NPASS Compound

Structure

NPC94487 OpenBabel07101719522D 27 28 0 0 1 0 0 0 0 0999 V2000 -2.4049 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0592 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1932 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9253 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6728 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7913 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1214 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6573 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2554 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1214 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5233 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3894 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2554 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3894 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.2955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5768 -0.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 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 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 13 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 20 1 0 0 0 0 15 20 2 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 1 1 1 0 0 0 22 26 1 0 0 0 0 23 2 1 6 0 0 0 23 27 1 0 0 0 0 26 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.26
Volume:	413.866
LogP:	6.36
LogD:	3.477
LogS:	-5.605
# Rotatable Bonds:	13
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	3.304
Fsp3:	0.696
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.99
MDCK Permeability:	2.8003001716569997e-05
Pgp-inhibitor:	0.886
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.119
Plasma Protein Binding (PPB):	97.84052276611328%
Volume Distribution (VD):	0.693
Pgp-substrate:	0.48756110668182373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.399
CYP2C19-inhibitor:	0.377
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.27
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.869
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	5.222
Half-life (T1/2):	0.588

ADMET: Toxicity

hERG Blockers:	0.151
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.17
Skin Sensitization:	0.956
Carcinogencity:	0.119
Eye Corrosion:	0.206
Eye Irritation:	0.507
Respiratory Toxicity:	0.853

Download Data

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

Natural Product: NPC94487

Natural Product ID:	NPC94487
*Common Name:**	Andavadoic Acid
IUPAC Name:	2-[(3R,5S)-3,5-dimethyl-5-(10-phenyldecyl)dioxolan-3-yl]acetic acid
Synonyms:	Andavadoic Acid
Standard InCHIKey:	LSOSWFXHGHKMMC-GOTSBHOMSA-N
Standard InCHI:	InChI=1S/C23H36O4/c1-22(19-23(2,27-26-22)18-21(24)25)17-13-8-6-4-3-5-7-10-14-20-15-11-9-12-16-20/h9,11-12,15-16H,3-8,10,13-14,17-19H2,1-2H3,(H,24,25)/t22-,23-/m0/s1
SMILES:	C[C@]1(CCCCCCCCCCc2ccccc2)C[C@](C)(CC(=O)O)OO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464754
PubChem CID:	9969798
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted 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
NPO33436	plakortis aff simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762807]

☑ 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
GI50	13
Others	26

Activity Type	# Activity
Cell Line	33
NON-MOLECULAR	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50	=	497.0	nM	PMID[474045]
NPT111	Cell Line	K562	Homo sapiens	TGI	=	1010.0	nM	PMID[474045]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	2070.0	nM	PMID[474045]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	714.0	nM	PMID[474045]
NPT81	Cell Line	A549	Homo sapiens	TGI	=	1290.0	nM	PMID[474045]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	2330.0	nM	PMID[474045]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	=	698.0	nM	PMID[474045]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	TGI	=	1140.0	nM	PMID[474045]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	LC50	=	1860.0	nM	PMID[474045]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	643.0	nM	PMID[474045]
NPT139	Cell Line	HT-29	Homo sapiens	TGI	=	1130.0	nM	PMID[474045]
NPT139	Cell Line	HT-29	Homo sapiens	LC50	=	1980.0	nM	PMID[474045]
NPT114	Cell Line	LoVo	Homo sapiens	GI50	=	635.0	nM	PMID[474045]
NPT114	Cell Line	LoVo	Homo sapiens	TGI	=	1210.0	nM	PMID[474045]
NPT114	Cell Line	LoVo	Homo sapiens	LC50	=	2310.0	nM	PMID[474045]
NPT114	Cell Line	LoVo	Homo sapiens	GI50	=	539.0	nM	PMID[474045]
NPT114	Cell Line	LoVo	Homo sapiens	TGI	=	951.0	nM	PMID[474045]
NPT114	Cell Line	LoVo	Homo sapiens	LC50	=	1680.0	nM	PMID[474045]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	627.0	nM	PMID[474045]
NPT90	Cell Line	DU-145	Homo sapiens	TGI	=	991.0	nM	PMID[474045]
NPT90	Cell Line	DU-145	Homo sapiens	LC50	=	1560.0	nM	PMID[474045]
NPT858	Cell Line	LNCaP	Homo sapiens	GI50	=	478.0	nM	PMID[474045]
NPT858	Cell Line	LNCaP	Homo sapiens	TGI	=	863.0	nM	PMID[474045]
NPT858	Cell Line	LNCaP	Homo sapiens	LC50	=	1560.0	nM	PMID[474045]
NPT134	Cell Line	SK-BR-3	Homo sapiens	GI50	=	914.0	nM	PMID[474045]
NPT134	Cell Line	SK-BR-3	Homo sapiens	TGI	=	1690.0	nM	PMID[474045]
NPT134	Cell Line	SK-BR-3	Homo sapiens	LC50	=	2660.0	nM	PMID[474045]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	=	698.0	nM	PMID[474045]
NPT146	Cell Line	SK-OV-3	Homo sapiens	TGI	=	1120.0	nM	PMID[474045]
NPT146	Cell Line	SK-OV-3	Homo sapiens	LC50	=	1810.0	nM	PMID[474045]
NPT461	Cell Line	PANC-1	Homo sapiens	GI50	=	526.0	nM	PMID[474045]
NPT461	Cell Line	PANC-1	Homo sapiens	TGI	=	961.0	nM	PMID[474045]
NPT461	Cell Line	PANC-1	Homo sapiens	LC50	=	1750.0	nM	PMID[474045]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	102.0	nM	PMID[474045]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	261.0	nM	PMID[474045]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	1830.0	nM	PMID[474045]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	133.0	nM	PMID[474045]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	390.0	nM	PMID[474045]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	1340.0	nM	PMID[474045]

