NPASS Compound

Structure

CID227361 OpenBabel06191716022D 41 45 0 0 1 0 0 0 0 0999 V2000 -2.6564 -5.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2256 -1.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 2.3716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8842 -3.5778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6112 -4.2735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 -0.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3395 -4.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4499 -4.8181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9365 -2.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1572 -3.3825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6438 -1.1435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7542 -1.5452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7415 -2.0749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9602 -0.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4485 -4.8705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4825 -1.6882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2096 -2.3839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6452 -1.0912 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8731 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 2.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 2.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 4.8065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 3.8410 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4846 -2.7440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 5.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 4.3237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 4.3237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3816 1.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3529 0.7811 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 -0.6354 5.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 38 1 0 0 0 0 4 7 1 0 0 0 0 4 9 1 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 19 1 0 0 0 0 8 19 2 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 27 2 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 24 2 0 0 0 0 15 26 1 0 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 21 1 0 0 0 0 17 34 2 0 0 0 0 18 39 1 0 0 0 0 18 40 1 0 0 0 0 22 41 1 1 0 0 0 23 24 1 0 0 0 0 23 30 2 0 0 0 0 24 27 1 0 0 0 0 25 29 1 0 0 0 0 25 32 1 0 0 0 0 26 29 2 0 0 0 0 26 33 1 0 0 0 0 27 38 1 0 0 0 0 28 31 2 0 0 0 0 28 39 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 31 40 1 0 0 0 0 32 35 2 0 0 0 0 32 41 1 0 0 0 0 33 36 2 0 0 0 0 33 37 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	557.2
Volume:	566.29
LogP:	6.73
LogD:	4.664
LogS:	-7.552
# Rotatable Bonds:	6
TPSA:	114.2
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.081
Synthetic Accessibility Score:	4.412
Fsp3:	0.312
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:	-4.808
MDCK Permeability:	2.618454527691938e-05
Pgp-inhibitor:	0.226
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	98.93736267089844%
Volume Distribution (VD):	0.224
Pgp-substrate:	1.3938599824905396%

ADMET: Metabolism

CYP1A2-inhibitor:	0.686
CYP1A2-substrate:	0.161
CYP2C19-inhibitor:	0.973
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.965
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.933
CYP2D6-substrate:	0.539
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	4.988
Half-life (T1/2):	0.053

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.891
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.981
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.963
Carcinogencity:	0.901
Eye Corrosion:	0.004
Eye Irritation:	0.247
Respiratory Toxicity:	0.8

Download Data

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

Natural Product: NPC227361

Natural Product ID:	NPC227361
*Common Name:**	Aristoloterpenate-I
IUPAC Name:	[(1R,2Z,6E,10E)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl] 8-methoxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylate
Synonyms:	Aristoloterpenate-I
Standard InCHIKey:	CNCKKGCRDGSHDH-PTDIUHGLSA-N
Standard InCHI:	InChI=1S/C32H31NO8/c1-19-7-4-9-20(2)13-22(14-21(17-34)10-5-8-19)41-32(35)25-16-28-31(40-18-39-28)30-23-11-6-12-27(38-3)24(23)15-26(29(25)30)33(36)37/h6,8-9,11-12,14-17,22H,4-5,7,10,13,18H2,1-3H3/b19-8+,20-9+,21-14-/t22-/m1/s1
SMILES:	C/C/1=CCC/C(=C/[C@@H](C/C(=C/CC1)/C)OC(=O)c1cc2c(c3c4cccc(c4cc(c13)N(=O)=O)OC)OCO2)/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505464
PubChem CID:	10347702
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0002664] Aristolochic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075784]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	root and stem	n.a.	n.a.	PMID[10096848]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	stem	n.a.	PMID[10096848]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	root	n.a.	PMID[10096848]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	amniotic fluid	n.a.	Database[Article]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4830.0	nM	PMID[548128]

