NPASS Compound

Structure

NPC470079 OpenBabel07101718232D 44 47 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4209 -4.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8692 -2.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6139 -2.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2869 -1.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4550 -3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9033 -2.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3551 -1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0281 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1280 -3.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5798 -2.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0939 -3.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8386 -3.3978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0656 -2.0086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8555 0.1088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 12 1 0 0 0 0 2 25 1 0 0 0 0 3 5 1 0 0 0 0 3 19 2 0 0 0 0 4 6 2 0 0 0 0 4 19 1 0 0 0 0 5 22 2 0 0 0 0 6 22 1 0 0 0 0 7 13 2 0 0 0 0 7 20 1 0 0 0 0 8 14 2 0 0 0 0 8 20 1 0 0 0 0 9 15 2 0 0 0 0 9 21 1 0 0 0 0 10 16 2 0 0 0 0 10 21 1 0 0 0 0 11 17 2 0 0 0 0 11 24 1 0 0 0 0 12 30 1 0 0 0 0 13 30 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 31 1 0 0 0 0 17 31 1 0 0 0 0 18 41 1 0 0 0 0 19 32 1 0 0 0 0 20 33 2 0 0 0 0 21 34 2 0 0 0 0 22 42 1 0 0 0 0 23 18 1 6 0 0 0 23 26 1 0 0 0 0 23 43 1 0 0 0 0 24 35 2 0 0 0 0 24 41 1 0 0 0 0 25 36 2 0 0 0 0 25 44 1 0 0 0 0 26 27 1 0 0 0 0 26 37 1 1 0 0 0 27 28 1 0 0 0 0 27 38 1 6 0 0 0 28 29 1 0 0 0 0 28 44 1 1 0 0 0 29 42 1 6 0 0 0 29 43 1 0 0 0 0 30 39 1 0 0 0 0 31 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.17
Volume:	590.505
LogP:	0.849
LogD:	0.182
LogS:	-3.432
# Rotatable Bonds:	12
TPSA:	206.35
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.175
Synthetic Accessibility Score:	4.989
Fsp3:	0.29
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:	-5.01
MDCK Permeability:	1.7138640032499097e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.799
20% Bioavailability (F20%):	0.901
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	87.35114288330078%
Volume Distribution (VD):	0.714
Pgp-substrate:	8.288021087646484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.668
CYP2C9-substrate:	0.515
CYP2D6-inhibitor:	0.685
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.095

ADMET: Excretion

Clearance (CL):	1.847
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.606
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.983
Carcinogencity:	0.789
Eye Corrosion:	0.005
Eye Irritation:	0.228
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC470079

Natural Product ID:	NPC470079
*Common Name:**	Robustaside G
IUPAC Name:	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(E)-3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)prop-2-enoyl]oxymethyl]-2-(4-hydroxyphenoxy)oxan-3-yl] (E)-4-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)but-2-enoate
Synonyms:	Robustaside G
Standard InCHIKey:	CDKLGOOXJLZPAG-LKSTZPJCSA-N
Standard InCHI:	InChI=1S/C31H30O13/c32-19-3-5-22(6-4-19)42-29-28(44-25(36)2-1-12-30(39)13-7-20(33)8-14-30)27(38)26(37)23(43-29)18-41-24(35)11-17-31(40)15-9-21(34)10-16-31/h1-11,13-17,23,26-29,32,37-40H,12,18H2/b2-1+,17-11+/t23-,26-,27+,28-,29-/m1/s1
SMILES:	O=C(/C=C/C1(O)C=CC(=O)C=C1)OC[C@H]1O[C@@H](Oc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/CC1(O)C=CC(=O)C=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669714
