NPASS Compound

Structure

CID57453 OpenBabel06191715392D 41 45 0 0 1 0 0 0 0 0999 V2000 2.8051 -1.5652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5351 1.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8106 -1.6697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3210 0.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5778 1.5910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1131 -0.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6268 1.2820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1784 -1.8788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1620 -2.1924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4266 2.1935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0473 0.7573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2228 -0.8607 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1620 -0.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2283 -0.9653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7553 -1.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3595 -0.1562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 0.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1730 -1.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5742 -3.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4321 2.0890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7607 -1.1743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8443 2.8980 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8498 2.7934 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4430 1.8799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3540 -0.2608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6296 0.0528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0308 1.0709 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5797 -2.8969 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5528 -0.1962 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8333 3.1070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2510 3.8115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2620 3.6025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4485 1.7754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7607 -1.1743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9418 0.5482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0418 0.8618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0253 1.1754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6241 0.1573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 38 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 17 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 31 1 0 0 0 0 11 16 2 0 0 0 0 11 39 1 0 0 0 0 12 3 1 6 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 8 1 6 0 0 0 14 16 1 0 0 0 0 15 21 1 0 0 0 0 16 26 1 0 0 0 0 17 30 1 0 0 0 0 18 21 2 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 10 1 1 0 0 0 20 22 1 0 0 0 0 20 40 1 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 6 0 0 0 23 24 1 0 0 0 0 23 33 1 1 0 0 0 24 28 1 0 0 0 0 24 34 1 6 0 0 0 25 35 1 0 0 0 0 25 36 2 0 0 0 0 26 37 2 0 0 0 0 26 38 1 0 0 0 0 27 39 1 0 0 0 0 27 41 1 1 0 0 0 28 40 1 0 0 0 0 28 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.18
Volume:	542.383
LogP:	0.961
LogD:	0.371
LogS:	-2.552
# Rotatable Bonds:	7
TPSA:	200.89
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.227
Synthetic Accessibility Score:	4.976
Fsp3:	0.393
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.196
MDCK Permeability:	4.773635282617761e-06
Pgp-inhibitor:	0.03
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.743
20% Bioavailability (F20%):	0.316
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179
