NPASS Compound

Natural Product: NPC77168

Natural Product ID	NPC77168
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dehydroeburicoic Acid
IUPAC Name	(2R)-2-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms	Dehydroeburicoic Acid; Dehydroeburicoicacid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1744446
PubChem CID	15250826
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000260] Monohydroxy bile acids, alcohols and derivatives

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 7.2303 -1.8770 -0.9361 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3885 -0.3846 -0.6630 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7136 0.3972 -1.7338 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8936 -0.1614 0.7113 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7605 0.3296 1.5932 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5329 -0.4742 1.1655 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4296 0.2674 0.4931 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0399 -0.0863 0.9937 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9678 0.7049 0.2606 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1024 0.4004 -1.2533 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7348 0.0028 -1.7369 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1553 0.6045 -0.7261 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2464 2.0859 -0.8895 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4857 -0.0287 -0.6180 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9640 -0.9298 -1.4571 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3452 -1.4426 -1.1577 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1615 -0.2187 -0.8305 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6331 -0.4209 -1.0110 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1266 -1.7218 -0.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8742 -0.5256 -2.5254 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4537 0.7017 -0.5090 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9179 1.4768 0.6309 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4338 1.6837 0.6433 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7841 0.3430 0.5010 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1658 -0.5625 1.6499 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2781 0.4203 0.5249 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6363 0.8879 1.5745 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1339 0.9862 1.6658 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5807 0.2752 0.5823 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5163 -1.2182 0.8387 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7097 0.1814 -0.1191 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0163 0.2486 2.4254 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5563 1.3616 2.7958 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5022 -0.6783 3.3470 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9537 -2.4477 -0.0278 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4538 -2.0220 -1.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2051 -2.3161 -1.2746 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4940 -0.1535 -0.7070 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5265 0.7504 -2.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0363 -0.2232 -2.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2764 1.3329 -1.3633 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4269 0.5026 2.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7903 0.5674 1.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4156 -1.5921 1.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4165 -0.3101 2.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5043 -0.0115 -0.6013 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5134 1.3592 0.5670 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9245 -1.1770 0.8195 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0974 1.7649 0.4820 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4758 1.3074 -1.7569 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7524 -0.4835 -1.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6190 -1.0957 -1.8123 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5292 0.4612 -2.7337 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2298 2.6704 -0.1005 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3398 2.3609 -0.8706 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2077 2.4381 -1.8587 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3624 -1.2337 -2.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7838 -1.9221 -2.0434 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2659 -2.1636 -0.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8563 0.5590 -1.5933 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6105 -2.3839 -1.1666 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3133 -2.3232 0.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9582 -1.5287 0.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0132 -0.1911 -3.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0649 -1.5974 -2.8116 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7579 0.0384 -2.8382 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7019 1.4161 -1.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3813 2.5070 0.6006 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2911 1.0537 1.6089 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1767 2.3023 -0.2425 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1671 2.1711 1.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2381 -0.6836 1.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6364 -1.5298 1.5593 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7713 -0.0872 2.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2143 1.2175 2.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1481 2.0370 1.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0823 0.4429 2.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5360 -1.5119 0.9226 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9801 -1.3749 1.8444 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0936 -1.7965 0.1064 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4476 0.7859 -0.3667 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2753 -0.5151 4.3102 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 1 21 31 1 0 8 32 1 0 32 33 2 0 32 34 1 0 29 9 1 0 29 12 1 0 26 14 1 0 24 17 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 1 9 49 1 6 10 50 1 0 10 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 13 55 1 0 13 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 6 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 20 66 1 0 21 67 1 6 22 68 1 0 22 69 1 0 23 70 1 0 23 71 1 0 25 72 1 0 25 73 1 0 25 74 1 0 27 75 1 0 28 76 1 0 28 77 1 0 30 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 34 82 1 0 M END

Standard InCHIKey	ONFPYGOMAADWAT-OXUZYLMNSA-N
Standard InCHI	InChI=1S/C31H48O3/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/h11,14,19,21-22,25-26,32H,3,9-10,12-13,15-18H2,1-2,4-8H3,(H,33,34)/t21-,22-,25+,26+,29-,30-,31+/m1/s1
SMILES	CC(C)C(=C)CC[C@H]([C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.36	Volume:	526.331 ? Van der Waals volume.
Dense:	0.89	LogP:	5.279 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.915 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.61 ? 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:	0.395	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.935	Fsp³:	0.774
MCE-18:	81.6 ? 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:	0.788	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? 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:	0.531	Promiscuous compounds:	0.045

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.168	MDCK Permeability:	-4.805
Pgp-inhibitor:	0.003	Pgp-substrate:	0.024
PAMPA:	0.982 ? 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%):	0.065	30% Bioavailability (F30%):	0.031
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.263	MRP1:	0.99
Plasma Protein Binding (PPB):	90.964%	Volume Distribution (VD):	-0.252
Fu:	7.024% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.597
BSEP inhibitor:	0.938

