NPASS Compound

Structure

NPC206815 OpenBabel07101718202D 37 41 0 0 1 0 0 0 0 0999 V2000 -7.2235 1.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1943 3.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2891 0.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2672 0.8600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6146 3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9290 2.3463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8108 1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4062 0.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6199 1.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5762 1.8111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9071 2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9448 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6146 1.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9448 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0787 3.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2127 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6418 1.1873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2127 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6768 2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9349 0.0982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8108 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0787 4.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3467 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3328 0.2363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5544 2.0190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2161 3.5053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0787 1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9727 1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3467 1.8917 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 31 1 0 0 0 0 2 32 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 6 33 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 25 1 0 0 0 0 9 26 1 0 0 0 0 10 21 1 0 0 0 0 11 5 1 6 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 13 2 0 0 0 0 12 31 1 0 0 0 0 13 32 1 0 0 0 0 14 8 1 1 0 0 0 14 16 1 0 0 0 0 14 34 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 6 0 0 0 16 17 1 0 0 0 0 16 27 1 6 0 0 0 17 18 1 0 0 0 0 17 28 1 1 0 0 0 18 23 1 0 0 0 0 18 29 1 6 0 0 0 19 20 1 0 0 0 0 19 35 1 1 0 0 0 20 24 1 6 0 0 0 20 37 1 0 0 0 0 21 30 2 0 0 0 0 21 35 1 0 0 0 0 22 33 1 0 0 0 0 22 36 1 1 0 0 0 23 34 1 0 0 0 0 23 36 1 1 0 0 0 24 9 1 6 0 0 0 24 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.17
Volume:	481.968
LogP:	0.586
LogD:	0.301
LogS:	-3.221
# Rotatable Bonds:	9
TPSA:	186.13
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.191
Synthetic Accessibility Score:	4.847
Fsp3:	0.625
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:	-6.256
MDCK Permeability:	0.00010173639020649716
Pgp-inhibitor:	0.013
Pgp-substrate:	0.586
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.194
Plasma Protein Binding (PPB):	30.394214630126953%
Volume Distribution (VD):	0.451
Pgp-substrate:	26.1862850189209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.3
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.5
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	4.45
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.415
Drug-inuced Liver Injury (DILI):	0.632
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.058
Carcinogencity:	0.334
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC206815

Natural Product ID:	NPC206815
*Common Name:**	6-O-Veratroylcatalpol
IUPAC Name:	[(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] 3,4-dimethoxybenzoate
Synonyms:	6-O-Veratroyl Catalpol
Standard InCHIKey:	JPLOCWOFCUFHBG-PIAIVMLOSA-N
Standard InCHI:	InChI=1S/C24H30O13/c1-31-12-4-3-10(7-13(12)32-2)21(30)35-19-11-5-6-33-22(15(11)24(9-26)20(19)37-24)36-23-18(29)17(28)16(27)14(8-25)34-23/h3-7,11,14-20,22-23,25-29H,8-9H2,1-2H3/t11-,14-,15-,16-,17+,18-,19+,20+,22+,23+,24-/m1/s1
SMILES:	COc1ccc(cc1OC)C(=O)O[C@H]1[C@@H]2C=CO[C@H]([C@@H]2[C@]2(CO)[C@H]1O2)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2059078
PubChem CID:	185862
