NPASS Compound

Natural Product: NPC99909

Natural Product ID	NPC99909
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lucidumol A
IUPAC Name	(5R,10S,13R,14R,17R)-17-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-4,4,10,13,14-pentamethyl-2,5,6,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,7-dione
Synonyms	Lucidumol A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1917739
PubChem CID	475410
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 3.0301 0.9241 -1.2064 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9298 0.7939 0.2632 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5970 1.1556 0.8378 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3541 2.6184 0.4460 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0389 2.5990 -0.2024 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6629 1.5053 0.5738 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4055 0.3818 0.5780 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2975 -0.4415 -0.6454 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0910 -0.4670 1.7561 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4616 -0.9972 1.5108 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2723 -0.2387 0.5491 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9181 0.9581 0.0829 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7695 1.6601 -0.8696 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3142 2.5669 -1.5896 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2271 1.3015 -1.0037 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5617 0.3071 0.0885 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5549 -0.7996 0.0463 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2672 -1.2563 -1.3876 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9487 -2.0169 0.8426 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3085 -2.5108 0.4077 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2747 -1.4201 0.6595 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2629 -1.6775 1.3319 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9865 -0.0895 0.0839 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7611 0.9129 0.9557 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6601 -0.0043 -1.2793 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8522 2.0366 2.0050 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5943 -0.3723 0.8413 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0642 -0.5455 0.7149 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6425 -0.6946 -0.6328 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1650 -0.8537 -0.4743 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7008 -0.9502 -1.7370 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7526 0.3624 0.1977 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5054 -2.0871 0.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1303 -1.8068 -1.2996 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2501 0.0047 -1.7695 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0713 1.3101 -1.6700 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7716 1.6991 -1.5712 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5735 1.6839 0.6513 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7606 1.1901 1.9598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2895 3.2900 1.3051 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1052 3.0066 -0.2401 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0024 2.4603 -1.2773 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5274 3.5730 -0.0022 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3823 -1.3352 -0.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1320 0.1010 -1.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2413 -0.9062 -0.9849 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5802 -1.3210 1.9513 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0880 0.1355 2.7036 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3945 -2.0567 1.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9915 -1.1058 2.4957 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4714 0.9723 -2.0107 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7887 2.2306 -0.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3543 0.8624 1.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0961 -2.3509 -1.4238 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3469 -0.7811 -1.7855 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0727 -1.0264 -2.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2090 -2.8139 0.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0131 -1.7310 1.9026 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5515 -3.4343 0.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3635 -2.7700 -0.6565 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7727 0.4493 1.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9131 1.8657 0.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3134 0.9935 1.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4543 -0.8534 -1.9260 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7598 -0.0293 -1.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4857 0.9916 -1.7282 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6163 1.4755 2.5483 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2850 3.0691 1.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0945 2.1886 2.5291 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3648 -0.5417 1.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1582 -1.3331 0.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5103 0.4007 1.1897 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4084 -1.4097 1.3826 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5056 0.1925 -1.2503 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2022 -1.6102 -2.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7045 0.3102 1.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8155 0.4485 -0.1649 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2558 1.3077 -0.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5405 -1.8641 1.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5596 -2.3638 0.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8378 -2.9250 0.0918 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8049 -2.5043 -0.6687 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 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 23 25 1 0 6 26 1 1 2 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 30 33 1 0 29 34 1 0 7 3 1 0 17 11 1 0 12 6 1 0 23 16 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 1 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 8 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 15 51 1 0 15 52 1 0 16 53 1 1 18 54 1 0 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 24 61 1 0 24 62 1 0 24 63 1 0 25 64 1 0 25 65 1 0 25 66 1 0 26 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 28 73 1 0 29 74 1 6 31 75 1 0 32 76 1 0 32 77 1 0 32 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 34 82 1 0 M END