Plasma Protein Binding (PPB):	79.3531265258789%
Volume Distribution (VD):	0.436
Pgp-substrate:	22.432941436767578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.059

ADMET: Excretion

Clearance (CL):	1.146
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.41
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.905
Rat Oral Acute Toxicity:	0.748
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.174
Carcinogencity:	0.409
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.84

Download Data

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

Natural Product: NPC57453

Natural Product ID:	NPC57453
*Common Name:**	Desoxycordifoline
IUPAC Name:	1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid
Synonyms:	Desoxycordifoline
Standard InCHIKey:	APMZCJQXEGDAIT-HPFOYPDHSA-N
Standard InCHI:	InChI=1S/C28H30N2O11/c1-3-12-14(8-18-21-15(9-19(29-18)25(35)36)13-6-4-5-7-17(13)30-21)16(26(37)38-2)11-39-27(12)41-28-24(34)23(33)22(32)20(10-31)40-28/h3-7,9,11-12,14,20,22-24,27-28,30-34H,1,8,10H2,2H3,(H,35,36)/t12-,14+,20-,22-,23+,24-,27+,28-/m1/s1
SMILES:	OC[C@H]1O[C@H](O[C@@H]2OC=C([C@H]([C@H]2C=C)Cc2nc(cc3c2[nH]c2c3cccc2)C(=O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453150
PubChem CID:	44585556
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568781]
NPO33625	Ochrosia moorei	Species	Apocynaceae	Eukaryota	stems and leaves	Natural Arch National Park, McPherson Range, in South East Queensland	1995-MAR	PMID[18412397]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21341711]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21341711]
NPO27922	Nauclea diderrichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27922	Nauclea diderrichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27922	Nauclea diderrichii	Species	Rubiaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Activity	=	30.0	%	PMID[544141]
NPT1	Others	Radical scavenging activity		IC50	=	49900.0	nM	PMID[544142]

☑ 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 NPC57453 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	345
0.1-0.2	1503
0.2-0.3	5046
0.3-0.4	13124
0.4-0.5	15374
0.5-0.6	4958
0.6-0.7	2021
0.7-0.8	295
0.8-0.85	15
0.85-0.9	13
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9455	High Similarity	NPC473800
0.8972	High Similarity	NPC475271
0.8868	High Similarity	NPC312645
0.8738	High Similarity	NPC82070
0.8726	High Similarity	NPC89508
0.8645	High Similarity	NPC476114
0.8619	High Similarity	NPC244741
0.8565	High Similarity	NPC165599
0.8525	High Similarity	NPC52254
0.8365	Intermediate Similarity	NPC141454
0.8357	Intermediate Similarity	NPC474905
0.8302	Intermediate Similarity	NPC476115
0.8227	Intermediate Similarity	NPC174788
0.8178	Intermediate Similarity	NPC132539
0.8093	Intermediate Similarity	NPC165964
0.8091	Intermediate Similarity	NPC477979
0.8	Intermediate Similarity	NPC118940
0.8	Intermediate Similarity	NPC244856
0.7883	Intermediate Similarity	NPC236424
0.7883	Intermediate Similarity	NPC306644
0.7864	Intermediate Similarity	NPC477548
0.7848	Intermediate Similarity	NPC274842
0.7824	Intermediate Similarity	NPC312870
0.7824	Intermediate Similarity	NPC128265
0.7824	Intermediate Similarity	NPC199851
0.7824	Intermediate Similarity	NPC294909
0.7824	Intermediate Similarity	NPC254240
0.7803	Intermediate Similarity	NPC221100
0.7803	Intermediate Similarity	NPC234078
0.7749	Intermediate Similarity	NPC33949
0.7668	Intermediate Similarity	NPC314834
0.7657	Intermediate Similarity	NPC291609
0.7652	Intermediate Similarity	NPC229893
0.7621	Intermediate Similarity	NPC249428
0.7619	Intermediate Similarity	NPC21638
0.7615	Intermediate Similarity	NPC124300
0.7613	Intermediate Similarity	NPC315545
