NPASS Compound

Structure

CID241949 OpenBabel06191716042D 29 28 0 0 1 0 0 0 0 0999 V2000 12.8958 -0.1294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8958 0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0597 1.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2235 0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3874 1.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5512 0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7150 1.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8789 0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0427 1.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2065 0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3704 1.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5342 0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6981 1.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8619 0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0257 1.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1896 0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9655 1.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3534 1.3189 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.8966 1.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3534 2.2844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3189 0.3534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4828 0.8362 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3793 2.5085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3793 0.8362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1896 2.7672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4828 2.7672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1551 0.8362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3189 -0.6121 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.28
Volume:	442.69
LogP:	5.733
LogD:	3.234
LogS:	-3.522
# Rotatable Bonds:	20
TPSA:	132.13
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	0
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	3.203
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.798
MDCK Permeability:	6.167093670228496e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.246
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	98.8748550415039%
Volume Distribution (VD):	0.444
Pgp-substrate:	0.9282556176185608%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.924
Half-life (T1/2):	0.625

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.17
Carcinogencity:	0.036
Eye Corrosion:	0.978
Eye Irritation:	0.943
Respiratory Toxicity:	0.165

Download Data

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

Natural Product: NPC241949

Natural Product ID:	NPC241949
*Common Name:**	2-Hydroxynonadecane-1,2,3-Tricarboxylic Acid
IUPAC Name:	2-hydroxynonadecane-1,2,3-tricarboxylic acid
Synonyms:
Standard InCHIKey:	HZLCGUXUOFWCCN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H40O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18(20(25)26)22(29,21(27)28)17-19(23)24/h18,29H,2-17H2,1H3,(H,23,24)(H,25,26)(H,27,28)
SMILES:	CCCCCCCCCCCCCCCCC(C(C(=O)O)(CC(=O)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL78764
PubChem CID:	12629
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165144]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844878]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209522]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17279797]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20583752]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	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
AC50	3
GI50	54
IC50	15
Others	12
Potency	44

