NPASS Compound

Natural Product: NPC28252

Natural Product ID	NPC28252
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Eburicoic Acid
IUPAC Name	(2R)-2-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms	Eburicoic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL179188
PubChem CID	73402
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 84 87 0 0 0 0 0 0 0 0999 V2000 -7.5380 -0.6707 -0.9200 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3563 0.8319 -0.9973 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9377 1.2201 -0.7719 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6675 2.0986 0.1627 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8880 0.5742 -1.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4855 0.7174 -1.0274 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3017 0.0164 0.2997 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9513 0.2340 0.8824 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8285 -0.4815 2.2028 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -0.9641 2.2833 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2786 0.0398 1.3548 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7232 -0.0712 0.1810 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7006 -1.4664 -0.3543 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1871 0.8694 -0.8453 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1287 0.2918 -1.3810 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0073 -0.1841 -0.3000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6468 -0.3112 0.9633 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6184 -0.8017 1.9637 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0194 -0.3562 1.7421 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2527 0.2384 0.3759 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4216 -0.5487 -0.6156 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5507 -2.0229 -0.4638 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8186 -0.1744 -2.0106 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2384 -0.5493 -2.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1601 -0.4600 -1.1107 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6657 0.4349 0.0052 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6551 0.3373 1.1395 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8777 1.8679 -0.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5962 -1.7062 -0.6786 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1951 1.3695 2.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6191 -1.4202 0.0510 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6615 -1.8902 -1.1138 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8924 -2.3388 1.0470 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3010 1.5508 -0.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6095 -0.9070 -0.8344 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9456 -1.0268 -0.0536 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1019 -1.1432 -1.8262 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6754 1.1186 -2.0411 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6666 2.4208 0.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4752 2.5307 0.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1707 -0.4641 -1.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9295 1.1000 -2.5991 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8628 0.1027 -1.7476 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2343 1.7746 -1.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0454 0.3754 0.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9695 1.3479 1.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4162 -1.3810 2.3253 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9584 0.1927 3.0859 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0232 -0.8714 3.3154 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2569 -2.0004 1.9706 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2964 -2.1974 0.2287 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3160 -1.9339 -0.3898 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9958 -1.4067 -1.4322 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0808 1.8715 -0.4759 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7859 1.0256 -1.7459 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6051 1.0441 -2.0413 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8828 -0.5794 -2.0208 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2879 -0.3939 2.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4863 -1.8998 2.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6862 -1.2079 1.9854 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3178 0.4513 2.4758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7634 1.2590 0.4293 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1584 -2.3594 0.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5968 -2.5813 -0.3781 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0535 -2.4922 -1.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1735 -0.7847 -2.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6019 0.8804 -2.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3045 -1.5900 -2.6883 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5766 0.0949 -3.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1049 0.0380 -1.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4900 1.2369 1.7943 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6666 0.4460 0.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5852 -0.5324 1.7724 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9538 2.3031 -0.9132 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6389 1.8975 -1.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2498 2.5437 0.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5041 -1.8892 0.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1843 2.2023 1.4768 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2608 1.6653 2.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3044 1.3350 3.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5646 -3.0927 0.9165 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0846 1.3044 0.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2246 2.6362 -0.2753 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3359 1.2614 -0.3395 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 3 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 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 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 1 7 31 1 0 31 32 2 0 31 33 1 0 2 34 1 0 12 8 1 0 21 16 1 0 17 11 1 0 26 20 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 7 45 1 1 8 46 1 1 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 13 51 1 0 13 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 1 22 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 24 69 1 0 25 70 1 6 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 28 76 1 0 29 77 1 0 30 78 1 0 30 79 1 0 30 80 1 0 33 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 M END

Standard InCHIKey	UGMQOYZVOPASJF-OXUZYLMNSA-N
Standard InCHI	InChI=1S/C31H50O3/c1-19(2)20(3)9-10-21(27(33)34)22-13-17-31(8)24-11-12-25-28(4,5)26(32)15-16-29(25,6)23(24)14-18-30(22,31)7/h19,21-22,25-26,32H,3,9-18H2,1-2,4-8H3,(H,33,34)/t21-,22-,25+,26+,29-,30-,31+/m1/s1
SMILES	CC(C(=C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.38	Volume:	528.967 ? Van der Waals volume.
Dense:	0.889	LogP:	4.234 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.33 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.483 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	22.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.389	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.787	Fsp³:	0.839
MCE-18:	83.368 ? 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:	0.956	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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.546	Promiscuous compounds:	0.048

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.156	MDCK Permeability:	-4.789
Pgp-inhibitor:	0.002	Pgp-substrate:	0.011
PAMPA:	0.995 ? 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%):	0.321	30% Bioavailability (F30%):	0.061
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.334	MRP1:	0.999
Plasma Protein Binding (PPB):	92.754%	Volume Distribution (VD):	-0.227
Fu:	4.928% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.136
BSEP inhibitor:	0.929

