NPASS Compound

Structure

NPC476363 OpenBabel07101719152D 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 0 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 1 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 0 0 0 0 19 23 2 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 6 0 0 0 22 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.15
Volume:	397.919
LogP:	3.047
LogD:	2.893
LogS:	-4.28
# Rotatable Bonds:	6
TPSA:	80.29
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	5.294
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.528
MDCK Permeability:	2.1731777451350354e-05
Pgp-inhibitor:	0.478
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.758
30% Bioavailability (F30%):	0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.934
Plasma Protein Binding (PPB):	83.82516479492188%
Volume Distribution (VD):	1.241
Pgp-substrate:	6.058459758758545%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.988
CYP2C19-inhibitor:	0.334
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.751
CYP2D6-substrate:	0.24
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	10.879
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.581
Drug-inuced Liver Injury (DILI):	0.177
AMES Toxicity:	0.305
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.399
Skin Sensitization:	0.391
Carcinogencity:	0.896
Eye Corrosion:	0.006
Eye Irritation:	0.023
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC476363

Natural Product ID:	NPC476363
*Common Name:**	Cinerin A
IUPAC Name:	(1S,5S,6S,7R)-1,5-dimethoxy-6-(7-methoxy-1,3-benzodioxol-5-yl)-7-methyl-3-prop-2-enylbicyclo[3.2.1]oct-2-ene-4,8-dione
Synonyms:	Cinerin A
Standard InCHIKey:	JRFQBNCUNXLLQL-SLFNRPLXSA-N
Standard InCHI:	InChI=1S/C22H24O7/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/h6,8-10,12,17H,1,7,11H2,2-5H3/t12-,17+,21-,22+/m1/s1
SMILES:	CC1C(C2(C(=O)C(=CC1(C2=O)OC)CC=C)OC)C3=CC4=C(C(=C3)OC)OCO4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL585723
PubChem CID:	45487088
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	=	165000.0	nM	PMID[529386]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	288000.0	nM	PMID[529386]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16800.0	nM	PMID[529385]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	GI	=	8.1	%	PMID[529385]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	GI	=	7.2	%	PMID[529385]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	GI	=	2.5	%	PMID[529385]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	6.7	%	PMID[529385]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	GI	<	30.0	%	PMID[529385]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	GI	<	30.0	%	PMID[529385]
NPT19	Organism	Escherichia coli	Escherichia coli	GI	<	30.0	%	PMID[529385]
NPT1117	Organism	Salmonella enterica subsp. enterica	Salmonella enterica subsp. enterica	GI	<	30.0	%	PMID[529385]
NPT2	Others	Unspecified		IC50	=	45600.0	nM	PMID[529386]
NPT2	Others	Unspecified		Ratio IC50	=	0.573	n.a.	PMID[529386]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16800.0	nM	PMID[529386]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	75600.0	nM	PMID[529386]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	88900.0	nM	PMID[529386]

☑ 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 NPC476363 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	479
0.1-0.2	1634
0.2-0.3	3710
0.3-0.4	9308
0.4-0.5	9789
0.5-0.6	5252
0.6-0.7	10292
0.7-0.8	2152
0.8-0.85	60
0.85-0.9	14
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC476362
0.9329	High Similarity	NPC472567
0.9299	High Similarity	NPC476277
0.9205	High Similarity	NPC163002
0.8987	High Similarity	NPC476244
0.8981	High Similarity	NPC476337
0.8854	High Similarity	NPC476340
0.8797	High Similarity	NPC472565
0.8766	High Similarity	NPC475170
0.8675	High Similarity	NPC472564
0.8662	High Similarity	NPC476364
0.8571	High Similarity	NPC25496
0.8535	High Similarity	NPC28724
