NPASS Compound

Structure

NPC68282 OpenBabel07101718202D 53 59 0 0 1 0 0 0 0 0999 V2000 1.4431 -7.9087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3716 -1.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8709 -1.6651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5574 6.0071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8171 6.7889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4445 1.8816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4555 -0.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8894 -7.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2412 -6.3404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6875 -5.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0393 -4.7720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4856 -4.0461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8374 -3.2036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2837 -2.4777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6355 -1.6352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1896 -0.1163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8069 5.2076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5046 0.8386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1134 1.1182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4998 1.9879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7141 1.7867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4774 -0.9827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3555 6.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6220 1.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4931 0.4358 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1469 0.7503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2954 0.0678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7198 5.2016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0731 0.0117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0430 1.7970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7761 0.4637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5871 0.4216 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3584 -0.5806 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0731 1.4890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5848 0.8829 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5871 1.0791 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0818 -0.9093 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4322 1.3427 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4322 0.1580 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8901 0.2032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2432 2.5179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6889 -0.6147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1814 5.9893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0795 2.7017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2763 2.3790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3429 1.2795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0076 0.9342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4321 1.2228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6225 3.6144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1565 0.7503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7577 -1.2681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0818 -0.2519 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 8 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 24 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 12 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 16 22 1 0 0 0 0 16 27 1 0 0 0 0 17 23 1 0 0 0 0 17 28 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 19 47 1 0 0 0 0 20 41 1 0 0 0 0 21 35 1 0 0 0 0 21 48 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 25 39 1 1 0 0 0 26 38 1 1 0 0 0 26 39 1 0 0 0 0 27 42 2 0 0 0 0 27 47 1 0 0 0 0 28 43 2 0 0 0 0 28 49 1 0 0 0 0 29 32 1 0 0 0 0 29 33 1 0 0 0 0 29 39 1 6 0 0 0 30 38 1 0 0 0 0 30 44 2 0 0 0 0 31 40 1 1 0 0 0 31 49 1 0 0 0 0 32 36 1 6 0 0 0 32 50 1 0 0 0 0 33 40 1 1 0 0 0 33 51 1 0 0 0 0 34 36 1 1 0 0 0 34 38 1 0 0 0 0 34 45 1 0 0 0 0 35 7 1 6 0 0 0 35 40 1 0 0 0 0 35 48 1 0 0 0 0 36 20 1 1 0 0 0 36 50 1 0 0 0 0 37 15 1 1 0 0 0 37 51 1 0 0 0 0 37 52 1 0 0 0 0 37 53 1 0 0 0 0 38 46 1 1 0 0 0 39 52 1 1 0 0 0 40 53 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	744.37
Volume:	738.955
LogP:	4.669
LogD:	3.896
LogS:	-3.773
# Rotatable Bonds:	17
TPSA:	183.11
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.096
Synthetic Accessibility Score:	7.102
Fsp3:	0.775
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.039
MDCK Permeability:	3.545685831340961e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.206
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.446

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.446
Plasma Protein Binding (PPB):	90.2624740600586%
Volume Distribution (VD):	1.296
Pgp-substrate:	3.8814609050750732%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.469
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.6
CYP2C9-inhibitor:	0.714
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.853
CYP3A4-substrate:	0.676

ADMET: Excretion

Clearance (CL):	6.781
Half-life (T1/2):	0.152

ADMET: Toxicity

hERG Blockers:	0.52
Human Hepatotoxicity (H-HT):	0.885
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.245
Rat Oral Acute Toxicity:	0.49
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.654
Carcinogencity:	0.924
Eye Corrosion:	0.003
Eye Irritation:	0.01
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: NPC68282