0.7613	Intermediate Similarity	NPC314297
0.7602	Intermediate Similarity	NPC314648
0.7602	Intermediate Similarity	NPC258048
0.7593	Intermediate Similarity	NPC310618
0.7591	Intermediate Similarity	NPC57398
0.7589	Intermediate Similarity	NPC123839
0.7573	Intermediate Similarity	NPC475844
0.7571	Intermediate Similarity	NPC314394
0.7568	Intermediate Similarity	NPC315638
0.7568	Intermediate Similarity	NPC313345
0.7568	Intermediate Similarity	NPC313796
0.7568	Intermediate Similarity	NPC314855
0.7562	Intermediate Similarity	NPC107836
0.7544	Intermediate Similarity	NPC472285
0.7539	Intermediate Similarity	NPC172355
0.7534	Intermediate Similarity	NPC321428
0.7523	Intermediate Similarity	NPC63199
0.7523	Intermediate Similarity	NPC196251
0.7523	Intermediate Similarity	NPC111602
0.7523	Intermediate Similarity	NPC102338
0.7522	Intermediate Similarity	NPC111732
0.752	Intermediate Similarity	NPC472435
0.7511	Intermediate Similarity	NPC182222
0.75	Intermediate Similarity	NPC266249
0.7489	Intermediate Similarity	NPC472291
0.7489	Intermediate Similarity	NPC238457
0.747	Intermediate Similarity	NPC191489
0.7458	Intermediate Similarity	NPC474701
0.7456	Intermediate Similarity	NPC313640
0.743	Intermediate Similarity	NPC472436
0.743	Intermediate Similarity	NPC160381
0.7419	Intermediate Similarity	NPC472113
0.7407	Intermediate Similarity	NPC472112
0.7397	Intermediate Similarity	NPC245916
0.738	Intermediate Similarity	NPC118228
0.7371	Intermediate Similarity	NPC215837
0.7361	Intermediate Similarity	NPC175474
0.7359	Intermediate Similarity	NPC184408
0.7355	Intermediate Similarity	NPC99891
0.7352	Intermediate Similarity	NPC88923
0.7352	Intermediate Similarity	NPC220151
0.7352	Intermediate Similarity	NPC19692
0.7352	Intermediate Similarity	NPC315634
0.7352	Intermediate Similarity	NPC100734
0.7348	Intermediate Similarity	NPC36405
0.7342	Intermediate Similarity	NPC79129
0.7342	Intermediate Similarity	NPC313985
0.7342	Intermediate Similarity	NPC49196
0.7342	Intermediate Similarity	NPC195461
0.7342	Intermediate Similarity	NPC81654
0.7342	Intermediate Similarity	NPC249150
0.7338	Intermediate Similarity	NPC472842
0.7325	Intermediate Similarity	NPC82370
0.7318	Intermediate Similarity	NPC102592
0.7318	Intermediate Similarity	NPC79356
0.7311	Intermediate Similarity	NPC260434
0.7311	Intermediate Similarity	NPC474688
0.7309	Intermediate Similarity	NPC471944
0.7305	Intermediate Similarity	NPC473639
0.7301	Intermediate Similarity	NPC156044
0.7297	Intermediate Similarity	NPC50997
0.7297	Intermediate Similarity	NPC160127
0.7288	Intermediate Similarity	NPC472762
0.7284	Intermediate Similarity	NPC148889
0.7284	Intermediate Similarity	NPC281049
0.7281	Intermediate Similarity	NPC221873
0.7277	Intermediate Similarity	NPC51388
0.7273	Intermediate Similarity	NPC148183
0.7273	Intermediate Similarity	NPC322064
0.7273	Intermediate Similarity	NPC152768
0.7269	Intermediate Similarity	NPC39679
0.7265	Intermediate Similarity	NPC472434
0.7262	Intermediate Similarity	NPC472846
0.7252	Intermediate Similarity	NPC52557
0.7252	Intermediate Similarity	NPC50503
0.7251	Intermediate Similarity	NPC476514
0.725	Intermediate Similarity	NPC473105
0.7249	Intermediate Similarity	NPC87413
0.7244	Intermediate Similarity	NPC152620
0.7244	Intermediate Similarity	NPC476098
0.7231	Intermediate Similarity	NPC15801
0.723	Intermediate Similarity	NPC219336
0.7227	Intermediate Similarity	NPC247735
0.7227	Intermediate Similarity	NPC472295
0.7227	Intermediate Similarity	NPC472210
0.7227	Intermediate Similarity	NPC269886
0.7227	Intermediate Similarity	NPC81802
0.7227	Intermediate Similarity	NPC194740
0.7227	Intermediate Similarity	NPC274640
0.7222	Intermediate Similarity	NPC323969
