NPASS Compound

Natural Product: NPC183283

Natural Product ID	NPC183283
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lucialdehyde C
IUPAC Name	(6R)-6-[(3S,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-7-oxo-1,2,3,5,6,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanal
Synonyms	Lucialdehyde C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL470979
PubChem CID	44575605
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 82 85 0 0 0 0 0 0 0 0999 V2000 9.1910 -0.5805 -0.0726 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1023 -0.8449 -0.5888 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8149 -0.3250 -0.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1974 0.5720 -1.0472 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8456 0.7258 -2.2213 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9869 1.3788 -0.8800 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6895 0.6737 -0.9592 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3607 -0.4006 -0.0070 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0169 -1.0264 -0.1836 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8802 -2.1075 0.8638 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4832 -1.8694 1.4589 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2123 -1.3359 0.2457 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7897 -0.2341 -0.1741 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6171 0.8826 0.7677 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2995 0.2000 -1.5354 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1623 0.1745 -1.7230 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9762 0.0345 -0.5170 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5087 -0.7212 0.4765 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2577 -0.9147 1.6814 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7062 -1.2726 2.7285 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7380 -0.6592 1.5962 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9973 0.6267 0.8330 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2832 0.7323 -0.4608 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0035 2.2020 -0.7061 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0529 0.2312 -1.6532 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5155 0.3997 -1.5943 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1304 -0.0077 -0.2773 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4694 0.8109 0.7903 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0335 0.3083 2.1286 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9044 2.2518 0.6755 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4878 0.2710 -0.3413 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3254 -2.4245 -0.7739 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6911 -0.0258 1.3937 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1593 0.4209 1.2316 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1606 -1.4853 -1.4616 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2368 -1.1978 0.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7681 0.2018 -2.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4275 1.3721 -2.9788 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9818 2.1989 -1.6528 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0293 1.9240 0.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9218 1.5171 -0.8382 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6179 0.3222 -2.0380 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0610 -1.2625 -0.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0537 -1.5617 -1.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8305 -3.1233 0.4181 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6661 -2.1411 1.6108 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5484 -1.1705 2.3130 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0216 -2.8028 1.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0334 1.7009 0.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5489 1.4060 1.0552 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0232 0.6598 1.6506 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8506 -0.4087 -2.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6563 1.2631 -1.6682 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3912 -0.6824 -2.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5061 1.0604 -2.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2264 -1.5274 1.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0777 -0.5220 2.6383 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5895 1.4387 1.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5239 2.5838 -1.6261 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2814 2.8347 0.1788 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9329 2.4312 -0.8742 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6680 0.7556 -2.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8206 -0.8474 -1.8190 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9721 -0.2709 -2.3683 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8262 1.4320 -1.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0160 -1.0820 -0.1395 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0457 -0.7879 2.1751 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1181 0.6201 2.1040 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5839 0.8135 2.9829 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5851 2.8194 1.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0274 2.2385 0.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6316 2.7118 -0.2887 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9364 -0.3425 0.3060 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2412 -2.2768 -1.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0084 -3.4290 -0.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4226 -2.6053 -0.9964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8771 -0.2154 2.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9535 1.0407 1.5291 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5574 -0.6070 1.8318 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2948 -0.3462 2.0192 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3623 1.0987 1.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1532 0.9408 1.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 27 31 1 0 12 32 1 6 8 33 1 0 3 34 1 0 13 9 1 0 23 17 1 0 18 12 1 0 28 22 1 0 2 35 1 0 3 36 1 0 5 37 1 0 5 38 1 0 6 39 1 0 6 40 1 0 7 41 1 0 7 42 1 0 8 43 1 6 9 44 1 6 10 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 14 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 21 56 1 0 21 57 1 0 22 58 1 0 24 59 1 0 24 60 1 0 24 61 1 0 25 62 1 0 25 63 1 0 26 64 1 0 26 65 1 0 27 66 1 1 29 67 1 0 29 68 1 0 29 69 1 0 30 70 1 0 30 71 1 0 30 72 1 0 31 73 1 0 32 74 1 0 32 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 M END