0.8535	High Similarity	NPC476335
0.8526	High Similarity	NPC177830
0.8497	Intermediate Similarity	NPC15743
0.8497	Intermediate Similarity	NPC50696
0.8447	Intermediate Similarity	NPC475095
0.8442	Intermediate Similarity	NPC474158
0.8431	Intermediate Similarity	NPC474966
0.8421	Intermediate Similarity	NPC51681
0.8344	Intermediate Similarity	NPC166184
0.8312	Intermediate Similarity	NPC474288
0.8302	Intermediate Similarity	NPC220577
0.8272	Intermediate Similarity	NPC474990
0.8269	Intermediate Similarity	NPC472560
0.8267	Intermediate Similarity	NPC145769
0.8261	Intermediate Similarity	NPC188962
0.8261	Intermediate Similarity	NPC202249
0.8261	Intermediate Similarity	NPC42871
0.8258	Intermediate Similarity	NPC475000
0.8247	Intermediate Similarity	NPC176586
0.8247	Intermediate Similarity	NPC210354
0.8235	Intermediate Similarity	NPC278076
0.8217	Intermediate Similarity	NPC476338
0.8217	Intermediate Similarity	NPC476359
0.8217	Intermediate Similarity	NPC476336
0.8204	Intermediate Similarity	NPC474948
0.8204	Intermediate Similarity	NPC42230
0.8182	Intermediate Similarity	NPC302741
0.8165	Intermediate Similarity	NPC262804
0.8165	Intermediate Similarity	NPC40654
0.8163	Intermediate Similarity	NPC64948
0.816	Intermediate Similarity	NPC310206
0.8153	Intermediate Similarity	NPC193779
0.8153	Intermediate Similarity	NPC224687
0.8153	Intermediate Similarity	NPC474446
0.8153	Intermediate Similarity	NPC296575
0.8153	Intermediate Similarity	NPC87295
0.8148	Intermediate Similarity	NPC284353
0.8141	Intermediate Similarity	NPC177644
0.8141	Intermediate Similarity	NPC191158
0.8137	Intermediate Similarity	NPC308555
0.8129	Intermediate Similarity	NPC151423
0.8129	Intermediate Similarity	NPC46180
0.8129	Intermediate Similarity	NPC40237
0.8118	Intermediate Similarity	NPC474568
0.8086	Intermediate Similarity	NPC279930
0.8086	Intermediate Similarity	NPC478213
0.8084	Intermediate Similarity	NPC187923
0.8084	Intermediate Similarity	NPC475953
0.8075	Intermediate Similarity	NPC104353
0.8052	Intermediate Similarity	NPC470962
0.8049	Intermediate Similarity	NPC220462
0.8037	Intermediate Similarity	NPC478238
0.8037	Intermediate Similarity	NPC3273
0.8025	Intermediate Similarity	NPC218841
0.8025	Intermediate Similarity	NPC148497
0.8025	Intermediate Similarity	NPC92693
0.8025	Intermediate Similarity	NPC153008
0.8012	Intermediate Similarity	NPC239890
0.8012	Intermediate Similarity	NPC209411
0.8012	Intermediate Similarity	NPC474975
0.8	Intermediate Similarity	NPC238405
0.8	Intermediate Similarity	NPC470855
0.8	Intermediate Similarity	NPC325122
0.8	Intermediate Similarity	NPC125713
0.8	Intermediate Similarity	NPC477705
0.8	Intermediate Similarity	NPC477694
0.8	Intermediate Similarity	NPC339621
0.8	Intermediate Similarity	NPC104459
0.8	Intermediate Similarity	NPC280399
0.8	Intermediate Similarity	NPC257914
0.8	Intermediate Similarity	NPC233961
0.7988	Intermediate Similarity	NPC477380
0.7987	Intermediate Similarity	NPC153620
0.7987	Intermediate Similarity	NPC24257
0.7987	Intermediate Similarity	NPC104024
0.7987	Intermediate Similarity	NPC80230
0.7987	Intermediate Similarity	NPC304687
0.7987	Intermediate Similarity	NPC101755
0.7987	Intermediate Similarity	NPC65574
0.7976	Intermediate Similarity	NPC474647
0.7975	Intermediate Similarity	NPC232883
0.7975	Intermediate Similarity	NPC348849
0.7975	Intermediate Similarity	NPC57211
0.7975	Intermediate Similarity	NPC178195
0.7975	Intermediate Similarity	NPC273578
0.7974	Intermediate Similarity	NPC211386
0.7974	Intermediate Similarity	NPC38101
0.7965	Intermediate Similarity	NPC107739
0.7964	Intermediate Similarity	NPC76687
0.7963	Intermediate Similarity	NPC474414
0.7963	Intermediate Similarity	NPC279061
0.7962	Intermediate Similarity	NPC28326
0.7962	Intermediate Similarity	NPC125134
0.7962	Intermediate Similarity	NPC86455
0.7962	Intermediate Similarity	NPC137920
0.7953	Intermediate Similarity	NPC470685
0.7952	Intermediate Similarity	NPC139876
