NPASS Compound

Structure

CID49130 OpenBabel06191715382D 22 24 0 0 1 0 0 0 0 0999 V2000 2.5981 -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 3.4641 0.0000 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 -1.7321 -0.0000 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 -2.5981 0.5000 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 2.5981 0.5000 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 -0.8660 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 -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 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 6 1 0 0 0 0 2 8 1 0 0 0 0 3 6 2 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 8 1 1 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.06
Volume:	285.403
LogP:	0.535
LogD:	-0.055
LogS:	-2.606
# Rotatable Bonds:	1
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	3.62
Fsp3:	0.133
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:	-6.08
MDCK Permeability:	3.9741748878441285e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.886
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	84.05945587158203%
Volume Distribution (VD):	1.139
Pgp-substrate:	15.778668403625488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.417
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.147
CYP2D6-substrate:	0.328
CYP3A4-inhibitor:	0.222
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	8.411
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.379
Rat Oral Acute Toxicity:	0.228
Maximum Recommended Daily Dose:	0.568
Skin Sensitization:	0.927
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.906
Respiratory Toxicity:	0.442

Download Data

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

Natural Product: NPC49130

Natural Product ID:	NPC49130
*Common Name:**	Dihydromorin
IUPAC Name:	(2R,3R)-2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Synonyms:	(2R,3R)-5,7,2',4'-Tetrahydroxyflavanonol; Dihydromorin
Standard InCHIKey:	QIWOFDHUQPJCJF-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C15H12O7/c16-6-1-2-8(9(18)3-6)15-14(21)13(20)12-10(19)4-7(17)5-11(12)22-15/h1-5,14-19,21H/t14-,15+/m0/s1
SMILES:	Oc1ccc(c(c1)O)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463453
PubChem CID:	5458714
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones [CHEMONTID:0001362] Flavanonols

*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
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869218]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	bark and twigs	Tewah, Central Kalimantan, Indonesia (N 38 57.003; W 094 44.767)	1999-Oct	PMID[11858749]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217294]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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
EC50	1
IC50	3
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	>	40.0	ug.mL-1	PMID[494877]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	67100.0	nM	PMID[494878]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	100000.0	nM	PMID[494878]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	10.0	%	PMID[494879]
NPT2	Others	Unspecified		Inhibition	=	81.5	%	PMID[494878]
NPT35	Others	n.a.		EC50	>	100000.0	nM	PMID[494879]

