NPASS Compound

Natural Product: NPC899

Natural Product ID	NPC899
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl Abietate
IUPAC Name	methyl (1R,4aR,4bR,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate
Synonyms	Methyl Abietadien-18-oate; Methyl Abietate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509586
PubChem CID	173058
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 55 57 0 0 0 0 0 0 0 0999 V2000 -5.0992 -0.9091 2.1856 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8561 0.0059 1.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5864 -0.5647 -0.1754 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3981 0.1420 0.7555 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8908 -0.2260 -0.4030 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4466 -0.1080 -0.6891 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9007 -0.4847 -1.8142 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5497 -0.3723 -2.1164 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2895 -0.1902 -0.8046 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6871 0.9859 -0.0891 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3767 2.1460 -1.0023 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4864 1.4691 1.0648 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9476 1.5534 0.8536 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4400 1.0816 -0.4722 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7632 -0.1714 -0.9362 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1891 -0.3971 -2.3945 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4165 -1.3000 -0.1787 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7331 -2.1242 0.4668 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7880 -1.4449 -0.1839 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4744 -2.4741 0.4997 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6460 0.4887 0.4335 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4490 1.4978 1.1575 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5657 0.6989 1.8547 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1095 -0.6907 2.5923 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1212 -1.9579 1.7990 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3536 -0.7924 2.9725 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3166 0.9883 1.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6634 -0.6027 0.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1832 -1.5712 -0.3939 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4325 0.1120 -1.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5355 -0.6315 -1.1865 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5743 -0.9100 -2.5743 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 -1.3674 -2.5684 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7865 0.3790 -2.8659 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0291 -1.1180 -0.2098 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2945 2.8312 -0.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2338 2.7485 -1.2876 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1979 1.8760 -1.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2186 0.8312 1.9537 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1002 2.4926 1.3374 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4521 0.9250 1.6449 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3366 2.5816 1.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5324 0.8171 -0.3320 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4625 1.8738 -1.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8726 -1.4247 -2.6589 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8159 0.3756 -3.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3064 -0.4251 -2.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8242 -3.3529 0.6698 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8314 -2.0722 1.4687 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3442 -2.7686 -0.1251 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4206 -0.3485 1.1302 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0194 2.1969 0.4761 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8319 2.0431 1.8890 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0779 -0.1565 2.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1536 1.3433 2.5284 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 10 21 1 0 21 22 1 0 22 23 1 0 23 4 1 0 21 6 1 0 15 9 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 3 28 1 0 3 29 1 0 3 30 1 0 5 31 1 0 7 32 1 0 8 33 1 0 8 34 1 0 9 35 1 1 11 36 1 0 11 37 1 0 11 38 1 0 12 39 1 0 12 40 1 0 13 41 1 0 13 42 1 0 14 43 1 0 14 44 1 0 16 45 1 0 16 46 1 0 16 47 1 0 20 48 1 0 20 49 1 0 20 50 1 0 21 51 1 1 22 52 1 0 22 53 1 0 23 54 1 0 23 55 1 0 M END

Standard InCHIKey	OVXRPXGVKBHGQO-UYWIDEMCSA-N
Standard InCHI	InChI=1S/C21H32O2/c1-14(2)15-7-9-17-16(13-15)8-10-18-20(17,3)11-6-12-21(18,4)19(22)23-5/h8,13-14,17-18H,6-7,9-12H2,1-5H3/t17-,18+,20+,21+/m0/s1
SMILES	CC(C)C1=CC2=CC[C@@H]3[C@](C)(CCC[C@@]3(C)C(=O)OC)[C@H]2CC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	316.24	Volume:	355.774 ? Van der Waals volume.
Dense:	0.889	LogP:	5.069 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.996 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.248 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	17.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.647	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.166	Fsp³:	0.762
MCE-18:	53.351 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.69	Fluc inhibitor:	0.278 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.884	Promiscuous compounds:	0.016

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.478	MDCK Permeability:	-4.799
Pgp-inhibitor:	0.961	Pgp-substrate:	0.002
PAMPA:	0.001 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.144	30% Bioavailability (F30%):	0.579
50% Bioavailability (F50%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061	MRP1:	0.965
Plasma Protein Binding (PPB):	97.977%	Volume Distribution (VD):	0.088
Fu:	2.5% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.877
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.981	CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.331
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.007	CYP2D6-substrate:	0.993
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.004	CYP2C8-inhibitor:	0.998
HLM stability:	0.949 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