0.7952	Intermediate Similarity	NPC131557
0.7952	Intermediate Similarity	NPC474936
0.795	Intermediate Similarity	NPC12854
0.7947	Intermediate Similarity	NPC477706
0.7939	Intermediate Similarity	NPC477885
0.7939	Intermediate Similarity	NPC258644
0.7937	Intermediate Similarity	NPC117463
0.7927	Intermediate Similarity	NPC117154
0.7927	Intermediate Similarity	NPC254163
0.7925	Intermediate Similarity	NPC189054
0.7919	Intermediate Similarity	NPC263955
0.7919	Intermediate Similarity	NPC23593
0.7917	Intermediate Similarity	NPC475865
0.7914	Intermediate Similarity	NPC68882
0.7914	Intermediate Similarity	NPC144162
0.7914	Intermediate Similarity	NPC52623
0.7904	Intermediate Similarity	NPC34376
0.7901	Intermediate Similarity	NPC62354
0.7901	Intermediate Similarity	NPC210642
0.7901	Intermediate Similarity	NPC13985
0.7901	Intermediate Similarity	NPC477700
0.7901	Intermediate Similarity	NPC234152
0.7901	Intermediate Similarity	NPC32079
0.7895	Intermediate Similarity	NPC153453
0.7892	Intermediate Similarity	NPC179914
0.7892	Intermediate Similarity	NPC15764
0.7892	Intermediate Similarity	NPC68619
0.7892	Intermediate Similarity	NPC113055
0.7888	Intermediate Similarity	NPC145569
0.7888	Intermediate Similarity	NPC262455
0.7888	Intermediate Similarity	NPC477698
0.7888	Intermediate Similarity	NPC216223
0.7888	Intermediate Similarity	NPC177476
0.7879	Intermediate Similarity	NPC155063
0.7875	Intermediate Similarity	NPC30720
0.7874	Intermediate Similarity	NPC29587
0.7866	Intermediate Similarity	NPC244371
0.7857	Intermediate Similarity	NPC206815
0.7857	Intermediate Similarity	NPC469512
0.7857	Intermediate Similarity	NPC273021
0.7857	Intermediate Similarity	NPC72796
0.7857	Intermediate Similarity	NPC18284
0.7857	Intermediate Similarity	NPC44245
0.7857	Intermediate Similarity	NPC478199
0.7857	Intermediate Similarity	NPC61141
0.7857	Intermediate Similarity	NPC476011
0.7853	Intermediate Similarity	NPC151425
0.7853	Intermediate Similarity	NPC56184
0.7844	Intermediate Similarity	NPC474770
0.7844	Intermediate Similarity	NPC269906
0.7843	Intermediate Similarity	NPC136750
0.7843	Intermediate Similarity	NPC266848
0.784	Intermediate Similarity	NPC149505
0.7834	Intermediate Similarity	NPC28398
0.7829	Intermediate Similarity	NPC192255
0.7829	Intermediate Similarity	NPC236089
0.7826	Intermediate Similarity	NPC304821
0.7824	Intermediate Similarity	NPC113093
0.7823	Intermediate Similarity	NPC256167
0.7821	Intermediate Similarity	NPC178290
0.7816	Intermediate Similarity	NPC156635
0.7812	Intermediate Similarity	NPC213482
0.7806	Intermediate Similarity	NPC143895
0.7806	Intermediate Similarity	NPC209229
0.7806	Intermediate Similarity	NPC11453
0.7805	Intermediate Similarity	NPC292460
0.7805	Intermediate Similarity	NPC327225
0.7803	Intermediate Similarity	NPC62640
0.78	Intermediate Similarity	NPC286683
0.7799	Intermediate Similarity	NPC46880
0.7798	Intermediate Similarity	NPC94155
0.7798	Intermediate Similarity	NPC309335
0.7798	Intermediate Similarity	NPC109238
0.7798	Intermediate Similarity	NPC99968
0.7798	Intermediate Similarity	NPC296540
0.7792	Intermediate Similarity	NPC37065
0.7791	Intermediate Similarity	NPC303519
0.7791	Intermediate Similarity	NPC164082
0.7784	Intermediate Similarity	NPC250076
0.7784	Intermediate Similarity	NPC215375
0.7784	Intermediate Similarity	NPC62518
0.7784	Intermediate Similarity	NPC76211
0.7778	Intermediate Similarity	NPC668
0.7778	Intermediate Similarity	NPC72046
0.7778	Intermediate Similarity	NPC261812
0.7778	Intermediate Similarity	NPC477695
0.7778	Intermediate Similarity	NPC474965
0.7778	Intermediate Similarity	NPC65183
0.7778	Intermediate Similarity	NPC293757
0.7778	Intermediate Similarity	NPC174512

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 NPC476363 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	914
0.2-0.3	1943
0.3-0.4	2874
0.4-0.5	1868
0.5-0.6	825
0.6-0.7	303
0.7-0.8	26
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