☑ 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 NPC227361 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	439
0.1-0.2	2099
0.2-0.3	5589
0.3-0.4	11771
0.4-0.5	5847
0.5-0.6	12220
0.6-0.7	4609
0.7-0.8	107
0.8-0.85	0
0.85-0.9	0
0.9-0.95	7
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC124658
0.9894	High Similarity	NPC186569
0.9894	High Similarity	NPC61731
0.9742	High Similarity	NPC256422
0.9577	High Similarity	NPC38961
0.9378	High Similarity	NPC85661
0.9326	High Similarity	NPC46679
0.9278	High Similarity	NPC171882
0.9278	High Similarity	NPC121510
0.9235	High Similarity	NPC91234
0.9141	High Similarity	NPC290227
0.9095	High Similarity	NPC240684
0.7933	Intermediate Similarity	NPC90185
0.7877	Intermediate Similarity	NPC55470
0.7656	Intermediate Similarity	NPC207971
0.7619	Intermediate Similarity	NPC118332
0.7594	Intermediate Similarity	NPC100573
0.7594	Intermediate Similarity	NPC207873
0.7586	Intermediate Similarity	NPC296742
0.7547	Intermediate Similarity	NPC222561
0.7547	Intermediate Similarity	NPC308943
0.7537	Intermediate Similarity	NPC224293
0.7536	Intermediate Similarity	NPC268077
0.75	Intermediate Similarity	NPC23080
0.75	Intermediate Similarity	NPC312531
0.75	Intermediate Similarity	NPC193906
0.75	Intermediate Similarity	NPC112676
0.7488	Intermediate Similarity	NPC69213
0.7488	Intermediate Similarity	NPC159101
0.7474	Intermediate Similarity	NPC125713
0.7461	Intermediate Similarity	NPC239113
0.7461	Intermediate Similarity	NPC109765
0.7461	Intermediate Similarity	NPC115123
0.7424	Intermediate Similarity	NPC471923
0.7423	Intermediate Similarity	NPC202495
0.7387	Intermediate Similarity	NPC473531
0.7387	Intermediate Similarity	NPC475453
0.7381	Intermediate Similarity	NPC5374
0.7358	Intermediate Similarity	NPC54179
0.7356	Intermediate Similarity	NPC29472
0.7347	Intermediate Similarity	NPC78944
0.7333	Intermediate Similarity	NPC19600
0.7333	Intermediate Similarity	NPC71124
0.7327	Intermediate Similarity	NPC260118
0.7308	Intermediate Similarity	NPC254957
0.7306	Intermediate Similarity	NPC298449
0.7304	Intermediate Similarity	NPC249405
0.7296	Intermediate Similarity	NPC474043
0.7291	Intermediate Similarity	NPC215747
0.7291	Intermediate Similarity	NPC192939
0.7286	Intermediate Similarity	NPC477884
0.7277	Intermediate Similarity	NPC265383
0.7277	Intermediate Similarity	NPC127827
0.7277	Intermediate Similarity	NPC473697
0.7273	Intermediate Similarity	NPC116838
0.7273	Intermediate Similarity	NPC22130
0.724	Intermediate Similarity	NPC300983
0.724	Intermediate Similarity	NPC475722
0.7237	Intermediate Similarity	NPC227033
0.7228	Intermediate Similarity	NPC52598
0.7222	Intermediate Similarity	NPC15212
