NPASS Compound

Structure

NPC474159 OpenBabel07101719142D 41 44 0 0 1 0 0 0 0 0999 V2000 0.3474 -2.7521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0646 -2.5260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4483 -2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 4.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 3.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2711 -3.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 -2.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 -2.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 -1.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 -1.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0102 -1.1519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8036 -0.5432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1407 -2.1434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 3.4483 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2711 2.9483 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2711 -1.0517 0.0000 C 0 0 0 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 4.2711 -0.0517 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0032 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 2.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 0.4483 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0032 -1.0517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8692 0.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 3.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -1.0517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8070 1.9483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2711 1.9483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 20 1 0 0 0 0 7 34 1 0 0 0 0 8 34 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 23 2 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 35 1 0 0 0 0 16 24 1 0 0 0 0 16 26 1 0 0 0 0 17 25 1 0 0 0 0 17 27 1 0 0 0 0 18 35 1 0 0 0 0 21 5 1 1 0 0 0 21 22 1 0 0 0 0 21 30 1 0 0 0 0 22 6 1 6 0 0 0 22 41 1 0 0 0 0 23 25 1 0 0 0 0 24 18 1 6 0 0 0 24 34 1 0 0 0 0 25 28 1 0 0 0 0 26 20 1 1 0 0 0 26 34 1 0 0 0 0 27 36 2 0 0 0 0 27 37 1 0 0 0 0 28 31 2 0 0 0 0 28 32 1 0 0 0 0 29 30 2 0 0 0 0 29 31 1 0 0 0 0 29 33 1 0 0 0 0 30 38 1 0 0 0 0 31 41 1 0 0 0 0 32 35 1 0 0 0 0 32 39 2 0 0 0 0 33 35 1 0 0 0 0 33 40 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.31
Volume:	606.067
LogP:	6.795
LogD:	3.796
LogS:	-4.114
# Rotatable Bonds:	9
TPSA:	97.74
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.262
Synthetic Accessibility Score:	5.202
Fsp3:	0.543
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.215
MDCK Permeability:	3.819323319476098e-05
Pgp-inhibitor:	0.237
Pgp-substrate:	0.574
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	96.31551361083984%
Volume Distribution (VD):	0.535
Pgp-substrate:	1.9102669954299927%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.529
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.687
CYP3A4-substrate:	0.885

ADMET: Excretion

Clearance (CL):	11.441
Half-life (T1/2):	0.013

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.846
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.231
Carcinogencity:	0.265
Eye Corrosion:	0.006
Eye Irritation:	0.017
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC474159

Natural Product ID:	NPC474159
*Common Name:**	Isobrasiliensophyllic Acid A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HOTCZQVDDDFXOM-MNEIPBQWSA-N
Standard InCHI:	InChI=1S/C35H44O6/c1-19(2)14-15-35(18-24-16-26(20(3)4)34(24,7)8)32(39)28(25(17-27(36)37)23-12-10-9-11-13-23)31-29(33(35)40)30(38)21(5)22(6)41-31/h9-14,21-22,24-26,38H,3,15-18H2,1-2,4-8H3,(H,36,37)/t21-,22-,24-,25?,26-,35?/m0/s1
SMILES:	OC(=O)CC(C1=C2O[C@@H](C)[C@@H](C(=C2C(=O)C(C1=O)(CC=C(C)C)C[C@@H]1C[C@H](C1(C)C)C(=C)C)O)C)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463087
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002551] Phenylpropanoic acids

*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
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908963]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662094]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104480]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15340243]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	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
IC50	3
MIC	2

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[548496]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[548496]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	1.0	ug.mL-1	PMID[548496]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	16.0	ug.mL-1	PMID[548496]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[548496]

