NPASS Compound

Structure

NPC472760 OpenBabel07101719152D 43 46 0 0 1 0 0 0 0 0999 V2000 -7.1219 -12.8949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2521 1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 -0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1069 -11.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2335 -11.4080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2186 -10.4081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3452 -9.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3302 -8.9213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6651 -4.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7917 -3.9736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4568 -8.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6801 -5.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7767 -2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4418 -7.4344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5535 -5.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 -2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3011 1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4452 3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5684 -6.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9921 2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1073 4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7100 -7.4603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5799 3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 2.9158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 33 1 0 0 0 0 5 33 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 13 1 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 15 18 2 0 0 0 0 16 27 1 0 0 0 0 17 27 1 0 0 0 0 18 30 1 0 0 0 0 19 24 2 0 0 0 0 19 29 1 0 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 35 1 0 0 0 0 22 26 1 0 0 0 0 22 34 1 0 0 0 0 23 26 1 0 0 0 0 23 37 1 0 0 0 0 24 32 1 0 0 0 0 25 36 1 6 0 0 0 27 38 2 0 0 0 0 28 31 1 0 0 0 0 28 36 1 6 0 0 0 29 34 1 1 0 0 0 29 36 1 0 0 0 0 30 39 2 0 0 0 0 30 43 1 0 0 0 0 31 33 1 0 0 0 0 31 35 1 6 0 0 0 32 34 1 0 0 0 0 32 40 2 0 0 0 0 33 35 1 0 0 0 0 34 41 1 1 0 0 0 35 43 1 6 0 0 0 36 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.36
Volume:	637.426
LogP:	5.412
LogD:	4.008
LogS:	-5.095
# Rotatable Bonds:	14
TPSA:	121.13
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.085
Synthetic Accessibility Score:	5.219
Fsp3:	0.639
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.872
MDCK Permeability:	2.2261659978539683e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.185
20% Bioavailability (F20%):	0.211
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	97.24677276611328%
Volume Distribution (VD):	1.631
Pgp-substrate:	2.8601856231689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.452
CYP2C19-substrate:	0.706
CYP2C9-inhibitor:	0.498
CYP2C9-substrate:	0.463
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.421

ADMET: Excretion

Clearance (CL):	2.301
Half-life (T1/2):	0.018

ADMET: Toxicity

hERG Blockers:	0.501
Human Hepatotoxicity (H-HT):	0.616
Drug-inuced Liver Injury (DILI):	0.195
AMES Toxicity:	0.584
Rat Oral Acute Toxicity:	0.657
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.928
Carcinogencity:	0.11
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.85

Download Data

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

Natural Product: NPC472760

Natural Product ID:	NPC472760
*Common Name:**	VRNFFDMZKHRMEH-KNMGUQBGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VRNFFDMZKHRMEH-KNMGUQBGSA-N
Standard InCHI:	InChI=1S/C36H50O7/c1-6-7-8-9-10-13-16-27(38)17-14-11-12-15-18-30(39)43-35-21-25(3)36(42)28(31(35)33(35,4)5)20-26(23-37)22-34(41)29(36)19-24(2)32(34)40/h11-12,14-15,17-20,25,28-29,31,37,41-42H,6-10,13,16,21-23H2,1-5H3/b12-11+,17-14+,18-15+/t25-,28+,29-,31-,34-,35+,36-/m1/s1
SMILES:	CCCCCCCCC(=O)C=CC=CC=CC(=O)OC12CC(C3(C(C1C2(C)C)C=C(CC4(C3C=C(C4=O)C)O)CO)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582007
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]

☑ 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
EC50	5
Others	9

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[492554]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[492554]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[492554]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	13000.0	nM	PMID[492554]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	13000.0	nM	PMID[492554]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	43.0	nM	PMID[492554]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	18.0	nM	PMID[492554]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	299.0	n.a.	PMID[492554]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	1431.0	n.a.	PMID[492554]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	2200.0	nM	PMID[492554]
NPT338	Organism	Sindbis virus	Sindbis virus	EC50	=	11000.0	nM	PMID[492554]
NPT856	Organism	Semliki forest virus	Semliki forest virus	EC50	>	168000.0	nM	PMID[492554]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	5.9	n.a.	PMID[492554]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	1.2	n.a.	PMID[492554]

