NPASS Compound

Structure

CID104275 OpenBabel06191715452D 42 45 0 0 1 0 0 0 0 0999 V2000 -8.7648 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8007 -3.8605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8007 -3.8605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4328 -4.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1270 -3.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1759 -3.6666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -2.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6407 -5.3138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3349 -4.9537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8366 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5917 -5.6229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7026 -4.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5686 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9680 -2.6884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -2.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3007 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 1.2260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8975 -5.9830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2859 -5.2628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7996 -6.6010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4727 -0.7626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7111 -2.0193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 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 -2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 28 1 0 0 0 0 3 28 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 16 2 0 0 0 0 10 29 1 0 0 0 0 11 38 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 1 0 0 0 15 19 2 0 0 0 0 15 30 1 0 0 0 0 16 19 1 0 0 0 0 16 31 1 0 0 0 0 17 10 1 1 0 0 0 17 21 1 0 0 0 0 17 39 1 0 0 0 0 18 11 1 6 0 0 0 18 20 1 0 0 0 0 18 40 1 0 0 0 0 19 32 1 0 0 0 0 20 22 1 0 0 0 0 20 33 1 1 0 0 0 21 24 1 0 0 0 0 21 34 1 6 0 0 0 22 23 1 0 0 0 0 22 35 1 6 0 0 0 23 26 1 0 0 0 0 23 36 1 1 0 0 0 24 27 1 0 0 0 0 24 41 1 1 0 0 0 25 37 2 0 0 0 0 25 41 1 0 0 0 0 26 40 1 0 0 0 0 26 42 1 6 0 0 0 27 38 1 6 0 0 0 27 39 1 0 0 0 0 28 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.24
Volume:	568.499
LogP:	1.359
LogD:	0.584
LogS:	-3.162
# Rotatable Bonds:	10
TPSA:	225.06
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.104
Synthetic Accessibility Score:	4.966
Fsp3:	0.679
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.373
MDCK Permeability:	3.4675129427341744e-05
Pgp-inhibitor:	0.305
Pgp-substrate:	0.974
Human Intestinal Absorption (HIA):	0.981
20% Bioavailability (F20%):	0.173
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	91.04850769042969%
Volume Distribution (VD):	0.335
Pgp-substrate:	14.009160995483398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	2.397
Half-life (T1/2):	0.929

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.344
AMES Toxicity:	0.298
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.943
Carcinogencity:	0.337
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC104275

Natural Product ID:	NPC104275
*Common Name:**	(S)-Alpha-Terpinyl [Alpha-L-(2-O-Galloyl)Arabinofuranosyl]-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	[(2R,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxan-2-yl]methoxy]oxolan-3-yl] 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	ZPXRVNRKZYBYHR-KCVLAQGPSA-N
Standard InCHI:	InChI=1S/C28H40O14/c1-12-4-6-14(7-5-12)28(2,3)42-26-23(36)22(35)20(33)18(40-26)11-38-27-24(21(34)17(10-29)39-27)41-25(37)13-8-15(30)19(32)16(31)9-13/h4,8-9,14,17-18,20-24,26-27,29-36H,5-7,10-11H2,1-3H3/t14-,17+,18-,20-,21+,22+,23-,24-,26+,27-/m1/s1
SMILES:	OC[C@@H]1O[C@H]([C@@H]([C@H]1O)OC(=O)c1cc(O)c(c(c1)O)O)OC[C@H]1O[C@@H](OC([C@H]2CCC(=CC2)C)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452113
PubChem CID:	24879475
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0001251] Gallic acid and derivatives [CHEMONTID:0003539] Galloyl esters

