NPASS Compound

Structure

NPC282551 OpenBabel07101719252D 46 50 0 0 1 0 0 0 0 0999 V2000 -3.8991 -0.7901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2074 4.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3413 1.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2074 1.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6547 2.7647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6765 2.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4753 2.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7727 0.4124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5375 3.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4753 1.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9637 1.8136 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2074 2.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3413 3.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8772 1.4069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.6715 2.9069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2946 1.0705 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.6715 1.9069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.8054 1.4069 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9394 1.9069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6093 1.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 1.2784 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9394 2.9069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7946 0.2044 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.4035 2.9069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6254 -0.3273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.5375 1.4069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2653 1.3669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8054 0.4069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 2.8532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0734 1.4069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0292 2.4373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6093 0.4069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9855 -0.3833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3413 4.4069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7433 1.9069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0734 3.4069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8054 3.4069 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 -1.6473 0.5352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 40 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 6 41 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 8 29 1 0 0 0 0 9 30 1 0 0 0 0 10 31 1 0 0 0 0 11 25 1 0 0 0 0 12 5 1 6 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 43 1 0 0 0 0 14 40 1 0 0 0 0 15 42 1 1 0 0 0 16 9 1 1 0 0 0 16 19 1 0 0 0 0 16 44 1 0 0 0 0 17 10 1 1 0 0 0 17 20 1 0 0 0 0 17 45 1 0 0 0 0 18 26 1 0 0 0 0 18 29 1 6 0 0 0 19 21 1 0 0 0 0 19 32 1 6 0 0 0 20 22 1 0 0 0 0 20 33 1 6 0 0 0 21 23 1 0 0 0 0 21 34 1 1 0 0 0 22 24 1 0 0 0 0 22 35 1 1 0 0 0 23 27 1 0 0 0 0 23 36 1 6 0 0 0 24 28 1 0 0 0 0 24 37 1 6 0 0 0 25 38 2 0 0 0 0 25 42 1 0 0 0 0 26 41 1 0 0 0 0 26 46 1 1 0 0 0 27 43 1 1 0 0 0 27 44 1 0 0 0 0 28 45 1 0 0 0 0 28 46 1 1 0 0 0 29 1 1 6 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	660.23
Volume:	603.609
LogP:	-0.39
LogD:	-0.078
LogS:	-2.322
# Rotatable Bonds:	10
TPSA:	263.75
# H-Bond Aceptor:	17
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	5.283
Fsp3:	0.69
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.719
MDCK Permeability:	0.0001972802128875628
Pgp-inhibitor:	0.002
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.974
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.183
Plasma Protein Binding (PPB):	30.473045349121094%
Volume Distribution (VD):	0.449
Pgp-substrate:	22.804052352905273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	0.995
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.26
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.464
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.026
Carcinogencity:	0.461
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC282551

