NPASS Compound

Structure

CID220173 OpenBabel06191716012D 44 48 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 -5.1962 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 39 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 29 1 0 0 0 0 9 1 1 6 0 0 0 9 18 1 0 0 0 0 9 40 1 0 0 0 0 10 24 1 0 0 0 0 11 30 1 0 0 0 0 12 14 2 0 0 0 0 12 31 1 0 0 0 0 13 17 2 0 0 0 0 13 32 1 0 0 0 0 14 39 1 0 0 0 0 15 17 1 0 0 0 0 15 41 1 0 0 0 0 16 8 1 1 0 0 0 16 19 1 0 0 0 0 16 42 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 33 1 1 0 0 0 19 22 1 0 0 0 0 19 34 1 6 0 0 0 20 25 1 0 0 0 0 20 35 2 0 0 0 0 21 23 1 0 0 0 0 21 36 1 6 0 0 0 22 26 1 0 0 0 0 22 37 1 1 0 0 0 23 27 1 0 0 0 0 23 38 1 6 0 0 0 24 25 2 0 0 0 0 24 41 1 0 0 0 0 25 43 1 0 0 0 0 26 28 1 0 0 0 0 26 44 1 6 0 0 0 27 40 1 0 0 0 0 27 44 1 1 0 0 0 28 42 1 0 0 0 0 28 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.17
Volume:	569.614
LogP:	0.301
LogD:	-0.091
LogS:	-3.955
# Rotatable Bonds:	7
TPSA:	258.43
# H-Bond Aceptor:	16
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.147
Synthetic Accessibility Score:	4.744
Fsp3:	0.464
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.423
MDCK Permeability:	2.8670145184150897e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.859
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	82.42789459228516%
Volume Distribution (VD):	0.667
Pgp-substrate:	18.77664566040039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.535
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.813
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.486
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.1
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC220173

Natural Product ID:	NPC220173
*Common Name:**	Isorhamnetin-3-O-Nehesperridin
IUPAC Name:	3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
Synonyms:	Isorhamnetin 3-O-Neohesperidoside
Standard InCHIKey:	QHLKSZBFIJJREC-SPSUIZEHSA-N
Standard InCHI:	InChI=1S/C28H32O16/c1-9-18(33)21(36)23(38)27(40-9)44-26-22(37)19(34)16(8-29)42-28(26)43-25-20(35)17-13(32)6-11(30)7-15(17)41-24(25)10-3-4-12(31)14(5-10)39-2/h3-7,9,16,18-19,21-23,26-34,36-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,26+,27-,28-/m0/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL442566
PubChem CID:	11664505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	roots	Whitessence Srl, Viterbo, Italy	2005-OCT	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21954959]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	DingXi, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	LanZhou, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28251	Typha orientalis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28919	Calendula officinalis	Species	Asteraceae	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
NPO15265	NPC220173	n.a.	Fruits	0.54 ± 0.01	n.a.	n.a.	mg/100g of DW	PMID[33131958]
NPO15265	NPC220173	n.a.	Fruits	0.48 ± 0.03	n.a.	n.a.	mg/100g of DW	PMID[33131958]
NPO15265	NPC220173	n.a.	Fruits	0.28 ± 0.04	n.a.	n.a.	mg/100g of DW	PMID[33131958]
NPO15265	NPC220173	n.a.	Fruits	0.25 ± 0.01	n.a.	n.a.	mg/100g of DW	PMID[33131958]
NPO15265	NPC220173	n.a.	Fruits	0.25 ± 0.03	n.a.	n.a.	mg/100g of DW	PMID[33131958]
NPO15265	NPC220173	n.a.	Fruits	0.24 ± 0.02	n.a.	n.a.	mg/100g of DW	PMID[33131958]
NPO15265	NPC220173	n.a.	Fruits	0.22 ± 0.01	n.a.	n.a.	mg/100g of DW	PMID[33131958]
NPO15265	NPC220173	n.a.	Fruits	0.2 ± 0.04	n.a.	n.a.	mg/100g of DW	PMID[33131958]
NPO15265	NPC220173	n.a.	Fruits	0.19 ± 0.02	n.a.	n.a.	mg/100g of DW	PMID[33131958]
NPO15265	NPC220173	n.a.	Fruits	0.23 ± 0.01	n.a.	n.a.	mg/100g of DW	PMID[33131958]

☑ 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	6
Others	10

Activity Type	# Activity
Cell Line	9
