NPASS Compound

Natural Product: NPC96916

Natural Product ID	NPC96916
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Arjunic Acid
IUPAC Name	(1S,4aR,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-1,10,11-trihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	Arjunic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL515705
PubChem CID	15385516
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 82 86 0 0 0 0 0 0 0 0999 V2000 -4.5294 -2.2013 -1.3587 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9127 -0.8338 -0.7618 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4157 -1.0195 -0.4638 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8026 0.1653 -1.8257 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7848 1.2522 -1.7047 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5793 1.6098 -0.2996 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6145 2.7431 -0.0482 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3421 2.3622 0.6597 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6842 1.2023 0.0306 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2898 1.6170 -1.3715 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7159 0.0881 0.0241 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2288 -1.0805 -0.3482 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1785 -1.3605 -0.7368 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1350 -0.3182 -0.2643 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4891 -0.8414 0.1177 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5744 -1.8178 1.1983 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9703 -1.5540 -1.1637 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4256 -1.8589 -1.1497 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3010 -0.6785 -0.8642 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8271 0.1328 0.3229 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4693 1.5222 0.1258 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3415 -0.3811 1.6223 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3540 0.3740 0.2363 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8773 1.3783 1.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4357 1.6049 1.3311 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4944 0.6020 0.7657 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0333 -0.2927 1.8975 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6040 -1.1151 -0.6797 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7480 -2.2871 -2.4585 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0682 0.4115 0.4507 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1067 -0.6379 0.4739 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6980 -1.8345 1.0627 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8801 1.9803 0.3228 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8900 2.1103 -0.3650 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9339 2.1756 1.6851 O 0 0 0 0 0 1 0 0 0 0 0 0 -5.3611 -2.5639 -1.9614 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1917 -2.8985 -0.5639 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6418 -1.9634 -2.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0358 -0.6271 -1.2835 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5974 -0.4354 0.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6819 -2.0499 -0.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5853 -0.3347 -2.8373 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7928 0.6625 -2.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1603 2.1585 -2.2622 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8752 0.8701 -2.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4852 3.4247 -0.9118 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1278 3.4195 0.7031 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6819 3.2736 0.5461 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5020 2.2619 1.7542 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3549 0.8019 -2.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6652 2.1722 -1.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0204 2.3743 -1.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9133 -1.9018 -0.3645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4758 -2.3977 -0.3812 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2039 -1.4839 -1.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3815 0.2998 -1.1872 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6251 -2.2430 1.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4539 -1.4705 2.2315 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9543 -2.7038 0.9561 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6535 -1.0241 -2.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4245 -2.5413 -1.1456 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6832 -2.7330 -0.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2994 -0.0246 -1.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4334 2.0507 1.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8678 2.0785 -0.5933 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5388 1.3881 -0.1872 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1872 0.2427 2.0436 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6216 -0.4714 2.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8514 -1.3656 1.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2234 0.8781 -0.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4178 2.3522 1.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3184 1.0643 2.2233 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1823 1.7840 2.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1960 2.5968 0.8663 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6135 -0.0871 2.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1246 -1.3524 1.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0110 -0.1123 2.1992 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8787 -1.6166 -1.4947 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3579 -3.2037 -2.5977 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0542 0.8761 1.5102 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8920 -0.2887 1.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4489 -2.3554 1.4220 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 19 28 1 0 18 29 1 0 11 30 1 0 30 31 1 0 31 32 1 0 6 33 1 1 33 34 2 0 33 35 1 0 31 2 1 0 30 6 1 0 26 9 1 0 26 14 1 0 23 15 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 10 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 6 16 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 1 19 63 1 6 21 64 1 0 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 22 69 1 0 23 70 1 6 24 71 1 0 24 72 1 0 25 73 1 0 25 74 1 0 27 75 1 0 27 76 1 0 27 77 1 0 28 78 1 0 29 79 1 0 30 80 1 1 31 81 1 1 32 82 1 0 M CHG 1 35 -1 M END

Standard InCHIKey	XJMYUPJDAFKICJ-YZTGESMESA-N
Standard InCHI	InChI=1S/C30H48O5/c1-25(2)12-14-30(24(34)35)15-13-28(6)17(21(30)23(25)33)8-9-20-27(5)16-18(31)22(32)26(3,4)19(27)10-11-29(20,28)7/h8,18-23,31-33H,9-16H2,1-7H3,(H,34,35)/p-1/t18-,19+,20-,21-,22+,23+,27+,28-,29-,30+/m1/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@@H]1O)C(=O)[O-]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	2.869 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.792 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.55 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.382	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.964	Fsp³:	0.9
MCE-18:	110.772 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.836	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.05 ? 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:	0.308	Promiscuous compounds:	0.092

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.6	MDCK Permeability:	-5.109
Pgp-inhibitor:	0.0	Pgp-substrate:	0.106
PAMPA:	1.0 ? 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):	0.012
20% Bioavailability (F20%):	0.7	30% Bioavailability (F30%):	0.315
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416	MRP1:	0.987
Plasma Protein Binding (PPB):	88.363%	Volume Distribution (VD):	-0.213
Fu:	10.524% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.957	BCRP inhibitor:	0.002
BSEP inhibitor:	0.667

