NPASS Compound

Structure

CID147232 OpenBabel06191715522D 35 39 0 0 1 0 0 0 0 0999 V2000 5.0662 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5081 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0206 0.6181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8650 0.8444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5331 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5331 2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 1 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 3.3775 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5331 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6887 3.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8900 0.8444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 30 1 0 0 0 0 16 19 2 0 0 0 0 16 26 1 0 0 0 0 17 29 1 6 0 0 0 18 22 1 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 1 0 0 0 21 26 1 1 0 0 0 21 28 1 0 0 0 0 22 29 1 6 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 32 2 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 29 35 1 0 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.32
Volume:	518.059
LogP:	4.712
LogD:	4.252
LogS:	-4.454
# Rotatable Bonds:	1
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	4.994
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.477
MDCK Permeability:	1.8836102753994055e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	89.57245635986328%
Volume Distribution (VD):	0.573
Pgp-substrate:	6.706668376922607%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.156
CYP2C9-substrate:	0.257
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.316
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	1.582
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.235
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.367
Carcinogencity:	0.131
Eye Corrosion:	0.403
Eye Irritation:	0.445
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC147232

Natural Product ID:	NPC147232
*Common Name:**	Fupenzic Acid
IUPAC Name:	(1R,2R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-1,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,13,14b-decahydro-2H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	FMTPULGTIHBJRT-BBRBLNSOSA-N
Standard InCHI:	InChI=1S/C30H44O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,16-17,20-22,31,35H,9-15H2,1-7H3,(H,33,34)/t17-,20+,21-,22-,26+,27-,28-,29-,30+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C=C(C(=O)C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2[C@]1(C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3114758
PubChem CID:	12045007
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21381697]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.		Database[Phenol-Explorer]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	Inhibition	<	10.0	%	PMID[548267]

☑ 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 NPC147232 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	219
0.1-0.2	1422
0.2-0.3	5258
0.3-0.4	12384
0.4-0.5	10611
0.5-0.6	6709
0.6-0.7	4712
0.7-0.8	1219
0.8-0.85	143
0.85-0.9	18
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC112454
0.8913	High Similarity	NPC263780
0.883	High Similarity	NPC62516
0.883	High Similarity	NPC157113
0.8817	High Similarity	NPC23170
0.8804	High Similarity	NPC174167
0.8804	High Similarity	NPC470036
0.8791	High Similarity	NPC65615
0.8791	High Similarity	NPC68148
0.8764	High Similarity	NPC474537
0.875	High Similarity	NPC105803
0.875	High Similarity	NPC53733
0.8673	High Similarity	NPC179208
0.8652	High Similarity	NPC96095
0.8617	High Similarity	NPC148964
0.8617	High Similarity	NPC160413
0.8602	High Similarity	NPC38754
0.8587	High Similarity	NPC477973
0.8556	High Similarity	NPC474680
0.8556	High Similarity	NPC469993
0.8526	High Similarity	NPC777
0.8523	High Similarity	NPC278459
0.8523	High Similarity	NPC471898
0.8523	High Similarity	NPC55869
0.8511	High Similarity	NPC118519