0.7222	Intermediate Similarity	NPC319749
0.722	Intermediate Similarity	NPC28425
0.7198	Intermediate Similarity	NPC474009
0.7192	Intermediate Similarity	NPC471922
0.7192	Intermediate Similarity	NPC471921
0.7192	Intermediate Similarity	NPC474075
0.7192	Intermediate Similarity	NPC20114
0.7192	Intermediate Similarity	NPC471920
0.7192	Intermediate Similarity	NPC114550
0.7192	Intermediate Similarity	NPC292712
0.7192	Intermediate Similarity	NPC312006
0.7192	Intermediate Similarity	NPC129930
0.7171	Intermediate Similarity	NPC179704
0.7171	Intermediate Similarity	NPC196771
0.7171	Intermediate Similarity	NPC119579
0.7164	Intermediate Similarity	NPC474042
0.7164	Intermediate Similarity	NPC174734
0.7157	Intermediate Similarity	NPC82733
0.7157	Intermediate Similarity	NPC184624
0.7157	Intermediate Similarity	NPC190461
0.7157	Intermediate Similarity	NPC76458
0.7156	Intermediate Similarity	NPC46990
0.715	Intermediate Similarity	NPC219170
0.715	Intermediate Similarity	NPC180253
0.7143	Intermediate Similarity	NPC160113
0.7143	Intermediate Similarity	NPC476220
0.7143	Intermediate Similarity	NPC302001
0.7143	Intermediate Similarity	NPC234730
0.7136	Intermediate Similarity	NPC258322
0.7136	Intermediate Similarity	NPC191352
0.7136	Intermediate Similarity	NPC276060
0.7122	Intermediate Similarity	NPC311936
0.7122	Intermediate Similarity	NPC193377
0.7121	Intermediate Similarity	NPC325122
0.7108	Intermediate Similarity	NPC287588
0.7107	Intermediate Similarity	NPC261484
0.7101	Intermediate Similarity	NPC275690
0.7101	Intermediate Similarity	NPC161609
0.71	Intermediate Similarity	NPC280778
0.71	Intermediate Similarity	NPC19948
0.71	Intermediate Similarity	NPC198796
0.7098	Intermediate Similarity	NPC24193
0.7094	Intermediate Similarity	NPC117911
0.7089	Intermediate Similarity	NPC73020
0.7089	Intermediate Similarity	NPC215098
0.7089	Intermediate Similarity	NPC124302
0.7089	Intermediate Similarity	NPC46744
0.7089	Intermediate Similarity	NPC70290
0.7089	Intermediate Similarity	NPC14622
0.7081	Intermediate Similarity	NPC474904
0.7075	Intermediate Similarity	NPC470023
0.7073	Intermediate Similarity	NPC477881
0.7073	Intermediate Similarity	NPC316539
0.7071	Intermediate Similarity	NPC143328
0.7053	Intermediate Similarity	NPC35266
0.7051	Intermediate Similarity	NPC244606
0.7051	Intermediate Similarity	NPC156728
0.705	Intermediate Similarity	NPC296540
0.705	Intermediate Similarity	NPC469889
0.705	Intermediate Similarity	NPC309335
0.7047	Intermediate Similarity	NPC181464
0.7045	Intermediate Similarity	NPC25961
0.7044	Intermediate Similarity	NPC227683
0.7042	Intermediate Similarity	NPC470021
0.7039	Intermediate Similarity	NPC27887
0.7035	Intermediate Similarity	NPC68619
