NPASS Compound

Natural Product: NPC259875

Natural Product ID	NPC259875
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sid535877
IUPAC Name	(1S,2S,3R,4aS,6aR,6bS,8aR,11R,12S,12aR,14R,14aS,14bS)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-1,2,3,14-tetrol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL511638
PubChem CID	404646
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 88 0 0 0 0 0 0 0 0999 V2000 4.4403 0.9319 2.8586 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7690 -0.1805 1.8668 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5846 0.4476 0.7737 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4363 -0.2135 -0.5483 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9932 -0.1745 -0.9504 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9463 -0.9118 -2.3083 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4812 1.1821 -1.2469 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0252 1.1538 -1.6320 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1664 0.5328 -0.5460 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3388 1.5199 0.6244 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7386 -0.7744 -0.2325 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9565 -1.8285 -0.1791 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5038 -1.8833 -0.4060 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0817 -0.5453 -0.2410 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2971 0.5161 -0.8784 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3420 0.5825 -2.3906 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8918 1.8651 -0.4718 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3663 1.9717 -0.7253 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0063 0.8315 0.0447 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4187 1.1328 0.2722 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3034 1.2198 -0.9221 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4959 2.4905 0.9788 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9416 0.1678 1.3230 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6794 -1.1946 0.8337 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2408 -1.5171 0.5113 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5950 -0.5027 -0.4495 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0682 -0.9092 -1.7874 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4506 -2.7514 -0.1728 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0732 -2.1107 1.8084 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3224 0.3578 1.3845 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9415 -2.8511 0.4930 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1913 -0.9845 0.0245 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5716 -0.9146 1.4577 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6492 -2.3204 2.1049 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3846 0.7658 3.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0710 0.9239 3.7544 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4305 1.9214 2.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5037 -0.8324 2.4334 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6903 0.4504 1.0153 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3322 1.5231 0.6614 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7775 -1.2566 -0.5814 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0094 0.3563 -1.2958 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9409 -1.2575 -2.5424 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6344 -1.7871 -2.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2673 -0.2170 -3.1109 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7578 1.9795 -0.5435 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0090 1.5031 -2.2036 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9470 0.6639 -2.5998 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7967 2.2344 -1.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1077 2.5249 0.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4113 1.5969 0.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8208 1.2181 1.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5108 -2.7787 0.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 -2.2936 -1.4057 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0121 -0.3251 0.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3625 0.7386 -2.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1204 -0.2674 -2.8888 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1288 1.5709 -2.6416 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4373 2.6925 -1.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7899 2.0213 0.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7003 2.9060 -0.2250 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6608 2.0323 -1.7612 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5116 0.9169 1.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6783 0.2413 -1.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2380 1.7787 -0.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8266 1.8332 -1.6840 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5850 2.6482 1.6161 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6475 3.3109 0.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3568 2.5253 1.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5415 0.3763 2.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3657 -1.3811 -0.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6860 -1.6342 1.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8805 -1.7072 -1.7852 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5582 -0.1054 -2.3783 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2538 -1.4088 -2.3446 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7204 -3.3766 0.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5639 -2.8757 1.4413 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7694 -0.0317 0.5927 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3179 -3.5789 0.6287 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4891 -2.0487 -0.2678 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6788 -0.4873 2.0115 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3323 -2.9688 1.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6643 -2.7816 2.1748 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1375 -2.1885 3.1070 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 6 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 25 28 1 0 24 29 1 0 23 30 1 0 13 31 1 0 11 32 1 0 32 33 1 0 33 34 1 0 33 2 1 0 32 5 1 0 15 9 1 0 26 19 1 0 26 14 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 6 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 10 52 1 0 12 53 1 0 13 54 1 6 14 55 1 1 16 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 1 21 64 1 0 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 22 69 1 0 23 70 1 1 24 71 1 6 25 72 1 1 27 73 1 0 27 74 1 0 27 75 1 0 28 76 1 0 29 77 1 0 30 78 1 0 31 79 1 0 32 80 1 6 33 81 1 1 34 82 1 0 34 83 1 0 34 84 1 0 M END

Standard InCHIKey	YZTZJWAFBBUUTI-AQQFODMKSA-N
Standard InCHI	InChI=1S/C30H50O4/c1-16-9-11-27(5)13-14-28(6)18(21(27)17(16)2)15-19(31)23-29(28,7)12-10-20-26(3,4)24(33)22(32)25(34)30(20,23)8/h15-17,19-25,31-34H,9-14H2,1-8H3/t16-,17+,19-,20+,21+,22+,23+,24+,25-,27-,28-,29-,30+/m1/s1
SMILES	C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=C[C@H]([C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@H]([C@@H]([C@H]([C@]43C)O)O)O)O)[C@@H]2[C@H]1C

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
NPO23829	Salvia kronenburgii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738403]
NPO23829	Salvia kronenburgii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23829	Salvia kronenburgii	Species	Lamiaceae	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	1
GI50	53
Activity	3

Activity Type	# Activity
Cell line	57

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
NPT179	Cell line	A2780	Homo sapiens	IC50	=	27.7	ug.mL-1	PMID[25978960]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	=	363.08	nM	PMID[10514334]
NPT396	Cell line	T47D	Homo sapiens	GI50	=	18620.87	nM	PMID[10514334]
NPT397	Cell line	NCI-H460	Homo sapiens	Activity	=	-45.0	%	PMID[25978960]
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	-25.0	%	PMID[25978960]
NPT395	Cell line	SF-268	Homo sapiens	Activity	=	18.0	%	PMID[12617583]
NPT394	Cell line	EKVX	Homo sapiens	GI50	=	21.88	nM	PMID[12617583]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[25634623]
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[13678412]
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[8676127]
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[8182707]
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[16180822]
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[17988093]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[18183025]
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[17844994]
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[20308383]
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	77090.35	nM	PMID[26034885]
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[24417583]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	82413.81	nM	PMID[16499322]
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[16643039]
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[11908966]
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[23320609]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[10479316]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	Open TG-GATES in vivo data: Biochemistry
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[19880317]
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[8021914]
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	96161.23	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[24694263]
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	55590.43	nM	PMID[8410974]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[17417907]
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[20695474]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[21925888]
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[20805391]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[1982768]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[25744190]
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[17315965]
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[8410981]
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	22.08	nM	DOI[10.1007/s00044-013-0720-3]
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[17609121]
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	18706.82	nM	PMID[15161186]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[18458131]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[2549244]
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	DrugMatrix in vivo data: Biochemistry
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[22037378]
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	67764.15	nM	DrugMatrix in vivo data: Pathology
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[1904475]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[23398362]
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[24224843]
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[15104495]
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[19299148]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	361.41	nM	PMID[23642481]
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	DOI[10.6019/CHEMBL1201861]

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 NPC259875 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	29082
0.1-0.2	19301
0.2-0.3	1388
0.3-0.4	62
0.4-0.5	18
0.5-0.6	1
0.6-0.7	2
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	Natural Product ID
0.7222	Intermediate Similarity	NPC187785
0.6508	Remote Similarity	NPC96784
0.6066	Remote Similarity	NPC274724
0.5079	Remote Similarity	NPC295131

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC259875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8159
0.1-0.2	974
0.2-0.3	17
0.3-0.4	0
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