NPASS Compound

Structure

CID87306 OpenBabel06191715422D 22 23 0 0 1 0 0 0 0 0999 V2000 0.3727 6.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5317 5.0158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2330 1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0454 3.6776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1625 4.6557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6977 3.0085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5806 5.3249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4898 2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4487 -0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4487 2.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -1.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -1.7796 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 2 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 14 19 1 6 0 0 0 15 18 1 0 0 0 0 15 20 2 0 0 0 0 16 18 1 6 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.17
Volume:	324.75
LogP:	2.55
LogD:	2.013
LogS:	-4.123
# Rotatable Bonds:	4
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	4.525
Fsp3:	0.611
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.777
MDCK Permeability:	3.0046718165976927e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.394
Human Intestinal Absorption (HIA):	0.171
20% Bioavailability (F20%):	0.341
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.919
Plasma Protein Binding (PPB):	83.9842758178711%
Volume Distribution (VD):	1.272
Pgp-substrate:	8.98058795928955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.461
CYP2C19-substrate:	0.4
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.32
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	7.193
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.866
Drug-inuced Liver Injury (DILI):	0.29
AMES Toxicity:	0.809
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.289
Carcinogencity:	0.111
Eye Corrosion:	0.005
Eye Irritation:	0.045
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC87306

Natural Product ID:	NPC87306
*Common Name:**	(+)-Miliusol
IUPAC Name:	(1R,5R,9S)-1-[(1E)-2,6-dimethylhepta-1,5-dienyl]-9-hydroxy-2-oxaspiro[4.5]dec-7-ene-3,6-dione
Synonyms:	(+)-Miliusol
Standard InCHIKey:	LZYGZWJAFQLDDH-FWDDYHNSSA-N
Standard InCHI:	InChI=1S/C18H24O4/c1-12(2)5-4-6-13(3)9-16-18(11-17(21)22-16)10-14(19)7-8-15(18)20/h5,7-9,14,16,19H,4,6,10-11H2,1-3H3/b13-9+/t14-,16-,18+/m1/s1
SMILES:	C/C(=C[C@H]1OC(=O)C[C@@]21C[C@H](O)C=CC2=O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL382849
PubChem CID:	11956143
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO22093	Miliusa sinensis	Species	Annonaceae	Eukaryota	dried leaves, twigs, and flowers	Vietnam	n.a.	PMID[16420055]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[26238320]
NPO40203	Miliusa cuneata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26928423]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22093	Miliusa sinensis	Species	Annonaceae	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
GI50	1
IC50	17
Others	18

Activity Type	# Activity
Cell Line	29
Organism	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1180.0	nM	PMID[560036]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	1640.0	nM	PMID[560036]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	1350.0	nM	PMID[560036]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	1780.0	nM	PMID[560036]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3090.0	nM	PMID[560036]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	660.0	nM	PMID[560036]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	1320.0	nM	PMID[560036]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1230.0	nM	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	1520.0	nM	PMID[560037]