*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
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869193]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Berries	n.a.	n.a.	PMID[18314960]
NPO15339	Artemisia afra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8843	Epipactis palustris	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2373	Popillia japonica	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15339	Artemisia afra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15243	Pimenta dioica	Species	Myrtaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	10500.0	nM	PMID[556287]

☑ 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 NPC104275 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	332
0.1-0.2	1252
0.2-0.3	2887
0.3-0.4	6195
0.4-0.5	9890
0.5-0.6	7708
0.6-0.7	7100
0.7-0.8	6719
0.8-0.85	494
0.85-0.9	105
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC4747
0.9866	High Similarity	NPC172920
0.9866	High Similarity	NPC156624
0.9359	High Similarity	NPC41009
0.9205	High Similarity	NPC92117
0.9205	High Similarity	NPC75945
0.9195	High Similarity	NPC108455
0.9139	High Similarity	NPC248257
0.9139	High Similarity	NPC120621
0.9133	High Similarity	NPC473867
0.9128	High Similarity	NPC229036
0.9103	High Similarity	NPC49173
0.9085	High Similarity	NPC140151
0.9	High Similarity	NPC475738
0.8974	High Similarity	NPC203757
0.897	High Similarity	NPC260300
0.897	High Similarity	NPC80360
0.897	High Similarity	NPC469418
0.8968	High Similarity	NPC205037
0.8968	High Similarity	NPC3746
0.8968	High Similarity	NPC44260
0.8968	High Similarity	NPC61152
0.8968	High Similarity	NPC16024
0.8916	High Similarity	NPC195114
0.8874	High Similarity	NPC226738
0.8874	High Similarity	NPC190587
0.8874	High Similarity	NPC22176
0.8874	High Similarity	NPC121573
0.8861	High Similarity	NPC1913
0.8861	High Similarity	NPC472860
0.8861	High Similarity	NPC226759
0.8859	High Similarity	NPC225036
0.8859	High Similarity	NPC12218
0.8859	High Similarity	NPC75763
0.8859	High Similarity	NPC105525
0.8848	High Similarity	NPC469354
0.8846	High Similarity	NPC310661
0.8846	High Similarity	NPC105827
0.8834	High Similarity	NPC476017
0.8805	High Similarity	NPC289811
0.8805	High Similarity	NPC160780
0.8792	High Similarity	NPC239943
0.878	High Similarity	NPC475058
0.8758	High Similarity	NPC14030
0.8758	High Similarity	NPC291957
0.875	High Similarity	NPC239966
0.875	High Similarity	NPC203020
0.875	High Similarity	NPC119125
0.875	High Similarity	NPC166277
0.875	High Similarity	NPC102367
0.8742	High Similarity	NPC238419
0.8742	High Similarity	NPC474010
0.8742	High Similarity	NPC172419
0.8742	High Similarity	NPC135222
0.8704	High Similarity	NPC470898
0.8704	High Similarity	NPC109990
0.8704	High Similarity	NPC100420
0.8696	High Similarity	NPC472859
0.8696	High Similarity	NPC25389
0.8696	High Similarity	NPC311803
0.8688	High Similarity	NPC318826
0.8688	High Similarity	NPC104222
0.8688	High Similarity	NPC74319
0.8688	High Similarity	NPC287872
0.8688	High Similarity	NPC210501
0.8688	High Similarity	NPC114791
0.8688	High Similarity	NPC141331
0.8679	High Similarity	NPC239019
0.8679	High Similarity	NPC247629
0.8654	High Similarity	NPC306343
0.8645	High Similarity	NPC142528
0.8645	High Similarity	NPC43123
0.8642	High Similarity	NPC145847
0.8642	High Similarity	NPC476011
0.8642	High Similarity	NPC33298
0.8642	High Similarity	NPC285108
0.8634	High Similarity	NPC289346
0.8634	High Similarity	NPC138993
0.8627	High Similarity	NPC114242
0.8627	High Similarity	NPC50221
0.8625	High Similarity	NPC187205
0.8623	High Similarity	NPC169645
0.8623	High Similarity	NPC84482
0.8623	High Similarity	NPC469438
0.8616	High Similarity	NPC475484
0.8591	High Similarity	NPC18646
0.859	High Similarity	NPC42464
0.8589	High Similarity	NPC469651
0.8581	High Similarity	NPC268366
0.858	High Similarity	NPC477627
0.858	High Similarity	NPC117943
0.858	High Similarity	NPC266365
0.858	High Similarity	NPC293568