☑ 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 NPC94487 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	174
0.1-0.2	771
0.2-0.3	2244
0.3-0.4	8009
0.4-0.5	16951
0.5-0.6	12764
0.6-0.7	1688
0.7-0.8	82
0.8-0.85	6
0.85-0.9	1
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC474820
0.9894	High Similarity	NPC475978
0.9278	High Similarity	NPC474112
0.8969	High Similarity	NPC271475
0.8866	High Similarity	NPC477767
0.828	Intermediate Similarity	NPC44830
0.8247	Intermediate Similarity	NPC84288
0.819	Intermediate Similarity	NPC329705
0.819	Intermediate Similarity	NPC474111
0.8173	Intermediate Similarity	NPC19136
0.7957	Intermediate Similarity	NPC127343
0.7857	Intermediate Similarity	NPC329064
0.7755	Intermediate Similarity	NPC322387
0.7732	Intermediate Similarity	NPC95965
0.7714	Intermediate Similarity	NPC225079
0.7714	Intermediate Similarity	NPC264728
0.7708	Intermediate Similarity	NPC285773
0.77	Intermediate Similarity	NPC86670
0.77	Intermediate Similarity	NPC70940
0.77	Intermediate Similarity	NPC274455
0.7699	Intermediate Similarity	NPC210531
0.7685	Intermediate Similarity	NPC244933
0.7685	Intermediate Similarity	NPC85560
0.7679	Intermediate Similarity	NPC294458
0.7634	Intermediate Similarity	NPC120776
0.7634	Intermediate Similarity	NPC240170
0.7624	Intermediate Similarity	NPC187725
0.7624	Intermediate Similarity	NPC141607
0.7624	Intermediate Similarity	NPC86987
0.7619	Intermediate Similarity	NPC54647
0.7589	Intermediate Similarity	NPC477475
0.7589	Intermediate Similarity	NPC477476
0.7526	Intermediate Similarity	NPC477770
0.7524	Intermediate Similarity	NPC120393
0.75	Intermediate Similarity	NPC477704
0.75	Intermediate Similarity	NPC477693
0.7455	Intermediate Similarity	NPC20485
0.7431	Intermediate Similarity	NPC321670
0.7429	Intermediate Similarity	NPC469890
0.7429	Intermediate Similarity	NPC469892
0.7429	Intermediate Similarity	NPC469891
0.7426	Intermediate Similarity	NPC231591
0.7417	Intermediate Similarity	NPC138798
0.7404	Intermediate Similarity	NPC206764
0.7383	Intermediate Similarity	NPC128248
0.7383	Intermediate Similarity	NPC133809
0.7383	Intermediate Similarity	NPC136810
0.7383	Intermediate Similarity	NPC158623
0.7364	Intermediate Similarity	NPC25385
0.7364	Intermediate Similarity	NPC193640
0.7364	Intermediate Similarity	NPC475905
0.7347	Intermediate Similarity	NPC288903
0.7339	Intermediate Similarity	NPC329282
0.7333	Intermediate Similarity	NPC108286
0.7333	Intermediate Similarity	NPC261947
0.7333	Intermediate Similarity	NPC472703
0.7333	Intermediate Similarity	NPC469893
0.7295	Intermediate Similarity	NPC79608
0.7295	Intermediate Similarity	NPC476033