Individual Protein	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[489475]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[489475]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	55.77	%	PMID[489476]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	88.3	%	PMID[489476]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	74400.0	nM	PMID[489477]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	72000.0	nM	PMID[489477]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	>	200.0	ug.mL-1	PMID[489477]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	0.003	ug.mL-1	PMID[489477]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	=	2.47	ug.mL-1	PMID[489477]
NPT2	Others	Unspecified		Activity	=	14.1	%	PMID[489475]
NPT2	Others	Unspecified		Activity	=	60.0	%	PMID[489475]
NPT2	Others	Unspecified		Activity	=	81.1	%	PMID[489475]
NPT2	Others	Unspecified		IC50	=	574.0	molar ratio	PMID[489475]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[489475]

☑ 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 NPC220173 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	460
0.1-0.2	1842
0.2-0.3	4252
0.3-0.4	9791
0.4-0.5	8319
0.5-0.6	4578
0.6-0.7	5577
0.7-0.8	5191
0.8-0.85	1537
0.85-0.9	565
0.9-0.95	424
0.95-1	161

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC16194
1.0	High Similarity	NPC294815
1.0	High Similarity	NPC19108
1.0	High Similarity	NPC476472
1.0	High Similarity	NPC473327
0.9878	High Similarity	NPC251417
0.9878	High Similarity	NPC173837
0.9878	High Similarity	NPC89052
0.9877	High Similarity	NPC471725
0.9877	High Similarity	NPC471748
0.9877	High Similarity	NPC134532
0.9877	High Similarity	NPC33054
0.9877	High Similarity	NPC155877
0.9877	High Similarity	NPC203259
0.9877	High Similarity	NPC26230
0.9877	High Similarity	NPC176740
0.9877	High Similarity	NPC60735
0.9818	High Similarity	NPC473682
0.9818	High Similarity	NPC241423
0.9818	High Similarity	NPC192539
0.9818	High Similarity	NPC473571
0.9818	High Similarity	NPC470443
0.9818	High Similarity	NPC126784
0.9818	High Similarity	NPC470444
0.9818	High Similarity	NPC110941
0.9817	High Similarity	NPC14187
0.9817	High Similarity	NPC48984
0.9817	High Similarity	NPC292019
0.9817	High Similarity	NPC122467
0.9817	High Similarity	NPC202908
0.9817	High Similarity	NPC471669
0.9817	High Similarity	NPC219043
0.9817	High Similarity	NPC89127
0.9815	High Similarity	NPC67105
0.9815	High Similarity	NPC29958
0.9815	High Similarity	NPC136042
0.9815	High Similarity	NPC285197
0.9815	High Similarity	NPC254855
0.9815	High Similarity	NPC259896
0.9815	High Similarity	NPC255157
0.9815	High Similarity	NPC67326
0.9815	High Similarity	NPC95866
0.9815	High Similarity	NPC156869
0.9753	High Similarity	NPC209296
0.9753	High Similarity	NPC195257
0.9753	High Similarity	NPC223747
0.9753	High Similarity	NPC86008
0.9753	High Similarity	NPC225434
0.9753	High Similarity	NPC203050
0.9753	High Similarity	NPC120099
0.9753	High Similarity	NPC219904
0.9753	High Similarity	NPC227508
0.9701	High Similarity	NPC470445
0.9701	High Similarity	NPC470446
0.9701	High Similarity	NPC470447
0.9701	High Similarity	NPC470449
0.9701	High Similarity	NPC473072
0.9697	High Similarity	NPC470949
0.9697	High Similarity	NPC473862
0.9697	High Similarity	NPC65563
0.9697	High Similarity	NPC169733
0.9697	High Similarity	NPC8573
0.9693	High Similarity	NPC206123
0.9691	High Similarity	NPC52550
0.9691	High Similarity	NPC275454
0.9691	High Similarity	NPC226304
0.9691	High Similarity	NPC325555
0.9691	High Similarity	NPC84362
0.9691	High Similarity	NPC223424
0.9691	High Similarity	NPC317489
0.9691	High Similarity	NPC173637
0.9691	High Similarity	NPC265530
0.9691	High Similarity	NPC127546
0.9643	High Similarity	NPC470717
0.9643	High Similarity	NPC21359
0.9643	High Similarity	NPC470451
0.9643	High Similarity	NPC470455
0.9643	High Similarity	NPC460984
0.9643	High Similarity	NPC470713
0.9643	High Similarity	NPC25946
0.9643	High Similarity	NPC470720
0.9643	High Similarity	NPC148710
0.9641	High Similarity	NPC473071
0.9641	High Similarity	NPC473073
0.9636	High Similarity	NPC198199
0.9636	High Similarity	NPC294629
0.9636	High Similarity	NPC253685
0.9634	High Similarity	NPC153755