☑ 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 NPC472760 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	227
0.1-0.2	1275
0.2-0.3	3914
0.3-0.4	7006
0.4-0.5	14268
0.5-0.6	9237
0.6-0.7	5427
0.7-0.8	1203
0.8-0.85	28
0.85-0.9	35
0.9-0.95	57
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC180640
0.9818	High Similarity	NPC185876
0.9818	High Similarity	NPC19336
0.9725	High Similarity	NPC153651
0.963	High Similarity	NPC71889
0.9541	High Similarity	NPC474872
0.9537	High Similarity	NPC151216
0.9537	High Similarity	NPC17138
0.9537	High Similarity	NPC221511
0.9537	High Similarity	NPC215643
0.9537	High Similarity	NPC101825
0.9537	High Similarity	NPC89227
0.9537	High Similarity	NPC265499
0.9537	High Similarity	NPC170212
0.9474	High Similarity	NPC145238
0.945	High Similarity	NPC474937
0.9444	High Similarity	NPC96739
0.9444	High Similarity	NPC158523
0.9444	High Similarity	NPC474871
0.9444	High Similarity	NPC174471
0.9444	High Similarity	NPC475937
0.9444	High Similarity	NPC260786
0.9358	High Similarity	NPC475391
0.9352	High Similarity	NPC153036
0.9292	High Similarity	NPC472759
0.9292	High Similarity	NPC329080
0.9211	High Similarity	NPC52839
0.9204	High Similarity	NPC156745
0.9204	High Similarity	NPC236918
0.913	High Similarity	NPC257017
0.913	High Similarity	NPC162009
0.9123	High Similarity	NPC471126
0.9123	High Similarity	NPC471128
0.9123	High Similarity	NPC157252
0.9123	High Similarity	NPC475885
0.9123	High Similarity	NPC145182
0.9099	High Similarity	NPC477091
0.9035	High Similarity	NPC255081
0.9035	High Similarity	NPC275696
0.9035	High Similarity	NPC5991
0.9035	High Similarity	NPC471108
0.9035	High Similarity	NPC22628
0.9035	High Similarity	NPC5989
0.9027	High Similarity	NPC10721
0.8947	High Similarity	NPC146280
0.8947	High Similarity	NPC472397
0.8947	High Similarity	NPC124676
0.8947	High Similarity	NPC472758
0.8947	High Similarity	NPC471125
0.8947	High Similarity	NPC171905
0.8938	High Similarity	NPC234858
0.8938	High Similarity	NPC471127
0.8938	High Similarity	NPC154363
0.8908	High Similarity	NPC236999
0.8889	High Similarity	NPC472399
0.886	High Similarity	NPC156252
0.8803	High Similarity	NPC19464
0.8761	High Similarity	NPC472757
0.8718	High Similarity	NPC472401
0.8684	High Similarity	NPC472400
0.8667	High Similarity	NPC471940
0.8583	High Similarity	NPC471939
0.8583	High Similarity	NPC222307
0.85	High Similarity	NPC473919
0.85	High Similarity	NPC473709
0.8443	Intermediate Similarity	NPC270109
0.8417	Intermediate Similarity	NPC473802
0.8407	Intermediate Similarity	NPC163004
0.8276	Intermediate Similarity	NPC469463
0.8276	Intermediate Similarity	NPC469454
0.8276	Intermediate Similarity	NPC469496