☑ 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 NPC49130 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	413
0.1-0.2	1656
0.2-0.3	4364
0.3-0.4	10414
0.4-0.5	7503
0.5-0.6	3840
0.6-0.7	5428
0.7-0.8	5112
0.8-0.85	2475
0.85-0.9	1150
0.9-0.95	293
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC279417
1.0	High Similarity	NPC142731
1.0	High Similarity	NPC62290
1.0	High Similarity	NPC4152
1.0	High Similarity	NPC306607
1.0	High Similarity	NPC208176
1.0	High Similarity	NPC326506
0.9928	High Similarity	NPC1940
0.9928	High Similarity	NPC148011
0.9857	High Similarity	NPC476182
0.9857	High Similarity	NPC211466
0.9857	High Similarity	NPC176869
0.9857	High Similarity	NPC40086
0.9857	High Similarity	NPC44721
0.9857	High Similarity	NPC3779
0.9857	High Similarity	NPC122828
0.9787	High Similarity	NPC218569
0.9716	High Similarity	NPC21835
0.9645	High Similarity	NPC229190
0.964	High Similarity	NPC150023
0.9583	High Similarity	NPC262039
0.9583	High Similarity	NPC278476
0.9583	High Similarity	NPC262038
0.9583	High Similarity	NPC254412
0.9583	High Similarity	NPC319910
0.9577	High Similarity	NPC472918
0.9517	High Similarity	NPC243171
0.9517	High Similarity	NPC138288
0.9517	High Similarity	NPC61506
0.9517	High Similarity	NPC260491
0.9517	High Similarity	NPC240476
0.9517	High Similarity	NPC171651
0.9517	High Similarity	NPC35567
0.9517	High Similarity	NPC216035
0.9517	High Similarity	NPC9743
0.9517	High Similarity	NPC36835
0.9517	High Similarity	NPC217149
0.9517	High Similarity	NPC246162
0.9514	High Similarity	NPC105136
0.9493	High Similarity	NPC12296
0.9493	High Similarity	NPC243083
0.9493	High Similarity	NPC32441
0.9493	High Similarity	NPC287246
0.9493	High Similarity	NPC13768
0.9493	High Similarity	NPC295261
0.9493	High Similarity	NPC296490
0.9493	High Similarity	NPC107586
0.9493	High Similarity	NPC79943
0.9452	High Similarity	NPC325028
0.9452	High Similarity	NPC27532
0.9452	High Similarity	NPC244250
0.9452	High Similarity	NPC246328
0.9452	High Similarity	NPC256346
0.9452	High Similarity	NPC20907
0.9452	High Similarity	NPC293286
0.9452	High Similarity	NPC268193
0.9444	High Similarity	NPC277032
0.9444	High Similarity	NPC477941
0.9424	High Similarity	NPC147686
0.9424	High Similarity	NPC329225
0.9424	High Similarity	NPC472460
0.9388	High Similarity	NPC111341
0.9388	High Similarity	NPC48579
0.9388	High Similarity	NPC207809
0.9388	High Similarity	NPC304207
0.9388	High Similarity	NPC304745
0.9388	High Similarity	NPC259710
0.9388	High Similarity	NPC217706
0.9384	High Similarity	NPC19721
0.9379	High Similarity	NPC267117
0.9357	High Similarity	NPC310135
0.9357	High Similarity	NPC274784
0.9357	High Similarity	NPC329203
0.9357	High Similarity	NPC20709
0.9357	High Similarity	NPC265871
0.9357	High Similarity	NPC222342
0.9357	High Similarity	NPC150648
0.9357	High Similarity	NPC225153
0.9353	High Similarity	NPC476480
0.9353	High Similarity	NPC84585
0.9353	High Similarity	NPC287068
0.9324	High Similarity	NPC320825
0.9324	High Similarity	NPC10754
0.9324	High Similarity	NPC201837
0.9324	High Similarity	NPC20530
0.9324	High Similarity	NPC215917
0.9324	High Similarity	NPC326037
0.9324	High Similarity	NPC13858
0.932	High Similarity	NPC203080
0.932	High Similarity	NPC180301
0.932	High Similarity	NPC248793
0.9315	High Similarity	NPC209846
0.9315	High Similarity	NPC471677
0.9315	High Similarity	NPC471229
0.9315	High Similarity	NPC472422
0.9315	High Similarity	NPC472420