PubChem CID:	53318273
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO32611	grevillea "poorinda queen"	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21155593]

☑ 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	10

Activity Type	# Activity
Cell Line	2
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	161000.0	nM	PMID[528588]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	340000.0	nM	PMID[528588]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4700.0	nM	PMID[528588]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5500.0	nM	PMID[528588]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4400.0	nM	PMID[528588]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3900.0	nM	PMID[528588]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2800.0	nM	PMID[528588]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2100.0	nM	PMID[528588]
NPT2	Others	Unspecified		IC50	=	27000.0	nM	PMID[528588]
NPT2	Others	Unspecified		IC50	=	58000.0	nM	PMID[528588]

☑ 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 NPC470079 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	303
0.1-0.2	1614
0.2-0.3	4914
0.3-0.4	10511
0.4-0.5	8516
0.5-0.6	8241
0.6-0.7	7604
0.7-0.8	925
0.8-0.85	58
0.85-0.9	8
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC140750
0.9308	High Similarity	NPC320259
0.9055	High Similarity	NPC233559
0.8915	High Similarity	NPC198487
0.8661	High Similarity	NPC57751
0.8626	High Similarity	NPC146540
0.8618	High Similarity	NPC142319
0.8615	High Similarity	NPC252114
0.8561	High Similarity	NPC295970
0.8529	High Similarity	NPC166180
0.8489	Intermediate Similarity	NPC145319
0.8489	Intermediate Similarity	NPC65833
0.8456	Intermediate Similarity	NPC185778
0.844	Intermediate Similarity	NPC138915
0.8345	Intermediate Similarity	NPC202700
0.8308	Intermediate Similarity	NPC52097
0.8286	Intermediate Similarity	NPC186406
0.8284	Intermediate Similarity	NPC253595
0.8273	Intermediate Similarity	NPC100389
0.8271	Intermediate Similarity	NPC106677
0.8261	Intermediate Similarity	NPC37468
0.8261	Intermediate Similarity	NPC186418
0.8258	Intermediate Similarity	NPC83218
0.8258	Intermediate Similarity	NPC126991
0.8239	Intermediate Similarity	NPC476867
0.8231	Intermediate Similarity	NPC11724
0.8227	Intermediate Similarity	NPC157816
0.8203	Intermediate Similarity	NPC228907
0.8195	Intermediate Similarity	NPC471157
0.8195	Intermediate Similarity	NPC298845
0.8194	Intermediate Similarity	NPC474422
0.8182	Intermediate Similarity	NPC476869
0.8182	Intermediate Similarity	NPC476864
0.8182	Intermediate Similarity	NPC476866
0.8182	Intermediate Similarity	NPC476868
0.8169	Intermediate Similarity	NPC478239
0.8162	Intermediate Similarity	NPC225384
0.8162	Intermediate Similarity	NPC246869
0.8162	Intermediate Similarity	NPC138777
0.8156	Intermediate Similarity	NPC215512
0.8156	Intermediate Similarity	NPC476442
0.8154	Intermediate Similarity	NPC476872
0.8151	Intermediate Similarity	NPC182350
0.8138	Intermediate Similarity	NPC4958
0.8138	Intermediate Similarity	NPC92054
0.8138	Intermediate Similarity	NPC140722
0.8138	Intermediate Similarity	NPC478237
0.8134	Intermediate Similarity	NPC37074
0.8134	Intermediate Similarity	NPC288416
0.8133	Intermediate Similarity	NPC476026
0.8133	Intermediate Similarity	NPC474441
0.8133	Intermediate Similarity	NPC474401
0.8133	Intermediate Similarity	NPC474398
0.8129	Intermediate Similarity	NPC157554
0.8129	Intermediate Similarity	NPC103409
