NPASS Compound

Structure

CID147180 OpenBabel06191715522D 42 45 0 0 1 0 0 0 0 0999 V2000 2.5416 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7982 0.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8700 3.0927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9397 2.7904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4493 -0.4046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4684 3.2237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4253 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1862 3.9507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7776 0.1868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8200 0.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0799 2.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3888 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3526 0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8472 0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7776 1.7697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.9783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0368 2.9035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1431 3.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8472 0.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3308 -0.7161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -2.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3391 3.8338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6913 2.1765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7976 4.4743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3308 0.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -2.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 7 32 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 24 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 23 1 0 0 0 0 16 32 1 0 0 0 0 17 1 1 1 0 0 0 17 22 1 0 0 0 0 17 26 1 0 0 0 0 18 34 2 0 0 0 0 18 41 1 0 0 0 0 19 35 2 0 0 0 0 19 42 1 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 32 1 6 0 0 0 22 36 2 0 0 0 0 23 25 1 0 0 0 0 23 41 1 6 0 0 0 24 31 1 1 0 0 0 24 33 1 0 0 0 0 26 27 1 0 0 0 0 26 31 1 6 0 0 0 27 28 1 0 0 0 0 27 42 1 6 0 0 0 28 33 1 0 0 0 0 28 37 2 0 0 0 0 29 38 2 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 31 6 1 6 0 0 0 32 33 1 1 0 0 0 33 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.31
Volume:	605.755
LogP:	2.68
LogD:	1.564
LogS:	-4.198
# Rotatable Bonds:	10
TPSA:	144.27
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.383
Synthetic Accessibility Score:	5.398
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.394
MDCK Permeability:	4.7835881559876725e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.573
Human Intestinal Absorption (HIA):	0.4
20% Bioavailability (F20%):	0.786
30% Bioavailability (F30%):	0.682

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.86
Plasma Protein Binding (PPB):	83.01837921142578%
Volume Distribution (VD):	0.406
Pgp-substrate:	16.303335189819336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.342
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.332

ADMET: Excretion

Clearance (CL):	1.779
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.524
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.902
Maximum Recommended Daily Dose:	0.369
Skin Sensitization:	0.106
Carcinogencity:	0.728
Eye Corrosion:	0.972
Eye Irritation:	0.096
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC147180

Natural Product ID:	NPC147180
*Common Name:**	6Beta,16Beta-Diacetoxy-25-Hydroxy-3,7-Dioxy-29-Nordammara-1,17(20)-Dien-21-Oic Acid
IUPAC Name:	(2Z)-2-[(4S,5S,6S,8S,9S,10R,13R,14S,16S)-6,16-diacetyloxy-4,8,10,14-tetramethyl-3,7-dioxo-5,6,9,11,12,13,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-hydroxy-6-methylheptanoic acid