0.8165	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7028	Phase 2
0.7798	Intermediate Similarity	NPD7199	Phase 2
0.7727	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD37	Approved
0.7665	Intermediate Similarity	NPD4966	Approved
0.7665	Intermediate Similarity	NPD4965	Approved
0.7665	Intermediate Similarity	NPD4967	Phase 2
0.764	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5494	Approved
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.756	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7485	Intermediate Similarity	NPD1247	Approved
0.7471	Intermediate Similarity	NPD3818	Discontinued
0.7471	Intermediate Similarity	NPD919	Approved
0.7396	Intermediate Similarity	NPD3817	Phase 2
0.7285	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD7228	Approved
0.7216	Intermediate Similarity	NPD7473	Discontinued
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.7167	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7808	Phase 3
0.7151	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7135	Intermediate Similarity	NPD2801	Approved
0.7111	Intermediate Similarity	NPD7251	Discontinued
0.7111	Intermediate Similarity	NPD7240	Approved
0.7108	Intermediate Similarity	NPD6799	Approved
0.7102	Intermediate Similarity	NPD5242	Approved
0.7095	Intermediate Similarity	NPD7074	Phase 3
0.7093	Intermediate Similarity	NPD5353	Approved
0.7079	Intermediate Similarity	NPD3751	Discontinued
0.7076	Intermediate Similarity	NPD1934	Approved
0.7062	Intermediate Similarity	NPD2403	Approved
0.7059	Intermediate Similarity	NPD6599	Discontinued
0.7039	Intermediate Similarity	NPD7054	Approved
0.7035	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1876	Approved
0.7	Intermediate Similarity	NPD7472	Approved
0.6988	Remote Similarity	NPD6190	Approved
0.6966	Remote Similarity	NPD6166	Phase 2
0.6966	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD230	Phase 1
0.6954	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3787	Discontinued
0.6944	Remote Similarity	NPD5844	Phase 1
0.6944	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1512	Approved
0.6918	Remote Similarity	NPD3027	Phase 3
0.6914	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7075	Discontinued
0.6913	Remote Similarity	NPD5283	Phase 1
0.6902	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5978	Approved
0.6897	Remote Similarity	NPD5977	Approved
0.6893	Remote Similarity	NPD8127	Discontinued
0.689	Remote Similarity	NPD2796	Approved
0.6882	Remote Similarity	NPD920	Approved
0.6879	Remote Similarity	NPD6801	Discontinued
0.6875	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2800	Approved
0.6864	Remote Similarity	NPD2533	Approved
0.6864	Remote Similarity	NPD2534	Approved
0.6864	Remote Similarity	NPD2532	Approved
0.6859	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6002	Phase 3
0.6848	Remote Similarity	NPD6004	Phase 3
0.6848	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6005	Phase 3
0.6848	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7819	Suspended
0.6831	Remote Similarity	NPD6764	Approved
0.6831	Remote Similarity	NPD6765	Approved
0.6831	Remote Similarity	NPD6559	Discontinued
0.6829	Remote Similarity	NPD3748	Approved
0.6821	Remote Similarity	NPD6386	Approved
0.6821	Remote Similarity	NPD6385	Approved
0.6807	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1511	Approved
0.6805	Remote Similarity	NPD4357	Discontinued
0.6796	Remote Similarity	NPD7799	Discontinued
0.6795	Remote Similarity	NPD3972	Approved
0.6795	Remote Similarity	NPD2981	Phase 2
0.679	Remote Similarity	NPD1240	Approved
0.6776	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1243	Approved
0.6765	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3146	Approved
0.6763	Remote Similarity	NPD4380	Phase 2
0.6752	Remote Similarity	NPD2982	Phase 2
0.6752	Remote Similarity	NPD2983	Phase 2
0.6748	Remote Similarity	NPD6355	Discontinued
0.6747	Remote Similarity	NPD5762	Approved
