NPASS Compound

Structure

CID249171 OpenBabel06191716052D 30 33 0 0 1 0 0 0 0 0999 V2000 3.4159 3.3156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7059 -0.9404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7020 1.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0449 2.8529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7247 1.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0850 2.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5126 0.0407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7885 0.7791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7058 1.6472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8626 2.2773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6053 0.4611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1928 0.7738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9224 1.2791 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0299 1.9998 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1793 0.6100 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5805 -0.1991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8734 0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7360 2.7643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7019 2.0257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0449 2.9997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7618 1.9739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2497 -0.9422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 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 5.5860 -0.3036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 8 2 0 0 0 0 3 9 2 0 0 0 0 4 7 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 22 1 0 0 0 0 7 10 1 0 0 0 0 8 12 1 0 0 0 0 9 20 1 0 0 0 0 10 5 1 1 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 11 23 1 1 0 0 0 12 28 1 1 0 0 0 13 6 1 6 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 8 1 1 0 0 0 14 19 1 0 0 0 0 15 9 1 1 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 21 1 0 0 0 0 18 26 1 1 0 0 0 19 30 1 6 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 28 1 6 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.17
Volume:	406.113
LogP:	-0.561
LogD:	0.263
LogS:	-1.607
# Rotatable Bonds:	3
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.214
Synthetic Accessibility Score:	5.197
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.222
MDCK Permeability:	7.656853995285928e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.757
20% Bioavailability (F20%):	0.413
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	57.657981872558594%
Volume Distribution (VD):	0.439
Pgp-substrate:	42.95006561279297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.316
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	1.479
Half-life (T1/2):	0.7

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.903
Drug-inuced Liver Injury (DILI):	0.622
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.081
Carcinogencity:	0.131
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC249171

Natural Product ID:	NPC249171
*Common Name:**	8-Epidesacylcynaropicrin Glucoside
IUPAC Name:	(3aR,4R,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	XNFZJASXPNFCQW-CEJIZLNCSA-N
Standard InCHI:	InChI=1S/C21H28O9/c1-7-4-11(23)15-9(3)20(27)30-19(15)14-8(2)12(5-10(7)14)28-21-18(26)17(25)16(24)13(6-22)29-21/h10-19,21-26H,1-6H2/t10-,11+,12-,13+,14-,15+,16+,17-,18+,19+,21+/m0/s1
SMILES:	C=C1C[C@H]([C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@H](C[C@@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622761
PubChem CID:	21636138
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90113-8]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987049]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17567070]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	seed	n.a.	PMID[21280632]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21648406]
