NPASS Compound

Structure

NPC256689 OpenBabel07101718202D 51 52 0 0 1 0 0 0 0 0999 V2000 -5.6670 -20.8062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6616 -20.7017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0683 -19.7881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4805 -18.9791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8873 -18.0656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2995 -17.2566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7062 -16.3430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1184 -15.5340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5252 -14.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9374 -13.8114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3441 -12.8979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5917 -10.6799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7093 -3.1897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7563 -12.0889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9984 -9.7664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2971 -2.3807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1795 -11.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2852 -3.0852 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 -2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7618 -12.1934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6363 -6.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0486 -5.5122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4107 -8.9573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2916 -2.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7728 -12.4025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8730 -3.8942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 0.0000 C 0 0 0 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 -1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2296 -7.2348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3551 -13.1070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0540 -5.6167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4727 -0.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8174 -8.0438 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8794 -1.6762 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3605 -13.2115 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4663 -4.8077 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2351 -7.3393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9429 -13.9160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6473 -6.5303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0605 0.0464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9538 -14.1250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5283 -4.9123 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 14 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 23 2 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 31 2 0 0 0 0 22 33 2 0 0 0 0 23 35 1 0 0 0 0 24 25 1 0 0 0 0 24 34 1 0 0 0 0 25 36 1 0 0 0 0 26 39 1 0 0 0 0 27 40 1 0 0 0 0 28 42 1 0 0 0 0 29 43 1 0 0 0 0 30 32 1 0 0 0 0 30 51 1 0 0 0 0 31 33 1 0 0 0 0 31 38 1 0 0 0 0 32 37 1 1 0 0 0 32 41 1 0 0 0 0 33 44 1 0 0 0 0 34 39 2 3 0 0 0 34 45 1 0 0 0 0 35 42 1 0 0 0 0 35 46 2 0 0 0 0 36 43 1 0 0 0 0 36 47 2 0 0 0 0 37 40 2 3 0 0 0 37 48 1 0 0 0 0 38 41 2 0 0 0 0 38 51 1 0 0 0 0 42 49 1 0 0 0 0 43 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	715.45
Volume:	750.268
LogP:	4.784
LogD:	3.739
LogS:	-3.258
# Rotatable Bonds:	32
TPSA:	188.7
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.017
Synthetic Accessibility Score:	4.021
Fsp3:	0.632
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.521
MDCK Permeability:	3.185003515682183e-05
Pgp-inhibitor:	0.084
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.975
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	95.96111297607422%
Volume Distribution (VD):	1.221
Pgp-substrate:	1.259883999824524%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.258
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.556
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.297
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.874
