NPASS Compound

Structure

NPC476244 OpenBabel07101718222D 29 32 0 0 1 0 0 0 0 0999 V2000 3.2608 3.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9850 -2.3048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6178 -4.3535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0896 -0.8954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3009 1.0594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8669 2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9035 2.3487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9401 -2.4163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -0.9633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5666 0.0469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1084 -1.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7836 -1.3573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1156 0.5790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9401 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -2.9006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6178 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1012 -0.9633 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6178 -2.4163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4184 0.5581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9475 0.2014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4318 -0.6375 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0278 1.4178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3414 1.0863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -3.8692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1862 -1.2450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9563 0.1541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5391 -1.1483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5391 -2.7156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 12 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 9 16 2 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 11 28 1 0 0 0 0 11 29 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 6 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 15 18 2 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 28 1 0 0 0 0 17 22 1 1 0 0 0 18 29 1 0 0 0 0 19 22 1 1 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 26 1 1 0 0 0 22 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	400.555
LogP:	2.686
LogD:	2.847
LogS:	-3.971
# Rotatable Bonds:	6
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	5.459
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.561
MDCK Permeability:	2.118169140885584e-05
Pgp-inhibitor:	0.09
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.175

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.575
Plasma Protein Binding (PPB):	84.02781677246094%
Volume Distribution (VD):	1.397
Pgp-substrate:	11.776191711425781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.204
CYP2D6-inhibitor:	0.499
CYP2D6-substrate:	0.426
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.805

ADMET: Excretion

Clearance (CL):	8.576
Half-life (T1/2):	0.38

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.121
AMES Toxicity:	0.233
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.764
Skin Sensitization:	0.41
Carcinogencity:	0.949
Eye Corrosion:	0.005
Eye Irritation:	0.018
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC476244

Natural Product ID:	NPC476244
*Common Name:**	Cinerin D
IUPAC Name:	(1R,4S,5S,6S,7R)-4-hydroxy-1,5-dimethoxy-6-(7-methoxy-1,3-benzodioxol-5-yl)-7-methyl-3-prop-2-enylbicyclo[3.2.1]oct-2-en-8-one
Synonyms:	Cinerin D
Standard InCHIKey:	XLIOFFLNGANYEP-RDKBRGHYSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-6-7-13-10-21(26-4)12(2)17(22(27-5,19(13)23)20(21)24)14-8-15(25-3)18-16(9-14)28-11-29-18/h6,8-10,12,17,19,23H,1,7,11H2,2-5H3/t12-,17+,19+,21+,22+/m1/s1
SMILES:	CC1C(C2(C(C(=CC1(C2=O)OC)CC=C)O)OC)C3=CC4=C(C(=C3)OC)OCO4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558110
PubChem CID:	45273291
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19548690]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27964	Nectandra amazonum	Species	Lauraceae	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	7
Others	11

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	5
Organism	9
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	188000.0	nM	PMID[542571]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	92100.0	nM	PMID[542571]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6600.0	nM	PMID[542570]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	GI	=	7.3	%	PMID[542570]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	GI	=	6.2	%	PMID[542570]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	GI	=	1.3	%	PMID[542570]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	17.0	%	PMID[542570]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	GI	<	30.0	%	PMID[542570]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	GI	<	30.0	%	PMID[542570]
NPT19	Organism	Escherichia coli	Escherichia coli	GI	<	30.0	%	PMID[542570]
NPT1117	Organism	Salmonella enterica subsp. enterica	Salmonella enterica subsp. enterica	GI	<	30.0	%	PMID[542570]
NPT2	Others	Unspecified		IC50	=	8840.0	nM	PMID[542571]
NPT2	Others	Unspecified		Ratio IC50	=	2.04	n.a.	PMID[542571]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6630.0	nM	PMID[542571]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25600.0	nM	PMID[542571]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	356000.0	nM	PMID[542571]