0.8571	High Similarity	NPC473713
0.8562	High Similarity	NPC478250
0.8554	High Similarity	NPC212748
0.8554	High Similarity	NPC470272
0.8553	High Similarity	NPC194095
0.8553	High Similarity	NPC472128
0.8553	High Similarity	NPC472127
0.8553	High Similarity	NPC327032
0.8553	High Similarity	NPC191046
0.8545	High Similarity	NPC311389
0.8545	High Similarity	NPC470271
0.8537	High Similarity	NPC180586
0.8537	High Similarity	NPC475979
0.8537	High Similarity	NPC294722
0.8535	High Similarity	NPC267469
0.8535	High Similarity	NPC116292
0.8535	High Similarity	NPC87630
0.8535	High Similarity	NPC179128
0.8533	High Similarity	NPC156892
0.8529	High Similarity	NPC170203
0.8529	High Similarity	NPC188217
0.8528	High Similarity	NPC76687
0.8528	High Similarity	NPC90905
0.8528	High Similarity	NPC4013
0.8528	High Similarity	NPC148273
0.8519	High Similarity	NPC474936
0.8512	High Similarity	NPC171706
0.8503	High Similarity	NPC470685
0.8494	Intermediate Similarity	NPC21956
0.8494	Intermediate Similarity	NPC197708
0.8494	Intermediate Similarity	NPC658
0.8485	Intermediate Similarity	NPC301910
0.8485	Intermediate Similarity	NPC175793
0.8485	Intermediate Similarity	NPC469458
0.8485	Intermediate Similarity	NPC88176
0.8485	Intermediate Similarity	NPC149002
0.8485	Intermediate Similarity	NPC469419
0.8485	Intermediate Similarity	NPC469459
0.8485	Intermediate Similarity	NPC130730
0.8485	Intermediate Similarity	NPC469396
0.8481	Intermediate Similarity	NPC289021
0.8481	Intermediate Similarity	NPC158546
0.8466	Intermediate Similarity	NPC69868
0.8462	Intermediate Similarity	NPC79736
0.8462	Intermediate Similarity	NPC67629
0.8457	Intermediate Similarity	NPC469384
0.8457	Intermediate Similarity	NPC179914
0.8456	Intermediate Similarity	NPC156124
0.8456	Intermediate Similarity	NPC1321
0.8456	Intermediate Similarity	NPC304929
0.8452	Intermediate Similarity	NPC316539
0.8447	Intermediate Similarity	NPC471405
0.8438	Intermediate Similarity	NPC197188
0.8438	Intermediate Similarity	NPC43872
0.8438	Intermediate Similarity	NPC287504
0.8438	Intermediate Similarity	NPC291510
0.8438	Intermediate Similarity	NPC238672
0.8438	Intermediate Similarity	NPC144801
0.8438	Intermediate Similarity	NPC116850
0.8434	Intermediate Similarity	NPC43918
0.8434	Intermediate Similarity	NPC190204
0.8434	Intermediate Similarity	NPC116745
0.8434	Intermediate Similarity	NPC261411
0.8428	Intermediate Similarity	NPC203664
0.8428	Intermediate Similarity	NPC36130
0.8428	Intermediate Similarity	NPC221249
0.8428	Intermediate Similarity	NPC134905
0.8428	Intermediate Similarity	NPC289438
0.8424	Intermediate Similarity	NPC265600
0.8421	Intermediate Similarity	NPC220942
0.8418	Intermediate Similarity	NPC35160
0.8418	Intermediate Similarity	NPC162569
0.8412	Intermediate Similarity	NPC267549
0.8408	Intermediate Similarity	NPC81835
0.8405	Intermediate Similarity	NPC24627
0.8397	Intermediate Similarity	NPC208293
0.8397	Intermediate Similarity	NPC474465
0.8395	Intermediate Similarity	NPC190020
0.8395	Intermediate Similarity	NPC133984
0.8395	Intermediate Similarity	NPC84935
0.8395	Intermediate Similarity	NPC257309
0.8395	Intermediate Similarity	NPC286919
0.8395	Intermediate Similarity	NPC77679
0.8395	Intermediate Similarity	NPC478226
0.8395	Intermediate Similarity	NPC475663
0.8393	Intermediate Similarity	NPC261254
0.8393	Intermediate Similarity	NPC5786
0.8393	Intermediate Similarity	NPC102851
0.8393	Intermediate Similarity	NPC235575
0.8387	Intermediate Similarity	NPC77922
0.8387	Intermediate Similarity	NPC473281
0.8387	Intermediate Similarity	NPC297342
0.8385	Intermediate Similarity	NPC10205
0.8385	Intermediate Similarity	NPC145425
0.8385	Intermediate Similarity	NPC38699
0.8383	Intermediate Similarity	NPC328321
0.8383	Intermediate Similarity	NPC88557
0.8377	Intermediate Similarity	NPC296643
0.8375	Intermediate Similarity	NPC299706
0.8375	Intermediate Similarity	NPC115466
0.8375	Intermediate Similarity	NPC61604
0.8375	Intermediate Similarity	NPC245615
0.8375	Intermediate Similarity	NPC157898