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33328	cresentia alata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26351040]
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	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	1
Others	8

Activity Type	# Activity
Individual Protein	8
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	38.2	%	PMID[510609]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	38.6	%	PMID[510609]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	39.1	%	PMID[510609]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<=	30.0	%	PMID[510609]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	97.7	%	PMID[510610]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	107.1	%	PMID[510610]
NPT35	Others	n.a.		IC50	>	100000.0	nM	PMID[510611]

☑ 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 NPC206815 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	359
0.1-0.2	1428
0.2-0.3	3172
0.3-0.4	7036
0.4-0.5	10509
0.5-0.6	7267
0.6-0.7	9257
0.7-0.8	3504
0.8-0.85	123
0.85-0.9	30
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC130730
0.9808	High Similarity	NPC301910
0.974	High Similarity	NPC474936
0.9615	High Similarity	NPC476011
0.9542	High Similarity	NPC478232
0.9487	High Similarity	NPC138993
0.9434	High Similarity	NPC282551
0.9202	High Similarity	NPC470685
0.9161	High Similarity	NPC194705
0.9103	High Similarity	NPC89693
0.9103	High Similarity	NPC478241
0.9103	High Similarity	NPC229548
0.908	High Similarity	NPC21956
0.9057	High Similarity	NPC179914
0.9032	High Similarity	NPC147224
0.9026	High Similarity	NPC308178
0.8974	High Similarity	NPC475379
0.8968	High Similarity	NPC478236
0.8968	High Similarity	NPC478234
0.8889	High Similarity	NPC478240
0.8868	High Similarity	NPC475484
0.8861	High Similarity	NPC229354
0.8854	High Similarity	NPC289021
0.8854	High Similarity	NPC158546
0.8854	High Similarity	NPC269914
0.8854	High Similarity	NPC478249
0.8839	High Similarity	NPC473149
0.8834	High Similarity	NPC109990
0.8812	High Similarity	NPC478248
0.8797	High Similarity	NPC203664
0.8797	High Similarity	NPC36130
0.8797	High Similarity	NPC134905
0.878	High Similarity	NPC180586
0.8773	High Similarity	NPC145847
0.8765	High Similarity	NPC478265
0.8758	High Similarity	NPC226759
0.8742	High Similarity	NPC137813
0.8718	High Similarity	NPC18789
0.8696	High Similarity	NPC475378
0.8688	High Similarity	NPC327032
0.8688	High Similarity	NPC194095
0.8688	High Similarity	NPC191046
0.8671	High Similarity	NPC227980
0.8671	High Similarity	NPC240592
0.8671	High Similarity	NPC117346
0.8654	High Similarity	NPC474234
0.8642	High Similarity	NPC286919
0.8642	High Similarity	NPC187205
0.8642	High Similarity	NPC475663
0.8634	High Similarity	NPC10205
0.8613	High Similarity	NPC96194
0.8613	High Similarity	NPC299855
0.8608	High Similarity	NPC96599
0.8608	High Similarity	NPC111785
0.8589	High Similarity	NPC469384
0.8581	High Similarity	NPC116104
0.8581	High Similarity	NPC88754
0.8581	High Similarity	NPC302286
0.8581	High Similarity	NPC237872
0.8581	High Similarity	NPC263397
0.858	High Similarity	NPC471405
0.8563	High Similarity	NPC189704
0.8562	High Similarity	NPC478235
0.8545	High Similarity	NPC41009
0.8535	High Similarity	NPC473867
0.8528	High Similarity	NPC472860
0.8528	High Similarity	NPC133984
0.8526	High Similarity	NPC473281
0.8526	High Similarity	NPC77922
0.8514	High Similarity	NPC476067
0.8514	High Similarity	NPC475121
0.8476	Intermediate Similarity	NPC160780
0.8476	Intermediate Similarity	NPC289811
0.8466	Intermediate Similarity	NPC478266
0.8462	Intermediate Similarity	NPC242756
0.8462	Intermediate Similarity	NPC475213
0.8462	Intermediate Similarity	NPC152796
0.8457	Intermediate Similarity	NPC476364
0.8452	Intermediate Similarity	NPC46644
0.8447	Intermediate Similarity	NPC289438
0.8438	Intermediate Similarity	NPC205054
0.8424	Intermediate Similarity	NPC203020
0.8424	Intermediate Similarity	NPC239966
0.8418	Intermediate Similarity	NPC37838
0.8415	Intermediate Similarity	NPC1913
0.8395	Intermediate Similarity	NPC157898
0.8395	Intermediate Similarity	NPC310661
0.8395	Intermediate Similarity	NPC105827
0.8391	Intermediate Similarity	NPC473776
0.8391	Intermediate Similarity	NPC473205