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	8.576
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.287
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.749
Maximum Recommended Daily Dose:	0.825
Skin Sensitization:	0.639
Carcinogencity:	0.111
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC256689

Natural Product ID:	NPC256689
*Common Name:**	Nocardichelin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XWMNRKXRGYSMGY-YWIDYDFISA-N
Standard InCHI:	InChI=1S/C38H61N5O8/c1-2-3-4-5-6-7-8-9-10-11-14-23-35(46)42(49)28-19-12-17-26-39-34(45)24-25-36(47)43(50)29-20-13-18-27-40-37(48)32-30-51-38(41-32)31-21-15-16-22-33(31)44/h14-16,21-23,32,44,49-50H,2-13,17-20,24-30H2,1H3,(H,39,45)(H,40,48)/b23-14-/t32-/m0/s1
SMILES:	CCCCCCCCCCC/C=CC(=O)N(CCCCCN=C(CCC(=O)N(CCCCCN=C([C@@H]1COC(=N1)c1ccccc1O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228574
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO33043	nocardia strain acta 3026	Species	0cardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17536856]

☑ 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
GI50	3
Others	3

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	TGI	=	1500.0	nM	PMID[522256]
NPT196	Cell Line	AGS	Homo sapiens	GI50	=	44.7	nM	PMID[522256]
NPT65	Cell Line	HepG2	Homo sapiens	TGI	=	335.4	nM	PMID[522256]
NPT65	Cell Line	HepG2	Homo sapiens	GI50	=	69.9	nM	PMID[522256]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	1130.0	nM	PMID[522256]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	3490.0	nM	PMID[522256]

☑ 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 NPC256689 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	182
0.1-0.2	1179
0.2-0.3	6546
0.3-0.4	10678
0.4-0.5	9788
0.5-0.6	13236
0.6-0.7	1017
0.7-0.8	66
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC123011
0.7622	Intermediate Similarity	NPC5932
0.7469	Intermediate Similarity	NPC39431
0.7468	Intermediate Similarity	NPC81026
0.7436	Intermediate Similarity	NPC197921
0.7425	Intermediate Similarity	NPC472923
0.7407	Intermediate Similarity	NPC262166
0.7405	Intermediate Similarity	NPC266741
0.7389	Intermediate Similarity	NPC91953
0.7389	Intermediate Similarity	NPC469360
0.7301	Intermediate Similarity	NPC56685
0.7284	Intermediate Similarity	NPC473491
0.7278	Intermediate Similarity	NPC254700
0.7261	Intermediate Similarity	NPC471201
0.7251	Intermediate Similarity	NPC475204
0.7251	Intermediate Similarity	NPC40234
0.7251	Intermediate Similarity	NPC475123
0.7244	Intermediate Similarity	NPC6570
0.7235	Intermediate Similarity	NPC107938
0.7235	Intermediate Similarity	NPC294516
0.7215	Intermediate Similarity	NPC476989
0.7212	Intermediate Similarity	NPC244509
0.7205	Intermediate Similarity	NPC16188
0.7168	Intermediate Similarity	NPC137627
0.7161	Intermediate Similarity	NPC328070
0.7152	Intermediate Similarity	NPC322526
0.7151	Intermediate Similarity	NPC46009
0.7151	Intermediate Similarity	NPC196091
0.7134	Intermediate Similarity	NPC233702
0.7126	Intermediate Similarity	NPC279871
0.7126	Intermediate Similarity	NPC26108
0.7126	Intermediate Similarity	NPC471165
0.7124	Intermediate Similarity	NPC17374
0.7115	Intermediate Similarity	NPC169766
0.711	Intermediate Similarity	NPC230611
0.7102	Intermediate Similarity	NPC475421
0.7091	Intermediate Similarity	NPC5194
0.7091	Intermediate Similarity	NPC202198
0.7091	Intermediate Similarity	NPC261934
0.7089	Intermediate Similarity	NPC473055
0.7089	Intermediate Similarity	NPC473052
0.7083	Intermediate Similarity	NPC244336
0.7069	Intermediate Similarity	NPC273755
0.7069	Intermediate Similarity	NPC306804
0.7067	Intermediate Similarity	NPC474862
0.7059	Intermediate Similarity	NPC218323
0.7055	Intermediate Similarity	NPC317254
0.7052	Intermediate Similarity	NPC473693
0.7052	Intermediate Similarity	NPC471568
0.7035	Intermediate Similarity	NPC473502
0.7029	Intermediate Similarity	NPC158277
0.7029	Intermediate Similarity	NPC155506
0.7029	Intermediate Similarity	NPC473354
0.7029	Intermediate Similarity	NPC476227
0.7029	Intermediate Similarity	NPC473402
0.7029	Intermediate Similarity	NPC159767
0.7025	Intermediate Similarity	NPC43755
0.7013	Intermediate Similarity	NPC296712
0.7006	Intermediate Similarity	NPC105541
0.7006	Intermediate Similarity	NPC269750