0.9315	High Similarity	NPC471676
0.9315	High Similarity	NPC328740
0.9315	High Similarity	NPC263384
0.9315	High Similarity	NPC289774
0.9315	High Similarity	NPC295650
0.9315	High Similarity	NPC477897
0.9315	High Similarity	NPC244577
0.931	High Similarity	NPC472628
0.9306	High Similarity	NPC472627
0.9291	High Similarity	NPC6407
0.9291	High Similarity	NPC110228
0.9291	High Similarity	NPC188243
0.9291	High Similarity	NPC182421
0.9286	High Similarity	NPC118813
0.9281	High Similarity	NPC187432
0.9281	High Similarity	NPC256042
0.9281	High Similarity	NPC281917
0.9281	High Similarity	NPC116775
0.9281	High Similarity	NPC216361
0.9262	High Similarity	NPC52530
0.9262	High Similarity	NPC6985
0.9252	High Similarity	NPC475790
0.9252	High Similarity	NPC259182
0.9252	High Similarity	NPC121001
0.9252	High Similarity	NPC210597
0.9252	High Similarity	NPC150123
0.9252	High Similarity	NPC244583
0.9252	High Similarity	NPC10807
0.9252	High Similarity	NPC161881
0.9252	High Similarity	NPC56232
0.9241	High Similarity	NPC294852
0.9241	High Similarity	NPC321011
0.9241	High Similarity	NPC188679
0.9236	High Similarity	NPC472629
0.9225	High Similarity	NPC312391
0.9225	High Similarity	NPC324386
0.9225	High Similarity	NPC4743
0.9225	High Similarity	NPC213322
0.922	High Similarity	NPC261234
0.922	High Similarity	NPC241838
0.922	High Similarity	NPC152042
0.922	High Similarity	NPC143799
0.922	High Similarity	NPC316480
0.922	High Similarity	NPC140890
0.9214	High Similarity	NPC290291
0.9214	High Similarity	NPC299379
0.9214	High Similarity	NPC275055
0.9209	High Similarity	NPC9985
0.9209	High Similarity	NPC239495
0.92	High Similarity	NPC123544
0.92	High Similarity	NPC22192
0.9195	High Similarity	NPC323593
0.9195	High Similarity	NPC307938
0.9195	High Similarity	NPC471500
0.9195	High Similarity	NPC250922
0.9195	High Similarity	NPC203500
0.9189	High Similarity	NPC236756
0.9189	High Similarity	NPC106625
0.9189	High Similarity	NPC141212
0.9189	High Similarity	NPC209760
0.9189	High Similarity	NPC100134
0.9189	High Similarity	NPC311579
0.9189	High Similarity	NPC109594
0.9189	High Similarity	NPC472583
0.9189	High Similarity	NPC7989
0.9189	High Similarity	NPC326592
0.9189	High Similarity	NPC112701
0.9189	High Similarity	NPC223701
0.9184	High Similarity	NPC472636
0.9184	High Similarity	NPC474021
0.9184	High Similarity	NPC474023
0.9178	High Similarity	NPC1612
0.9178	High Similarity	NPC183959
0.9178	High Similarity	NPC89442
0.9172	High Similarity	NPC85773
0.9167	High Similarity	NPC87486
0.9167	High Similarity	NPC470890
0.9167	High Similarity	NPC124780
0.9161	High Similarity	NPC220998
0.9161	High Similarity	NPC73028
0.9161	High Similarity	NPC32739
0.9161	High Similarity	NPC265040
0.9161	High Similarity	NPC10937
0.9161	High Similarity	NPC296917
0.9161	High Similarity	NPC228504
0.9161	High Similarity	NPC227579
0.9161	High Similarity	NPC76338
0.9161	High Similarity	NPC324436
0.9161	High Similarity	NPC223500
0.9161	High Similarity	NPC64915
0.9161	High Similarity	NPC66515
0.9161	High Similarity	NPC324134
0.9161	High Similarity	NPC76372
0.9161	High Similarity	NPC161506
0.9161	High Similarity	NPC37496
0.9161	High Similarity	NPC107572
0.9161	High Similarity	NPC78
0.9161	High Similarity	NPC166482
0.9161	High Similarity	NPC40833
0.9161	High Similarity	NPC166934
0.9161	High Similarity	NPC306829
0.9161	High Similarity	NPC182852
0.9161	High Similarity	NPC177354
0.9161	High Similarity	NPC148757