0.729	Intermediate Similarity	NPC7435
0.7282	Intermediate Similarity	NPC317645
0.7273	Intermediate Similarity	NPC472704
0.7273	Intermediate Similarity	NPC474307
0.7273	Intermediate Similarity	NPC236981
0.7265	Intermediate Similarity	NPC94425
0.7248	Intermediate Similarity	NPC329556
0.7238	Intermediate Similarity	NPC172925
0.7232	Intermediate Similarity	NPC475006
0.7207	Intermediate Similarity	NPC317592
0.72	Intermediate Similarity	NPC294134
0.7193	Intermediate Similarity	NPC218855
0.719	Intermediate Similarity	NPC469927
0.7177	Intermediate Similarity	NPC268607
0.7156	Intermediate Similarity	NPC25458
0.713	Intermediate Similarity	NPC217621
0.7115	Intermediate Similarity	NPC110704
0.7107	Intermediate Similarity	NPC293831
0.7107	Intermediate Similarity	NPC369
0.7105	Intermediate Similarity	NPC95126
0.7105	Intermediate Similarity	NPC475002
0.7103	Intermediate Similarity	NPC226041
0.7097	Intermediate Similarity	NPC146239
0.7097	Intermediate Similarity	NPC472706
0.7097	Intermediate Similarity	NPC473751
0.7094	Intermediate Similarity	NPC9274
0.7091	Intermediate Similarity	NPC247976
0.7087	Intermediate Similarity	NPC9822
0.7083	Intermediate Similarity	NPC475827
0.7083	Intermediate Similarity	NPC474222
0.7083	Intermediate Similarity	NPC475804
0.7083	Intermediate Similarity	NPC474223
0.7083	Intermediate Similarity	NPC145898
0.708	Intermediate Similarity	NPC40178
0.7073	Intermediate Similarity	NPC317163
0.7073	Intermediate Similarity	NPC478108
0.7073	Intermediate Similarity	NPC246166
0.7071	Intermediate Similarity	NPC323103
0.7069	Intermediate Similarity	NPC172525
0.7069	Intermediate Similarity	NPC87069
0.7069	Intermediate Similarity	NPC234637
0.7069	Intermediate Similarity	NPC130591
0.7069	Intermediate Similarity	NPC162113
0.7069	Intermediate Similarity	NPC62546
0.7054	Intermediate Similarity	NPC142326
0.7054	Intermediate Similarity	NPC100767
0.7054	Intermediate Similarity	NPC37914
0.7054	Intermediate Similarity	NPC94751
0.7053	Intermediate Similarity	NPC189371
0.7048	Intermediate Similarity	NPC323164
0.7037	Intermediate Similarity	NPC179411
0.703	Intermediate Similarity	NPC475710
0.7016	Intermediate Similarity	NPC477366
0.7009	Intermediate Similarity	NPC221870
0.7009	Intermediate Similarity	NPC29607
0.7008	Intermediate Similarity	NPC17840
0.7008	Intermediate Similarity	NPC471334
0.7008	Intermediate Similarity	NPC247477
0.7	Intermediate Similarity	NPC304873
0.7	Intermediate Similarity	NPC284477
0.7	Intermediate Similarity	NPC270507
0.6992	Remote Similarity	NPC477362
0.6991	Remote Similarity	NPC47536
0.6991	Remote Similarity	NPC249811
0.6983	Remote Similarity	NPC93287