Natural Product ID:	NPC68282
*Common Name:**	Maprouneacin
IUPAC Name:	n.a.
Synonyms:	Maprouneacin
Standard InCHIKey:	XVYNJBXBKDCQQP-FGJZNSICSA-N
Standard InCHI:	InChI=1S/C40H56O13/c1-8-9-10-11-12-13-14-15-37-51-33-29-32-36(20-41,50-32)34(45)38(46)26(18-24(6)30(38)44)39(29,52-37)25(19-47-27(42)16-22(2)3)31(49-28(43)17-23(4)5)40(33,53-37)35(7)21-48-35/h12-15,18,22-23,25-26,29,31-34,41,45-46H,8-11,16-17,19-21H2,1-7H3/b13-12+,15-14+/t25-,26-,29+,31+,32+,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1
SMILES:	CCCCC/C=C/C=C/[C@@]12O[C@H]3[C@@](O1)([C@H]([C@H]([C@@]1(O2)[C@H]3[C@@H]2O[C@@]2([C@H]([C@]2([C@H]1C=C(C2=O)C)O)O)CO)COC(=O)CC(C)C)OC(=O)CC(C)C)[C@@]1(C)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446510
PubChem CID:	44558999
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002943] Dioxepanes [CHEMONTID:0002945] 1,3-dioxepanes

*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
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075783]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631436]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[7515410]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7515410]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7561895]
NPO27192	Maprounea africana	Species	Euphorbiaceae	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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-254.0	mg/dl	PMID[529965]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	37.8	g	PMID[529965]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.1	g	PMID[529965]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-246.0	mg/dl	PMID[529965]