Natural Product ID:	NPC282551
*Common Name:**	Rehmaglutoside B
IUPAC Name:	[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
Synonyms:	Rehmaglutoside B
Standard InCHIKey:	WEDMMISOMZMEJJ-LSEZEHEGSA-N
Standard InCHI:	InChI=1S/C29H40O17/c1-29(39)8-15(12-5-6-41-26(18(12)29)46-28-24(37)22(35)20(33)17(10-31)45-28)42-25(38)11-3-4-13(14(7-11)40-2)43-27-23(36)21(34)19(32)16(9-30)44-27/h3-7,12,15-24,26-28,30-37,39H,8-10H2,1-2H3/t12-,15+,16+,17+,18+,19+,20+,21-,22-,23+,24+,26-,27+,28-,29-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@](C)(O)C[C@H]3OC(=O)c2ccc(c(c2)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2177297
PubChem CID:	71453616
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[489116]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[489116]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[489116]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[489116]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[489116]

☑ 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 NPC282551 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	363
0.1-0.2	1460
0.2-0.3	3109
0.3-0.4	6573
0.4-0.5	10534
0.5-0.6	7383
0.6-0.7	8413
0.7-0.8	4551
0.8-0.85	257
0.85-0.9	46
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC470685
0.9679	High Similarity	NPC474936
0.9434	High Similarity	NPC476011
0.9434	High Similarity	NPC206815
0.9259	High Similarity	NPC130730
0.9259	High Similarity	NPC301910
0.9146	High Similarity	NPC21956
0.9006	High Similarity	NPC179914
0.8994	High Similarity	NPC478232
0.8974	High Similarity	NPC308178
0.8951	High Similarity	NPC138993
0.8902	High Similarity	NPC109990
0.8868	High Similarity	NPC36130
0.8868	High Similarity	NPC134905
0.8861	High Similarity	NPC147224
0.8841	High Similarity	NPC145847
0.8812	High Similarity	NPC137813
0.8805	High Similarity	NPC269914
0.8805	High Similarity	NPC478249
0.8805	High Similarity	NPC475379
0.8797	High Similarity	NPC478234
0.8797	High Similarity	NPC478236
0.8786	High Similarity	NPC96194
0.8786	High Similarity	NPC299855
0.8758	High Similarity	NPC327032
0.8758	High Similarity	NPC191046
0.8758	High Similarity	NPC194095
0.875	High Similarity	NPC203664
0.8742	High Similarity	NPC227980
0.8736	High Similarity	NPC189704
0.8712	High Similarity	NPC187205
0.8712	High Similarity	NPC133984
0.8712	High Similarity	NPC226759
0.8704	High Similarity	NPC475484
0.8704	High Similarity	NPC10205
0.8688	High Similarity	NPC289021
0.8688	High Similarity	NPC158546
0.8686	High Similarity	NPC476067
0.8686	High Similarity	NPC475121
0.8679	High Similarity	NPC111785
0.8671	High Similarity	NPC473149
0.8671	High Similarity	NPC473776
0.8671	High Similarity	NPC473205
0.865	High Similarity	NPC471405
0.8634	High Similarity	NPC194705
0.8625	High Similarity	NPC117346
0.8625	High Similarity	NPC240592
0.8623	High Similarity	NPC180586
0.8623	High Similarity	NPC472131
0.8623	High Similarity	NPC472130
0.8614	High Similarity	NPC41009
0.8608	High Similarity	NPC37838
0.8606	High Similarity	NPC478265
0.8596	High Similarity	NPC169645
0.8596	High Similarity	NPC84482
0.858	High Similarity	NPC658
0.858	High Similarity	NPC89693
0.858	High Similarity	NPC197708
0.858	High Similarity	NPC229548
0.858	High Similarity	NPC478241
0.8545	High Similarity	NPC469384
0.8545	High Similarity	NPC289811
0.8545	High Similarity	NPC160780
0.8539	High Similarity	NPC475299
0.8538	High Similarity	NPC163165
0.8538	High Similarity	NPC316539
0.8537	High Similarity	NPC478248
0.8535	High Similarity	NPC242756
0.8531	High Similarity	NPC71385
0.8531	High Similarity	NPC230670
0.8529	High Similarity	NPC472129
0.8529	High Similarity	NPC43434
0.8526	High Similarity	NPC80098
0.8519	High Similarity	NPC289438
0.8519	High Similarity	NPC478235
0.8509	High Similarity	NPC205054
0.8509	High Similarity	NPC229882
0.8509	High Similarity	NPC158635
0.8509	High Similarity	NPC69367
0.8503	High Similarity	NPC285108
0.8503	High Similarity	NPC33298
0.8503	High Similarity	NPC148273
0.8494	Intermediate Similarity	NPC203020
0.8494	Intermediate Similarity	NPC239966
0.8485	Intermediate Similarity	NPC1913
0.8485	Intermediate Similarity	NPC286919
0.8485	Intermediate Similarity	NPC475663
0.8483	Intermediate Similarity	NPC112708