0.7006	Intermediate Similarity	NPC194671
0.7006	Intermediate Similarity	NPC132308
0.7	Intermediate Similarity	NPC315542
0.6995	Remote Similarity	NPC477526
0.6994	Remote Similarity	NPC135121
0.6994	Remote Similarity	NPC186617
0.6989	Remote Similarity	NPC50016
0.6983	Remote Similarity	NPC167763
0.6983	Remote Similarity	NPC470112
0.6983	Remote Similarity	NPC470903
0.6982	Remote Similarity	NPC287757
0.6982	Remote Similarity	NPC319320
0.6975	Remote Similarity	NPC201244
0.6975	Remote Similarity	NPC477217
0.6971	Remote Similarity	NPC248670
0.697	Remote Similarity	NPC324081
0.6962	Remote Similarity	NPC473360
0.6957	Remote Similarity	NPC83289
0.6957	Remote Similarity	NPC212850
0.6957	Remote Similarity	NPC189724
0.6954	Remote Similarity	NPC268348
0.6943	Remote Similarity	NPC274732
0.6941	Remote Similarity	NPC476194
0.6936	Remote Similarity	NPC302597
0.6928	Remote Similarity	NPC171372
0.6923	Remote Similarity	NPC323336
0.6923	Remote Similarity	NPC329731
0.6923	Remote Similarity	NPC326349
0.6923	Remote Similarity	NPC4910
0.6923	Remote Similarity	NPC56635
0.6919	Remote Similarity	NPC63931
0.6914	Remote Similarity	NPC328494
0.691	Remote Similarity	NPC45037
0.6909	Remote Similarity	NPC245974
0.6909	Remote Similarity	NPC132771
0.6906	Remote Similarity	NPC299806
0.6905	Remote Similarity	NPC476268
0.6905	Remote Similarity	NPC473580
0.689	Remote Similarity	NPC247298
0.6882	Remote Similarity	NPC59827
0.6882	Remote Similarity	NPC184933
0.6879	Remote Similarity	NPC246079
0.6879	Remote Similarity	NPC61004
0.6875	Remote Similarity	NPC242159
0.6875	Remote Similarity	NPC313694
0.6867	Remote Similarity	NPC283760
0.6863	Remote Similarity	NPC476260
0.6863	Remote Similarity	NPC476241
0.686	Remote Similarity	NPC289776
0.686	Remote Similarity	NPC191863
0.686	Remote Similarity	NPC133470
0.6852	Remote Similarity	NPC477837
0.6852	Remote Similarity	NPC477838
0.6851	Remote Similarity	NPC294951
0.6842	Remote Similarity	NPC471203
0.6835	Remote Similarity	NPC471953
0.6835	Remote Similarity	NPC470392
0.6833	Remote Similarity	NPC473404
0.6833	Remote Similarity	NPC476321
0.6828	Remote Similarity	NPC328763
0.6824	Remote Similarity	NPC207675
0.6824	Remote Similarity	NPC212699
0.6818	Remote Similarity	NPC476125
0.6818	Remote Similarity	NPC476179
0.6815	Remote Similarity	NPC120251
0.6813	Remote Similarity	NPC196708
0.6813	Remote Similarity	NPC64205
0.6811	Remote Similarity	NPC473407
0.6811	Remote Similarity	NPC473378
0.6802	Remote Similarity	NPC241794
0.68	Remote Similarity	NPC129486
0.6797	Remote Similarity	NPC477151
0.6797	Remote Similarity	NPC132518
0.6796	Remote Similarity	NPC471526
0.6795	Remote Similarity	NPC477839
0.6791	Remote Similarity	NPC471563
0.6781	Remote Similarity	NPC227553
0.6778	Remote Similarity	NPC32064
0.6776	Remote Similarity	NPC473051
0.6776	Remote Similarity	NPC473050
0.6772	Remote Similarity	NPC477527
0.6772	Remote Similarity	NPC326966
0.6768	Remote Similarity	NPC106183
0.6759	Remote Similarity	NPC258056
0.6758	Remote Similarity	NPC471050
0.6758	Remote Similarity	NPC471049
0.6758	Remote Similarity	NPC471048
0.6757	Remote Similarity	NPC283207
0.6747	Remote Similarity	NPC9373
0.6744	Remote Similarity	NPC475544
0.6744	Remote Similarity	NPC469243
0.6743	Remote Similarity	NPC328649
0.6742	Remote Similarity	NPC164608
0.6742	Remote Similarity	NPC165285
0.6731	Remote Similarity	NPC476353
0.673	Remote Similarity	NPC244866
0.6727	Remote Similarity	NPC473804
0.6723	Remote Similarity	NPC83241
0.6723	Remote Similarity	NPC89831
0.6721	Remote Similarity	NPC138083
0.672	Remote Similarity	NPC281629
0.6711	Remote Similarity	NPC17388
0.6711	Remote Similarity	NPC476183
0.6711	Remote Similarity	NPC289330
0.6711	Remote Similarity	NPC471308
0.6711	Remote Similarity	NPC53596
0.6711	Remote Similarity	NPC160120
0.6708	Remote Similarity	NPC127741
0.6707	Remote Similarity	NPC315283
0.6707	Remote Similarity	NPC476444
0.6707	Remote Similarity	NPC314388
0.6705	Remote Similarity	NPC66490
0.6705	Remote Similarity	NPC156348
0.6688	Remote Similarity	NPC213969
0.6688	Remote Similarity	NPC165726
0.6687	Remote Similarity	NPC231572
0.6687	Remote Similarity	NPC150712
0.6687	Remote Similarity	NPC119569
0.6685	Remote Similarity	NPC475532
0.6685	Remote Similarity	NPC276120
0.6684	Remote Similarity	NPC323662