NPO32813	ixeris dentata	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[26341134]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13	Chamaecrista mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9352	Senecio peltiferus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO372	Kallstroemia tribuloides	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13	Chamaecrista mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5855	Scutellaria repens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	19.8	uM	PMID[453303]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	17.6	uM	PMID[453303]
NPT27	Others	Unspecified		Activity	=	103.5	%	PMID[453303]
NPT27	Others	Unspecified		Activity	=	103.3	%	PMID[453303]

☑ 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 NPC249171 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	250
0.1-0.2	1652
0.2-0.3	6184
0.3-0.4	13174
0.4-0.5	9737
0.5-0.6	7318
0.6-0.7	3927
0.7-0.8	389
0.8-0.85	54
0.85-0.9	0
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC49833
0.9681	High Similarity	NPC80144
0.9674	High Similarity	NPC236580
0.9674	High Similarity	NPC304445
0.9579	High Similarity	NPC473148
0.9368	High Similarity	NPC67296
0.9355	High Similarity	NPC474297
0.9247	High Similarity	NPC167893
0.9053	High Similarity	NPC263674
0.9053	High Similarity	NPC58267
0.9053	High Similarity	NPC261372
0.8788	High Similarity	NPC475928
0.8614	High Similarity	NPC170432
0.8602	High Similarity	NPC217983
0.8602	High Similarity	NPC207114
0.8587	High Similarity	NPC187661
0.8571	High Similarity	NPC472015
0.8529	High Similarity	NPC148270
0.8529	High Similarity	NPC197813
0.8529	High Similarity	NPC80338
0.8511	High Similarity	NPC38392
0.85	High Similarity	NPC4899
0.85	High Similarity	NPC474730
0.85	High Similarity	NPC106668
0.85	High Similarity	NPC35185
0.85	High Similarity	NPC177013
0.8485	Intermediate Similarity	NPC473146
0.8469	Intermediate Similarity	NPC474313
0.8469	Intermediate Similarity	NPC471150
0.8454	Intermediate Similarity	NPC472873
0.8421	Intermediate Similarity	NPC54065
0.8421	Intermediate Similarity	NPC19087
0.8421	Intermediate Similarity	NPC297474
0.8416	Intermediate Similarity	NPC27687
0.8416	Intermediate Similarity	NPC37240
0.837	Intermediate Similarity	NPC194859
0.837	Intermediate Similarity	NPC224386
0.8367	Intermediate Similarity	NPC161293
0.8333	Intermediate Similarity	NPC35959
0.8333	Intermediate Similarity	NPC171360
0.8333	Intermediate Similarity	NPC29821
0.8333	Intermediate Similarity	NPC184063
0.8333	Intermediate Similarity	NPC133888
0.8333	Intermediate Similarity	NPC57304
0.8333	Intermediate Similarity	NPC63193
0.8333	Intermediate Similarity	NPC293001
0.8316	Intermediate Similarity	NPC215556
0.8316	Intermediate Similarity	NPC155935
0.8286	Intermediate Similarity	NPC193741
0.8269	Intermediate Similarity	NPC110701
0.8252	Intermediate Similarity	NPC127235
0.8229	Intermediate Similarity	NPC216284
0.8229	Intermediate Similarity	NPC206614
0.8229	Intermediate Similarity	NPC35809
0.8229	Intermediate Similarity	NPC474323
0.8218	Intermediate Similarity	NPC287539
0.8218	Intermediate Similarity	NPC3488
0.8211	Intermediate Similarity	NPC79549
0.82	Intermediate Similarity	NPC37866
0.8191	Intermediate Similarity	NPC304558
0.8182	Intermediate Similarity	NPC306041
0.8152	Intermediate Similarity	NPC246076
0.8144	Intermediate Similarity	NPC475925
0.8131	Intermediate Similarity	NPC475924
0.8131	Intermediate Similarity	NPC475851
0.8119	Intermediate Similarity	NPC186861
0.8119	Intermediate Similarity	NPC471381
0.81	Intermediate Similarity	NPC311904
0.8065	Intermediate Similarity	NPC128246
0.8061	Intermediate Similarity	NPC475788
0.8021	Intermediate Similarity	NPC471149
0.8021	Intermediate Similarity	NPC470009
0.802	Intermediate Similarity	NPC45125
0.8	Intermediate Similarity	NPC476009
0.8	Intermediate Similarity	NPC91771
0.8	Intermediate Similarity	NPC142529
0.8	Intermediate Similarity	NPC24956
0.8	Intermediate Similarity	NPC54731
0.8	Intermediate Similarity	NPC56593
0.8	Intermediate Similarity	NPC18019
0.7959	Intermediate Similarity	NPC235051
0.7959	Intermediate Similarity	NPC155215
0.7938	Intermediate Similarity	NPC92974
0.7938	Intermediate Similarity	NPC283409
0.7921	Intermediate Similarity	NPC472290
0.7921	Intermediate Similarity	NPC181151
0.7917	Intermediate Similarity	NPC118601