0.8481	Intermediate Similarity	NPC471028
0.848	Intermediate Similarity	NPC5786
0.848	Intermediate Similarity	NPC102851
0.8471	Intermediate Similarity	NPC472133
0.8466	Intermediate Similarity	NPC246893
0.8466	Intermediate Similarity	NPC157898
0.8466	Intermediate Similarity	NPC229354
0.8466	Intermediate Similarity	NPC105827
0.8466	Intermediate Similarity	NPC310661
0.8447	Intermediate Similarity	NPC96599
0.8443	Intermediate Similarity	NPC311803
0.8443	Intermediate Similarity	NPC472859
0.8443	Intermediate Similarity	NPC25389
0.8436	Intermediate Similarity	NPC473711
0.843	Intermediate Similarity	NPC195972
0.8418	Intermediate Similarity	NPC152796
0.8418	Intermediate Similarity	NPC88754
0.8418	Intermediate Similarity	NPC116104
0.8418	Intermediate Similarity	NPC263397
0.8418	Intermediate Similarity	NPC302286
0.8418	Intermediate Similarity	NPC237872
0.8418	Intermediate Similarity	NPC475213
0.8412	Intermediate Similarity	NPC208818
0.8395	Intermediate Similarity	NPC182350
0.8393	Intermediate Similarity	NPC246024
0.8383	Intermediate Similarity	NPC289346
0.8383	Intermediate Similarity	NPC119125
0.8383	Intermediate Similarity	NPC166277
0.8375	Intermediate Similarity	NPC473867
0.8373	Intermediate Similarity	NPC472860
0.8365	Intermediate Similarity	NPC77922
0.8365	Intermediate Similarity	NPC473281
0.8365	Intermediate Similarity	NPC478240
0.8354	Intermediate Similarity	NPC299706
0.8354	Intermediate Similarity	NPC61604
0.8354	Intermediate Similarity	NPC245615
0.8354	Intermediate Similarity	NPC115466
0.8343	Intermediate Similarity	NPC100425
0.8343	Intermediate Similarity	NPC227297
0.8333	Intermediate Similarity	NPC98809
0.8333	Intermediate Similarity	NPC478242
0.8333	Intermediate Similarity	NPC476394
0.8323	Intermediate Similarity	NPC74319
0.8323	Intermediate Similarity	NPC287872
0.8314	Intermediate Similarity	NPC52598
0.8313	Intermediate Similarity	NPC163635
0.8313	Intermediate Similarity	NPC478266
0.8304	Intermediate Similarity	NPC298847
0.8303	Intermediate Similarity	NPC472127
0.8303	Intermediate Similarity	NPC472128
0.8302	Intermediate Similarity	NPC469367
0.8295	Intermediate Similarity	NPC188217
0.8294	Intermediate Similarity	NPC15358
0.8294	Intermediate Similarity	NPC475497
0.8294	Intermediate Similarity	NPC475366
0.8294	Intermediate Similarity	NPC284277
0.8291	Intermediate Similarity	NPC79908
0.8284	Intermediate Similarity	NPC90905
0.8284	Intermediate Similarity	NPC4013
0.8276	Intermediate Similarity	NPC469354
0.8272	Intermediate Similarity	NPC472969
0.8266	Intermediate Similarity	NPC475155
0.8266	Intermediate Similarity	NPC38438
0.8263	Intermediate Similarity	NPC4747
0.8263	Intermediate Similarity	NPC49173
0.8263	Intermediate Similarity	NPC104275
0.8261	Intermediate Similarity	NPC476865
0.8256	Intermediate Similarity	NPC61791
0.8253	Intermediate Similarity	NPC156624
0.8253	Intermediate Similarity	NPC172920
0.825	Intermediate Similarity	NPC296659
0.825	Intermediate Similarity	NPC202391
0.825	Intermediate Similarity	NPC473090
0.8249	Intermediate Similarity	NPC473883
0.8249	Intermediate Similarity	NPC199172
0.8249	Intermediate Similarity	NPC35924
0.8235	Intermediate Similarity	NPC100420
0.8229	Intermediate Similarity	NPC67629
0.8229	Intermediate Similarity	NPC79736
0.8229	Intermediate Similarity	NPC473713
0.8225	Intermediate Similarity	NPC182045
0.8214	Intermediate Similarity	NPC76211
0.8214	Intermediate Similarity	NPC469654
0.821	Intermediate Similarity	NPC18789
0.8204	Intermediate Similarity	NPC475378
0.8199	Intermediate Similarity	NPC476866
0.8199	Intermediate Similarity	NPC476868
0.8199	Intermediate Similarity	NPC476869
0.8199	Intermediate Similarity	NPC476864
0.8198	Intermediate Similarity	NPC116745
0.8198	Intermediate Similarity	NPC135345
0.8198	Intermediate Similarity	NPC128403
0.8193	Intermediate Similarity	NPC476364
0.8187	Intermediate Similarity	NPC293154
0.8187	Intermediate Similarity	NPC475738
0.8182	Intermediate Similarity	NPC267549
0.8182	Intermediate Similarity	NPC475261
0.8182	Intermediate Similarity	NPC173837
0.8182	Intermediate Similarity	NPC120952
0.8171	Intermediate Similarity	NPC469438
0.8171	Intermediate Similarity	NPC473091
0.8171	Intermediate Similarity	NPC470934