0.7035	Intermediate Similarity	NPC15764
0.7033	Intermediate Similarity	NPC22928
0.703	Intermediate Similarity	NPC474301
0.7024	Intermediate Similarity	NPC35680
0.7024	Intermediate Similarity	NPC85613
0.7023	Intermediate Similarity	NPC314100
0.7023	Intermediate Similarity	NPC72788
0.7023	Intermediate Similarity	NPC226652
0.7023	Intermediate Similarity	NPC120671
0.7021	Intermediate Similarity	NPC304837
0.7021	Intermediate Similarity	NPC476258
0.702	Intermediate Similarity	NPC301897
0.702	Intermediate Similarity	NPC473900
0.701	Intermediate Similarity	NPC285941
0.7009	Intermediate Similarity	NPC189903
0.7009	Intermediate Similarity	NPC182907
0.7005	Intermediate Similarity	NPC273578
0.7	Intermediate Similarity	NPC139876
0.7	Intermediate Similarity	NPC237579
0.7	Intermediate Similarity	NPC65784
0.7	Intermediate Similarity	NPC167045
0.7	Intermediate Similarity	NPC114120
0.6995	Remote Similarity	NPC118162
0.6995	Remote Similarity	NPC320471
0.6995	Remote Similarity	NPC33256
0.6995	Remote Similarity	NPC24257
0.6995	Remote Similarity	NPC153620
0.6995	Remote Similarity	NPC83049
0.699	Remote Similarity	NPC104353
0.6985	Remote Similarity	NPC477885
0.6985	Remote Similarity	NPC296044
0.6985	Remote Similarity	NPC167098
0.6982	Remote Similarity	NPC477826
0.6982	Remote Similarity	NPC477827
0.698	Remote Similarity	NPC247389
0.698	Remote Similarity	NPC100420
0.6977	Remote Similarity	NPC212163
0.6976	Remote Similarity	NPC477883
0.6971	Remote Similarity	NPC477882
0.6971	Remote Similarity	NPC477880
0.6966	Remote Similarity	NPC108342
0.6966	Remote Similarity	NPC154922
0.6965	Remote Similarity	NPC209411
0.6965	Remote Similarity	NPC109238
0.6965	Remote Similarity	NPC239890
0.6963	Remote Similarity	NPC137920
0.6963	Remote Similarity	NPC86455
0.6963	Remote Similarity	NPC125134
0.6961	Remote Similarity	NPC311912
0.6961	Remote Similarity	NPC79322
0.6961	Remote Similarity	NPC67978
0.6961	Remote Similarity	NPC303581
0.6959	Remote Similarity	NPC119818
0.6959	Remote Similarity	NPC2173
0.6959	Remote Similarity	NPC202771
0.6959	Remote Similarity	NPC328700
0.6954	Remote Similarity	NPC308555
0.6946	Remote Similarity	NPC41689
0.6942	Remote Similarity	NPC283810
0.6942	Remote Similarity	NPC5167
0.6935	Remote Similarity	NPC477380
0.6934	Remote Similarity	NPC313063
0.6934	Remote Similarity	NPC286301
0.6933	Remote Similarity	NPC477828
0.6931	Remote Similarity	NPC24264
0.6931	Remote Similarity	NPC476432
0.6931	Remote Similarity	NPC219341
0.693	Remote Similarity	NPC17677
0.6927	Remote Similarity	NPC88557
0.6923	Remote Similarity	NPC67629
0.6923	Remote Similarity	NPC79736
0.6923	Remote Similarity	NPC477825
0.6919	Remote Similarity	NPC141440