☑ 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 NPC474159 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	240
0.1-0.2	952
0.2-0.3	2444
0.3-0.4	6292
0.4-0.5	11791
0.5-0.6	15924
0.6-0.7	4808
0.7-0.8	232
0.8-0.85	8
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474254
0.9739	High Similarity	NPC474223
0.9739	High Similarity	NPC475827
0.9402	High Similarity	NPC474222
0.9402	High Similarity	NPC475804
0.85	High Similarity	NPC471616
0.8403	Intermediate Similarity	NPC477475
0.8403	Intermediate Similarity	NPC477476
0.8333	Intermediate Similarity	NPC294458
0.8306	Intermediate Similarity	NPC476225
0.822	Intermediate Similarity	NPC40178
0.8136	Intermediate Similarity	NPC47536
0.8136	Intermediate Similarity	NPC20485
0.813	Intermediate Similarity	NPC190298
0.8092	Intermediate Similarity	NPC471832
0.8051	Intermediate Similarity	NPC477251
0.8017	Intermediate Similarity	NPC474689
0.8	Intermediate Similarity	NPC54647
0.7951	Intermediate Similarity	NPC471481
0.7939	Intermediate Similarity	NPC316553
0.7937	Intermediate Similarity	NPC204784
0.791	Intermediate Similarity	NPC15850
0.7886	Intermediate Similarity	NPC234637
0.7886	Intermediate Similarity	NPC130591
0.7857	Intermediate Similarity	NPC64340
0.7836	Intermediate Similarity	NPC209851
0.7786	Intermediate Similarity	NPC328997
0.7786	Intermediate Similarity	NPC294050
0.7778	Intermediate Similarity	NPC61651
0.7769	Intermediate Similarity	NPC140118
0.7769	Intermediate Similarity	NPC12881
0.7769	Intermediate Similarity	NPC325740
0.775	Intermediate Similarity	NPC51174
0.7744	Intermediate Similarity	NPC225103
0.7724	Intermediate Similarity	NPC218855
0.7721	Intermediate Similarity	NPC136994
0.7721	Intermediate Similarity	NPC88255
0.771	Intermediate Similarity	NPC472694
0.771	Intermediate Similarity	NPC472693
0.771	Intermediate Similarity	NPC295664
0.7687	Intermediate Similarity	NPC472388
0.7687	Intermediate Similarity	NPC473443
0.7686	Intermediate Similarity	NPC470007
0.7669	Intermediate Similarity	NPC268607
0.7638	Intermediate Similarity	NPC152812
0.7638	Intermediate Similarity	NPC268930
0.7634	Intermediate Similarity	NPC469742
0.7634	Intermediate Similarity	NPC477362
0.7634	Intermediate Similarity	NPC328107
0.763	Intermediate Similarity	NPC291419
0.763	Intermediate Similarity	NPC60825
0.7626	Intermediate Similarity	NPC118366
0.7623	Intermediate Similarity	NPC469511
0.7615	Intermediate Similarity	NPC475328
0.7607	Intermediate Similarity	NPC476120
0.7607	Intermediate Similarity	NPC179411
0.76	Intermediate Similarity	NPC87069
0.7594	Intermediate Similarity	NPC146239
0.7594	Intermediate Similarity	NPC190849
0.7594	Intermediate Similarity	NPC171007
0.7576	Intermediate Similarity	NPC478108
0.7574	Intermediate Similarity	NPC80599
0.7565	Intermediate Similarity	NPC23453