0.8375	Intermediate Similarity	NPC478242
0.8373	Intermediate Similarity	NPC472859
0.8373	Intermediate Similarity	NPC311803
0.8373	Intermediate Similarity	NPC25389
0.8371	Intermediate Similarity	NPC475299
0.8364	Intermediate Similarity	NPC76211
0.8363	Intermediate Similarity	NPC195972
0.8362	Intermediate Similarity	NPC230670
0.8362	Intermediate Similarity	NPC71385
0.8333	Intermediate Similarity	NPC80098
0.8323	Intermediate Similarity	NPC158635
0.8323	Intermediate Similarity	NPC33298
0.8323	Intermediate Similarity	NPC229882
0.8323	Intermediate Similarity	NPC49597
0.8323	Intermediate Similarity	NPC285108
0.8315	Intermediate Similarity	NPC112708
0.8314	Intermediate Similarity	NPC469438
0.8313	Intermediate Similarity	NPC476337
0.8313	Intermediate Similarity	NPC166277
0.8313	Intermediate Similarity	NPC119125
0.8303	Intermediate Similarity	NPC104275
0.8303	Intermediate Similarity	NPC49173
0.8303	Intermediate Similarity	NPC4747
0.8293	Intermediate Similarity	NPC156624
0.8293	Intermediate Similarity	NPC172920
0.8291	Intermediate Similarity	NPC202391
0.8291	Intermediate Similarity	NPC296659
0.8291	Intermediate Similarity	NPC184464
0.8291	Intermediate Similarity	NPC251062
0.8284	Intermediate Similarity	NPC476277
0.8282	Intermediate Similarity	NPC44730
0.8274	Intermediate Similarity	NPC100420
0.8268	Intermediate Similarity	NPC473711
0.8261	Intermediate Similarity	NPC476394
0.8261	Intermediate Similarity	NPC98809
0.8256	Intermediate Similarity	NPC316539
0.8253	Intermediate Similarity	NPC287872
0.8253	Intermediate Similarity	NPC74319
0.825	Intermediate Similarity	NPC476359
0.825	Intermediate Similarity	NPC476338
0.8232	Intermediate Similarity	NPC472128
0.8232	Intermediate Similarity	NPC472127
0.8228	Intermediate Similarity	NPC186296
0.8225	Intermediate Similarity	NPC475738
0.8221	Intermediate Similarity	NPC267091
0.8217	Intermediate Similarity	NPC159387
0.8217	Intermediate Similarity	NPC7518
0.8217	Intermediate Similarity	NPC137501
0.8217	Intermediate Similarity	NPC154262
0.821	Intermediate Similarity	NPC69367
0.8208	Intermediate Similarity	NPC84482
0.8208	Intermediate Similarity	NPC107739
0.8208	Intermediate Similarity	NPC469354
0.8208	Intermediate Similarity	NPC169645
0.8205	Intermediate Similarity	NPC31745
0.8205	Intermediate Similarity	NPC220936
0.8204	Intermediate Similarity	NPC289346
0.8204	Intermediate Similarity	NPC239818
0.8204	Intermediate Similarity	NPC218471
0.8199	Intermediate Similarity	NPC472969
0.8182	Intermediate Similarity	NPC38699
0.8176	Intermediate Similarity	NPC473090
0.8171	Intermediate Similarity	NPC61604
0.8171	Intermediate Similarity	NPC299706
0.8171	Intermediate Similarity	NPC115466
0.8171	Intermediate Similarity	NPC308555
0.8171	Intermediate Similarity	NPC245615
0.8166	Intermediate Similarity	NPC120012
0.8161	Intermediate Similarity	NPC23593
0.816	Intermediate Similarity	NPC140151
0.816	Intermediate Similarity	NPC474620
0.816	Intermediate Similarity	NPC243891
0.8148	Intermediate Similarity	NPC92117
0.8148	Intermediate Similarity	NPC161955
0.8137	Intermediate Similarity	NPC153620
0.8137	Intermediate Similarity	NPC24257
0.8133	Intermediate Similarity	NPC163635
0.8129	Intermediate Similarity	NPC208818
0.8129	Intermediate Similarity	NPC116745
0.8125	Intermediate Similarity	NPC188217
0.8125	Intermediate Similarity	NPC108455
0.8118	Intermediate Similarity	NPC472130
0.8118	Intermediate Similarity	NPC472131
0.811	Intermediate Similarity	NPC476335
0.811	Intermediate Similarity	NPC228662
0.8107	Intermediate Similarity	NPC90905
0.8107	Intermediate Similarity	NPC246024
0.8107	Intermediate Similarity	NPC148273
0.8107	Intermediate Similarity	NPC4013
0.8101	Intermediate Similarity	NPC79908
0.8098	Intermediate Similarity	NPC473091
0.8089	Intermediate Similarity	NPC226005
0.8086	Intermediate Similarity	NPC120621
0.8086	Intermediate Similarity	NPC248257
0.8084	Intermediate Similarity	NPC223335
0.8084	Intermediate Similarity	NPC476340
0.8084	Intermediate Similarity	NPC40920
0.8081	Intermediate Similarity	NPC658
0.8081	Intermediate Similarity	NPC197708
0.8079	Intermediate Similarity	NPC186746
0.8077	Intermediate Similarity	NPC157554
0.8077	Intermediate Similarity	NPC37468
0.8075	Intermediate Similarity	NPC119773
