NPASS Compound

Natural Product: NPC473913

Natural Product ID	NPC473913
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3S,4E,15Z)-Docosa-4,15-Dien-1-Yn-3-Ol
IUPAC Name	(3S,4E,15Z)-docosa-4,15-dien-1-yn-3-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL455110
PubChem CID	5469777
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

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 61 60 0 0 0 0 0 0 0 0999 V2000 5.9646 -1.0713 0.6952 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9138 0.1767 1.5036 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0553 1.2841 0.9434 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4879 1.7467 -0.4239 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7001 2.8903 -0.9395 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2445 2.7309 -1.1193 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7974 1.7156 -2.0841 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0411 0.6799 -1.8407 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4492 0.2685 -0.5520 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0830 0.3004 -0.6890 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.1335 0.5633 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5028 -1.5540 0.9848 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9397 -2.5633 -0.0042 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4354 -2.5484 -0.3223 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1899 -2.7968 0.9133 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6261 -2.9013 0.9587 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5734 -1.8582 0.5922 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5083 -0.5932 1.3464 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3538 0.5958 0.8127 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2228 0.9063 -0.6307 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4543 2.4014 -0.7688 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6358 3.5312 -0.8674 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9400 0.7206 -1.1457 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2071 -1.8090 1.0086 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9445 -0.8920 -0.3957 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9674 -1.5536 0.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4953 -0.0558 2.5257 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9411 0.5946 1.6828 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0368 0.8610 0.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0578 2.1022 1.6901 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5059 0.9317 -1.1496 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5517 2.1100 -0.3187 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8588 3.7747 -0.2661 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1585 3.1892 -1.9150 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8706 3.7309 -1.5212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7192 2.6656 -0.1334 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1284 1.8278 -3.1469 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8072 0.0148 -2.7006 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7997 -0.7415 -0.2393 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7563 0.9793 0.2357 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3008 1.4123 -0.7732 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4255 -0.1502 -1.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8478 0.0257 0.4500 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3539 0.5038 1.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6175 -1.6719 1.0780 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8997 -1.7354 1.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3458 -2.4210 -0.9372 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6655 -3.5986 0.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6372 -1.4982 -0.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5590 -3.2645 -1.1532 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8314 -1.9919 1.6478 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7356 -3.7264 1.3854 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9626 -3.8557 0.4106 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9039 -3.2065 2.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6046 -1.5779 -0.4838 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6340 -2.2373 0.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6022 -0.6826 2.4306 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3262 1.4328 1.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0058 0.4259 -1.2289 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7934 4.6301 -0.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3957 1.5290 -0.9086 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 3 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 3 19 20 1 0 20 21 1 0 21 22 3 0 20 23 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 0 5 34 1 0 6 35 1 0 6 36 1 0 7 37 1 0 8 38 1 0 9 39 1 0 9 40 1 0 10 41 1 0 10 42 1 0 11 43 1 0 11 44 1 0 12 45 1 0 12 46 1 0 13 47 1 0 13 48 1 0 14 49 1 0 14 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 19 58 1 0 20 59 1 0 22 60 1 0 23 61 1 0 M END

Standard InCHIKey	HEXQBSKJVUFXNG-JYHGMTFVSA-N
Standard InCHI	InChI=1S/C22H38O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)4-2/h2,9-10,20-23H,3,5-8,11-19H2,1H3/b10-9-,21-20+/t22-/m1/s1
SMILES	CCCCCCC=CCCCCCCCCCC=CC(C#C)O

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
NPO15047	Cribrochalina vasculum	Species	Niphatidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[1431945]
NPO15047	Cribrochalina vasculum	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8691203]
NPO15047	Cribrochalina vasculum	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984159]
NPO15047	Cribrochalina vasculum	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15047	Cribrochalina vasculum	Species	Niphatidae	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
GI50	59
TGI	59

