NPASS Compound

Structure

CID47634 OpenBabel06191715382D 41 46 0 0 1 0 0 0 0 0999 V2000 0.2617 2.3939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1204 2.3939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9992 0.2561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2000 0.3676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5989 -0.3234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1541 1.4825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6426 1.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4293 1.1970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1204 0.7980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2589 0.1764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2408 -1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8010 -0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8657 0.3503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7978 -1.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2576 -0.3234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4293 1.9949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6061 0.4300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7978 -0.7320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6806 -0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1204 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5602 -0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5216 0.1190 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5602 -0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1204 -1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6806 -0.3234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5602 -0.3234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6950 -0.2212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5601 0.8574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8010 -0.3234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1350 0.8067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4837 0.1532 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5602 -0.3234 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1204 -2.0917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3576 -0.4045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9073 1.1110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1669 1.0313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2408 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0290 0.8067 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 17 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 31 1 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 30 1 0 0 0 0 13 32 1 0 0 0 0 14 21 2 0 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 17 29 1 0 0 0 0 18 14 1 1 0 0 0 18 28 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 25 1 0 0 0 0 22 31 1 0 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 27 2 0 0 0 0 24 34 1 0 0 0 0 25 35 2 0 0 0 0 26 39 1 0 0 0 0 27 40 1 0 0 0 0 28 32 1 0 0 0 0 28 36 2 0 0 0 0 29 37 2 0 0 0 0 29 38 1 0 0 0 0 30 39 1 0 0 0 0 31 41 1 0 0 0 0 32 33 1 1 0 0 0 32 41 1 0 0 0 0 33 21 1 1 0 0 0 33 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.24
Volume:	571.942
LogP:	6.386
LogD:	3.464
LogS:	-3.158
# Rotatable Bonds:	5
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	6.741
Fsp3:	0.485
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.912
MDCK Permeability:	1.7198735804413445e-05
Pgp-inhibitor:	0.19
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.487
20% Bioavailability (F20%):	0.307
30% Bioavailability (F30%):	0.599

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	98.00984954833984%
Volume Distribution (VD):	1.308
Pgp-substrate:	2.7878787517547607%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.572
CYP2C9-inhibitor:	0.298
CYP2C9-substrate:	0.248
CYP2D6-inhibitor:	0.117
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.444
CYP3A4-substrate:	0.577

ADMET: Excretion

Clearance (CL):	1.165
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.863
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.154
Carcinogencity:	0.923
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC47634

Natural Product ID:	NPC47634
*Common Name:**	COVMVPHACFXMAX-FYBISLNESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	COVMVPHACFXMAX-FYBISLNESA-N
Standard InCHI:	InChI=1S/C33H36O8/c1-16(2)8-9-20-26-19(11-12-30(4,5)39-26)24(34)23-25(35)21-14-18-15-22-31(6,7)41-32(28(18)36,13-10-17(3)29(37)38)33(21,22)40-27(20)23/h8,10-12,14,18,22,34H,9,13,15H2,1-7H3,(H,37,38)/b17-10-/t18-,22?,32+,33-/m0/s1
SMILES:	CC(=CCc1c2c(C=CC(C)(C)O2)c(c2C(=O)C3=C[C@H]4CC5C(C)(C)O[C@](C/C=C(/C)C(=O)O)(C4=O)[C@]35Oc12)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3809573
PubChem CID:	16078251
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
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]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
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	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
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	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]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	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]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	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
MIC	2
Others	4

Activity Type	# Activity
Cell Line	2
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3500.0	nM	PMID[570928]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	2330.0	nM	PMID[570928]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	19.23	mm	PMID[570928]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12500.0	nM	PMID[570928]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	19.52	mm	PMID[570928]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	12.5	uM	PMID[570928]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	25.0	uM	PMID[570928]