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 NPC227361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	896
0.2-0.3	1112
0.3-0.4	2577
0.4-0.5	2566
0.5-0.6	1374
0.6-0.7	297
0.7-0.8	9
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
0.7401	Intermediate Similarity	NPD6723	Discontinued
0.7302	Intermediate Similarity	NPD6296	Discontinued
0.7237	Intermediate Similarity	NPD8067	Phase 3
0.7172	Intermediate Similarity	NPD710	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6625	Approved
0.7089	Intermediate Similarity	NPD4420	Approved
0.7035	Intermediate Similarity	NPD3252	Approved
0.7023	Intermediate Similarity	NPD4107	Approved
0.7005	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5006	Approved
0.6959	Remote Similarity	NPD5005	Approved
0.6955	Remote Similarity	NPD4859	Phase 1
0.6944	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4482	Phase 3
0.6905	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6232	Discontinued
0.6845	Remote Similarity	NPD5844	Phase 1
0.6835	Remote Similarity	NPD7476	Discontinued
0.6826	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6386	Approved
0.6818	Remote Similarity	NPD6385	Approved
0.6814	Remote Similarity	NPD5242	Approved
0.6798	Remote Similarity	NPD2821	Approved
0.6763	Remote Similarity	NPD1221	Approved
0.6762	Remote Similarity	NPD7546	Discontinued
0.6749	Remote Similarity	NPD3251	Approved
0.6748	Remote Similarity	NPD7473	Discontinued
0.6742	Remote Similarity	NPD7891	Discontinued
0.6726	Remote Similarity	NPD5950	Discontinued
0.6718	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7256	Discontinued
0.67	Remote Similarity	NPD37	Approved
0.6683	Remote Similarity	NPD4965	Approved
0.6683	Remote Similarity	NPD4966	Approved
0.6683	Remote Similarity	NPD4967	Phase 2
0.6682	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5914	Approved
0.6667	Remote Similarity	NPD7922	Phase 1
0.6653	Remote Similarity	NPD8367	Approved
0.6653	Remote Similarity	NPD4846	Phase 2
0.6652	Remote Similarity	NPD3057	Approved
0.6637	Remote Similarity	NPD7783	Phase 2
0.6637	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD8127	Discontinued
0.6623	Remote Similarity	NPD3437	Discontinued
0.662	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1220	Phase 1
0.6618	Remote Similarity	NPD6234	Discontinued
0.6615	Remote Similarity	NPD2438	Suspended
0.6608	Remote Similarity	NPD7827	Phase 1
0.6604	Remote Similarity	NPD2971	Approved
0.6604	Remote Similarity	NPD2968	Approved
0.6595	Remote Similarity	NPD7907	Approved
0.659	Remote Similarity	NPD6213	Phase 3
0.659	Remote Similarity	NPD6212	Phase 3
0.659	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6559	Discontinued
0.6577	Remote Similarity	NPD2972	Approved
0.6577	Remote Similarity	NPD3533	Approved
0.6574	Remote Similarity	NPD7708	Approved
0.6565	Remote Similarity	NPD5980	Discovery
0.6562	Remote Similarity	NPD7999	Approved
0.6561	Remote Similarity	NPD3289	Phase 3
0.6561	Remote Similarity	NPD3290	Approved
0.6558	Remote Similarity	NPD3398	Discontinued
0.6555	Remote Similarity	NPD7177	Discontinued
0.6555	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7199	Phase 2
0.6549	Remote Similarity	NPD8151	Discontinued
0.6546	Remote Similarity	NPD8492	Approved
0.6542	Remote Similarity	NPD3752	Phase 2
0.6538	Remote Similarity	NPD3912	Discontinued
0.6538	Remote Similarity	NPD7278	Phase 2
0.6538	Remote Similarity	NPD7279	Phase 2
0.6538	Remote Similarity	NPD4481	Phase 3
0.653	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD2979	Phase 3
0.6524	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD4505	Phase 1
0.6509	Remote Similarity	NPD7038	Approved
0.6509	Remote Similarity	NPD5519	Discontinued
0.6509	Remote Similarity	NPD7039	Approved
0.6505	Remote Similarity	NPD5494	Approved
0.6502	Remote Similarity	NPD7626	Approved
0.6502	Remote Similarity	NPD7627	Approved
0.6502	Remote Similarity	NPD2491	Approved
0.6502	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD3448	Approved
0.65	Remote Similarity	NPD2973	Approved
0.65	Remote Similarity	NPD2975	Approved
0.65	Remote Similarity	NPD2974	Approved