Standard InCHIKey	ZLINFWYHFGTJCG-WVKDCGJFSA-N
Standard InCHI	InChI=1S/C31H48O3/c1-19(21(3)18-32)9-10-20(2)22-11-16-31(8)27-23(12-15-30(22,31)7)29(6)14-13-26(34)28(4,5)25(29)17-24(27)33/h18,20-22,25-26,34H,1,9-17H2,2-8H3/t20-,21?,22-,25?,26+,29-,30-,31+/m1/s1
SMILES	O=CC(C(=C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2C(=O)CC2[C@]1(C)CC[C@@H](C2(C)C)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.36	Volume:	526.331 ? Van der Waals volume.
Dense:	0.89	LogP:	4.34 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.75 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.144 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	23.0
TPSA:	54.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.335	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.017	Fsp³:	0.806
MCE-18:	82.5 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.948	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.49	Promiscuous compounds:	0.079

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.009	MDCK Permeability:	-4.657
Pgp-inhibitor:	0.31	Pgp-substrate:	0.023
PAMPA:	0.705 ? 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%):	0.557	30% Bioavailability (F30%):	0.634
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.427	MRP1:	0.903
Plasma Protein Binding (PPB):	94.083%	Volume Distribution (VD):	-0.021
Fu:	6.96% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.576
BSEP inhibitor:	0.871

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.528
CYP2C19-inhibitor:	0.976	CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.619
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.016	CYP2C8-inhibitor:	1.0
HLM stability:	0.304 ? 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):

11.124

Half-life (T1/2):

0.296

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.17
Human Hepatotoxicity (H-HT):	0.605	Drug-induced Liver Injury (DILI):	0.073
AMES Toxicity:	0.309	Rat Oral Acute Toxicity:	0.259
Maximum Recommended Daily Dose:	0.654	Skin Sensitization:	0.971
Carcinogencity:	0.76	Eye Corrosion:	0.047
Eye Irritation:	0.756	Respiratory Toxicity:	0.725
Drug-induced Neurotoxicity:	0.062	Ototoxicity:	0.639
Hematotoxicity:	0.504	Drug-induced Nephrotoxicity:	0.727
Genotoxicity:	0.699	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.284	Hek293 Cytotoxicity:	0.407
BCF:	1.934 ? 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:	4.658 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.1 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.526 ? 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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO32479	gleophyllum lucidum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[Title]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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
ED50	4
IC50	4

Activity Type	# Activity
Cell line	4
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
NPT1317	Cell line	CCRF S-180	Mus musculus	ED50	=	7.1	ug ml-1	PMID[14987072]
NPT396	Cell line	T47D	Homo sapiens	ED50	=	4.7	ug ml-1	PMID[14987072]
NPT1317	Cell line	CCRF S-180	Mus musculus	IC50	=	7.1	ug.mL-1	PMID[23092389]
NPT396	Cell line	T47D	Homo sapiens	IC50	=	4.7	ug.mL-1	PMID[23092389]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	3.8	ug ml-1	PMID[14987072]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	10.7	ug ml-1	PMID[14987072]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	10.7	ug.mL-1	PMID[23092389]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3.8	ug.mL-1	PMID[23092389]

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 NPC183283 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	20245
0.1-0.2	25082
0.2-0.3	4073
0.3-0.4	365
0.4-0.5	60
0.5-0.6	13
0.6-0.7	8
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8103	Intermediate Similarity	NPC110021
0.8103	Intermediate Similarity	NPC482426
0.7377	Intermediate Similarity	NPC275740
0.7377	Intermediate Similarity	NPC86319
0.7097	Intermediate Similarity	NPC482424
0.7031	Intermediate Similarity	NPC69454
0.6984	Remote Similarity	NPC259286
0.6984	Remote Similarity	NPC83216
0.6984	Remote Similarity	NPC484085
0.6935	Remote Similarity	NPC482423
0.6774	Remote Similarity	NPC131470
0.6724	Remote Similarity	NPC482425
0.6716	Remote Similarity	NPC601194
0.6129	Remote Similarity	NPC118508
0.5676	Remote Similarity	NPC489808
0.5676	Remote Similarity	NPC489800
0.5625	Remote Similarity	NPC484086
0.5588	Remote Similarity	NPC99909
0.5588	Remote Similarity	NPC249954
0.5522	Remote Similarity	NPC143767
0.5417	Remote Similarity	NPC484971
0.5417	Remote Similarity	NPC484970
0.5352	Remote Similarity	NPC191684
0.5342	Remote Similarity	NPC482518
0.5294	Remote Similarity	NPC471724
0.5075	Remote Similarity	NPC46160
0.5075	Remote Similarity	NPC202642

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC183283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6900
0.1-0.2	2147
0.2-0.3	103
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