Standard InCHIKey	LVGCWXNRZNCAJG-AMKDLFIQSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-18(9-10-24(33)27(4,5)34)19-11-16-30(8)25-20(12-15-29(19,30)7)28(6)14-13-23(32)26(2,3)22(28)17-21(25)31/h18-19,22,24,33-34H,9-17H2,1-8H3/t18-,19-,22+,24+,28-,29-,30+/m1/s1
SMILES	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2C(=O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)CC[C@@H](C(O)(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	520.462 ? Van der Waals volume.
Dense:	0.908	LogP:	4.162 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.938 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.471 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.512	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.81	Fsp³:	0.867
MCE-18:	86.25 ? 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:	0.881	Fluc inhibitor:	0.0 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.426	Promiscuous compounds:	0.34

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.775	MDCK Permeability:	-4.502
Pgp-inhibitor:	0.852	Pgp-substrate:	0.009
PAMPA:	0.26 ? 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%):	0.022	30% Bioavailability (F30%):	0.02
50% Bioavailability (F50%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.349	MRP1:	0.952
Plasma Protein Binding (PPB):	91.585%	Volume Distribution (VD):	0.274
Fu:	8.711% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.887
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.945	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.479	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.564
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.049 ? 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):

10.473

Half-life (T1/2):

0.383

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.101
Human Hepatotoxicity (H-HT):	0.748	Drug-induced Liver Injury (DILI):	0.202
AMES Toxicity:	0.262	Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.751	Skin Sensitization:	0.99
Carcinogencity:	0.882	Eye Corrosion:	0.015
Eye Irritation:	0.493	Respiratory Toxicity:	0.733
Drug-induced Neurotoxicity:	0.091	Ototoxicity:	0.661
Hematotoxicity:	0.767	Drug-induced Nephrotoxicity:	0.958
Genotoxicity:	0.618	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.233	Hek293 Cytotoxicity:	0.5
BCF:	1.016 ? 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:	3.71 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.322 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.568 ? 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]
NPO16609	Ganoderma sinense	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]
NPO16609	Ganoderma sinense	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[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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
EC50	1
IC50	1
ED50	2

Activity Type	# Activity
Cell line	1
Protein complex	1
Non-molecular	2

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	11000.0	nM	PMID[23092389]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	2.3	ug ml-1	PMID[23092389]
NPT22802	Protein complex	Bile acid receptor/Retinoic acid receptor RXR-alpha	Mus musculus	EC50	>	18600.0	nM	PMID[22014750]

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 NPC99909 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	22791
0.1-0.2	23731
0.2-0.3	2887
0.3-0.4	347
0.4-0.5	64
0.5-0.6	27
0.6-0.7	8
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
0.7097	Intermediate Similarity	NPC41539
0.7097	Intermediate Similarity	NPC472940
0.6885	Remote Similarity	NPC90965
0.6769	Remote Similarity	NPC318332
0.6615	Remote Similarity	NPC8571
0.6508	Remote Similarity	NPC605549
0.6349	Remote Similarity	NPC484799
0.6154	Remote Similarity	NPC89077
0.6094	Remote Similarity	NPC110021
0.6094	Remote Similarity	NPC482426
0.5758	Remote Similarity	NPC275740
0.5758	Remote Similarity	NPC86319
0.5692	Remote Similarity	NPC481295
0.5672	Remote Similarity	NPC259286
0.5672	Remote Similarity	NPC83216
0.5672	Remote Similarity	NPC472931
0.5672	Remote Similarity	NPC484085
0.5672	Remote Similarity	NPC260992
0.5588	Remote Similarity	NPC183283
0.5522	Remote Similarity	NPC482424
0.5507	Remote Similarity	NPC69454
0.5455	Remote Similarity	NPC131470
0.5429	Remote Similarity	NPC44181
0.5429	Remote Similarity	NPC606857
0.5405	Remote Similarity	NPC478297
0.5373	Remote Similarity	NPC474083
0.5373	Remote Similarity	NPC606148
0.5286	Remote Similarity	NPC162703
0.5278	Remote Similarity	NPC601194
0.5208	Remote Similarity	NPC472939
0.5205	Remote Similarity	NPC456
0.5205	Remote Similarity	NPC472941
0.5205	Remote Similarity	NPC202814
0.5147	Remote Similarity	NPC482423
0.5135	Remote Similarity	NPC489798
0.5079	Remote Similarity	NPC482425
0.5077	Remote Similarity	NPC282275

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC99909 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7288
0.1-0.2	1710
0.2-0.3	149
0.3-0.4	3
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