0.7538	Intermediate Similarity	NPC50872
0.7537	Intermediate Similarity	NPC195224
0.7521	Intermediate Similarity	NPC278228
0.7519	Intermediate Similarity	NPC477366
0.7519	Intermediate Similarity	NPC137416
0.7519	Intermediate Similarity	NPC477363
0.7519	Intermediate Similarity	NPC275576
0.7518	Intermediate Similarity	NPC144257
0.75	Intermediate Similarity	NPC45794
0.75	Intermediate Similarity	NPC472704
0.748	Intermediate Similarity	NPC469636
0.748	Intermediate Similarity	NPC475282
0.748	Intermediate Similarity	NPC260886
0.748	Intermediate Similarity	NPC476476
0.7465	Intermediate Similarity	NPC472801
0.7464	Intermediate Similarity	NPC203486
0.7463	Intermediate Similarity	NPC473423
0.7463	Intermediate Similarity	NPC470753
0.7463	Intermediate Similarity	NPC477365
0.7463	Intermediate Similarity	NPC169913
0.7463	Intermediate Similarity	NPC473220
0.7463	Intermediate Similarity	NPC477357
0.7462	Intermediate Similarity	NPC280827
0.7462	Intermediate Similarity	NPC243059
0.7459	Intermediate Similarity	NPC244933
0.7459	Intermediate Similarity	NPC85560
0.7445	Intermediate Similarity	NPC469499
0.7444	Intermediate Similarity	NPC477369
0.744	Intermediate Similarity	NPC477250
0.7424	Intermediate Similarity	NPC65627
0.7424	Intermediate Similarity	NPC472703
0.7422	Intermediate Similarity	NPC470820
0.7422	Intermediate Similarity	NPC108532
0.7407	Intermediate Similarity	NPC477370
0.7388	Intermediate Similarity	NPC470818
0.7388	Intermediate Similarity	NPC470816
0.7388	Intermediate Similarity	NPC476599
0.7388	Intermediate Similarity	NPC470649
0.7388	Intermediate Similarity	NPC478107
0.7388	Intermediate Similarity	NPC470765
0.7385	Intermediate Similarity	NPC202015
0.7381	Intermediate Similarity	NPC242957
0.7381	Intermediate Similarity	NPC306977
0.7381	Intermediate Similarity	NPC206414
0.7381	Intermediate Similarity	NPC287055
0.7376	Intermediate Similarity	NPC216940
0.7376	Intermediate Similarity	NPC22676
0.7376	Intermediate Similarity	NPC475482
0.7376	Intermediate Similarity	NPC198621
0.7372	Intermediate Similarity	NPC472692
0.7372	Intermediate Similarity	NPC2989
0.7372	Intermediate Similarity	NPC471334
0.7372	Intermediate Similarity	NPC472682
0.7372	Intermediate Similarity	NPC472418
0.7368	Intermediate Similarity	NPC85511
0.7368	Intermediate Similarity	NPC318067
0.7368	Intermediate Similarity	NPC8990
0.7368	Intermediate Similarity	NPC51079
0.7364	Intermediate Similarity	NPC471553
0.7364	Intermediate Similarity	NPC94425
0.7361	Intermediate Similarity	NPC471912
0.7361	Intermediate Similarity	NPC80895
0.736	Intermediate Similarity	NPC477247
0.736	Intermediate Similarity	NPC474157
0.7357	Intermediate Similarity	NPC477874
0.7357	Intermediate Similarity	NPC173569
0.7353	Intermediate Similarity	NPC37968
0.7353	Intermediate Similarity	NPC469930
0.7353	Intermediate Similarity	NPC93632