Synonyms:
Standard InCHIKey:	WLRJWQXWJBEULT-GAZAAFLYSA-N
Standard InCHI:	InChI=1S/C33H46O9/c1-17-22(36)13-15-31(6)24-12-11-21-25(20(29(38)39)10-9-14-30(4,5)40)23(41-18(2)34)16-32(21,7)33(24,8)28(37)27(26(17)31)42-19(3)35/h13,15,17,21,23-24,26-27,40H,9-12,14,16H2,1-8H3,(H,38,39)/b25-20-/t17-,21+,23+,24+,26-,27+,31-,32+,33-/m1/s1
SMILES:	C[C@@H]1C(=O)C=C[C@]2(C)[C@@H]3CC[C@H]4/C(=C(CCCC(C)(C)O)/C(=O)O)/[C@H](C[C@]4(C)[C@@]3(C)C(=O)[C@H]([C@@H]12)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501588
PubChem CID:	24896932
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO32792	aspergillus sydowi	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	10650.0	nM	PMID[520306]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	5330.0	nM	PMID[520306]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	10650.0	nM	PMID[520306]

☑ 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 NPC147180 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	216
0.1-0.2	1324
0.2-0.3	4351
0.3-0.4	8609
0.4-0.5	12755
0.5-0.6	7111
0.6-0.7	6010
0.7-0.8	2191
0.8-0.85	102
0.85-0.9	16
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC264634
0.8899	High Similarity	NPC100267
0.8899	High Similarity	NPC475524
0.8839	High Similarity	NPC311554
0.8839	High Similarity	NPC257457
0.8829	High Similarity	NPC148458
0.8785	High Similarity	NPC475294
0.875	High Similarity	NPC471854
0.8649	High Similarity	NPC472929
0.8596	High Similarity	NPC472933
0.8584	High Similarity	NPC239273
0.8584	High Similarity	NPC472927
0.8559	High Similarity	NPC221144
0.8545	High Similarity	NPC129689
0.8532	High Similarity	NPC295244
0.8468	Intermediate Similarity	NPC115303
0.8455	Intermediate Similarity	NPC77947
0.8455	Intermediate Similarity	NPC286174
0.844	Intermediate Similarity	NPC185
0.844	Intermediate Similarity	NPC44063
0.8426	Intermediate Similarity	NPC135854
0.8426	Intermediate Similarity	NPC118911
0.8426	Intermediate Similarity	NPC2436
0.8426	Intermediate Similarity	NPC470251
0.8426	Intermediate Similarity	NPC216245
0.8421	Intermediate Similarity	NPC472934
0.8421	Intermediate Similarity	NPC243065
0.8411	Intermediate Similarity	NPC53222
0.8381	Intermediate Similarity	NPC253826
0.8362	Intermediate Similarity	NPC109973
0.8333	Intermediate Similarity	NPC33973
0.8333	Intermediate Similarity	NPC70967
0.8333	Intermediate Similarity	NPC270958
0.8319	Intermediate Similarity	NPC472926
0.8319	Intermediate Similarity	NPC25909
0.8318	Intermediate Similarity	NPC124211
0.8318	Intermediate Similarity	NPC224720
0.8318	Intermediate Similarity	NPC476240
0.8318	Intermediate Similarity	NPC476223
0.8304	Intermediate Similarity	NPC472928
0.8288	Intermediate Similarity	NPC2766
0.8241	Intermediate Similarity	NPC136289
0.823	Intermediate Similarity	NPC71348
0.8224	Intermediate Similarity	NPC287833
0.8224	Intermediate Similarity	NPC476274
0.8214	Intermediate Similarity	NPC473627
0.8214	Intermediate Similarity	NPC272898
0.8214	Intermediate Similarity	NPC473036
0.8208	Intermediate Similarity	NPC38530
0.8208	Intermediate Similarity	NPC84335
0.8208	Intermediate Similarity	NPC121339
0.819	Intermediate Similarity	NPC118638
0.8182	Intermediate Similarity	NPC51452
0.8165	Intermediate Similarity	NPC311612
0.8165	Intermediate Similarity	NPC72151
0.8165	Intermediate Similarity	NPC475526
0.8165	Intermediate Similarity	NPC251017
0.8165	Intermediate Similarity	NPC329345
0.8165	Intermediate Similarity	NPC473283
0.8165	Intermediate Similarity	NPC180204
0.8158	Intermediate Similarity	NPC122056
0.8158	Intermediate Similarity	NPC202889
0.8158	Intermediate Similarity	NPC962
0.8158	Intermediate Similarity	NPC250109