☑ 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 NPC68282 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	314
0.1-0.2	1564
0.2-0.3	4400
0.3-0.4	7621
0.4-0.5	13122
0.5-0.6	9657
0.6-0.7	4875
0.7-0.8	1030
0.8-0.85	65
0.85-0.9	15
0.9-0.95	9
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC475500
0.9839	High Similarity	NPC471136
0.9839	High Similarity	NPC473548
0.9839	High Similarity	NPC100017
0.9839	High Similarity	NPC182266
0.9839	High Similarity	NPC471137
0.9839	High Similarity	NPC223356
0.9839	High Similarity	NPC475154
0.9677	High Similarity	NPC475139
0.9677	High Similarity	NPC180902
0.9677	High Similarity	NPC473485
0.9677	High Similarity	NPC474508
0.9597	High Similarity	NPC475606
0.9597	High Similarity	NPC475314
0.9597	High Similarity	NPC251564
0.9597	High Similarity	NPC477189
0.9516	High Similarity	NPC162495
0.9355	High Similarity	NPC475273
0.9355	High Similarity	NPC168849
0.9274	High Similarity	NPC471939
0.9274	High Similarity	NPC217901
0.92	High Similarity	NPC471940
0.9134	High Similarity	NPC473838
0.9134	High Similarity	NPC475389
0.9113	High Similarity	NPC473802
0.904	High Similarity	NPC473709
0.904	High Similarity	NPC473919
0.8976	High Similarity	NPC236999
0.8976	High Similarity	NPC476091
0.8976	High Similarity	NPC476078
0.8538	High Similarity	NPC270109
0.845	Intermediate Similarity	NPC145238
0.8438	Intermediate Similarity	NPC257017
0.8438	Intermediate Similarity	NPC162009
0.8425	Intermediate Similarity	NPC142882
0.8385	Intermediate Similarity	NPC222307
0.8372	Intermediate Similarity	NPC472399
0.8295	Intermediate Similarity	NPC19464
0.8281	Intermediate Similarity	NPC329008
0.8281	Intermediate Similarity	NPC317635
0.8244	Intermediate Similarity	NPC225049
0.8217	Intermediate Similarity	NPC472401
0.8217	Intermediate Similarity	NPC52839
0.8203	Intermediate Similarity	NPC470186
0.8188	Intermediate Similarity	NPC49297
0.8182	Intermediate Similarity	NPC298841
0.814	Intermediate Similarity	NPC19336
0.814	Intermediate Similarity	NPC185876
0.814	Intermediate Similarity	NPC157252
0.814	Intermediate Similarity	NPC472759
0.814	Intermediate Similarity	NPC471126
0.814	Intermediate Similarity	NPC329080
0.814	Intermediate Similarity	NPC471128
0.814	Intermediate Similarity	NPC145182
0.814	Intermediate Similarity	NPC475885
0.8125	Intermediate Similarity	NPC146280
0.8125	Intermediate Similarity	NPC124676
0.8121	Intermediate Similarity	NPC181924
0.8088	Intermediate Similarity	NPC471234
0.8077	Intermediate Similarity	NPC477046
0.8077	Intermediate Similarity	NPC102822
0.8074	Intermediate Similarity	NPC471855
0.8062	Intermediate Similarity	NPC180640
0.8062	Intermediate Similarity	NPC156745
0.8062	Intermediate Similarity	NPC5989
0.8062	Intermediate Similarity	NPC5991
0.8062	Intermediate Similarity	NPC236918
0.8062	Intermediate Similarity	NPC275696
0.8062	Intermediate Similarity	NPC471108
0.8062	Intermediate Similarity	NPC255081
0.8062	Intermediate Similarity	NPC22628
0.8045	Intermediate Similarity	NPC42399
0.803	Intermediate Similarity	NPC470922
0.8026	Intermediate Similarity	NPC43304
0.8026	Intermediate Similarity	NPC477190
0.8026	Intermediate Similarity	NPC275477
0.8026	Intermediate Similarity	NPC477188
0.8	Intermediate Similarity	NPC476852
0.8	Intermediate Similarity	NPC472004
0.8	Intermediate Similarity	NPC143755
0.7985	Intermediate Similarity	NPC473620
0.7984	Intermediate Similarity	NPC472758
0.7984	Intermediate Similarity	NPC472397
0.7984	Intermediate Similarity	NPC171905
0.7984	Intermediate Similarity	NPC471125
0.7984	Intermediate Similarity	NPC472760
0.7984	Intermediate Similarity	NPC284707
0.7974	Intermediate Similarity	NPC322420
0.7971	Intermediate Similarity	NPC243014
0.797	Intermediate Similarity	NPC473635
0.797	Intermediate Similarity	NPC181999
0.7969	Intermediate Similarity	NPC477509
0.7958	Intermediate Similarity	NPC471172
0.7955	Intermediate Similarity	NPC469352
0.7953	Intermediate Similarity	NPC477126
0.7941	Intermediate Similarity	NPC470185
0.7926	Intermediate Similarity	NPC231529
0.7926	Intermediate Similarity	NPC475371
0.7926	Intermediate Similarity	NPC471407