0.6747	Remote Similarity	NPD5763	Approved
0.6744	Remote Similarity	NPD1653	Approved
0.6743	Remote Similarity	NPD1465	Phase 2
0.6743	Remote Similarity	NPD5761	Phase 2
0.6743	Remote Similarity	NPD5760	Phase 2
0.6727	Remote Similarity	NPD1510	Phase 2
0.6726	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4110	Phase 3
0.6726	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5089	Approved
0.6724	Remote Similarity	NPD5090	Approved
0.671	Remote Similarity	NPD17	Approved
0.6707	Remote Similarity	NPD1607	Approved
0.6705	Remote Similarity	NPD5402	Approved
0.6705	Remote Similarity	NPD7458	Discontinued
0.6687	Remote Similarity	NPD6100	Approved
0.6687	Remote Similarity	NPD3018	Phase 2
0.6687	Remote Similarity	NPD6099	Approved
0.6687	Remote Similarity	NPD9494	Approved
0.6684	Remote Similarity	NPD6784	Approved
0.6684	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD7229	Phase 3
0.6649	Remote Similarity	NPD8434	Phase 2
0.6648	Remote Similarity	NPD4585	Approved
0.6647	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1471	Phase 3
0.6646	Remote Similarity	NPD1933	Approved
0.6645	Remote Similarity	NPD1651	Approved
0.6627	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4628	Phase 3
0.6627	Remote Similarity	NPD3750	Approved
0.6626	Remote Similarity	NPD8032	Phase 2
0.6608	Remote Similarity	NPD5297	Approved
0.6606	Remote Similarity	NPD6651	Approved
0.6606	Remote Similarity	NPD6653	Approved
0.6588	Remote Similarity	NPD3887	Approved
0.6587	Remote Similarity	NPD2935	Discontinued
0.6585	Remote Similarity	NPD943	Approved
0.6582	Remote Similarity	NPD1608	Approved
0.6579	Remote Similarity	NPD1241	Discontinued
0.6579	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD2654	Approved
0.6564	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7236	Approved
0.6548	Remote Similarity	NPD2353	Approved
0.6548	Remote Similarity	NPD5005	Approved
0.6548	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5006	Approved
0.6545	Remote Similarity	NPD447	Suspended
0.6545	Remote Similarity	NPD3657	Discovery
0.6538	Remote Similarity	NPD1357	Approved
0.6538	Remote Similarity	NPD9268	Approved
0.6536	Remote Similarity	NPD3749	Approved
0.6534	Remote Similarity	NPD7411	Suspended
0.6534	Remote Similarity	NPD6873	Phase 2
0.6532	Remote Similarity	NPD6273	Approved
0.6522	Remote Similarity	NPD2798	Approved
0.6519	Remote Similarity	NPD1281	Approved
0.6517	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7680	Approved
0.651	Remote Similarity	NPD7296	Approved
0.6509	Remote Similarity	NPD1549	Phase 2
0.6506	Remote Similarity	NPD2492	Phase 1
0.6503	Remote Similarity	NPD7095	Approved
0.6494	Remote Similarity	NPD5403	Approved
0.6491	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2438	Suspended
0.6485	Remote Similarity	NPD2979	Phase 3
0.6485	Remote Similarity	NPD3620	Phase 2
0.6485	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD9269	Phase 2
0.6474	Remote Similarity	NPD5401	Approved
0.6471	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6111	Discontinued
0.6463	Remote Similarity	NPD1296	Phase 2
0.6462	Remote Similarity	NPD2975	Approved
0.6462	Remote Similarity	NPD2974	Approved
0.6462	Remote Similarity	NPD2973	Approved
0.646	Remote Similarity	NPD3267	Approved
0.646	Remote Similarity	NPD3266	Approved
0.6453	Remote Similarity	NPD7124	Phase 2
0.645	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.645	Remote Similarity	NPD1375	Discontinued
0.645	Remote Similarity	NPD7266	Discontinued
0.645	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6781	Approved
0.6447	Remote Similarity	NPD4580	Approved
0.6447	Remote Similarity	NPD6779	Approved
0.6447	Remote Similarity	NPD6782	Approved
0.6447	Remote Similarity	NPD6780	Approved
0.6447	Remote Similarity	NPD6776	Approved
0.6447	Remote Similarity	NPD6777	Approved
0.6447	Remote Similarity	NPD6778	Approved
0.6442	Remote Similarity	NPD1529	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