NPASS Compound

Structure

CID156393 OpenBabel06191715522D 28 30 0 0 1 0 0 0 0 0999 V2000 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8690 -2.0000 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 -0.8660 -2.5000 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 -2.5981 -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 -5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 2 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.0000 -1.0000 0.0000 C 0 0 2 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 -5.5902 -0.2399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5902 -3.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 8 1 0 0 0 0 2 9 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 27 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 21 1 0 0 0 0 8 11 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 3 1 1 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 7 1 6 0 0 0 13 17 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 15 22 1 6 0 0 0 16 23 2 0 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 19 1 0 0 0 0 18 25 1 6 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 27 1 6 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.18
Volume:	388.583
LogP:	0.514
LogD:	0.455
LogS:	-1.981
# Rotatable Bonds:	5
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	4.348
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.213
MDCK Permeability:	1.3602398212242406e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.753
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.442

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	69.9372329711914%
Volume Distribution (VD):	1.434
Pgp-substrate:	20.604373931884766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.276
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.105
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	1.645
Half-life (T1/2):	0.559

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.228
Drug-inuced Liver Injury (DILI):	0.518
AMES Toxicity:	0.451
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.106
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC156393

Natural Product ID:	NPC156393
*Common Name:**	(2S,3S)-3-Hydroxy-2,5,7-Trimethyl-6-[2-[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyethyl]-2,3-Dihydroinden-1-One
IUPAC Name:	(2S,3S)-3-hydroxy-2,5,7-trimethyl-6-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-2,3-dihydroinden-1-one
Synonyms:
Standard InCHIKey:	VKDMMOFAMUXTQZ-VTNBQNSRSA-N
Standard InCHI:	InChI=1S/C20H28O8/c1-8-6-12-14(16(23)10(3)15(12)22)9(2)11(8)4-5-27-20-19(26)18(25)17(24)13(7-21)28-20/h6,10,13,15,17-22,24-26H,4-5,7H2,1-3H3/t10-,13+,15-,17+,18-,19+,20+/m0/s1
SMILES:	OC[C@H]1O[C@@H](OCCc2c(C)cc3c(c2C)C(=O)[C@H]([C@@H]3O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1892637
PubChem CID:	44201982
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28006909]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1776	Attalea excelsa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12516	Phalaris canariensis	Species	Poaceae	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	1
Potency	7

Activity Type	# Activity
Cell Line	1
Individual Protein	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[469513]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[469513]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[469513]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[469513]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	5173.5	nM	PMID[469513]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	2909.3	nM	PMID[469513]
NPT2615	Cell Line	HEK-293T	Homo sapiens	Activity	=	100.0	%	PMID[469514]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[469513]

☑ 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 NPC156393 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	285
0.1-0.2	1065
0.2-0.3	2372
0.3-0.4	5406
0.4-0.5	11236
0.5-0.6	12551
0.6-0.7	8721
0.7-0.8	1034
0.8-0.85	19
0.85-0.9	2