0.6983	Remote Similarity	NPC471481
0.6981	Remote Similarity	NPC34243
0.6975	Remote Similarity	NPC471553
0.6972	Remote Similarity	NPC476042
0.6972	Remote Similarity	NPC221825
0.6972	Remote Similarity	NPC228435
0.696	Remote Similarity	NPC477357
0.696	Remote Similarity	NPC477365
0.6953	Remote Similarity	NPC469499
0.6949	Remote Similarity	NPC471616
0.6949	Remote Similarity	NPC188010
0.6947	Remote Similarity	NPC475955
0.6947	Remote Similarity	NPC474726
0.6944	Remote Similarity	NPC240042
0.6944	Remote Similarity	NPC324569
0.6944	Remote Similarity	NPC253423
0.6942	Remote Similarity	NPC234337
0.6942	Remote Similarity	NPC133389
0.6942	Remote Similarity	NPC478015
0.6942	Remote Similarity	NPC478014
0.6942	Remote Similarity	NPC183339
0.6942	Remote Similarity	NPC478016
0.6939	Remote Similarity	NPC272260
0.6937	Remote Similarity	NPC471317
0.6931	Remote Similarity	NPC267704
0.693	Remote Similarity	NPC31274
0.693	Remote Similarity	NPC469511
0.6917	Remote Similarity	NPC472698
0.6917	Remote Similarity	NPC474890
0.6917	Remote Similarity	NPC161943
0.6917	Remote Similarity	NPC273282
0.6917	Remote Similarity	NPC472697
0.6915	Remote Similarity	NPC155429
0.6915	Remote Similarity	NPC74458
0.6911	Remote Similarity	NPC474254
0.6911	Remote Similarity	NPC474159
0.6907	Remote Similarity	NPC9796
0.6905	Remote Similarity	NPC477370
0.6903	Remote Similarity	NPC477251
0.69	Remote Similarity	NPC121478
0.69	Remote Similarity	NPC103387
0.69	Remote Similarity	NPC73637
0.6899	Remote Similarity	NPC144257
0.6897	Remote Similarity	NPC292834
0.6891	Remote Similarity	NPC83718
0.6891	Remote Similarity	NPC212891
0.6885	Remote Similarity	NPC159760
0.6885	Remote Similarity	NPC178395
0.6885	Remote Similarity	NPC292665
0.6885	Remote Similarity	NPC272454
0.6885	Remote Similarity	NPC301987
0.6885	Remote Similarity	NPC115188
0.6885	Remote Similarity	NPC222876
0.6885	Remote Similarity	NPC244994
0.6885	Remote Similarity	NPC179092
0.6885	Remote Similarity	NPC26433
0.6885	Remote Similarity	NPC35856
0.6881	Remote Similarity	NPC229242
0.6881	Remote Similarity	NPC175852
0.6881	Remote Similarity	NPC210529
0.6881	Remote Similarity	NPC329387
0.6881	Remote Similarity	NPC317280
0.6881	Remote Similarity	NPC476120
0.6881	Remote Similarity	NPC145052
0.6881	Remote Similarity	NPC160548
0.688	Remote Similarity	NPC470816
0.688	Remote Similarity	NPC477363
0.6869	Remote Similarity	NPC121800
0.6864	Remote Similarity	NPC469509
0.6864	Remote Similarity	NPC221275
0.6864	Remote Similarity	NPC217111
0.686	Remote Similarity	NPC202015
0.6852	Remote Similarity	NPC61944
0.685	Remote Similarity	NPC69496
0.685	Remote Similarity	NPC37968
0.6846	Remote Similarity	NPC88255

