NPASS Compound

Structure

CID97188 OpenBabel06191715432D 34 36 0 0 1 0 0 0 0 0999 V2000 5.4153 1.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2079 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7107 -3.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2813 -0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5578 0.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2984 -0.0131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2813 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 -3.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 -2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -2.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4483 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 0.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4153 0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5493 -0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1180 0.2806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4153 -1.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4483 -3.3698 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5493 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4538 -3.2653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4153 -2.9781 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5529 -4.3644 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7079 -0.1121 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.8304 -0.4212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0813 1.5522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6617 -4.2435 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 1 16 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 9 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 19 2 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 19 26 1 0 0 0 0 20 31 1 0 0 0 0 21 26 1 6 0 0 0 21 28 1 0 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 25 1 1 0 0 0 23 34 1 0 0 0 0 24 32 2 0 0 0 0 24 34 1 0 0 0 0 25 30 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	662.02
Volume:	529.708
LogP:	7.073
LogD:	4.636
LogS:	-4.97
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	6.0
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-4.662
MDCK Permeability:	2.0949155441485345e-05
Pgp-inhibitor:	0.942
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.234
30% Bioavailability (F30%):	0.446

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211
Plasma Protein Binding (PPB):	100.07244110107422%
Volume Distribution (VD):	1.849
Pgp-substrate:	2.56817889213562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.262
CYP1A2-substrate:	0.184
CYP2C19-inhibitor:	0.909
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.962
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.128
CYP2D6-substrate:	0.413
CYP3A4-inhibitor:	0.875
CYP3A4-substrate:	0.861

ADMET: Excretion

Clearance (CL):	8.621
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.752
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.554
Maximum Recommended Daily Dose:	0.88
Skin Sensitization:	0.656
Carcinogencity:	0.458
Eye Corrosion:	0.515
Eye Irritation:	0.445
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC97188

Natural Product ID:	NPC97188
*Common Name:**	SKIHYPQTROYIIT-VHXXJFIISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SKIHYPQTROYIIT-VHXXJFIISA-N
Standard InCHI:	InChI=1S/C27H37Br3O4/c1-16-6-9-21(28)26(4)12-10-22(29)27(5,33)13-11-23(25(2,3)30)34-24(32)17-7-8-20(31)18(14-17)15-19(16)26/h7-8,14,21-23,31,33H,6,9-13,15H2,1-5H3/t21-,22+,23-,26-,27-/m0/s1
SMILES:	O=C1O[C@@H](CC[C@](C)(O)[C@H](Br)CC[C@]2(C(=C(C)CC[C@@H]2Br)Cc2cc1ccc2O)C)C(Br)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1257967
PubChem CID:	21778345