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.8615	High Similarity	NPC133302
0.8609	High Similarity	NPC208676
0.8609	High Similarity	NPC130489
0.8345	Intermediate Similarity	NPC159811
0.8333	Intermediate Similarity	NPC257847
0.8267	Intermediate Similarity	NPC469456
0.8209	Intermediate Similarity	NPC18785
0.8129	Intermediate Similarity	NPC27712
0.8039	Intermediate Similarity	NPC205172
0.8039	Intermediate Similarity	NPC209393
0.8	Intermediate Similarity	NPC82712
0.8	Intermediate Similarity	NPC476173
0.7987	Intermediate Similarity	NPC3449
0.7945	Intermediate Similarity	NPC242355
0.7935	Intermediate Similarity	NPC283480
0.7935	Intermediate Similarity	NPC148323
0.7933	Intermediate Similarity	NPC120536
0.7902	Intermediate Similarity	NPC28836
0.7902	Intermediate Similarity	NPC470143
0.7902	Intermediate Similarity	NPC322503
0.7902	Intermediate Similarity	NPC311492
0.7899	Intermediate Similarity	NPC317163
0.7887	Intermediate Similarity	NPC233692
0.7887	Intermediate Similarity	NPC239358
0.7885	Intermediate Similarity	NPC208651
0.7885	Intermediate Similarity	NPC206641
0.7872	Intermediate Similarity	NPC262819
0.7871	Intermediate Similarity	NPC476784
0.7871	Intermediate Similarity	NPC192219
0.7871	Intermediate Similarity	NPC82190
0.7871	Intermediate Similarity	NPC174599
0.7843	Intermediate Similarity	NPC158546
0.7843	Intermediate Similarity	NPC469477
0.7843	Intermediate Similarity	NPC471135
0.7843	Intermediate Similarity	NPC133430
0.7843	Intermediate Similarity	NPC289021
0.7834	Intermediate Similarity	NPC53139
0.7832	Intermediate Similarity	NPC472248
0.7823	Intermediate Similarity	NPC77493
0.7808	Intermediate Similarity	NPC473301
0.7806	Intermediate Similarity	NPC469417
0.78	Intermediate Similarity	NPC170668
0.78	Intermediate Similarity	NPC312393
0.78	Intermediate Similarity	NPC469513
0.7799	Intermediate Similarity	NPC477491
0.7794	Intermediate Similarity	NPC233923
0.7794	Intermediate Similarity	NPC146673
0.7778	Intermediate Similarity	NPC38420
0.7778	Intermediate Similarity	NPC136608
0.777	Intermediate Similarity	NPC244454
0.7762	Intermediate Similarity	NPC233860
0.7756	Intermediate Similarity	NPC319404
0.7755	Intermediate Similarity	NPC476643
0.7748	Intermediate Similarity	NPC205389
0.7748	Intermediate Similarity	NPC170055
0.7742	Intermediate Similarity	NPC475638
0.7742	Intermediate Similarity	NPC290683
0.7742	Intermediate Similarity	NPC475548
0.774	Intermediate Similarity	NPC27721
0.7727	Intermediate Similarity	NPC472657
0.7727	Intermediate Similarity	NPC472658
0.7724	Intermediate Similarity	NPC200154
0.7721	Intermediate Similarity	NPC238582
0.7718	Intermediate Similarity	NPC45307
0.7712	Intermediate Similarity	NPC96599
0.7703	Intermediate Similarity	NPC473497
0.7703	Intermediate Similarity	NPC474303
0.7703	Intermediate Similarity	NPC475413
0.7702	Intermediate Similarity	NPC40138
0.7698	Intermediate Similarity	NPC138798
0.7697	Intermediate Similarity	NPC285122
0.7692	Intermediate Similarity	NPC318447
0.7692	Intermediate Similarity	NPC322048
0.7688	Intermediate Similarity	NPC325732
0.7688	Intermediate Similarity	NPC278329
0.7688	Intermediate Similarity	NPC146837
0.7688	Intermediate Similarity	NPC97637
0.7688	Intermediate Similarity	NPC187934
0.7688	Intermediate Similarity	NPC324769
0.7687	Intermediate Similarity	NPC475195
0.7682	Intermediate Similarity	NPC477737
0.7682	Intermediate Similarity	NPC48130
0.7682	Intermediate Similarity	NPC218866
0.7682	Intermediate Similarity	NPC84568
0.7682	Intermediate Similarity	NPC300684
0.7677	Intermediate Similarity	NPC5115
0.7677	Intermediate Similarity	NPC478235
0.7671	Intermediate Similarity	NPC202729
0.7662	Intermediate Similarity	NPC117346
0.7662	Intermediate Similarity	NPC240592
0.766	Intermediate Similarity	NPC472706
0.7655	Intermediate Similarity	NPC153617
0.7654	Intermediate Similarity	NPC477488
0.7647	Intermediate Similarity	NPC222102
0.7647	Intermediate Similarity	NPC477101
0.7647	Intermediate Similarity	NPC469448
0.7647	Intermediate Similarity	NPC477099
0.7647	Intermediate Similarity	NPC303429