0.7917	Intermediate Similarity	NPC186148
0.7917	Intermediate Similarity	NPC24728
0.7917	Intermediate Similarity	NPC190753
0.7905	Intermediate Similarity	NPC44004
0.7905	Intermediate Similarity	NPC54737
0.79	Intermediate Similarity	NPC476053
0.79	Intermediate Similarity	NPC93869
0.79	Intermediate Similarity	NPC6765
0.79	Intermediate Similarity	NPC163228
0.79	Intermediate Similarity	NPC213698
0.7895	Intermediate Similarity	NPC284534
0.7895	Intermediate Similarity	NPC204105
0.7895	Intermediate Similarity	NPC300082
0.7879	Intermediate Similarity	NPC258216
0.7872	Intermediate Similarity	NPC111409
0.7864	Intermediate Similarity	NPC150923
0.785	Intermediate Similarity	NPC139838
0.785	Intermediate Similarity	NPC59489
0.7849	Intermediate Similarity	NPC126248
0.7835	Intermediate Similarity	NPC177629
0.7835	Intermediate Similarity	NPC58219
0.7835	Intermediate Similarity	NPC178875
0.7812	Intermediate Similarity	NPC64153
0.7812	Intermediate Similarity	NPC162071
0.7812	Intermediate Similarity	NPC236692
0.7812	Intermediate Similarity	NPC309757
0.781	Intermediate Similarity	NPC474917
0.78	Intermediate Similarity	NPC127019
0.78	Intermediate Similarity	NPC63897
0.78	Intermediate Similarity	NPC473331
0.78	Intermediate Similarity	NPC198853
0.78	Intermediate Similarity	NPC274588
0.7788	Intermediate Similarity	NPC261117
0.7788	Intermediate Similarity	NPC86077
0.7788	Intermediate Similarity	NPC310804
0.7788	Intermediate Similarity	NPC250545
0.7778	Intermediate Similarity	NPC131209
0.7778	Intermediate Similarity	NPC133698
0.7767	Intermediate Similarity	NPC70865
0.7757	Intermediate Similarity	NPC475960
0.7757	Intermediate Similarity	NPC68248
0.7755	Intermediate Similarity	NPC472872
0.7748	Intermediate Similarity	NPC277583
0.7745	Intermediate Similarity	NPC161493
0.7723	Intermediate Similarity	NPC52044
0.7723	Intermediate Similarity	NPC67584
0.7723	Intermediate Similarity	NPC170120
0.7723	Intermediate Similarity	NPC475900
0.77	Intermediate Similarity	NPC473263
0.77	Intermediate Similarity	NPC473273
0.77	Intermediate Similarity	NPC60386
0.77	Intermediate Similarity	NPC472874
0.77	Intermediate Similarity	NPC473234
0.77	Intermediate Similarity	NPC200237
0.77	Intermediate Similarity	NPC308656
0.7692	Intermediate Similarity	NPC473332
0.7692	Intermediate Similarity	NPC171759
0.7684	Intermediate Similarity	NPC245665
0.767	Intermediate Similarity	NPC187268
0.7664	Intermediate Similarity	NPC26617
0.7647	Intermediate Similarity	NPC213078
0.7647	Intermediate Similarity	NPC170527
0.7629	Intermediate Similarity	NPC475019
0.7629	Intermediate Similarity	NPC474949
0.7629	Intermediate Similarity	NPC470242
0.7629	Intermediate Similarity	NPC474762
0.7629	Intermediate Similarity	NPC476015
0.7624	Intermediate Similarity	NPC190294
0.7624	Intermediate Similarity	NPC477131
0.7624	Intermediate Similarity	NPC470013
0.7624	Intermediate Similarity	NPC323008
0.7624	Intermediate Similarity	NPC71589
0.7624	Intermediate Similarity	NPC262133
0.7624	Intermediate Similarity	NPC470010
0.7619	Intermediate Similarity	NPC304163
0.76	Intermediate Similarity	NPC472197
0.76	Intermediate Similarity	NPC12172
0.76	Intermediate Similarity	NPC286341
0.76	Intermediate Similarity	NPC184463
0.76	Intermediate Similarity	NPC208886
0.76	Intermediate Similarity	NPC191339
0.7593	Intermediate Similarity	NPC392
0.7593	Intermediate Similarity	NPC177524
0.7593	Intermediate Similarity	NPC219900
0.7576	Intermediate Similarity	NPC12872
0.7576	Intermediate Similarity	NPC168679
0.7573	Intermediate Similarity	NPC476613
0.7573	Intermediate Similarity	NPC476612
0.7573	Intermediate Similarity	NPC474182
0.757	Intermediate Similarity	NPC243998
0.757	Intermediate Similarity	NPC41681
0.757	Intermediate Similarity	NPC223450
0.7565	Intermediate Similarity	NPC473228
0.7565	Intermediate Similarity	NPC470829
0.7551	Intermediate Similarity	NPC475773
0.7549	Intermediate Similarity	NPC36954
0.7549	Intermediate Similarity	NPC471141
0.7549	Intermediate Similarity	NPC304886
0.7526	Intermediate Similarity	NPC329749
0.7525	Intermediate Similarity	NPC320089
0.7525	Intermediate Similarity	NPC81419
0.7525	Intermediate Similarity	NPC238090