0.8365	Intermediate Similarity	NPC32079
0.8365	Intermediate Similarity	NPC477700
0.8365	Intermediate Similarity	NPC252979
0.8364	Intermediate Similarity	NPC14294

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 NPC104275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	792
0.2-0.3	1812
0.3-0.4	2687
0.4-0.5	2124
0.5-0.6	1051
0.6-0.7	321
0.7-0.8	78
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8456	Intermediate Similarity	NPD230	Phase 1
0.8343	Intermediate Similarity	NPD7685	Pre-registration
0.8323	Intermediate Similarity	NPD7228	Approved
0.8323	Intermediate Similarity	NPD3818	Discontinued
0.8232	Intermediate Similarity	NPD6234	Discontinued
0.8221	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD37	Approved
0.8118	Intermediate Similarity	NPD7074	Phase 3
0.811	Intermediate Similarity	NPD4966	Approved
0.811	Intermediate Similarity	NPD4967	Phase 2
0.811	Intermediate Similarity	NPD4965	Approved
0.8089	Intermediate Similarity	NPD6190	Approved
0.8065	Intermediate Similarity	NPD7266	Discontinued
0.8059	Intermediate Similarity	NPD7054	Approved
0.8046	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7472	Approved
0.7977	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7251	Discontinued
0.7861	Intermediate Similarity	NPD6797	Phase 2
0.7844	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7240	Approved
0.7816	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD1653	Approved
0.7771	Intermediate Similarity	NPD7808	Phase 3
0.7759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD9269	Phase 2
0.7711	Intermediate Similarity	NPD1934	Approved
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7665	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5844	Phase 1
0.763	Intermediate Similarity	NPD7473	Discontinued
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3882	Suspended
0.7572	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6166	Phase 2
0.7572	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6232	Discontinued
0.7543	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7075	Discontinued
0.7515	Intermediate Similarity	NPD5353	Approved
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7473	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4628	Phase 3
0.7469	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2801	Approved
0.745	Intermediate Similarity	NPD9268	Approved
0.7442	Intermediate Similarity	NPD5494	Approved
0.7418	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3817	Phase 2
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7389	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD8166	Discontinued
0.7353	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7819	Suspended
0.7346	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD8312	Approved
0.7325	Intermediate Similarity	NPD3764	Approved
0.7316	Intermediate Similarity	NPD7680	Approved
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7306	Intermediate Similarity	NPD8151	Discontinued
0.7277	Intermediate Similarity	NPD8320	Phase 1
0.7277	Intermediate Similarity	NPD8319	Approved
0.7267	Intermediate Similarity	NPD9545	Approved
0.7233	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD943	Approved
0.7229	Intermediate Similarity	NPD1511	Approved
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7193	Intermediate Similarity	NPD6801	Discontinued
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7152	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD1512	Approved
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.7134	Intermediate Similarity	NPD9494	Approved
0.7118	Intermediate Similarity	NPD7458	Discontinued
0.711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5402	Approved
0.7095	Intermediate Similarity	NPD7799	Discontinued
0.7095	Intermediate Similarity	NPD3751	Discontinued
0.7076	Intermediate Similarity	NPD6599	Discontinued
0.7068	Intermediate Similarity	NPD6778	Approved
0.7068	Intermediate Similarity	NPD6782	Approved
0.7068	Intermediate Similarity	NPD6781	Approved