☑ 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 NPC47634 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	397
0.1-0.2	1580
0.2-0.3	3220
0.3-0.4	7095
0.4-0.5	10680
0.5-0.6	6226
0.6-0.7	5820
0.7-0.8	7268
0.8-0.85	330
0.85-0.9	32
0.9-0.95	29
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC75141
1.0	High Similarity	NPC55422
0.9874	High Similarity	NPC476146
0.9874	High Similarity	NPC158329
0.9874	High Similarity	NPC40089
0.9814	High Similarity	NPC476229
0.981	High Similarity	NPC189689
0.975	High Similarity	NPC476216
0.9747	High Similarity	NPC131578
0.9691	High Similarity	NPC476152
0.9689	High Similarity	NPC476196
0.9627	High Similarity	NPC41598
0.9571	High Similarity	NPC476139
0.9565	High Similarity	NPC223413
0.9557	High Similarity	NPC286422
0.9509	High Similarity	NPC476159
0.9398	High Similarity	NPC476199
0.9398	High Similarity	NPC476210
0.9317	High Similarity	NPC94796
0.9281	High Similarity	NPC233978
0.9277	High Similarity	NPC162248
0.9268	High Similarity	NPC63514
0.9264	High Similarity	NPC476255
0.9264	High Similarity	NPC476056
0.9217	High Similarity	NPC476311
0.9207	High Similarity	NPC193222
0.9193	High Similarity	NPC43490
0.9193	High Similarity	NPC475107
0.9152	High Similarity	NPC102810
0.9146	High Similarity	NPC62444
0.9114	High Similarity	NPC476162
0.9112	High Similarity	NPC473607
0.9107	High Similarity	NPC227275
0.9042	High Similarity	NPC169018
0.9024	High Similarity	NPC476931
0.9	High Similarity	NPC473729
0.8994	High Similarity	NPC98943
0.8951	High Similarity	NPC476930
0.8876	High Similarity	NPC475080
0.8824	High Similarity	NPC475398
0.8743	High Similarity	NPC473908
0.8706	High Similarity	NPC118128
0.8675	High Similarity	NPC476929
0.8667	High Similarity	NPC125969
0.8655	High Similarity	NPC17105
0.8655	High Similarity	NPC474276
0.8655	High Similarity	NPC73899
0.8655	High Similarity	NPC147363
0.8647	High Similarity	NPC193698
0.8623	High Similarity	NPC475106
0.8596	High Similarity	NPC477529
0.858	High Similarity	NPC475109
0.8563	High Similarity	NPC61382
0.8563	High Similarity	NPC103816
0.8555	High Similarity	NPC469345
0.8547	High Similarity	NPC469393
0.8529	High Similarity	NPC292233
0.8503	High Similarity	NPC172687
0.8503	High Similarity	NPC243701
0.8497	Intermediate Similarity	NPC98667
0.8497	Intermediate Similarity	NPC294149
0.8497	Intermediate Similarity	NPC232412
0.8497	Intermediate Similarity	NPC86809
0.8485	Intermediate Similarity	NPC469934
0.848	Intermediate Similarity	NPC54903
0.848	Intermediate Similarity	NPC207574
0.848	Intermediate Similarity	NPC291795
0.848	Intermediate Similarity	NPC297195
0.848	Intermediate Similarity	NPC286074
0.8471	Intermediate Similarity	NPC17274
0.8471	Intermediate Similarity	NPC85047
0.8471	Intermediate Similarity	NPC120857
0.8443	Intermediate Similarity	NPC311574
0.8443	Intermediate Similarity	NPC264932
0.8443	Intermediate Similarity	NPC474373
0.8434	Intermediate Similarity	NPC470352
0.8434	Intermediate Similarity	NPC470354
0.843	Intermediate Similarity	NPC251144
0.843	Intermediate Similarity	NPC241387
0.8427	Intermediate Similarity	NPC174486
0.8418	Intermediate Similarity	NPC106700
0.8385	Intermediate Similarity	NPC206212
0.8385	Intermediate Similarity	NPC71184
0.8383	Intermediate Similarity	NPC161650
0.8383	Intermediate Similarity	NPC210048
0.8383	Intermediate Similarity	NPC201127
0.8382	Intermediate Similarity	NPC472620
0.8372	Intermediate Similarity	NPC472619
0.8372	Intermediate Similarity	NPC20734
0.8364	Intermediate Similarity	NPC470353
0.8364	Intermediate Similarity	NPC288534
0.8363	Intermediate Similarity	NPC323137
0.8363	Intermediate Similarity	NPC469394
0.8362	Intermediate Similarity	NPC475656
0.8362	Intermediate Similarity	NPC475148
0.8354	Intermediate Similarity	NPC321387
0.8354	Intermediate Similarity	NPC150928
0.8354	Intermediate Similarity	NPC158866
0.8354	Intermediate Similarity	NPC327059
0.8353	Intermediate Similarity	NPC469395
0.8344	Intermediate Similarity	NPC211811
0.8333	Intermediate Similarity	NPC329678
0.8333	Intermediate Similarity	NPC470942