0.9634	High Similarity	NPC180918
0.9632	High Similarity	NPC270578
0.9632	High Similarity	NPC52382
0.963	High Similarity	NPC210073
0.963	High Similarity	NPC21100
0.963	High Similarity	NPC145038
0.963	High Similarity	NPC73855
0.963	High Similarity	NPC281131
0.963	High Similarity	NPC277174
0.963	High Similarity	NPC253662
0.963	High Similarity	NPC88789
0.963	High Similarity	NPC135599
0.963	High Similarity	NPC308404
0.963	High Similarity	NPC179950
0.963	High Similarity	NPC113968
0.963	High Similarity	NPC197285
0.963	High Similarity	NPC118284
0.963	High Similarity	NPC274618
0.963	High Similarity	NPC8856
0.963	High Similarity	NPC115674
0.963	High Similarity	NPC328940
0.963	High Similarity	NPC276222
0.963	High Similarity	NPC56077
0.9586	High Similarity	NPC295625
0.9586	High Similarity	NPC470719
0.9586	High Similarity	NPC473554
0.9583	High Similarity	NPC241781
0.9583	High Similarity	NPC162394
0.9583	High Similarity	NPC156785
0.9583	High Similarity	NPC470718
0.9576	High Similarity	NPC204693
0.9576	High Similarity	NPC208668
0.9576	High Similarity	NPC42773
0.9576	High Similarity	NPC101026
0.9576	High Similarity	NPC4390
0.9576	High Similarity	NPC21666
0.9576	High Similarity	NPC45522
0.9576	High Similarity	NPC24043
0.9576	High Similarity	NPC169977
0.9573	High Similarity	NPC79056
0.9573	High Similarity	NPC177731
0.9573	High Similarity	NPC244776
0.9573	High Similarity	NPC105095
0.9573	High Similarity	NPC51326
0.9573	High Similarity	NPC116864
0.9573	High Similarity	NPC44328
0.9573	High Similarity	NPC231194
0.9571	High Similarity	NPC160156
0.9571	High Similarity	NPC92565
0.9568	High Similarity	NPC240431
0.9568	High Similarity	NPC55786
0.9568	High Similarity	NPC19388
0.9568	High Similarity	NPC475497
0.9568	High Similarity	NPC277205
0.9568	High Similarity	NPC311830
0.9568	High Similarity	NPC15358
0.9568	High Similarity	NPC284277
0.9568	High Similarity	NPC22832
0.9568	High Similarity	NPC475366
0.9527	High Similarity	NPC249560
0.9527	High Similarity	NPC223860
0.9527	High Similarity	NPC275977
0.9521	High Similarity	NPC120952
0.9521	High Similarity	NPC217520
0.9521	High Similarity	NPC139571
0.9515	High Similarity	NPC190003
0.9515	High Similarity	NPC175107
0.9515	High Similarity	NPC3583
0.9515	High Similarity	NPC476405
0.9515	High Similarity	NPC259152
0.9515	High Similarity	NPC245452
0.9515	High Similarity	NPC117260
0.9515	High Similarity	NPC256760
0.9512	High Similarity	NPC105283
0.9512	High Similarity	NPC293629
0.9512	High Similarity	NPC43587
0.9509	High Similarity	NPC236934
0.9509	High Similarity	NPC5778
0.9506	High Similarity	NPC88023
0.9506	High Similarity	NPC222936
0.9506	High Similarity	NPC270335
0.9506	High Similarity	NPC309025
0.9506	High Similarity	NPC243930
0.9506	High Similarity	NPC284960
0.9506	High Similarity	NPC191306
0.9506	High Similarity	NPC19709
0.9471	High Similarity	NPC104910
0.9471	High Similarity	NPC33083
0.9471	High Similarity	NPC474093
0.9461	High Similarity	NPC255799
0.9461	High Similarity	NPC198324
0.9461	High Similarity	NPC472385
0.9458	High Similarity	NPC25724
0.9455	High Similarity	NPC84265
0.9455	High Similarity	NPC150767
0.9455	High Similarity	NPC78734
0.9455	High Similarity	NPC235260
0.9455	High Similarity	NPC218488
0.9455	High Similarity	NPC20505
0.9455	High Similarity	NPC245014
0.9455	High Similarity	NPC155763
0.9455	High Similarity	NPC282987
0.9451	High Similarity	NPC229729
0.9444	High Similarity	NPC473043
0.9444	High Similarity	NPC240306
0.9444	High Similarity	NPC77660
0.9444	High Similarity	NPC189142
0.9415	High Similarity	NPC30011
0.9415	High Similarity	NPC97817
0.9415	High Similarity	NPC475179
0.9415	High Similarity	NPC64755
0.9415	High Similarity	NPC72554

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 NPC220173 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	953
0.2-0.3	1998
0.3-0.4	2741
0.4-0.5	1793
0.5-0.6	852
0.6-0.7	273
0.7-0.8	104
0.8-0.85	18
0.85-0.9	6
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9938	High Similarity	NPD7251	Discontinued