0.8125	Intermediate Similarity	NPC291153
0.8125	Intermediate Similarity	NPC9248
0.8125	Intermediate Similarity	NPC476865
0.812	Intermediate Similarity	NPC470510
0.8112	Intermediate Similarity	NPC292443
0.8112	Intermediate Similarity	NPC232228
0.8099	Intermediate Similarity	NPC245219
0.8099	Intermediate Similarity	NPC31081
0.8095	Intermediate Similarity	NPC93619
0.8095	Intermediate Similarity	NPC131874
0.8088	Intermediate Similarity	NPC60756
0.8082	Intermediate Similarity	NPC22137
0.8079	Intermediate Similarity	NPC231475
0.8079	Intermediate Similarity	NPC57072
0.8074	Intermediate Similarity	NPC40377
0.8074	Intermediate Similarity	NPC225307
0.8071	Intermediate Similarity	NPC124149
0.806	Intermediate Similarity	NPC469622
0.806	Intermediate Similarity	NPC189589
0.806	Intermediate Similarity	NPC171533
0.8056	Intermediate Similarity	NPC226722
0.8045	Intermediate Similarity	NPC221090
0.8045	Intermediate Similarity	NPC25817
0.8045	Intermediate Similarity	NPC287429
0.803	Intermediate Similarity	NPC152722
0.8029	Intermediate Similarity	NPC287780
0.8029	Intermediate Similarity	NPC254819
0.8029	Intermediate Similarity	NPC235294
0.8029	Intermediate Similarity	NPC478255
0.8029	Intermediate Similarity	NPC46137
0.8028	Intermediate Similarity	NPC80098
0.8015	Intermediate Similarity	NPC269242
0.8015	Intermediate Similarity	NPC97326
0.8015	Intermediate Similarity	NPC198734
0.8015	Intermediate Similarity	NPC469412
0.8014	Intermediate Similarity	NPC226005
0.8	Intermediate Similarity	NPC173150
0.8	Intermediate Similarity	NPC471882
0.8	Intermediate Similarity	NPC471881
0.8	Intermediate Similarity	NPC35288
0.8	Intermediate Similarity	NPC45224
0.8	Intermediate Similarity	NPC156692
0.8	Intermediate Similarity	NPC199928
0.8	Intermediate Similarity	NPC472132
0.7986	Intermediate Similarity	NPC471028
0.7986	Intermediate Similarity	NPC110063
0.7986	Intermediate Similarity	NPC471029
0.7973	Intermediate Similarity	NPC213197
0.7972	Intermediate Similarity	NPC140502
0.797	Intermediate Similarity	NPC217854
0.797	Intermediate Similarity	NPC192810
0.7959	Intermediate Similarity	NPC206264
0.7959	Intermediate Similarity	NPC313334
0.7959	Intermediate Similarity	NPC212670
0.7956	Intermediate Similarity	NPC208769
0.7955	Intermediate Similarity	NPC226712
0.7945	Intermediate Similarity	NPC87950
0.7945	Intermediate Similarity	NPC97240
0.7945	Intermediate Similarity	NPC471764
0.7941	Intermediate Similarity	NPC247146
0.7939	Intermediate Similarity	NPC469708
0.7939	Intermediate Similarity	NPC60589
0.7933	Intermediate Similarity	NPC230439
0.7933	Intermediate Similarity	NPC92153
0.7933	Intermediate Similarity	NPC279281
0.7933	Intermediate Similarity	NPC299761
0.7931	Intermediate Similarity	NPC476382
0.7931	Intermediate Similarity	NPC100998
0.7931	Intermediate Similarity	NPC34587
0.7931	Intermediate Similarity	NPC252292
0.7931	Intermediate Similarity	NPC34927
0.7931	Intermediate Similarity	NPC85624
0.7929	Intermediate Similarity	NPC55040
0.7929	Intermediate Similarity	NPC476870
0.7917	Intermediate Similarity	NPC237872
0.7917	Intermediate Similarity	NPC116104
0.7917	Intermediate Similarity	NPC88754
0.7917	Intermediate Similarity	NPC263397
0.7917	Intermediate Similarity	NPC469367
0.7917	Intermediate Similarity	NPC242756
0.7917	Intermediate Similarity	NPC302286
0.7914	Intermediate Similarity	NPC28637
0.7914	Intermediate Similarity	NPC60982
0.7905	Intermediate Similarity	NPC476871
0.7905	Intermediate Similarity	NPC114740
0.7902	Intermediate Similarity	NPC79908