Activity Type	# Activity
Cell line	112
Others	2
Non-molecular	4

Molecular-level activity

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

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	GI50	=	0.631	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	TGI	=	1.549	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	=	10.23	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	TGI	=	36.31	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	=	30.9	nM	PMID[25819096]
NPT111	Cell line	K562	Homo sapiens	TGI	=	69.18	nM	PMID[25871540]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	=	6.457	nM	PMID[25819096]
NPT112	Cell line	MOLT-4	Homo sapiens	TGI	=	26.92	nM	PMID[25819096]
NPT385	Cell line	SR	Homo sapiens	GI50	=	15.49	nM	PMID[11141087]
NPT385	Cell line	SR	Homo sapiens	TGI	=	54.95	nM	PMID[11141087]
NPT81	Cell line	A549	Homo sapiens	GI50	=	45.71	nM	PMID[11141087]
NPT81	Cell line	A549	Homo sapiens	TGI	=	83.18	nM	PMID[10229619]
NPT394	Cell line	EKVX	Homo sapiens	GI50	=	46.77	nM	PMID[15050613]
NPT394	Cell line	EKVX	Homo sapiens	TGI	=	81.28	nM	PMID[17850214]
NPT379	Cell line	HOP-62	Homo sapiens	GI50	=	52.48	nM	PMID[15050613]
NPT379	Cell line	HOP-62	Homo sapiens	TGI	=	89.13	nM	PMID[2607355]
NPT372	Cell line	HOP-92	Homo sapiens	GI50	=	46.77	nM	PMID[3373221]
NPT372	Cell line	HOP-92	Homo sapiens	TGI	=	83.18	nM	PMID[18563933]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	=	30.2	nM	PMID[2607355]
NPT405	Cell line	NCI-H226	Homo sapiens	TGI	=	61.66	nM	PMID[2607355]
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	=	13.49	nM	PMID[2607355]
NPT370	Cell line	NCI-H23	Homo sapiens	TGI	=	45.71	nM	PMID[2607355]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	=	53.7	nM	PMID[24387703]
NPT388	Cell line	NCI-H322M	Homo sapiens	TGI	=	91.2	nM	PMID[23268719]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	42.66	nM	PMID[17315926]
NPT397	Cell line	NCI-H460	Homo sapiens	TGI	=	79.43	nM	PMID[23268719]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	=	0.1148	nM	PMID[23265253]
NPT455	Cell line	NCI-H522	Homo sapiens	TGI	=	0.4365	nM	PMID[23265253]
NPT407	Cell line	COLO 205	Homo sapiens	GI50	=	43.65	nM	PMID[15711537]
NPT407	Cell line	COLO 205	Homo sapiens	TGI	=	79.43	nM	PMID[15711537]
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	=	43.65	nM	PMID[26722868]
NPT391	Cell line	HCC 2998	Homo sapiens	TGI	=	79.43	nM	PMID[15711537]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	=	25.12	nM	PMID[15711537]
NPT393	Cell line	HCT-116	Homo sapiens	TGI	=	54.95	nM	PMID[15711537]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	=	36.31	nM	PMID[15711537]
NPT148	Cell line	HCT-15	Homo sapiens	TGI	=	69.18	nM	PMID[9644083]
NPT139	Cell line	HT-29	Homo sapiens	GI50	=	30.9	nM	PMID[12105963]
NPT139	Cell line	HT-29	Homo sapiens	TGI	=	66.07	nM	PMID[16441065]
NPT386	Cell line	KM12	Homo sapiens	GI50	=	37.15	nM	PMID[12105963]
NPT386	Cell line	KM12	Homo sapiens	TGI	=	70.79	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	=	9.333	nM	PMID[12105963]
NPT323	Cell line	SW-620	Homo sapiens	TGI	=	42.66	nM	PMID[12105963]
NPT395	Cell line	SF-268	Homo sapiens	GI50	=	38.9	nM	DrugMatrix in vivo data: Pathology
NPT395	Cell line	SF-268	Homo sapiens	TGI	=	74.13	nM	DrugMatrix in vivo data: Pathology
NPT399	Cell line	SF-295	Homo sapiens	GI50	=	44.67	nM	DrugMatrix in vivo data: Pathology
NPT399	Cell line	SF-295	Homo sapiens	TGI	=	79.43	nM	DrugMatrix in vivo data: Pathology
NPT374	Cell line	SF-539	Homo sapiens	GI50	=	44.67	nM	DrugMatrix in vivo data: Pathology
NPT374	Cell line	SF-539	Homo sapiens	TGI	=	79.43	nM	DrugMatrix in vivo data: Pathology
NPT383	Cell line	SNB-19	Homo sapiens	GI50	=	52.48	nM	PMID[16562829]
NPT383	Cell line	SNB-19	Homo sapiens	TGI	=	89.13	nM	PMID[16562829]
NPT392	Cell line	SNB-75	Homo sapiens	GI50	=	12.3	nM	PMID[16562829]
NPT392	Cell line	SNB-75	Homo sapiens	TGI	=	43.65	nM	PMID[16562829]
NPT380	Cell line	U-251	Homo sapiens	GI50	=	40.74	nM	PMID[16562829]
NPT380	Cell line	U-251	Homo sapiens	TGI	=	74.13	nM	DOI[10.1016/j.bse.2012.02.012]
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	=	6.31	nM	PMID[16562829]
NPT375	Cell line	Malme-3M	Homo sapiens	TGI	=	20.42	nM	PMID[18651728]