☑ 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 NPC476244 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	372
0.1-0.2	1402
0.2-0.3	3264
0.3-0.4	7488
0.4-0.5	10969
0.5-0.6	5771
0.6-0.7	9066
0.7-0.8	4251
0.8-0.85	93
0.85-0.9	15
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9557	High Similarity	NPC476277
0.9412	High Similarity	NPC28724
0.9241	High Similarity	NPC476337
0.9114	High Similarity	NPC476340
0.8987	High Similarity	NPC476363
0.8924	High Similarity	NPC476364
0.8797	High Similarity	NPC476335
0.8704	High Similarity	NPC472565
0.8698	High Similarity	NPC23593
0.8639	High Similarity	NPC107739
0.8608	High Similarity	NPC472567
0.8596	High Similarity	NPC236089
0.8589	High Similarity	NPC475095
0.8588	High Similarity	NPC263955
0.8538	High Similarity	NPC29587
0.85	High Similarity	NPC163002
0.8481	Intermediate Similarity	NPC476338
0.8481	Intermediate Similarity	NPC476359
0.8481	Intermediate Similarity	NPC476336
0.8452	Intermediate Similarity	NPC476334
0.8447	Intermediate Similarity	NPC56184
0.8438	Intermediate Similarity	NPC475170
0.8438	Intermediate Similarity	NPC177830
0.8418	Intermediate Similarity	NPC476362
0.8344	Intermediate Similarity	NPC136757
0.8313	Intermediate Similarity	NPC304821
0.8303	Intermediate Similarity	NPC220462
0.8302	Intermediate Similarity	NPC472560
0.8274	Intermediate Similarity	NPC469475
0.8274	Intermediate Similarity	NPC469518
0.8261	Intermediate Similarity	NPC477698
0.825	Intermediate Similarity	NPC25496
0.8242	Intermediate Similarity	NPC189730
0.8221	Intermediate Similarity	NPC477699
0.8214	Intermediate Similarity	NPC125991
0.821	Intermediate Similarity	NPC12854
0.8204	Intermediate Similarity	NPC310399
0.8204	Intermediate Similarity	NPC73422
0.8198	Intermediate Similarity	NPC271755
0.8198	Intermediate Similarity	NPC254071
0.8198	Intermediate Similarity	NPC149502
0.8198	Intermediate Similarity	NPC222665
0.8187	Intermediate Similarity	NPC474799
0.8182	Intermediate Similarity	NPC164152
0.8176	Intermediate Similarity	NPC15743
0.8171	Intermediate Similarity	NPC244903
0.8171	Intermediate Similarity	NPC245948
0.8171	Intermediate Similarity	NPC327225
0.8161	Intermediate Similarity	NPC156635
0.816	Intermediate Similarity	NPC234152
0.816	Intermediate Similarity	NPC164082
0.8155	Intermediate Similarity	NPC90336
0.8148	Intermediate Similarity	NPC145569
0.8148	Intermediate Similarity	NPC216223
0.8144	Intermediate Similarity	NPC209473
0.8144	Intermediate Similarity	NPC329743
0.8144	Intermediate Similarity	NPC179914
0.8133	Intermediate Similarity	NPC32373
0.8133	Intermediate Similarity	NPC237946
0.8129	Intermediate Similarity	NPC174191
0.8125	Intermediate Similarity	NPC474982
0.8121	Intermediate Similarity	NPC25127
0.8118	Intermediate Similarity	NPC475738
0.8113	Intermediate Similarity	NPC474966
0.811	Intermediate Similarity	NPC151425
0.8107	Intermediate Similarity	NPC469512
0.8101	Intermediate Similarity	NPC51681
0.8095	Intermediate Similarity	NPC91634
0.8095	Intermediate Similarity	NPC268718
0.8095	Intermediate Similarity	NPC150943
0.8092	Intermediate Similarity	NPC245452
0.8092	Intermediate Similarity	NPC469506
0.8084	Intermediate Similarity	NPC19947
0.8084	Intermediate Similarity	NPC474990
0.8084	Intermediate Similarity	NPC207584
0.8081	Intermediate Similarity	NPC476771
0.8072	Intermediate Similarity	NPC38699
0.807	Intermediate Similarity	NPC254306
0.807	Intermediate Similarity	NPC67037
0.807	Intermediate Similarity	NPC255615
0.807	Intermediate Similarity	NPC113093
0.807	Intermediate Similarity	NPC475621
0.8063	Intermediate Similarity	NPC27159
0.8063	Intermediate Similarity	NPC50696
0.8061	Intermediate Similarity	NPC473236
0.8059	Intermediate Similarity	NPC471286
0.8059	Intermediate Similarity	NPC472582
0.8059	Intermediate Similarity	NPC475865
0.805	Intermediate Similarity	NPC104956
0.8049	Intermediate Similarity	NPC62354
0.8049	Intermediate Similarity	NPC178048
0.8047	Intermediate Similarity	NPC288149
0.8038	Intermediate Similarity	NPC203351
0.8037	Intermediate Similarity	NPC477695
0.8037	Intermediate Similarity	NPC125570
0.8037	Intermediate Similarity	NPC174512
0.8037	Intermediate Similarity	NPC668
0.8037	Intermediate Similarity	NPC293757