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 NPC49130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	879
0.2-0.3	1753
0.3-0.4	2652
0.4-0.5	1764
0.5-0.6	1071
0.6-0.7	438
0.7-0.8	137
0.8-0.85	30
0.85-0.9	20
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9493	High Similarity	NPD1550	Clinical (unspecified phase)
0.9493	High Similarity	NPD1552	Clinical (unspecified phase)
0.9424	High Similarity	NPD1549	Phase 2
0.9122	High Similarity	NPD1934	Approved
0.9116	High Similarity	NPD4380	Phase 2
0.9034	High Similarity	NPD4378	Clinical (unspecified phase)
0.9007	High Similarity	NPD7075	Discontinued
0.9007	High Similarity	NPD4381	Clinical (unspecified phase)
0.8973	High Similarity	NPD1512	Approved
0.8936	High Similarity	NPD1510	Phase 2
0.8933	High Similarity	NPD2393	Clinical (unspecified phase)
0.8933	High Similarity	NPD7096	Clinical (unspecified phase)
0.8903	High Similarity	NPD6168	Clinical (unspecified phase)
0.8903	High Similarity	NPD6167	Clinical (unspecified phase)
0.8903	High Similarity	NPD6166	Phase 2
0.8867	High Similarity	NPD6801	Discontinued
0.8836	High Similarity	NPD6799	Approved
0.8836	High Similarity	NPD1511	Approved
0.8786	High Similarity	NPD1240	Approved
0.8734	High Similarity	NPD7804	Clinical (unspecified phase)
0.8662	High Similarity	NPD1607	Approved
0.8658	High Similarity	NPD5403	Approved
0.8649	High Similarity	NPD5401	Approved
0.8611	High Similarity	NPD2796	Approved
0.8609	High Similarity	NPD6599	Discontinued
0.8571	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD2801	Approved
0.8509	High Similarity	NPD6797	Phase 2
0.8506	High Similarity	NPD8443	Clinical (unspecified phase)
0.8506	High Similarity	NPD3817	Phase 2
0.8457	Intermediate Similarity	NPD7251	Discontinued
0.8447	Intermediate Similarity	NPD7074	Phase 3
0.8438	Intermediate Similarity	NPD3818	Discontinued
0.8431	Intermediate Similarity	NPD7411	Suspended
0.8405	Intermediate Similarity	NPD7808	Phase 3
0.8405	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD5402	Approved
0.8385	Intermediate Similarity	NPD7054	Approved
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7472	Approved
0.8231	Intermediate Similarity	NPD1551	Phase 2
0.8205	Intermediate Similarity	NPD7819	Suspended
0.8171	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1613	Approved
0.8138	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3750	Approved
0.8129	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6959	Discontinued
0.8121	Intermediate Similarity	NPD6559	Discontinued
0.8063	Intermediate Similarity	NPD5494	Approved
0.805	Intermediate Similarity	NPD3749	Approved
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2800	Approved
0.7947	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1203	Approved
0.7891	Intermediate Similarity	NPD943	Approved
0.7879	Intermediate Similarity	NPD3751	Discontinued
0.7875	Intermediate Similarity	NPD7768	Phase 2
0.7872	Intermediate Similarity	NPD1610	Phase 2
0.7862	Intermediate Similarity	NPD1465	Phase 2
0.7862	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1548	Phase 1
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7821	Intermediate Similarity	NPD920	Approved
0.7806	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD3748	Approved
0.7793	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1247	Approved
0.7778	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6798	Discontinued
0.7744	Intermediate Similarity	NPD6232	Discontinued
0.7744	Intermediate Similarity	NPD3787	Discontinued
0.7727	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1243	Approved
0.7711	Intermediate Similarity	NPD7473	Discontinued
0.7697	Intermediate Similarity	NPD2344	Approved
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7667	Intermediate Similarity	NPD6651	Approved
0.7647	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2313	Discontinued
0.7632	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD7286	Phase 2
0.7619	Intermediate Similarity	NPD4908	Phase 1
0.76	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1652	Phase 2
0.759	Intermediate Similarity	NPD3926	Phase 2
0.7584	Intermediate Similarity	NPD6233	Phase 2
0.758	Intermediate Similarity	NPD2532	Approved
