NPASS Compound

Natural Product: NPC29771

Natural Product ID	NPC29771
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dimethylacrylshikonin
IUPAC Name	[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate
Synonyms	Dimethylacrylshikonin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL267024
PubChem CID	479499
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 49 50 0 0 0 0 0 0 0 0999 V2000 -1.1571 3.2347 1.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8869 3.4172 -0.3723 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1448 2.8739 -0.9720 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1662 2.0194 -0.3076 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1804 0.6776 -1.0092 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1483 0.0218 -0.9208 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8367 -0.2524 -2.0241 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1284 -0.8911 -1.9125 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8127 -1.1674 -2.9473 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7290 -1.2580 -0.6299 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9460 -1.8589 -0.5398 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4622 -2.1820 0.7007 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7461 -1.8955 1.8270 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5006 -1.2803 1.7307 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0145 -0.9725 0.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7198 -0.3314 0.3710 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0834 -0.0790 1.4045 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7883 -0.9970 2.8819 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6787 -2.1532 -1.6726 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1504 -0.1875 -0.4535 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1776 -0.6676 -1.2477 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2094 -0.3100 -2.4534 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2101 -1.5618 -0.7410 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2438 -1.9806 0.5111 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2110 -1.5546 1.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3092 -2.8923 0.9988 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8482 4.2579 -1.1496 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2210 3.3514 1.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8913 4.0002 1.4377 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5837 2.2523 1.3188 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2732 3.0598 -2.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8916 1.9273 0.7579 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1607 2.5326 -0.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4214 0.8454 -2.0853 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4380 -0.0031 -2.9755 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4188 -2.6540 0.7654 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1393 -2.1433 2.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9882 -1.5475 3.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0437 -1.3721 -2.2289 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9909 -1.9086 -1.4023 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1928 -1.8603 1.1720 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2774 -0.4383 1.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4115 -1.9547 2.5035 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0342 -3.9648 0.8903 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2468 -2.7090 0.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5435 -2.7422 2.0741 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6747 3.5964 -1.5240 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3274 4.6247 -2.0512 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2338 5.0781 -0.5352 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 14 18 1 0 11 19 1 0 5 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 3 24 25 1 0 24 26 1 0 2 27 1 0 16 6 1 0 15 10 1 0 1 28 1 0 1 29 1 0 1 30 1 0 3 31 1 0 4 32 1 0 4 33 1 0 5 34 1 6 7 35 1 0 12 36 1 0 13 37 1 0 18 38 1 0 19 39 1 0 23 40 1 0 25 41 1 0 25 42 1 0 25 43 1 0 26 44 1 0 26 45 1 0 26 46 1 0 27 47 1 0 27 48 1 0 27 49 1 0 M END

Standard InCHIKey	BATBOVZTQBLKIL-QGZVFWFLSA-N
Standard InCHI	InChI=1S/C21H22O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,9-10,17,22-23H,8H2,1-4H3/t17-/m1/s1
SMILES	CC(=CC[C@H](C1=CC(=O)c2c(ccc(c2C1=O)O)O)OC(=O)C=C(C)C)C

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s11418-007-0221-0]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(83)80138-1]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502328]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17157006]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17488128]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19217780]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19534474]
NPO17855	Onosma paniculata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22530779]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3373224]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7775984]
NPO17855	Onosma paniculata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9209	Rhizomnium magnifolium	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11300	Eucalyptus coccifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30958	Onosma paniculatum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17855	Onosma paniculata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30958	Onosma paniculatum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17855	Onosma paniculata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11300	Eucalyptus coccifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9209	Rhizomnium magnifolium	Species	Mniaceae	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	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	35
Inhibition	4
Ki	1
Ratio IC50	1
Activity	49
FC	4