0.7647	Intermediate Similarity	NPC477097
0.7647	Intermediate Similarity	NPC232583
0.7647	Intermediate Similarity	NPC25484
0.7643	Intermediate Similarity	NPC469399
0.7636	Intermediate Similarity	NPC195972
0.7635	Intermediate Similarity	NPC474250
0.7632	Intermediate Similarity	NPC327031
0.7628	Intermediate Similarity	NPC229354
0.7628	Intermediate Similarity	NPC154675
0.7628	Intermediate Similarity	NPC326235
0.7628	Intermediate Similarity	NPC323001
0.7626	Intermediate Similarity	NPC223351
0.7625	Intermediate Similarity	NPC477627
0.7625	Intermediate Similarity	NPC471134
0.7616	Intermediate Similarity	NPC194938
0.7616	Intermediate Similarity	NPC296659
0.7616	Intermediate Similarity	NPC202391
0.7616	Intermediate Similarity	NPC134131
0.7616	Intermediate Similarity	NPC25043
0.7613	Intermediate Similarity	NPC477100
0.7613	Intermediate Similarity	NPC477098
0.7613	Intermediate Similarity	NPC146310
0.7613	Intermediate Similarity	NPC475407
0.7612	Intermediate Similarity	NPC274839
0.761	Intermediate Similarity	NPC477188
0.761	Intermediate Similarity	NPC43304
0.761	Intermediate Similarity	NPC314795
0.761	Intermediate Similarity	NPC477190
0.7606	Intermediate Similarity	NPC472707
0.7597	Intermediate Similarity	NPC161955
0.7597	Intermediate Similarity	NPC469415
0.7597	Intermediate Similarity	NPC478234
0.7597	Intermediate Similarity	NPC478236
0.7595	Intermediate Similarity	NPC323356
0.7595	Intermediate Similarity	NPC471138
0.7595	Intermediate Similarity	NPC10945
0.7595	Intermediate Similarity	NPC475378
0.7595	Intermediate Similarity	NPC326328
0.7595	Intermediate Similarity	NPC309991
0.7593	Intermediate Similarity	NPC478020
0.7593	Intermediate Similarity	NPC478026
0.7593	Intermediate Similarity	NPC178281
0.7593	Intermediate Similarity	NPC478022
0.758	Intermediate Similarity	NPC470331
0.7578	Intermediate Similarity	NPC473557
0.7578	Intermediate Similarity	NPC212099
0.7578	Intermediate Similarity	NPC475567
0.7578	Intermediate Similarity	NPC216752
0.7578	Intermediate Similarity	NPC101116
0.7578	Intermediate Similarity	NPC473468
0.7571	Intermediate Similarity	NPC228739
0.7569	Intermediate Similarity	NPC72915
0.7566	Intermediate Similarity	NPC478263
0.7564	Intermediate Similarity	NPC251139
0.7562	Intermediate Similarity	NPC66193
0.7562	Intermediate Similarity	NPC470358
0.7552	Intermediate Similarity	NPC301857
0.755	Intermediate Similarity	NPC186296
0.7547	Intermediate Similarity	NPC29552
0.7547	Intermediate Similarity	NPC329997
0.7538	Intermediate Similarity	NPC185763
0.7538	Intermediate Similarity	NPC83409
0.7535	Intermediate Similarity	NPC114096
0.7533	Intermediate Similarity	NPC159387
0.7533	Intermediate Similarity	NPC192658
0.7533	Intermediate Similarity	NPC154262
0.7533	Intermediate Similarity	NPC137501
0.7533	Intermediate Similarity	NPC7518
0.7532	Intermediate Similarity	NPC474501
0.7532	Intermediate Similarity	NPC189631
0.7531	Intermediate Similarity	NPC475175
0.7531	Intermediate Similarity	NPC475198
0.7531	Intermediate Similarity	NPC475531
0.7516	Intermediate Similarity	NPC11410
0.7516	Intermediate Similarity	NPC132652
0.7516	Intermediate Similarity	NPC473147
0.7516	Intermediate Similarity	NPC471493
0.75	Intermediate Similarity	NPC475379
0.75	Intermediate Similarity	NPC11025
0.75	Intermediate Similarity	NPC478124
0.75	Intermediate Similarity	NPC63470
0.75	Intermediate Similarity	NPC184464
0.75	Intermediate Similarity	NPC478264
0.75	Intermediate Similarity	NPC86772
0.75	Intermediate Similarity	NPC474620
0.75	Intermediate Similarity	NPC251062
0.7483	Intermediate Similarity	NPC79699
0.7483	Intermediate Similarity	NPC284957
0.7483	Intermediate Similarity	NPC148026
0.7469	Intermediate Similarity	NPC61891
0.7468	Intermediate Similarity	NPC477735
0.7468	Intermediate Similarity	NPC470330
0.7468	Intermediate Similarity	NPC181924
0.7467	Intermediate Similarity	NPC187566
0.7466	Intermediate Similarity	NPC471095
0.7466	Intermediate Similarity	NPC471066
0.7465	Intermediate Similarity	NPC9180
0.7465	Intermediate Similarity	NPC100402
0.7455	Intermediate Similarity	NPC246274