0.9877	High Similarity	NPD7808	Phase 3
0.9877	High Similarity	NPD6797	Phase 2
0.9815	High Similarity	NPD7472	Approved
0.9753	High Similarity	NPD7054	Approved
0.9573	High Similarity	NPD7074	Phase 3
0.9401	High Similarity	NPD4338	Clinical (unspecified phase)
0.9277	High Similarity	NPD7804	Clinical (unspecified phase)
0.9212	High Similarity	NPD6167	Clinical (unspecified phase)
0.9212	High Similarity	NPD6168	Clinical (unspecified phase)
0.9212	High Similarity	NPD6166	Phase 2
0.9102	High Similarity	NPD3818	Discontinued
0.8963	High Similarity	NPD4381	Clinical (unspecified phase)
0.8841	High Similarity	NPD3817	Phase 2
0.8834	High Similarity	NPD1934	Approved
0.8675	High Similarity	NPD3882	Suspended
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD2801	Approved
0.858	High Similarity	NPD1512	Approved
0.8512	High Similarity	NPD7075	Discontinued
0.8506	High Similarity	NPD7993	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD1511	Approved
0.8373	Intermediate Similarity	NPD4380	Phase 2
0.8343	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD5402	Approved
0.8274	Intermediate Similarity	NPD6801	Discontinued
0.8249	Intermediate Similarity	NPD6559	Discontinued
0.8193	Intermediate Similarity	NPD5403	Approved
0.8182	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8142	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6799	Approved
0.8092	Intermediate Similarity	NPD5494	Approved
0.8072	Intermediate Similarity	NPD5401	Approved
0.8036	Intermediate Similarity	NPD1653	Approved
0.8023	Intermediate Similarity	NPD3751	Discontinued
0.8023	Intermediate Similarity	NPD7228	Approved
0.8	Intermediate Similarity	NPD3787	Discontinued
0.7975	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD8312	Approved
0.7956	Intermediate Similarity	NPD8313	Approved
0.7944	Intermediate Similarity	NPD7685	Pre-registration
0.7943	Intermediate Similarity	NPD6959	Discontinued
0.7927	Intermediate Similarity	NPD1549	Phase 2
0.7907	Intermediate Similarity	NPD7819	Suspended
0.7907	Intermediate Similarity	NPD1465	Phase 2
0.7877	Intermediate Similarity	NPD5844	Phase 1
0.7865	Intermediate Similarity	NPD7473	Discontinued
0.7853	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6599	Discontinued
0.7805	Intermediate Similarity	NPD2796	Approved
0.7797	Intermediate Similarity	NPD6232	Discontinued
0.7791	Intermediate Similarity	NPD7411	Suspended
0.7772	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7266	Discontinued
0.7751	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1510	Phase 2
0.7742	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7199	Phase 2
0.7727	Intermediate Similarity	NPD919	Approved
0.772	Intermediate Similarity	NPD7435	Discontinued
0.7704	Intermediate Similarity	NPD8151	Discontinued
0.7701	Intermediate Similarity	NPD8455	Phase 2
0.7656	Intermediate Similarity	NPD6779	Approved
0.7656	Intermediate Similarity	NPD6776	Approved
0.7656	Intermediate Similarity	NPD6781	Approved
0.7656	Intermediate Similarity	NPD6782	Approved
0.7656	Intermediate Similarity	NPD6780	Approved
0.7656	Intermediate Similarity	NPD6778	Approved
0.7656	Intermediate Similarity	NPD6777	Approved
0.765	Intermediate Similarity	NPD7240	Approved
0.764	Intermediate Similarity	NPD1247	Approved
0.7629	Intermediate Similarity	NPD7698	Approved
0.7629	Intermediate Similarity	NPD7697	Approved
0.7629	Intermediate Similarity	NPD7696	Phase 3
0.7627	Intermediate Similarity	NPD6234	Discontinued
0.7611	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1613	Approved
0.7607	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7584	Approved
0.7574	Intermediate Similarity	NPD6190	Approved
0.7563	Intermediate Similarity	NPD7701	Phase 2
0.7556	Intermediate Similarity	NPD3926	Phase 2
0.7543	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4967	Phase 2
0.7514	Intermediate Similarity	NPD4966	Approved
0.7514	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7874	Approved