0.7343	Intermediate Similarity	NPC63737
0.7338	Intermediate Similarity	NPC126516
0.7338	Intermediate Similarity	NPC329913
0.7333	Intermediate Similarity	NPC472706
0.7328	Intermediate Similarity	NPC77273
0.7328	Intermediate Similarity	NPC470585
0.7328	Intermediate Similarity	NPC473243
0.7323	Intermediate Similarity	NPC172525
0.7323	Intermediate Similarity	NPC196075
0.7323	Intermediate Similarity	NPC471721
0.7313	Intermediate Similarity	NPC471758
0.7311	Intermediate Similarity	NPC271475
0.731	Intermediate Similarity	NPC301946
0.731	Intermediate Similarity	NPC277053
0.7305	Intermediate Similarity	NPC184109
0.7305	Intermediate Similarity	NPC249817
0.7299	Intermediate Similarity	NPC25736
0.7299	Intermediate Similarity	NPC475138
0.7299	Intermediate Similarity	NPC272946
0.7299	Intermediate Similarity	NPC49272
0.7297	Intermediate Similarity	NPC264229
0.7297	Intermediate Similarity	NPC306799
0.7297	Intermediate Similarity	NPC46549
0.7297	Intermediate Similarity	NPC101043
0.7295	Intermediate Similarity	NPC19136
0.7293	Intermediate Similarity	NPC12016
0.7293	Intermediate Similarity	NPC223351
0.7292	Intermediate Similarity	NPC477468
0.7286	Intermediate Similarity	NPC194970
0.7279	Intermediate Similarity	NPC115797
0.7279	Intermediate Similarity	NPC51448
0.7273	Intermediate Similarity	NPC476234
0.7273	Intermediate Similarity	NPC242355
0.7266	Intermediate Similarity	NPC210092
0.7266	Intermediate Similarity	NPC215419
0.7266	Intermediate Similarity	NPC228936
0.7266	Intermediate Similarity	NPC469509
0.7266	Intermediate Similarity	NPC221275
0.7259	Intermediate Similarity	NPC45821
0.7246	Intermediate Similarity	NPC17567
0.7246	Intermediate Similarity	NPC289415
0.7246	Intermediate Similarity	NPC319995
0.7246	Intermediate Similarity	NPC472361
0.7244	Intermediate Similarity	NPC93287
0.7244	Intermediate Similarity	NPC272524
0.7239	Intermediate Similarity	NPC472373
0.7239	Intermediate Similarity	NPC138798
0.7236	Intermediate Similarity	NPC321670
0.7234	Intermediate Similarity	NPC472804
0.7234	Intermediate Similarity	NPC472551
0.7234	Intermediate Similarity	NPC472372
0.7234	Intermediate Similarity	NPC472545
0.7234	Intermediate Similarity	NPC472374
0.723	Intermediate Similarity	NPC91730
0.7227	Intermediate Similarity	NPC240042
0.7227	Intermediate Similarity	NPC477767
0.7222	Intermediate Similarity	NPC172311
0.7218	Intermediate Similarity	NPC269923
0.7218	Intermediate Similarity	NPC167323
0.7211	Intermediate Similarity	NPC217918
0.7211	Intermediate Similarity	NPC212808
0.7203	Intermediate Similarity	NPC473440
0.72	Intermediate Similarity	NPC281604
0.7197	Intermediate Similarity	NPC77000
0.7197	Intermediate Similarity	NPC472679
0.7197	Intermediate Similarity	NPC238861
0.7197	Intermediate Similarity	NPC472680
0.7194	Intermediate Similarity	NPC475493

