NPASS Compound

Structure

CID26928 OpenBabel06191715352D 47 51 0 0 1 0 0 0 0 0999 V2000 7.2985 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6586 2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0113 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2767 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6368 3.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7023 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 13.2185 3.1802 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 6.9895 3.6270 0.0000 C 0 0 0 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 8.9458 4.0428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 0.5000 0.0000 C 0 0 1 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2403 2.9723 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 4.7242 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9313 2.0213 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9532 1.8133 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2840 2.5565 0.0000 C 0 0 2 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 6.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5931 3.5075 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 13.8876 2.4371 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0550 3.0032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6005 1.2781 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 10.6442 0.8623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3059 2.3486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5029 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5029 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9239 4.2507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5712 3.7155 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 4 1 0 0 0 0 1 12 2 0 0 0 0 2 5 2 0 0 0 0 2 12 1 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 14 2 0 0 0 0 5 14 1 0 0 0 0 6 21 1 0 0 0 0 7 13 1 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 32 1 0 0 0 0 11 33 1 0 0 0 0 13 15 1 0 0 0 0 14 44 1 0 0 0 0 15 31 1 0 0 0 0 16 28 1 6 0 0 0 16 31 1 0 0 0 0 17 18 2 0 0 0 0 17 34 1 0 0 0 0 18 45 1 0 0 0 0 19 10 1 6 0 0 0 19 22 1 0 0 0 0 19 46 1 0 0 0 0 20 11 1 6 0 0 0 20 23 1 0 0 0 0 20 47 1 0 0 0 0 21 31 1 0 0 0 0 21 35 2 0 0 0 0 22 24 1 0 0 0 0 22 36 1 1 0 0 0 23 25 1 0 0 0 0 23 37 1 1 0 0 0 24 26 1 0 0 0 0 24 38 1 6 0 0 0 25 27 1 0 0 0 0 25 39 1 6 0 0 0 26 29 1 0 0 0 0 26 40 1 1 0 0 0 27 30 1 0 0 0 0 27 41 1 1 0 0 0 28 42 2 0 0 0 0 28 43 1 0 0 0 0 29 44 1 6 0 0 0 29 46 1 0 0 0 0 30 45 1 6 0 0 0 30 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	665.2
Volume:	612.566
LogP:	-0.936
LogD:	-0.588
LogS:	-3.139
# Rotatable Bonds:	10
TPSA:	276.6
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.118
Synthetic Accessibility Score:	4.885
Fsp3:	0.467
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:	-6.66
MDCK Permeability:	3.592549546738155e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.931
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.256
Plasma Protein Binding (PPB):	76.23514556884766%
Volume Distribution (VD):	0.428
Pgp-substrate:	13.561826705932617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.256
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	1.217
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.177
Human Hepatotoxicity (H-HT):	0.431
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.194
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC26928

Natural Product ID:	NPC26928
*Common Name:**	Oleracein C
IUPAC Name:	(2S)-5-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-[(E)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]-2,3-dihydroindole-2-carboxylic acid
Synonyms:
Standard InCHIKey:	FDKIQKZQSBQELL-DBIVONCISA-N
Standard InCHI:	InChI=1S/C30H35NO16/c32-10-19-22(36)24(38)26(40)29(46-19)44-14-4-1-12(2-5-14)3-6-21(35)31-15-9-18(17(34)8-13(15)7-16(31)28(42)43)45-30-27(41)25(39)23(37)20(11-33)47-30/h1-6,8-9,16,19-20,22-27,29-30,32-34,36-41H,7,10-11H2,(H,42,43)/b6-3+/t16-,19+,20+,22+,23+,24-,25-,26+,27+,29+,30+/m0/s1