0.8171	Intermediate Similarity	NPC188393
0.8171	Intermediate Similarity	NPC107739
0.8166	Intermediate Similarity	NPC110349
0.8166	Intermediate Similarity	NPC44507
0.8161	Intermediate Similarity	NPC172807
0.8161	Intermediate Similarity	NPC261254
0.8161	Intermediate Similarity	NPC235575
0.8161	Intermediate Similarity	NPC254540
0.8161	Intermediate Similarity	NPC472386
0.8161	Intermediate Similarity	NPC211594

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 NPC282551 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	847
0.2-0.3	1863
0.3-0.4	2606
0.4-0.5	2072
0.5-0.6	1027
0.6-0.7	366
0.7-0.8	66
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9212	High Similarity	NPD7685	Pre-registration
0.8208	Intermediate Similarity	NPD7472	Approved
0.815	Intermediate Similarity	NPD7054	Approved
0.8068	Intermediate Similarity	NPD7808	Phase 3
0.8011	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7989	Intermediate Similarity	NPD3818	Discontinued
0.7966	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6797	Phase 2
0.7933	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7266	Discontinued
0.7714	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8127	Discontinued
0.7684	Intermediate Similarity	NPD7228	Approved
0.7679	Intermediate Similarity	NPD1653	Approved
0.7661	Intermediate Similarity	NPD8455	Phase 2
0.7651	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD8313	Approved
0.7624	Intermediate Similarity	NPD8312	Approved
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3817	Phase 2
0.7611	Intermediate Similarity	NPD7240	Approved
0.7576	Intermediate Similarity	NPD4628	Phase 3
0.7556	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD5494	Approved
0.7542	Intermediate Similarity	NPD5844	Phase 1
0.7542	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD37	Approved
0.7472	Intermediate Similarity	NPD6166	Phase 2
0.7472	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.7469	Intermediate Similarity	NPD6653	Approved
0.7457	Intermediate Similarity	NPD1465	Phase 2
0.7456	Intermediate Similarity	NPD6273	Approved
0.7425	Intermediate Similarity	NPD6190	Approved
0.7399	Intermediate Similarity	NPD1934	Approved
0.7386	Intermediate Similarity	NPD6234	Discontinued
0.7384	Intermediate Similarity	NPD7028	Phase 2
0.7356	Intermediate Similarity	NPD2801	Approved
0.734	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6559	Discontinued
0.7314	Intermediate Similarity	NPD5353	Approved
0.7301	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD3882	Suspended
0.7257	Intermediate Similarity	NPD7819	Suspended
0.7257	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7075	Discontinued
0.7219	Intermediate Similarity	NPD8434	Phase 2
0.7216	Intermediate Similarity	NPD5402	Approved
0.7202	Intermediate Similarity	NPD6674	Discontinued
0.7195	Intermediate Similarity	NPD1933	Approved
0.7195	Intermediate Similarity	NPD447	Suspended
0.7193	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4380	Phase 2
0.716	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4110	Phase 3
0.7159	Intermediate Similarity	NPD5760	Phase 2
0.7159	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD6385	Approved
0.7143	Intermediate Similarity	NPD9494	Approved
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7108	Intermediate Similarity	NPD7097	Phase 1
0.7104	Intermediate Similarity	NPD3751	Discontinued
0.7104	Intermediate Similarity	NPD7799	Discontinued
0.7102	Intermediate Similarity	NPD6801	Discontinued
0.7091	Intermediate Similarity	NPD6355	Discontinued
0.7083	Intermediate Similarity	NPD6002	Phase 3
0.7083	Intermediate Similarity	NPD6005	Phase 3
0.7083	Intermediate Similarity	NPD5762	Approved
0.7083	Intermediate Similarity	NPD6004	Phase 3
0.7083	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5763	Approved
0.7083	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5647	Approved
0.7072	Intermediate Similarity	NPD3787	Discontinued
0.7072	Intermediate Similarity	NPD6232	Discontinued
0.7035	Intermediate Similarity	NPD1511	Approved
0.7035	Intermediate Similarity	NPD6799	Approved
0.7019	Intermediate Similarity	NPD6362	Approved
0.7011	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5401	Approved