NPT387	Cell line	M14	Homo sapiens	GI50	=	8.318	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	TGI	=	39.81	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	=	8.128	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	TGI	=	23.44	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	=	41.69	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	TGI	=	75.86	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	=	32.36	nM	PMID[1336040]
NPT373	Cell line	SK-MEL-5	Homo sapiens	TGI	=	64.57	nM	PMID[1336040]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	=	32.36	nM	DOI[10.6019/CHEMBL1201861]
NPT403	Cell line	UACC-257	Homo sapiens	TGI	=	64.57	nM	PMID[1336040]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	=	38.9	nM	PMID[1336040]
NPT398	Cell line	UACC-62	Homo sapiens	TGI	=	72.44	nM	PMID[11277748]
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	=	0.5623	nM	Open TG-GATES in vivo data: Biochemistry
NPT458	Cell line	IGROV-1	Homo sapiens	TGI	=	1.122	nM	Open TG-GATES in vivo data: Biochemistry
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	=	48.98	nM	Open TG-GATES in vivo data: Biochemistry
NPT377	Cell line	OVCAR-3	Homo sapiens	TGI	=	85.11	nM	Open TG-GATES in vivo data: Biochemistry
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	=	18.62	nM	Open TG-GATES in vivo data: Biochemistry
NPT456	Cell line	OVCAR-4	Homo sapiens	TGI	=	51.29	nM	Open TG-GATES in vivo data: Biochemistry
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	=	46.77	nM	Open TG-GATES in vivo data: Biochemistry
NPT382	Cell line	OVCAR-5	Homo sapiens	TGI	=	81.28	nM	PMID[22892213]
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	=	37.15	nM	PMID[17685651]
NPT381	Cell line	OVCAR-8	Homo sapiens	TGI	=	70.79	nM	PMID[25729554]
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	=	61.66	nM	PMID[17685651]
NPT146	Cell line	SK-OV-3	Homo sapiens	TGI	=	100.0	nM	PMID[17685651]
NPT401	Cell line	786-0	Homo sapiens	GI50	=	42.66	nM	PMID[22892213]
NPT401	Cell line	786-0	Homo sapiens	TGI	=	77.62	nM	PMID[22892213]
NPT376	Cell line	A498	Homo sapiens	GI50	=	58.88	nM	PMID[15679325]
NPT376	Cell line	A498	Homo sapiens	TGI	=	95.5	nM	DOI[10.1021/np50067a001]
NPT369	Cell line	ACHN	Homo sapiens	GI50	=	45.71	nM	PMID[17239597]
NPT369	Cell line	ACHN	Homo sapiens	TGI	=	79.43	nM	PMID[17239597]
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	=	52.48	nM	PMID[17239597]
NPT308	Cell line	CAKI-1	Homo sapiens	TGI	=	91.2	nM	PMID[25682561]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	=	33.11	nM	PMID[19689125]
NPT406	Cell line	RXF 393	Homo sapiens	TGI	=	66.07	nM	PMID[19689125]
NPT368	Cell line	SN12C	Homo sapiens	GI50	=	28.84	nM	PMID[17848089]
NPT368	Cell line	SN12C	Homo sapiens	TGI	=	58.88	nM	PMID[19689125]
NPT384	Cell line	TK-10	Homo sapiens	GI50	=	60.26	nM	PMID[19689125]
NPT384	Cell line	TK-10	Homo sapiens	TGI	=	97.72	nM	PMID[19689125]
NPT371	Cell line	UO-31	Homo sapiens	GI50	=	52.48	nM	PMID[12762819]
NPT371	Cell line	UO-31	Homo sapiens	TGI	=	89.13	nM	PMID[15387645]
NPT306	Cell line	PC-3	Homo sapiens	GI50	=	39.81	nM	PMID[15387645]
NPT306	Cell line	PC-3	Homo sapiens	TGI	=	74.13	nM	PMID[19653640]
NPT90	Cell line	DU-145	Homo sapiens	GI50	=	47.86	nM	PMID[15387645]
NPT90	Cell line	DU-145	Homo sapiens	TGI	=	83.18	nM	PMID[15387645]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	13.8	nM	PMID[6292419]
NPT83	Cell line	MCF7	Homo sapiens	TGI	=	47.86	nM	PMID[10869194]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	=	47.86	nM	PMID[17887662]
NPT82	Cell line	MDA-MB-231	Homo sapiens	TGI	=	83.18	nM	PMID[17887662]
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	=	26.92	nM	PMID[12036352]
NPT400	Cell line	MDA-MB-435	Homo sapiens	TGI	=	57.54	nM	PMID[12036352]
NPT367	Cell line	MDA-N	Homo sapiens	GI50	=	25.12	nM	PMID[12036352]
NPT367	Cell line	MDA-N	Homo sapiens	TGI	=	53.7	nM	DOI[10.1016/S0960-894X(97)00439-3]
NPT457	Cell line	BT-549	Homo sapiens	GI50	=	38.9	nM	PMID[12036352]
NPT457	Cell line	BT-549	Homo sapiens	TGI	=	72.44	nM	PMID[12036352]
NPT396	Cell line	T47D	Homo sapiens	GI50	=	6.31	nM	PMID[14987066]
NPT396	Cell line	T47D	Homo sapiens	TGI	=	42.66	nM	PMID[13678412]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	6.761	nM	PMID[8691203]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	TGI	=	18.62	nM	PMID[8691203]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	44.67	nM	PMID[8691203]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	TGI	=	87.1	nM	PMID[8691203]
NPT2	Others	Unspecified	n.a.	GI50	=	38.02	nM	PMID[17894480]
NPT2	Others	Unspecified	n.a.	TGI	=	72.44	nM	PubChem BioAssay data set