SMILES:	c1cc(ccc1/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)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3741758
PubChem CID:	21574474
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	=	38280.0	nM	PMID[573539]

☑ 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 NPC26928 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	370
0.1-0.2	1763
0.2-0.3	6209
0.3-0.4	10956
0.4-0.5	8292
0.5-0.6	11855
0.6-0.7	3067
0.7-0.8	163
0.8-0.85	8
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	NPC248903
0.98	High Similarity	NPC99724
0.9751	High Similarity	NPC148124
0.7804	Intermediate Similarity	NPC268077
0.7758	Intermediate Similarity	NPC46259
0.7757	Intermediate Similarity	NPC207971
0.7739	Intermediate Similarity	NPC291173
0.7738	Intermediate Similarity	NPC126556
0.7736	Intermediate Similarity	NPC267414
0.7733	Intermediate Similarity	NPC19175
0.7679	Intermediate Similarity	NPC128476
0.7634	Intermediate Similarity	NPC318525
0.7634	Intermediate Similarity	NPC10653
0.7606	Intermediate Similarity	NPC50548
0.7593	Intermediate Similarity	NPC473460
0.7585	Intermediate Similarity	NPC477393
0.7574	Intermediate Similarity	NPC477395
0.757	Intermediate Similarity	NPC5374
0.7559	Intermediate Similarity	NPC144314
0.7557	Intermediate Similarity	NPC119722
0.7546	Intermediate Similarity	NPC311357
0.7545	Intermediate Similarity	NPC269449
0.7523	Intermediate Similarity	NPC71124
0.7521	Intermediate Similarity	NPC477396
0.7512	Intermediate Similarity	NPC149962
0.7511	Intermediate Similarity	NPC473458
0.7488	Intermediate Similarity	NPC123859
0.7478	Intermediate Similarity	NPC476069
0.7477	Intermediate Similarity	NPC470481
0.7477	Intermediate Similarity	NPC470482
0.7476	Intermediate Similarity	NPC477186
0.7454	Intermediate Similarity	NPC242728
0.7432	Intermediate Similarity	NPC82541
0.7422	Intermediate Similarity	NPC195636
0.7421	Intermediate Similarity	NPC471561
0.7418	Intermediate Similarity	NPC254957
0.7399	Intermediate Similarity	NPC127996
0.7399	Intermediate Similarity	NPC159815
0.7395	Intermediate Similarity	NPC472191
0.7391	Intermediate Similarity	NPC476436
0.7373	Intermediate Similarity	NPC127178
0.7357	Intermediate Similarity	NPC108826
0.7357	Intermediate Similarity	NPC288110
0.7354	Intermediate Similarity	NPC220241
0.7354	Intermediate Similarity	NPC295479
0.7343	Intermediate Similarity	NPC287152
0.7342	Intermediate Similarity	NPC475133
0.7319	Intermediate Similarity	NPC160113
0.7319	Intermediate Similarity	NPC476220
0.7315	Intermediate Similarity	NPC24228
0.7313	Intermediate Similarity	NPC195120
0.7313	Intermediate Similarity	NPC87560
0.7313	Intermediate Similarity	NPC182853
0.7311	Intermediate Similarity	NPC230098
0.7293	Intermediate Similarity	NPC118189
0.7289	Intermediate Similarity	NPC217903
0.7284	Intermediate Similarity	NPC471513
0.7269	Intermediate Similarity	NPC33256
0.7265	Intermediate Similarity	NPC477160
0.7249	Intermediate Similarity	NPC118154
0.7249	Intermediate Similarity	NPC157983
0.7244	Intermediate Similarity	NPC10732
0.7244	Intermediate Similarity	NPC116178
0.724	Intermediate Similarity	NPC475147
0.7234	Intermediate Similarity	NPC476429
0.7222	Intermediate Similarity	NPC477397
0.7217	Intermediate Similarity	NPC76478
0.7198	Intermediate Similarity	NPC231924
0.7197	Intermediate Similarity	NPC476258
0.7197	Intermediate Similarity	NPC304837
0.7193	Intermediate Similarity	NPC180210
0.7193	Intermediate Similarity	NPC478046
0.7193	Intermediate Similarity	NPC478047
0.7193	Intermediate Similarity	NPC321226
0.7193	Intermediate Similarity	NPC328856
0.7193	Intermediate Similarity	NPC314914
0.719	Intermediate Similarity	NPC329816
0.7189	Intermediate Similarity	NPC477258
0.7181	Intermediate Similarity	NPC55470
0.7162	Intermediate Similarity	NPC473422
0.7162	Intermediate Similarity	NPC134702
0.7162	Intermediate Similarity	NPC284236
0.7162	Intermediate Similarity	NPC316368
0.7156	Intermediate Similarity	NPC474745
0.7156	Intermediate Similarity	NPC161804
0.715	Intermediate Similarity	NPC162694
