NPASS Compound

Structure

CID248903 OpenBabel06191716052D 49 53 0 0 1 0 0 0 0 0999 V2000 9.3532 -4.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4871 -1.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7551 -1.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3532 -1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8891 -1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6211 -2.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0743 -3.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 -0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6833 -3.4815 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 7.6211 -1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5743 -2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2435 -1.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0525 -2.9761 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3532 -2.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4871 -3.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8173 -2.9815 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 5.0230 -1.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8173 -1.9815 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 11.9512 -1.4815 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 11.0852 -1.9815 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 4.7956 -3.6452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0852 -2.9815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1570 -1.9815 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.5493 -2.9815 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 0.3090 -0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0230 -0.4815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.6833 -1.4815 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 11.9512 -0.4815 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 10.2192 -1.4815 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 4.5877 -4.6233 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7467 -3.3362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4871 -4.4815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2192 -3.4815 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 11.9512 -3.4815 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 45 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 17 1 0 0 0 0 5 22 1 0 0 0 0 6 12 2 0 0 0 0 6 19 1 0 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 33 1 0 0 0 0 11 34 1 0 0 0 0 13 14 1 0 0 0 0 14 32 1 0 0 0 0 15 29 1 6 0 0 0 15 32 1 0 0 0 0 16 18 2 0 0 0 0 16 35 1 0 0 0 0 17 19 2 0 0 0 0 17 46 1 0 0 0 0 18 47 1 0 0 0 0 19 45 1 0 0 0 0 20 10 1 1 0 0 0 20 23 1 0 0 0 0 20 48 1 0 0 0 0 21 11 1 6 0 0 0 21 24 1 0 0 0 0 21 49 1 0 0 0 0 22 32 1 0 0 0 0 22 36 2 0 0 0 0 23 25 1 0 0 0 0 23 37 1 6 0 0 0 24 26 1 0 0 0 0 24 38 1 1 0 0 0 25 27 1 0 0 0 0 25 39 1 1 0 0 0 26 28 1 0 0 0 0 26 40 1 6 0 0 0 27 30 1 0 0 0 0 27 41 1 6 0 0 0 28 31 1 0 0 0 0 28 42 1 1 0 0 0 29 43 2 0 0 0 0 29 44 1 0 0 0 0 30 46 1 1 0 0 0 30 48 1 0 0 0 0 31 47 1 6 0 0 0 31 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	695.21
Volume:	638.652
LogP:	-0.832
LogD:	-0.577
LogS:	-2.946
# Rotatable Bonds:	11
TPSA:	285.83
# H-Bond Aceptor:	18
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.11
Synthetic Accessibility Score:	4.946
Fsp3:	0.484
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.68
MDCK Permeability:	4.673820149037056e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.948
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.256
Plasma Protein Binding (PPB):	62.32172393798828%
Volume Distribution (VD):	0.432
Pgp-substrate:	19.82019805908203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	1.109
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.179
Human Hepatotoxicity (H-HT):	0.413
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.074
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC248903

Natural Product ID:	NPC248903
*Common Name:**	Oleracein D
IUPAC Name:	(2S)-5-hydroxy-1-[(E)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydroindole-2-carboxylic acid
Synonyms:
Standard InCHIKey:	GRIGERORCOQKIJ-PYCQGYPLSA-N
