NPASS Compound

Natural Product: NPC202389

Natural Product ID	NPC202389
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ganoderol B
IUPAC Name	(3S,5R,10S,13R,14R,17R)-17-[(E,2R)-7-hydroxy-6-methylhept-5-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL240972
PubChem CID	13934286
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 80 83 0 0 0 0 0 0 0 0999 V2000 7.1209 1.2116 2.9281 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7783 1.3118 1.6848 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0843 0.3506 0.7698 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4986 0.8216 -0.3500 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8138 -0.0573 -1.2718 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3932 0.1206 -1.5897 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3776 -0.0186 -0.4778 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0185 0.1553 -1.0606 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7962 -0.8831 -2.1884 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3024 -0.9635 -2.3701 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2419 0.0762 -1.3754 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8112 -0.1067 -0.2654 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6543 -1.5699 0.1550 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4858 0.7277 0.8945 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9318 0.5571 1.3067 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8688 0.0724 0.5101 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5533 -0.3352 -0.8587 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4317 -1.0443 -1.5529 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7525 -1.4281 -0.9615 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1825 -0.2495 -0.1042 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2643 -0.0527 1.0440 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2211 -1.2079 2.0151 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7057 1.1859 1.7864 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8038 1.9328 1.0628 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0076 1.1046 0.7538 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6439 -0.2660 0.2058 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3491 -0.4261 -1.1515 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0943 -1.3758 1.0925 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8598 0.9778 1.8664 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2496 1.4271 -1.9603 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7532 0.9553 0.5812 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0472 -1.0917 1.0991 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3479 0.3175 3.2950 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6368 2.3485 1.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8421 1.0549 1.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5973 1.9056 -0.5117 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3622 -0.0284 -2.2821 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9377 -1.1331 -0.9310 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1839 1.1304 -2.0722 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1054 -0.6377 -2.3903 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4577 -1.0406 -0.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 1.1206 -1.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2761 -0.4755 -3.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3030 -1.8220 -2.0017 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1227 -1.9540 -2.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0420 -0.5610 -3.3831 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 -1.6437 1.2836 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4575 -2.2173 -0.2195 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3003 -2.0162 -0.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6348 1.8142 0.7929 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0593 0.4156 1.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2580 0.8342 2.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1587 -1.3320 -2.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7375 -2.3791 -0.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4582 -1.5130 -1.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0292 0.6499 -0.7768 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0563 -2.1831 1.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2916 -1.0371 2.6375 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0470 -1.1971 2.7543 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9081 1.9213 1.9648 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1078 0.8981 2.7789 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3925 2.4619 0.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1389 2.7387 1.7772 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6007 1.6626 -0.0004 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3125 0.1095 -1.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7593 0.0975 -1.9319 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4553 -1.5030 -1.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4042 -2.2364 1.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0726 -1.7819 0.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3502 -1.0430 2.1242 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5398 1.7250 1.8741 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0743 2.2438 -1.2932 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3310 1.4204 -2.9239 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2962 1.6832 -2.2661 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9255 1.4539 1.1167 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3944 1.7723 0.1752 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3392 0.4626 1.3768 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4941 -1.6972 0.2603 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7073 -1.2693 1.9676 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0054 -1.4525 1.2940 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 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 1 12 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 11 30 1 6 7 31 1 0 3 32 1 0 12 8 1 0 21 16 1 0 17 11 1 0 26 20 1 0 1 33 1 0 2 34 1 0 2 35 1 0 4 36 1 0 5 37 1 0 5 38 1 0 6 39 1 0 6 40 1 0 7 41 1 1 8 42 1 6 9 43 1 0 9 44 1 0 10 45 1 0 10 46 1 0 13 47 1 0 13 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 18 53 1 0 19 54 1 0 19 55 1 0 20 56 1 6 22 57 1 0 22 58 1 0 22 59 1 0 23 60 1 0 23 61 1 0 24 62 1 0 24 63 1 0 25 64 1 6 27 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 M END

Standard InCHIKey	AOXXVRDKZLRGTJ-AZIDVCJLSA-N
Standard InCHI	InChI=1S/C30H48O2/c1-20(19-31)9-8-10-21(2)22-13-17-30(7)24-11-12-25-27(3,4)26(32)15-16-28(25,5)23(24)14-18-29(22,30)6/h9,11,14,21-22,25-26,31-32H,8,10,12-13,15-19H2,1-7H3/b20-9+/t21-,22-,25+,26+,28-,29-,30+/m1/s1
SMILES	OC/C(=C/CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.37	Volume:	502.881 ? Van der Waals volume.
Dense:	0.876	LogP:	6.237 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.568 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.698 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.443	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.845	Fsp³:	0.8
MCE-18:	76.926 ? 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:	0.826	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.643	Promiscuous compounds:	0.11

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.993	MDCK Permeability:	-4.849
Pgp-inhibitor:	0.82	Pgp-substrate:	0.045
PAMPA:	0.524 ? 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%):	0.198	30% Bioavailability (F30%):	0.237
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176	MRP1:	0.297
Plasma Protein Binding (PPB):	88.599%	Volume Distribution (VD):	-0.07
Fu:	11.188% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.874
BSEP inhibitor:	0.906

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.204
CYP2C19-inhibitor:	0.627	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.632
CYP2D6-inhibitor:	0.024	CYP2D6-substrate:	0.684
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.061 ? 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):