0.7149	Intermediate Similarity	NPC471531
0.7149	Intermediate Similarity	NPC478048
0.7143	Intermediate Similarity	NPC5167
0.7143	Intermediate Similarity	NPC257728
0.7137	Intermediate Similarity	NPC321166
0.7137	Intermediate Similarity	NPC470480
0.7137	Intermediate Similarity	NPC469722
0.7136	Intermediate Similarity	NPC474746
0.7136	Intermediate Similarity	NPC475654
0.7136	Intermediate Similarity	NPC475981
0.7129	Intermediate Similarity	NPC2314
0.7123	Intermediate Similarity	NPC70290
0.7123	Intermediate Similarity	NPC73020
0.7123	Intermediate Similarity	NPC14622
0.7123	Intermediate Similarity	NPC46744
0.7123	Intermediate Similarity	NPC215098
0.7123	Intermediate Similarity	NPC124302
0.7112	Intermediate Similarity	NPC250960
0.7112	Intermediate Similarity	NPC71539
0.7111	Intermediate Similarity	NPC153365
0.7109	Intermediate Similarity	NPC474325
0.71	Intermediate Similarity	NPC170101
0.7098	Intermediate Similarity	NPC257266
0.7098	Intermediate Similarity	NPC198160
0.7097	Intermediate Similarity	NPC94499
0.7095	Intermediate Similarity	NPC49353
0.7094	Intermediate Similarity	NPC320064
0.7094	Intermediate Similarity	NPC266994
0.7087	Intermediate Similarity	NPC77777
0.7085	Intermediate Similarity	NPC87714
0.7075	Intermediate Similarity	NPC32154
0.7074	Intermediate Similarity	NPC234772
0.7072	Intermediate Similarity	NPC328700
0.7072	Intermediate Similarity	NPC119818
0.7072	Intermediate Similarity	NPC2173
0.7072	Intermediate Similarity	NPC202771
0.7071	Intermediate Similarity	NPC154922
0.7067	Intermediate Similarity	NPC100573
0.7067	Intermediate Similarity	NPC207873
0.7062	Intermediate Similarity	NPC237044
0.7062	Intermediate Similarity	NPC85613
0.7062	Intermediate Similarity	NPC474470
0.7059	Intermediate Similarity	NPC226652
0.7059	Intermediate Similarity	NPC72788
0.7059	Intermediate Similarity	NPC120671
0.7059	Intermediate Similarity	NPC314100
0.7056	Intermediate Similarity	NPC222046
0.7056	Intermediate Similarity	NPC262725
0.7054	Intermediate Similarity	NPC475768
0.7049	Intermediate Similarity	NPC120239
0.7042	Intermediate Similarity	NPC314702
0.7042	Intermediate Similarity	NPC473562
0.7037	Intermediate Similarity	NPC174122
0.7037	Intermediate Similarity	NPC64140
0.7037	Intermediate Similarity	NPC188400
0.7035	Intermediate Similarity	NPC168250
0.7034	Intermediate Similarity	NPC315914
0.7034	Intermediate Similarity	NPC74216
0.7014	Intermediate Similarity	NPC304675
0.7013	Intermediate Similarity	NPC82056
0.6996	Remote Similarity	NPC113455
0.6996	Remote Similarity	NPC329830
0.6992	Remote Similarity	NPC13249
0.6991	Remote Similarity	NPC234069
0.6991	Remote Similarity	NPC169387
0.6991	Remote Similarity	NPC477259
0.6987	Remote Similarity	NPC114468
0.6987	Remote Similarity	NPC268223
0.6986	Remote Similarity	NPC477185
0.6983	Remote Similarity	NPC475609
0.6981	Remote Similarity	NPC241704
0.698	Remote Similarity	NPC471073
0.698	Remote Similarity	NPC270811
0.6979	Remote Similarity	NPC477394
0.6979	Remote Similarity	NPC122886
0.6978	Remote Similarity	NPC80472
0.6977	Remote Similarity	NPC276120
0.6974	Remote Similarity	NPC471532
0.6972	Remote Similarity	NPC473004
0.6972	Remote Similarity	NPC226708
0.6971	Remote Similarity	NPC474858
0.6971	Remote Similarity	NPC329717
0.697	Remote Similarity	NPC313327
0.6969	Remote Similarity	NPC313627
0.6968	Remote Similarity	NPC23080
0.6968	Remote Similarity	NPC17677
0.6968	Remote Similarity	NPC193906
0.6967	Remote Similarity	NPC477187
0.6959	Remote Similarity	NPC141440
0.6959	Remote Similarity	NPC237579
0.6959	Remote Similarity	NPC29531
0.6957	Remote Similarity	NPC148391
0.6957	Remote Similarity	NPC2905
0.6955	Remote Similarity	NPC162653
0.6955	Remote Similarity	NPC99891
0.6952	Remote Similarity	NPC474475
0.6952	Remote Similarity	NPC311991
0.6948	Remote Similarity	NPC15919
0.6947	Remote Similarity	NPC16249
0.6947	Remote Similarity	NPC11708
0.6947	Remote Similarity	NPC478075
0.6941	Remote Similarity	NPC471825
0.6934	Remote Similarity	NPC187678
0.693	Remote Similarity	NPC133591
0.693	Remote Similarity	NPC116284
0.6923	Remote Similarity	NPC7560
