NPASS Compound

Structure

CID292233 OpenBabel06191716102D 42 48 0 0 1 0 0 0 0 0999 V2000 -0.6089 4.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2072 4.3339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0508 3.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0805 0.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4104 1.3914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7750 0.5612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6073 1.8554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5538 2.8655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8032 2.3199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7032 1.0571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5012 1.4297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6069 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2140 1.8566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5692 2.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8372 2.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4566 3.7883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5692 1.5571 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.8372 1.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4436 0.6610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4102 0.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8326 1.3299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8035 1.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0178 1.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1957 1.7641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8033 0.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4103 1.3924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0180 0.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4105 0.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2143 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6074 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7032 3.0571 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8034 1.3920 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8036 0.4640 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5427 0.2271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2440 -0.0183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8604 1.8794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2145 -0.9727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6077 -0.9625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8038 -0.4989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1381 2.5328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6070 1.8560 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 31 1 0 0 0 0 4 6 2 0 0 0 0 4 19 1 0 0 0 0 5 7 2 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 32 1 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 11 24 1 0 0 0 0 12 20 2 0 0 0 0 12 25 1 0 0 0 0 13 23 2 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 31 1 0 0 0 0 15 18 2 0 0 0 0 15 31 1 0 0 0 0 17 21 1 0 0 0 0 18 27 1 0 0 0 0 19 34 1 0 0 0 0 20 35 1 0 0 0 0 21 24 2 0 0 0 0 22 25 2 0 0 0 0 22 32 1 0 0 0 0 23 27 1 0 0 0 0 23 36 1 0 0 0 0 24 40 1 0 0 0 0 25 42 1 0 0 0 0 26 28 2 0 0 0 0 26 41 1 0 0 0 0 27 29 2 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 29 37 1 0 0 0 0 30 33 1 0 0 0 0 30 38 2 0 0 0 0 31 40 1 0 0 0 0 32 33 1 0 0 0 0 32 41 1 0 0 0 0 33 39 1 0 0 0 0 33 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.19
Volume:	566.903
LogP:	6.588
LogD:	3.811
LogS:	-3.133
# Rotatable Bonds:	3
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.257
Synthetic Accessibility Score:	5.694
Fsp3:	0.303
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.266
MDCK Permeability:	1.3595708878710866e-05
Pgp-inhibitor:	0.098
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.62
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	99.32416534423828%
Volume Distribution (VD):	0.478
Pgp-substrate:	1.2006700038909912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.55
CYP1A2-substrate:	0.452
CYP2C19-inhibitor:	0.627
CYP2C19-substrate:	0.151
CYP2C9-inhibitor:	0.753
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.646
CYP2D6-substrate:	0.324
CYP3A4-inhibitor:	0.761
CYP3A4-substrate:	0.732

ADMET: Excretion

Clearance (CL):	9.138
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.731
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.402
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.884
Carcinogencity:	0.843
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.147

Download Data

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

Natural Product: NPC292233

Natural Product ID:	NPC292233
*Common Name:**	Sanggenon B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GJKQLIDFFREHGO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C33H30O9/c1-16(2)8-9-32-22-7-5-20(35)12-25(22)42-33(32,39)30(38)28-26(41-32)13-23(36)27(29(28)37)18-10-17-14-31(3,15-18)40-24-11-19(34)4-6-21(17)24/h4-8,11-13,15,17,34-37,39H,9-10,14H2,1-3H3
SMILES:	CC(=CCC12c3ccc(cc3OC1(C(=O)c1c(cc(c(C3=CC4(C)CC(C3)c3ccc(cc3O4)O)c1O)O)O2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507430
PubChem CID:	44559963
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429996]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19338315]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
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.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	Fruits	Zhenjiang, Jiangsu Province, China		PMID[23060696]
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]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14875	Morus cathayana	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]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	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[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9402	Morus mongolica	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
IC50	2
Others	4

Activity Type	# Activity
Cell Line	1
Individual Protein	2
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	39000.0	nM	PMID[542989]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	42000.0	nM	PMID[542990]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	100000.0	nM	PMID[542990]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	=	47000.0	nM	PMID[542989]
NPT27	Others	Unspecified		CC50	=	98000.0	nM	PMID[542989]
NPT27	Others	Unspecified		Ratio	=	2.5	n.a.	PMID[542989]

