2R,3R,4S)-4-[bis(7-methoxy-1,3-benzodioxol-5-yl)methyl]-3-methyloxolan-2-ol
Synonyms:
Standard InCHIKey:	SNBUNJUZIKRKCA-MHLYXQECSA-N
Standard InCHI:	InChI=1S/C22H24O8/c1-11-14(8-26-22(11)23)19(12-4-15(24-2)20-17(6-12)27-9-29-20)13-5-16(25-3)21-18(7-13)28-10-30-21/h4-7,11,14,19,22-23H,8-10H2,1-3H3/t11-,14-,22-/m1/s1
SMILES:	C[C@@H]1[C@@H](CO[C@H]1O)C(c1cc(c2c(c1)OCO2)OC)c1cc(c2c(c1)OCO2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496846
PubChem CID:	11704381
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	bark	n.a.	PMID[11101460]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16309318]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16724842]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13728	Metanarthecium luteoviride	Species	Nartheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22405	Litsea monopetala	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19590	Daedaleopsis tricolor	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27184	Bonellia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27953	Eugenia formosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27401	Aniba riparia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17271	Aegialitis annulata	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27135	Tubularia larynx	Species	Tubulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27362	Hypericum elodes	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28066	Aloe speciosa	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28133	Geigeria filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27439	Letharia vulpina	Species	Parmeliaceae	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	3
Others	6

Activity Type	# Activity
Cell Line	2
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	138000.0	nM	PMID[533249]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	140000.0	nM	PMID[533249]
NPT27	Others	Unspecified		IC50	=	142000.0	nM	PMID[533249]
NPT2	Others	Unspecified		Activity	=	99.0	%	PMID[533249]
NPT2	Others	Unspecified		Activity	=	104.0	%	PMID[533249]
NPT2	Others	Unspecified		Activity	=	107.0	%	PMID[533249]
NPT2	Others	Unspecified		Activity	=	93.0	%	PMID[533249]
NPT2	Others	Unspecified		Activity	=	90.0	%	PMID[533249]
NPT2	Others	Unspecified		Activity	=	71.0	%	PMID[533249]

☑ 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 NPC56091 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	381
0.1-0.2	1414
0.2-0.3	3764
0.3-0.4	10126
0.4-0.5	9030
0.5-0.6	5389
0.6-0.7	8875
0.7-0.8	2774
0.8-0.85	603
0.85-0.9	284
0.9-0.95	47
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC46591
0.9848	High Similarity	NPC283949
0.9701	High Similarity	NPC226547
0.9699	High Similarity	NPC185908
0.9697	High Similarity	NPC150534
0.9562	High Similarity	NPC166884
0.9562	High Similarity	NPC477701
0.9562	High Similarity	NPC141569
0.9549	High Similarity	NPC236522
0.9549	High Similarity	NPC148893
0.9549	High Similarity	NPC49235
0.9549	High Similarity	NPC25333
0.9489	High Similarity	NPC185071
0.9489	High Similarity	NPC12728
0.9474	High Similarity	NPC31530
0.9416	High Similarity	NPC287124
0.9403	High Similarity	NPC189474
0.9398	High Similarity	NPC196937
0.9348	High Similarity	NPC298317
0.9348	High Similarity	NPC255566
0.9338	High Similarity	NPC113550
0.9328	High Similarity	NPC47181
0.9323	High Similarity	NPC72046
0.9323	High Similarity	NPC65183
0.9323	High Similarity	NPC261812
0.927	High Similarity	NPC177868
0.9265	High Similarity	NPC469981
0.9259	High Similarity	NPC18576
0.9254	High Similarity	NPC266848
0.9254	High Similarity	NPC136750
0.9248	High Similarity	NPC192255
0.9203	High Similarity	NPC471908
0.9203	High Similarity	NPC312199
0.9191	High Similarity	NPC11453
0.9191	High Similarity	NPC121651
0.9173	High Similarity	NPC134764
0.9173	High Similarity	NPC171550
0.9155	High Similarity	NPC248132
0.9155	High Similarity	NPC130449
0.9149	High Similarity	NPC212890
0.9143	High Similarity	NPC472712
0.9143	High Similarity	NPC472713
0.9143	High Similarity	NPC118385
0.9143	High Similarity	NPC187774
0.9143	High Similarity	NPC473046
0.9124	High Similarity	NPC474039
0.9104	High Similarity	NPC82111
0.9104	High Similarity	NPC227160
0.9097	High Similarity	NPC164082
0.9091	High Similarity	NPC95392
0.9091	High Similarity	NPC51328
0.9091	High Similarity	NPC35877