0.7222	Intermediate Similarity	NPC284685
0.7222	Intermediate Similarity	NPC472099
0.7212	Intermediate Similarity	NPC25442
0.7212	Intermediate Similarity	NPC12944
0.7208	Intermediate Similarity	NPC474192
0.7208	Intermediate Similarity	NPC475720
0.7202	Intermediate Similarity	NPC470784
0.7196	Intermediate Similarity	NPC469896
0.7188	Intermediate Similarity	NPC79223
0.7188	Intermediate Similarity	NPC214428
0.7186	Intermediate Similarity	NPC39500
0.7186	Intermediate Similarity	NPC317752
0.7183	Intermediate Similarity	NPC217372
0.7183	Intermediate Similarity	NPC183662
0.7183	Intermediate Similarity	NPC15573
0.7182	Intermediate Similarity	NPC55493
0.7169	Intermediate Similarity	NPC469470
0.7169	Intermediate Similarity	NPC469501
0.716	Intermediate Similarity	NPC184680
0.7149	Intermediate Similarity	NPC270918
0.7149	Intermediate Similarity	NPC174760
0.7149	Intermediate Similarity	NPC476516
0.7143	Intermediate Similarity	NPC241024
0.7143	Intermediate Similarity	NPC53534
0.7143	Intermediate Similarity	NPC318299
0.7137	Intermediate Similarity	NPC321592
0.7137	Intermediate Similarity	NPC54803
0.7131	Intermediate Similarity	NPC470785
0.713	Intermediate Similarity	NPC234999
0.713	Intermediate Similarity	NPC139291
0.713	Intermediate Similarity	NPC472108
0.7124	Intermediate Similarity	NPC3207
0.7121	Intermediate Similarity	NPC227824
0.712	Intermediate Similarity	NPC67401
0.7119	Intermediate Similarity	NPC477549
0.7119	Intermediate Similarity	NPC60621
0.7118	Intermediate Similarity	NPC470280
0.7112	Intermediate Similarity	NPC229348
0.7105	Intermediate Similarity	NPC309498
0.7105	Intermediate Similarity	NPC300156
0.7105	Intermediate Similarity	NPC277350
0.7102	Intermediate Similarity	NPC475816
0.7102	Intermediate Similarity	NPC472207
0.7098	Intermediate Similarity	NPC324245
0.7098	Intermediate Similarity	NPC320748
0.7098	Intermediate Similarity	NPC59033
0.7094	Intermediate Similarity	NPC27041
0.7089	Intermediate Similarity	NPC144452
0.7087	Intermediate Similarity	NPC325297
0.7085	Intermediate Similarity	NPC472293
0.7074	Intermediate Similarity	NPC4687
0.7073	Intermediate Similarity	NPC49672
0.7073	Intermediate Similarity	NPC470901
0.7069	Intermediate Similarity	NPC475778
0.7067	Intermediate Similarity	NPC472296
0.7067	Intermediate Similarity	NPC280714
0.7067	Intermediate Similarity	NPC472297
0.7067	Intermediate Similarity	NPC322644
0.7064	Intermediate Similarity	NPC469594
0.7059	Intermediate Similarity	NPC122436
0.7059	Intermediate Similarity	NPC127647
0.7059	Intermediate Similarity	NPC472097
0.7056	Intermediate Similarity	NPC151635
0.7056	Intermediate Similarity	NPC84347
0.7056	Intermediate Similarity	NPC476090
0.7054	Intermediate Similarity	NPC95240
0.7054	Intermediate Similarity	NPC315467
0.7054	Intermediate Similarity	NPC322135
0.7054	Intermediate Similarity	NPC329024
0.7054	Intermediate Similarity	NPC223409
0.7052	Intermediate Similarity	NPC181081
0.7046	Intermediate Similarity	NPC280799
0.7042	Intermediate Similarity	NPC228377

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 NPC57453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	513
0.2-0.3	723
0.3-0.4	1872
0.4-0.5	3144
0.5-0.6	2005
0.6-0.7	609
0.7-0.8	45
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
0.7824	Intermediate Similarity	NPD4501	Approved
0.7824	Intermediate Similarity	NPD4500	Approved
0.7718	Intermediate Similarity	NPD5482	Discontinued
0.7703	Intermediate Similarity	NPD4506	Discontinued
0.7685	Intermediate Similarity	NPD5003	Discontinued
0.7625	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD6770	Approved
0.747	Intermediate Similarity	NPD7708	Approved
0.7445	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5450	Discontinued