Activity Type	# Activity
Individual protein	4
Cell line	76
Unchecked	1
Others	7
Non-molecular	4
Organism	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	IC50	=	77000.0	nM	PMID[7699697]
NPT2228	Individual protein	Neuraminidase	Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1))	IC50	=	47300.0	nM	PMID[22300884]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	6.03	%	PMID[23062825]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	22.84	%	PMID[23062825]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	=	1900.0	nM	PMID[22530779]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	23200.0	nM	PMID[22530779]
NPT380	Cell line	U-251	Homo sapiens	IC50	=	30800.0	nM	PMID[22530779]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	20000.0	nM	PMID[22530779]
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	2400.0	nM	PMID[22530779]
NPT171	Cell line	MRC5	Homo sapiens	Ratio IC50	=	6.0	n.a.	PMID[22530779]
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	414.8	%	PMID[25127868]
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	9500.0	nM	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	IC50	=	5100.0	nM	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	IC50	=	2300.0	nM	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	IC50	=	1700.0	nM	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	IC50	=	1200.0	nM	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	IC50	=	800.0	nM	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	IC50	=	700.0	nM	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	Activity	=	75.52	%	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	Activity	=	10.56	%	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	Activity	=	13.53	%	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	Activity	=	0.39	%	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	Activity	=	88.54	%	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	Activity	=	8.45	%	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	Activity	=	5.72	%	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	Activity	=	0.3	%	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	Activity	=	45.04	%	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	Activity	=	10.92	%	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	Activity	=	43.89	%	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	Activity	=	0.16	%	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	Activity	=	83.29	%	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	Activity	=	13.71	%	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	Activity	=	2.78	%	PMID[31961147]
NPT22994	Cell line	WM793	Homo sapiens	Activity	=	0.22	%	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	FC	=	6.0	n.a.	PMID[31961147]
NPT22993	Cell line	MUGMel2	Homo sapiens	IC50	=	7200.0	nM	PMID[35367708]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	2700.0	nM	PMID[35367708]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1100.0	nM	PMID[22530779]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2300.0	nM	PMID[22530779]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2700.0	nM	PMID[22530779]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	8300.0	nM	PMID[22530779]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	50.0	%	PMID[22530779]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	20.0	%	PMID[22530779]
NPT22991	Cell line	WM164	Homo sapiens	IC50	=	3800.0	nM	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	IC50	=	3000.0	nM	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	IC50	=	2400.0	nM	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	88.63	%	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	2.47	%	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	8.65	%	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	0.24	%	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	75.03	%	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	12.85	%	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	11.6	%	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	0.52	%	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	FC	=	1.6	n.a.	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	Activity	=	60.0	%	PMID[31961147]
NPT22991	Cell line	WM164	Homo sapiens	IC50	=	8300.0	nM	PMID[35367708]
NPT22995	Cell line	B16-F0	Mus musculus	IC50	=	1200.0	nM	PMID[31961147]
NPT2	Others	Unspecified	n.a.	IC50	=	140900.0	nM	PMID[22300884]
NPT2	Others	Unspecified	n.a.	Ki	=	1750.0	nM	PMID[22300884]
NPT2	Others	Unspecified	n.a.	IC50	=	1900.0	nM	PMID[22300884]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	20.0	%	PMID[22530779]
NPT2	Others	Unspecified	n.a.	Activity	=	20.0	%	PMID[22530779]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	26.0	%	DOI[10.1584/jpestics.23.54]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	70.2	%	DOI[10.1584/jpestics.23.54]
NPT22992	Cell line	MUGMel1	Homo sapiens	IC50	=	1900.0	nM	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	IC50	=	1100.0	nM	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	IC50	=	1000.0	nM	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	IC50	=	1900.0	nM	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	IC50	=	1100.0	nM	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	IC50	=	1200.0	nM	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	Activity	=	94.02	%	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	Activity	=	3.51	%	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	Activity	=	2.36	%	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	Activity	=	0.11	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	21.29	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	8.44	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	70.21	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	0.06	%	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	Activity	=	49.48	%	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	Activity	=	40.28	%	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	Activity	=	10.11	%	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	Activity	=	0.15	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	8.43	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	16.44	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	77.12	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	0.0	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	FC	=	1.37	n.a.	PMID[31961147]
NPT22992	Cell line	MUGMel1	Homo sapiens	FC	=	2.4	n.a.	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	Activity	=	50.0	%	PMID[31961147]
NPT22990	Cell line	SBcl2	Homo sapiens	IC50	=	1100.0	nM	PMID[35367708]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC29771 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7798
0.1-0.2	38444
0.2-0.3	3539
0.3-0.4	49
0.4-0.5	3
0.5-0.6	1
0.6-0.7	4
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC111422
0.8511	High Similarity	NPC216312
0.8511	High Similarity	NPC299405
0.8333	Intermediate Similarity	NPC256463
0.8	Intermediate Similarity	NPC241349
0.8	Intermediate Similarity	NPC306835
0.8	Intermediate Similarity	NPC37992
0.7843	Intermediate Similarity	NPC32749
0.7843	Intermediate Similarity	NPC42262
0.7692	Intermediate Similarity	NPC147542
0.7692	Intermediate Similarity	NPC220496
0.7692	Intermediate Similarity	NPC327916
0.7692	Intermediate Similarity	NPC257003
0.7692	Intermediate Similarity	NPC476477
0.7547	Intermediate Similarity	NPC471602
0.7368	Intermediate Similarity	NPC474300
0.7321	Intermediate Similarity	NPC274085
0.6721	Remote Similarity	NPC471444
0.6379	Remote Similarity	NPC476473
0.6207	Remote Similarity	NPC89664
0.6176	Remote Similarity	NPC474301
0.5283	Remote Similarity	NPC306765

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC29771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3896
0.1-0.2	5152
0.2-0.3	101
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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