0.7891	Intermediate Similarity	NPC96294
0.7891	Intermediate Similarity	NPC169510
0.7891	Intermediate Similarity	NPC83975
0.7883	Intermediate Similarity	NPC477293
0.7883	Intermediate Similarity	NPC218003
0.7883	Intermediate Similarity	NPC477294
0.7883	Intermediate Similarity	NPC229784
0.7879	Intermediate Similarity	NPC276195
0.7877	Intermediate Similarity	NPC37838
0.7871	Intermediate Similarity	NPC475183
0.7868	Intermediate Similarity	NPC469621
0.7867	Intermediate Similarity	NPC34965
0.7867	Intermediate Similarity	NPC215811
0.7867	Intermediate Similarity	NPC183536
0.7857	Intermediate Similarity	NPC34456
0.7857	Intermediate Similarity	NPC130496
0.7857	Intermediate Similarity	NPC188555
0.7847	Intermediate Similarity	NPC164599
0.7842	Intermediate Similarity	NPC85799
0.7842	Intermediate Similarity	NPC303422
0.7842	Intermediate Similarity	NPC473924
0.7842	Intermediate Similarity	NPC269421
0.7842	Intermediate Similarity	NPC26080
0.7842	Intermediate Similarity	NPC473285
0.7842	Intermediate Similarity	NPC165686
0.7838	Intermediate Similarity	NPC106138
0.7838	Intermediate Similarity	NPC478242
0.7823	Intermediate Similarity	NPC52740
0.7823	Intermediate Similarity	NPC41844
0.7823	Intermediate Similarity	NPC296377
0.7823	Intermediate Similarity	NPC232992
0.7821	Intermediate Similarity	NPC280923
0.7817	Intermediate Similarity	NPC78363
0.7812	Intermediate Similarity	NPC474641
0.781	Intermediate Similarity	NPC232880
0.7808	Intermediate Similarity	NPC287615
0.7808	Intermediate Similarity	NPC83743
0.7808	Intermediate Similarity	NPC216819
0.7808	Intermediate Similarity	NPC262182
0.7801	Intermediate Similarity	NPC263829
0.7801	Intermediate Similarity	NPC238243
0.7794	Intermediate Similarity	NPC61181
0.7793	Intermediate Similarity	NPC475213
0.7793	Intermediate Similarity	NPC152796
0.7786	Intermediate Similarity	NPC115022
0.7786	Intermediate Similarity	NPC254398
0.7786	Intermediate Similarity	NPC294166
0.7785	Intermediate Similarity	NPC470934
0.7785	Intermediate Similarity	NPC471214
0.7785	Intermediate Similarity	NPC188393
0.7785	Intermediate Similarity	NPC100818
0.7771	Intermediate Similarity	NPC475174
0.777	Intermediate Similarity	NPC28651
0.777	Intermediate Similarity	NPC121376
0.777	Intermediate Similarity	NPC261122
0.777	Intermediate Similarity	NPC220282
0.777	Intermediate Similarity	NPC3460
0.777	Intermediate Similarity	NPC80732
0.777	Intermediate Similarity	NPC300262

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 NPC470079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	880
0.2-0.3	2277
0.3-0.4	2934
0.4-0.5	1678
0.5-0.6	894
0.6-0.7	233
0.7-0.8	5
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
0.7959	Intermediate Similarity	NPD1653	Approved
0.7955	Intermediate Similarity	NPD1091	Approved
0.7639	Intermediate Similarity	NPD7266	Discontinued
0.7436	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8455	Phase 2
0.7089	Intermediate Similarity	NPD5402	Approved
0.7078	Intermediate Similarity	NPD5403	Approved
0.7075	Intermediate Similarity	NPD7097	Phase 1
0.7067	Intermediate Similarity	NPD1652	Phase 2
0.7055	Intermediate Similarity	NPD5124	Phase 1
0.7055	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6233	Phase 2
0.7024	Intermediate Similarity	NPD8313	Approved
0.7024	Intermediate Similarity	NPD8312	Approved
0.6978	Remote Similarity	NPD3496	Discontinued
0.6953	Remote Similarity	NPD291	Approved
0.6948	Remote Similarity	NPD5401	Approved
0.6947	Remote Similarity	NPD1358	Approved