Standard InCHI:	InChI=1S/C31H37NO17/c1-45-19-6-12(2-4-17(19)46-30-27(41)25(39)23(37)20(10-33)48-30)3-5-22(36)32-14-9-18(16(35)8-13(14)7-15(32)29(43)44)47-31-28(42)26(40)24(38)21(11-34)49-31/h2-6,8-9,15,20-21,23-28,30-31,33-35,37-42H,7,10-11H2,1H3,(H,43,44)/b5-3+/t15-,20+,21+,23+,24+,25-,26-,27+,28+,30+,31+/m0/s1
SMILES:	COc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)/C=C/C(=O)N1c2cc(c(cc2C[C@H]1C(=O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3739685
PubChem CID:	21574475
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562741]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29517238]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31625751]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	Along the Valencian coast, Spain	2020-Jun&Jul	PMID[35161358]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Herb	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
EC50	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.		EC50	=	34550.0	nM	PMID[571147]

☑ 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 NPC248903 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	337
0.1-0.2	1689
0.2-0.3	5819
0.3-0.4	10973
0.4-0.5	8265
0.5-0.6	12145
0.6-0.7	3272
0.7-0.8	174
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.995	High Similarity	NPC26928
0.9801	High Similarity	NPC148124
0.9751	High Similarity	NPC99724
0.785	Intermediate Similarity	NPC268077
0.7804	Intermediate Similarity	NPC207971
0.7783	Intermediate Similarity	NPC291173
0.7783	Intermediate Similarity	NPC126556
0.7783	Intermediate Similarity	NPC267414
0.7778	Intermediate Similarity	NPC19175
0.7723	Intermediate Similarity	NPC128476
0.7723	Intermediate Similarity	NPC46259
0.7679	Intermediate Similarity	NPC318525
0.7679	Intermediate Similarity	NPC10653
0.7653	Intermediate Similarity	NPC50548
0.7639	Intermediate Similarity	NPC473460
0.7627	Intermediate Similarity	NPC477393
0.7617	Intermediate Similarity	NPC477395
0.7606	Intermediate Similarity	NPC144314
0.7602	Intermediate Similarity	NPC119722
0.7593	Intermediate Similarity	NPC311357
0.7591	Intermediate Similarity	NPC269449
0.757	Intermediate Similarity	NPC71124
0.7563	Intermediate Similarity	NPC477396
0.7559	Intermediate Similarity	NPC149962
0.7555	Intermediate Similarity	NPC473458
0.7535	Intermediate Similarity	NPC5374
0.7535	Intermediate Similarity	NPC123859
0.7524	Intermediate Similarity	NPC477186
0.7523	Intermediate Similarity	NPC470481
0.7523	Intermediate Similarity	NPC470482
0.7522	Intermediate Similarity	NPC476069
0.75	Intermediate Similarity	NPC242728
0.7467	Intermediate Similarity	NPC195636
0.7466	Intermediate Similarity	NPC471561
0.7465	Intermediate Similarity	NPC254957
0.7444	Intermediate Similarity	NPC127996
0.7444	Intermediate Similarity	NPC159815
0.7442	Intermediate Similarity	NPC472191
0.7435	Intermediate Similarity	NPC476436
0.7419	Intermediate Similarity	NPC127178
0.7401	Intermediate Similarity	NPC288110
0.7401	Intermediate Similarity	NPC108826
0.7399	Intermediate Similarity	NPC295479
0.7399	Intermediate Similarity	NPC220241
0.7399	Intermediate Similarity	NPC82541
0.7391	Intermediate Similarity	NPC287152
0.7387	Intermediate Similarity	NPC475133
0.7362	Intermediate Similarity	NPC476220
0.7362	Intermediate Similarity	NPC160113
0.7361	Intermediate Similarity	NPC24228
0.7358	Intermediate Similarity	NPC230098
0.7357	Intermediate Similarity	NPC87560
0.7357	Intermediate Similarity	NPC195120
0.7357	Intermediate Similarity	NPC182853
0.7336	Intermediate Similarity	NPC118189
0.7333	Intermediate Similarity	NPC217903
0.7328	Intermediate Similarity	NPC471513
0.7315	Intermediate Similarity	NPC33256
0.7309	Intermediate Similarity	NPC477160
0.7293	Intermediate Similarity	NPC118154
0.7293	Intermediate Similarity	NPC157983
0.7289	Intermediate Similarity	NPC10732
0.7289	Intermediate Similarity	NPC116178
0.7285	Intermediate Similarity	NPC475147
0.7277	Intermediate Similarity	NPC476429
0.7265	Intermediate Similarity	NPC477397
0.7261	Intermediate Similarity	NPC76478
0.7241	Intermediate Similarity	NPC231924
0.7238	Intermediate Similarity	NPC304837
0.7238	Intermediate Similarity	NPC476258
0.7238	Intermediate Similarity	NPC329816
0.7237	Intermediate Similarity	NPC328856
0.7237	Intermediate Similarity	NPC314914
0.7237	Intermediate Similarity	NPC478046
0.7237	Intermediate Similarity	NPC321226
0.7237	Intermediate Similarity	NPC180210