0.7926	Intermediate Similarity	NPC470851
0.7926	Intermediate Similarity	NPC476851
0.7923	Intermediate Similarity	NPC475775
0.7923	Intermediate Similarity	NPC472667
0.7923	Intermediate Similarity	NPC476529
0.7923	Intermediate Similarity	NPC469488
0.7923	Intermediate Similarity	NPC476107
0.7919	Intermediate Similarity	NPC146310
0.7914	Intermediate Similarity	NPC596
0.791	Intermediate Similarity	NPC470780
0.791	Intermediate Similarity	NPC287423
0.7907	Intermediate Similarity	NPC98249
0.7907	Intermediate Similarity	NPC153651
0.7907	Intermediate Similarity	NPC10721
0.7907	Intermediate Similarity	NPC156252
0.7907	Intermediate Similarity	NPC58662
0.7907	Intermediate Similarity	NPC53396
0.7907	Intermediate Similarity	NPC296822
0.7902	Intermediate Similarity	NPC194854
0.7902	Intermediate Similarity	NPC48813
0.7895	Intermediate Similarity	NPC24651
0.7891	Intermediate Similarity	NPC73314
0.7883	Intermediate Similarity	NPC168879
0.7872	Intermediate Similarity	NPC25887
0.7871	Intermediate Similarity	NPC61891
0.7868	Intermediate Similarity	NPC476862
0.7868	Intermediate Similarity	NPC476863
0.7868	Intermediate Similarity	NPC471170
0.7868	Intermediate Similarity	NPC476855
0.7863	Intermediate Similarity	NPC112038
0.7863	Intermediate Similarity	NPC48692
0.7863	Intermediate Similarity	NPC475003
0.7863	Intermediate Similarity	NPC107338
0.7863	Intermediate Similarity	NPC109607
0.7852	Intermediate Similarity	NPC476859
0.7852	Intermediate Similarity	NPC470850
0.7847	Intermediate Similarity	NPC16729
0.7847	Intermediate Similarity	NPC475462
0.7846	Intermediate Similarity	NPC188667
0.7846	Intermediate Similarity	NPC204552
0.7842	Intermediate Similarity	NPC471089
0.7842	Intermediate Similarity	NPC141215
0.7842	Intermediate Similarity	NPC190065
0.784	Intermediate Similarity	NPC29827
0.7836	Intermediate Similarity	NPC293112
0.7829	Intermediate Similarity	NPC234858
0.7829	Intermediate Similarity	NPC471127
0.7829	Intermediate Similarity	NPC474333
0.7829	Intermediate Similarity	NPC154363
0.7826	Intermediate Similarity	NPC242486
0.7826	Intermediate Similarity	NPC15215
0.7826	Intermediate Similarity	NPC476823
0.782	Intermediate Similarity	NPC67251
0.782	Intermediate Similarity	NPC471392
0.782	Intermediate Similarity	NPC18945
0.782	Intermediate Similarity	NPC265557
0.782	Intermediate Similarity	NPC91693
0.782	Intermediate Similarity	NPC105926
0.782	Intermediate Similarity	NPC11895
0.7817	Intermediate Similarity	NPC5153
0.7817	Intermediate Similarity	NPC470426
0.7817	Intermediate Similarity	NPC48414
0.7812	Intermediate Similarity	NPC469496
0.7812	Intermediate Similarity	NPC469463
0.7812	Intermediate Similarity	NPC469454
0.7812	Intermediate Similarity	NPC474937
0.781	Intermediate Similarity	NPC102316
0.781	Intermediate Similarity	NPC6274
0.781	Intermediate Similarity	NPC254614
0.781	Intermediate Similarity	NPC472769
0.781	Intermediate Similarity	NPC33378
0.781	Intermediate Similarity	NPC476193
0.781	Intermediate Similarity	NPC100390
0.781	Intermediate Similarity	NPC34963
0.781	Intermediate Similarity	NPC231240
0.781	Intermediate Similarity	NPC254146
0.7803	Intermediate Similarity	NPC204731
0.7803	Intermediate Similarity	NPC470779
0.7803	Intermediate Similarity	NPC310511
0.7794	Intermediate Similarity	NPC476854
0.7794	Intermediate Similarity	NPC35109
0.7794	Intermediate Similarity	NPC175186
0.7794	Intermediate Similarity	NPC104382
0.7794	Intermediate Similarity	NPC470880
0.7794	Intermediate Similarity	NPC473593
0.7794	Intermediate Similarity	NPC476966
0.7786	Intermediate Similarity	NPC295885
0.7786	Intermediate Similarity	NPC19028
0.7786	Intermediate Similarity	NPC9674
0.7786	Intermediate Similarity	NPC140045
0.7778	Intermediate Similarity	NPC305496
0.7778	Intermediate Similarity	NPC476008
0.7778	Intermediate Similarity	NPC473253
0.7778	Intermediate Similarity	NPC470882
0.777	Intermediate Similarity	NPC262813
0.7769	Intermediate Similarity	NPC287343
0.7769	Intermediate Similarity	NPC469684
0.7769	Intermediate Similarity	NPC23046
0.7769	Intermediate Similarity	NPC470854
0.7769	Intermediate Similarity	NPC97908
0.7769	Intermediate Similarity	NPC122033