0.6939	Remote Similarity	NPD4340	Discontinued
0.6928	Remote Similarity	NPD7054	Approved
0.6928	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5647	Approved
0.6911	Remote Similarity	NPD9365	Approved
0.6908	Remote Similarity	NPD4628	Phase 3
0.6905	Remote Similarity	NPD6559	Discontinued
0.6905	Remote Similarity	NPD7685	Pre-registration
0.6901	Remote Similarity	NPD3225	Approved
0.6886	Remote Similarity	NPD7074	Phase 3
0.6886	Remote Similarity	NPD7472	Approved
0.687	Remote Similarity	NPD968	Approved
0.6867	Remote Similarity	NPD3751	Discontinued
0.6867	Remote Similarity	NPD3818	Discontinued
0.6863	Remote Similarity	NPD6190	Approved
0.6853	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6797	Phase 2
0.6842	Remote Similarity	NPD556	Approved
0.6839	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4380	Phase 2
0.6832	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5058	Phase 3
0.6818	Remote Similarity	NPD290	Approved
0.6809	Remote Similarity	NPD422	Phase 1
0.6805	Remote Similarity	NPD7251	Discontinued
0.68	Remote Similarity	NPD7033	Discontinued
0.679	Remote Similarity	NPD7075	Discontinued
0.6765	Remote Similarity	NPD7808	Phase 3
0.6759	Remote Similarity	NPD2861	Phase 2
0.6757	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1613	Approved
0.6742	Remote Similarity	NPD3134	Approved
0.6741	Remote Similarity	NPD969	Suspended
0.6733	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7843	Approved
0.6688	Remote Similarity	NPD3750	Approved
0.6688	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD6671	Approved
0.6667	Remote Similarity	NPD6653	Approved
0.6647	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6801	Discontinued
0.6642	Remote Similarity	NPD2684	Approved
0.6627	Remote Similarity	NPD3787	Discontinued
0.6623	Remote Similarity	NPD6674	Discontinued
0.6623	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6798	Discontinued
0.6621	Remote Similarity	NPD6362	Approved
0.6613	Remote Similarity	NPD9295	Approved
0.6605	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD521	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1933	Approved
0.6599	Remote Similarity	NPD4908	Phase 1
0.6597	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7411	Suspended
0.6573	Remote Similarity	NPD1535	Discovery
0.6568	Remote Similarity	NPD7228	Approved
0.6567	Remote Similarity	NPD9552	Approved
0.6561	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6799	Approved
0.6558	Remote Similarity	NPD1549	Phase 2
0.6554	Remote Similarity	NPD3027	Phase 3
0.6552	Remote Similarity	NPD8651	Approved
0.655	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7157	Approved
0.6547	Remote Similarity	NPD191	Approved
0.6541	Remote Similarity	NPD9697	Approved
0.6536	Remote Similarity	NPD1551	Phase 2
0.6536	Remote Similarity	NPD3454	Phase 3
0.6534	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4060	Phase 1
0.6529	Remote Similarity	NPD5844	Phase 1
0.6528	Remote Similarity	NPD1481	Phase 2
0.6525	Remote Similarity	NPD1548	Phase 1
0.6519	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4538	Approved
0.6513	Remote Similarity	NPD4536	Approved
0.651	Remote Similarity	NPD3268	Approved
0.651	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2797	Approved
0.6507	Remote Similarity	NPD1203	Approved
0.6494	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5763	Approved
0.6494	Remote Similarity	NPD5762	Approved
0.6494	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4749	Approved
0.6479	Remote Similarity	NPD1357	Approved
