NPASS Compound

Structure

CID236637 OpenBabel06191716032D 22 24 0 0 1 0 0 0 0 0999 V2000 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 21 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 2 0 0 0 0 13 8 1 6 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	2.491
LogD:	2.54
LogS:	-4.108
# Rotatable Bonds:	2
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	2.89
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.79
MDCK Permeability:	1.2604423318407498e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	93.53272247314453%
Volume Distribution (VD):	0.805
Pgp-substrate:	9.10606575012207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.877
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.616
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.741
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.599
CYP2D6-substrate:	0.713
CYP3A4-inhibitor:	0.791
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	16.782
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.123
Rat Oral Acute Toxicity:	0.821
Maximum Recommended Daily Dose:	0.569
Skin Sensitization:	0.91
Carcinogencity:	0.555
Eye Corrosion:	0.017
Eye Irritation:	0.934
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC236637

Natural Product ID:	NPC236637
*Common Name:**	Homoeriodictyol
IUPAC Name:	(2S)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	(+/-)-Homoeriodictyol; (-)-Homoeriodictyol; Homoeriodictyol
Standard InCHIKey:	FTODBIPDTXRIGS-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-6,13,17-19H,7H2,1H3/t13-/m0/s1
SMILES:	COc1cc(ccc1O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490170
PubChem CID:	73635
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002595] 3'-O-methylated flavonoids

*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
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO11318	Eriodictyon californicum	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593282]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[2082684]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21922656]
NPO41833	A new engineered strain of Aspergillus spp. [n.a.]	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23621425]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3254039]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3256207]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO41833	A new engineered strain of Aspergillus spp. [n.a.]	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34947068]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	twig	n.a.	PMID[9179367]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11318	Eriodictyon californicum	Species	Namaceae	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
EC50	1
IC50	9
Others	19
Potency	1

Activity Type	# Activity
Cell Line	2
Individual Protein	13
Others	13
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	240.0	nM	PMID[515721]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	>	4000.0	nM	PMID[515721]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	>	4000.0	nM	PMID[515721]
NPT71	Cell Line	HEK293	Homo sapiens	FC	=	1.2	n.a.	PMID[515724]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	1716.0	nM	PMID[515725]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	19109.0	nM	PMID[515725]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	37768.0	nM	PMID[515725]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	17782.8	nM	PMID[515726]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	89.1	%	PMID[515727]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	29.46	%	PMID[515728]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	240.0	nM	PMID[515731]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	19100.0	nM	PMID[515731]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	37800.0	nM	PMID[515731]
NPT1651	Individual Protein	Nuclear factor erythroid 2-related factor 2	Mus musculus	FC	=	1.51	n.a.	PMID[515732]
NPT2	Others	Unspecified		Inhibition	=	-36.0	%	PMID[515722]
NPT2	Others	Unspecified		Activity	=	0.0	n.a.	PMID[515723]
NPT177	Tissue	Aorta	Rattus norvegicus	EC50	=	82000.0	nM	PMID[515727]
NPT177	Tissue	Aorta	Rattus norvegicus	Emax	=	74.9	%	PMID[515727]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	3.1	%	PMID[515728]
NPT35	Others	n.a.		Retention_time	=	0.89	min	PMID[515729]
NPT35	Others	n.a.		Retention_time	=	0.85	min	PMID[515729]
NPT27	Others	Unspecified		Activity	=	106.0	%	PMID[515730]
NPT27	Others	Unspecified		Activity	=	107.0	%	PMID[515730]
NPT27	Others	Unspecified		Activity	=	95.0	%	PMID[515730]
NPT27	Others	Unspecified		Activity	=	94.0	%	PMID[515730]
NPT27	Others	Unspecified		Activity	=	98.0	%	PMID[515730]
NPT27	Others	Unspecified		Activity	=	100.0	%	PMID[515730]
NPT27	Others	Unspecified		Activity	=	99.0	%	PMID[515730]
NPT27	Others	Unspecified		Activity	=	102.0	%	PMID[515730]