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 NPC68282 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	1700
0.2-0.3	3718
0.3-0.4	2309
0.4-0.5	704
0.5-0.6	312
0.6-0.7	136
0.7-0.8	13
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
0.7619	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD8515	Approved
0.7537	Intermediate Similarity	NPD8517	Approved
0.7537	Intermediate Similarity	NPD8513	Phase 3
0.7537	Intermediate Similarity	NPD8516	Approved
0.7536	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.7464	Intermediate Similarity	NPD7736	Approved
0.7463	Intermediate Similarity	NPD6054	Approved
0.7445	Intermediate Similarity	NPD6616	Approved
0.7422	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7078	Approved
0.736	Intermediate Similarity	NPD5344	Discontinued
0.7353	Intermediate Similarity	NPD6370	Approved
0.7319	Intermediate Similarity	NPD7507	Approved
0.728	Intermediate Similarity	NPD6648	Approved
0.7279	Intermediate Similarity	NPD6015	Approved
0.7279	Intermediate Similarity	NPD6016	Approved
0.7266	Intermediate Similarity	NPD8074	Phase 3
0.7266	Intermediate Similarity	NPD8293	Discontinued
0.7239	Intermediate Similarity	NPD7115	Discovery
0.7231	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5988	Approved
0.7206	Intermediate Similarity	NPD6059	Approved
0.7206	Intermediate Similarity	NPD6319	Approved
0.7176	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6371	Approved
0.7174	Intermediate Similarity	NPD8328	Phase 3
0.7132	Intermediate Similarity	NPD7516	Approved
0.7068	Intermediate Similarity	NPD8297	Approved
0.7068	Intermediate Similarity	NPD6882	Approved
0.7059	Intermediate Similarity	NPD7328	Approved
0.7059	Intermediate Similarity	NPD7327	Approved
0.7055	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6686	Approved
0.6992	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6009	Approved
0.6947	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8296	Approved
0.6906	Remote Similarity	NPD8378	Approved
0.6906	Remote Similarity	NPD8033	Approved
0.6906	Remote Similarity	NPD7503	Approved
0.6906	Remote Similarity	NPD8335	Approved
0.6906	Remote Similarity	NPD8380	Approved
0.6906	Remote Similarity	NPD6921	Approved
0.6906	Remote Similarity	NPD8379	Approved
0.6889	Remote Similarity	NPD4632	Approved
0.6866	Remote Similarity	NPD6649	Approved
0.6866	Remote Similarity	NPD6650	Approved
0.6861	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8294	Approved
0.6835	Remote Similarity	NPD8377	Approved
0.6825	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7830	Approved
0.6809	Remote Similarity	NPD7829	Approved
0.6797	Remote Similarity	NPD4225	Approved
0.6774	Remote Similarity	NPD46	Approved
0.6774	Remote Similarity	NPD6698	Approved
0.6774	Remote Similarity	NPD7838	Discovery
0.6767	Remote Similarity	NPD6881	Approved
0.6767	Remote Similarity	NPD6899	Approved
0.6742	Remote Similarity	NPD6008	Approved
0.6741	Remote Similarity	NPD8130	Phase 1
0.6736	Remote Similarity	NPD6033	Approved
0.672	Remote Similarity	NPD7983	Approved
0.6716	Remote Similarity	NPD6373	Approved
0.6716	Remote Similarity	NPD6372	Approved
0.6705	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5697	Approved
0.6691	Remote Similarity	NPD6053	Discontinued
0.669	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6642	Remote Similarity	NPD7320	Approved
0.6642	Remote Similarity	NPD8133	Approved
0.6618	Remote Similarity	NPD6847	Approved
0.6618	Remote Similarity	NPD6617	Approved
0.6618	Remote Similarity	NPD6869	Approved
0.6617	Remote Similarity	NPD6675	Approved
0.6617	Remote Similarity	NPD6402	Approved
0.6617	Remote Similarity	NPD7128	Approved
0.6617	Remote Similarity	NPD5739	Approved
0.6599	Remote Similarity	NPD7260	Phase 2
0.6593	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6013	Approved
0.6593	Remote Similarity	NPD6014	Approved
0.6593	Remote Similarity	NPD6012	Approved
0.6573	Remote Similarity	NPD7642	Approved
0.656	Remote Similarity	NPD1695	Approved
0.6554	Remote Similarity	NPD8338	Approved
0.6549	Remote Similarity	NPD5983	Phase 2
0.6535	Remote Similarity	NPD5778	Approved
0.6535	Remote Similarity	NPD5779	Approved
0.6529	Remote Similarity	NPD7799	Discontinued