☑ 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 NPC292233 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	422
0.1-0.2	1712
0.2-0.3	3767
0.3-0.4	9731
0.4-0.5	8834
0.5-0.6	4061
0.6-0.7	6119
0.7-0.8	5511
0.8-0.85	2260
0.85-0.9	263
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC474276
0.963	High Similarity	NPC17105
0.963	High Similarity	NPC73899
0.963	High Similarity	NPC147363
0.943	High Similarity	NPC264932
0.943	High Similarity	NPC311574
0.9371	High Similarity	NPC172687
0.9367	High Similarity	NPC161650
0.9367	High Similarity	NPC210048
0.9268	High Similarity	NPC8704
0.9268	High Similarity	NPC287884
0.9212	High Similarity	NPC477529
0.9012	High Similarity	NPC306978
0.9006	High Similarity	NPC106700
0.8976	High Similarity	NPC5319
0.897	High Similarity	NPC82330
0.8963	High Similarity	NPC63438
0.8957	High Similarity	NPC92589
0.8944	High Similarity	NPC146636
0.8941	High Similarity	NPC244903
0.8909	High Similarity	NPC473010
0.8902	High Similarity	NPC259834
0.8902	High Similarity	NPC93215
0.8902	High Similarity	NPC282636
0.8902	High Similarity	NPC294863
0.8882	High Similarity	NPC476169
0.8875	High Similarity	NPC210597
0.8848	High Similarity	NPC179198
0.8848	High Similarity	NPC473009
0.8848	High Similarity	NPC66087
0.8848	High Similarity	NPC183672
0.8848	High Similarity	NPC278419
0.8841	High Similarity	NPC312273
0.8841	High Similarity	NPC301256
0.8834	High Similarity	NPC123544
0.8834	High Similarity	NPC125969
0.883	High Similarity	NPC121888
0.8827	High Similarity	NPC10754
0.8827	High Similarity	NPC20530
0.8827	High Similarity	NPC215917
0.8824	High Similarity	NPC101991
0.882	High Similarity	NPC100134
0.882	High Similarity	NPC236756
0.882	High Similarity	NPC209760
0.882	High Similarity	NPC20907
0.882	High Similarity	NPC311579
0.882	High Similarity	NPC244250
0.8817	High Similarity	NPC24748
0.8817	High Similarity	NPC168789
0.8817	High Similarity	NPC59491
0.8812	High Similarity	NPC472636
0.881	High Similarity	NPC102277
0.881	High Similarity	NPC279209
0.8788	High Similarity	NPC44947
0.8788	High Similarity	NPC473012
0.8788	High Similarity	NPC310603
0.8788	High Similarity	NPC150164
0.8788	High Similarity	NPC131745
0.8786	High Similarity	NPC75574
0.878	High Similarity	NPC153342
0.8773	High Similarity	NPC1796
0.8773	High Similarity	NPC475184
0.8765	High Similarity	NPC471116
0.8765	High Similarity	NPC304745
0.8765	High Similarity	NPC259710
0.8765	High Similarity	NPC217706
0.8765	High Similarity	NPC469934
0.8765	High Similarity	NPC207809
0.8765	High Similarity	NPC111341
0.8765	High Similarity	NPC304207
0.8765	High Similarity	NPC48579
0.8758	High Similarity	NPC475790
0.8758	High Similarity	NPC216035
0.8758	High Similarity	NPC473996
0.8758	High Similarity	NPC217149
0.875	High Similarity	NPC41598
0.8742	High Similarity	NPC296869
0.8735	High Similarity	NPC257566
0.8735	High Similarity	NPC124155
0.8727	High Similarity	NPC470125
0.8727	High Similarity	NPC265885
0.8727	High Similarity	NPC276377
0.8727	High Similarity	NPC47923
0.8727	High Similarity	NPC473438
0.8727	High Similarity	NPC253788
0.8727	High Similarity	NPC249281
0.8727	High Similarity	NPC181465
0.8727	High Similarity	NPC116458
0.8727	High Similarity	NPC246943
0.8727	High Similarity	NPC97812
0.8727	High Similarity	NPC175513
0.8727	High Similarity	NPC173582
0.8727	High Similarity	NPC139320
0.8727	High Similarity	NPC476215
0.8727	High Similarity	NPC215710
0.8727	High Similarity	NPC114652