0.6478	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5960	Phase 3
0.6471	Remote Similarity	NPD5588	Approved
0.6467	Remote Similarity	NPD7435	Discontinued
0.6467	Remote Similarity	NPD4062	Phase 3
0.6458	Remote Similarity	NPD1610	Phase 2
0.645	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6166	Phase 2
0.6449	Remote Similarity	NPD5535	Approved
0.6446	Remote Similarity	NPD6234	Discontinued
0.6443	Remote Similarity	NPD7095	Approved
0.6442	Remote Similarity	NPD1934	Approved
0.6442	Remote Similarity	NPD37	Approved
0.6434	Remote Similarity	NPD1778	Approved
0.6424	Remote Similarity	NPD4967	Phase 2
0.6424	Remote Similarity	NPD4965	Approved
0.6424	Remote Similarity	NPD4966	Approved
0.6419	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3536	Discontinued
0.6414	Remote Similarity	NPD9717	Approved
0.6408	Remote Similarity	NPD9545	Approved
0.6403	Remote Similarity	NPD1241	Discontinued
0.6402	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2801	Approved
0.64	Remote Similarity	NPD1048	Approved
0.6393	Remote Similarity	NPD6779	Approved
0.6393	Remote Similarity	NPD6777	Approved
0.6393	Remote Similarity	NPD6780	Approved
0.6393	Remote Similarity	NPD6781	Approved
0.6393	Remote Similarity	NPD6778	Approved
0.6393	Remote Similarity	NPD6782	Approved
0.6393	Remote Similarity	NPD6776	Approved
0.6387	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6004	Phase 3
0.6387	Remote Similarity	NPD6002	Phase 3
0.6387	Remote Similarity	NPD6005	Phase 3
0.6387	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6355	Discontinued
0.6376	Remote Similarity	NPD6832	Phase 2
0.6369	Remote Similarity	NPD7199	Phase 2
0.6369	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3817	Phase 2
0.6364	Remote Similarity	NPD3748	Approved
0.6358	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7458	Discontinued
0.6357	Remote Similarity	NPD9296	Approved
0.6345	Remote Similarity	NPD3705	Approved
0.6343	Remote Similarity	NPD9501	Approved
0.634	Remote Similarity	NPD2223	Approved
0.634	Remote Similarity	NPD2224	Approved
0.6335	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD769	Approved
0.6328	Remote Similarity	NPD8434	Phase 2
0.6324	Remote Similarity	NPD6823	Phase 2
0.6323	Remote Similarity	NPD2935	Discontinued
0.6319	Remote Similarity	NPD6599	Discontinued
0.6319	Remote Similarity	NPD6516	Phase 2
0.6319	Remote Similarity	NPD5846	Approved
0.6319	Remote Similarity	NPD5125	Phase 3
0.6319	Remote Similarity	NPD5126	Approved
0.6312	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7819	Suspended
0.6294	Remote Similarity	NPD1894	Discontinued
0.6291	Remote Similarity	NPD2313	Discontinued
0.6286	Remote Similarity	NPD7549	Discontinued
0.6275	Remote Similarity	NPD447	Suspended
0.6272	Remote Similarity	NPD8127	Discontinued
0.6265	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7874	Approved
0.6259	Remote Similarity	NPD3685	Discontinued
0.6258	Remote Similarity	NPD4308	Phase 3
0.6257	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5585	Approved
0.6243	Remote Similarity	NPD7585	Approved
0.6236	Remote Similarity	NPD8150	Discontinued
0.6233	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7783	Phase 2
0.6229	Remote Similarity	NPD7240	Approved
0.6228	Remote Similarity	NPD7768	Phase 2
0.6225	Remote Similarity	NPD4625	Phase 3
0.6225	Remote Similarity	NPD3179	Approved
0.6225	Remote Similarity	NPD3180	Approved
0.6224	Remote Similarity	NPD9092	Discovery
0.6224	Remote Similarity	NPD5536	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