0.8075	Intermediate Similarity	NPC98356
0.8075	Intermediate Similarity	NPC30890
0.8075	Intermediate Similarity	NPC475539
0.8075	Intermediate Similarity	NPC474268
0.8075	Intermediate Similarity	NPC291153
0.8075	Intermediate Similarity	NPC143246
0.8072	Intermediate Similarity	NPC145425

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 NPC206815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	843
0.2-0.3	1913
0.3-0.4	2651
0.4-0.5	2083
0.5-0.6	995
0.6-0.7	325
0.7-0.8	46
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9503	High Similarity	NPD7685	Pre-registration
0.7919	Intermediate Similarity	NPD3818	Discontinued
0.7865	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7199	Phase 2
0.7797	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7054	Approved
0.7758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7472	Approved
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD37	Approved
0.7627	Intermediate Similarity	NPD7074	Phase 3
0.7605	Intermediate Similarity	NPD1653	Approved
0.7602	Intermediate Similarity	NPD4967	Phase 2
0.7602	Intermediate Similarity	NPD4965	Approved
0.7602	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4966	Approved
0.7598	Intermediate Similarity	NPD7808	Phase 3
0.7584	Intermediate Similarity	NPD6797	Phase 2
0.7561	Intermediate Similarity	NPD6190	Approved
0.7558	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD3817	Phase 2
0.7542	Intermediate Similarity	NPD7251	Discontinued
0.7531	Intermediate Similarity	NPD7266	Discontinued
0.7514	Intermediate Similarity	NPD7228	Approved
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7438	Intermediate Similarity	NPD230	Phase 1
0.7429	Intermediate Similarity	NPD8127	Discontinued
0.7412	Intermediate Similarity	NPD7028	Phase 2
0.7374	Intermediate Similarity	NPD5844	Phase 1
0.7348	Intermediate Similarity	NPD7240	Approved
0.7341	Intermediate Similarity	NPD5353	Approved
0.7326	Intermediate Similarity	NPD1934	Approved
0.7284	Intermediate Similarity	NPD6653	Approved
0.7283	Intermediate Similarity	NPD2801	Approved
0.7278	Intermediate Similarity	NPD6273	Approved
0.7278	Intermediate Similarity	NPD9494	Approved
0.7273	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6559	Discontinued
0.7209	Intermediate Similarity	NPD4380	Phase 2
0.7207	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6166	Phase 2
0.7207	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3882	Suspended
0.7198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6232	Discontinued
0.7184	Intermediate Similarity	NPD8455	Phase 2
0.7184	Intermediate Similarity	NPD1465	Phase 2
0.7184	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8313	Approved
0.7174	Intermediate Similarity	NPD8312	Approved
0.7168	Intermediate Similarity	NPD6385	Approved
0.7168	Intermediate Similarity	NPD6386	Approved
0.7167	Intermediate Similarity	NPD7473	Discontinued
0.7166	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7799	Discontinued
0.7127	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD447	Suspended
0.7117	Intermediate Similarity	NPD1933	Approved
0.7095	Intermediate Similarity	NPD3787	Discontinued
0.7092	Intermediate Similarity	NPD7999	Approved
0.7086	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7819	Suspended
0.7083	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4110	Phase 3
0.7066	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7075	Discontinued
0.7052	Intermediate Similarity	NPD7458	Discontinued
0.7045	Intermediate Similarity	NPD5402	Approved
0.7029	Intermediate Similarity	NPD6801	Discontinued
0.7018	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3705	Approved
0.7006	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6005	Phase 3
0.7006	Intermediate Similarity	NPD6002	Phase 3
0.7006	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD5647	Approved
0.699	Remote Similarity	NPD7497	Discontinued
0.6989	Remote Similarity	NPD5761	Phase 2
0.6989	Remote Similarity	NPD5760	Phase 2
0.6982	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7930	Approved
0.6968	Remote Similarity	NPD9545	Approved
0.6968	Remote Similarity	NPD8434	Phase 2
0.6961	Remote Similarity	NPD5242	Approved