0.8151	Intermediate Similarity	NPC120724
0.8148	Intermediate Similarity	NPC115862
0.8148	Intermediate Similarity	NPC81530
0.8142	Intermediate Similarity	NPC43775
0.8131	Intermediate Similarity	NPC57079
0.8131	Intermediate Similarity	NPC108368
0.8131	Intermediate Similarity	NPC275439
0.8131	Intermediate Similarity	NPC112753
0.8125	Intermediate Similarity	NPC214644
0.8125	Intermediate Similarity	NPC220705
0.8113	Intermediate Similarity	NPC3772
0.8108	Intermediate Similarity	NPC473037
0.8103	Intermediate Similarity	NPC470492
0.8091	Intermediate Similarity	NPC189616
0.8087	Intermediate Similarity	NPC147912
0.8087	Intermediate Similarity	NPC67259
0.8073	Intermediate Similarity	NPC119601
0.8073	Intermediate Similarity	NPC155332
0.8073	Intermediate Similarity	NPC281702
0.8073	Intermediate Similarity	NPC32577
0.8073	Intermediate Similarity	NPC308726
0.8073	Intermediate Similarity	NPC114540
0.8073	Intermediate Similarity	NPC87351
0.8073	Intermediate Similarity	NPC320447
0.8073	Intermediate Similarity	NPC293753
0.807	Intermediate Similarity	NPC170487
0.8056	Intermediate Similarity	NPC471413
0.8056	Intermediate Similarity	NPC51370
0.8056	Intermediate Similarity	NPC157787
0.8056	Intermediate Similarity	NPC307954
0.8056	Intermediate Similarity	NPC88198
0.8056	Intermediate Similarity	NPC266955
0.8053	Intermediate Similarity	NPC16270
0.8053	Intermediate Similarity	NPC37116
0.8051	Intermediate Similarity	NPC476962
0.8037	Intermediate Similarity	NPC23680
0.8037	Intermediate Similarity	NPC474343
0.8037	Intermediate Similarity	NPC216904
0.8037	Intermediate Similarity	NPC106557
0.8019	Intermediate Similarity	NPC37646
0.8018	Intermediate Similarity	NPC266570
0.8018	Intermediate Similarity	NPC1679
0.8018	Intermediate Similarity	NPC181265
0.8018	Intermediate Similarity	NPC196528
0.8018	Intermediate Similarity	NPC472645
0.8017	Intermediate Similarity	NPC266728
0.8017	Intermediate Similarity	NPC49492
0.8	Intermediate Similarity	NPC38232
0.8	Intermediate Similarity	NPC159333
0.8	Intermediate Similarity	NPC264048
0.8	Intermediate Similarity	NPC112009
0.8	Intermediate Similarity	NPC79117
0.7984	Intermediate Similarity	NPC471855
0.7983	Intermediate Similarity	NPC310511
0.7982	Intermediate Similarity	NPC472643
0.7982	Intermediate Similarity	NPC168319
0.7982	Intermediate Similarity	NPC194028
0.7982	Intermediate Similarity	NPC163372
0.7982	Intermediate Similarity	NPC231589
0.7982	Intermediate Similarity	NPC214797
0.7982	Intermediate Similarity	NPC302537
0.7982	Intermediate Similarity	NPC115899
0.7982	Intermediate Similarity	NPC118860
0.7982	Intermediate Similarity	NPC471412
0.7982	Intermediate Similarity	NPC474315
0.7981	Intermediate Similarity	NPC476369
0.7981	Intermediate Similarity	NPC476437
0.7966	Intermediate Similarity	NPC268958
0.7966	Intermediate Similarity	NPC475041
0.7966	Intermediate Similarity	NPC264954
0.7965	Intermediate Similarity	NPC258543
0.7965	Intermediate Similarity	NPC474901
0.7965	Intermediate Similarity	NPC241927
0.7965	Intermediate Similarity	NPC475941
0.7965	Intermediate Similarity	NPC304495
0.7963	Intermediate Similarity	NPC176845
0.7963	Intermediate Similarity	NPC478056
0.7949	Intermediate Similarity	NPC470959
0.7949	Intermediate Similarity	NPC167606
0.7949	Intermediate Similarity	NPC286528
0.7949	Intermediate Similarity	NPC20302
0.7949	Intermediate Similarity	NPC140055
0.7949	Intermediate Similarity	NPC476965
0.7946	Intermediate Similarity	NPC472925
0.7946	Intermediate Similarity	NPC220974
0.7944	Intermediate Similarity	NPC472941
0.7944	Intermediate Similarity	NPC243525
0.7944	Intermediate Similarity	NPC40765
0.7944	Intermediate Similarity	NPC301534
0.7944	Intermediate Similarity	NPC249954