0.8511	High Similarity	NPC202728
0.8511	High Similarity	NPC118490
0.8511	High Similarity	NPC158059
0.8511	High Similarity	NPC211230
0.8495	Intermediate Similarity	NPC193750
0.8478	Intermediate Similarity	NPC48107
0.8469	Intermediate Similarity	NPC118964
0.8427	Intermediate Similarity	NPC251779
0.8427	Intermediate Similarity	NPC69101
0.8421	Intermediate Similarity	NPC114159
0.8421	Intermediate Similarity	NPC191412
0.8421	Intermediate Similarity	NPC6818
0.8409	Intermediate Similarity	NPC37038
0.8409	Intermediate Similarity	NPC108955
0.8404	Intermediate Similarity	NPC235704
0.8404	Intermediate Similarity	NPC105189
0.8404	Intermediate Similarity	NPC233455
0.8404	Intermediate Similarity	NPC145067
0.8404	Intermediate Similarity	NPC187722
0.8404	Intermediate Similarity	NPC65120
0.8404	Intermediate Similarity	NPC4036
0.8404	Intermediate Similarity	NPC474525
0.8404	Intermediate Similarity	NPC158030
0.8351	Intermediate Similarity	NPC473456
0.8333	Intermediate Similarity	NPC139570
0.8316	Intermediate Similarity	NPC214756
0.8316	Intermediate Similarity	NPC295643
0.8316	Intermediate Similarity	NPC272075
0.8316	Intermediate Similarity	NPC229281
0.8315	Intermediate Similarity	NPC274050
0.8315	Intermediate Similarity	NPC162632
0.8315	Intermediate Similarity	NPC267691
0.8315	Intermediate Similarity	NPC263272
0.8315	Intermediate Similarity	NPC473217
0.8298	Intermediate Similarity	NPC210037
0.8298	Intermediate Similarity	NPC290614
0.8298	Intermediate Similarity	NPC273621
0.8298	Intermediate Similarity	NPC291028
0.8298	Intermediate Similarity	NPC477872
0.8298	Intermediate Similarity	NPC7260
0.8298	Intermediate Similarity	NPC227467
0.8298	Intermediate Similarity	NPC18872
0.8298	Intermediate Similarity	NPC120968
0.8298	Intermediate Similarity	NPC46441
0.8295	Intermediate Similarity	NPC231431
0.8295	Intermediate Similarity	NPC199595
0.8295	Intermediate Similarity	NPC192329
0.8265	Intermediate Similarity	NPC194196
0.8265	Intermediate Similarity	NPC478056
0.8247	Intermediate Similarity	NPC207922
0.8247	Intermediate Similarity	NPC132824
0.8247	Intermediate Similarity	NPC158371
0.8247	Intermediate Similarity	NPC116457
0.8247	Intermediate Similarity	NPC259733
0.8247	Intermediate Similarity	NPC327179
0.8229	Intermediate Similarity	NPC74751
0.8229	Intermediate Similarity	NPC474328
0.8218	Intermediate Similarity	NPC213366
0.8218	Intermediate Similarity	NPC284865
0.8202	Intermediate Similarity	NPC18955
0.8191	Intermediate Similarity	NPC64872
0.8191	Intermediate Similarity	NPC198664
0.8191	Intermediate Similarity	NPC143232
0.8191	Intermediate Similarity	NPC274330
0.8191	Intermediate Similarity	NPC25906
0.8191	Intermediate Similarity	NPC290972
0.8182	Intermediate Similarity	NPC110094
0.8182	Intermediate Similarity	NPC280654
0.8182	Intermediate Similarity	NPC74410
0.8182	Intermediate Similarity	NPC260385
0.8172	Intermediate Similarity	NPC71507
0.8163	Intermediate Similarity	NPC170131
0.8163	Intermediate Similarity	NPC259788
0.8163	Intermediate Similarity	NPC255589
0.8163	Intermediate Similarity	NPC247139
0.8163	Intermediate Similarity	NPC9613
0.8163	Intermediate Similarity	NPC187933
0.8152	Intermediate Similarity	NPC263997
0.8152	Intermediate Similarity	NPC132228
0.8152	Intermediate Similarity	NPC6185
0.8152	Intermediate Similarity	NPC8518
0.8152	Intermediate Similarity	NPC241512
0.8144	Intermediate Similarity	NPC96916
0.8144	Intermediate Similarity	NPC32118
0.8144	Intermediate Similarity	NPC148523
0.8132	Intermediate Similarity	NPC70834
0.8125	Intermediate Similarity	NPC133579
0.8125	Intermediate Similarity	NPC474806
0.8111	Intermediate Similarity	NPC475863
0.8111	Intermediate Similarity	NPC142244
0.8105	Intermediate Similarity	NPC470589
0.8105	Intermediate Similarity	NPC130278
0.8105	Intermediate Similarity	NPC252737
0.8105	Intermediate Similarity	NPC126369
0.8105	Intermediate Similarity	NPC111110
0.8105	Intermediate Similarity	NPC474728