0.7455	Intermediate Similarity	NPC191653
0.7453	Intermediate Similarity	NPC329960
0.7453	Intermediate Similarity	NPC478125

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 NPC156393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	764
0.2-0.3	1553
0.3-0.4	2954
0.4-0.5	2374
0.5-0.6	982
0.6-0.7	281
0.7-0.8	12
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
0.7786	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7799	Discontinued
0.7536	Intermediate Similarity	NPD5125	Phase 3
0.7536	Intermediate Similarity	NPD5126	Approved
0.75	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8313	Approved
0.7235	Intermediate Similarity	NPD8312	Approved
0.7055	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6085	Phase 2
0.7051	Intermediate Similarity	NPD7236	Approved
0.7044	Intermediate Similarity	NPD7239	Suspended
0.7018	Intermediate Similarity	NPD6559	Discontinued
0.6978	Remote Similarity	NPD2629	Approved
0.6949	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7685	Pre-registration
0.6909	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6685	Approved
0.6872	Remote Similarity	NPD6535	Approved
0.6872	Remote Similarity	NPD6534	Approved
0.6857	Remote Similarity	NPD5951	Approved
0.6855	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6213	Phase 3
0.6816	Remote Similarity	NPD6212	Phase 3
0.6816	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7741	Discontinued
0.6768	Remote Similarity	NPD37	Approved
0.6759	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7699	Phase 2
0.6758	Remote Similarity	NPD7700	Phase 2
0.675	Remote Similarity	NPD2532	Approved
0.675	Remote Similarity	NPD2534	Approved
0.675	Remote Similarity	NPD2533	Approved
0.6748	Remote Similarity	NPD4380	Phase 2
0.6747	Remote Similarity	NPD4967	Phase 2
0.6747	Remote Similarity	NPD4965	Approved
0.6747	Remote Similarity	NPD4966	Approved
0.6744	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6005	Phase 3
0.6731	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6004	Phase 3
0.6731	Remote Similarity	NPD6002	Phase 3
0.6724	Remote Similarity	NPD8368	Discontinued
0.6723	Remote Similarity	NPD8150	Discontinued
0.6711	Remote Similarity	NPD5647	Approved
0.6709	Remote Similarity	NPD4628	Phase 3
0.6705	Remote Similarity	NPD8407	Phase 2
0.6689	Remote Similarity	NPD7008	Discontinued
0.6686	Remote Similarity	NPD7228	Approved
0.6686	Remote Similarity	NPD3818	Discontinued
0.6685	Remote Similarity	NPD6781	Approved
0.6685	Remote Similarity	NPD6780	Approved
0.6685	Remote Similarity	NPD6777	Approved
0.6685	Remote Similarity	NPD6778	Approved
0.6685	Remote Similarity	NPD6779	Approved
0.6685	Remote Similarity	NPD6782	Approved
0.6685	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD5765	Approved
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7057	Phase 3
0.6647	Remote Similarity	NPD7058	Phase 2
0.6643	Remote Similarity	NPD6912	Phase 3
0.6642	Remote Similarity	NPD6412	Phase 2
0.6631	Remote Similarity	NPD8320	Phase 1
0.6631	Remote Similarity	NPD8319	Approved
0.6624	Remote Similarity	NPD2346	Discontinued
0.6618	Remote Similarity	NPD1237	Approved
0.6613	Remote Similarity	NPD6823	Phase 2
0.6609	Remote Similarity	NPD7074	Phase 3
0.6604	Remote Similarity	NPD2575	Approved
0.6603	Remote Similarity	NPD7305	Phase 1
0.6601	Remote Similarity	NPD6663	Approved
0.6601	Remote Similarity	NPD7961	Discontinued
0.6596	Remote Similarity	NPD7094	Approved
0.6596	Remote Similarity	NPD6858	Approved
0.6585	Remote Similarity	NPD3226	Approved
0.6578	Remote Similarity	NPD7435	Discontinued
0.6575	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5048	Discontinued
0.6556	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5736	Approved
0.6552	Remote Similarity	NPD7009	Phase 2
0.6552	Remote Similarity	NPD7054	Approved
0.6544	Remote Similarity	NPD1929	Approved
0.6544	Remote Similarity	NPD1930	Approved
0.6544	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6647	Phase 2
0.6533	Remote Similarity	NPD1470	Approved
0.6533	Remote Similarity	NPD3094	Phase 2