0.7525	Intermediate Similarity	NPC475912
0.7525	Intermediate Similarity	NPC472195
0.7525	Intermediate Similarity	NPC212486
0.7525	Intermediate Similarity	NPC179746
0.7525	Intermediate Similarity	NPC472196
0.7525	Intermediate Similarity	NPC153590
0.7525	Intermediate Similarity	NPC476300
0.7524	Intermediate Similarity	NPC28304
0.7524	Intermediate Similarity	NPC298255
0.7524	Intermediate Similarity	NPC216911
0.75	Intermediate Similarity	NPC231710

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 NPC249171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	2291
0.2-0.3	3967
0.3-0.4	1780
0.4-0.5	506
0.5-0.6	271
0.6-0.7	60
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7664	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6686	Approved
0.7327	Intermediate Similarity	NPD46	Approved
0.7327	Intermediate Similarity	NPD6698	Approved
0.7257	Intermediate Similarity	NPD8133	Approved
0.7228	Intermediate Similarity	NPD1695	Approved
0.708	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6412	Phase 2
0.7025	Intermediate Similarity	NPD7507	Approved
0.6991	Remote Similarity	NPD6371	Approved
0.6887	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7319	Approved
0.6852	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8517	Approved
0.6833	Remote Similarity	NPD8515	Approved
0.6833	Remote Similarity	NPD8516	Approved
0.6833	Remote Similarity	NPD8513	Phase 3
0.6723	Remote Similarity	NPD7327	Approved
0.6723	Remote Similarity	NPD7328	Approved
0.6694	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6612	Remote Similarity	NPD8377	Approved
0.6612	Remote Similarity	NPD8294	Approved
0.6602	Remote Similarity	NPD4249	Approved
0.6581	Remote Similarity	NPD6053	Discontinued
0.6557	Remote Similarity	NPD8335	Approved
0.6557	Remote Similarity	NPD8379	Approved
0.6557	Remote Similarity	NPD8378	Approved
0.6557	Remote Similarity	NPD7503	Approved
0.6557	Remote Similarity	NPD8296	Approved
0.6557	Remote Similarity	NPD8380	Approved
0.6538	Remote Similarity	NPD4250	Approved
0.6538	Remote Similarity	NPD4251	Approved
0.6505	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7983	Approved
0.6446	Remote Similarity	NPD7641	Discontinued
0.6423	Remote Similarity	NPD8269	Approved
0.6423	Remote Similarity	NPD8266	Approved
0.6423	Remote Similarity	NPD8268	Approved
0.6423	Remote Similarity	NPD8267	Approved
0.6404	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4225	Approved
0.6378	Remote Similarity	NPD7736	Approved
0.6371	Remote Similarity	NPD6370	Approved
0.6355	Remote Similarity	NPD5785	Approved
0.6346	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5282	Discontinued
0.632	Remote Similarity	NPD7642	Approved
0.632	Remote Similarity	NPD7830	Approved
0.632	Remote Similarity	NPD7829	Approved
0.6311	Remote Similarity	NPD5362	Discontinued
0.6299	Remote Similarity	NPD8074	Phase 3
0.6299	Remote Similarity	NPD8293	Discontinued
0.627	Remote Similarity	NPD7492	Approved
0.6261	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7638	Approved
0.623	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8451	Approved
0.622	Remote Similarity	NPD6616	Approved
0.6214	Remote Similarity	NPD6435	Approved
0.621	Remote Similarity	NPD6054	Approved
0.6195	Remote Similarity	NPD7639	Approved
0.6195	Remote Similarity	NPD7640	Approved
0.619	Remote Similarity	NPD8328	Phase 3
0.619	Remote Similarity	NPD5363	Approved
0.6176	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD8448	Approved
0.6172	Remote Similarity	NPD7078	Approved
0.616	Remote Similarity	NPD8444	Approved
0.616	Remote Similarity	NPD6016	Approved
0.616	Remote Similarity	NPD6015	Approved
0.6154	Remote Similarity	NPD7154	Phase 3
0.614	Remote Similarity	NPD5344	Discontinued
0.6139	Remote Similarity	NPD4238	Approved
0.6139	Remote Similarity	NPD4802	Phase 2
0.6119	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5369	Approved
0.6111	Remote Similarity	NPD5988	Approved
0.6102	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6009	Approved
0.6098	Remote Similarity	NPD7115	Discovery
0.608	Remote Similarity	NPD6319	Approved
0.608	Remote Similarity	NPD6059	Approved
0.6071	Remote Similarity	NPD7839	Suspended