0.7487	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7700	Phase 2
0.7461	Intermediate Similarity	NPD7699	Phase 2
0.7455	Intermediate Similarity	NPD1933	Approved
0.745	Intermediate Similarity	NPD7783	Phase 2
0.745	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3027	Phase 3
0.7416	Intermediate Similarity	NPD7768	Phase 2
0.7412	Intermediate Similarity	NPD3750	Approved
0.7411	Intermediate Similarity	NPD8320	Phase 1
0.7411	Intermediate Similarity	NPD8319	Approved
0.741	Intermediate Similarity	NPD1607	Approved
0.7396	Intermediate Similarity	NPD6535	Approved
0.7396	Intermediate Similarity	NPD6534	Approved
0.7394	Intermediate Similarity	NPD943	Approved
0.7378	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7801	Approved
0.7362	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD230	Phase 1
0.731	Intermediate Similarity	NPD4628	Phase 3
0.731	Intermediate Similarity	NPD6823	Phase 2
0.7301	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1551	Phase 2
0.7278	Intermediate Similarity	NPD3749	Approved
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7246	Intermediate Similarity	NPD447	Suspended
0.7245	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7585	Approved
0.7208	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7680	Approved
0.7176	Intermediate Similarity	NPD2935	Discontinued
0.7175	Intermediate Similarity	NPD7458	Discontinued
0.7164	Intermediate Similarity	NPD7583	Approved
0.7151	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6674	Discontinued
0.7143	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7129	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3748	Approved
0.7076	Intermediate Similarity	NPD6100	Approved
0.7076	Intermediate Similarity	NPD6099	Approved
0.7066	Intermediate Similarity	NPD6798	Discontinued
0.7062	Intermediate Similarity	NPD920	Approved
0.7056	Intermediate Similarity	NPD6844	Discontinued
0.7053	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2800	Approved
0.7048	Intermediate Similarity	NPD6832	Phase 2
0.7045	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4360	Phase 2
0.7041	Intermediate Similarity	NPD6355	Discontinued
0.7041	Intermediate Similarity	NPD4363	Phase 3
0.7037	Intermediate Similarity	NPD1091	Approved
0.7037	Intermediate Similarity	NPD5953	Discontinued
0.7024	Intermediate Similarity	NPD6233	Phase 2
0.7021	Intermediate Similarity	NPD7286	Phase 2
0.7018	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD6651	Approved
0.699	Remote Similarity	NPD6212	Phase 3
0.699	Remote Similarity	NPD6213	Phase 3
0.699	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7390	Discontinued
0.6988	Remote Similarity	NPD9494	Approved
0.6983	Remote Similarity	NPD3226	Approved
0.6978	Remote Similarity	NPD5353	Approved
0.6954	Remote Similarity	NPD1652	Phase 2
0.6954	Remote Similarity	NPD1243	Approved
0.6951	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4908	Phase 1
0.6932	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2798	Approved
0.6914	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8127	Discontinued
0.6878	Remote Similarity	NPD2163	Approved
0.6872	Remote Similarity	NPD6842	Approved
0.6872	Remote Similarity	NPD6841	Approved
0.6872	Remote Similarity	NPD6843	Phase 3
0.6867	Remote Similarity	NPD1203	Approved
0.6864	Remote Similarity	NPD2313	Discontinued
0.6864	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7930	Approved
0.6842	Remote Similarity	NPD5124	Phase 1
0.6839	Remote Similarity	NPD2346	Discontinued
0.6839	Remote Similarity	NPD2344	Approved
0.6829	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2799	Discontinued
0.6813	Remote Similarity	NPD6386	Approved
0.6813	Remote Similarity	NPD6385	Approved
0.6813	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5242	Approved
0.6808	Remote Similarity	NPD7907	Approved
0.6804	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5006	Approved
0.6798	Remote Similarity	NPD5005	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