0.8037	Intermediate Similarity	NPC474965
0.8036	Intermediate Similarity	NPC477410
0.8036	Intermediate Similarity	NPC76211
0.8035	Intermediate Similarity	NPC212748
0.8035	Intermediate Similarity	NPC72249
0.8025	Intermediate Similarity	NPC474039
0.8025	Intermediate Similarity	NPC30720
0.8024	Intermediate Similarity	NPC164244
0.8023	Intermediate Similarity	NPC42892
0.8023	Intermediate Similarity	NPC42230
0.8023	Intermediate Similarity	NPC48640
0.8023	Intermediate Similarity	NPC474948
0.8023	Intermediate Similarity	NPC283041
0.8023	Intermediate Similarity	NPC149244
0.8023	Intermediate Similarity	NPC471180
0.8012	Intermediate Similarity	NPC34531
0.8012	Intermediate Similarity	NPC287504
0.8011	Intermediate Similarity	NPC67302
0.8	Intermediate Similarity	NPC108202
0.8	Intermediate Similarity	NPC76687
0.8	Intermediate Similarity	NPC196937
0.8	Intermediate Similarity	NPC472564
0.8	Intermediate Similarity	NPC474808
0.8	Intermediate Similarity	NPC476011
0.7989	Intermediate Similarity	NPC223375
0.7989	Intermediate Similarity	NPC235575
0.7989	Intermediate Similarity	NPC471181
0.7989	Intermediate Similarity	NPC475825
0.7989	Intermediate Similarity	NPC261254
0.7989	Intermediate Similarity	NPC470685
0.7989	Intermediate Similarity	NPC476772
0.7988	Intermediate Similarity	NPC269906
0.7988	Intermediate Similarity	NPC96593
0.7988	Intermediate Similarity	NPC119910
0.7988	Intermediate Similarity	NPC474936
0.7987	Intermediate Similarity	NPC470991
0.7977	Intermediate Similarity	NPC223747
0.7977	Intermediate Similarity	NPC225434
0.7977	Intermediate Similarity	NPC203050
0.7977	Intermediate Similarity	NPC120099
0.7977	Intermediate Similarity	NPC52382
0.7977	Intermediate Similarity	NPC270578
0.7977	Intermediate Similarity	NPC219904
0.7976	Intermediate Similarity	NPC473395
0.7976	Intermediate Similarity	NPC286919
0.7976	Intermediate Similarity	NPC475663
0.7965	Intermediate Similarity	NPC20237
0.7964	Intermediate Similarity	NPC267242
0.7963	Intermediate Similarity	NPC212890
0.7963	Intermediate Similarity	NPC87295
0.7963	Intermediate Similarity	NPC212697
0.7963	Intermediate Similarity	NPC3982
0.7956	Intermediate Similarity	NPC71385
0.7956	Intermediate Similarity	NPC230670
0.7953	Intermediate Similarity	NPC14294
0.7953	Intermediate Similarity	NPC116759
0.7952	Intermediate Similarity	NPC474514
0.7952	Intermediate Similarity	NPC35544
0.7952	Intermediate Similarity	NPC104728
0.7944	Intermediate Similarity	NPC475360
0.7943	Intermediate Similarity	NPC474568
0.7941	Intermediate Similarity	NPC100465
0.7941	Intermediate Similarity	NPC295009
0.7941	Intermediate Similarity	NPC94155
0.7941	Intermediate Similarity	NPC260640
0.7941	Intermediate Similarity	NPC117985
0.7941	Intermediate Similarity	NPC152424
0.7939	Intermediate Similarity	NPC477700
0.7937	Intermediate Similarity	NPC287124
0.7937	Intermediate Similarity	NPC210354
0.7937	Intermediate Similarity	NPC176586
0.7931	Intermediate Similarity	NPC477883
0.7931	Intermediate Similarity	NPC206123
0.7931	Intermediate Similarity	NPC279209
0.7931	Intermediate Similarity	NPC102277
0.7929	Intermediate Similarity	NPC469384
0.7929	Intermediate Similarity	NPC215375
0.7929	Intermediate Similarity	NPC62518
0.7927	Intermediate Similarity	NPC474903
0.7925	Intermediate Similarity	NPC322021
0.7925	Intermediate Similarity	NPC470855
0.7925	Intermediate Similarity	NPC147379
0.7925	Intermediate Similarity	NPC177868
0.7921	Intermediate Similarity	NPC170203
0.7921	Intermediate Similarity	NPC6709
0.7919	Intermediate Similarity	NPC265530
0.7919	Intermediate Similarity	NPC76482
0.7919	Intermediate Similarity	NPC84362
0.7919	Intermediate Similarity	NPC150131
0.7919	Intermediate Similarity	NPC226304
0.7919	Intermediate Similarity	NPC173637
0.7919	Intermediate Similarity	NPC92565
0.7919	Intermediate Similarity	NPC223424
0.7919	Intermediate Similarity	NPC317489
0.7919	Intermediate Similarity	NPC160156
0.7919	Intermediate Similarity	NPC127546
0.7919	Intermediate Similarity	NPC52550
0.7919	Intermediate Similarity	NPC325555
0.7917	Intermediate Similarity	NPC155063
0.7917	Intermediate Similarity	NPC163635
0.7917	Intermediate Similarity	NPC478055
0.7914	Intermediate Similarity	NPC208507