0.7237	Intermediate Similarity	NPC478047
0.7235	Intermediate Similarity	NPC477258
0.7225	Intermediate Similarity	NPC55470
0.7207	Intermediate Similarity	NPC473422
0.7205	Intermediate Similarity	NPC134702
0.7205	Intermediate Similarity	NPC284236
0.7205	Intermediate Similarity	NPC316368
0.7204	Intermediate Similarity	NPC474745
0.7202	Intermediate Similarity	NPC161804
0.7196	Intermediate Similarity	NPC162694
0.7193	Intermediate Similarity	NPC478048
0.7193	Intermediate Similarity	NPC471531
0.719	Intermediate Similarity	NPC5167
0.7188	Intermediate Similarity	NPC257728
0.7183	Intermediate Similarity	NPC475981
0.7183	Intermediate Similarity	NPC474746
0.7182	Intermediate Similarity	NPC475654
0.7181	Intermediate Similarity	NPC321166
0.7179	Intermediate Similarity	NPC470480
0.7178	Intermediate Similarity	NPC469722
0.7177	Intermediate Similarity	NPC2314
0.7169	Intermediate Similarity	NPC124302
0.7169	Intermediate Similarity	NPC73020
0.7169	Intermediate Similarity	NPC14622
0.7169	Intermediate Similarity	NPC46744
0.7169	Intermediate Similarity	NPC70290
0.7169	Intermediate Similarity	NPC215098
0.7156	Intermediate Similarity	NPC153365
0.7156	Intermediate Similarity	NPC474325
0.7155	Intermediate Similarity	NPC71539
0.7155	Intermediate Similarity	NPC250960
0.7143	Intermediate Similarity	NPC257266
0.7143	Intermediate Similarity	NPC320064
0.7143	Intermediate Similarity	NPC198160
0.7143	Intermediate Similarity	NPC49353
0.7143	Intermediate Similarity	NPC94499
0.7143	Intermediate Similarity	NPC170101
0.7137	Intermediate Similarity	NPC266994
0.713	Intermediate Similarity	NPC77777
0.713	Intermediate Similarity	NPC87714
0.7123	Intermediate Similarity	NPC32154
0.7118	Intermediate Similarity	NPC234772
0.7117	Intermediate Similarity	NPC202771
0.7117	Intermediate Similarity	NPC2173
0.7117	Intermediate Similarity	NPC328700
0.7117	Intermediate Similarity	NPC119818
0.7113	Intermediate Similarity	NPC154922
0.7111	Intermediate Similarity	NPC207873
0.7111	Intermediate Similarity	NPC100573
0.7109	Intermediate Similarity	NPC85613
0.7109	Intermediate Similarity	NPC237044
0.7109	Intermediate Similarity	NPC474470
0.7104	Intermediate Similarity	NPC314100
0.7104	Intermediate Similarity	NPC226652
0.7104	Intermediate Similarity	NPC120671
0.7104	Intermediate Similarity	NPC72788
0.7103	Intermediate Similarity	NPC262725
0.71	Intermediate Similarity	NPC222046
0.709	Intermediate Similarity	NPC120239
0.7089	Intermediate Similarity	NPC473562
0.7083	Intermediate Similarity	NPC174122
0.7083	Intermediate Similarity	NPC314702
0.7083	Intermediate Similarity	NPC64140
0.708	Intermediate Similarity	NPC168250
0.7078	Intermediate Similarity	NPC188400
0.7076	Intermediate Similarity	NPC74216
0.7076	Intermediate Similarity	NPC315914
0.7062	Intermediate Similarity	NPC304675
0.7056	Intermediate Similarity	NPC82056
0.7039	Intermediate Similarity	NPC329830
0.7037	Intermediate Similarity	NPC113455
0.7037	Intermediate Similarity	NPC477259
0.7037	Intermediate Similarity	NPC234069
0.7037	Intermediate Similarity	NPC169387
0.7034	Intermediate Similarity	NPC13249
0.7031	Intermediate Similarity	NPC114468
0.7031	Intermediate Similarity	NPC268223
0.7028	Intermediate Similarity	NPC241704
0.7026	Intermediate Similarity	NPC475609
0.7023	Intermediate Similarity	NPC276120
0.7022	Intermediate Similarity	NPC475768
0.7022	Intermediate Similarity	NPC80472
0.7021	Intermediate Similarity	NPC477394
0.7021	Intermediate Similarity	NPC122886
0.7019	Intermediate Similarity	NPC474858
0.7019	Intermediate Similarity	NPC329717
0.7018	Intermediate Similarity	NPC471532
0.7018	Intermediate Similarity	NPC473004
0.7018	Intermediate Similarity	NPC226708
0.7014	Intermediate Similarity	NPC193906
0.7014	Intermediate Similarity	NPC23080
0.7014	Intermediate Similarity	NPC17677
0.7013	Intermediate Similarity	NPC313327
0.7008	Intermediate Similarity	NPC313627
0.7005	Intermediate Similarity	NPC141440
0.7005	Intermediate Similarity	NPC29531
0.7005	Intermediate Similarity	NPC237579
0.7	Intermediate Similarity	NPC162653
0.7	Intermediate Similarity	NPC148391
0.7	Intermediate Similarity	NPC2905
0.6991	Remote Similarity	NPC11708
0.6991	Remote Similarity	NPC16249
0.6991	Remote Similarity	NPC478075
0.6986	Remote Similarity	NPC471825
0.6981	Remote Similarity	NPC187678
0.6977	Remote Similarity	NPC116284