0.809	Intermediate Similarity	NPC16394
0.8085	Intermediate Similarity	NPC474474
0.8085	Intermediate Similarity	NPC181225
0.8085	Intermediate Similarity	NPC230387
0.8085	Intermediate Similarity	NPC1753
0.8085	Intermediate Similarity	NPC17733
0.8085	Intermediate Similarity	NPC470629
0.8085	Intermediate Similarity	NPC290690
0.8085	Intermediate Similarity	NPC52169
0.8085	Intermediate Similarity	NPC182797
0.8085	Intermediate Similarity	NPC474511
0.8085	Intermediate Similarity	NPC474512
0.8085	Intermediate Similarity	NPC473242
0.8081	Intermediate Similarity	NPC471966
0.8081	Intermediate Similarity	NPC174663
0.8068	Intermediate Similarity	NPC107039
0.8068	Intermediate Similarity	NPC165711
0.8068	Intermediate Similarity	NPC471899
0.8068	Intermediate Similarity	NPC471897
0.8065	Intermediate Similarity	NPC56588
0.8061	Intermediate Similarity	NPC235053
0.8061	Intermediate Similarity	NPC73004
0.8061	Intermediate Similarity	NPC269492
0.8061	Intermediate Similarity	NPC472806
0.8061	Intermediate Similarity	NPC204961
0.8061	Intermediate Similarity	NPC98874
0.8061	Intermediate Similarity	NPC173744
0.8061	Intermediate Similarity	NPC167193
0.8061	Intermediate Similarity	NPC473158
0.8043	Intermediate Similarity	NPC251170
0.8043	Intermediate Similarity	NPC156981
0.8041	Intermediate Similarity	NPC474882
0.8041	Intermediate Similarity	NPC60692
0.8041	Intermediate Similarity	NPC80365
0.8022	Intermediate Similarity	NPC103486
0.8021	Intermediate Similarity	NPC301244
0.8021	Intermediate Similarity	NPC230064
0.8021	Intermediate Similarity	NPC470590
0.8021	Intermediate Similarity	NPC6255
0.8021	Intermediate Similarity	NPC285184
0.8021	Intermediate Similarity	NPC77099
0.8021	Intermediate Similarity	NPC471588
0.8021	Intermediate Similarity	NPC60755
0.8	Intermediate Similarity	NPC225585
0.8	Intermediate Similarity	NPC104545
0.8	Intermediate Similarity	NPC127689
0.8	Intermediate Similarity	NPC474700
0.8	Intermediate Similarity	NPC469637
0.8	Intermediate Similarity	NPC470588
0.8	Intermediate Similarity	NPC287063
0.8	Intermediate Similarity	NPC262043
0.8	Intermediate Similarity	NPC293048
0.8	Intermediate Similarity	NPC61543
0.8	Intermediate Similarity	NPC121798
0.8	Intermediate Similarity	NPC35239
0.8	Intermediate Similarity	NPC59263
0.8	Intermediate Similarity	NPC234346
0.8	Intermediate Similarity	NPC270768
0.8	Intermediate Similarity	NPC130520
0.8	Intermediate Similarity	NPC263393
0.8	Intermediate Similarity	NPC476809
0.798	Intermediate Similarity	NPC89225
0.798	Intermediate Similarity	NPC26413
0.798	Intermediate Similarity	NPC43686
0.7979	Intermediate Similarity	NPC171203
0.7979	Intermediate Similarity	NPC130577
0.7979	Intermediate Similarity	NPC18064
0.7979	Intermediate Similarity	NPC51700
0.7979	Intermediate Similarity	NPC88716
0.7979	Intermediate Similarity	NPC98442
0.7979	Intermediate Similarity	NPC476409
0.7979	Intermediate Similarity	NPC307426
0.7979	Intermediate Similarity	NPC470523
0.7979	Intermediate Similarity	NPC242468
0.7979	Intermediate Similarity	NPC293564
0.7979	Intermediate Similarity	NPC68160
0.7979	Intermediate Similarity	NPC73064
0.7979	Intermediate Similarity	NPC142415
0.7979	Intermediate Similarity	NPC173089

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 NPC147232 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1733
0.2-0.3	3864
0.3-0.4	2179
0.4-0.5	740
0.5-0.6	181
0.6-0.7	146
0.7-0.8	82
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD7285	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD4695	Discontinued
0.8404	Intermediate Similarity	NPD7515	Phase 2
0.8351	Intermediate Similarity	NPD7902	Approved
0.8229	Intermediate Similarity	NPD7748	Approved
0.8041	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD7900	Approved
0.7879	Intermediate Similarity	NPD7614	Phase 1
0.7872	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD5284	Approved
0.7835	Intermediate Similarity	NPD5281	Approved