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16268553]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[16724831]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715978]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[20141173]
NPO33001	macroalgae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20801038]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407005]
NPO8966	Callophycus serratus	Species	Solieriaceae	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	4
MIC	4
Others	27

Activity Type	# Activity
Cell Line	1
Organism	20
Others	4
Subcellular	6
Tissue	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6200.0	nM	PMID[485072]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	700.0	nM	PMID[485070]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5900.0	nM	PMID[485070]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	5900.0	nM	PMID[485070]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	11000.0	nM	PMID[485070]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	49000.0	nM	PMID[485070]
NPT433	Subcellular	Liver microsomes	Homo sapiens	T1/2	=	6.6	hr	PMID[485071]
NPT433	Subcellular	Liver microsomes	Homo sapiens	CL	=	1.6	mL.min-1.kg-1	PMID[485071]
NPT433	Subcellular	Liver microsomes	Homo sapiens	Stability	=	15.3	%	PMID[485071]
NPT433	Subcellular	Liver microsomes	Homo sapiens	T1/2	=	14.0	hr	PMID[485071]
NPT433	Subcellular	Liver microsomes	Homo sapiens	CLH	=	0.72	ml/mg/kg	PMID[485071]
NPT433	Subcellular	Liver microsomes	Homo sapiens	Drug metabolism	=	61.0	%	PMID[485071]
NPT27	Others	Unspecified		T1/2	=	9.5	hr	PMID[485071]
NPT27	Others	Unspecified		CL	=	1.1	mL.min-1.kg-1	PMID[485071]
NPT27	Others	Unspecified		Drug metabolism	=	21.0	%	PMID[485071]
NPT1574	Tissue	Liver	Homo sapiens	T1/2	=	20.0	hr	PMID[485071]
NPT1574	Tissue	Liver	Homo sapiens	CL	=	0.52	mL.min-1.kg-1	PMID[485071]
NPT27	Others	Unspecified		Drug metabolism	=	55.0	%	PMID[485071]
NPT3664	Tissue	Serum	Mus musculus	Drug degradation	=	27.0	%	PMID[485071]
NPT32	Organism	Mus musculus	Mus musculus	CL	=	16.0	mL.min-1.kg-1	PMID[485071]
NPT32	Organism	Mus musculus	Mus musculus	Vd	=	0.95	L.kg-1	PMID[485071]
NPT624	Tissue	Plasma	Mus musculus	C0	=	24.0	ug ml-1	PMID[485071]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	20000.0	ng.hr.mL-1	PMID[485071]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	26000.0	ng.hr.mL-1	PMID[485071]
NPT32	Organism	Mus musculus	Mus musculus	Tmax	=	1.5	hr	PMID[485071]
NPT32	Organism	Mus musculus	Mus musculus	Cmax	=	5.8	ug.mL-1	PMID[485071]
NPT32	Organism	Mus musculus	Mus musculus	T1/2	=	0.75	hr	PMID[485071]
NPT32	Organism	Mus musculus	Mus musculus	ka	=	0.24	/hr	PMID[485071]
NPT32	Organism	Mus musculus	Mus musculus	Kel	=	0.93	/hr	PMID[485071]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	499.0	nM	PMID[485071]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	377.0	nM	PMID[485071]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	Activity	=	55.0	%	PMID[485071]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	Activity	=	20.0	%	PMID[485071]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	Activity	=	27.0	%	PMID[485071]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	Activity	=	47.0	%	PMID[485071]

☑ 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 NPC97188 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	314
0.1-0.2	1362
0.2-0.3	2990
0.3-0.4	7085
0.4-0.5	11666
0.5-0.6	5268
0.6-0.7	10433
0.7-0.8	3514
0.8-0.85	50
0.85-0.9	9
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9786	High Similarity	NPC469498
0.9514	High Similarity	NPC37642
0.9444	High Similarity	NPC52931
0.9375	High Similarity	NPC17600
0.9315	High Similarity	NPC11892
0.9296	High Similarity	NPC271451
0.9184	High Similarity	NPC475093
0.8652	High Similarity	NPC302844
0.8633	High Similarity	NPC473744
0.8623	High Similarity	NPC204579
0.8582	High Similarity	NPC473777
0.8489	Intermediate Similarity	NPC110211
0.8478	Intermediate Similarity	NPC184219