0.698	Remote Similarity	NPD7783	Phase 2
0.698	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7497	Discontinued
0.697	Remote Similarity	NPD7435	Discontinued
0.6965	Remote Similarity	NPD8151	Discontinued
0.6964	Remote Similarity	NPD7033	Discontinued
0.6954	Remote Similarity	NPD1512	Approved
0.6952	Remote Similarity	NPD6765	Approved
0.6952	Remote Similarity	NPD6764	Approved
0.6949	Remote Similarity	NPD7411	Suspended
0.6941	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1608	Approved
0.6927	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD919	Approved
0.69	Remote Similarity	NPD7999	Approved
0.6893	Remote Similarity	NPD6599	Discontinued
0.6884	Remote Similarity	NPD7680	Approved
0.6879	Remote Similarity	NPD7236	Approved
0.6875	Remote Similarity	NPD3705	Approved
0.6875	Remote Similarity	NPD1091	Approved
0.6867	Remote Similarity	NPD6233	Phase 2
0.6866	Remote Similarity	NPD7583	Approved
0.6862	Remote Similarity	NPD7038	Approved
0.6862	Remote Similarity	NPD7039	Approved
0.686	Remote Similarity	NPD3750	Approved
0.686	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5242	Approved
0.6836	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9545	Approved
0.6832	Remote Similarity	NPD7585	Approved
0.6826	Remote Similarity	NPD4140	Approved
0.6826	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2796	Approved
0.6818	Remote Similarity	NPD6782	Approved
0.6818	Remote Similarity	NPD6777	Approved
0.6818	Remote Similarity	NPD6776	Approved
0.6818	Remote Similarity	NPD6779	Approved
0.6818	Remote Similarity	NPD6781	Approved
0.6818	Remote Similarity	NPD6778	Approved
0.6818	Remote Similarity	NPD6780	Approved
0.6806	Remote Similarity	NPD6785	Approved
0.6806	Remote Similarity	NPD6784	Approved
0.68	Remote Similarity	NPD7696	Phase 3
0.68	Remote Similarity	NPD7698	Approved
0.68	Remote Similarity	NPD7697	Approved
0.6796	Remote Similarity	NPD7930	Approved
0.678	Remote Similarity	NPD7239	Suspended
0.6771	Remote Similarity	NPD8150	Discontinued
0.6768	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD8320	Phase 1
0.6766	Remote Similarity	NPD8319	Approved
0.6765	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3748	Approved
0.6765	Remote Similarity	NPD2799	Discontinued
0.6765	Remote Similarity	NPD7874	Approved
0.6758	Remote Similarity	NPD3749	Approved
0.6757	Remote Similarity	NPD3926	Phase 2
0.675	Remote Similarity	NPD17	Approved
0.6749	Remote Similarity	NPD7701	Phase 2
0.6747	Remote Similarity	NPD7095	Approved
0.6744	Remote Similarity	NPD1549	Phase 2
0.6742	Remote Similarity	NPD3226	Approved
0.674	Remote Similarity	NPD5977	Approved
0.674	Remote Similarity	NPD5978	Approved
0.6739	Remote Similarity	NPD1247	Approved
0.6739	Remote Similarity	NPD6959	Discontinued
0.672	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6798	Discontinued
0.6707	Remote Similarity	NPD3764	Approved
0.6705	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2534	Approved
0.6705	Remote Similarity	NPD2532	Approved
0.6705	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3146	Approved
0.6705	Remote Similarity	NPD2533	Approved
0.6705	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1652	Phase 2
0.6703	Remote Similarity	NPD7768	Phase 2
0.67	Remote Similarity	NPD7584	Approved
0.6687	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6832	Phase 2
0.6687	Remote Similarity	NPD1357	Approved
0.6686	Remote Similarity	NPD5124	Phase 1
0.6686	Remote Similarity	NPD5735	Approved
0.6686	Remote Similarity	NPD2346	Discontinued
0.6686	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7871	Phase 2
0.6683	Remote Similarity	NPD7870	Phase 2
0.6667	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD8166	Discontinued
0.665	Remote Similarity	NPD7801	Approved
0.6647	Remote Similarity	NPD3027	Phase 3
0.6647	Remote Similarity	NPD2424	Discontinued
0.6633	Remote Similarity	NPD7296	Approved
0.6633	Remote Similarity	NPD7700	Phase 2
0.6633	Remote Similarity	NPD7699	Phase 2
0.663	Remote Similarity	NPD6844	Discontinued
0.663	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3887	Approved
0.6629	Remote Similarity	NPD2354	Approved
0.6629	Remote Similarity	NPD920	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data