0.8333	Intermediate Similarity	NPC82534
0.8324	Intermediate Similarity	NPC282636
0.8324	Intermediate Similarity	NPC294863
0.8323	Intermediate Similarity	NPC56049
0.8323	Intermediate Similarity	NPC54830
0.8313	Intermediate Similarity	NPC470555
0.8313	Intermediate Similarity	NPC472799
0.8313	Intermediate Similarity	NPC471695
0.8305	Intermediate Similarity	NPC208069
0.8304	Intermediate Similarity	NPC204088
0.8304	Intermediate Similarity	NPC329215
0.8304	Intermediate Similarity	NPC259007
0.8302	Intermediate Similarity	NPC472343
0.8302	Intermediate Similarity	NPC19476
0.8302	Intermediate Similarity	NPC241975
0.8295	Intermediate Similarity	NPC477683
0.8295	Intermediate Similarity	NPC477682
0.8295	Intermediate Similarity	NPC5671
0.8294	Intermediate Similarity	NPC473022
0.8293	Intermediate Similarity	NPC469932
0.8282	Intermediate Similarity	NPC140120
0.8282	Intermediate Similarity	NPC474108
0.8282	Intermediate Similarity	NPC177995
0.8274	Intermediate Similarity	NPC474637
0.8268	Intermediate Similarity	NPC197972
0.8263	Intermediate Similarity	NPC476169
0.8263	Intermediate Similarity	NPC471456
0.8263	Intermediate Similarity	NPC275575
0.8261	Intermediate Similarity	NPC321629
0.8261	Intermediate Similarity	NPC323884
0.8261	Intermediate Similarity	NPC326193
0.8261	Intermediate Similarity	NPC204469
0.8261	Intermediate Similarity	NPC321148
0.8253	Intermediate Similarity	NPC142527
0.825	Intermediate Similarity	NPC221173
0.825	Intermediate Similarity	NPC469818
0.8249	Intermediate Similarity	NPC244903
0.8249	Intermediate Similarity	NPC121888
0.8242	Intermediate Similarity	NPC470908
0.8242	Intermediate Similarity	NPC476509
0.8242	Intermediate Similarity	NPC180351
0.8239	Intermediate Similarity	NPC312630
0.8239	Intermediate Similarity	NPC324220
0.8239	Intermediate Similarity	NPC219584
0.8239	Intermediate Similarity	NPC470083
0.8239	Intermediate Similarity	NPC183639
0.8239	Intermediate Similarity	NPC199458
0.8235	Intermediate Similarity	NPC117985
0.8235	Intermediate Similarity	NPC472346
0.8235	Intermediate Similarity	NPC92589
0.8232	Intermediate Similarity	NPC295436
0.8232	Intermediate Similarity	NPC37139
0.8232	Intermediate Similarity	NPC469933
0.8232	Intermediate Similarity	NPC208303
0.8232	Intermediate Similarity	NPC472345
0.8232	Intermediate Similarity	NPC161864
0.8229	Intermediate Similarity	NPC154986
0.8228	Intermediate Similarity	NPC470983
0.8228	Intermediate Similarity	NPC470982
0.8221	Intermediate Similarity	NPC473132
0.8221	Intermediate Similarity	NPC181388
0.8221	Intermediate Similarity	NPC473135
0.8221	Intermediate Similarity	NPC470676
0.8218	Intermediate Similarity	NPC313717
0.8218	Intermediate Similarity	NPC101107
0.8218	Intermediate Similarity	NPC315306
0.8214	Intermediate Similarity	NPC109967
0.8214	Intermediate Similarity	NPC192587
0.8214	Intermediate Similarity	NPC321372
0.8214	Intermediate Similarity	NPC475797
0.8214	Intermediate Similarity	NPC472050
0.8214	Intermediate Similarity	NPC474738
0.8214	Intermediate Similarity	NPC474609
0.8214	Intermediate Similarity	NPC78554
0.8214	Intermediate Similarity	NPC129053
0.8214	Intermediate Similarity	NPC469936
0.821	Intermediate Similarity	NPC5990
0.8208	Intermediate Similarity	NPC253730
0.8208	Intermediate Similarity	NPC471975
0.8208	Intermediate Similarity	NPC470374
0.8208	Intermediate Similarity	NPC126204
0.8208	Intermediate Similarity	NPC478060
0.8208	Intermediate Similarity	NPC470377
0.8208	Intermediate Similarity	NPC286230
0.8208	Intermediate Similarity	NPC76647
0.8208	Intermediate Similarity	NPC478059
0.8208	Intermediate Similarity	NPC472622
0.8208	Intermediate Similarity	NPC283041
0.8204	Intermediate Similarity	NPC311579
0.8204	Intermediate Similarity	NPC236756
0.8204	Intermediate Similarity	NPC209760
0.8204	Intermediate Similarity	NPC477669
0.8204	Intermediate Similarity	NPC192189
0.8204	Intermediate Similarity	NPC100134
0.8199	Intermediate Similarity	NPC316560
0.8199	Intermediate Similarity	NPC316911
0.8198	Intermediate Similarity	NPC314653