0.6971	Remote Similarity	NPC35345
0.6967	Remote Similarity	NPC470739
0.6967	Remote Similarity	NPC477640
0.6967	Remote Similarity	NPC225597
0.6966	Remote Similarity	NPC7560
0.6957	Remote Similarity	NPC24954
0.6953	Remote Similarity	NPC219397
0.6952	Remote Similarity	NPC477185
0.6951	Remote Similarity	NPC138830
0.6951	Remote Similarity	NPC67904
0.6948	Remote Similarity	NPC32064
0.6947	Remote Similarity	NPC195787
0.6947	Remote Similarity	NPC246140
0.6946	Remote Similarity	NPC471073
0.6946	Remote Similarity	NPC270811
0.6944	Remote Similarity	NPC129897
0.6944	Remote Similarity	NPC116007
0.6944	Remote Similarity	NPC291759

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 NPC248903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	609
0.2-0.3	1011
0.3-0.4	1972
0.4-0.5	2752
0.5-0.6	2025
0.6-0.7	545
0.7-0.8	23
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
0.7725	Intermediate Similarity	NPD5582	Discontinued
0.7543	Intermediate Similarity	NPD6625	Approved
0.7512	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.7359	Intermediate Similarity	NPD7186	Phase 3
0.7339	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4846	Phase 2
0.7251	Intermediate Similarity	NPD7280	Phase 3
0.7251	Intermediate Similarity	NPD7281	Phase 3
0.7249	Intermediate Similarity	NPD2899	Discontinued
0.722	Intermediate Similarity	NPD7263	Phase 2
0.7198	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7585	Approved
0.7173	Intermediate Similarity	NPD6723	Discontinued
0.7169	Intermediate Similarity	NPD4420	Approved
0.7156	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7583	Approved
0.7137	Intermediate Similarity	NPD7223	Discontinued
0.7137	Intermediate Similarity	NPD7224	Discontinued
0.7123	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5005	Approved
0.7117	Intermediate Similarity	NPD5006	Approved
0.7093	Intermediate Similarity	NPD683	Approved
0.7091	Intermediate Similarity	NPD5071	Phase 2
0.7085	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD6997	Phase 2
0.7074	Intermediate Similarity	NPD7559	Phase 2
0.7056	Intermediate Similarity	NPD6853	Approved
0.7056	Intermediate Similarity	NPD6851	Approved
0.7051	Intermediate Similarity	NPD3912	Discontinued
0.7028	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7560	Approved
0.7005	Intermediate Similarity	NPD2843	Phase 2
0.7005	Intermediate Similarity	NPD2845	Phase 2
0.6996	Remote Similarity	NPD3437	Discontinued
0.6991	Remote Similarity	NPD7584	Approved
0.6982	Remote Similarity	NPD6874	Approved
0.6972	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7805	Phase 3
0.696	Remote Similarity	NPD4859	Phase 1
0.696	Remote Similarity	NPD8027	Approved
0.6948	Remote Similarity	NPD6297	Approved
0.6944	Remote Similarity	NPD7955	Approved
0.6944	Remote Similarity	NPD7956	Approved
0.6937	Remote Similarity	NPD6877	Discontinued
0.6923	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4885	Approved
0.6907	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7047	Phase 3
0.6895	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7048	Phase 3
0.6854	Remote Similarity	NPD5313	Approved
0.6854	Remote Similarity	NPD5312	Approved
0.6854	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2978	Approved
0.6845	Remote Similarity	NPD2977	Approved
0.6844	Remote Similarity	NPD2494	Approved
0.6844	Remote Similarity	NPD2493	Approved
0.6844	Remote Similarity	NPD3450	Approved
0.6844	Remote Similarity	NPD3452	Approved
0.6837	Remote Similarity	NPD7038	Approved
0.6837	Remote Similarity	NPD7039	Approved
0.683	Remote Similarity	NPD7811	Phase 3
0.683	Remote Similarity	NPD7810	Phase 3
0.6824	Remote Similarity	NPD8149	Discontinued
0.6824	Remote Similarity	NPD5025	Approved
0.6809	Remote Similarity	NPD7803	Approved
0.6807	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8461	Discontinued
0.6767	Remote Similarity	NPD7827	Phase 1
0.6761	Remote Similarity	NPD6716	Phase 1
0.6758	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD1880	Phase 3
0.6754	Remote Similarity	NPD4582	Approved
0.6754	Remote Similarity	NPD3298	Approved
0.6754	Remote Similarity	NPD6644	Discontinued
0.6754	Remote Similarity	NPD4583	Approved
0.6746	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3441	Approved
0.6736	Remote Similarity	NPD3442	Approved
0.673	Remote Similarity	NPD6457	Approved