0.8435	Intermediate Similarity	NPC469911
0.8406	Intermediate Similarity	NPC174991
0.8333	Intermediate Similarity	NPC67300
0.8278	Intermediate Similarity	NPC208293
0.8255	Intermediate Similarity	NPC184053
0.8201	Intermediate Similarity	NPC475192
0.8182	Intermediate Similarity	NPC267469
0.8182	Intermediate Similarity	NPC35160
0.8182	Intermediate Similarity	NPC117899
0.8182	Intermediate Similarity	NPC87630
0.8182	Intermediate Similarity	NPC179128
0.8182	Intermediate Similarity	NPC116292
0.8182	Intermediate Similarity	NPC162569
0.817	Intermediate Similarity	NPC325032
0.817	Intermediate Similarity	NPC66991
0.817	Intermediate Similarity	NPC477483
0.8169	Intermediate Similarity	NPC121104
0.8158	Intermediate Similarity	NPC258856
0.8129	Intermediate Similarity	NPC140133
0.8112	Intermediate Similarity	NPC229894
0.8112	Intermediate Similarity	NPC193203
0.8108	Intermediate Similarity	NPC119542
0.8105	Intermediate Similarity	NPC286038
0.8077	Intermediate Similarity	NPC48671
0.8069	Intermediate Similarity	NPC18798
0.8067	Intermediate Similarity	NPC172311
0.8065	Intermediate Similarity	NPC327962
0.8056	Intermediate Similarity	NPC194979
0.8054	Intermediate Similarity	NPC221104
0.8041	Intermediate Similarity	NPC475111
0.8041	Intermediate Similarity	NPC291454
0.8039	Intermediate Similarity	NPC75295
0.8028	Intermediate Similarity	NPC49938
0.8013	Intermediate Similarity	NPC470842
0.8	Intermediate Similarity	NPC327457
0.8	Intermediate Similarity	NPC86774
0.8	Intermediate Similarity	NPC279442
0.8	Intermediate Similarity	NPC109778
0.7987	Intermediate Similarity	NPC477592
0.7987	Intermediate Similarity	NPC170718
0.7987	Intermediate Similarity	NPC473023
0.7986	Intermediate Similarity	NPC2596
0.7974	Intermediate Similarity	NPC42540
0.7974	Intermediate Similarity	NPC151607
0.7971	Intermediate Similarity	NPC474890
0.7971	Intermediate Similarity	NPC161943
0.7971	Intermediate Similarity	NPC273282
0.7971	Intermediate Similarity	NPC94298
0.7971	Intermediate Similarity	NPC27633
0.7959	Intermediate Similarity	NPC239855
0.7949	Intermediate Similarity	NPC247219
0.7947	Intermediate Similarity	NPC472601
0.7947	Intermediate Similarity	NPC472600
0.7933	Intermediate Similarity	NPC477593
0.7908	Intermediate Similarity	NPC159721
0.7908	Intermediate Similarity	NPC469615
0.7905	Intermediate Similarity	NPC477594
0.7905	Intermediate Similarity	NPC204582
0.7905	Intermediate Similarity	NPC194970
0.7902	Intermediate Similarity	NPC137416
0.7895	Intermediate Similarity	NPC257003
0.7895	Intermediate Similarity	NPC472605
0.7895	Intermediate Similarity	NPC472604
0.7895	Intermediate Similarity	NPC471444
0.7895	Intermediate Similarity	NPC472603
0.7895	Intermediate Similarity	NPC477595
0.7881	Intermediate Similarity	NPC256463
0.7881	Intermediate Similarity	NPC299405
0.7881	Intermediate Similarity	NPC306835
0.7881	Intermediate Similarity	NPC111422
0.7881	Intermediate Similarity	NPC476477
0.7881	Intermediate Similarity	NPC473988
0.7881	Intermediate Similarity	NPC29771
0.7881	Intermediate Similarity	NPC216312
0.7881	Intermediate Similarity	NPC471602
0.7867	Intermediate Similarity	NPC194579
0.7867	Intermediate Similarity	NPC70380
0.7867	Intermediate Similarity	NPC71256
0.7862	Intermediate Similarity	NPC2401
0.7857	Intermediate Similarity	NPC469683
0.7857	Intermediate Similarity	NPC260152
0.7852	Intermediate Similarity	NPC477596
0.7852	Intermediate Similarity	NPC142027
0.7852	Intermediate Similarity	NPC27407
0.7847	Intermediate Similarity	NPC473751
0.7829	Intermediate Similarity	NPC32749
0.7829	Intermediate Similarity	NPC64664
0.7829	Intermediate Similarity	NPC42262
0.7829	Intermediate Similarity	NPC37992
0.7829	Intermediate Similarity	NPC327916
0.7829	Intermediate Similarity	NPC220496
0.7829	Intermediate Similarity	NPC147542
0.7829	Intermediate Similarity	NPC241349
0.7826	Intermediate Similarity	NPC83718