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 NPC94487 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	691
0.2-0.3	1508
0.3-0.4	3189
0.4-0.5	2485
0.5-0.6	894
0.6-0.7	195
0.7-0.8	28
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
0.8144	Intermediate Similarity	NPD5347	Phase 2
0.8144	Intermediate Similarity	NPD5346	Phase 2
0.8125	Intermediate Similarity	NPD4793	Discontinued
0.8095	Intermediate Similarity	NPD5048	Discontinued
0.8065	Intermediate Similarity	NPD226	Approved
0.8	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5765	Approved
0.785	Intermediate Similarity	NPD6685	Approved
0.7778	Intermediate Similarity	NPD800	Approved
0.7745	Intermediate Similarity	NPD1693	Approved
0.7742	Intermediate Similarity	NPD225	Approved
0.7742	Intermediate Similarity	NPD227	Approved
0.7708	Intermediate Similarity	NPD9491	Approved
0.77	Intermediate Similarity	NPD1086	Approved
0.77	Intermediate Similarity	NPD1089	Approved
0.77	Intermediate Similarity	NPD1090	Approved
0.7549	Intermediate Similarity	NPD1088	Approved
0.7453	Intermediate Similarity	NPD2066	Phase 3
0.74	Intermediate Similarity	NPD1087	Approved
0.7368	Intermediate Similarity	NPD2650	Approved
0.7368	Intermediate Similarity	NPD2652	Approved
0.7353	Intermediate Similarity	NPD3672	Approved
0.7353	Intermediate Similarity	NPD3673	Approved
0.7345	Intermediate Similarity	NPD6912	Phase 3
0.7302	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD9490	Approved
0.729	Intermediate Similarity	NPD7798	Approved
0.7282	Intermediate Similarity	NPD1239	Approved
0.7248	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1929	Approved
0.7248	Intermediate Similarity	NPD1930	Approved
0.7248	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6647	Phase 2
0.7238	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD467	Phase 1
0.717	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD1932	Approved
0.713	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1566	Phase 3
0.7103	Intermediate Similarity	NPD1565	Approved
0.7103	Intermediate Similarity	NPD1564	Approved
0.708	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6010	Discontinued
0.7027	Intermediate Similarity	NPD5909	Discontinued
0.7018	Intermediate Similarity	NPD5278	Discontinued
0.7018	Intermediate Similarity	NPD1317	Discontinued
0.7009	Intermediate Similarity	NPD1989	Approved
0.693	Remote Similarity	NPD2329	Discontinued
0.6881	Remote Similarity	NPD9495	Approved
0.6881	Remote Similarity	NPD253	Approved
0.685	Remote Similarity	NPD2613	Approved
0.6829	Remote Similarity	NPD4216	Approved
0.6829	Remote Similarity	NPD4218	Approved
0.6829	Remote Similarity	NPD2609	Approved
0.6829	Remote Similarity	NPD4215	Approved
0.6829	Remote Similarity	NPD4217	Approved
0.6829	Remote Similarity	NPD2612	Approved
0.6829	Remote Similarity	NPD3131	Approved
0.6829	Remote Similarity	NPD2610	Approved
0.6829	Remote Similarity	NPD3132	Approved
0.6829	Remote Similarity	NPD2611	Approved
0.6829	Remote Similarity	NPD2608	Approved
0.6822	Remote Similarity	NPD1066	Discontinued
0.6822	Remote Similarity	NPD1563	Approved
0.681	Remote Similarity	NPD3644	Approved
0.681	Remote Similarity	NPD3642	Approved
0.681	Remote Similarity	NPD3643	Approved
0.681	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD9566	Approved
0.6724	Remote Similarity	NPD2067	Discontinued
0.6723	Remote Similarity	NPD2629	Approved
0.6699	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD9256	Approved
0.6698	Remote Similarity	NPD9258	Approved
0.6695	Remote Similarity	NPD7094	Approved
0.6695	Remote Similarity	NPD6858	Approved
0.6693	Remote Similarity	NPD6085	Phase 2
0.6693	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2570	Approved
0.6692	Remote Similarity	NPD3087	Approved
0.6692	Remote Similarity	NPD3088	Approved
0.6692	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2566	Approved
0.6692	Remote Similarity	NPD4746	Phase 3
0.6692	Remote Similarity	NPD3614	Approved
0.6692	Remote Similarity	NPD4745	Approved
0.6692	Remote Similarity	NPD3616	Approved
0.6692	Remote Similarity	NPD3615	Approved
0.6692	Remote Similarity	NPD3090	Approved
0.6692	Remote Similarity	NPD2571	Approved
0.6692	Remote Similarity	NPD2574	Discontinued
0.6692	Remote Similarity	NPD3089	Approved
0.6692	Remote Similarity	NPD2573	Approved
0.6667	Remote Similarity	NPD3317	Approved
