NPASS Compound

Natural Product: NPC270511

Natural Product ID	NPC270511
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FWPYIYVSYQRISA-LEOBWYFPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL449356
PubChem CID	11112737
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

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 73 77 0 0 0 0 0 0 0 0999 V2000 -7.8947 1.9803 -0.0937 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5326 1.7762 0.0067 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2111 1.4566 1.4486 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7666 1.1913 1.6856 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2775 0.0718 0.7933 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5926 0.4696 -0.6343 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0680 0.5994 -0.8184 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9646 1.7026 -0.8392 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6826 1.6864 -0.7076 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1317 0.4261 -0.4557 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7683 -0.0074 0.8342 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0864 -0.4060 1.8726 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5994 -0.4750 1.8887 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0626 -0.6623 0.4846 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6865 0.4618 -0.3301 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1167 0.4213 -1.5852 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5315 0.3539 -0.9900 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3682 -0.3460 0.3478 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3806 -1.3887 0.4551 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7287 -0.7063 0.2622 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4822 -0.9291 -0.7708 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7849 -0.2453 -0.9233 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1243 0.7433 0.1449 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1871 1.8960 0.2765 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5306 1.2570 -0.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8750 -1.3098 -0.9462 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4906 -2.1491 1.7317 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4936 -2.0134 0.0091 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6412 -0.4379 -1.5907 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9727 -0.4700 -1.6149 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8311 -1.2538 1.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0662 2.9286 -0.3886 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9827 2.6669 -0.3568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8822 0.6522 1.7682 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4852 2.3753 2.0383 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6316 0.9255 2.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1905 2.1044 1.4448 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3122 0.7125 -1.8908 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5456 -0.3303 -0.4040 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6182 -0.7042 2.7742 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2703 -1.2742 2.5778 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2210 0.5226 2.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3896 1.4087 0.2099 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0179 1.3712 -2.1484 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0258 -0.4568 -2.2112 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8751 1.3828 -0.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2114 -0.1801 -1.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5907 0.4512 1.1210 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3209 -2.1265 -0.3710 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9856 -0.0416 1.0683 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1079 -1.6389 -1.5113 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8139 0.3341 -1.8956 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2350 0.2650 1.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2761 1.8291 -0.3652 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7082 2.8306 -0.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9759 2.1046 1.3336 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7390 2.2012 0.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5507 1.4113 -1.2746 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2680 0.4637 0.0622 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8211 -0.9181 -1.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5065 -2.2029 -1.4902 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0679 -1.6309 0.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5433 -2.4968 1.8401 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9111 -3.1206 1.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2847 -1.5501 2.6345 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6249 -2.0205 -0.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2598 -2.7768 0.7812 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1796 -2.2754 -1.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0028 -0.9472 -2.2725 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5356 -1.1093 -2.2754 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1922 -1.8534 0.3113 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0513 -1.8598 1.6834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6446 -1.1211 1.9400 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 1 6 8 1 0 8 9 1 0 10 9 1 6 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 22 26 1 0 19 27 1 0 14 28 1 6 10 29 1 0 29 30 2 0 5 31 1 1 7 2 1 0 15 10 1 0 11 5 1 0 18 14 1 0 30 6 1 0 1 32 1 0 2 33 1 6 3 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 7 38 1 0 7 39 1 0 12 40 1 0 13 41 1 0 13 42 1 0 15 43 1 1 16 44 1 0 16 45 1 0 17 46 1 0 17 47 1 0 18 48 1 1 19 49 1 6 20 50 1 0 21 51 1 0 22 52 1 6 23 53 1 0 24 54 1 0 24 55 1 0 24 56 1 0 25 57 1 0 25 58 1 0 25 59 1 0 26 60 1 0 26 61 1 0 26 62 1 0 27 63 1 0 27 64 1 0 27 65 1 0 28 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 30 70 1 0 31 71 1 0 31 72 1 0 31 73 1 0 M END

Standard InCHIKey	FWPYIYVSYQRISA-LEOBWYFPSA-N
Standard InCHI	InChI=1S/C28H42O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,12,15-16,18-23,29H,9-11,13-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,25+,26+,27+,28-/m0/s1
SMILES	O[C@H]1CC[C@]2([C@@]3(C1)OO[C@@]1(C2=CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C=C3)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.31	Volume:	468.523 ? Van der Waals volume.
Dense:	0.91	LogP:	4.643 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.932 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.163 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	38.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.418	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.885	Fsp³:	0.786
MCE-18:	119.68 ? 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:	0.915	Fluc inhibitor:	0.016 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.378	Promiscuous compounds:	0.103

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.271	MDCK Permeability:	-4.968
Pgp-inhibitor:	0.844	Pgp-substrate:	0.001
PAMPA:	0.004 ? 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%):	0.945	30% Bioavailability (F30%):	0.982
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.195
Plasma Protein Binding (PPB):	98.925%	Volume Distribution (VD):	-0.051
Fu:	0.785% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.024
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.011
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.009	CYP2D6-substrate:	0.836
CYP3A4-inhibitor:	0.858	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.977 ? 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):

12.751

Half-life (T1/2):