0.8727	High Similarity	NPC163242
0.8727	High Similarity	NPC476929
0.872	High Similarity	NPC295090
0.872	High Similarity	NPC308265
0.872	High Similarity	NPC105584
0.872	High Similarity	NPC51247
0.8712	High Similarity	NPC56049
0.8712	High Similarity	NPC192587
0.8712	High Similarity	NPC54830
0.8712	High Similarity	NPC69531
0.8706	High Similarity	NPC470335
0.8706	High Similarity	NPC470336
0.8704	High Similarity	NPC268193
0.8704	High Similarity	NPC112701
0.8704	High Similarity	NPC203080
0.8704	High Similarity	NPC326592
0.8704	High Similarity	NPC109594
0.8704	High Similarity	NPC248793
0.8704	High Similarity	NPC180301
0.8698	High Similarity	NPC76047
0.8696	High Similarity	NPC319910
0.8696	High Similarity	NPC278476
0.8696	High Similarity	NPC471229
0.8696	High Similarity	NPC262039
0.8696	High Similarity	NPC472580
0.8696	High Similarity	NPC474023
0.8696	High Similarity	NPC471675
0.8696	High Similarity	NPC474021
0.8696	High Similarity	NPC262038
0.8696	High Similarity	NPC254412
0.8696	High Similarity	NPC178484
0.869	High Similarity	NPC476459
0.8688	High Similarity	NPC473016
0.8688	High Similarity	NPC277032
0.8683	High Similarity	NPC72016
0.8683	High Similarity	NPC329215
0.8683	High Similarity	NPC204088
0.8683	High Similarity	NPC259007
0.8679	High Similarity	NPC166757
0.8679	High Similarity	NPC14001
0.8679	High Similarity	NPC472918
0.8675	High Similarity	NPC475106
0.8675	High Similarity	NPC190450
0.8675	High Similarity	NPC240306
0.8671	High Similarity	NPC71210
0.8671	High Similarity	NPC326500
0.8667	High Similarity	NPC195136
0.8667	High Similarity	NPC470405
0.8667	High Similarity	NPC98023
0.8667	High Similarity	NPC121647
0.8667	High Similarity	NPC471079
0.8667	High Similarity	NPC226462
0.8667	High Similarity	NPC304741
0.8667	High Similarity	NPC271479
0.8667	High Similarity	NPC472320
0.8667	High Similarity	NPC187379
0.8667	High Similarity	NPC200708
0.8667	High Similarity	NPC42965
0.8659	High Similarity	NPC287789
0.8659	High Similarity	NPC271741
0.8659	High Similarity	NPC257166
0.8655	High Similarity	NPC232412
0.8655	High Similarity	NPC98667
0.8655	High Similarity	NPC86809
0.8655	High Similarity	NPC108202
0.8655	High Similarity	NPC294629
0.865	High Similarity	NPC52611
0.865	High Similarity	NPC248739
0.865	High Similarity	NPC159707
0.865	High Similarity	NPC14606
0.865	High Similarity	NPC100049
0.865	High Similarity	NPC265624
0.865	High Similarity	NPC275575
0.865	High Similarity	NPC186227
0.865	High Similarity	NPC121649
0.865	High Similarity	NPC215203
0.865	High Similarity	NPC477958
0.865	High Similarity	NPC205026
0.865	High Similarity	NPC300668
0.865	High Similarity	NPC150908
0.865	High Similarity	NPC134171
0.865	High Similarity	NPC158027
0.8647	High Similarity	NPC186847
0.8647	High Similarity	NPC472454
0.8647	High Similarity	NPC257667
0.8647	High Similarity	NPC474522
0.8642	High Similarity	NPC244583
0.8642	High Similarity	NPC243171
0.8642	High Similarity	NPC138288
0.8642	High Similarity	NPC56232
0.8642	High Similarity	NPC35567
0.8642	High Similarity	NPC171651
0.8642	High Similarity	NPC327269
0.8642	High Similarity	NPC31627
0.8642	High Similarity	NPC150123
0.8642	High Similarity	NPC161881
0.8642	High Similarity	NPC476238
0.8642	High Similarity	NPC10807
0.8642	High Similarity	NPC477957
0.8639	High Similarity	NPC476146
0.8639	High Similarity	NPC40089
0.8639	High Similarity	NPC476216
0.8639	High Similarity	NPC158329
0.8634	High Similarity	NPC476509