0.6063	Remote Similarity	NPD6067	Discontinued
0.6058	Remote Similarity	NPD4269	Approved
0.6058	Remote Similarity	NPD4270	Approved
0.605	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6882	Approved
0.6031	Remote Similarity	NPD8392	Approved
0.6031	Remote Similarity	NPD8390	Approved
0.6031	Remote Similarity	NPD8391	Approved
0.6019	Remote Similarity	NPD5368	Approved
0.6019	Remote Similarity	NPD4819	Approved
0.6019	Remote Similarity	NPD4820	Approved
0.6019	Remote Similarity	NPD4822	Approved
0.6019	Remote Similarity	NPD4821	Approved
0.6016	Remote Similarity	NPD8342	Approved
0.6016	Remote Similarity	NPD8341	Approved
0.6016	Remote Similarity	NPD8340	Approved
0.6016	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8337	Approved
0.6	Remote Similarity	NPD8336	Approved
0.6	Remote Similarity	NPD3669	Approved
0.6	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD4632	Approved
0.5984	Remote Similarity	NPD8080	Discontinued
0.5981	Remote Similarity	NPD5786	Approved
0.598	Remote Similarity	NPD4271	Approved
0.598	Remote Similarity	NPD4268	Approved
0.5962	Remote Similarity	NPD4790	Discontinued
0.5946	Remote Similarity	NPD5778	Approved
0.5946	Remote Similarity	NPD5779	Approved
0.5946	Remote Similarity	NPD6399	Phase 3
0.594	Remote Similarity	NPD6845	Suspended
0.5932	Remote Similarity	NPD6008	Approved
0.5906	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8297	Approved
0.5865	Remote Similarity	NPD7260	Phase 2
0.5865	Remote Similarity	NPD4252	Approved
0.5856	Remote Similarity	NPD8034	Phase 2
0.5856	Remote Similarity	NPD8035	Phase 2
0.5849	Remote Similarity	NPD5332	Approved
0.5849	Remote Similarity	NPD5331	Approved
0.5846	Remote Similarity	NPD8273	Phase 1
0.5821	Remote Similarity	NPD8338	Approved
0.582	Remote Similarity	NPD6649	Approved
0.582	Remote Similarity	NPD6650	Approved
0.5818	Remote Similarity	NPD6101	Approved
0.5818	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7632	Discontinued
0.5812	Remote Similarity	NPD8086	Approved
0.5812	Remote Similarity	NPD8139	Approved
0.5812	Remote Similarity	NPD8085	Approved
0.5812	Remote Similarity	NPD8138	Approved
0.5812	Remote Similarity	NPD8082	Approved
0.5812	Remote Similarity	NPD8084	Approved
0.5812	Remote Similarity	NPD8083	Approved
0.581	Remote Similarity	NPD1779	Approved
0.581	Remote Similarity	NPD1780	Approved
0.5804	Remote Similarity	NPD8171	Discontinued
0.5794	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5956	Approved
0.5785	Remote Similarity	NPD6372	Approved
0.5785	Remote Similarity	NPD6373	Approved
0.5776	Remote Similarity	NPD6648	Approved
0.5773	Remote Similarity	NPD898	Approved
0.5773	Remote Similarity	NPD897	Approved
0.5773	Remote Similarity	NPD896	Approved
0.5763	Remote Similarity	NPD8275	Approved
0.5763	Remote Similarity	NPD8276	Approved
0.5755	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.575	Remote Similarity	NPD5697	Approved
0.575	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD1694	Approved
0.5739	Remote Similarity	NPD6084	Phase 2
0.5739	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD7637	Suspended
0.5714	Remote Similarity	NPD8081	Approved
0.5702	Remote Similarity	NPD7320	Approved
0.5702	Remote Similarity	NPD6881	Approved
0.5702	Remote Similarity	NPD6899	Approved
0.5702	Remote Similarity	NPD5695	Phase 3
0.569	Remote Similarity	NPD5696	Approved
0.5673	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6402	Approved
0.5667	Remote Similarity	NPD8393	Approved
0.5667	Remote Similarity	NPD6675	Approved
0.5667	Remote Similarity	NPD5739	Approved
0.5667	Remote Similarity	NPD7128	Approved
0.5659	Remote Similarity	NPD6921	Approved
0.5659	Remote Similarity	NPD5983	Phase 2
0.5656	Remote Similarity	NPD6012	Approved
0.5656	Remote Similarity	NPD6013	Approved
0.5656	Remote Similarity	NPD6014	Approved
0.5639	Remote Similarity	NPD6033	Approved
0.5636	Remote Similarity	NPD7524	Approved
0.562	Remote Similarity	NPD5701	Approved
0.561	Remote Similarity	NPD7290	Approved
0.561	Remote Similarity	NPD6883	Approved
0.561	Remote Similarity	NPD7102	Approved
0.56	Remote Similarity	NPD7532	Clinical (unspecified phase)

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