0.8205	Intermediate Similarity	NPC133677
0.8205	Intermediate Similarity	NPC138303
0.8205	Intermediate Similarity	NPC67290
0.819	Intermediate Similarity	NPC123855
0.819	Intermediate Similarity	NPC76550
0.8175	Intermediate Similarity	NPC469674
0.8136	Intermediate Similarity	NPC148458
0.812	Intermediate Similarity	NPC46269
0.812	Intermediate Similarity	NPC106395
0.812	Intermediate Similarity	NPC474271
0.811	Intermediate Similarity	NPC182266
0.811	Intermediate Similarity	NPC471136
0.811	Intermediate Similarity	NPC100017
0.811	Intermediate Similarity	NPC475154
0.811	Intermediate Similarity	NPC475500
0.811	Intermediate Similarity	NPC223356
0.811	Intermediate Similarity	NPC471137
0.811	Intermediate Similarity	NPC473548
0.8103	Intermediate Similarity	NPC179798
0.8103	Intermediate Similarity	NPC304180
0.8083	Intermediate Similarity	NPC472667
0.808	Intermediate Similarity	NPC221414
0.8053	Intermediate Similarity	NPC118911
0.8036	Intermediate Similarity	NPC478156
0.8034	Intermediate Similarity	NPC71348
0.8034	Intermediate Similarity	NPC138757
0.8017	Intermediate Similarity	NPC5103
0.8	Intermediate Similarity	NPC102843
0.8	Intermediate Similarity	NPC322903
0.7984	Intermediate Similarity	NPC68282
0.7983	Intermediate Similarity	NPC270958
0.7966	Intermediate Similarity	NPC56448
0.7966	Intermediate Similarity	NPC25909
0.7953	Intermediate Similarity	NPC473485
0.7953	Intermediate Similarity	NPC180902
0.7953	Intermediate Similarity	NPC475139
0.7953	Intermediate Similarity	NPC474508
0.7931	Intermediate Similarity	NPC137911
0.7931	Intermediate Similarity	NPC228477
0.7931	Intermediate Similarity	NPC273433
0.7917	Intermediate Similarity	NPC23046
0.7917	Intermediate Similarity	NPC474518
0.7917	Intermediate Similarity	NPC239273
0.7895	Intermediate Similarity	NPC239162
0.7891	Intermediate Similarity	NPC476111
0.7891	Intermediate Similarity	NPC469673
0.7881	Intermediate Similarity	NPC100267
0.7881	Intermediate Similarity	NPC475524
0.7876	Intermediate Similarity	NPC155332
0.7876	Intermediate Similarity	NPC114540
0.7876	Intermediate Similarity	NPC476081
0.7876	Intermediate Similarity	NPC162973
0.7876	Intermediate Similarity	NPC32577
0.7874	Intermediate Similarity	NPC251564
0.7874	Intermediate Similarity	NPC475606
0.7874	Intermediate Similarity	NPC477189
0.7874	Intermediate Similarity	NPC196921
0.7874	Intermediate Similarity	NPC475314
0.7874	Intermediate Similarity	NPC220757
0.7869	Intermediate Similarity	NPC114939
0.7869	Intermediate Similarity	NPC145074
0.7869	Intermediate Similarity	NPC41123
0.7869	Intermediate Similarity	NPC476962
0.7869	Intermediate Similarity	NPC143755