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 NPC47634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	963
0.2-0.3	1856
0.3-0.4	2673
0.4-0.5	1983
0.5-0.6	902
0.6-0.7	284
0.7-0.8	142
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8383	Intermediate Similarity	NPD7075	Discontinued
0.8204	Intermediate Similarity	NPD7819	Suspended
0.8204	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7411	Suspended
0.8057	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD2533	Approved
0.8049	Intermediate Similarity	NPD2532	Approved
0.8049	Intermediate Similarity	NPD2534	Approved
0.8049	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6801	Discontinued
0.7963	Intermediate Similarity	NPD2800	Approved
0.7953	Intermediate Similarity	NPD3749	Approved
0.7943	Intermediate Similarity	NPD7473	Discontinued
0.7939	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3882	Suspended
0.7836	Intermediate Similarity	NPD3817	Phase 2
0.7826	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7811	Intermediate Similarity	NPD4380	Phase 2
0.7805	Intermediate Similarity	NPD3750	Approved
0.7802	Intermediate Similarity	NPD8434	Phase 2
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.7771	Intermediate Similarity	NPD6799	Approved
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.7759	Intermediate Similarity	NPD5494	Approved
0.7722	Intermediate Similarity	NPD7251	Discontinued
0.7705	Intermediate Similarity	NPD8150	Discontinued
0.7701	Intermediate Similarity	NPD919	Approved
0.7701	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7768	Phase 2
0.7684	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6166	Phase 2
0.7684	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6797	Phase 2
0.7647	Intermediate Similarity	NPD3226	Approved
0.7644	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5403	Approved
0.763	Intermediate Similarity	NPD5402	Approved
0.7614	Intermediate Similarity	NPD6959	Discontinued
0.7614	Intermediate Similarity	NPD1247	Approved
0.7598	Intermediate Similarity	NPD3818	Discontinued
0.7593	Intermediate Similarity	NPD6651	Approved
0.7586	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1512	Approved
0.7572	Intermediate Similarity	NPD2801	Approved
0.7571	Intermediate Similarity	NPD5710	Approved
0.7571	Intermediate Similarity	NPD5711	Approved
0.7569	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7054	Approved
0.7556	Intermediate Similarity	NPD5844	Phase 1
0.7554	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1243	Approved
0.7527	Intermediate Similarity	NPD6559	Discontinued
0.7515	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD7472	Approved
0.7514	Intermediate Similarity	NPD1934	Approved
0.7514	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD3748	Approved
0.7471	Intermediate Similarity	NPD1465	Phase 2
0.747	Intermediate Similarity	NPD1549	Phase 2
0.7456	Intermediate Similarity	NPD1511	Approved
0.7446	Intermediate Similarity	NPD8313	Approved
0.7446	Intermediate Similarity	NPD8312	Approved
0.7433	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD920	Approved
0.7425	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2346	Discontinued
0.741	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1510	Phase 2
0.7394	Intermediate Similarity	NPD2799	Discontinued
0.7389	Intermediate Similarity	NPD2403	Approved
0.7382	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6099	Approved
0.7349	Intermediate Similarity	NPD6100	Approved
0.7349	Intermediate Similarity	NPD2796	Approved
0.7333	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD7435	Discontinued
0.7317	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5124	Phase 1
0.731	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3751	Discontinued
0.7294	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1607	Approved
0.7256	Intermediate Similarity	NPD1240	Approved
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7238	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1471	Phase 3
0.72	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7874	Approved
0.7189	Intermediate Similarity	NPD5953	Discontinued
0.7184	Intermediate Similarity	NPD8366	Approved