0.6727	Remote Similarity	NPD7906	Approved
0.6726	Remote Similarity	NPD5457	Discontinued
0.6725	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8463	Approved
0.6713	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7296	Approved
0.6711	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4002	Approved
0.6711	Remote Similarity	NPD4004	Approved
0.6697	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6238	Discontinued
0.6694	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7125	Discontinued
0.6681	Remote Similarity	NPD5562	Approved
0.6681	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5561	Approved
0.668	Remote Similarity	NPD7886	Phase 2
0.668	Remote Similarity	NPD7885	Phase 2
0.668	Remote Similarity	NPD7859	Phase 2
0.6667	Remote Similarity	NPD8152	Approved
0.6667	Remote Similarity	NPD2490	Approved
0.6667	Remote Similarity	NPD6385	Approved
0.6667	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2975	Approved
0.6667	Remote Similarity	NPD2973	Approved
0.6667	Remote Similarity	NPD8153	Approved
0.6667	Remote Similarity	NPD2974	Approved
0.6667	Remote Similarity	NPD2488	Approved
0.6667	Remote Similarity	NPD8255	Phase 2
0.6667	Remote Similarity	NPD6386	Approved
0.6654	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD7708	Approved
0.6652	Remote Similarity	NPD6493	Phase 3
0.6651	Remote Similarity	NPD2821	Approved
0.6651	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4668	Phase 2
0.6625	Remote Similarity	NPD7820	Phase 3
0.6623	Remote Similarity	NPD7476	Discontinued
0.6623	Remote Similarity	NPD6296	Discontinued
0.6623	Remote Similarity	NPD6321	Discontinued
0.662	Remote Similarity	NPD5183	Approved
0.662	Remote Similarity	NPD5186	Approved
0.662	Remote Similarity	NPD3793	Phase 3
0.6611	Remote Similarity	NPD7907	Approved
0.6609	Remote Similarity	NPD4467	Phase 2
0.6609	Remote Similarity	NPD4465	Phase 2
0.6609	Remote Similarity	NPD7891	Discontinued
0.6606	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5772	Approved
0.6603	Remote Similarity	NPD5773	Approved
0.6598	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5496	Approved
0.6596	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8054	Approved
0.6591	Remote Similarity	NPD8053	Approved
0.6591	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5137	Approved
0.6579	Remote Similarity	NPD4580	Approved
0.6579	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7256	Discontinued
0.6578	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.657	Remote Similarity	NPD824	Approved
0.6569	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3591	Approved
0.6567	Remote Similarity	NPD3592	Approved
0.6565	Remote Similarity	NPD6669	Phase 2
0.6564	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7279	Phase 2
0.6556	Remote Similarity	NPD7278	Phase 2
0.6556	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7225	Discontinued
0.6553	Remote Similarity	NPD5866	Approved
0.6549	Remote Similarity	NPD3964	Approved
0.6548	Remote Similarity	NPD8359	Phase 2
0.6547	Remote Similarity	NPD5928	Phase 1
0.6538	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3296	Phase 1
0.6538	Remote Similarity	NPD5860	Discontinued
0.6535	Remote Similarity	NPD3297	Approved
0.6535	Remote Similarity	NPD7565	Approved
0.6533	Remote Similarity	NPD5150	Phase 2
0.6532	Remote Similarity	NPD4663	Approved
0.653	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5677	Discontinued
0.6526	Remote Similarity	NPD2904	Discontinued
0.6524	Remote Similarity	NPD2906	Approved
0.6524	Remote Similarity	NPD2907	Approved
0.6522	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.652	Remote Similarity	NPD4605	Approved
0.652	Remote Similarity	NPD7417	Discontinued
0.652	Remote Similarity	NPD4604	Approved
0.6517	Remote Similarity	NPD7266	Discontinued
0.6515	Remote Similarity	NPD4049	Phase 2
0.6515	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7479	Phase 2
0.6514	Remote Similarity	NPD7472	Approved
0.6512	Remote Similarity	NPD5242	Approved
0.6504	Remote Similarity	NPD7797	Approved
0.6504	Remote Similarity	NPD7796	Approved
0.6502	Remote Similarity	NPD7291	Discontinued
0.6495	Remote Similarity	NPD6107	Approved
0.6494	Remote Similarity	NPD6517	Phase 3
0.649	Remote Similarity	NPD4981	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