0.7863	Intermediate Similarity	NPC238850
0.7863	Intermediate Similarity	NPC257240
0.7857	Intermediate Similarity	NPC474718
0.7857	Intermediate Similarity	NPC470074
0.7851	Intermediate Similarity	NPC118638
0.7851	Intermediate Similarity	NPC146786
0.7851	Intermediate Similarity	NPC257457
0.7851	Intermediate Similarity	NPC311554
0.7846	Intermediate Similarity	NPC243902
0.7845	Intermediate Similarity	NPC476479
0.784	Intermediate Similarity	NPC63186
0.784	Intermediate Similarity	NPC15095
0.7833	Intermediate Similarity	NPC176840
0.7833	Intermediate Similarity	NPC179626
0.7829	Intermediate Similarity	NPC476823
0.7826	Intermediate Similarity	NPC477125
0.7826	Intermediate Similarity	NPC34768
0.7826	Intermediate Similarity	NPC469607
0.7823	Intermediate Similarity	NPC469789
0.7815	Intermediate Similarity	NPC202889
0.7812	Intermediate Similarity	NPC34963
0.7805	Intermediate Similarity	NPC67569
0.7805	Intermediate Similarity	NPC310511
0.7797	Intermediate Similarity	NPC473921
0.7797	Intermediate Similarity	NPC317107
0.7797	Intermediate Similarity	NPC231589
0.7797	Intermediate Similarity	NPC475668
0.7797	Intermediate Similarity	NPC475480
0.7797	Intermediate Similarity	NPC118860
0.7797	Intermediate Similarity	NPC214797
0.7795	Intermediate Similarity	NPC162495
0.7795	Intermediate Similarity	NPC35109
0.7788	Intermediate Similarity	NPC115862
0.7788	Intermediate Similarity	NPC115899
0.7788	Intermediate Similarity	NPC471412
0.7787	Intermediate Similarity	NPC470186
0.7787	Intermediate Similarity	NPC472933
0.7778	Intermediate Similarity	NPC241927
0.7778	Intermediate Similarity	NPC258543
0.7778	Intermediate Similarity	NPC47951
0.7769	Intermediate Similarity	NPC471854
0.7769	Intermediate Similarity	NPC476959
0.7759	Intermediate Similarity	NPC187435
0.7759	Intermediate Similarity	NPC67321
0.7759	Intermediate Similarity	NPC475294
0.7752	Intermediate Similarity	NPC58029
0.775	Intermediate Similarity	NPC238667
0.7748	Intermediate Similarity	NPC284518
0.7744	Intermediate Similarity	NPC25887
0.7742	Intermediate Similarity	NPC23786
0.7742	Intermediate Similarity	NPC222688
0.7742	Intermediate Similarity	NPC470265
0.7734	Intermediate Similarity	NPC241935
0.7734	Intermediate Similarity	NPC279478
0.7731	Intermediate Similarity	NPC4573
0.7731	Intermediate Similarity	NPC221144
0.7731	Intermediate Similarity	NPC90952
0.7731	Intermediate Similarity	NPC317687
0.7731	Intermediate Similarity	NPC470063
0.7731	Intermediate Similarity	NPC234042
0.7731	Intermediate Similarity	NPC152117
0.7731	Intermediate Similarity	NPC277769
0.7731	Intermediate Similarity	NPC170487
0.7727	Intermediate Similarity	NPC217624
0.7727	Intermediate Similarity	NPC181393