0.7382	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD7803	Approved
0.7342	Intermediate Similarity	NPD4600	Approved
0.7342	Intermediate Similarity	NPD4601	Approved
0.7327	Intermediate Similarity	NPD2565	Phase 2
0.7327	Intermediate Similarity	NPD2564	Approved
0.7281	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7956	Approved
0.7222	Intermediate Similarity	NPD7955	Approved
0.7212	Intermediate Similarity	NPD5901	Discontinued
0.7208	Intermediate Similarity	NPD4885	Approved
0.7198	Intermediate Similarity	NPD3394	Approved
0.7198	Intermediate Similarity	NPD3389	Approved
0.7198	Intermediate Similarity	NPD3393	Approved
0.7181	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5632	Approved
0.7109	Intermediate Similarity	NPD6456	Discontinued
0.7105	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5416	Discontinued
0.7094	Intermediate Similarity	NPD8326	Phase 3
0.7094	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8325	Phase 3
0.7082	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8289	Discontinued
0.7066	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8423	Phase 2
0.7043	Intermediate Similarity	NPD8399	Phase 1
0.704	Intermediate Similarity	NPD4602	Approved
0.7039	Intermediate Similarity	NPD3795	Approved
0.7039	Intermediate Similarity	NPD3794	Approved
0.7028	Intermediate Similarity	NPD8468	Phase 2
0.7026	Intermediate Similarity	NPD7470	Discontinued
0.7018	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2920	Discontinued
0.7004	Intermediate Similarity	NPD7727	Phase 2
0.6992	Remote Similarity	NPD7878	Phase 2
0.6987	Remote Similarity	NPD8115	Approved
0.6987	Remote Similarity	NPD8114	Approved
0.6981	Remote Similarity	NPD7181	Phase 3
0.6981	Remote Similarity	NPD2844	Phase 3
0.6976	Remote Similarity	NPD6716	Phase 1
0.697	Remote Similarity	NPD2510	Approved
0.697	Remote Similarity	NPD2509	Approved
0.6957	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7946	Pre-registration
0.6934	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5512	Phase 3
0.6932	Remote Similarity	NPD3328	Phase 2
0.6929	Remote Similarity	NPD8463	Approved
0.6916	Remote Similarity	NPD6248	Phase 2
0.6916	Remote Similarity	NPD6249	Phase 2
0.6914	Remote Similarity	NPD5479	Discontinued
0.6907	Remote Similarity	NPD8160	Phase 2
0.6897	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5805	Approved
0.6875	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7777	Approved
0.6872	Remote Similarity	NPD53	Approved
0.6872	Remote Similarity	NPD7778	Approved
0.6872	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2951	Discontinued
0.687	Remote Similarity	NPD6176	Phase 1
0.6866	Remote Similarity	NPD6641	Approved
0.6866	Remote Similarity	NPD6642	Approved
0.6863	Remote Similarity	NPD8370	Discontinued
0.6861	Remote Similarity	NPD4499	Approved
0.686	Remote Similarity	NPD6531	Approved
0.686	Remote Similarity	NPD6530	Approved
0.6851	Remote Similarity	NPD8097	Phase 3
0.6851	Remote Similarity	NPD8096	Phase 3
0.6849	Remote Similarity	NPD3178	Discontinued
0.6849	Remote Similarity	NPD7395	Discontinued
0.6842	Remote Similarity	NPD7853	Phase 2
0.684	Remote Similarity	NPD56	Approved
0.684	Remote Similarity	NPD8282	Approved
0.684	Remote Similarity	NPD8283	Approved
0.6837	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4373	Phase 2
0.6822	Remote Similarity	NPD3243	Approved
0.6816	Remote Similarity	NPD6962	Phase 2
0.6816	Remote Similarity	NPD7688	Phase 1
0.6811	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8364	Approved
0.6806	Remote Similarity	NPD8363	Approved
0.68	Remote Similarity	NPD7417	Discontinued
0.6797	Remote Similarity	NPD5487	Phase 1
0.6795	Remote Similarity	NPD6529	Discontinued
0.6793	Remote Similarity	NPD4897	Phase 2