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 NPC292233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	930
0.2-0.3	1695
0.3-0.4	2721
0.4-0.5	1950
0.5-0.6	988
0.6-0.7	329
0.7-0.8	137
0.8-0.85	29
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8976	High Similarity	NPD7804	Clinical (unspecified phase)
0.8659	High Similarity	NPD7075	Discontinued
0.865	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD6167	Clinical (unspecified phase)
0.8571	High Similarity	NPD6168	Clinical (unspecified phase)
0.8571	High Similarity	NPD6166	Phase 2
0.8553	High Similarity	NPD4378	Clinical (unspecified phase)
0.8553	High Similarity	NPD7410	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD7808	Phase 3
0.8434	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD6797	Phase 2
0.8405	Intermediate Similarity	NPD4380	Phase 2
0.8382	Intermediate Similarity	NPD7251	Discontinued
0.8354	Intermediate Similarity	NPD7411	Suspended
0.8353	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6801	Discontinued
0.8284	Intermediate Similarity	NPD6959	Discontinued
0.8266	Intermediate Similarity	NPD7074	Phase 3
0.8253	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD3749	Approved
0.8208	Intermediate Similarity	NPD7054	Approved
0.8171	Intermediate Similarity	NPD6559	Discontinued
0.8161	Intermediate Similarity	NPD7472	Approved
0.8155	Intermediate Similarity	NPD3882	Suspended
0.8148	Intermediate Similarity	NPD6799	Approved
0.8144	Intermediate Similarity	NPD7819	Suspended
0.8118	Intermediate Similarity	NPD5494	Approved
0.8095	Intermediate Similarity	NPD3817	Phase 2
0.8084	Intermediate Similarity	NPD1934	Approved
0.8072	Intermediate Similarity	NPD6599	Discontinued
0.8066	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD1512	Approved
0.8047	Intermediate Similarity	NPD7768	Phase 2
0.8046	Intermediate Similarity	NPD3818	Discontinued
0.8023	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2800	Approved
0.8011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7473	Discontinued
0.795	Intermediate Similarity	NPD1549	Phase 2
0.7941	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2801	Approved
0.7927	Intermediate Similarity	NPD1511	Approved
0.7919	Intermediate Similarity	NPD6232	Discontinued
0.7892	Intermediate Similarity	NPD5403	Approved
0.7877	Intermediate Similarity	NPD8313	Approved
0.7877	Intermediate Similarity	NPD8312	Approved
0.7853	Intermediate Similarity	NPD3750	Approved
0.7841	Intermediate Similarity	NPD3751	Discontinued
0.7778	Intermediate Similarity	NPD5402	Approved
0.7771	Intermediate Similarity	NPD5401	Approved
0.7771	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1510	Phase 2
0.7736	Intermediate Similarity	NPD1240	Approved
0.7719	Intermediate Similarity	NPD8455	Phase 2
0.7716	Intermediate Similarity	NPD2796	Approved
0.7714	Intermediate Similarity	NPD3787	Discontinued
0.7701	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7692	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1607	Approved
0.7616	Intermediate Similarity	NPD1465	Phase 2
0.761	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7390	Discontinued
0.7579	Intermediate Similarity	NPD6779	Approved
0.7579	Intermediate Similarity	NPD6778	Approved
0.7579	Intermediate Similarity	NPD6781	Approved
0.7579	Intermediate Similarity	NPD6782	Approved
0.7579	Intermediate Similarity	NPD6777	Approved
0.7579	Intermediate Similarity	NPD6780	Approved
0.7579	Intermediate Similarity	NPD6776	Approved
0.7576	Intermediate Similarity	NPD1243	Approved
0.7574	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3926	Phase 2
0.7568	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2344	Approved
0.756	Intermediate Similarity	NPD2532	Approved
0.756	Intermediate Similarity	NPD2533	Approved
0.756	Intermediate Similarity	NPD2534	Approved
0.7557	Intermediate Similarity	NPD7199	Phase 2
0.7554	Intermediate Similarity	NPD8150	Discontinued
0.7554	Intermediate Similarity	NPD8434	Phase 2
0.7552	Intermediate Similarity	NPD7698	Approved
0.7552	Intermediate Similarity	NPD7696	Phase 3
0.7552	Intermediate Similarity	NPD7435	Discontinued
0.7552	Intermediate Similarity	NPD7697	Approved
0.7546	Intermediate Similarity	NPD2799	Discontinued
0.7546	Intermediate Similarity	NPD3748	Approved
0.7543	Intermediate Similarity	NPD919	Approved
0.7531	Intermediate Similarity	NPD6651	Approved