0.6667	Remote Similarity	NPC476281
0.6667	Remote Similarity	NPC257390
0.6667	Remote Similarity	NPC471447
0.6667	Remote Similarity	NPC316008
0.6667	Remote Similarity	NPC61332
0.6667	Remote Similarity	NPC473305
0.6667	Remote Similarity	NPC86966
0.6667	Remote Similarity	NPC163961
0.6667	Remote Similarity	NPC7817
0.6667	Remote Similarity	NPC29531
0.6667	Remote Similarity	NPC476184
0.6667	Remote Similarity	NPC240130
0.6667	Remote Similarity	NPC239357
0.6667	Remote Similarity	NPC475168
0.6667	Remote Similarity	NPC77992
0.6667	Remote Similarity	NPC307682
0.6667	Remote Similarity	NPC313867
0.6648	Remote Similarity	NPC209463
0.6648	Remote Similarity	NPC136797

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 NPC256689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	501
0.2-0.3	897
0.3-0.4	1856
0.4-0.5	3049
0.5-0.6	2389
0.6-0.7	319
0.7-0.8	5
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
0.7407	Intermediate Similarity	NPD7131	Phase 3
0.719	Intermediate Similarity	NPD4207	Discontinued
0.7161	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4208	Discontinued
0.7107	Intermediate Similarity	NPD1725	Approved
0.7101	Intermediate Similarity	NPD7318	Phase 3
0.7093	Intermediate Similarity	NPD7485	Phase 3
0.7093	Intermediate Similarity	NPD7484	Phase 3
0.7052	Intermediate Similarity	NPD7608	Discontinued
0.7027	Intermediate Similarity	NPD1759	Phase 1
0.7024	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4149	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3692	Discontinued
0.6982	Remote Similarity	NPD7317	Phase 3
0.6974	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1758	Phase 1
0.6957	Remote Similarity	NPD7978	Discontinued
0.6923	Remote Similarity	NPD3136	Phase 2
0.6914	Remote Similarity	NPD6681	Discovery
0.6892	Remote Similarity	NPD3123	Discovery
0.6879	Remote Similarity	NPD1048	Approved
0.6875	Remote Similarity	NPD6894	Phase 1
0.6848	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD520	Approved
0.6826	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4357	Discontinued
0.677	Remote Similarity	NPD3555	Approved
0.677	Remote Similarity	NPD3554	Approved
0.677	Remote Similarity	NPD3553	Approved
0.677	Remote Similarity	NPD3552	Approved
0.6768	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.673	Remote Similarity	NPD839	Approved
0.673	Remote Similarity	NPD840	Approved
0.673	Remote Similarity	NPD7477	Discontinued
0.6727	Remote Similarity	NPD5481	Discontinued
0.6726	Remote Similarity	NPD6390	Discontinued
0.6726	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD8031	Discontinued
0.6721	Remote Similarity	NPD6045	Phase 3
0.671	Remote Similarity	NPD2079	Discontinued
0.6687	Remote Similarity	NPD7450	Phase 2
0.6686	Remote Similarity	NPD8303	Discontinued
0.6686	Remote Similarity	NPD6862	Phase 2
0.6667	Remote Similarity	NPD2517	Approved
0.6667	Remote Similarity	NPD3421	Phase 3
0.6667	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2592	Discontinued
0.6649	Remote Similarity	NPD4466	Phase 1
0.6647	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5557	Phase 1
0.6628	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7613	Discontinued
0.6627	Remote Similarity	NPD7303	Discontinued
0.6625	Remote Similarity	NPD5745	Approved
0.661	Remote Similarity	NPD2516	Approved
0.6609	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1786	Approved
0.6607	Remote Similarity	NPD1787	Approved
0.6607	Remote Similarity	NPD6087	Phase 1
0.6607	Remote Similarity	NPD1785	Approved
0.6606	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD8173	Phase 2
0.6605	Remote Similarity	NPD8172	Phase 2
0.6603	Remote Similarity	NPD3125	Approved
0.659	Remote Similarity	NPD8019	Approved
0.6588	Remote Similarity	NPD1670	Discontinued
0.6578	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD2505	Approved
0.6568	Remote Similarity	NPD2504	Approved
0.6562	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7972	Discontinued
0.6548	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6072	Discontinued
0.6524	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7451	Discontinued
0.6519	Remote Similarity	NPD3909	Discontinued
0.6509	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5746	Approved
0.6494	Remote Similarity	NPD7011	Discontinued