0.649	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD3818	Discontinued
0.6473	Remote Similarity	NPD2249	Approved
0.6473	Remote Similarity	NPD6457	Approved
0.6473	Remote Similarity	NPD2247	Approved
0.6471	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5071	Phase 2
0.6471	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7803	Approved
0.6471	Remote Similarity	NPD5978	Approved
0.6471	Remote Similarity	NPD5977	Approved
0.6468	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.645	Remote Similarity	NPD5025	Approved
0.6449	Remote Similarity	NPD8312	Approved
0.6449	Remote Similarity	NPD8313	Approved
0.6444	Remote Similarity	NPD7871	Phase 2
0.6444	Remote Similarity	NPD7870	Phase 2
0.6441	Remote Similarity	NPD8285	Discontinued
0.6439	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8404	Phase 2
0.6419	Remote Similarity	NPD5676	Approved
0.6413	Remote Similarity	NPD6780	Approved
0.6413	Remote Similarity	NPD6778	Approved
0.6413	Remote Similarity	NPD4580	Approved
0.6413	Remote Similarity	NPD6779	Approved
0.6413	Remote Similarity	NPD6782	Approved
0.6413	Remote Similarity	NPD6781	Approved
0.6413	Remote Similarity	NPD6776	Approved
0.6413	Remote Similarity	NPD6777	Approved
0.6406	Remote Similarity	NPD1898	Discontinued
0.64	Remote Similarity	NPD7696	Phase 3
0.64	Remote Similarity	NPD7698	Approved
0.64	Remote Similarity	NPD7697	Approved
0.6398	Remote Similarity	NPD7228	Approved
0.6388	Remote Similarity	NPD7583	Approved
0.6386	Remote Similarity	NPD7458	Discontinued
0.6385	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD3450	Approved
0.6384	Remote Similarity	NPD2493	Approved
0.6384	Remote Similarity	NPD3452	Approved
0.6384	Remote Similarity	NPD2494	Approved
0.6379	Remote Similarity	NPD8149	Discontinued
0.6377	Remote Similarity	NPD919	Approved
0.6376	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7874	Approved
0.6376	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4665	Approved
0.6368	Remote Similarity	NPD6874	Approved
0.6368	Remote Similarity	NPD3965	Phase 1
0.6368	Remote Similarity	NPD4111	Phase 1
0.636	Remote Similarity	NPD7585	Approved
0.6356	Remote Similarity	NPD6997	Phase 2
0.6355	Remote Similarity	NPD7685	Pre-registration
0.6347	Remote Similarity	NPD2488	Approved
0.6347	Remote Similarity	NPD2490	Approved
0.6343	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7819	Suspended
0.6336	Remote Similarity	NPD7930	Approved
0.6327	Remote Similarity	NPD7435	Discontinued
0.6326	Remote Similarity	NPD1891	Discontinued
0.6324	Remote Similarity	NPD2672	Discontinued
0.6316	Remote Similarity	NPD2681	Approved
0.6316	Remote Similarity	NPD7584	Approved
0.6316	Remote Similarity	NPD2680	Approved
0.6309	Remote Similarity	NPD7047	Phase 3
0.6308	Remote Similarity	NPD6184	Discontinued
0.6306	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5582	Discontinued
0.6305	Remote Similarity	NPD3226	Approved
0.63	Remote Similarity	NPD4583	Approved
0.63	Remote Similarity	NPD4582	Approved
0.6293	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4356	Discontinued
0.6292	Remote Similarity	NPD7654	Discontinued
0.629	Remote Similarity	NPD7125	Discontinued
0.6288	Remote Similarity	NPD7701	Phase 2
0.6279	Remote Similarity	NPD7240	Approved
0.6277	Remote Similarity	NPD683	Approved
0.6276	Remote Similarity	NPD7223	Discontinued
0.6276	Remote Similarity	NPD7224	Discontinued
0.6275	Remote Similarity	NPD7955	Approved
0.6275	Remote Similarity	NPD3684	Discontinued
0.6275	Remote Similarity	NPD7956	Approved
0.6267	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD8455	Phase 2
0.6256	Remote Similarity	NPD7497	Discontinued
0.6256	Remote Similarity	NPD4004	Approved
0.6256	Remote Similarity	NPD3349	Phase 2
0.6256	Remote Similarity	NPD7693	Approved
0.6256	Remote Similarity	NPD4002	Approved
0.625	Remote Similarity	NPD7225	Discontinued
0.625	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD7048	Phase 3
0.6245	Remote Similarity	NPD5805	Approved
0.6244	Remote Similarity	NPD6873	Phase 2
0.6244	Remote Similarity	NPD7296	Approved
0.6239	Remote Similarity	NPD6321	Discontinued
0.6239	Remote Similarity	NPD7475	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