0.7527	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7485	Intermediate Similarity	NPD3226	Approved
0.7485	Intermediate Similarity	NPD7458	Discontinued
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7471	Intermediate Similarity	NPD920	Approved
0.7462	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7783	Phase 2
0.7458	Intermediate Similarity	NPD1247	Approved
0.7449	Intermediate Similarity	NPD8151	Discontinued
0.7444	Intermediate Similarity	NPD7228	Approved
0.743	Intermediate Similarity	NPD2403	Approved
0.7425	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD8320	Phase 1
0.7423	Intermediate Similarity	NPD8319	Approved
0.7411	Intermediate Similarity	NPD7874	Approved
0.7411	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7394	Intermediate Similarity	NPD6100	Approved
0.7394	Intermediate Similarity	NPD6099	Approved
0.7382	Intermediate Similarity	NPD7700	Phase 2
0.7382	Intermediate Similarity	NPD7699	Phase 2
0.7381	Intermediate Similarity	NPD2309	Approved
0.7374	Intermediate Similarity	NPD7801	Approved
0.7358	Intermediate Similarity	NPD2798	Approved
0.7353	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7584	Approved
0.7345	Intermediate Similarity	NPD6234	Discontinued
0.7337	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5953	Discontinued
0.7321	Intermediate Similarity	NPD4628	Phase 3
0.7316	Intermediate Similarity	NPD6535	Approved
0.7316	Intermediate Similarity	NPD6534	Approved
0.7294	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1551	Phase 2
0.7287	Intermediate Similarity	NPD4287	Approved
0.7284	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6798	Discontinued
0.7284	Intermediate Similarity	NPD2313	Discontinued
0.7257	Intermediate Similarity	NPD37	Approved
0.7256	Intermediate Similarity	NPD6355	Discontinued
0.7251	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2346	Discontinued
0.7232	Intermediate Similarity	NPD4967	Phase 2
0.7232	Intermediate Similarity	NPD4965	Approved
0.7232	Intermediate Similarity	NPD4966	Approved
0.7229	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4363	Phase 3
0.7225	Intermediate Similarity	NPD4360	Phase 2
0.7222	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7286	Phase 2
0.7178	Intermediate Similarity	NPD3268	Approved
0.7178	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7136	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7127	Intermediate Similarity	NPD5710	Approved
0.7127	Intermediate Similarity	NPD5711	Approved
0.7118	Intermediate Similarity	NPD7003	Approved
0.711	Intermediate Similarity	NPD5049	Phase 3
0.7098	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4361	Phase 2
0.7097	Intermediate Similarity	NPD7240	Approved
0.7097	Intermediate Similarity	NPD7685	Pre-registration
0.7091	Intermediate Similarity	NPD4060	Phase 1
0.7091	Intermediate Similarity	NPD943	Approved
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1203	Approved
0.7081	Intermediate Similarity	NPD2797	Approved
0.7076	Intermediate Similarity	NPD2354	Approved
0.7066	Intermediate Similarity	NPD7097	Phase 1
0.7055	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1933	Approved
0.7048	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5124	Phase 1
0.7044	Intermediate Similarity	NPD1610	Phase 2
0.7041	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1471	Phase 3
0.7024	Intermediate Similarity	NPD7033	Discontinued
0.7012	Intermediate Similarity	NPD7095	Approved
0.7012	Intermediate Similarity	NPD4625	Phase 3
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4288	Approved
0.6982	Remote Similarity	NPD5406	Approved
0.6982	Remote Similarity	NPD5404	Approved
0.6982	Remote Similarity	NPD5405	Approved
0.6982	Remote Similarity	NPD5408	Approved
0.6977	Remote Similarity	NPD6190	Approved
0.6965	Remote Similarity	NPD7585	Approved
0.6961	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4749	Approved
0.6954	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6832	Phase 2
0.6927	Remote Similarity	NPD7930	Approved
0.6923	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4308	Phase 3
0.6915	Remote Similarity	NPD7583	Approved
0.6901	Remote Similarity	NPD2424	Discontinued
0.6894	Remote Similarity	NPD9717	Approved
0.6894	Remote Similarity	NPD1608	Approved
0.6889	Remote Similarity	NPD2296	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