Activity Type	# Activity
Cell Line	55
Individual Protein	14
Organism	1
Others	50
PROTEIN COMPLEX	10
SINGLE PROTEIN	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1664	Individual Protein	Squalene synthetase	Rattus norvegicus	IC50	=	9000.0	nM	PMID[478998]
NPT58	Individual Protein	Bloom syndrome protein	Homo sapiens	Potency	=	39810.7	nM	PMID[478999]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	1122.0	nM	PMID[478999]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	36.0	%	PMID[479000]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[478999]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[478999]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[478999]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	21677.04	nM	PMID[479001]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	46989.41	nM	PMID[479001]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	40644.33	nM	PMID[479001]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	28973.44	nM	PMID[479001]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	20323.57	nM	PMID[479001]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	35645.11	nM	PMID[479001]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	14825.18	nM	PMID[479001]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	39084.09	nM	PMID[479001]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	28119.01	nM	PMID[479001]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	58613.82	nM	PMID[479001]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	21037.78	nM	PMID[479001]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	35237.09	nM	PMID[479001]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	18535.32	nM	PMID[479001]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	25527.01	nM	PMID[479001]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	57016.43	nM	PMID[479001]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	17218.69	nM	PMID[479001]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	16672.47	nM	PMID[479001]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	39084.09	nM	PMID[479001]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	17947.34	nM	PMID[479001]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	27542.29	nM	PMID[479001]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	23878.11	nM	PMID[479001]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	24717.24	nM	PMID[479001]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	34753.62	nM	PMID[479001]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	19998.62	nM	PMID[479001]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	21232.44	nM	PMID[479001]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	19678.86	nM	PMID[479001]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	19319.68	nM	PMID[479001]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	26730.06	nM	PMID[479001]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	26485.0	nM	PMID[479001]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	20276.83	nM	PMID[479001]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	18879.91	nM	PMID[479001]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	19998.62	nM	PMID[479001]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	21478.3	nM	PMID[479001]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	19142.56	nM	PMID[479001]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	28641.78	nM	PMID[479001]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	20183.66	nM	PMID[479001]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	19543.39	nM	PMID[479001]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	34914.03	nM	PMID[479001]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	17701.09	nM	PMID[479001]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	17538.81	nM	PMID[479001]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	21428.91	nM	PMID[479001]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	18197.01	nM	PMID[479001]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	34833.73	nM	PMID[479001]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	17660.38	nM	PMID[479001]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	22080.05	nM	PMID[479001]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	32196.8	nM	PMID[478999]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	35156.04	nM	PMID[479001]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	24099.05	nM	PMID[479001]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	34119.29	nM	PMID[479001]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	27101.92	nM	PMID[479001]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	21232.44	nM	PMID[479001]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	22646.44	nM	PMID[479001]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	22080.05	nM	PMID[479001]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	23933.16	nM	PMID[479001]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	18706.82	nM	PMID[479001]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29855.4	nM	PMID[478999]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[478999]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	18832.2	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	26832.5	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	26601.1	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	26832.5	nM	PubChem BioAssay data set
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	0.0	%	PMID[478998]
NPT2	Others	Unspecified		Potency	n.a.	0.3	nM	PMID[478999]
NPT2	Others	Unspecified		Potency	n.a.	0.3	nM	PMID[479002]
NPT2	Others	Unspecified		AC50	n.a.	25118.9	nM	PMID[479003]
NPT2	Others	Unspecified		IC50	=	4099.6	nM	PMID[479003]
NPT2	Others	Unspecified		IC50	=	4283.2	nM	PMID[479003]
NPT2	Others	Unspecified		IC50	=	4338.2	nM	PMID[479003]
NPT2	Others	Unspecified		Ac50	n.a.	8.913	uM	PMID[479003]
NPT2	Others	Unspecified		IC50	=	8684.7	nM	PMID[479003]
NPT2	Others	Unspecified		IC50	=	1195.2	nM	PMID[479003]
NPT2	Others	Unspecified		IC50	=	1361.3	nM	PMID[479003]
NPT2	Others	Unspecified		Ac50	n.a.	25.12	uM	PMID[479003]
NPT2	Others	Unspecified		IC50	=	3482.2	nM	PMID[479003]
NPT2	Others	Unspecified		IC50	=	1362.1	nM	PMID[479003]
NPT2	Others	Unspecified		Ac50	n.a.	5.012	uM	PMID[479003]
NPT2	Others	Unspecified		AC50	n.a.	8912.5	nM	PMID[479003]
NPT2	Others	Unspecified		AC50	n.a.	5011.9	nM	PMID[479003]
NPT23878	SINGLE PROTEIN	Translin-associated protein X	Homo sapiens	Inhibition	=	58.0	%	PMID[479004]
NPT21773	SINGLE PROTEIN	Thiosulfate sulfurtransferase	Homo sapiens	IC50	>	100000.0	nM	PMID[479005]
NPT2	Others	Unspecified		IC50	>	63000.0	nM	PMID[479005]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	IC50	=	8900.0	nM	PMID[479005]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	IC50	=	3500.0	nM	PMID[479005]
NPT21774	PROTEIN COMPLEX	HSP60/HSP10	Homo sapiens	IC50	=	4000.0	nM	PMID[479005]
NPT21775	SINGLE PROTEIN	60 kDa chaperonin	Escherichia coli (strain K12)	IC50	>	250000.0	nM	PMID[479005]
NPT2	Others	Unspecified		Ratio IC50	>	10.0	n.a.	PMID[479005]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	100.0	%	PMID[479005]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	99.0	%	PMID[479005]
NPT2	Others	Unspecified		Potency	n.a.	13332.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10682.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	26832.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	26603.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	18832.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	16930.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1188.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	23708.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	33488.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21130	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	26601.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	29849.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	29847	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	16930.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	18995.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21313.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	23914.5	nM	PubChem BioAssay data set