0.7826	Intermediate Similarity	NPC131192
0.7815	Intermediate Similarity	NPC212693
0.7815	Intermediate Similarity	NPC23870
0.7815	Intermediate Similarity	NPC472602
0.7815	Intermediate Similarity	NPC191835
0.7815	Intermediate Similarity	NPC478200
0.7815	Intermediate Similarity	NPC94248
0.7815	Intermediate Similarity	NPC33144
0.7812	Intermediate Similarity	NPC472807
0.7793	Intermediate Similarity	NPC37512
0.7792	Intermediate Similarity	NPC476473
0.7792	Intermediate Similarity	NPC478202
0.7792	Intermediate Similarity	NPC472610
0.7792	Intermediate Similarity	NPC471731
0.7786	Intermediate Similarity	NPC473767
0.7785	Intermediate Similarity	NPC180351
0.7785	Intermediate Similarity	NPC477893
0.7778	Intermediate Similarity	NPC158634
0.7778	Intermediate Similarity	NPC478217
0.7778	Intermediate Similarity	NPC53649
0.7778	Intermediate Similarity	NPC478201
0.7778	Intermediate Similarity	NPC472035
0.7778	Intermediate Similarity	NPC313123
0.777	Intermediate Similarity	NPC477407
0.777	Intermediate Similarity	NPC476389
0.777	Intermediate Similarity	NPC122117
0.777	Intermediate Similarity	NPC165612
0.7763	Intermediate Similarity	NPC112789
0.7763	Intermediate Similarity	NPC19622
0.7763	Intermediate Similarity	NPC88269
0.7763	Intermediate Similarity	NPC295339
0.7755	Intermediate Similarity	NPC163169
0.7755	Intermediate Similarity	NPC123
0.775	Intermediate Similarity	NPC62051
0.7748	Intermediate Similarity	NPC301915
0.7748	Intermediate Similarity	NPC261292
0.7742	Intermediate Similarity	NPC89664
0.7742	Intermediate Similarity	NPC210966
0.7742	Intermediate Similarity	NPC126882
0.7742	Intermediate Similarity	NPC478203
0.7742	Intermediate Similarity	NPC274085
0.7736	Intermediate Similarity	NPC221249
0.7736	Intermediate Similarity	NPC124842
0.7733	Intermediate Similarity	NPC173569
0.7733	Intermediate Similarity	NPC477874
0.7727	Intermediate Similarity	NPC470089
0.7727	Intermediate Similarity	NPC321980
0.7727	Intermediate Similarity	NPC474300
0.7727	Intermediate Similarity	NPC471733
0.7727	Intermediate Similarity	NPC470087
0.7722	Intermediate Similarity	NPC142654
0.7718	Intermediate Similarity	NPC472591
0.7718	Intermediate Similarity	NPC114116
0.7712	Intermediate Similarity	NPC168471
0.7712	Intermediate Similarity	NPC51181
0.7712	Intermediate Similarity	NPC158472
0.7712	Intermediate Similarity	NPC275903
0.7708	Intermediate Similarity	NPC221798
0.7707	Intermediate Similarity	NPC119767
0.7707	Intermediate Similarity	NPC14875
0.7707	Intermediate Similarity	NPC81835
0.7707	Intermediate Similarity	NPC5568
0.7703	Intermediate Similarity	NPC470831
0.7703	Intermediate Similarity	NPC15083
0.7703	Intermediate Similarity	NPC214702
0.7697	Intermediate Similarity	NPC161151
0.7697	Intermediate Similarity	NPC61590
0.7692	Intermediate Similarity	NPC257558
0.7692	Intermediate Similarity	NPC83272
0.7688	Intermediate Similarity	NPC256141
0.7688	Intermediate Similarity	NPC115249
0.7687	Intermediate Similarity	NPC226855
0.7682	Intermediate Similarity	NPC249817
0.7682	Intermediate Similarity	NPC235115
0.7677	Intermediate Similarity	NPC51106
0.7677	Intermediate Similarity	NPC112829
0.7677	Intermediate Similarity	NPC325346
0.7673	Intermediate Similarity	NPC188403
0.7667	Intermediate Similarity	NPC27643
0.7667	Intermediate Similarity	NPC477896
0.7667	Intermediate Similarity	NPC311339
0.7662	Intermediate Similarity	NPC67650
0.7662	Intermediate Similarity	NPC11056
0.7662	Intermediate Similarity	NPC471587
0.7662	Intermediate Similarity	NPC149533
0.7662	Intermediate Similarity	NPC1704
0.7658	Intermediate Similarity	NPC473719
0.7658	Intermediate Similarity	NPC161955
0.7655	Intermediate Similarity	NPC275576
0.7655	Intermediate Similarity	NPC165556
0.7647	Intermediate Similarity	NPC275356
0.7647	Intermediate Similarity	NPC475045
0.7647	Intermediate Similarity	NPC32360