0.7944	Intermediate Similarity	NPC456
0.7944	Intermediate Similarity	NPC250757
0.7934	Intermediate Similarity	NPC81736
0.7934	Intermediate Similarity	NPC476729
0.7934	Intermediate Similarity	NPC172154
0.7928	Intermediate Similarity	NPC235889
0.7928	Intermediate Similarity	NPC137657
0.7925	Intermediate Similarity	NPC184870
0.7925	Intermediate Similarity	NPC477439
0.7925	Intermediate Similarity	NPC476415
0.7917	Intermediate Similarity	NPC269642
0.7917	Intermediate Similarity	NPC222688
0.7913	Intermediate Similarity	NPC285956
0.7913	Intermediate Similarity	NPC280782
0.7913	Intermediate Similarity	NPC69291
0.7913	Intermediate Similarity	NPC269530
0.7913	Intermediate Similarity	NPC475970
0.7909	Intermediate Similarity	NPC56498
0.7909	Intermediate Similarity	NPC271266
0.7909	Intermediate Similarity	NPC162973
0.7909	Intermediate Similarity	NPC477915
0.7909	Intermediate Similarity	NPC308351
0.7909	Intermediate Similarity	NPC80781
0.7909	Intermediate Similarity	NPC234892
0.7905	Intermediate Similarity	NPC252433
0.7905	Intermediate Similarity	NPC472975
0.7899	Intermediate Similarity	NPC474370
0.7895	Intermediate Similarity	NPC197428
0.7895	Intermediate Similarity	NPC470496
0.789	Intermediate Similarity	NPC299971
0.789	Intermediate Similarity	NPC471041
0.789	Intermediate Similarity	NPC201406
0.789	Intermediate Similarity	NPC144956
0.789	Intermediate Similarity	NPC251680
0.789	Intermediate Similarity	NPC144660
0.789	Intermediate Similarity	NPC117685
0.7886	Intermediate Similarity	NPC476859
0.7881	Intermediate Similarity	NPC50774
0.7881	Intermediate Similarity	NPC709
0.7881	Intermediate Similarity	NPC329736
0.7881	Intermediate Similarity	NPC21326
0.7881	Intermediate Similarity	NPC146786
0.7881	Intermediate Similarity	NPC470420
0.7876	Intermediate Similarity	NPC318363
0.7876	Intermediate Similarity	NPC475418
0.7876	Intermediate Similarity	NPC189075

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 NPC147180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1553
0.2-0.3	3724
0.3-0.4	2409
0.4-0.5	794
0.5-0.6	211
0.6-0.7	127
0.7-0.8	118
0.8-0.85	27
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD6650	Approved
0.8636	High Similarity	NPD6649	Approved
0.8559	High Similarity	NPD8297	Approved
0.8532	High Similarity	NPD6881	Approved
0.8532	High Similarity	NPD6899	Approved
0.8468	Intermediate Similarity	NPD8130	Phase 1
0.8455	Intermediate Similarity	NPD6373	Approved
0.8455	Intermediate Similarity	NPD6372	Approved
0.844	Intermediate Similarity	NPD5697	Approved
0.8393	Intermediate Similarity	NPD6882	Approved
0.8378	Intermediate Similarity	NPD7290	Approved
0.8378	Intermediate Similarity	NPD6883	Approved
0.8378	Intermediate Similarity	NPD7102	Approved
0.8364	Intermediate Similarity	NPD6011	Approved
0.8349	Intermediate Similarity	NPD7128	Approved
0.8349	Intermediate Similarity	NPD5739	Approved
0.8349	Intermediate Similarity	NPD6675	Approved
0.8349	Intermediate Similarity	NPD6402	Approved
0.8304	Intermediate Similarity	NPD6847	Approved
0.8304	Intermediate Similarity	NPD6869	Approved
0.8304	Intermediate Similarity	NPD6617	Approved
0.8288	Intermediate Similarity	NPD6012	Approved
0.8288	Intermediate Similarity	NPD6014	Approved
0.8288	Intermediate Similarity	NPD6013	Approved
0.8198	Intermediate Similarity	NPD7320	Approved
0.8131	Intermediate Similarity	NPD5696	Approved
0.8108	Intermediate Similarity	NPD5701	Approved
0.8073	Intermediate Similarity	NPD5211	Phase 2
0.7982	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7115	Discovery
0.7928	Intermediate Similarity	NPD5141	Approved
0.789	Intermediate Similarity	NPD4696	Approved
0.789	Intermediate Similarity	NPD5285	Approved
0.789	Intermediate Similarity	NPD7639	Approved