8.923

Half-life (T1/2):

0.131

ADMET: Toxicity

hERG Blockers:	0.119	hERG Blockers (10um):	0.403
Human Hepatotoxicity (H-HT):	0.618	Drug-induced Liver Injury (DILI):	0.432
AMES Toxicity:	0.183	Rat Oral Acute Toxicity:	0.332
Maximum Recommended Daily Dose:	0.519	Skin Sensitization:	0.768
Carcinogencity:	0.756	Eye Corrosion:	0.275
Eye Irritation:	0.858	Respiratory Toxicity:	0.744
Drug-induced Neurotoxicity:	0.204	Ototoxicity:	0.458
Hematotoxicity:	0.475	Drug-induced Nephrotoxicity:	0.622
Genotoxicity:	0.203	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.217	Hek293 Cytotoxicity:	0.288
BCF:	2.844 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.784 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.751 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.565 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25880	Sarcococca coriacea	Species	Buxaceae	Eukaryota	leaves	Nepalese	n.a.	PMID[11421762]
NPO9829	Arnica chamissonis	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[16644542]
NPO9829	Arnica chamissonis	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[16644542]
NPO9829	Arnica chamissonis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO20800	Pholiota nameko	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6851	Aplysilla pallida	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25880	Sarcococca coriacea	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9829	Arnica chamissonis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24299	Litsea laurifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24299	Litsea laurifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24479	Phaseolus atropurpureus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25880	Sarcococca coriacea	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6851	Aplysilla pallida	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10310	Cutaneotrichosporon cutaneum	Species	Trichosporonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24299	Litsea laurifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20800	Pholiota nameko	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6478	Tubifera ferruginosa	Species	Reticulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25483	Croton cortesianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25421	Stemodia viscosa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26799	Vitis heyneana	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26464	Macaranga indica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593.1	Pinus sylvestris var. hamata	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26582	Erigeron sumatrensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9829	Arnica chamissonis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26279	Premna schimperi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24568	Spongia zimocca	Species	Spongiidae	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
Potency	26
CC100	1
Activity	2
IC50	3
MIC	4
CC50	3

Activity Type	# Activity
Individual protein	3
Cell line	7
Organism	6
Others	23

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT162	Individual protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT163	Individual protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	48972.2	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	CC100	=	50.0	ug ml-1	PMID[19217699]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	81310.0	nM	PMID[28011223]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	79320.0	nM	PMID[28011223]
NPT81	Cell line	A549	Homo sapiens	IC50	=	63100.0	nM	PMID[28011223]
NPT165	Cell line	HeLa	Homo sapiens	CC50	=	3.6	ug.mL-1	PMID[19217699]
NPT189	Cell line	Vero	Chlorocebus aethiops	CC50	=	49.4	ug.mL-1	PMID[19217699]
NPT165	Cell line	HeLa	Homo sapiens	CC50	=	11000.0	nM	PMID[19892441]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	10.0	n.a.	PMID[19217699]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	6.25	ug ml-1	PMID[19217699]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	75.0	ug.mL-1	PMID[29153424]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[29153424]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	75.0	ug.mL-1	PMID[29153424]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3890	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1737.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	48972.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	544.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	243.4	nM	PubChem BioAssay data set
NPT1209	Organism	Pseudomonas fluorescens	Pseudomonas fluorescens	MIC	=	50.0	ug.mL-1	PMID[29153424]

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
-	Rattus norvegicus	LD50	>	5000.0	mg/kg	ToxVal
-	Oryctolagus cuniculus	LD50	>	5000.0	mg/kg	ToxVal

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 NPC899 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	21267
0.1-0.2	25425
0.2-0.3	3001
0.3-0.4	149
0.4-0.5	11
0.5-0.6	2
0.6-0.7	2
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC4827
0.6735	Remote Similarity	NPC193770
0.62	Remote Similarity	NPC216460
0.5556	Remote Similarity	NPC15910
0.5455	Remote Similarity	NPC166797

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7108
0.1-0.2	1956
0.2-0.3	85
0.3-0.4	0
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