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 NPC472760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1530
0.2-0.3	3510
0.3-0.4	2452
0.4-0.5	979
0.5-0.6	303
0.6-0.7	171
0.7-0.8	7
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
0.7863	Intermediate Similarity	NPD6371	Approved
0.7542	Intermediate Similarity	NPD6899	Approved
0.7542	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6650	Approved
0.748	Intermediate Similarity	NPD7115	Discovery
0.7458	Intermediate Similarity	NPD5697	Approved
0.7438	Intermediate Similarity	NPD8297	Approved
0.7417	Intermediate Similarity	NPD7102	Approved
0.7417	Intermediate Similarity	NPD6883	Approved
0.7417	Intermediate Similarity	NPD7290	Approved
0.7391	Intermediate Similarity	NPD7639	Approved
0.7391	Intermediate Similarity	NPD7640	Approved
0.7373	Intermediate Similarity	NPD7128	Approved
0.7373	Intermediate Similarity	NPD5739	Approved
0.7373	Intermediate Similarity	NPD6675	Approved
0.7373	Intermediate Similarity	NPD6402	Approved
0.7355	Intermediate Similarity	NPD6617	Approved
0.7355	Intermediate Similarity	NPD6869	Approved
0.7355	Intermediate Similarity	NPD6847	Approved
0.7333	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD6014	Approved
0.7333	Intermediate Similarity	NPD6013	Approved
0.7333	Intermediate Similarity	NPD6012	Approved
0.7333	Intermediate Similarity	NPD6372	Approved
0.7304	Intermediate Similarity	NPD7638	Approved
0.7295	Intermediate Similarity	NPD6882	Approved
0.7266	Intermediate Similarity	NPD7604	Phase 2
0.7265	Intermediate Similarity	NPD5211	Phase 2
0.725	Intermediate Similarity	NPD7320	Approved
0.725	Intermediate Similarity	NPD6011	Approved
0.7241	Intermediate Similarity	NPD6648	Approved
0.7236	Intermediate Similarity	NPD4632	Approved
0.7179	Intermediate Similarity	NPD5344	Discontinued
0.7167	Intermediate Similarity	NPD5701	Approved
0.7167	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6319	Approved
0.7156	Intermediate Similarity	NPD1696	Phase 3
0.7143	Intermediate Similarity	NPD5141	Approved
0.7107	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5285	Approved
0.7094	Intermediate Similarity	NPD4696	Approved
0.7094	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD6008	Approved
0.7077	Intermediate Similarity	NPD7492	Approved
0.7069	Intermediate Similarity	NPD6083	Phase 2
0.7069	Intermediate Similarity	NPD6084	Phase 2
0.7063	Intermediate Similarity	NPD6009	Approved
0.7049	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7736	Approved
0.7043	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6054	Approved
0.7023	Intermediate Similarity	NPD6616	Approved
0.7016	Intermediate Similarity	NPD6053	Discontinued
0.7009	Intermediate Similarity	NPD4225	Approved
0.6992	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5983	Phase 2
0.6975	Remote Similarity	NPD4633	Approved
0.6975	Remote Similarity	NPD5224	Approved
0.6975	Remote Similarity	NPD5225	Approved
0.6975	Remote Similarity	NPD5226	Approved
0.697	Remote Similarity	NPD7078	Approved
0.6953	Remote Similarity	NPD7100	Approved
0.6953	Remote Similarity	NPD7101	Approved
0.6935	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4755	Approved
0.6923	Remote Similarity	NPD6370	Approved
0.6917	Remote Similarity	NPD5175	Approved
0.6917	Remote Similarity	NPD5174	Approved
0.6897	Remote Similarity	NPD5695	Phase 3
0.6894	Remote Similarity	NPD7507	Approved
0.6894	Remote Similarity	NPD6336	Discontinued
0.6891	Remote Similarity	NPD5223	Approved
0.6875	Remote Similarity	NPD6335	Approved
0.687	Remote Similarity	NPD5778	Approved
0.687	Remote Similarity	NPD5779	Approved
0.6864	Remote Similarity	NPD5696	Approved
0.6855	Remote Similarity	NPD4634	Approved
0.685	Remote Similarity	NPD6274	Approved
0.6846	Remote Similarity	NPD6015	Approved
0.6846	Remote Similarity	NPD6016	Approved
0.6842	Remote Similarity	NPD5785	Approved
0.6842	Remote Similarity	NPD8293	Discontinued
0.6842	Remote Similarity	NPD7838	Discovery
0.6833	Remote Similarity	NPD7632	Discontinued
0.6829	Remote Similarity	NPD6686	Approved
0.681	Remote Similarity	NPD5282	Discontinued
0.6807	Remote Similarity	NPD4700	Approved
0.6797	Remote Similarity	NPD6317	Approved
0.6794	Remote Similarity	NPD5988	Approved
0.6783	Remote Similarity	NPD5284	Approved
0.6783	Remote Similarity	NPD5281	Approved
0.678	Remote Similarity	NPD7902	Approved
0.6769	Remote Similarity	NPD6059	Approved