0.758	Intermediate Similarity	NPD2533	Approved
0.758	Intermediate Similarity	NPD2534	Approved
0.7569	Intermediate Similarity	NPD9717	Approved
0.7566	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5953	Discontinued
0.7517	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD422	Phase 1
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD1933	Approved
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2799	Discontinued
0.7451	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3027	Phase 3
0.7407	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3268	Approved
0.7399	Intermediate Similarity	NPD8313	Approved
0.7399	Intermediate Similarity	NPD8312	Approved
0.7391	Intermediate Similarity	NPD3226	Approved
0.7389	Intermediate Similarity	NPD2354	Approved
0.7389	Intermediate Similarity	NPD6190	Approved
0.7379	Intermediate Similarity	NPD1091	Approved
0.7371	Intermediate Similarity	NPD8434	Phase 2
0.7368	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD5124	Phase 1
0.7358	Intermediate Similarity	NPD4662	Approved
0.7358	Intermediate Similarity	NPD4661	Approved
0.7355	Intermediate Similarity	NPD2346	Discontinued
0.7351	Intermediate Similarity	NPD7584	Approved
0.7347	Intermediate Similarity	NPD3225	Approved
0.7343	Intermediate Similarity	NPD9545	Approved
0.7337	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1653	Approved
0.7317	Intermediate Similarity	NPD8455	Phase 2
0.7308	Intermediate Similarity	NPD6779	Approved
0.7308	Intermediate Similarity	NPD2424	Discontinued
0.7308	Intermediate Similarity	NPD6782	Approved
0.7308	Intermediate Similarity	NPD6777	Approved
0.7308	Intermediate Similarity	NPD6776	Approved
0.7308	Intermediate Similarity	NPD6780	Approved
0.7308	Intermediate Similarity	NPD6778	Approved
0.7308	Intermediate Similarity	NPD6781	Approved
0.7297	Intermediate Similarity	NPD2797	Approved
0.7285	Intermediate Similarity	NPD1296	Phase 2
0.7278	Intermediate Similarity	NPD3887	Approved
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7199	Phase 2
0.7261	Intermediate Similarity	NPD2654	Approved
0.7255	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1019	Discontinued
0.7248	Intermediate Similarity	NPD2798	Approved
0.7237	Intermediate Similarity	NPD4062	Phase 3
0.7235	Intermediate Similarity	NPD2403	Approved
0.7234	Intermediate Similarity	NPD1241	Discontinued
0.7226	Intermediate Similarity	NPD4308	Phase 3
0.7215	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1608	Approved
0.7211	Intermediate Similarity	NPD1481	Phase 2
0.7203	Intermediate Similarity	NPD9493	Approved
0.72	Intermediate Similarity	NPD2861	Phase 2
0.7189	Intermediate Similarity	NPD7435	Discontinued
0.7188	Intermediate Similarity	NPD7390	Discontinued
0.7182	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4361	Phase 2
0.7181	Intermediate Similarity	NPD3267	Approved
0.7181	Intermediate Similarity	NPD3266	Approved
0.7178	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8150	Discontinued
0.7169	Intermediate Similarity	NPD4288	Approved
0.7168	Intermediate Similarity	NPD1729	Discontinued
0.7152	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7143	Intermediate Similarity	NPD4340	Discontinued
0.7135	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7134	Intermediate Similarity	NPD2353	Approved
0.7126	Intermediate Similarity	NPD3823	Discontinued
0.712	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5710	Approved
0.7118	Intermediate Similarity	NPD5711	Approved
0.7099	Intermediate Similarity	NPD5049	Phase 3
0.7097	Intermediate Similarity	NPD7697	Approved
0.7097	Intermediate Similarity	NPD7698	Approved
0.7097	Intermediate Similarity	NPD7696	Phase 3
0.7095	Intermediate Similarity	NPD4287	Approved
0.7095	Intermediate Similarity	NPD3972	Approved
0.7086	Intermediate Similarity	NPD9494	Approved
0.7086	Intermediate Similarity	NPD6104	Discontinued
0.7081	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4060	Phase 1
0.7073	Intermediate Similarity	NPD7458	Discontinued
0.7067	Intermediate Similarity	NPD1470	Approved
0.7059	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD7871	Phase 2
0.7059	Intermediate Similarity	NPD7870	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