0.9091	High Similarity	NPC55715
0.9091	High Similarity	NPC286235
0.9091	High Similarity	NPC55158
0.9078	High Similarity	NPC475868
0.9078	High Similarity	NPC477702
0.9071	High Similarity	NPC474808
0.9058	High Similarity	NPC88640
0.9058	High Similarity	NPC9068
0.9058	High Similarity	NPC193666
0.9058	High Similarity	NPC123526
0.9058	High Similarity	NPC156376
0.9037	High Similarity	NPC219671
0.9037	High Similarity	NPC259742
0.9037	High Similarity	NPC147616
0.9037	High Similarity	NPC104077
0.903	High Similarity	NPC233224
0.903	High Similarity	NPC271208
0.9023	High Similarity	NPC54321
0.9023	High Similarity	NPC328682
0.9023	High Similarity	NPC281864
0.9007	High Similarity	NPC172171
0.9007	High Similarity	NPC239254
0.9	High Similarity	NPC311057
0.9	High Similarity	NPC474295
0.9	High Similarity	NPC5262
0.9	High Similarity	NPC246947
0.9	High Similarity	NPC472714
0.8986	High Similarity	NPC101807
0.8978	High Similarity	NPC24490
0.8978	High Similarity	NPC141765
0.8978	High Similarity	NPC165155
0.8978	High Similarity	NPC34103
0.8971	High Similarity	NPC1474
0.8958	High Similarity	NPC240521
0.8958	High Similarity	NPC477698
0.8951	High Similarity	NPC39657
0.8947	High Similarity	NPC473092
0.8947	High Similarity	NPC158737
0.8947	High Similarity	NPC473093
0.8947	High Similarity	NPC8050
0.8944	High Similarity	NPC180953
0.8936	High Similarity	NPC477898
0.8936	High Similarity	NPC324962
0.8913	High Similarity	NPC25695
0.8913	High Similarity	NPC143895
0.8913	High Similarity	NPC197166
0.8913	High Similarity	NPC172818
0.8905	High Similarity	NPC326095
0.8905	High Similarity	NPC244983
0.8897	High Similarity	NPC473989
0.8897	High Similarity	NPC238140
0.8897	High Similarity	NPC100223
0.8897	High Similarity	NPC129687
0.8897	High Similarity	NPC171928
0.8897	High Similarity	NPC33611
0.8897	High Similarity	NPC16830
0.8897	High Similarity	NPC158526
0.8897	High Similarity	NPC7744
0.8889	High Similarity	NPC270751
0.8889	High Similarity	NPC63574
0.8881	High Similarity	NPC226862
0.8881	High Similarity	NPC165128
0.8881	High Similarity	NPC222127
0.8881	High Similarity	NPC158471
0.8881	High Similarity	NPC57119
0.8881	High Similarity	NPC82862
0.8873	High Similarity	NPC84181
0.8873	High Similarity	NPC92693
0.8873	High Similarity	NPC179521
0.8873	High Similarity	NPC218841
0.8872	High Similarity	NPC40352
0.8872	High Similarity	NPC213711
0.8865	High Similarity	NPC230538
0.8865	High Similarity	NPC103637
0.8865	High Similarity	NPC36531
0.8865	High Similarity	NPC229172
0.8857	High Similarity	NPC216434
0.8857	High Similarity	NPC103448
0.8841	High Similarity	NPC101624
0.8841	High Similarity	NPC126409
0.8841	High Similarity	NPC142547
0.8841	High Similarity	NPC135777
0.8841	High Similarity	NPC184938
0.8841	High Similarity	NPC99572
0.8841	High Similarity	NPC474139
0.8841	High Similarity	NPC174191
0.8832	High Similarity	NPC58585
0.8832	High Similarity	NPC169973
0.8832	High Similarity	NPC69513
0.8832	High Similarity	NPC215833
0.8819	High Similarity	NPC116019
0.8811	High Similarity	NPC22150
0.8811	High Similarity	NPC205316
0.8811	High Similarity	NPC279298
0.8811	High Similarity	NPC38041
0.8811	High Similarity	NPC469586
0.8803	High Similarity	NPC265154
0.8794	High Similarity	NPC472711
0.8786	High Similarity	NPC290714
0.8786	High Similarity	NPC201404
0.8786	High Similarity	NPC6369
0.8786	High Similarity	NPC53722
0.8786	High Similarity	NPC30951
0.8777	High Similarity	NPC32189
0.8776	High Similarity	NPC56184
0.8768	High Similarity	NPC287745
0.8768	High Similarity	NPC48863
0.8768	High Similarity	NPC107478
0.8768	High Similarity	NPC13745
0.8768	High Similarity	NPC251981
0.8767	High Similarity	NPC472710
0.8767	High Similarity	NPC472709
0.8759	High Similarity	NPC204215
0.8759	High Similarity	NPC316676
0.8759	High Similarity	NPC71726
0.8759	High Similarity	NPC175067
0.8759	High Similarity	NPC325720
0.875	High Similarity	NPC154971
0.875	High Similarity	NPC193779
0.875	High Similarity	NPC205796
0.875	High Similarity	NPC252286
0.875	High Similarity	NPC276753
0.875	High Similarity	NPC112861
0.8741	High Similarity	NPC191158
0.8741	High Similarity	NPC177644
0.8741	High Similarity	NPC473045
0.8741	High Similarity	NPC25292
0.8732	High Similarity	NPC472562
0.8732	High Similarity	NPC80326
0.8732	High Similarity	NPC151423
0.8732	High Similarity	NPC302506