0.789	Intermediate Similarity	NPD5286	Approved
0.789	Intermediate Similarity	NPD7640	Approved
0.7881	Intermediate Similarity	NPD6335	Approved
0.787	Intermediate Similarity	NPD6084	Phase 2
0.787	Intermediate Similarity	NPD6083	Phase 2
0.7818	Intermediate Similarity	NPD5223	Approved
0.7815	Intermediate Similarity	NPD7101	Approved
0.7815	Intermediate Similarity	NPD7100	Approved
0.7798	Intermediate Similarity	NPD7638	Approved
0.7797	Intermediate Similarity	NPD6317	Approved
0.7778	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5221	Approved
0.7778	Intermediate Similarity	NPD5222	Approved
0.775	Intermediate Similarity	NPD6319	Approved
0.7748	Intermediate Similarity	NPD5224	Approved
0.7748	Intermediate Similarity	NPD5225	Approved
0.7748	Intermediate Similarity	NPD4633	Approved
0.7748	Intermediate Similarity	NPD5226	Approved
0.7736	Intermediate Similarity	NPD6079	Approved
0.7736	Intermediate Similarity	NPD5693	Phase 1
0.7731	Intermediate Similarity	NPD6313	Approved
0.7731	Intermediate Similarity	NPD6314	Approved
0.7712	Intermediate Similarity	NPD6868	Approved
0.7712	Intermediate Similarity	NPD6274	Approved
0.7706	Intermediate Similarity	NPD4755	Approved
0.7706	Intermediate Similarity	NPD5173	Approved
0.7692	Intermediate Similarity	NPD4632	Approved
0.7685	Intermediate Similarity	NPD5210	Approved
0.7685	Intermediate Similarity	NPD4629	Approved
0.7685	Intermediate Similarity	NPD5695	Phase 3
0.7679	Intermediate Similarity	NPD5174	Approved
0.7679	Intermediate Similarity	NPD5175	Approved
0.7647	Intermediate Similarity	NPD6009	Approved
0.7619	Intermediate Similarity	NPD5737	Approved
0.7619	Intermediate Similarity	NPD6672	Approved
0.7615	Intermediate Similarity	NPD4697	Phase 3
0.7593	Intermediate Similarity	NPD7748	Approved
0.7568	Intermediate Similarity	NPD4700	Approved
0.7565	Intermediate Similarity	NPD4730	Approved
0.7565	Intermediate Similarity	NPD4729	Approved
0.7561	Intermediate Similarity	NPD7604	Phase 2
0.7547	Intermediate Similarity	NPD5328	Approved
0.7547	Intermediate Similarity	NPD6904	Approved
0.7547	Intermediate Similarity	NPD6080	Approved
0.7547	Intermediate Similarity	NPD6673	Approved
0.7545	Intermediate Similarity	NPD7902	Approved
0.7541	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD5983	Phase 2
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD1694	Approved
0.746	Intermediate Similarity	NPD7736	Approved
0.7459	Intermediate Similarity	NPD6054	Approved
0.744	Intermediate Similarity	NPD6616	Approved
0.744	Intermediate Similarity	NPD6336	Discontinued
0.7436	Intermediate Similarity	NPD5248	Approved
0.7436	Intermediate Similarity	NPD5250	Approved
0.7436	Intermediate Similarity	NPD5251	Approved
0.7436	Intermediate Similarity	NPD5249	Phase 3
0.7436	Intermediate Similarity	NPD5247	Approved
0.7434	Intermediate Similarity	NPD7632	Discontinued
0.7429	Intermediate Similarity	NPD5330	Approved
0.7429	Intermediate Similarity	NPD6409	Approved
0.7429	Intermediate Similarity	NPD6684	Approved
0.7429	Intermediate Similarity	NPD3618	Phase 1
0.7429	Intermediate Similarity	NPD7334	Approved
0.7429	Intermediate Similarity	NPD7146	Approved
0.7429	Intermediate Similarity	NPD7521	Approved
0.7398	Intermediate Similarity	NPD6909	Approved
0.7398	Intermediate Similarity	NPD6908	Approved
0.7391	Intermediate Similarity	NPD4767	Approved
0.7391	Intermediate Similarity	NPD6008	Approved
0.7391	Intermediate Similarity	NPD4768	Approved
0.7381	Intermediate Similarity	NPD7078	Approved
0.7368	Intermediate Similarity	NPD4754	Approved
0.7364	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3573	Approved
0.7339	Intermediate Similarity	NPD6370	Approved
0.7328	Intermediate Similarity	NPD6614	Approved