☑ 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 NPC241949 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	574
0.1-0.2	4891
0.2-0.3	14269
0.3-0.4	12720
0.4-0.5	8434
0.5-0.6	1686
0.6-0.7	99
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8033	Intermediate Similarity	NPC72722
0.7612	Intermediate Similarity	NPC469923
0.7571	Intermediate Similarity	NPC469925
0.75	Intermediate Similarity	NPC474552
0.7463	Intermediate Similarity	NPC469921
0.7377	Intermediate Similarity	NPC293378
0.7313	Intermediate Similarity	NPC475821
0.7313	Intermediate Similarity	NPC469924
0.7286	Intermediate Similarity	NPC476330
0.7231	Intermediate Similarity	NPC68743
0.7231	Intermediate Similarity	NPC60830
0.7213	Intermediate Similarity	NPC477878
0.7213	Intermediate Similarity	NPC324793
0.7188	Intermediate Similarity	NPC65985
0.7164	Intermediate Similarity	NPC179624
0.7143	Intermediate Similarity	NPC474003
0.7121	Intermediate Similarity	NPC198377
0.7083	Intermediate Similarity	NPC286842
0.7059	Intermediate Similarity	NPC472020
0.7059	Intermediate Similarity	NPC226602
0.7059	Intermediate Similarity	NPC472019
0.7059	Intermediate Similarity	NPC470363
0.7049	Intermediate Similarity	NPC21844
0.6986	Remote Similarity	NPC319007
0.6986	Remote Similarity	NPC82315
0.6974	Remote Similarity	NPC317212
0.6957	Remote Similarity	NPC472021
0.6923	Remote Similarity	NPC19676
0.6923	Remote Similarity	NPC323401
0.6885	Remote Similarity	NPC314679
0.6883	Remote Similarity	NPC228411
0.6857	Remote Similarity	NPC469922
0.6842	Remote Similarity	NPC473699
0.6842	Remote Similarity	NPC475232
0.6842	Remote Similarity	NPC474100
0.6842	Remote Similarity	NPC51249
0.6842	Remote Similarity	NPC473775
0.6842	Remote Similarity	NPC475260
0.6818	Remote Similarity	NPC6883
0.6806	Remote Similarity	NPC215987
0.6806	Remote Similarity	NPC469926
0.6806	Remote Similarity	NPC306805
0.6761	Remote Similarity	NPC235788
0.6721	Remote Similarity	NPC55023
0.6711	Remote Similarity	NPC96322
0.6709	Remote Similarity	NPC108014
0.6667	Remote Similarity	NPC28526
0.6667	Remote Similarity	NPC65359
0.6667	Remote Similarity	NPC314103
0.6628	Remote Similarity	NPC53158
0.6625	Remote Similarity	NPC475616
0.6625	Remote Similarity	NPC470014
0.6591	Remote Similarity	NPC469627
0.6588	Remote Similarity	NPC476717
0.6582	Remote Similarity	NPC474020
0.6575	Remote Similarity	NPC469791
0.6556	Remote Similarity	NPC470191
0.6556	Remote Similarity	NPC475900
0.6533	Remote Similarity	NPC470956
0.65	Remote Similarity	NPC83108
0.65	Remote Similarity	NPC122847
0.65	Remote Similarity	NPC214030
0.65	Remote Similarity	NPC469867
0.6462	Remote Similarity	NPC90904
0.6456	Remote Similarity	NPC179922
0.6444	Remote Similarity	NPC309127
0.6444	Remote Similarity	NPC247877
0.642	Remote Similarity	NPC476986
0.642	Remote Similarity	NPC470905
0.64	Remote Similarity	NPC53879
0.64	Remote Similarity	NPC57788
0.6393	Remote Similarity	NPC310220
0.6375	Remote Similarity	NPC469514
0.6374	Remote Similarity	NPC322188
0.6364	Remote Similarity	NPC477443
0.6364	Remote Similarity	NPC470268
0.6364	Remote Similarity	NPC477440
0.6351	Remote Similarity	NPC230047
0.6351	Remote Similarity	NPC19311
0.6344	Remote Similarity	NPC274695
0.6341	Remote Similarity	NPC19841
0.6338	Remote Similarity	NPC17935
0.6333	Remote Similarity	NPC475788
0.6329	Remote Similarity	NPC215030
0.6324	Remote Similarity	NPC469937
0.6324	Remote Similarity	NPC320588
0.6324	Remote Similarity	NPC53463
0.6324	Remote Similarity	NPC319589
0.6324	Remote Similarity	NPC23155
0.6322	Remote Similarity	NPC314364
0.631	Remote Similarity	NPC477936
0.631	Remote Similarity	NPC477935
0.6308	Remote Similarity	NPC476469
0.6304	Remote Similarity	NPC39859
0.6304	Remote Similarity	NPC476009