0.8732	High Similarity	NPC189115
0.8732	High Similarity	NPC40237
0.8731	High Similarity	NPC50683
0.8731	High Similarity	NPC88297
0.8731	High Similarity	NPC473960
0.8731	High Similarity	NPC112571
0.8731	High Similarity	NPC9891
0.8731	High Similarity	NPC186845
0.8731	High Similarity	NPC206882
0.8731	High Similarity	NPC285725
0.8723	High Similarity	NPC284464
0.8699	High Similarity	NPC174512
0.8699	High Similarity	NPC474965
0.8699	High Similarity	NPC477695
0.8699	High Similarity	NPC668
0.8699	High Similarity	NPC293757
0.8696	High Similarity	NPC112237

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 NPC56091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	863
0.2-0.3	1859
0.3-0.4	2878
0.4-0.5	1717
0.5-0.6	1009
0.6-0.7	458
0.7-0.8	64
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8543	High Similarity	NPD4967	Phase 2
0.8543	High Similarity	NPD4966	Approved
0.8543	High Similarity	NPD4965	Approved
0.8406	Intermediate Similarity	NPD3027	Phase 3
0.8358	Intermediate Similarity	NPD3705	Approved
0.8344	Intermediate Similarity	NPD37	Approved
0.8312	Intermediate Similarity	NPD6234	Discontinued
0.8176	Intermediate Similarity	NPD7228	Approved
0.8089	Intermediate Similarity	NPD7199	Phase 2
0.7975	Intermediate Similarity	NPD7240	Approved
0.7875	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1613	Approved
0.7842	Intermediate Similarity	NPD2983	Phase 2
0.7842	Intermediate Similarity	NPD2982	Phase 2
0.782	Intermediate Similarity	NPD5283	Phase 1
0.7785	Intermediate Similarity	NPD6674	Discontinued
0.777	Intermediate Similarity	NPD2981	Phase 2
0.7746	Intermediate Similarity	NPD3018	Phase 2
0.7746	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1357	Approved
0.7697	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.7613	Intermediate Similarity	NPD1653	Approved
0.7569	Intermediate Similarity	NPD4908	Phase 1
0.7562	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7266	Discontinued
0.7466	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1610	Phase 2
0.7447	Intermediate Similarity	NPD1091	Approved
0.7438	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7074	Phase 3
0.7412	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7054	Approved
0.7342	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4005	Discontinued
0.7333	Intermediate Similarity	NPD7680	Approved
0.7321	Intermediate Similarity	NPD7472	Approved
0.731	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1375	Discontinued
0.7303	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5058	Phase 3
0.726	Intermediate Similarity	NPD2861	Phase 2
0.7248	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3620	Phase 2
0.723	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4749	Approved
0.7208	Intermediate Similarity	NPD4237	Approved
0.7208	Intermediate Similarity	NPD4236	Phase 3
0.7194	Intermediate Similarity	NPD7157	Approved
0.7193	Intermediate Similarity	NPD7808	Phase 3
0.719	Intermediate Similarity	NPD3540	Phase 1
0.7179	Intermediate Similarity	NPD7124	Phase 2
0.7176	Intermediate Similarity	NPD6797	Phase 2
0.7171	Intermediate Similarity	NPD4108	Discontinued
0.7163	Intermediate Similarity	NPD1548	Phase 1
0.716	Intermediate Similarity	NPD2978	Approved
0.716	Intermediate Similarity	NPD2977	Approved
0.7153	Intermediate Similarity	NPD228	Approved
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3539	Phase 1
0.7117	Intermediate Similarity	NPD3817	Phase 2
0.7115	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6111	Discontinued
0.7101	Intermediate Similarity	NPD7843	Approved
0.7099	Intermediate Similarity	NPD1934	Approved
0.7099	Intermediate Similarity	NPD3383	Approved
0.7099	Intermediate Similarity	NPD3382	Approved
0.7099	Intermediate Similarity	NPD3384	Approved
0.7093	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7028	Phase 2
0.7081	Intermediate Similarity	NPD4678	Approved
0.7081	Intermediate Similarity	NPD4675	Approved
0.7073	Intermediate Similarity	NPD3882	Suspended
0.7073	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5126	Approved
0.7063	Intermediate Similarity	NPD5125	Phase 3
0.7059	Intermediate Similarity	NPD2684	Approved
0.7055	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4110	Phase 3
0.7051	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3892	Phase 2