☑ 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 NPC236637 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	398
0.1-0.2	1606
0.2-0.3	4253
0.3-0.4	10242
0.4-0.5	7684
0.5-0.6	3296
0.6-0.7	4641
0.7-0.8	5332
0.8-0.85	2810
0.85-0.9	1685
0.9-0.95	600
0.95-1	150

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC219582
1.0	High Similarity	NPC302950
0.9932	High Similarity	NPC18727
0.9797	High Similarity	NPC35038
0.9797	High Similarity	NPC326037
0.9797	High Similarity	NPC13858
0.9797	High Similarity	NPC195796
0.9797	High Similarity	NPC320825
0.9797	High Similarity	NPC235165
0.9797	High Similarity	NPC278778
0.9797	High Similarity	NPC291878
0.9797	High Similarity	NPC255106
0.9732	High Similarity	NPC472598
0.9732	High Similarity	NPC99597
0.9732	High Similarity	NPC471479
0.9732	High Similarity	NPC474836
0.9732	High Similarity	NPC48208
0.9732	High Similarity	NPC210084
0.9732	High Similarity	NPC162869
0.9732	High Similarity	NPC52530
0.9732	High Similarity	NPC471515
0.9732	High Similarity	NPC156057
0.9732	High Similarity	NPC474208
0.9732	High Similarity	NPC291508
0.9732	High Similarity	NPC474055
0.9732	High Similarity	NPC27337
0.9732	High Similarity	NPC475267
0.973	High Similarity	NPC45849
0.973	High Similarity	NPC477503
0.973	High Similarity	NPC200761
0.973	High Similarity	NPC470327
0.9728	High Similarity	NPC260979
0.9728	High Similarity	NPC472912
0.9726	High Similarity	NPC338131
0.9724	High Similarity	NPC294852
0.9724	High Similarity	NPC321011
0.9724	High Similarity	NPC188679
0.9664	High Similarity	NPC470328
0.9664	High Similarity	NPC209614
0.9664	High Similarity	NPC472626
0.9664	High Similarity	NPC471500
0.9664	High Similarity	NPC250922
0.9662	High Similarity	NPC192083
0.9662	High Similarity	NPC469550
0.9662	High Similarity	NPC213896
0.966	High Similarity	NPC31363
0.9658	High Similarity	NPC1612
0.9658	High Similarity	NPC287101
0.9658	High Similarity	NPC223579
0.9658	High Similarity	NPC183950
0.9658	High Similarity	NPC137062
0.9658	High Similarity	NPC183959
0.9658	High Similarity	NPC52005
0.9603	High Similarity	NPC118256
0.9603	High Similarity	NPC192686
0.9603	High Similarity	NPC263449
0.9603	High Similarity	NPC287328
0.9603	High Similarity	NPC282009
0.9603	High Similarity	NPC119209
0.9603	High Similarity	NPC472624
0.9603	High Similarity	NPC36217
0.96	High Similarity	NPC472911
0.96	High Similarity	NPC245758
0.96	High Similarity	NPC223787
0.96	High Similarity	NPC472914
0.96	High Similarity	NPC299520
0.96	High Similarity	NPC129684
0.96	High Similarity	NPC67876
0.96	High Similarity	NPC472910
0.96	High Similarity	NPC472913
0.96	High Similarity	NPC222814
0.96	High Similarity	NPC96167
0.9597	High Similarity	NPC37392
0.9597	High Similarity	NPC321779
0.9597	High Similarity	NPC2928
0.9597	High Similarity	NPC67396
0.9597	High Similarity	NPC226025
0.9595	High Similarity	NPC199100
0.9595	High Similarity	NPC106976
0.9595	High Similarity	NPC260491
0.9595	High Similarity	NPC240476
0.9595	High Similarity	NPC477231
0.9595	High Similarity	NPC120537
0.9595	High Similarity	NPC61506
0.9595	High Similarity	NPC36835
0.9595	High Similarity	NPC9743
0.9595	High Similarity	NPC257648
0.9595	High Similarity	NPC180234
0.9595	High Similarity	NPC246162
0.9592	High Similarity	NPC29231
0.9589	High Similarity	NPC3036
0.9589	High Similarity	NPC120464
0.9539	High Similarity	NPC308992
0.9539	High Similarity	NPC474038
0.9539	High Similarity	NPC471210
0.9539	High Similarity	NPC472634