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 NPC97188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	917
0.2-0.3	1589
0.3-0.4	2651
0.4-0.5	2086
0.5-0.6	1164
0.6-0.7	421
0.7-0.8	48
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7971	Intermediate Similarity	NPD9545	Approved
0.7829	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7635	Intermediate Similarity	NPD3764	Approved
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD7075	Discontinued
0.7423	Intermediate Similarity	NPD7819	Suspended
0.7423	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7358	Intermediate Similarity	NPD2533	Approved
0.7358	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2534	Approved
0.7358	Intermediate Similarity	NPD2532	Approved
0.7346	Intermediate Similarity	NPD4380	Phase 2
0.7325	Intermediate Similarity	NPD7003	Approved
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3750	Approved
0.7308	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7411	Suspended
0.7292	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4288	Approved
0.7246	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7768	Phase 2
0.7226	Intermediate Similarity	NPD2799	Discontinued
0.7226	Intermediate Similarity	NPD1510	Phase 2
0.7215	Intermediate Similarity	NPD8166	Discontinued
0.7212	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6651	Approved
0.7203	Intermediate Similarity	NPD9493	Approved
0.7197	Intermediate Similarity	NPD1549	Phase 2
0.719	Intermediate Similarity	NPD1240	Approved
0.7174	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6599	Discontinued
0.7134	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7236	Approved
0.711	Intermediate Similarity	NPD5844	Phase 1
0.7097	Intermediate Similarity	NPD1607	Approved
0.7081	Intermediate Similarity	NPD6799	Approved
0.7073	Intermediate Similarity	NPD3226	Approved
0.707	Intermediate Similarity	NPD2796	Approved
0.7063	Intermediate Similarity	NPD6190	Approved
0.7059	Intermediate Similarity	NPD2313	Discontinued
0.7035	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6232	Discontinued
0.7013	Intermediate Similarity	NPD6663	Approved
0.7006	Intermediate Similarity	NPD3748	Approved
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7473	Discontinued
0.6994	Remote Similarity	NPD6273	Approved
0.6993	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8150	Discontinued
0.6982	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3972	Approved
0.6974	Remote Similarity	NPD5736	Approved
0.6962	Remote Similarity	NPD1551	Phase 2
0.6962	Remote Similarity	NPD5408	Approved
0.6962	Remote Similarity	NPD5404	Approved
0.6962	Remote Similarity	NPD5406	Approved
0.6962	Remote Similarity	NPD5405	Approved
0.6954	Remote Similarity	NPD1164	Approved
0.6951	Remote Similarity	NPD920	Approved
0.6946	Remote Similarity	NPD1934	Approved
0.6933	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6832	Phase 2
0.6923	Remote Similarity	NPD6355	Discontinued
0.6918	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6005	Phase 3
0.6918	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6004	Phase 3
0.6918	Remote Similarity	NPD6002	Phase 3
0.6918	Remote Similarity	NPD2346	Discontinued
0.6918	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7286	Phase 2
0.6909	Remote Similarity	NPD7239	Suspended
0.6908	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4308	Phase 3
0.6892	Remote Similarity	NPD1778	Approved
0.6892	Remote Similarity	NPD4626	Approved
0.6889	Remote Similarity	NPD8434	Phase 2
0.6883	Remote Similarity	NPD7008	Discontinued
0.6882	Remote Similarity	NPD3749	Approved
0.6871	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1608	Approved
0.6867	Remote Similarity	NPD9717	Approved
0.6867	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2296	Approved
0.686	Remote Similarity	NPD6959	Discontinued
0.6855	Remote Similarity	NPD4477	Approved