0.6923	Remote Similarity	NPC35345
0.6919	Remote Similarity	NPC477640
0.6919	Remote Similarity	NPC225597
0.6919	Remote Similarity	NPC470739
0.691	Remote Similarity	NPC219397
0.6908	Remote Similarity	NPC24954
0.6906	Remote Similarity	NPC67904
0.6906	Remote Similarity	NPC138830

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 NPC26928 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	623
0.2-0.3	1047
0.3-0.4	2006
0.4-0.5	2737
0.5-0.6	1994
0.6-0.7	509
0.7-0.8	16
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
0.7678	Intermediate Similarity	NPD5582	Discontinued
0.75	Intermediate Similarity	NPD6625	Approved
0.7465	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7186	Phase 3
0.7331	Intermediate Similarity	NPD4846	Phase 2
0.7294	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2899	Discontinued
0.7204	Intermediate Similarity	NPD7281	Phase 3
0.7204	Intermediate Similarity	NPD7280	Phase 3
0.7175	Intermediate Similarity	NPD7263	Phase 2
0.715	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7585	Approved
0.7131	Intermediate Similarity	NPD6723	Discontinued
0.7123	Intermediate Similarity	NPD4420	Approved
0.7112	Intermediate Similarity	NPD6997	Phase 2
0.711	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7583	Approved
0.7094	Intermediate Similarity	NPD7224	Discontinued
0.7094	Intermediate Similarity	NPD7223	Discontinued
0.7078	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5005	Approved
0.7072	Intermediate Similarity	NPD5006	Approved
0.7048	Intermediate Similarity	NPD683	Approved
0.7045	Intermediate Similarity	NPD5071	Phase 2
0.704	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2845	Phase 2
0.7037	Intermediate Similarity	NPD2843	Phase 2
0.7031	Intermediate Similarity	NPD7559	Phase 2
0.7009	Intermediate Similarity	NPD6851	Approved
0.7009	Intermediate Similarity	NPD3912	Discontinued
0.7009	Intermediate Similarity	NPD6853	Approved
0.6983	Remote Similarity	NPD7560	Approved
0.6983	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6877	Discontinued
0.6955	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3437	Discontinued
0.6947	Remote Similarity	NPD7584	Approved
0.6937	Remote Similarity	NPD6874	Approved
0.6927	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7805	Phase 3
0.6916	Remote Similarity	NPD8027	Approved
0.6916	Remote Similarity	NPD4859	Phase 1
0.6905	Remote Similarity	NPD7955	Approved
0.6905	Remote Similarity	NPD7956	Approved
0.6901	Remote Similarity	NPD6297	Approved
0.6875	Remote Similarity	NPD3452	Approved
0.6875	Remote Similarity	NPD4885	Approved
0.6875	Remote Similarity	NPD3450	Approved
0.6864	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7047	Phase 3
0.6849	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7048	Phase 3
0.6828	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD5313	Approved
0.6808	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD5312	Approved
0.6804	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2493	Approved
0.68	Remote Similarity	NPD2494	Approved
0.6796	Remote Similarity	NPD2978	Approved
0.6796	Remote Similarity	NPD2977	Approved
0.6791	Remote Similarity	NPD7038	Approved
0.6791	Remote Similarity	NPD7039	Approved
0.6786	Remote Similarity	NPD7811	Phase 3
0.6786	Remote Similarity	NPD7810	Phase 3
0.6786	Remote Similarity	NPD1880	Phase 3
0.6781	Remote Similarity	NPD5025	Approved
0.6781	Remote Similarity	NPD8149	Discontinued
0.677	Remote Similarity	NPD7803	Approved
0.6765	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD5457	Discontinued
0.674	Remote Similarity	NPD4004	Approved
0.674	Remote Similarity	NPD4002	Approved
0.6732	Remote Similarity	NPD8461	Discontinued
0.6724	Remote Similarity	NPD7827	Phase 1
0.6721	Remote Similarity	NPD6716	Phase 1
0.6712	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4582	Approved
0.6711	Remote Similarity	NPD3298	Approved
0.6711	Remote Similarity	NPD6644	Discontinued
0.6711	Remote Similarity	NPD4583	Approved
0.6699	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3441	Approved
0.6694	Remote Similarity	NPD3442	Approved