0.729	Intermediate Similarity	NPD6903	Approved
0.729	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4634	Approved
0.7288	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5169	Approved
0.7288	Intermediate Similarity	NPD5135	Approved
0.7287	Intermediate Similarity	NPD7260	Phase 2
0.7273	Intermediate Similarity	NPD7900	Approved
0.7273	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5128	Approved
0.7264	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6098	Approved
0.7258	Intermediate Similarity	NPD6016	Approved
0.7258	Intermediate Similarity	NPD6015	Approved
0.7248	Intermediate Similarity	NPD7515	Phase 2
0.7248	Intermediate Similarity	NPD6050	Approved
0.7248	Intermediate Similarity	NPD5694	Approved
0.7244	Intermediate Similarity	NPD8293	Discontinued
0.7227	Intermediate Similarity	NPD5127	Approved
0.7227	Intermediate Similarity	NPD5217	Approved
0.7227	Intermediate Similarity	NPD5216	Approved
0.7227	Intermediate Similarity	NPD5215	Approved
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.72	Intermediate Similarity	NPD5988	Approved
0.7182	Intermediate Similarity	NPD4202	Approved
0.7177	Intermediate Similarity	NPD6059	Approved
0.717	Intermediate Similarity	NPD5329	Approved
0.7168	Intermediate Similarity	NPD4225	Approved
0.7165	Intermediate Similarity	NPD7507	Approved
0.7156	Intermediate Similarity	NPD5692	Phase 3
0.7156	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5168	Approved
0.7103	Intermediate Similarity	NPD5690	Phase 2
0.7091	Intermediate Similarity	NPD5281	Approved
0.7091	Intermediate Similarity	NPD8034	Phase 2
0.7091	Intermediate Similarity	NPD8035	Phase 2
0.7091	Intermediate Similarity	NPD5284	Approved
0.7075	Intermediate Similarity	NPD4197	Approved
0.7075	Intermediate Similarity	NPD3665	Phase 1
0.7075	Intermediate Similarity	NPD3666	Approved
0.7075	Intermediate Similarity	NPD3133	Approved
0.7049	Intermediate Similarity	NPD5167	Approved
0.7048	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD8328	Phase 3
0.7	Intermediate Similarity	NPD7319	Approved
0.6983	Remote Similarity	NPD5091	Approved
0.697	Remote Similarity	NPD6845	Suspended
0.6964	Remote Similarity	NPD6001	Approved
0.6917	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4786	Approved
0.6909	Remote Similarity	NPD6051	Approved
0.6903	Remote Similarity	NPD5654	Approved
0.6891	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3667	Approved
0.6887	Remote Similarity	NPD4221	Approved
0.6887	Remote Similarity	NPD4223	Phase 3
0.6885	Remote Similarity	NPD6053	Discontinued
0.6847	Remote Similarity	NPD5207	Approved
0.6833	Remote Similarity	NPD6686	Approved
0.6831	Remote Similarity	NPD7236	Approved
0.6827	Remote Similarity	NPD3617	Approved
0.6818	Remote Similarity	NPD5208	Approved
0.6794	Remote Similarity	NPD6033	Approved
0.6789	Remote Similarity	NPD4694	Approved
0.6789	Remote Similarity	NPD4519	Discontinued
0.6789	Remote Similarity	NPD5279	Phase 3
0.6789	Remote Similarity	NPD4623	Approved
0.6789	Remote Similarity	NPD5280	Approved
0.6783	Remote Similarity	NPD5959	Approved
0.6757	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7503	Approved
0.6712	Remote Similarity	NPD7239	Suspended
0.6698	Remote Similarity	NPD4695	Discontinued
0.6697	Remote Similarity	NPD5363	Approved
0.6697	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7732	Phase 3
0.6696	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8377	Approved
0.6641	Remote Similarity	NPD8294	Approved
0.6637	Remote Similarity	NPD6411	Approved
0.6636	Remote Similarity	NPD4138	Approved
0.6636	Remote Similarity	NPD4689	Approved
0.6636	Remote Similarity	NPD4693	Phase 3
0.6636	Remote Similarity	NPD4688	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