0.6532	Remote Similarity	NPD7473	Discontinued
0.6527	Remote Similarity	NPD5760	Phase 2
0.6527	Remote Similarity	NPD8455	Phase 2
0.6527	Remote Similarity	NPD5761	Phase 2
0.6519	Remote Similarity	NPD5762	Approved
0.6519	Remote Similarity	NPD5763	Approved
0.6519	Remote Similarity	NPD7266	Discontinued
0.6514	Remote Similarity	NPD7472	Approved
0.6509	Remote Similarity	NPD7075	Discontinued
0.6503	Remote Similarity	NPD6273	Approved
0.65	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6959	Discontinued
0.6489	Remote Similarity	NPD7696	Phase 3
0.6489	Remote Similarity	NPD7698	Approved
0.6489	Remote Similarity	NPD7697	Approved
0.6486	Remote Similarity	NPD1201	Approved
0.6485	Remote Similarity	NPD7458	Discontinued
0.6481	Remote Similarity	NPD7390	Discontinued
0.6477	Remote Similarity	NPD6797	Phase 2
0.6464	Remote Similarity	NPD8360	Approved
0.6464	Remote Similarity	NPD8361	Approved
0.6458	Remote Similarity	NPD3317	Approved
0.6456	Remote Similarity	NPD7137	Phase 2
0.6456	Remote Similarity	NPD5404	Approved
0.6456	Remote Similarity	NPD5405	Approved
0.6456	Remote Similarity	NPD5408	Approved
0.6456	Remote Similarity	NPD5406	Approved
0.6455	Remote Similarity	NPD7870	Phase 2
0.6455	Remote Similarity	NPD7871	Phase 2
0.6453	Remote Similarity	NPD6232	Discontinued
0.6446	Remote Similarity	NPD7028	Phase 2
0.6444	Remote Similarity	NPD8434	Phase 2
0.6444	Remote Similarity	NPD2066	Phase 3
0.6441	Remote Similarity	NPD7240	Approved
0.6441	Remote Similarity	NPD7251	Discontinued
0.644	Remote Similarity	NPD7701	Phase 2
0.6438	Remote Similarity	NPD6674	Discontinued
0.6429	Remote Similarity	NPD7819	Suspended
0.6429	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3764	Approved
0.6429	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7801	Approved
0.6423	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD969	Suspended
0.6406	Remote Similarity	NPD8151	Discontinued
0.6405	Remote Similarity	NPD2613	Approved
0.6404	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7808	Phase 3
0.6395	Remote Similarity	NPD7199	Phase 2
0.6391	Remote Similarity	NPD1693	Approved
0.6391	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD2067	Discontinued
0.6377	Remote Similarity	NPD164	Approved
0.6376	Remote Similarity	NPD3092	Approved
0.6376	Remote Similarity	NPD5618	Discontinued
0.6374	Remote Similarity	NPD8435	Approved
0.6373	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7874	Approved
0.637	Remote Similarity	NPD9495	Approved
0.637	Remote Similarity	NPD7610	Discontinued
0.6369	Remote Similarity	NPD6801	Discontinued
0.6369	Remote Similarity	NPD6653	Approved
0.6364	Remote Similarity	NPD5844	Phase 1
0.6358	Remote Similarity	NPD5710	Approved
0.6358	Remote Similarity	NPD5711	Approved
0.6351	Remote Similarity	NPD5305	Approved
0.6351	Remote Similarity	NPD5306	Approved
0.6351	Remote Similarity	NPD3019	Approved
0.6351	Remote Similarity	NPD2932	Approved
0.6335	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD6010	Discontinued
0.6316	Remote Similarity	NPD7319	Approved
0.6294	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5402	Approved
0.6289	Remote Similarity	NPD2799	Discontinued
0.6282	Remote Similarity	NPD2570	Approved
0.6282	Remote Similarity	NPD3090	Approved
0.6282	Remote Similarity	NPD2571	Approved
0.6282	Remote Similarity	NPD2574	Discontinued
0.6282	Remote Similarity	NPD4746	Phase 3
0.6282	Remote Similarity	NPD3089	Approved
0.6282	Remote Similarity	NPD4745	Approved
0.6282	Remote Similarity	NPD3616	Approved
0.6282	Remote Similarity	NPD3615	Approved
0.6282	Remote Similarity	NPD3088	Approved
0.6282	Remote Similarity	NPD3087	Approved
0.6282	Remote Similarity	NPD2573	Approved
0.6282	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2566	Approved
0.6282	Remote Similarity	NPD3614	Approved
0.6279	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD2798	Approved
0.6273	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD1934	Approved
0.6267	Remote Similarity	NPD4806	Approved
0.6267	Remote Similarity	NPD4807	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data