NPT1083	Cell Line	A-375	Homo sapiens	TGI	=	20.6	%	PMID[560037]
NPT1083	Cell Line	A-375	Homo sapiens	TGI	=	12.8	%	PMID[560037]
NPT165	Cell Line	HeLa	Homo sapiens	TGI	=	30.0	%	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	TGI	=	29.9	%	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	TGI	=	68.7	%	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	TGI	=	72.7	%	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	68.7	%	PMID[560037]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	31.5	%	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	3670.0	nM	PMID[560037]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2450.0	nM	PMID[560037]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	1500.0	nM	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	2000.0	nM	PMID[560037]
NPT517	Cell Line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	30.0	nM	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	88.2	%	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	4.4	%	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	4.9	%	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	2.5	%	PMID[560037]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	72.7	%	PMID[560037]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10200.0	nM	PMID[560038]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	13500.0	nM	PMID[560038]
NPT2	Others	Unspecified		Ratio IC50	=	1.1	n.a.	PMID[560037]
NPT2	Others	Unspecified		Ratio IC50	=	0.9	n.a.	PMID[560037]
NPT27	Others	Unspecified		Activity	=	1.0	g	PMID[560037]
NPT2	Others	Unspecified		Ratio IC50	=	1.0	n.a.	PMID[560037]
NPT2	Others	Unspecified		Ratio IC50	=	0.8	n.a.	PMID[560037]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	11100.0	nM	PMID[560038]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	9100.0	nM	PMID[560038]

☑ 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 NPC87306 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	178
0.1-0.2	1288
0.2-0.3	5499
0.3-0.4	10647
0.4-0.5	13905
0.5-0.6	6710
0.6-0.7	3832
0.7-0.8	622
0.8-0.85	4
0.85-0.9	2
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC473455
0.9759	High Similarity	NPC473248
0.9643	High Similarity	NPC153570
0.9432	High Similarity	NPC214694
0.9398	High Similarity	NPC163615
0.9398	High Similarity	NPC38569
0.9398	High Similarity	NPC219966
0.9286	High Similarity	NPC155873
0.9048	High Similarity	NPC52923
0.8864	High Similarity	NPC78008
0.8588	High Similarity	NPC275507
0.8105	Intermediate Similarity	NPC11396
0.8105	Intermediate Similarity	NPC21302
0.8021	Intermediate Similarity	NPC17326
0.8021	Intermediate Similarity	NPC134454
0.8	Intermediate Similarity	NPC477922
0.8	Intermediate Similarity	NPC471142
0.798	Intermediate Similarity	NPC110989
0.7957	Intermediate Similarity	NPC106510
0.7957	Intermediate Similarity	NPC71533
0.7955	Intermediate Similarity	NPC474980
0.7938	Intermediate Similarity	NPC23364
0.7938	Intermediate Similarity	NPC141191
0.7917	Intermediate Similarity	NPC477921
0.7917	Intermediate Similarity	NPC185553
0.7912	Intermediate Similarity	NPC278283
0.7912	Intermediate Similarity	NPC478112
0.79	Intermediate Similarity	NPC203659
0.7879	Intermediate Similarity	NPC225353
0.7879	Intermediate Similarity	NPC235369
0.7872	Intermediate Similarity	NPC473321
0.7849	Intermediate Similarity	NPC295312
0.7835	Intermediate Similarity	NPC169205
0.7802	Intermediate Similarity	NPC21469
0.7802	Intermediate Similarity	NPC470755
0.7789	Intermediate Similarity	NPC295204
0.7789	Intermediate Similarity	NPC288240