0.6765	Remote Similarity	NPD7260	Phase 2
0.6754	Remote Similarity	NPD1695	Approved
0.6752	Remote Similarity	NPD5210	Approved
0.6752	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4629	Approved
0.6748	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6314	Approved
0.6744	Remote Similarity	NPD6313	Approved
0.6741	Remote Similarity	NPD7319	Approved
0.6724	Remote Similarity	NPD6399	Phase 3
0.6723	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7503	Approved
0.6718	Remote Similarity	NPD8516	Approved
0.6718	Remote Similarity	NPD8517	Approved
0.6718	Remote Similarity	NPD8515	Approved
0.6718	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD8513	Phase 3
0.6696	Remote Similarity	NPD46	Approved
0.6696	Remote Similarity	NPD6698	Approved
0.6696	Remote Similarity	NPD1694	Approved
0.6695	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5222	Approved
0.6695	Remote Similarity	NPD5221	Approved
0.6694	Remote Similarity	NPD4730	Approved
0.6694	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6639	Remote Similarity	NPD5173	Approved
0.6638	Remote Similarity	NPD7637	Suspended
0.6638	Remote Similarity	NPD5693	Phase 1
0.6638	Remote Similarity	NPD5694	Approved
0.6638	Remote Similarity	NPD7983	Approved
0.6638	Remote Similarity	NPD6079	Approved
0.6638	Remote Similarity	NPD6050	Approved
0.6617	Remote Similarity	NPD8328	Phase 3
0.6615	Remote Similarity	NPD7328	Approved
0.6615	Remote Similarity	NPD7327	Approved
0.6609	Remote Similarity	NPD4753	Phase 2
0.6591	Remote Similarity	NPD6909	Approved
0.6591	Remote Similarity	NPD8033	Approved
0.6591	Remote Similarity	NPD6908	Approved
0.6589	Remote Similarity	NPD6868	Approved
0.6587	Remote Similarity	NPD5247	Approved
0.6587	Remote Similarity	NPD5249	Phase 3
0.6587	Remote Similarity	NPD5250	Approved
0.6587	Remote Similarity	NPD5251	Approved
0.6587	Remote Similarity	NPD5248	Approved
0.6577	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7516	Approved
0.656	Remote Similarity	NPD5128	Approved
0.6555	Remote Similarity	NPD4697	Phase 3
0.6552	Remote Similarity	NPD5692	Phase 3
0.6535	Remote Similarity	NPD5216	Approved
0.6535	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5215	Approved
0.6535	Remote Similarity	NPD5217	Approved
0.6532	Remote Similarity	NPD4767	Approved
0.6532	Remote Similarity	NPD4768	Approved
0.6525	Remote Similarity	NPD7900	Approved
0.6525	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5737	Approved
0.6522	Remote Similarity	NPD6672	Approved
0.6515	Remote Similarity	NPD8294	Approved
0.6515	Remote Similarity	NPD8377	Approved
0.6504	Remote Similarity	NPD4754	Approved
0.6496	Remote Similarity	NPD7515	Phase 2
0.6496	Remote Similarity	NPD6411	Approved
0.6486	Remote Similarity	NPD7236	Approved
0.6471	Remote Similarity	NPD8074	Phase 3
0.6466	Remote Similarity	NPD8296	Approved
0.6466	Remote Similarity	NPD6904	Approved
0.6466	Remote Similarity	NPD6921	Approved
0.6466	Remote Similarity	NPD8380	Approved
0.6466	Remote Similarity	NPD6673	Approved
0.6466	Remote Similarity	NPD8335	Approved
0.6466	Remote Similarity	NPD5328	Approved
0.6466	Remote Similarity	NPD8378	Approved
0.6466	Remote Similarity	NPD8379	Approved
0.6466	Remote Similarity	NPD6080	Approved
0.6457	Remote Similarity	NPD5135	Approved
0.6457	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5169	Approved
0.6441	Remote Similarity	NPD4202	Approved
0.6435	Remote Similarity	NPD3573	Approved
0.6434	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD5209	Approved
0.641	Remote Similarity	NPD5207	Approved
0.6406	Remote Similarity	NPD5127	Approved
0.6404	Remote Similarity	NPD5363	Approved
0.6387	Remote Similarity	NPD6001	Approved
0.6372	Remote Similarity	NPD5362	Discontinued
0.6372	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD5959	Approved
0.6357	Remote Similarity	NPD6845	Suspended
0.6356	Remote Similarity	NPD8035	Phase 2
0.6356	Remote Similarity	NPD8034	Phase 2
0.6349	Remote Similarity	NPD6412	Phase 2
0.6348	Remote Similarity	NPD3618	Phase 1
0.6348	Remote Similarity	NPD5279	Phase 3
0.6348	Remote Similarity	NPD4694	Approved
0.6348	Remote Similarity	NPD5690	Phase 2
0.6348	Remote Similarity	NPD5280	Approved
0.6325	Remote Similarity	NPD6101	Approved
0.6325	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7338	Clinical (unspecified phase)

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