0.6959	Remote Similarity	NPD6799	Approved
0.6959	Remote Similarity	NPD1511	Approved
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6674	Discontinued
0.6909	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD5762	Approved
0.6905	Remote Similarity	NPD5763	Approved
0.6904	Remote Similarity	NPD7435	Discontinued
0.6894	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7033	Discontinued
0.6882	Remote Similarity	NPD6764	Approved
0.6882	Remote Similarity	NPD6765	Approved
0.6879	Remote Similarity	NPD1512	Approved
0.6855	Remote Similarity	NPD1608	Approved
0.6854	Remote Similarity	NPD5977	Approved
0.6854	Remote Similarity	NPD5978	Approved
0.6848	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5403	Approved
0.6837	Remote Similarity	NPD6781	Approved
0.6837	Remote Similarity	NPD6778	Approved
0.6837	Remote Similarity	NPD6782	Approved
0.6837	Remote Similarity	NPD6777	Approved
0.6837	Remote Similarity	NPD6776	Approved
0.6837	Remote Similarity	NPD6780	Approved
0.6837	Remote Similarity	NPD6779	Approved
0.6833	Remote Similarity	NPD919	Approved
0.6832	Remote Similarity	NPD6362	Approved
0.6829	Remote Similarity	NPD3764	Approved
0.6826	Remote Similarity	NPD7097	Phase 1
0.6821	Remote Similarity	NPD5401	Approved
0.6821	Remote Similarity	NPD2533	Approved
0.6821	Remote Similarity	NPD2534	Approved
0.6821	Remote Similarity	NPD2532	Approved
0.6818	Remote Similarity	NPD6599	Discontinued
0.6815	Remote Similarity	NPD1357	Approved
0.6813	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7236	Approved
0.6792	Remote Similarity	NPD1091	Approved
0.6791	Remote Similarity	NPD7038	Approved
0.6791	Remote Similarity	NPD7039	Approved
0.6788	Remote Similarity	NPD6233	Phase 2
0.6786	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7411	Suspended
0.6768	Remote Similarity	NPD3027	Phase 3
0.675	Remote Similarity	NPD9269	Phase 2
0.6747	Remote Similarity	NPD4140	Approved
0.6747	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3620	Phase 2
0.6746	Remote Similarity	NPD2935	Discontinued
0.6746	Remote Similarity	NPD2796	Approved
0.6737	Remote Similarity	NPD6784	Approved
0.6737	Remote Similarity	NPD6785	Approved
0.6736	Remote Similarity	NPD7296	Approved
0.6734	Remote Similarity	NPD7680	Approved
0.6733	Remote Similarity	NPD8151	Discontinued
0.6727	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD9268	Approved
0.6705	Remote Similarity	NPD7239	Suspended
0.6702	Remote Similarity	NPD8150	Discontinued
0.67	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7874	Approved
0.6688	Remote Similarity	NPD5536	Phase 2
0.6687	Remote Similarity	NPD2798	Approved
0.6686	Remote Similarity	NPD1510	Phase 2
0.6686	Remote Similarity	NPD3750	Approved
0.6686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2799	Discontinued
0.6685	Remote Similarity	NPD3926	Phase 2
0.6684	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4420	Approved
0.665	Remote Similarity	NPD7698	Approved
0.665	Remote Similarity	NPD7696	Phase 3
0.665	Remote Similarity	NPD7697	Approved
0.6647	Remote Similarity	NPD2438	Suspended
0.6635	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7583	Approved
0.6629	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3146	Approved
0.6629	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD1652	Phase 2
0.6627	Remote Similarity	NPD6798	Discontinued
0.6617	Remote Similarity	NPD7871	Phase 2
0.6617	Remote Similarity	NPD8320	Phase 1
0.6617	Remote Similarity	NPD8319	Approved
0.6617	Remote Similarity	NPD7870	Phase 2
0.6608	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2346	Discontinued
0.6607	Remote Similarity	NPD5735	Approved
0.6601	Remote Similarity	NPD7701	Phase 2
0.6601	Remote Similarity	NPD7585	Approved
0.66	Remote Similarity	NPD6823	Phase 2
0.6593	Remote Similarity	NPD3749	Approved
0.6591	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.659	Remote Similarity	NPD8166	Discontinued
0.6588	Remote Similarity	NPD3748	Approved
0.6585	Remote Similarity	NPD7801	Approved
0.6582	Remote Similarity	NPD6535	Approved
0.6582	Remote Similarity	NPD6534	Approved
0.6573	Remote Similarity	NPD3455	Phase 2
0.657	Remote Similarity	NPD2424	Discontinued
0.6566	Remote Similarity	NPD7095	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