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.027	CYP2C19-substrate:	0.025
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.077 ? 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):

8.27

Half-life (T1/2):

0.629

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.095
Human Hepatotoxicity (H-HT):	0.499	Drug-induced Liver Injury (DILI):	0.081
AMES Toxicity:	0.133	Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.3	Skin Sensitization:	0.921
Carcinogencity:	0.458	Eye Corrosion:	0.05
Eye Irritation:	0.732	Respiratory Toxicity:	0.45
Drug-induced Neurotoxicity:	0.027	Ototoxicity:	0.662
Hematotoxicity:	0.272	Drug-induced Nephrotoxicity:	0.689
Genotoxicity:	0.305	RPMI-8226 Immunitoxicity:	0.1
A549 Cytotoxicity:	0.024	Hek293 Cytotoxicity:	0.085
BCF:	1.495 ? 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:	4.102 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.644 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.967 ? 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]
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]
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[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
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]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6117	Poria	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30645	Poria 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]
NPO13791	Litsea turfosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13791	Litsea turfosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO6117	Poria	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13791	Litsea turfosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13791	Litsea turfosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31476	Fornes officinalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13791	Litsea turfosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14403	Taiwanofungus camphoratus	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]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	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
Inhibition	4
Activity	2
IC50	8

Activity Type	# Activity
Cell line	9
Organism	4
Others	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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[17488130]
NPT111	Cell line	K562	Homo sapiens	IC50	=	25600.0	nM	PMID[27808511]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	6000.0	nM	PMID[27808511]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	=	6300.0	nM	PMID[27808511]
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	=	14300.0	nM	PMID[27808511]
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]
NPT737	Cell line	HUVEC	Homo sapiens	Activity	=	69.8	%	PMID[31891260]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	8.7	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	45.1	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	74.9	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	100.0	%	PMID[17488130]
NPT2	Others	Unspecified	n.a.	IC50	=	77500.0	nM	PMID[17559265]

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 NPC77168 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	21153
0.1-0.2	24467
0.2-0.3	3783
0.3-0.4	348
0.4-0.5	56
0.5-0.6	34
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8065	Intermediate Similarity	NPC84271
0.8065	Intermediate Similarity	NPC102414
0.7692	Intermediate Similarity	NPC469406
0.7538	Intermediate Similarity	NPC45324
0.7538	Intermediate Similarity	NPC162001
0.7538	Intermediate Similarity	NPC203035
0.6912	Remote Similarity	NPC477812
0.6866	Remote Similarity	NPC69279
0.6812	Remote Similarity	NPC484968
0.6667	Remote Similarity	NPC55309
0.6667	Remote Similarity	NPC28252
0.6429	Remote Similarity	NPC186810
0.6338	Remote Similarity	NPC484967
0.6286	Remote Similarity	NPC296367
0.6143	Remote Similarity	NPC212948
0.6	Remote Similarity	NPC222845
0.6	Remote Similarity	NPC296577
0.5753	Remote Similarity	NPC484975
0.5753	Remote Similarity	NPC48647
0.5753	Remote Similarity	NPC214697
0.5753	Remote Similarity	NPC321301
0.5672	Remote Similarity	NPC205455
0.5658	Remote Similarity	NPC288464
0.5658	Remote Similarity	NPC477813
0.5658	Remote Similarity	NPC607198
0.5652	Remote Similarity	NPC201852
0.5634	Remote Similarity	NPC233836
0.5634	Remote Similarity	NPC159046
0.5634	Remote Similarity	NPC48330
0.5634	Remote Similarity	NPC469400
0.5634	Remote Similarity	NPC187376
0.5616	Remote Similarity	NPC310470
0.56	Remote Similarity	NPC141401
0.5588	Remote Similarity	NPC6707
0.5541	Remote Similarity	NPC608955
0.5526	Remote Similarity	NPC263347
0.5522	Remote Similarity	NPC72507
0.5493	Remote Similarity	NPC475772
0.5467	Remote Similarity	NPC152897
0.5429	Remote Similarity	NPC202389
0.5417	Remote Similarity	NPC83569
0.5417	Remote Similarity	NPC23434
0.5333	Remote Similarity	NPC482518
0.5211	Remote Similarity	NPC231310
0.5205	Remote Similarity	NPC482908
0.52	Remote Similarity	NPC138536
0.5072	Remote Similarity	NPC20853
0.5068	Remote Similarity	NPC196827
0.5067	Remote Similarity	NPC142361
0.5067	Remote Similarity	NPC474684
0.5065	Remote Similarity	NPC123854

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC77168 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6617
0.1-0.2	2471
0.2-0.3	60
0.3-0.4	2
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