0.7789	Intermediate Similarity	NPC273579
0.7789	Intermediate Similarity	NPC162205
0.7766	Intermediate Similarity	NPC473619
0.7766	Intermediate Similarity	NPC179394
0.7766	Intermediate Similarity	NPC475855
0.7766	Intermediate Similarity	NPC144133
0.7753	Intermediate Similarity	NPC297440
0.7742	Intermediate Similarity	NPC475819
0.7742	Intermediate Similarity	NPC473715
0.7742	Intermediate Similarity	NPC150063
0.7742	Intermediate Similarity	NPC119740
0.7708	Intermediate Similarity	NPC475927
0.7708	Intermediate Similarity	NPC475832
0.7692	Intermediate Similarity	NPC158756
0.7692	Intermediate Similarity	NPC32676
0.7684	Intermediate Similarity	NPC233437
0.7684	Intermediate Similarity	NPC207641
0.7684	Intermediate Similarity	NPC472705
0.7677	Intermediate Similarity	NPC288876
0.766	Intermediate Similarity	NPC474032
0.7653	Intermediate Similarity	NPC40812
0.7653	Intermediate Similarity	NPC70145
0.7653	Intermediate Similarity	NPC91695
0.7634	Intermediate Similarity	NPC160138
0.7629	Intermediate Similarity	NPC275960
0.7629	Intermediate Similarity	NPC48803
0.7629	Intermediate Similarity	NPC193645
0.7629	Intermediate Similarity	NPC90121
0.7624	Intermediate Similarity	NPC472755
0.7624	Intermediate Similarity	NPC475945
0.7624	Intermediate Similarity	NPC475871
0.7614	Intermediate Similarity	NPC93763
0.7614	Intermediate Similarity	NPC108816
0.7614	Intermediate Similarity	NPC127526
0.7604	Intermediate Similarity	NPC475912
0.76	Intermediate Similarity	NPC472753
0.76	Intermediate Similarity	NPC171759
0.7582	Intermediate Similarity	NPC169575
0.7582	Intermediate Similarity	NPC250315
0.7582	Intermediate Similarity	NPC40746
0.7582	Intermediate Similarity	NPC116543
0.7576	Intermediate Similarity	NPC261377
0.7576	Intermediate Similarity	NPC255592
0.7576	Intermediate Similarity	NPC471144
0.7576	Intermediate Similarity	NPC187761
0.7576	Intermediate Similarity	NPC83895
0.7576	Intermediate Similarity	NPC308567
0.7558	Intermediate Similarity	NPC476590
0.7558	Intermediate Similarity	NPC114727
0.7553	Intermediate Similarity	NPC202672
0.7553	Intermediate Similarity	NPC476805
0.7551	Intermediate Similarity	NPC473859
0.7551	Intermediate Similarity	NPC230800
0.7549	Intermediate Similarity	NPC100487
0.7527	Intermediate Similarity	NPC469910
0.7526	Intermediate Similarity	NPC474035
0.7526	Intermediate Similarity	NPC81386
0.7526	Intermediate Similarity	NPC469632
0.7525	Intermediate Similarity	NPC474747
0.7525	Intermediate Similarity	NPC149371
0.7525	Intermediate Similarity	NPC472754
0.7524	Intermediate Similarity	NPC5103
0.75	Intermediate Similarity	NPC320630
0.75	Intermediate Similarity	NPC116177
0.75	Intermediate Similarity	NPC306856
0.75	Intermediate Similarity	NPC472958
0.75	Intermediate Similarity	NPC300312
0.75	Intermediate Similarity	NPC261607
0.75	Intermediate Similarity	NPC31086
0.75	Intermediate Similarity	NPC472957
0.75	Intermediate Similarity	NPC7563
0.75	Intermediate Similarity	NPC30515
0.75	Intermediate Similarity	NPC284185
0.75	Intermediate Similarity	NPC89171
0.75	Intermediate Similarity	NPC474251
0.75	Intermediate Similarity	NPC111114
0.75	Intermediate Similarity	NPC212363
0.75	Intermediate Similarity	NPC476802
0.7475	Intermediate Similarity	NPC245521
0.7475	Intermediate Similarity	NPC471462
0.7475	Intermediate Similarity	NPC474343
0.747	Intermediate Similarity	NPC106613
0.7449	Intermediate Similarity	NPC304886
0.7449	Intermediate Similarity	NPC270013
0.7449	Intermediate Similarity	NPC36954
0.7449	Intermediate Similarity	NPC14961
0.7449	Intermediate Similarity	NPC475659
0.7447	Intermediate Similarity	NPC72513
0.7426	Intermediate Similarity	NPC133907