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 NPC476244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	852
0.2-0.3	1996
0.3-0.4	2721
0.4-0.5	1897
0.5-0.6	983
0.6-0.7	329
0.7-0.8	49
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	NPD7184	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7199	Phase 2
0.8171	Intermediate Similarity	NPD37	Approved
0.8133	Intermediate Similarity	NPD4967	Phase 2
0.8133	Intermediate Similarity	NPD4966	Approved
0.8133	Intermediate Similarity	NPD4965	Approved
0.8036	Intermediate Similarity	NPD6234	Discontinued
0.7919	Intermediate Similarity	NPD3818	Discontinued
0.7865	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7028	Phase 2
0.7816	Intermediate Similarity	NPD7228	Approved
0.7811	Intermediate Similarity	NPD3882	Suspended
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7784	Intermediate Similarity	NPD6797	Phase 2
0.774	Intermediate Similarity	NPD7251	Discontinued
0.7727	Intermediate Similarity	NPD7074	Phase 3
0.7697	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7054	Approved
0.7647	Intermediate Similarity	NPD3817	Phase 2
0.764	Intermediate Similarity	NPD7685	Pre-registration
0.7633	Intermediate Similarity	NPD1934	Approved
0.7627	Intermediate Similarity	NPD7472	Approved
0.76	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6166	Phase 2
0.7588	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3787	Discontinued
0.7576	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7240	Approved
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.7471	Intermediate Similarity	NPD5494	Approved
0.7457	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6002	Phase 3
0.7423	Intermediate Similarity	NPD6004	Phase 3
0.7423	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6005	Phase 3
0.7384	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD2801	Approved
0.736	Intermediate Similarity	NPD7473	Discontinued
0.7356	Intermediate Similarity	NPD7075	Discontinued
0.7348	Intermediate Similarity	NPD6559	Discontinued
0.7326	Intermediate Similarity	NPD6801	Discontinued
0.7317	Intermediate Similarity	NPD5762	Approved
0.7317	Intermediate Similarity	NPD5763	Approved
0.7314	Intermediate Similarity	NPD919	Approved
0.731	Intermediate Similarity	NPD4380	Phase 2
0.7288	Intermediate Similarity	NPD6232	Discontinued
0.7278	Intermediate Similarity	NPD1512	Approved
0.7262	Intermediate Similarity	NPD6799	Approved
0.7232	Intermediate Similarity	NPD1247	Approved
0.7222	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6599	Discontinued
0.7182	Intermediate Similarity	NPD5844	Phase 1
0.7181	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6653	Approved
0.716	Intermediate Similarity	NPD1511	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7135	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7799	Discontinued
0.7118	Intermediate Similarity	NPD2532	Approved
0.7118	Intermediate Similarity	NPD2533	Approved
0.7118	Intermediate Similarity	NPD2534	Approved
0.7115	Intermediate Similarity	NPD3705	Approved
0.7107	Intermediate Similarity	NPD5647	Approved
0.7102	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1653	Approved
0.7086	Intermediate Similarity	NPD5761	Phase 2
0.7086	Intermediate Similarity	NPD5760	Phase 2
0.7066	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8434	Phase 2
0.7056	Intermediate Similarity	NPD3926	Phase 2
0.7055	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3620	Phase 2
0.7055	Intermediate Similarity	NPD1613	Approved
0.7055	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5402	Approved
0.7039	Intermediate Similarity	NPD8127	Discontinued
0.7037	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1357	Approved
0.7011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7680	Approved
0.6989	Remote Similarity	NPD7819	Suspended
0.6988	Remote Similarity	NPD1510	Phase 2
0.6988	Remote Similarity	NPD7033	Discontinued
0.6982	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4110	Phase 3
0.6973	Remote Similarity	NPD6765	Approved
0.6973	Remote Similarity	NPD6764	Approved
0.6951	Remote Similarity	NPD1240	Approved