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 NPC473913 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	34914
0.1-0.2	13452
0.2-0.3	1079
0.3-0.4	284
0.4-0.5	66
0.5-0.6	23
0.6-0.7	12
0.7-0.8	0
0.8-0.85	5
0.85-0.9	8
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474642
0.9583	High Similarity	NPC249670
0.875	High Similarity	NPC170776
0.875	High Similarity	NPC9273
0.875	High Similarity	NPC165447
0.875	High Similarity	NPC471959
0.875	High Similarity	NPC199286
0.875	High Similarity	NPC489046
0.875	High Similarity	NPC76198
0.875	High Similarity	NPC610719
0.84	Intermediate Similarity	NPC607242
0.8333	Intermediate Similarity	NPC125122
0.8333	Intermediate Similarity	NPC471276
0.8333	Intermediate Similarity	NPC471280
0.8333	Intermediate Similarity	NPC471281
0.7667	Intermediate Similarity	NPC473865
0.7241	Intermediate Similarity	NPC474644
0.7097	Intermediate Similarity	NPC474643
0.6562	Remote Similarity	NPC161838
0.6364	Remote Similarity	NPC471960
0.6364	Remote Similarity	NPC477727
0.6333	Remote Similarity	NPC600749
0.6333	Remote Similarity	NPC601019
0.625	Remote Similarity	NPC91226
0.625	Remote Similarity	NPC243546
0.625	Remote Similarity	NPC31194
0.625	Remote Similarity	NPC248884
0.6061	Remote Similarity	NPC471239
0.6061	Remote Similarity	NPC72699
0.6061	Remote Similarity	NPC55383
0.5946	Remote Similarity	NPC470966
0.5833	Remote Similarity	NPC197272
0.5789	Remote Similarity	NPC477661
0.5789	Remote Similarity	NPC603233
0.5789	Remote Similarity	NPC607245
0.5676	Remote Similarity	NPC89824
0.5676	Remote Similarity	NPC475477
0.5676	Remote Similarity	NPC256656
0.5676	Remote Similarity	NPC294278
0.5676	Remote Similarity	NPC477723
0.5556	Remote Similarity	NPC484320
0.5526	Remote Similarity	NPC471278
0.5417	Remote Similarity	NPC151719
0.5385	Remote Similarity	NPC48058
0.5385	Remote Similarity	NPC470963
0.5357	Remote Similarity	NPC182392
0.5263	Remote Similarity	NPC85079
0.5263	Remote Similarity	NPC151782
0.525	Remote Similarity	NPC470970
0.5172	Remote Similarity	NPC76976
0.5122	Remote Similarity	NPC224148
0.5122	Remote Similarity	NPC477726
0.5122	Remote Similarity	NPC477725

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8058
0.1-0.2	1022
0.2-0.3	53
0.3-0.4	15
0.4-0.5	1
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