0.7426	Intermediate Similarity	NPC474742
0.7426	Intermediate Similarity	NPC244456
0.7426	Intermediate Similarity	NPC185141
0.7426	Intermediate Similarity	NPC128733
0.7426	Intermediate Similarity	NPC47880
0.7426	Intermediate Similarity	NPC46998
0.7426	Intermediate Similarity	NPC110443
0.7426	Intermediate Similarity	NPC469657
0.7423	Intermediate Similarity	NPC469692
0.7423	Intermediate Similarity	NPC179746
0.7423	Intermediate Similarity	NPC81419
0.7423	Intermediate Similarity	NPC475838
0.7423	Intermediate Similarity	NPC228451
0.7423	Intermediate Similarity	NPC125674
0.7423	Intermediate Similarity	NPC469645
0.7419	Intermediate Similarity	NPC125290
0.7419	Intermediate Similarity	NPC261380
0.7416	Intermediate Similarity	NPC267231
0.7416	Intermediate Similarity	NPC279532
0.74	Intermediate Similarity	NPC300584
0.7396	Intermediate Similarity	NPC253144
0.7396	Intermediate Similarity	NPC474761
0.7396	Intermediate Similarity	NPC145666
0.7396	Intermediate Similarity	NPC474232
0.7396	Intermediate Similarity	NPC476004
0.7396	Intermediate Similarity	NPC51004
0.7391	Intermediate Similarity	NPC473390
0.7391	Intermediate Similarity	NPC318468
0.7391	Intermediate Similarity	NPC131669
0.7391	Intermediate Similarity	NPC16488
0.7391	Intermediate Similarity	NPC161045
0.7383	Intermediate Similarity	NPC66108
0.7379	Intermediate Similarity	NPC146731
0.7379	Intermediate Similarity	NPC474741
0.7379	Intermediate Similarity	NPC309190
0.7379	Intermediate Similarity	NPC296950
0.7379	Intermediate Similarity	NPC475676
0.7379	Intermediate Similarity	NPC220964
0.7379	Intermediate Similarity	NPC472756
0.7374	Intermediate Similarity	NPC126156
0.7374	Intermediate Similarity	NPC202833
0.7374	Intermediate Similarity	NPC476315
0.7368	Intermediate Similarity	NPC476803
0.7363	Intermediate Similarity	NPC24417
0.7358	Intermediate Similarity	NPC41551
0.7347	Intermediate Similarity	NPC167219
0.7347	Intermediate Similarity	NPC303942
0.7347	Intermediate Similarity	NPC53685
0.7347	Intermediate Similarity	NPC57405
0.7347	Intermediate Similarity	NPC474247
0.7347	Intermediate Similarity	NPC121825
0.734	Intermediate Similarity	NPC112685
0.734	Intermediate Similarity	NPC122502
0.734	Intermediate Similarity	NPC305475
0.734	Intermediate Similarity	NPC261721
0.734	Intermediate Similarity	NPC315395
0.734	Intermediate Similarity	NPC309211
0.734	Intermediate Similarity	NPC477010
0.734	Intermediate Similarity	NPC475461
0.734	Intermediate Similarity	NPC316426
0.734	Intermediate Similarity	NPC284902
0.7333	Intermediate Similarity	NPC264819
0.7333	Intermediate Similarity	NPC473980
0.7333	Intermediate Similarity	NPC189075
0.7333	Intermediate Similarity	NPC473981
0.7333	Intermediate Similarity	NPC475210
0.7333	Intermediate Similarity	NPC275539
0.7327	Intermediate Similarity	NPC475949
0.7327	Intermediate Similarity	NPC54705
0.7327	Intermediate Similarity	NPC174314
0.7327	Intermediate Similarity	NPC280963
0.732	Intermediate Similarity	NPC12172
0.732	Intermediate Similarity	NPC74103
0.732	Intermediate Similarity	NPC184463

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 NPC87306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1864
0.2-0.3	4033
0.3-0.4	2116
0.4-0.5	621
0.5-0.6	279
0.6-0.7	80
0.7-0.8	4
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
0.7629	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5785	Approved
0.7097	Intermediate Similarity	NPD5209	Approved
0.7037	Intermediate Similarity	NPD6371	Approved
0.6979	Remote Similarity	NPD5786	Approved
0.697	Remote Similarity	NPD7983	Approved
0.69	Remote Similarity	NPD5778	Approved
0.69	Remote Similarity	NPD5779	Approved
0.6893	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4225	Approved