0.7789	Intermediate Similarity	NPD3573	Approved
0.7766	Intermediate Similarity	NPD5329	Approved
0.7684	Intermediate Similarity	NPD5690	Phase 2
0.766	Intermediate Similarity	NPD4197	Approved
0.7642	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD6881	Approved
0.7629	Intermediate Similarity	NPD6904	Approved
0.7629	Intermediate Similarity	NPD6673	Approved
0.7629	Intermediate Similarity	NPD6080	Approved
0.7624	Intermediate Similarity	NPD6084	Phase 2
0.7624	Intermediate Similarity	NPD6083	Phase 2
0.7619	Intermediate Similarity	NPD6675	Approved
0.7619	Intermediate Similarity	NPD6402	Approved
0.7619	Intermediate Similarity	NPD7128	Approved
0.7619	Intermediate Similarity	NPD5739	Approved
0.76	Intermediate Similarity	NPD5695	Phase 3
0.7593	Intermediate Similarity	NPD6649	Approved
0.7593	Intermediate Similarity	NPD6650	Approved
0.7582	Intermediate Similarity	NPD3617	Approved
0.7576	Intermediate Similarity	NPD6399	Phase 3
0.757	Intermediate Similarity	NPD6373	Approved
0.757	Intermediate Similarity	NPD6372	Approved
0.7549	Intermediate Similarity	NPD5696	Approved
0.7547	Intermediate Similarity	NPD5697	Approved
0.7526	Intermediate Similarity	NPD6672	Approved
0.7526	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD4694	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD5280	Approved
0.7477	Intermediate Similarity	NPD6011	Approved
0.7477	Intermediate Similarity	NPD7320	Approved
0.7476	Intermediate Similarity	NPD5285	Approved
0.7476	Intermediate Similarity	NPD5286	Approved
0.7476	Intermediate Similarity	NPD4696	Approved
0.7475	Intermediate Similarity	NPD6050	Approved
0.7451	Intermediate Similarity	NPD4755	Approved
0.7449	Intermediate Similarity	NPD4753	Phase 2
0.7447	Intermediate Similarity	NPD4221	Approved
0.7447	Intermediate Similarity	NPD4223	Phase 3
0.7431	Intermediate Similarity	NPD6617	Approved
0.7431	Intermediate Similarity	NPD6869	Approved
0.7431	Intermediate Similarity	NPD6847	Approved
0.7431	Intermediate Similarity	NPD8130	Phase 1
0.7426	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5210	Approved
0.7426	Intermediate Similarity	NPD4629	Approved
0.7407	Intermediate Similarity	NPD6012	Approved
0.7407	Intermediate Similarity	NPD6013	Approved
0.7407	Intermediate Similarity	NPD6014	Approved
0.7404	Intermediate Similarity	NPD5223	Approved
0.7383	Intermediate Similarity	NPD5701	Approved
0.7374	Intermediate Similarity	NPD5692	Phase 3
0.7364	Intermediate Similarity	NPD6882	Approved
0.7364	Intermediate Similarity	NPD8297	Approved
0.7353	Intermediate Similarity	NPD7732	Phase 3
0.7353	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4697	Phase 3
0.7353	Intermediate Similarity	NPD5222	Approved
0.7353	Intermediate Similarity	NPD5221	Approved
0.7347	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5226	Approved
0.7333	Intermediate Similarity	NPD5225	Approved
0.7333	Intermediate Similarity	NPD4633	Approved
0.7333	Intermediate Similarity	NPD5224	Approved
0.7333	Intermediate Similarity	NPD5211	Phase 2
0.732	Intermediate Similarity	NPD6098	Approved
0.7308	Intermediate Similarity	NPD4700	Approved
0.73	Intermediate Similarity	NPD5693	Phase 1
0.73	Intermediate Similarity	NPD6079	Approved
0.73	Intermediate Similarity	NPD5694	Approved
0.7282	Intermediate Similarity	NPD5173	Approved
0.7273	Intermediate Similarity	NPD5328	Approved
0.7273	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5174	Approved
0.7264	Intermediate Similarity	NPD5175	Approved
0.7228	Intermediate Similarity	NPD4202	Approved
0.7196	Intermediate Similarity	NPD5141	Approved
0.7157	Intermediate Similarity	NPD6001	Approved
0.7143	Intermediate Similarity	NPD4519	Discontinued
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD4690	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD4689	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD4693	Phase 3
0.7143	Intermediate Similarity	NPD5205	Approved
0.7143	Intermediate Similarity	NPD4138	Approved