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.409	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.152	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.483	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.42
HLM stability:	0.005 ? 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):

6.902

Half-life (T1/2):

0.549

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.055
Human Hepatotoxicity (H-HT):	0.583	Drug-induced Liver Injury (DILI):	0.198
AMES Toxicity:	0.248	Rat Oral Acute Toxicity:	0.21
Maximum Recommended Daily Dose:	0.197	Skin Sensitization:	0.992
Carcinogencity:	0.726	Eye Corrosion:	0.337
Eye Irritation:	0.889	Respiratory Toxicity:	0.738
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.626
Hematotoxicity:	0.575	Drug-induced Nephrotoxicity:	0.935
Genotoxicity:	0.149	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.076	Hek293 Cytotoxicity:	0.07
BCF:	1.735 ? 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:	4.374 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.747 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.191 ? 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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738384]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620242]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO33546	Poria coco	Species	n.a.	Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17932820]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19842686]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO425	Streptomyces cattleya	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21263049]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO10876	Euphorbia granulata	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23580316]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO425	Streptomyces cattleya	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26240322]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891260]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[8594142]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO425	Streptomyces cattleya	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11551	Paliurus ramosissimus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10400	Pothos chinensis	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11551	Paliurus ramosissimus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10400	Pothos chinensis	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10876	Euphorbia granulata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12593	Plectranthus grandidentatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3205	Dracocephalum heterophyllum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6217	Castanopsis fissa	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13911	Eunicella stricta	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO425	Streptomyces cattleya	Species	Streptomycetaceae	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
GI50	1
Inhibition	4
Activity	1
IC50	5

Activity Type	# Activity
Cell line	7
Organism	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
NPT517	Cell line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	10000.0	nM	PMID[15743190]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[17488130]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	25000.0	nM	PMID[23092389]
NPT380	Cell line	U-251	Homo sapiens	IC50	>	100000.0	nM	PMID[31891260]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[31891260]
NPT660	Cell line	SW480	Homo sapiens	IC50	>	100000.0	nM	PMID[31891260]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	9.1	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	45.8	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	75.3	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	100.0	%	PMID[17488130]

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 NPC28252 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	22502
0.1-0.2	23956
0.2-0.3	3018
0.3-0.4	275
0.4-0.5	56
0.5-0.6	33
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC55309
0.8448	Intermediate Similarity	NPC469400
0.7833	Intermediate Similarity	NPC233836
0.7833	Intermediate Similarity	NPC159046
0.7833	Intermediate Similarity	NPC187376
0.7541	Intermediate Similarity	NPC482908
0.7541	Intermediate Similarity	NPC48330
0.7541	Intermediate Similarity	NPC23434
0.6769	Remote Similarity	NPC474889
0.6667	Remote Similarity	NPC77168
0.6462	Remote Similarity	NPC484974
0.623	Remote Similarity	NPC118508
0.6032	Remote Similarity	NPC73875
0.5942	Remote Similarity	NPC484976
0.5882	Remote Similarity	NPC76895
0.5882	Remote Similarity	NPC173272
0.5857	Remote Similarity	NPC482518
0.5797	Remote Similarity	NPC289213
0.5556	Remote Similarity	NPC606082
0.5493	Remote Similarity	NPC206810
0.5493	Remote Similarity	NPC203035
0.5479	Remote Similarity	NPC184848
0.5469	Remote Similarity	NPC484086
0.5373	Remote Similarity	NPC471724
0.5352	Remote Similarity	NPC54689
0.5286	Remote Similarity	NPC242864
0.5278	Remote Similarity	NPC148414
0.5278	Remote Similarity	NPC45324
0.5278	Remote Similarity	NPC162001
0.5278	Remote Similarity	NPC111585
0.5278	Remote Similarity	NPC175628
0.5224	Remote Similarity	NPC132635
0.5224	Remote Similarity	NPC601223
0.5211	Remote Similarity	NPC84271
0.5211	Remote Similarity	NPC102414
0.5152	Remote Similarity	NPC275910
0.5152	Remote Similarity	NPC46160
0.5152	Remote Similarity	NPC202642
0.5143	Remote Similarity	NPC201912
0.5143	Remote Similarity	NPC38350
0.5143	Remote Similarity	NPC601139
0.5075	Remote Similarity	NPC231477
0.5075	Remote Similarity	NPC87489
0.5075	Remote Similarity	NPC123724
0.5072	Remote Similarity	NPC171789
0.5072	Remote Similarity	NPC94755

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC28252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6518
0.1-0.2	2573
0.2-0.3	56
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