0.9539	High Similarity	NPC471499
0.9539	High Similarity	NPC173137
0.9539	High Similarity	NPC158188
0.9539	High Similarity	NPC26326
0.9539	High Similarity	NPC472632
0.9536	High Similarity	NPC55738
0.9536	High Similarity	NPC95936
0.9536	High Similarity	NPC22192
0.9536	High Similarity	NPC250214
0.9533	High Similarity	NPC472916
0.9533	High Similarity	NPC474638
0.9533	High Similarity	NPC24640
0.953	High Similarity	NPC246328
0.953	High Similarity	NPC167091
0.953	High Similarity	NPC271779
0.953	High Similarity	NPC88645
0.953	High Similarity	NPC74924
0.953	High Similarity	NPC298692
0.953	High Similarity	NPC256346
0.953	High Similarity	NPC27532
0.953	High Similarity	NPC325028
0.953	High Similarity	NPC141212
0.953	High Similarity	NPC206238
0.953	High Similarity	NPC292214
0.9527	High Similarity	NPC125062
0.9527	High Similarity	NPC252933
0.9527	High Similarity	NPC54394
0.9527	High Similarity	NPC204515
0.9527	High Similarity	NPC117579
0.9527	High Similarity	NPC200740
0.9524	High Similarity	NPC105512
0.9524	High Similarity	NPC48479
0.9524	High Similarity	NPC177298
0.9521	High Similarity	NPC95864
0.9521	High Similarity	NPC108406
0.9521	High Similarity	NPC12200
0.9477	High Similarity	NPC472635
0.9477	High Similarity	NPC201800
0.9477	High Similarity	NPC474034
0.9477	High Similarity	NPC472964
0.9477	High Similarity	NPC474033
0.9477	High Similarity	NPC476247
0.9474	High Similarity	NPC472631
0.9474	High Similarity	NPC174953
0.9474	High Similarity	NPC475784
0.9474	High Similarity	NPC472630
0.9474	High Similarity	NPC472902
0.9474	High Similarity	NPC471744
0.9474	High Similarity	NPC470183
0.9474	High Similarity	NPC470326
0.947	High Similarity	NPC108456
0.947	High Similarity	NPC471209
0.947	High Similarity	NPC470402
0.947	High Similarity	NPC469584
0.947	High Similarity	NPC78225
0.947	High Similarity	NPC473272
0.947	High Similarity	NPC284820
0.9467	High Similarity	NPC213622
0.9467	High Similarity	NPC57674
0.9467	High Similarity	NPC168247
0.9467	High Similarity	NPC152951
0.9467	High Similarity	NPC255807
0.9467	High Similarity	NPC31018
0.9467	High Similarity	NPC472909
0.9467	High Similarity	NPC117992
0.9467	High Similarity	NPC230149
0.9463	High Similarity	NPC101996
0.9463	High Similarity	NPC71334
0.9463	High Similarity	NPC82325
0.9463	High Similarity	NPC161277
0.9463	High Similarity	NPC241498
0.9463	High Similarity	NPC57030
0.9463	High Similarity	NPC222830
0.9463	High Similarity	NPC60972
0.9463	High Similarity	NPC83508
0.9463	High Similarity	NPC212678
0.9463	High Similarity	NPC100887
0.9463	High Similarity	NPC39732
0.9463	High Similarity	NPC19721
0.9463	High Similarity	NPC120163
0.9463	High Similarity	NPC301323
0.9463	High Similarity	NPC275836
0.9463	High Similarity	NPC198826
0.9463	High Similarity	NPC293183
0.9463	High Similarity	NPC471982
0.9463	High Similarity	NPC162313
0.9463	High Similarity	NPC279989
0.9463	High Similarity	NPC39007
0.9463	High Similarity	NPC131624
0.9463	High Similarity	NPC55205
0.9463	High Similarity	NPC25270
0.9463	High Similarity	NPC188203
0.9463	High Similarity	NPC275722
0.9463	High Similarity	NPC156222
0.9463	High Similarity	NPC239128
0.9463	High Similarity	NPC256283
0.9463	High Similarity	NPC187498
0.9459	High Similarity	NPC61620
0.9459	High Similarity	NPC62042
0.9456	High Similarity	NPC196277
0.9456	High Similarity	NPC203747
0.9456	High Similarity	NPC80710
0.9456	High Similarity	NPC43669
0.9456	High Similarity	NPC272721