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 NPC474159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	740
0.2-0.3	1495
0.3-0.4	2844
0.4-0.5	2438
0.5-0.6	1192
0.6-0.7	228
0.7-0.8	6
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
0.7881	Intermediate Similarity	NPD5909	Discontinued
0.7742	Intermediate Similarity	NPD6010	Discontinued
0.7565	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6647	Phase 2
0.7381	Intermediate Similarity	NPD6858	Approved
0.7381	Intermediate Similarity	NPD7094	Approved
0.7372	Intermediate Similarity	NPD3268	Approved
0.728	Intermediate Similarity	NPD2067	Discontinued
0.7266	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5048	Discontinued
0.72	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3266	Approved
0.7132	Intermediate Similarity	NPD3267	Approved
0.7132	Intermediate Similarity	NPD2629	Approved
0.7107	Intermediate Similarity	NPD2066	Phase 3
0.7075	Intermediate Similarity	NPD7236	Approved
0.7055	Intermediate Similarity	NPD8166	Discontinued
0.7043	Intermediate Similarity	NPD1282	Approved
0.7007	Intermediate Similarity	NPD2797	Approved
0.6967	Remote Similarity	NPD7798	Approved
0.6957	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6085	Phase 2
0.6953	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1929	Approved
0.6935	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1930	Approved
0.6929	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6637	Approved
0.6905	Remote Similarity	NPD6685	Approved
0.6899	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1088	Approved
0.6889	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.687	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3672	Approved
0.6864	Remote Similarity	NPD3673	Approved
0.6849	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7239	Suspended
0.6822	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4198	Discontinued
0.6809	Remote Similarity	NPD7008	Discontinued
0.6797	Remote Similarity	NPD2182	Approved
0.6794	Remote Similarity	NPD2650	Approved
0.6794	Remote Similarity	NPD2652	Approved
0.678	Remote Similarity	NPD5347	Phase 2
0.678	Remote Similarity	NPD5346	Phase 2
0.6777	Remote Similarity	NPD1693	Approved
0.6761	Remote Similarity	NPD2313	Discontinued
0.6757	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5951	Approved
0.6723	Remote Similarity	NPD1089	Approved
0.6723	Remote Similarity	NPD1086	Approved
0.6723	Remote Similarity	NPD1090	Approved
0.6721	Remote Similarity	NPD1989	Approved
0.6714	Remote Similarity	NPD2798	Approved
0.6713	Remote Similarity	NPD6663	Approved
0.6713	Remote Similarity	NPD7961	Discontinued
0.6712	Remote Similarity	NPD7033	Discontinued
0.6712	Remote Similarity	NPD2799	Discontinued
0.6711	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD5765	Approved
0.6667	Remote Similarity	NPD7741	Discontinued
0.6639	Remote Similarity	NPD800	Approved
0.6624	Remote Similarity	NPD7819	Suspended
0.6621	Remote Similarity	NPD6355	Discontinued
0.662	Remote Similarity	NPD6832	Phase 2
0.6613	Remote Similarity	NPD5926	Approved
0.661	Remote Similarity	NPD4793	Discontinued
0.6603	Remote Similarity	NPD7411	Suspended
0.66	Remote Similarity	NPD4628	Phase 3
0.6599	Remote Similarity	NPD7305	Phase 1
0.6597	Remote Similarity	NPD8032	Phase 2
0.6596	Remote Similarity	NPD5647	Approved
0.6594	Remote Similarity	NPD2610	Approved
0.6594	Remote Similarity	NPD2608	Approved
0.6594	Remote Similarity	NPD4216	Approved
0.6594	Remote Similarity	NPD4215	Approved
0.6594	Remote Similarity	NPD2612	Approved
0.6594	Remote Similarity	NPD4217	Approved
0.6594	Remote Similarity	NPD3131	Approved
0.6594	Remote Similarity	NPD4218	Approved
0.6594	Remote Similarity	NPD2611	Approved
0.6594	Remote Similarity	NPD3132	Approved
0.6594	Remote Similarity	NPD6287	Discontinued
0.6594	Remote Similarity	NPD2609	Approved
0.6581	Remote Similarity	NPD7458	Discontinued
0.6581	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.656	Remote Similarity	NPD1238	Approved
0.6547	Remote Similarity	NPD3972	Approved
0.6529	Remote Similarity	NPD8434	Phase 2