0.6792	Remote Similarity	NPD3280	Approved
0.6792	Remote Similarity	NPD1996	Discontinued
0.6786	Remote Similarity	NPD7921	Approved
0.6784	Remote Similarity	NPD6550	Discontinued
0.6783	Remote Similarity	NPD7817	Phase 1
0.6779	Remote Similarity	NPD8465	Approved
0.6779	Remote Similarity	NPD8467	Approved
0.6779	Remote Similarity	NPD8466	Approved
0.6776	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8421	Discontinued
0.6774	Remote Similarity	NPD3006	Discontinued
0.6774	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4558	Phase 2
0.6771	Remote Similarity	NPD4948	Discontinued
0.6769	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7396	Approved
0.6767	Remote Similarity	NPD8098	Approved
0.6766	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4328	Approved
0.6762	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7558	Phase 2
0.6758	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD5913	Phase 3
0.6755	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6376	Discontinued
0.675	Remote Similarity	NPD6974	Phase 3
0.6749	Remote Similarity	NPD3925	Approved
0.6749	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4368	Phase 2
0.6742	Remote Similarity	NPD2092	Phase 2
0.6742	Remote Similarity	NPD2094	Phase 2
0.6742	Remote Similarity	NPD2095	Phase 2
0.6741	Remote Similarity	NPD4334	Discontinued
0.6738	Remote Similarity	NPD7957	Phase 1
0.6738	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3003	Approved
0.6738	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6995	Phase 1
0.6728	Remote Similarity	NPD6182	Approved
0.6728	Remote Similarity	NPD43	Approved
0.6728	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3263	Phase 3
0.6712	Remote Similarity	NPD2096	Phase 2
0.6712	Remote Similarity	NPD2091	Phase 2
0.6712	Remote Similarity	NPD3436	Approved
0.6709	Remote Similarity	NPD5429	Discontinued
0.6709	Remote Similarity	NPD5866	Approved
0.6708	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5022	Discontinued
0.6707	Remote Similarity	NPD4952	Phase 3
0.6696	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3947	Discontinued
0.6694	Remote Similarity	NPD7994	Phase 2
0.6693	Remote Similarity	NPD5488	Discontinued
0.6682	Remote Similarity	NPD5075	Discontinued
0.6681	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6206	Phase 1
0.668	Remote Similarity	NPD7194	Discontinued
0.668	Remote Similarity	NPD3258	Approved
0.6679	Remote Similarity	NPD8425	Approved
0.6679	Remote Similarity	NPD8459	Approved
0.6679	Remote Similarity	NPD8426	Approved
0.6679	Remote Similarity	NPD8460	Approved
0.6667	Remote Similarity	NPD5104	Approved
0.6667	Remote Similarity	NPD5475	Discontinued
0.6667	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD8427	Approved
0.6654	Remote Similarity	NPD8429	Approved
0.6654	Remote Similarity	NPD8428	Approved
0.6653	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7603	Discontinued
0.6653	Remote Similarity	NPD5903	Approved
0.6653	Remote Similarity	NPD4520	Approved
0.6653	Remote Similarity	NPD6242	Discontinued
0.6653	Remote Similarity	NPD5902	Approved
0.6653	Remote Similarity	NPD3746	Discontinued
0.6652	Remote Similarity	NPD6261	Phase 3
0.6643	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6517	Phase 3
0.6639	Remote Similarity	NPD6753	Phase 1
0.6639	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6752	Phase 1
0.6638	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6978	Phase 2
0.6626	Remote Similarity	NPD5507	Approved
0.6626	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5506	Approved
0.6626	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3435	Discontinued
0.6613	Remote Similarity	NPD1867	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