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 NPC236637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	926
0.2-0.3	1755
0.3-0.4	2616
0.4-0.5	1743
0.5-0.6	1010
0.6-0.7	538
0.7-0.8	136
0.8-0.85	42
0.85-0.9	12
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1934	Approved
0.9662	High Similarity	NPD2393	Clinical (unspecified phase)
0.94	High Similarity	NPD2801	Approved
0.9355	High Similarity	NPD6167	Clinical (unspecified phase)
0.9355	High Similarity	NPD6166	Phase 2
0.9355	High Similarity	NPD6168	Clinical (unspecified phase)
0.9315	High Similarity	NPD1511	Approved
0.9189	High Similarity	NPD1512	Approved
0.915	High Similarity	NPD3882	Suspended
0.9119	High Similarity	NPD7074	Phase 3
0.9057	High Similarity	NPD7054	Approved
0.9034	High Similarity	NPD1550	Clinical (unspecified phase)
0.9034	High Similarity	NPD1552	Clinical (unspecified phase)
0.9	High Similarity	NPD7472	Approved
0.8994	High Similarity	NPD3818	Discontinued
0.8973	High Similarity	NPD1549	Phase 2
0.8961	High Similarity	NPD3817	Phase 2
0.8903	High Similarity	NPD4868	Clinical (unspecified phase)
0.8827	High Similarity	NPD6797	Phase 2
0.8824	High Similarity	NPD4380	Phase 2
0.8773	High Similarity	NPD7251	Discontinued
0.8742	High Similarity	NPD4378	Clinical (unspecified phase)
0.8734	High Similarity	NPD5494	Approved
0.8726	High Similarity	NPD7075	Discontinued
0.8726	High Similarity	NPD4381	Clinical (unspecified phase)
0.872	High Similarity	NPD4338	Clinical (unspecified phase)
0.872	High Similarity	NPD7808	Phase 3
0.8654	High Similarity	NPD7096	Clinical (unspecified phase)
0.8639	High Similarity	NPD1510	Phase 2
0.8581	High Similarity	NPD2796	Approved
0.8493	Intermediate Similarity	NPD1613	Approved
0.8493	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1240	Approved
0.8481	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD6799	Approved
0.8418	Intermediate Similarity	NPD7819	Suspended
0.8418	Intermediate Similarity	NPD1465	Phase 2
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8378	Intermediate Similarity	NPD1607	Approved
0.8373	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD943	Approved
0.8364	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD5844	Phase 1
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8354	Intermediate Similarity	NPD6801	Discontinued
0.8345	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8291	Intermediate Similarity	NPD7411	Suspended
0.8276	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6599	Discontinued
0.8214	Intermediate Similarity	NPD6559	Discontinued
0.8163	Intermediate Similarity	NPD3027	Phase 3
0.8137	Intermediate Similarity	NPD5402	Approved
0.811	Intermediate Similarity	NPD1247	Approved
0.8105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD919	Approved
0.8067	Intermediate Similarity	NPD230	Phase 1
0.8038	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD5401	Approved
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD3750	Approved
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7964	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD447	Suspended
0.7935	Intermediate Similarity	NPD2800	Approved
0.7927	Intermediate Similarity	NPD3749	Approved
0.7925	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4628	Phase 3
0.7867	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7768	Phase 2
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7829	Intermediate Similarity	NPD1933	Approved
0.7821	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2533	Approved
0.7799	Intermediate Similarity	NPD2534	Approved
0.7799	Intermediate Similarity	NPD2532	Approved
0.7792	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD9494	Approved
0.7784	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.7765	Intermediate Similarity	NPD3751	Discontinued
0.7764	Intermediate Similarity	NPD1653	Approved
0.7742	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD6099	Approved