0.6682	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6457	Approved
0.6682	Remote Similarity	NPD6493	Phase 3
0.6682	Remote Similarity	NPD7906	Approved
0.6681	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8463	Approved
0.6667	Remote Similarity	NPD7296	Approved
0.6667	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6238	Discontinued
0.664	Remote Similarity	NPD7859	Phase 2
0.664	Remote Similarity	NPD7885	Phase 2
0.664	Remote Similarity	NPD7886	Phase 2
0.6638	Remote Similarity	NPD5561	Approved
0.6638	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5562	Approved
0.6637	Remote Similarity	NPD7125	Discontinued
0.6635	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8255	Phase 2
0.6627	Remote Similarity	NPD8153	Approved
0.6627	Remote Similarity	NPD8152	Approved
0.6622	Remote Similarity	NPD2975	Approved
0.6622	Remote Similarity	NPD2973	Approved
0.6622	Remote Similarity	NPD2974	Approved
0.6622	Remote Similarity	NPD2490	Approved
0.6622	Remote Similarity	NPD2488	Approved
0.6621	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5137	Approved
0.6618	Remote Similarity	NPD6385	Approved
0.6618	Remote Similarity	NPD6386	Approved
0.6615	Remote Similarity	NPD7708	Approved
0.6614	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2821	Approved
0.6597	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4668	Phase 2
0.659	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7820	Phase 3
0.658	Remote Similarity	NPD6296	Discontinued
0.6579	Remote Similarity	NPD7476	Discontinued
0.6579	Remote Similarity	NPD6321	Discontinued
0.6577	Remote Similarity	NPD5928	Phase 1
0.6574	Remote Similarity	NPD3793	Phase 3
0.6573	Remote Similarity	NPD5186	Approved
0.6573	Remote Similarity	NPD5183	Approved
0.657	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3296	Phase 1
0.6569	Remote Similarity	NPD7907	Approved
0.6565	Remote Similarity	NPD4467	Phase 2
0.6565	Remote Similarity	NPD4465	Phase 2
0.6565	Remote Similarity	NPD7891	Discontinued
0.6561	Remote Similarity	NPD4663	Approved
0.6561	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5496	Approved
0.6555	Remote Similarity	NPD5773	Approved
0.6555	Remote Similarity	NPD5772	Approved
0.6553	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD7417	Discontinued
0.6545	Remote Similarity	NPD8053	Approved
0.6545	Remote Similarity	NPD8054	Approved
0.6545	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4580	Approved
0.6535	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7256	Discontinued
0.6533	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3591	Approved
0.6524	Remote Similarity	NPD3592	Approved
0.6522	Remote Similarity	NPD824	Approved
0.6522	Remote Similarity	NPD6669	Phase 2
0.6515	Remote Similarity	NPD7278	Phase 2
0.6515	Remote Similarity	NPD7279	Phase 2
0.6511	Remote Similarity	NPD5866	Approved
0.6511	Remote Similarity	NPD7225	Discontinued
0.6508	Remote Similarity	NPD8359	Phase 2
0.6504	Remote Similarity	NPD3964	Approved
0.65	Remote Similarity	NPD4577	Approved
0.65	Remote Similarity	NPD4578	Approved
0.6496	Remote Similarity	NPD5860	Discontinued
0.6491	Remote Similarity	NPD3297	Approved
0.6491	Remote Similarity	NPD7565	Approved
0.6489	Remote Similarity	NPD5150	Phase 2
0.6485	Remote Similarity	NPD4665	Approved
0.6485	Remote Similarity	NPD4111	Phase 1
0.6484	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2907	Approved
0.6481	Remote Similarity	NPD2906	Approved
0.6479	Remote Similarity	NPD5677	Discontinued
0.6479	Remote Similarity	NPD2904	Discontinued
0.6478	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3448	Approved
0.6476	Remote Similarity	NPD4604	Approved
0.6476	Remote Similarity	NPD4605	Approved
0.6473	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4049	Phase 2
0.6473	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5871	Discontinued
0.6468	Remote Similarity	NPD7266	Discontinued
0.6468	Remote Similarity	NPD7479	Phase 2
0.6468	Remote Similarity	NPD7472	Approved
0.6465	Remote Similarity	NPD5242	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