0.6875	Remote Similarity	NPD1694	Approved
0.6875	Remote Similarity	NPD5363	Approved
0.6869	Remote Similarity	NPD6698	Approved
0.6869	Remote Similarity	NPD46	Approved
0.6842	Remote Similarity	NPD6110	Phase 1
0.6832	Remote Similarity	NPD5282	Discontinued
0.6702	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7637	Suspended
0.6633	Remote Similarity	NPD4249	Approved
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7638	Approved
0.6566	Remote Similarity	NPD4251	Approved
0.6566	Remote Similarity	NPD4250	Approved
0.6562	Remote Similarity	NPD4270	Approved
0.6562	Remote Similarity	NPD4269	Approved
0.6545	Remote Similarity	NPD6686	Approved
0.6538	Remote Similarity	NPD7839	Suspended
0.6535	Remote Similarity	NPD7838	Discovery
0.6531	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD6411	Approved
0.6441	Remote Similarity	NPD8515	Approved
0.6441	Remote Similarity	NPD8517	Approved
0.6441	Remote Similarity	NPD8516	Approved
0.6441	Remote Similarity	NPD8513	Phase 3
0.6392	Remote Similarity	NPD6435	Approved
0.6392	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6650	Approved
0.6372	Remote Similarity	NPD6649	Approved
0.6356	Remote Similarity	NPD6319	Approved
0.6354	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD8039	Approved
0.6327	Remote Similarity	NPD7154	Phase 3
0.6316	Remote Similarity	NPD6053	Discontinued
0.6311	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5697	Approved
0.6289	Remote Similarity	NPD5369	Approved
0.6281	Remote Similarity	NPD7492	Approved
0.6275	Remote Similarity	NPD5370	Suspended
0.6275	Remote Similarity	NPD6101	Approved
0.6275	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD6881	Approved
0.623	Remote Similarity	NPD6616	Approved
0.6228	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6054	Approved
0.6216	Remote Similarity	NPD6008	Approved
0.6211	Remote Similarity	NPD4756	Discovery
0.62	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6372	Approved
0.6195	Remote Similarity	NPD6014	Approved
0.6195	Remote Similarity	NPD6013	Approved
0.6195	Remote Similarity	NPD6373	Approved
0.6195	Remote Similarity	NPD6012	Approved
0.6186	Remote Similarity	NPD5368	Approved
0.6179	Remote Similarity	NPD7078	Approved
0.6179	Remote Similarity	NPD8074	Phase 3
0.6168	Remote Similarity	NPD7902	Approved
0.6167	Remote Similarity	NPD6015	Approved
0.6167	Remote Similarity	NPD6016	Approved
0.6162	Remote Similarity	NPD5362	Discontinued
0.6147	Remote Similarity	NPD5344	Discontinued
0.6146	Remote Similarity	NPD4268	Approved
0.6146	Remote Similarity	NPD4271	Approved
0.614	Remote Similarity	NPD6883	Approved
0.614	Remote Similarity	NPD7290	Approved
0.614	Remote Similarity	NPD7102	Approved
0.614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7736	Approved
0.6117	Remote Similarity	NPD1695	Approved
0.6116	Remote Similarity	NPD6370	Approved
0.6116	Remote Similarity	NPD5988	Approved
0.6111	Remote Similarity	NPD7260	Phase 2
0.6106	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6009	Approved
0.6091	Remote Similarity	NPD5211	Phase 2
0.6091	Remote Similarity	NPD7632	Discontinued
0.6087	Remote Similarity	NPD6617	Approved
0.6087	Remote Similarity	NPD8130	Phase 1
0.6087	Remote Similarity	NPD6847	Approved
0.6087	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD5739	Approved
0.6071	Remote Similarity	NPD7128	Approved
0.6071	Remote Similarity	NPD5048	Discontinued
0.6071	Remote Similarity	NPD6402	Approved
0.6071	Remote Similarity	NPD6675	Approved
0.6067	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7642	Approved
0.6053	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8297	Approved
0.6034	Remote Similarity	NPD6882	Approved