0.774	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD3748	Approved
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3787	Discontinued
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7616	Intermediate Similarity	NPD4908	Phase 1
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6190	Approved
0.7607	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD1243	Approved
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD37	Approved
0.7564	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7228	Approved
0.7548	Intermediate Similarity	NPD6651	Approved
0.7545	Intermediate Similarity	NPD4966	Approved
0.7545	Intermediate Similarity	NPD4967	Phase 2
0.7545	Intermediate Similarity	NPD4965	Approved
0.7543	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1203	Approved
0.7529	Intermediate Similarity	NPD5953	Discontinued
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7484	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7452	Intermediate Similarity	NPD7033	Discontinued
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.7438	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4363	Phase 3
0.7418	Intermediate Similarity	NPD4360	Phase 2
0.7407	Intermediate Similarity	NPD7390	Discontinued
0.7403	Intermediate Similarity	NPD6798	Discontinued
0.7401	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.7386	Intermediate Similarity	NPD6832	Phase 2
0.7384	Intermediate Similarity	NPD5242	Approved
0.7381	Intermediate Similarity	NPD5353	Approved
0.7337	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD1608	Approved
0.7333	Intermediate Similarity	NPD9269	Phase 2
0.7326	Intermediate Similarity	NPD5711	Approved
0.7326	Intermediate Similarity	NPD5710	Approved
0.732	Intermediate Similarity	NPD2861	Phase 2
0.7305	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD1652	Phase 2
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7263	Intermediate Similarity	NPD7584	Approved
0.7262	Intermediate Similarity	NPD6844	Discontinued
0.7261	Intermediate Similarity	NPD6355	Discontinued
0.7256	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2798	Approved
0.725	Intermediate Similarity	NPD7266	Discontinued
0.7244	Intermediate Similarity	NPD6233	Phase 2
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7226	Intermediate Similarity	NPD4625	Phase 3
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7205	Intermediate Similarity	NPD2424	Discontinued
0.7202	Intermediate Similarity	NPD6386	Approved
0.7202	Intermediate Similarity	NPD6385	Approved
0.719	Intermediate Similarity	NPD2797	Approved
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7186	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8150	Discontinued
0.7179	Intermediate Similarity	NPD411	Approved
0.7171	Intermediate Similarity	NPD4749	Approved
0.7162	Intermediate Similarity	NPD5536	Phase 2
0.716	Intermediate Similarity	NPD2654	Approved
0.7152	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD4661	Approved
0.7152	Intermediate Similarity	NPD4662	Approved
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2403	Approved
0.7135	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD17	Approved
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7124	Intermediate Similarity	NPD3225	Approved
0.7118	Intermediate Similarity	NPD8455	Phase 2
0.7117	Intermediate Similarity	NPD4110	Phase 3
0.7117	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9545	Approved
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7103	Intermediate Similarity	NPD228	Approved
0.7097	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4361	Phase 2
0.7095	Intermediate Similarity	NPD7240	Approved
0.7095	Intermediate Similarity	NPD7039	Approved
0.7095	Intermediate Similarity	NPD7038	Approved
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7089	Intermediate Similarity	NPD4060	Phase 1
0.7083	Intermediate Similarity	NPD7458	Discontinued

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