0.6494	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7523	Phase 3
0.6488	Remote Similarity	NPD2219	Phase 1
0.6481	Remote Similarity	NPD8416	Discontinued
0.6481	Remote Similarity	NPD6346	Approved
0.6478	Remote Similarity	NPD1712	Approved
0.6477	Remote Similarity	NPD7565	Approved
0.6474	Remote Similarity	NPD6502	Phase 2
0.6474	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.645	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD2098	Approved
0.6436	Remote Similarity	NPD4435	Approved
0.6436	Remote Similarity	NPD3490	Discontinued
0.6429	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2415	Discontinued
0.642	Remote Similarity	NPD6405	Approved
0.642	Remote Similarity	NPD5967	Approved
0.642	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6407	Approved
0.642	Remote Similarity	NPD1423	Approved
0.6417	Remote Similarity	NPD3153	Approved
0.6417	Remote Similarity	NPD3154	Approved
0.6411	Remote Similarity	NPD8059	Phase 3
0.6411	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7153	Discontinued
0.6402	Remote Similarity	NPD3052	Approved
0.6402	Remote Similarity	NPD3054	Approved
0.64	Remote Similarity	NPD821	Approved
0.6395	Remote Similarity	NPD3033	Phase 2
0.6392	Remote Similarity	NPD7810	Phase 3
0.6392	Remote Similarity	NPD6325	Discontinued
0.6392	Remote Similarity	NPD7811	Phase 3
0.6389	Remote Similarity	NPD4652	Approved
0.6386	Remote Similarity	NPD6032	Approved
0.6384	Remote Similarity	NPD3674	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4434	Approved
0.6375	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7447	Phase 1
0.6374	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2459	Approved
0.6369	Remote Similarity	NPD6746	Phase 2
0.6369	Remote Similarity	NPD2584	Suspended
0.6369	Remote Similarity	NPD2460	Phase 3
0.6369	Remote Similarity	NPD2458	Approved
0.6368	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5773	Approved
0.6364	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD696	Discontinued
0.6364	Remote Similarity	NPD5772	Approved
0.6364	Remote Similarity	NPD2200	Suspended
0.6358	Remote Similarity	NPD4911	Discontinued
0.6358	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1330	Phase 2
0.6354	Remote Similarity	NPD2388	Discontinued
0.6353	Remote Similarity	NPD6666	Approved
0.6353	Remote Similarity	NPD6667	Approved
0.6352	Remote Similarity	NPD1131	Approved
0.6352	Remote Similarity	NPD1135	Approved
0.6352	Remote Similarity	NPD1133	Approved
0.6352	Remote Similarity	NPD1129	Approved
0.6352	Remote Similarity	NPD1134	Approved
0.6349	Remote Similarity	NPD2792	Approved
0.6348	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8070	Approved
0.6347	Remote Similarity	NPD3656	Approved
0.6344	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD654	Phase 3
0.634	Remote Similarity	NPD5292	Approved
0.634	Remote Similarity	NPD5291	Approved
0.6339	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2184	Approved
0.6337	Remote Similarity	NPD2183	Approved
0.6335	Remote Similarity	NPD596	Approved
0.6335	Remote Similarity	NPD600	Approved
0.6333	Remote Similarity	NPD2890	Approved
0.6333	Remote Similarity	NPD2888	Approved
0.6333	Remote Similarity	NPD2017	Approved
0.6333	Remote Similarity	NPD2889	Approved
0.6331	Remote Similarity	NPD3400	Discontinued
0.6329	Remote Similarity	NPD1421	Approved
0.6329	Remote Similarity	NPD1420	Approved
0.6328	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7738	Approved
0.6328	Remote Similarity	NPD2097	Approved
0.6328	Remote Similarity	NPD7737	Approved
0.6325	Remote Similarity	NPD1753	Discontinued
0.6324	Remote Similarity	NPD3823	Discontinued
0.6322	Remote Similarity	NPD3111	Phase 1
0.6322	Remote Similarity	NPD824	Approved
0.6319	Remote Similarity	NPD2674	Phase 3
0.6319	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD595	Approved
0.6316	Remote Similarity	NPD7213	Phase 3
0.6316	Remote Similarity	NPD593	Approved
0.6316	Remote Similarity	NPD7212	Phase 2
0.6307	Remote Similarity	NPD6844	Discontinued
0.6307	Remote Similarity	NPD7495	Discontinued
0.6306	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD2157	Approved
0.6296	Remote Similarity	NPD4738	Phase 2
0.6294	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6863	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