0.7179	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4287	Approved
0.7157	Intermediate Similarity	NPD7696	Phase 3
0.7157	Intermediate Similarity	NPD7697	Approved
0.7157	Intermediate Similarity	NPD7698	Approved
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD3268	Approved
0.7128	Intermediate Similarity	NPD8285	Discontinued
0.7126	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8319	Approved
0.7121	Intermediate Similarity	NPD7871	Phase 2
0.7121	Intermediate Similarity	NPD7870	Phase 2
0.7121	Intermediate Similarity	NPD8320	Phase 1
0.712	Intermediate Similarity	NPD7228	Approved
0.7112	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2344	Approved
0.7092	Intermediate Similarity	NPD6782	Approved
0.7092	Intermediate Similarity	NPD6776	Approved
0.7092	Intermediate Similarity	NPD6780	Approved
0.7092	Intermediate Similarity	NPD6779	Approved
0.7092	Intermediate Similarity	NPD6781	Approved
0.7092	Intermediate Similarity	NPD6778	Approved
0.7092	Intermediate Similarity	NPD6777	Approved
0.7088	Intermediate Similarity	NPD3787	Discontinued
0.7083	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.7076	Intermediate Similarity	NPD4628	Phase 3
0.7052	Intermediate Similarity	NPD7390	Discontinued
0.7048	Intermediate Similarity	NPD8491	Approved
0.7033	Intermediate Similarity	NPD7199	Phase 2
0.703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD37	Approved
0.7017	Intermediate Similarity	NPD6234	Discontinued
0.7015	Intermediate Similarity	NPD7701	Phase 2
0.7014	Intermediate Similarity	NPD8469	Approved
0.7011	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD447	Suspended
0.7	Intermediate Similarity	NPD4967	Phase 2
0.7	Intermediate Similarity	NPD4966	Approved
0.7	Intermediate Similarity	NPD4965	Approved
0.6995	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7229	Phase 3
0.6995	Remote Similarity	NPD7801	Approved
0.6995	Remote Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7699	Phase 2
0.699	Remote Similarity	NPD7700	Phase 2
0.6968	Remote Similarity	NPD7685	Pre-registration
0.6949	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4288	Approved
0.6941	Remote Similarity	NPD5405	Approved
0.6941	Remote Similarity	NPD5404	Approved
0.6941	Remote Similarity	NPD5406	Approved
0.6941	Remote Similarity	NPD5408	Approved
0.6938	Remote Similarity	NPD7907	Approved
0.6936	Remote Similarity	NPD2309	Approved
0.6928	Remote Similarity	NPD3764	Approved
0.6923	Remote Similarity	NPD6535	Approved
0.6923	Remote Similarity	NPD6534	Approved
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6585	Discontinued
0.6905	Remote Similarity	NPD6355	Discontinued
0.6882	Remote Similarity	NPD4308	Phase 3
0.6882	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7003	Approved
0.6878	Remote Similarity	NPD6765	Approved
0.6878	Remote Similarity	NPD6764	Approved
0.6875	Remote Similarity	NPD5049	Phase 3
0.6857	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9717	Approved
0.6848	Remote Similarity	NPD8127	Discontinued
0.6845	Remote Similarity	NPD4060	Phase 1
0.6845	Remote Similarity	NPD943	Approved
0.6845	Remote Similarity	NPD7799	Discontinued
0.6829	Remote Similarity	NPD3267	Approved
0.6829	Remote Similarity	NPD3266	Approved
0.6829	Remote Similarity	NPD2797	Approved
0.6829	Remote Similarity	NPD1203	Approved
0.6826	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4749	Approved
0.6807	Remote Similarity	NPD6832	Phase 2
0.6805	Remote Similarity	NPD230	Phase 1
0.6802	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7584	Approved
0.6796	Remote Similarity	NPD8455	Phase 2
0.6796	Remote Similarity	NPD5761	Phase 2
0.6796	Remote Similarity	NPD5760	Phase 2
0.6792	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.679	Remote Similarity	NPD422	Phase 1
0.6789	Remote Similarity	NPD7240	Approved
0.6788	Remote Similarity	NPD2798	Approved
0.6784	Remote Similarity	NPD7033	Discontinued
0.6782	Remote Similarity	NPD8166	Discontinued
0.6778	Remote Similarity	NPD5890	Approved
0.6778	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5889	Approved
0.6771	Remote Similarity	NPD8407	Phase 2
0.6766	Remote Similarity	NPD4625	Phase 3

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