0.6519	Remote Similarity	NPD6011	Approved
0.6484	Remote Similarity	NPD5282	Discontinued
0.6483	Remote Similarity	NPD6336	Discontinued
0.6483	Remote Similarity	NPD8451	Approved
0.6457	Remote Similarity	NPD8407	Phase 2
0.6444	Remote Similarity	NPD5701	Approved
0.6444	Remote Similarity	NPD6412	Phase 2
0.6443	Remote Similarity	NPD6845	Suspended
0.6438	Remote Similarity	NPD8448	Approved
0.6412	Remote Similarity	NPD7638	Approved
0.6391	Remote Similarity	NPD5211	Phase 2
0.6385	Remote Similarity	NPD7839	Suspended
0.6379	Remote Similarity	NPD8368	Discontinued
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD5285	Approved
0.6319	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD8444	Approved
0.6316	Remote Similarity	NPD1700	Approved
0.6309	Remote Similarity	NPD8390	Approved
0.6309	Remote Similarity	NPD8392	Approved
0.6309	Remote Similarity	NPD8391	Approved
0.6309	Remote Similarity	NPD5956	Approved
0.6301	Remote Similarity	NPD8299	Approved
0.6301	Remote Similarity	NPD8341	Approved
0.6301	Remote Similarity	NPD8342	Approved
0.6301	Remote Similarity	NPD8340	Approved
0.6299	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6101	Approved
0.6296	Remote Similarity	NPD5141	Approved
0.6294	Remote Similarity	NPD7100	Approved
0.6294	Remote Similarity	NPD7101	Approved
0.6269	Remote Similarity	NPD5225	Approved
0.6269	Remote Similarity	NPD4633	Approved
0.6269	Remote Similarity	NPD5224	Approved
0.6269	Remote Similarity	NPD5226	Approved
0.6259	Remote Similarity	NPD8273	Phase 1
0.6259	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8415	Approved
0.6224	Remote Similarity	NPD7641	Discontinued
0.6224	Remote Similarity	NPD6335	Approved
0.6222	Remote Similarity	NPD5174	Approved
0.6222	Remote Similarity	NPD5175	Approved
0.6212	Remote Similarity	NPD4755	Approved
0.6209	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6411	Approved
0.6197	Remote Similarity	NPD6274	Approved
0.6194	Remote Similarity	NPD5223	Approved
0.6174	Remote Similarity	NPD8336	Approved
0.6174	Remote Similarity	NPD8337	Approved
0.6164	Remote Similarity	NPD8080	Discontinued
0.6159	Remote Similarity	NPD4729	Approved
0.6159	Remote Similarity	NPD4730	Approved
0.6154	Remote Similarity	NPD6317	Approved
0.6119	Remote Similarity	NPD4700	Approved
0.6111	Remote Similarity	NPD8434	Phase 2
0.6111	Remote Similarity	NPD6314	Approved
0.6111	Remote Similarity	NPD6313	Approved
0.6111	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.609	Remote Similarity	NPD6084	Phase 2
0.609	Remote Similarity	NPD6083	Phase 2
0.6077	Remote Similarity	NPD7637	Suspended
0.6071	Remote Similarity	NPD5250	Approved
0.6071	Remote Similarity	NPD5249	Phase 3
0.6071	Remote Similarity	NPD5248	Approved
0.6071	Remote Similarity	NPD5251	Approved
0.6071	Remote Similarity	NPD5247	Approved
0.6044	Remote Similarity	NPD8360	Approved
0.6044	Remote Similarity	NPD8361	Approved
0.6044	Remote Similarity	NPD8435	Approved
0.6023	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD5222	Approved
0.6015	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD5221	Approved
0.6014	Remote Similarity	NPD6067	Discontinued
0.6014	Remote Similarity	NPD4767	Approved
0.6014	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD3168	Discontinued
0.5986	Remote Similarity	NPD8269	Approved
0.5986	Remote Similarity	NPD6909	Approved
0.5986	Remote Similarity	NPD8268	Approved
0.5986	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD8267	Approved
0.5986	Remote Similarity	NPD6908	Approved
0.5986	Remote Similarity	NPD8266	Approved
0.5984	Remote Similarity	NPD1694	Approved
0.5978	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6868	Approved
0.597	Remote Similarity	NPD7902	Approved
0.597	Remote Similarity	NPD5173	Approved
0.5966	Remote Similarity	NPD3751	Discontinued
0.5954	Remote Similarity	NPD6079	Approved
0.5951	Remote Similarity	NPD7236	Approved
0.5942	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.594	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.594	Remote Similarity	NPD5695	Phase 3
0.5929	Remote Similarity	NPD5128	Approved
0.5926	Remote Similarity	NPD5696	Approved
0.5924	Remote Similarity	NPD6334	Approved
0.5924	Remote Similarity	NPD6333	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