0.7068	Intermediate Similarity	NPD6780	Approved
0.7068	Intermediate Similarity	NPD6777	Approved
0.7068	Intermediate Similarity	NPD6776	Approved
0.7068	Intermediate Similarity	NPD6779	Approved
0.7062	Intermediate Similarity	NPD5710	Approved
0.7062	Intermediate Similarity	NPD5711	Approved
0.7056	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD8455	Phase 2
0.7048	Intermediate Similarity	NPD3750	Approved
0.7035	Intermediate Similarity	NPD7411	Suspended
0.703	Intermediate Similarity	NPD1549	Phase 2
0.7029	Intermediate Similarity	NPD3749	Approved
0.7024	Intermediate Similarity	NPD6799	Approved
0.7022	Intermediate Similarity	NPD5242	Approved
0.7019	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1613	Approved
0.7012	Intermediate Similarity	NPD6099	Approved
0.7012	Intermediate Similarity	NPD6100	Approved
0.7011	Intermediate Similarity	NPD8407	Phase 2
0.7006	Intermediate Similarity	NPD6959	Discontinued
0.7006	Intermediate Similarity	NPD8127	Discontinued
0.7005	Intermediate Similarity	NPD7874	Approved
0.7005	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7783	Phase 2
0.697	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7696	Phase 3
0.6959	Remote Similarity	NPD7698	Approved
0.6959	Remote Similarity	NPD7697	Approved
0.6951	Remote Similarity	NPD1510	Phase 2
0.694	Remote Similarity	NPD8368	Discontinued
0.6923	Remote Similarity	NPD7870	Phase 2
0.6923	Remote Similarity	NPD7871	Phase 2
0.6919	Remote Similarity	NPD3455	Phase 2
0.6907	Remote Similarity	NPD6823	Phase 2
0.6904	Remote Similarity	NPD7701	Phase 2
0.6904	Remote Similarity	NPD7585	Approved
0.6901	Remote Similarity	NPD5403	Approved
0.6894	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD919	Approved
0.6889	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7999	Approved
0.6886	Remote Similarity	NPD2800	Approved
0.6886	Remote Similarity	NPD6674	Discontinued
0.6884	Remote Similarity	NPD7801	Approved
0.6882	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7028	Phase 2
0.6875	Remote Similarity	NPD7768	Phase 2
0.6872	Remote Similarity	NPD3787	Discontinued
0.6871	Remote Similarity	NPD447	Suspended
0.6866	Remote Similarity	NPD7930	Approved
0.6853	Remote Similarity	NPD7583	Approved
0.6848	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6213	Phase 3
0.6842	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6212	Phase 3
0.6839	Remote Similarity	NPD6385	Approved
0.6839	Remote Similarity	NPD6386	Approved
0.6833	Remote Similarity	NPD3926	Phase 2
0.6832	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1607	Approved
0.6813	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1240	Approved
0.6807	Remote Similarity	NPD2796	Approved
0.6807	Remote Similarity	NPD2935	Discontinued
0.6807	Remote Similarity	NPD1551	Phase 2
0.679	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5401	Approved
0.6778	Remote Similarity	NPD7229	Phase 3
0.677	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7584	Approved
0.6768	Remote Similarity	NPD1933	Approved
0.6765	Remote Similarity	NPD7236	Approved
0.6752	Remote Similarity	NPD3705	Approved
0.6747	Remote Similarity	NPD3748	Approved
0.6746	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4110	Phase 3
0.6744	Remote Similarity	NPD6273	Approved
0.6727	Remote Similarity	NPD6651	Approved
0.6725	Remote Similarity	NPD7390	Discontinued
0.6724	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD1247	Approved
0.6705	Remote Similarity	NPD920	Approved
0.6687	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7097	Phase 1
0.6684	Remote Similarity	NPD8360	Approved
0.6684	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD4749	Approved
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7239	Suspended
0.6667	Remote Similarity	NPD5124	Phase 1
0.6667	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5760	Phase 2
0.665	Remote Similarity	NPD5006	Approved
0.665	Remote Similarity	NPD5005	Approved
0.6648	Remote Similarity	NPD7615	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