0.6033	Remote Similarity	NPD5983	Phase 2
0.602	Remote Similarity	NPD4822	Approved
0.602	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4821	Approved
0.602	Remote Similarity	NPD4819	Approved
0.602	Remote Similarity	NPD4820	Approved
0.6018	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5141	Approved
0.5977	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7500	Approved
0.5965	Remote Similarity	NPD7320	Approved
0.5952	Remote Similarity	NPD7319	Approved
0.595	Remote Similarity	NPD6059	Approved
0.5935	Remote Similarity	NPD8328	Phase 3
0.5935	Remote Similarity	NPD7830	Approved
0.5935	Remote Similarity	NPD7829	Approved
0.5935	Remote Similarity	NPD7604	Phase 2
0.5926	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5222	Approved
0.5926	Remote Similarity	NPD4697	Phase 3
0.5926	Remote Similarity	NPD5221	Approved
0.592	Remote Similarity	NPD8293	Discontinued
0.5909	Remote Similarity	NPD5285	Approved
0.5909	Remote Similarity	NPD5286	Approved
0.5909	Remote Similarity	NPD4696	Approved
0.5909	Remote Similarity	NPD6648	Approved
0.5902	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6647	Phase 2
0.5888	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7900	Approved
0.5888	Remote Similarity	NPD7748	Approved
0.5882	Remote Similarity	NPD1696	Phase 3
0.5877	Remote Similarity	NPD6412	Phase 2
0.5877	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6083	Phase 2
0.5872	Remote Similarity	NPD6084	Phase 2
0.5872	Remote Similarity	NPD5173	Approved
0.5856	Remote Similarity	NPD5223	Approved
0.5849	Remote Similarity	NPD5281	Approved
0.5849	Remote Similarity	NPD7515	Phase 2
0.5849	Remote Similarity	NPD5284	Approved
0.5842	Remote Similarity	NPD5331	Approved
0.5842	Remote Similarity	NPD5332	Approved
0.584	Remote Similarity	NPD7507	Approved
0.584	Remote Similarity	NPD6336	Discontinued
0.5833	Remote Similarity	NPD6317	Approved
0.5833	Remote Similarity	NPD5695	Phase 3
0.5825	Remote Similarity	NPD6684	Approved
0.5825	Remote Similarity	NPD7521	Approved
0.5825	Remote Similarity	NPD6409	Approved
0.5825	Remote Similarity	NPD7334	Approved
0.5825	Remote Similarity	NPD3618	Phase 1
0.5825	Remote Similarity	NPD7146	Approved
0.5825	Remote Similarity	NPD5330	Approved
0.5818	Remote Similarity	NPD5696	Approved
0.5814	Remote Similarity	NPD6845	Suspended
0.5812	Remote Similarity	NPD2204	Approved
0.5812	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5328	Approved
0.5804	Remote Similarity	NPD5226	Approved
0.5804	Remote Similarity	NPD5225	Approved
0.5804	Remote Similarity	NPD5224	Approved
0.5804	Remote Similarity	NPD4633	Approved
0.58	Remote Similarity	NPD4790	Discontinued
0.5798	Remote Similarity	NPD6010	Discontinued
0.5785	Remote Similarity	NPD7641	Discontinued
0.5785	Remote Similarity	NPD6314	Approved
0.5785	Remote Similarity	NPD6313	Approved
0.5785	Remote Similarity	NPD6335	Approved
0.5784	Remote Similarity	NPD3133	Approved
0.5784	Remote Similarity	NPD3666	Approved
0.5784	Remote Similarity	NPD3665	Phase 1
0.5778	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD8444	Approved
0.5769	Remote Similarity	NPD3573	Approved
0.5752	Remote Similarity	NPD5175	Approved
0.5752	Remote Similarity	NPD5174	Approved
0.575	Remote Similarity	NPD6868	Approved
0.575	Remote Similarity	NPD6274	Approved
0.5738	Remote Similarity	NPD7100	Approved
0.5738	Remote Similarity	NPD7101	Approved
0.573	Remote Similarity	NPD4191	Approved
0.573	Remote Similarity	NPD4194	Approved
0.573	Remote Similarity	NPD4192	Approved
0.573	Remote Similarity	NPD4193	Approved
0.5727	Remote Similarity	NPD4755	Approved
0.5714	Remote Similarity	NPD5737	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