0.6667	Remote Similarity	NPD1202	Approved
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3598	Phase 3
0.6591	Remote Similarity	NPD4685	Phase 3
0.6591	Remote Similarity	NPD4686	Approved
0.6591	Remote Similarity	NPD4684	Phase 3
0.6583	Remote Similarity	NPD5951	Approved
0.6583	Remote Similarity	NPD1711	Phase 2
0.6583	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD1246	Approved
0.6567	Remote Similarity	NPD7033	Discontinued
0.6562	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6065	Approved
0.6557	Remote Similarity	NPD7610	Discontinued
0.6552	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1018	Approved
0.6522	Remote Similarity	NPD1040	Phase 2
0.6514	Remote Similarity	NPD3718	Approved
0.6514	Remote Similarity	NPD3719	Approved
0.6508	Remote Similarity	NPD6637	Approved
0.6508	Remote Similarity	NPD1608	Approved
0.6505	Remote Similarity	NPD3971	Phase 1
0.6504	Remote Similarity	NPD3798	Phase 3
0.65	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7609	Phase 3
0.6476	Remote Similarity	NPD9259	Approved
0.6476	Remote Similarity	NPD9257	Approved
0.6475	Remote Similarity	NPD3797	Approved
0.6452	Remote Similarity	NPD4102	Approved
0.6452	Remote Similarity	NPD4105	Approved
0.6441	Remote Similarity	NPD4233	Approved
0.6441	Remote Similarity	NPD4234	Approved
0.6429	Remote Similarity	NPD4807	Approved
0.6429	Remote Similarity	NPD4806	Approved
0.6422	Remote Similarity	NPD7631	Approved
0.641	Remote Similarity	NPD9267	Approved
0.641	Remote Similarity	NPD9264	Approved
0.641	Remote Similarity	NPD9263	Approved
0.64	Remote Similarity	NPD5306	Approved
0.64	Remote Similarity	NPD5305	Approved
0.6393	Remote Similarity	NPD4198	Discontinued
0.6383	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD3072	Approved
0.6378	Remote Similarity	NPD3073	Approved
0.6378	Remote Similarity	NPD3071	Approved
0.6373	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD1067	Discontinued
0.6371	Remote Similarity	NPD4479	Discontinued
0.6371	Remote Similarity	NPD7009	Phase 2
0.6371	Remote Similarity	NPD9545	Approved
0.6364	Remote Similarity	NPD9716	Approved
0.6364	Remote Similarity	NPD3764	Approved
0.6356	Remote Similarity	NPD2182	Approved
0.6356	Remote Similarity	NPD74	Approved
0.6356	Remote Similarity	NPD9266	Approved
0.6349	Remote Similarity	NPD4135	Approved
0.6349	Remote Similarity	NPD4106	Approved
0.6349	Remote Similarity	NPD4136	Approved
0.6341	Remote Similarity	NPD9493	Approved
0.6331	Remote Similarity	NPD2575	Approved
0.632	Remote Similarity	NPD1245	Approved
0.632	Remote Similarity	NPD5981	Approved
0.6316	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7961	Discontinued
0.6311	Remote Similarity	NPD747	Discontinued
0.6311	Remote Similarity	NPD942	Approved
0.6311	Remote Similarity	NPD4766	Approved
0.6299	Remote Similarity	NPD4761	Approved
0.6299	Remote Similarity	NPD4762	Approved
0.6299	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD1237	Approved
0.6293	Remote Similarity	NPD164	Approved
0.629	Remote Similarity	NPD1758	Phase 1
0.6288	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5277	Phase 2
0.6277	Remote Similarity	NPD7137	Phase 2
0.6273	Remote Similarity	NPD5779	Approved
0.6273	Remote Similarity	NPD5778	Approved
0.627	Remote Similarity	NPD4199	Phase 3
0.627	Remote Similarity	NPD17	Approved
0.627	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.627	Remote Similarity	NPD2345	Approved
0.626	Remote Similarity	NPD3661	Approved
0.626	Remote Similarity	NPD5759	Approved
0.626	Remote Similarity	NPD3662	Phase 3
0.626	Remote Similarity	NPD255	Approved
0.626	Remote Similarity	NPD256	Approved
0.626	Remote Similarity	NPD5204	Approved
0.626	Remote Similarity	NPD1348	Approved
0.626	Remote Similarity	NPD3664	Approved
0.626	Remote Similarity	NPD3663	Approved
0.625	Remote Similarity	NPD188	Approved
0.625	Remote Similarity	NPD189	Phase 3
0.624	Remote Similarity	NPD2218	Phase 2
0.624	Remote Similarity	NPD2617	Discontinued
0.624	Remote Similarity	NPD1759	Phase 1
0.624	Remote Similarity	NPD2217	Approved
0.6232	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6004	Phase 3
0.6232	Remote Similarity	NPD6002	Phase 3
0.6232	Remote Similarity	NPD6005	Phase 3
0.6218	Remote Similarity	NPD476	Approved
0.621	Remote Similarity	NPD5162	Approved
0.6207	Remote Similarity	NPD9261	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