0.6949	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6099	Approved
0.6946	Remote Similarity	NPD6100	Approved
0.6936	Remote Similarity	NPD5403	Approved
0.6923	Remote Similarity	NPD6674	Discontinued
0.6923	Remote Similarity	NPD2800	Approved
0.6919	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7296	Approved
0.6909	Remote Similarity	NPD230	Phase 1
0.6905	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4628	Phase 3
0.6882	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1607	Approved
0.6864	Remote Similarity	NPD1549	Phase 2
0.6848	Remote Similarity	NPD4060	Phase 1
0.6845	Remote Similarity	NPD2796	Approved
0.6837	Remote Similarity	NPD6781	Approved
0.6837	Remote Similarity	NPD6778	Approved
0.6837	Remote Similarity	NPD6782	Approved
0.6837	Remote Similarity	NPD6776	Approved
0.6837	Remote Similarity	NPD6780	Approved
0.6837	Remote Similarity	NPD6779	Approved
0.6837	Remote Similarity	NPD6777	Approved
0.6831	Remote Similarity	NPD2403	Approved
0.6829	Remote Similarity	NPD6798	Discontinued
0.6825	Remote Similarity	NPD6784	Approved
0.6825	Remote Similarity	NPD6785	Approved
0.6821	Remote Similarity	NPD5401	Approved
0.6818	Remote Similarity	NPD7435	Discontinued
0.6813	Remote Similarity	NPD7229	Phase 3
0.681	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8455	Phase 2
0.6792	Remote Similarity	NPD1091	Approved
0.679	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6233	Phase 2
0.6786	Remote Similarity	NPD651	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7411	Suspended
0.6778	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6651	Approved
0.6761	Remote Similarity	NPD7458	Discontinued
0.6758	Remote Similarity	NPD6959	Discontinued
0.6748	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD943	Approved
0.6747	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2935	Discontinued
0.6727	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD2494	Approved
0.6717	Remote Similarity	NPD2493	Approved
0.6708	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5735	Approved
0.6706	Remote Similarity	NPD7266	Discontinued
0.6705	Remote Similarity	NPD7236	Approved
0.6704	Remote Similarity	NPD1465	Phase 2
0.67	Remote Similarity	NPD4583	Approved
0.67	Remote Similarity	NPD4582	Approved
0.6684	Remote Similarity	NPD2974	Approved
0.6684	Remote Similarity	NPD2975	Approved
0.6684	Remote Similarity	NPD2973	Approved
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD4580	Approved
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD5353	Approved
0.6667	Remote Similarity	NPD5958	Discontinued
0.665	Remote Similarity	NPD7698	Approved
0.665	Remote Similarity	NPD7696	Phase 3
0.665	Remote Similarity	NPD7930	Approved
0.665	Remote Similarity	NPD4004	Approved
0.665	Remote Similarity	NPD7697	Approved
0.665	Remote Similarity	NPD4002	Approved
0.6648	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD920	Approved
0.6647	Remote Similarity	NPD4140	Approved
0.6646	Remote Similarity	NPD2861	Phase 2
0.6646	Remote Similarity	NPD3018	Phase 2
0.6646	Remote Similarity	NPD9494	Approved
0.6646	Remote Similarity	NPD1608	Approved
0.6645	Remote Similarity	NPD5283	Phase 1
0.6633	Remote Similarity	NPD3450	Approved
0.6633	Remote Similarity	NPD3452	Approved
0.6632	Remote Similarity	NPD8312	Approved
0.6632	Remote Similarity	NPD8313	Approved
0.663	Remote Similarity	NPD5710	Approved
0.663	Remote Similarity	NPD5711	Approved
0.6629	Remote Similarity	NPD3146	Approved
0.6629	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6362	Approved
0.6626	Remote Similarity	NPD3094	Phase 2
0.6618	Remote Similarity	NPD7874	Approved
0.6618	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7871	Phase 2
0.6617	Remote Similarity	NPD7870	Phase 2
0.6615	Remote Similarity	NPD8150	Discontinued
0.6609	Remote Similarity	NPD5058	Phase 3
0.6607	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD447	Suspended
0.6607	Remote Similarity	NPD5124	Phase 1
0.6606	Remote Similarity	NPD4908	Phase 1
0.6605	Remote Similarity	NPD2982	Phase 2
0.6605	Remote Similarity	NPD4749	Approved
0.6605	Remote Similarity	NPD2983	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data