0.7048	Intermediate Similarity	NPD5494	Approved
0.7047	Intermediate Similarity	NPD4625	Phase 3
0.7035	Intermediate Similarity	NPD7685	Pre-registration
0.7025	Intermediate Similarity	NPD4357	Discontinued
0.702	Intermediate Similarity	NPD4060	Phase 1
0.7007	Intermediate Similarity	NPD3021	Approved
0.7007	Intermediate Similarity	NPD3022	Approved
0.6989	Remote Similarity	NPD6842	Approved
0.6989	Remote Similarity	NPD6841	Approved
0.6989	Remote Similarity	NPD6843	Phase 3
0.6987	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6166	Phase 2
0.6982	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5735	Approved
0.6972	Remote Similarity	NPD5536	Phase 2
0.6964	Remote Similarity	NPD6232	Discontinued
0.6959	Remote Similarity	NPD5844	Phase 1
0.6951	Remote Similarity	NPD2801	Approved
0.6951	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8455	Phase 2
0.6948	Remote Similarity	NPD5588	Approved
0.6943	Remote Similarity	NPD6331	Phase 2
0.6941	Remote Similarity	NPD7473	Discontinued
0.6937	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2238	Phase 2
0.6903	Remote Similarity	NPD2161	Phase 2
0.6899	Remote Similarity	NPD2219	Phase 1
0.6887	Remote Similarity	NPD5110	Phase 2
0.6887	Remote Similarity	NPD5109	Approved
0.6887	Remote Similarity	NPD5111	Phase 2
0.6883	Remote Similarity	NPD4536	Approved
0.6883	Remote Similarity	NPD4538	Approved
0.6883	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3060	Approved
0.6879	Remote Similarity	NPD5177	Phase 3
0.6871	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3657	Discovery
0.6863	Remote Similarity	NPD6355	Discontinued
0.686	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5762	Approved
0.6859	Remote Similarity	NPD5763	Approved
0.6855	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4055	Discovery
0.6824	Remote Similarity	NPD8651	Approved
0.6821	Remote Similarity	NPD7095	Approved
0.6805	Remote Similarity	NPD8127	Discontinued
0.6803	Remote Similarity	NPD1608	Approved
0.68	Remote Similarity	NPD7549	Discontinued
0.6798	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1558	Phase 1
0.6797	Remote Similarity	NPD4140	Approved
0.6778	Remote Similarity	NPD7296	Approved
0.6774	Remote Similarity	NPD7097	Phase 1
0.6772	Remote Similarity	NPD1652	Phase 2
0.677	Remote Similarity	NPD4123	Phase 3
0.6768	Remote Similarity	NPD4380	Phase 2
0.6765	Remote Similarity	NPD7229	Phase 3
0.6765	Remote Similarity	NPD3787	Discontinued
0.6763	Remote Similarity	NPD4750	Phase 3
0.6757	Remote Similarity	NPD3685	Discontinued
0.6755	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD230	Phase 1
0.6753	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5124	Phase 1
0.6748	Remote Similarity	NPD4210	Discontinued
0.6747	Remote Similarity	NPD1465	Phase 2
0.6747	Remote Similarity	NPD7819	Suspended
0.6735	Remote Similarity	NPD422	Phase 1
0.6732	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5960	Phase 3
0.673	Remote Similarity	NPD4628	Phase 3
0.673	Remote Similarity	NPD7466	Approved
0.6728	Remote Similarity	NPD7526	Approved
0.6728	Remote Similarity	NPD52	Approved
0.6728	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5604	Discontinued
0.6725	Remote Similarity	NPD3926	Phase 2
0.6725	Remote Similarity	NPD5242	Approved
0.6712	Remote Similarity	NPD5846	Approved
0.6712	Remote Similarity	NPD6516	Phase 2
0.671	Remote Similarity	NPD6653	Approved
0.6709	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1511	Approved
0.6707	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2563	Approved
0.6707	Remote Similarity	NPD2560	Approved
0.6688	Remote Similarity	NPD6099	Approved
0.6688	Remote Similarity	NPD6100	Approved
0.6688	Remote Similarity	NPD2438	Suspended
0.6687	Remote Similarity	NPD2677	Approved
0.6687	Remote Similarity	NPD6190	Approved
0.6686	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4162	Approved
0.6667	Remote Similarity	NPD1242	Phase 1
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD6895	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD6896	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5773	Approved
0.6647	Remote Similarity	NPD5772	Approved
0.6646	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6005	Phase 3
0.6646	Remote Similarity	NPD6004	Phase 3
0.6646	Remote Similarity	NPD6006	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