0.832

ADMET: Toxicity

hERG Blockers:	0.092	hERG Blockers (10um):	0.263
Human Hepatotoxicity (H-HT):	0.406	Drug-induced Liver Injury (DILI):	0.112
AMES Toxicity:	0.305	Rat Oral Acute Toxicity:	0.479
Maximum Recommended Daily Dose:	0.824	Skin Sensitization:	0.938
Carcinogencity:	0.864	Eye Corrosion:	0.001
Eye Irritation:	0.411	Respiratory Toxicity:	0.757
Drug-induced Neurotoxicity:	0.044	Ototoxicity:	0.714
Hematotoxicity:	0.139	Drug-induced Nephrotoxicity:	0.433
Genotoxicity:	0.162	RPMI-8226 Immunitoxicity:	0.209
A549 Cytotoxicity:	0.335	Hek293 Cytotoxicity:	0.671
BCF:	2.702 ? 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:	4.214 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.106 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.893 ? 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]
NPO21301	Stereum hirsutum	Species	Stereaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12003003]
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]
NPO21558	Ormosia sumatrana	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15568789]
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]
NPO19990	Axinyssa isabela	Species	Halichondriidae	Eukaryota	n.a.	Isla Isabel (Gulf of California, Mexico)	n.a.	PMID[19007287]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	fresh leaves	n.a.	n.a.	PMID[19778089]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	fresh fruits	n.a.	n.a.	PMID[20092288]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	whole plant	Cholistan desert near district Bahawalpur (Punjab), Pakistan	2003-Oct	PMID[20542692]
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]
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22413887]
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23511021]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25565282]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	Mycelia	n.a.	n.a.	PMID[26807743]
NPO40805	Calvatia nipponica	Species	n.a.	n.a.	Fruiting Bodies	n.a.	n.a.	PMID[32940037]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	Fruiting Bodies	n.a.	n.a.	PMID[33246107]
NPO19796	Azolla filiculoides	Species	Azollaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37765393]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO4994	Pachysandra procumbens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784163]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19907	Helicobasidium mompa	Species	Helicobasidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18460	Trema dielsiana	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19031	Thymus marschallianus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20747	Stictocardia campanulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21301	Stereum hirsutum	Species	Stereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21431	Rapanea laetevirens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18857	Pteronia eenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13404	Plantago subulata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4994	Pachysandra procumbens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21558	Ormosia sumatrana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21490	Hypoxylon fragiforme	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18114	Cyclamen repandum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20485	Cussonia arborea	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20276	Burasaia madagascariensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21238	Berberis tabiensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19796	Azolla filiculoides	Species	Azollaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19990	Axinyssa isabela	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24508	Aspergillus brunneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17541	Andryala pinnatifida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18460	Trema dielsiana	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18460	Trema dielsiana	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21301	Stereum hirsutum	Species	Stereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1493	Hericium erinaceus	Species	Hericiaceae	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]
NPO17541	Andryala pinnatifida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21238	Berberis tabiensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13404	Plantago subulata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24508	Aspergillus brunneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21558	Ormosia sumatrana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19990	Axinyssa isabela	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19031	Thymus marschallianus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19796	Azolla filiculoides	Species	Azollaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19907	Helicobasidium mompa	Species	Helicobasidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18114	Cyclamen repandum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4994	Pachysandra procumbens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21431	Rapanea laetevirens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21301	Stereum hirsutum	Species	Stereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18857	Pteronia eenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20485	Cussonia arborea	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20276	Burasaia madagascariensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18460	Trema dielsiana	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20747	Stictocardia campanulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21490	Hypoxylon fragiforme	Species	Xylariaceae	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
MIC	6
IC50	5

Activity Type	# Activity
Cell line	4
Organism	6
Non-molecular	1

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
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	7.32	ug.mL-1	PMID[23511021]
NPT81	Cell line	A549	Homo sapiens	IC50	=	10.37	ug.mL-1	PMID[23511021]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	9.18	ug.mL-1	PMID[23511021]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	7.73	ug.mL-1	PMID[23511021]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	16.0	ug.mL-1	PMID[17869507]
NPT787	Organism	Candida	Candida	MIC	>	512.0	ug.mL-1	PMID[17869507]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	100.0	ug.mL-1	PMID[20542692]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	15.52	ug.mL-1	PMID[23511021]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	512.0	ug.mL-1	PMID[17869507]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	512.0	ug.mL-1	PMID[17869507]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	512.0	ug.mL-1	PMID[17869507]

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 NPC270511 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	20686
0.1-0.2	27263
0.2-0.3	1808
0.3-0.4	86
0.4-0.5	6
0.5-0.6	4
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC470390
0.875	High Similarity	NPC245410
0.8596	High Similarity	NPC14380
0.75	Intermediate Similarity	NPC192437
0.6129	Remote Similarity	NPC475025
0.5938	Remote Similarity	NPC475027
0.5714	Remote Similarity	NPC4574
0.5303	Remote Similarity	NPC212596
0.5147	Remote Similarity	NPC101886

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC270511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7217
0.1-0.2	1828
0.2-0.3	98
0.3-0.4	7
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