0.6304	Remote Similarity	NPC158416
0.6304	Remote Similarity	NPC470883
0.6304	Remote Similarity	NPC76862
0.6296	Remote Similarity	NPC169389
0.6296	Remote Similarity	NPC281296
0.6296	Remote Similarity	NPC120776
0.6296	Remote Similarity	NPC240170
0.6292	Remote Similarity	NPC316228
0.6292	Remote Similarity	NPC263977
0.6292	Remote Similarity	NPC477442
0.6292	Remote Similarity	NPC477444
0.6292	Remote Similarity	NPC477433
0.629	Remote Similarity	NPC74845
0.6286	Remote Similarity	NPC61567
0.6282	Remote Similarity	NPC311102
0.6282	Remote Similarity	NPC472309
0.6282	Remote Similarity	NPC470243
0.6279	Remote Similarity	NPC476715
0.6279	Remote Similarity	NPC51267
0.6279	Remote Similarity	NPC131350
0.6269	Remote Similarity	NPC277878
0.6264	Remote Similarity	NPC206878
0.625	Remote Similarity	NPC217725
0.625	Remote Similarity	NPC132064
0.625	Remote Similarity	NPC471221
0.625	Remote Similarity	NPC201046
0.6237	Remote Similarity	NPC278028
0.6237	Remote Similarity	NPC328180
0.6234	Remote Similarity	NPC98711
0.623	Remote Similarity	NPC149184
0.623	Remote Similarity	NPC216630
0.623	Remote Similarity	NPC248763
0.623	Remote Similarity	NPC307783
0.623	Remote Similarity	NPC209970
0.623	Remote Similarity	NPC196924
0.623	Remote Similarity	NPC171736
0.623	Remote Similarity	NPC325452
0.6222	Remote Similarity	NPC327515
0.622	Remote Similarity	NPC218817
0.622	Remote Similarity	NPC121200
0.622	Remote Similarity	NPC11796
0.6216	Remote Similarity	NPC53642
0.6216	Remote Similarity	NPC470325
0.6207	Remote Similarity	NPC475491
0.6207	Remote Similarity	NPC92139
0.6207	Remote Similarity	NPC120395
0.6207	Remote Similarity	NPC469626
0.6196	Remote Similarity	NPC287354
0.6196	Remote Similarity	NPC62407
0.6184	Remote Similarity	NPC41542
0.618	Remote Similarity	NPC56962
0.618	Remote Similarity	NPC24705
0.6176	Remote Similarity	NPC196612
0.6163	Remote Similarity	NPC79308
0.6163	Remote Similarity	NPC477434
0.6163	Remote Similarity	NPC473791
0.6163	Remote Similarity	NPC115995
0.6154	Remote Similarity	NPC131770
0.6154	Remote Similarity	NPC200618
0.6145	Remote Similarity	NPC82488
0.6145	Remote Similarity	NPC308545
0.6136	Remote Similarity	NPC51662
0.6136	Remote Similarity	NPC197333
0.6129	Remote Similarity	NPC67462
0.6129	Remote Similarity	NPC469528
0.6129	Remote Similarity	NPC469369
0.6129	Remote Similarity	NPC31645
0.6125	Remote Similarity	NPC125164
0.6125	Remote Similarity	NPC477930
0.6125	Remote Similarity	NPC477867
0.6122	Remote Similarity	NPC469441
0.6122	Remote Similarity	NPC228311
0.6122	Remote Similarity	NPC41674
0.6118	Remote Similarity	NPC474605
0.6118	Remote Similarity	NPC476292
0.6118	Remote Similarity	NPC475395
0.6118	Remote Similarity	NPC476984
0.6104	Remote Similarity	NPC476629
0.6098	Remote Similarity	NPC477918
0.6098	Remote Similarity	NPC477919
0.6098	Remote Similarity	NPC112463
0.6098	Remote Similarity	NPC180199
0.6092	Remote Similarity	NPC477445
0.6092	Remote Similarity	NPC478111
0.6082	Remote Similarity	NPC475873
0.6076	Remote Similarity	NPC478227
0.6071	Remote Similarity	NPC103634
0.6067	Remote Similarity	NPC269677
0.6067	Remote Similarity	NPC315911
0.6066	Remote Similarity	NPC240109
0.6064	Remote Similarity	NPC474313
0.6064	Remote Similarity	NPC470632
0.6064	Remote Similarity	NPC323421
0.6064	Remote Similarity	NPC74466
0.6064	Remote Similarity	NPC328562
0.6061	Remote Similarity	NPC469787
0.6061	Remote Similarity	NPC469788
0.6061	Remote Similarity	NPC290247
0.6049	Remote Similarity	NPC179858
0.6049	Remote Similarity	NPC477934
0.6049	Remote Similarity	NPC155441
0.6049	Remote Similarity	NPC199445
0.6047	Remote Similarity	NPC476721
0.6047	Remote Similarity	NPC320936
0.6047	Remote Similarity	NPC472847