0.6855	Remote Similarity	NPD6100	Approved
0.6855	Remote Similarity	NPD4476	Approved
0.6855	Remote Similarity	NPD6099	Approved
0.6842	Remote Similarity	NPD1203	Approved
0.6839	Remote Similarity	NPD6798	Discontinued
0.6836	Remote Similarity	NPD5953	Discontinued
0.6832	Remote Similarity	NPD1243	Approved
0.6831	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5691	Approved
0.6821	Remote Similarity	NPD5711	Approved
0.6821	Remote Similarity	NPD5710	Approved
0.6815	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5124	Phase 1
0.6813	Remote Similarity	NPD2344	Approved
0.681	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1283	Approved
0.6765	Remote Similarity	NPD3817	Phase 2
0.6763	Remote Similarity	NPD8127	Discontinued
0.6761	Remote Similarity	NPD2182	Approved
0.6761	Remote Similarity	NPD7177	Discontinued
0.6759	Remote Similarity	NPD1241	Discontinued
0.6752	Remote Similarity	NPD2979	Phase 3
0.6752	Remote Similarity	NPD4060	Phase 1
0.6748	Remote Similarity	NPD3887	Approved
0.674	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3496	Discontinued
0.6732	Remote Similarity	NPD1470	Approved
0.6732	Remote Similarity	NPD2797	Approved
0.6731	Remote Similarity	NPD3268	Approved
0.6725	Remote Similarity	NPD3882	Suspended
0.6721	Remote Similarity	NPD4287	Approved
0.6712	Remote Similarity	NPD5951	Approved
0.6708	Remote Similarity	NPD7266	Discontinued
0.6707	Remote Similarity	NPD7440	Discontinued
0.6706	Remote Similarity	NPD5761	Phase 2
0.6706	Remote Similarity	NPD2801	Approved
0.6706	Remote Similarity	NPD5760	Phase 2
0.6706	Remote Similarity	NPD8455	Phase 2
0.6704	Remote Similarity	NPD6559	Discontinued
0.6689	Remote Similarity	NPD1201	Approved
0.6689	Remote Similarity	NPD422	Phase 1
0.6688	Remote Similarity	NPD2798	Approved
0.6687	Remote Similarity	NPD5049	Phase 3
0.6686	Remote Similarity	NPD6385	Approved
0.6686	Remote Similarity	NPD6386	Approved
0.6685	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD7390	Discontinued
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2932	Approved
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD8651	Approved
0.6648	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6166	Phase 2
0.6647	Remote Similarity	NPD5403	Approved
0.6646	Remote Similarity	NPD4307	Phase 2
0.6646	Remote Similarity	NPD2354	Approved
0.6646	Remote Similarity	NPD943	Approved
0.6646	Remote Similarity	NPD2309	Approved
0.6645	Remote Similarity	NPD1481	Phase 2
0.6645	Remote Similarity	NPD9269	Phase 2
0.6645	Remote Similarity	NPD9494	Approved
0.6643	Remote Similarity	NPD74	Approved
0.6643	Remote Similarity	NPD9266	Approved
0.663	Remote Similarity	NPD8312	Approved
0.663	Remote Similarity	NPD8313	Approved
0.6629	Remote Similarity	NPD7054	Approved
0.6629	Remote Similarity	NPD7229	Phase 3
0.6625	Remote Similarity	NPD7097	Phase 1
0.6622	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6764	Approved
0.6611	Remote Similarity	NPD7685	Pre-registration
0.6611	Remote Similarity	NPD6765	Approved
0.6609	Remote Similarity	NPD5494	Approved
0.6608	Remote Similarity	NPD1465	Phase 2
0.6604	Remote Similarity	NPD447	Suspended
0.6604	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.66	Remote Similarity	NPD9268	Approved
0.6599	Remote Similarity	NPD2629	Approved
0.6592	Remote Similarity	NPD7472	Approved
0.6587	Remote Similarity	NPD1512	Approved
0.6585	Remote Similarity	NPD3400	Discontinued
0.6582	Remote Similarity	NPD6233	Phase 2
0.6581	Remote Similarity	NPD1019	Discontinued
0.6579	Remote Similarity	NPD1535	Discovery
0.6579	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1281	Approved
0.6573	Remote Similarity	NPD7799	Discontinued
0.6573	Remote Similarity	NPD9263	Approved
0.6573	Remote Similarity	NPD9267	Approved
0.6573	Remote Similarity	NPD9264	Approved
0.657	Remote Similarity	NPD5402	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