0.6528	Remote Similarity	NPD6798	Discontinued
0.6528	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD9493	Approved
0.6515	Remote Similarity	NPD6912	Phase 3
0.651	Remote Similarity	NPD2346	Discontinued
0.6503	Remote Similarity	NPD7055	Discontinued
0.6494	Remote Similarity	NPD6273	Approved
0.6485	Remote Similarity	NPD7799	Discontinued
0.6484	Remote Similarity	NPD1237	Approved
0.6484	Remote Similarity	NPD164	Approved
0.6483	Remote Similarity	NPD7714	Approved
0.6483	Remote Similarity	NPD7715	Approved
0.6483	Remote Similarity	NPD6233	Phase 2
0.648	Remote Similarity	NPD9495	Approved
0.6475	Remote Similarity	NPD4807	Approved
0.6475	Remote Similarity	NPD4806	Approved
0.6471	Remote Similarity	NPD1087	Approved
0.6463	Remote Similarity	NPD6651	Approved
0.6457	Remote Similarity	NPD1932	Approved
0.6454	Remote Similarity	NPD3225	Approved
0.6449	Remote Similarity	NPD2932	Approved
0.6449	Remote Similarity	NPD5306	Approved
0.6449	Remote Similarity	NPD5305	Approved
0.6444	Remote Similarity	NPD3317	Approved
0.6443	Remote Similarity	NPD2935	Discontinued
0.6438	Remote Similarity	NPD7057	Phase 3
0.6438	Remote Similarity	NPD7058	Phase 2
0.6433	Remote Similarity	NPD6599	Discontinued
0.6429	Remote Similarity	NPD8368	Discontinued
0.6429	Remote Similarity	NPD9717	Approved
0.6429	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1608	Approved
0.6423	Remote Similarity	NPD1894	Discontinued
0.6423	Remote Similarity	NPD9545	Approved
0.6418	Remote Similarity	NPD1241	Discontinued
0.6412	Remote Similarity	NPD2329	Discontinued
0.641	Remote Similarity	NPD9491	Approved
0.6408	Remote Similarity	NPD6362	Approved
0.64	Remote Similarity	NPD6005	Phase 3
0.64	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1566	Phase 3
0.64	Remote Similarity	NPD1565	Approved
0.64	Remote Similarity	NPD6004	Phase 3
0.64	Remote Similarity	NPD1564	Approved
0.64	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6002	Phase 3
0.64	Remote Similarity	NPD3495	Discontinued
0.6398	Remote Similarity	NPD7075	Discontinued
0.6397	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD1239	Approved
0.6393	Remote Similarity	NPD6411	Approved
0.6392	Remote Similarity	NPD5889	Approved
0.6392	Remote Similarity	NPD5890	Approved
0.6389	Remote Similarity	NPD2613	Approved
0.6382	Remote Similarity	NPD4110	Phase 3
0.6382	Remote Similarity	NPD7003	Approved
0.6382	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD226	Approved
0.6377	Remote Similarity	NPD5585	Approved
0.6376	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6049	Phase 2
0.637	Remote Similarity	NPD7713	Phase 3
0.6369	Remote Similarity	NPD3226	Approved
0.6364	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6801	Discontinued
0.635	Remote Similarity	NPD7610	Discontinued
0.6345	Remote Similarity	NPD7095	Approved
0.6343	Remote Similarity	NPD2607	Approved
0.6341	Remote Similarity	NPD7631	Approved
0.6338	Remote Similarity	NPD1283	Approved
0.6335	Remote Similarity	NPD7768	Phase 2
0.6333	Remote Similarity	NPD2796	Approved
0.6331	Remote Similarity	NPD1778	Approved
0.6331	Remote Similarity	NPD3019	Approved
0.6327	Remote Similarity	NPD4140	Approved
0.6323	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8407	Phase 2
0.6309	Remote Similarity	NPD7097	Phase 1
0.6309	Remote Similarity	NPD2567	Approved
0.6309	Remote Similarity	NPD2569	Approved
0.6304	Remote Similarity	NPD7009	Phase 2
0.6299	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1203	Approved
0.6291	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3847	Discontinued
0.6286	Remote Similarity	NPD4106	Approved
0.6286	Remote Similarity	NPD4136	Approved
0.6286	Remote Similarity	NPD4135	Approved
0.6284	Remote Similarity	NPD5124	Phase 1
0.6284	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.628	Remote Similarity	NPD8127	Discontinued
0.6277	Remote Similarity	NPD4574	Approved
0.6277	Remote Similarity	NPD4576	Approved
0.6275	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3750	Approved
0.6269	Remote Similarity	NPD969	Suspended

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