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.021
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.006
HLM stability:	0.016 ? 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):

3.461

Half-life (T1/2):

1.125

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.04
Human Hepatotoxicity (H-HT):	0.582	Drug-induced Liver Injury (DILI):	0.564
AMES Toxicity:	0.395	Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.178	Skin Sensitization:	0.882
Carcinogencity:	0.687	Eye Corrosion:	0.004
Eye Irritation:	0.449	Respiratory Toxicity:	0.691
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.811
Hematotoxicity:	0.519	Drug-induced Nephrotoxicity:	0.941
Genotoxicity:	0.42	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.122	Hek293 Cytotoxicity:	0.077
BCF:	1.061 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.573 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.157 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.423 ? 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
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/np50070a005]
NPO18280	Colubrina retusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10346942]
NPO18280	Colubrina retusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10514332]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473413]
NPO19499	Plocamium corallorhiza	Species	Plocamiaceae	Eukaryota	n.a.	South African	n.a.	PMID[17343409]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	leaves	Botanical Garden of Innsbruck, Austria	n.a.	PMID[20100662]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21923134]
NPO11213	Terminalia arjuna	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39034926]
NPO20674	Pseudopterogorgia rigida	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9090873]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]
NPO13314	Callitropsis funebris	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19988	Vinca herbacea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20674	Pseudopterogorgia rigida	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22468	Parazoanthus gracilis	Species	Parazoanthidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18112	Melochia chamaedrys	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11213	Terminalia arjuna	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26422	Rubus chingii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19499	Plocamium corallorhiza	Species	Plocamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19988	Vinca herbacea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11213	Terminalia arjuna	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11213	Terminalia arjuna	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13314	Callitropsis funebris	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19988	Vinca herbacea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26422	Rubus chingii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22699	Echinops setifer	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26422	Rubus chingii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4163	Echinopsis latifolius	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18280	Colubrina retusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20674	Pseudopterogorgia rigida	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20615	Osmites hirsuta	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20217	Vernonanthura squamulosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19499	Plocamium corallorhiza	Species	Plocamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20550	Helenium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19988	Vinca herbacea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12448	Simplicillium lamellicola	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18639	Breynia vitis-idaea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22468	Parazoanthus gracilis	Species	Parazoanthidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18112	Melochia chamaedrys	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26422	Rubus chingii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13314	Callitropsis funebris	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	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	3

Activity Type	# Activity
Individual protein	1
Cell line	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3809	Individual protein	Pancreatic alpha-amylase	Sus scrofa	Inhibition	=	6.2	%	PMID[27890380]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell line	Hepatocyte	Mus musculus	Activity	=	27.8	%	PMID[11277757]
NPT993	Cell line	Hepatocyte	Mus musculus	Activity	=	26.6	%	PMID[11277757]
NPT993	Cell line	Hepatocyte	Mus musculus	Activity	=	26.5	%	PMID[11277757]
NPT993	Cell line	Hepatocyte	Mus musculus	Inhibition	=	32.9	%	PMID[11277757]
NPT993	Cell line	Hepatocyte	Mus musculus	Inhibition	=	27.0	%	PMID[11277757]
NPT993	Cell line	Hepatocyte	Mus musculus	Inhibition	=	26.7	%	PMID[11277757]

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 NPC96916 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	27030
0.1-0.2	20311
0.2-0.3	2058
0.3-0.4	328
0.4-0.5	92
0.5-0.6	19
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7344	Intermediate Similarity	NPC306541
0.7231	Intermediate Similarity	NPC300351
0.6471	Remote Similarity	NPC173744
0.6471	Remote Similarity	NPC204961
0.6471	Remote Similarity	NPC73004
0.6143	Remote Similarity	NPC145667
0.6087	Remote Similarity	NPC84319
0.6087	Remote Similarity	NPC52021
0.6087	Remote Similarity	NPC599947
0.6056	Remote Similarity	NPC9613
0.6029	Remote Similarity	NPC43686
0.6	Remote Similarity	NPC472149
0.6	Remote Similarity	NPC71074
0.6	Remote Similarity	NPC37221
0.6	Remote Similarity	NPC605937
0.5915	Remote Similarity	NPC259733
0.5915	Remote Similarity	NPC158371
0.5915	Remote Similarity	NPC207922
0.5753	Remote Similarity	NPC25299
0.5753	Remote Similarity	NPC481322
0.5714	Remote Similarity	NPC187722
0.5556	Remote Similarity	NPC111214
0.5417	Remote Similarity	NPC195019
0.5278	Remote Similarity	NPC136313
0.5205	Remote Similarity	NPC229281
0.5135	Remote Similarity	NPC231063
0.5135	Remote Similarity	NPC38754
0.5135	Remote Similarity	NPC282395
0.5135	Remote Similarity	NPC88116
0.5135	Remote Similarity	NPC110308
0.5135	Remote Similarity	NPC609452
0.5067	Remote Similarity	NPC32407
0.5067	Remote Similarity	NPC263548
0.5067	Remote Similarity	NPC606320

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC96916 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7583
0.1-0.2	1547
0.2-0.3	18
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