12.081

Half-life (T1/2):

0.529

ADMET: Toxicity

hERG Blockers:	0.057	hERG Blockers (10um):	0.235
Human Hepatotoxicity (H-HT):	0.619	Drug-induced Liver Injury (DILI):	0.014
AMES Toxicity:	0.153	Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.241	Skin Sensitization:	0.956
Carcinogencity:	0.507	Eye Corrosion:	0.055
Eye Irritation:	0.902	Respiratory Toxicity:	0.777
Drug-induced Neurotoxicity:	0.037	Ototoxicity:	0.482
Hematotoxicity:	0.155	Drug-induced Nephrotoxicity:	0.374
Genotoxicity:	0.078	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.126	Hek293 Cytotoxicity:	0.34
BCF:	2.346 ? 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:	4.632 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.838 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.4 ? 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]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757736]
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]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[16378363]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378363]
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]
NPO14563	Kalimeris shimadae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804830]
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]
NPO14984	Agelenopsis aperta	Species	Agelenidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11201	Barleria strigosa	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14696	Frullania inflata	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13953	Gouania lupuloides	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14563	Kalimeris shimadae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7245	Lamprometra klunzingeri	Species	Mariametridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15560	Penicillium camemberti	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12787	Phora hyperborea	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12142	Solanum nodiflorum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27375	Sphingomonas paucimobilis	Species	Sphingomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Leaf Diffusate	n.a.	n.a.	Database[FooDB]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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[TM-MC]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14696	Frullania inflata	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7245	Lamprometra klunzingeri	Species	Mariametridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12787	Phora hyperborea	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12142	Solanum nodiflorum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15560	Penicillium camemberti	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14563	Kalimeris shimadae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13953	Gouania lupuloides	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14984	Agelenopsis aperta	Species	Agelenidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11201	Barleria strigosa	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27375	Sphingomonas paucimobilis	Species	Sphingomonadaceae	Bacteria	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
Activity	4
IC50	6
Inhibition	2
Ratio IC50	1

Activity Type	# Activity
Individual protein	3
Cell line	3
Others	4
Non-molecular	1
Organism	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Activity	=	50.0	%	PMID[17499997]
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	IC50	=	26780.0	nM	PMID[21924611]
NPT439	Individual protein	Butyrylcholinesterase	Homo sapiens	IC50	>	200000.0	nM	PMID[21924611]

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	=	101000.0	nM	PMID[23092389]
NPT65	Cell line	HepG2	Homo sapiens	Activity	=	18.97	U/L	PMID[29353722]
NPT65	Cell line	HepG2	Homo sapiens	Activity	=	26.42	U/L	PMID[29353722]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	13720.0	nM	PMID[27335254]
NPT2	Others	Unspecified	n.a.	Inhibition	=	37.0	%	PMID[17499997]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	5.0	n.a.	PMID[24070782]
NPT2	Others	Unspecified	n.a.	IC50	=	110100.0	nM	PMID[24070782]
NPT2	Others	Unspecified	n.a.	IC50	=	119800.0	nM	PMID[26287401]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	49.0	%	PMID[17499997]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	31.0	%	PMID[17499997]

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 NPC202389 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	24712
0.1-0.2	21685
0.2-0.3	3026
0.3-0.4	335
0.4-0.5	60
0.5-0.6	26
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8679	High Similarity	NPC205455
0.7931	Intermediate Similarity	NPC475772
0.7544	Intermediate Similarity	NPC6707
0.7541	Intermediate Similarity	NPC212948
0.6774	Remote Similarity	NPC4166
0.6769	Remote Similarity	NPC469406
0.6515	Remote Similarity	NPC214697
0.6452	Remote Similarity	NPC231310
0.6393	Remote Similarity	NPC147568
0.625	Remote Similarity	NPC311092
0.6066	Remote Similarity	NPC20853
0.6061	Remote Similarity	NPC69454
0.6029	Remote Similarity	NPC48647
0.6	Remote Similarity	NPC484797
0.5857	Remote Similarity	NPC141401
0.5821	Remote Similarity	NPC84271
0.5821	Remote Similarity	NPC102414
0.5806	Remote Similarity	NPC72507
0.5735	Remote Similarity	NPC482597
0.5652	Remote Similarity	NPC138536
0.5556	Remote Similarity	NPC46160
0.5556	Remote Similarity	NPC202642
0.5455	Remote Similarity	NPC201852
0.5429	Remote Similarity	NPC77168
0.5294	Remote Similarity	NPC89077
0.5286	Remote Similarity	NPC69622
0.5286	Remote Similarity	NPC44181
0.5286	Remote Similarity	NPC606857
0.5286	Remote Similarity	NPC607637
0.527	Remote Similarity	NPC39082
0.527	Remote Similarity	NPC610107
0.5231	Remote Similarity	NPC186191
0.5224	Remote Similarity	NPC170793
0.5205	Remote Similarity	NPC478313
0.5205	Remote Similarity	NPC489790
0.5147	Remote Similarity	NPC275740
0.5147	Remote Similarity	NPC86319
0.5143	Remote Similarity	NPC222845
0.5143	Remote Similarity	NPC296577
0.507	Remote Similarity	NPC87552

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC202389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8012
0.1-0.2	1090
0.2-0.3	48
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