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 NPC241949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	896
0.1-0.2	4325
0.2-0.3	2510
0.3-0.4	913
0.4-0.5	376
0.5-0.6	97
0.6-0.7	20
0.7-0.8	13
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
0.7391	Intermediate Similarity	NPD7909	Approved
0.7377	Intermediate Similarity	NPD9126	Approved
0.7377	Intermediate Similarity	NPD71	Approved
0.7377	Intermediate Similarity	NPD9129	Approved
0.7213	Intermediate Similarity	NPD9124	Approved
0.7213	Intermediate Similarity	NPD9123	Approved
0.7213	Intermediate Similarity	NPD9125	Approved
0.7213	Intermediate Similarity	NPD9128	Approved
0.7213	Intermediate Similarity	NPD9122	Approved
0.7213	Intermediate Similarity	NPD109	Approved
0.7213	Intermediate Similarity	NPD9121	Approved
0.7213	Intermediate Similarity	NPD9130	Phase 3
0.7213	Intermediate Similarity	NPD9127	Approved
0.7213	Intermediate Similarity	NPD108	Approved
0.7213	Intermediate Similarity	NPD70	Approved
0.6885	Remote Similarity	NPD634	Phase 3
0.6818	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3186	Phase 1
0.6618	Remote Similarity	NPD73	Approved
0.6571	Remote Similarity	NPD3198	Approved
0.6567	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9638	Phase 2
0.6324	Remote Similarity	NPD3728	Approved
0.6324	Remote Similarity	NPD3730	Approved
0.6269	Remote Similarity	NPD9008	Approved
0.6269	Remote Similarity	NPD9010	Approved
0.6269	Remote Similarity	NPD64	Approved
0.6269	Remote Similarity	NPD72	Approved
0.6269	Remote Similarity	NPD9011	Approved
0.6269	Remote Similarity	NPD65	Approved
0.6269	Remote Similarity	NPD66	Approved
0.6269	Remote Similarity	NPD9009	Approved
0.6269	Remote Similarity	NPD9007	Approved
0.6269	Remote Similarity	NPD8960	Approved
0.623	Remote Similarity	NPD2270	Approved
0.622	Remote Similarity	NPD4802	Phase 2
0.622	Remote Similarity	NPD4238	Approved
0.6076	Remote Similarity	NPD6081	Approved
0.602	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5369	Approved
0.5938	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD77	Approved
0.5902	Remote Similarity	NPD9448	Phase 2
0.5902	Remote Similarity	NPD633	Phase 3
0.5902	Remote Similarity	NPD9655	Approved
0.5902	Remote Similarity	NPD9450	Approved
0.5897	Remote Similarity	NPD229	Approved
0.5882	Remote Similarity	NPD5368	Approved
0.5873	Remote Similarity	NPD387	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7983	Approved
0.5844	Remote Similarity	NPD4224	Phase 2
0.5843	Remote Similarity	NPD5786	Approved
0.5842	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8959	Approved
0.5747	Remote Similarity	NPD4270	Approved
0.5747	Remote Similarity	NPD6435	Approved
0.5747	Remote Similarity	NPD4269	Approved
0.5747	Remote Similarity	NPD7345	Approved
0.5743	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD3206	Approved
0.5714	Remote Similarity	NPD7341	Phase 2
0.5714	Remote Similarity	NPD1700	Approved
0.5714	Remote Similarity	NPD6116	Phase 1
0.5672	Remote Similarity	NPD9005	Phase 3
0.5672	Remote Similarity	NPD9003	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD9004	Approved
0.5672	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD3702	Approved
0.5657	Remote Similarity	NPD8085	Approved
0.5657	Remote Similarity	NPD8084	Approved
0.5657	Remote Similarity	NPD8082	Approved
0.5657	Remote Similarity	NPD8086	Approved
0.5657	Remote Similarity	NPD8138	Approved
0.5657	Remote Similarity	NPD8139	Approved
0.5657	Remote Similarity	NPD8083	Approved
0.5652	Remote Similarity	NPD9001	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD9002	Approved
0.5647	Remote Similarity	NPD6114	Approved
0.5647	Remote Similarity	NPD6697	Approved
0.5647	Remote Similarity	NPD6118	Approved
0.5647	Remote Similarity	NPD6115	Approved
0.5644	Remote Similarity	NPD8393	Approved
0.56	Remote Similarity	NPD8276	Approved
0.56	Remote Similarity	NPD8275	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