0.7143	Intermediate Similarity	NPD4688	Approved
0.7143	Intermediate Similarity	NPD4623	Approved
0.7143	Intermediate Similarity	NPD4632	Approved
0.7129	Intermediate Similarity	NPD8035	Phase 2
0.7129	Intermediate Similarity	NPD8034	Phase 2
0.7113	Intermediate Similarity	NPD4786	Approved
0.7113	Intermediate Similarity	NPD3133	Approved
0.7113	Intermediate Similarity	NPD3665	Phase 1
0.7113	Intermediate Similarity	NPD3666	Approved
0.7105	Intermediate Similarity	NPD7115	Discovery
0.7103	Intermediate Similarity	NPD4754	Approved
0.7083	Intermediate Similarity	NPD3667	Approved
0.7043	Intermediate Similarity	NPD6335	Approved
0.7041	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD8328	Phase 3
0.703	Intermediate Similarity	NPD5207	Approved
0.7018	Intermediate Similarity	NPD6274	Approved
0.701	Intermediate Similarity	NPD4788	Approved
0.7009	Intermediate Similarity	NPD5091	Approved
0.7	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD6903	Approved
0.7	Intermediate Similarity	NPD5208	Approved
0.7	Intermediate Similarity	NPD4729	Approved
0.7	Intermediate Similarity	NPD4730	Approved
0.6983	Remote Similarity	NPD7101	Approved
0.6983	Remote Similarity	NPD7100	Approved
0.6972	Remote Similarity	NPD4768	Approved
0.6972	Remote Similarity	NPD4767	Approved
0.6972	Remote Similarity	NPD6008	Approved
0.6957	Remote Similarity	NPD6009	Approved
0.6957	Remote Similarity	NPD6317	Approved
0.6947	Remote Similarity	NPD4195	Approved
0.6923	Remote Similarity	NPD5654	Approved
0.6909	Remote Similarity	NPD6614	Approved
0.6897	Remote Similarity	NPD6314	Approved
0.6897	Remote Similarity	NPD6313	Approved
0.6893	Remote Similarity	NPD5133	Approved
0.6887	Remote Similarity	NPD7638	Approved
0.6875	Remote Similarity	NPD5250	Approved
0.6875	Remote Similarity	NPD5249	Phase 3
0.6875	Remote Similarity	NPD5248	Approved
0.6875	Remote Similarity	NPD5135	Approved
0.6875	Remote Similarity	NPD5169	Approved
0.6875	Remote Similarity	NPD4634	Approved
0.6875	Remote Similarity	NPD5247	Approved
0.6875	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD6868	Approved
0.6864	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7639	Approved
0.6822	Remote Similarity	NPD7640	Approved
0.6814	Remote Similarity	NPD5127	Approved
0.6814	Remote Similarity	NPD5215	Approved
0.6814	Remote Similarity	NPD5217	Approved
0.6814	Remote Similarity	NPD5216	Approved
0.6813	Remote Similarity	NPD4691	Approved
0.6804	Remote Similarity	NPD8028	Phase 2
0.6803	Remote Similarity	NPD7736	Approved
0.6796	Remote Similarity	NPD6411	Approved
0.6792	Remote Similarity	NPD5959	Approved
0.6786	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6319	Approved
0.6771	Remote Similarity	NPD7645	Phase 2
0.6768	Remote Similarity	NPD3668	Phase 3
0.675	Remote Similarity	NPD7604	Phase 2
0.6735	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6909	Approved
0.6723	Remote Similarity	NPD6908	Approved
0.6723	Remote Similarity	NPD5983	Phase 2
0.6703	Remote Similarity	NPD4137	Phase 3
0.6701	Remote Similarity	NPD7525	Registered
0.6701	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.67	Remote Similarity	NPD1694	Approved
0.6699	Remote Similarity	NPD4096	Approved
0.6696	Remote Similarity	NPD5168	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD4518	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6336	Discontinued
0.6639	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6638	Remote Similarity	NPD5167	Approved
0.6636	Remote Similarity	NPD6052	Approved
0.6633	Remote Similarity	NPD4139	Approved
0.6633	Remote Similarity	NPD4692	Approved
0.663	Remote Similarity	NPD4747	Approved
0.6607	Remote Similarity	NPD6412	Phase 2
0.6602	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6101	Approved
0.6596	Remote Similarity	NPD4058	Approved
0.6596	Remote Similarity	NPD5733	Approved
0.6591	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7078	Approved
0.6574	Remote Similarity	NPD4225	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