NPASS Compound

Natural Product: NPC246708

Natural Product ID	NPC246708
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl Oleanolate
IUPAC Name	methyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	Methyl Oleanolate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL487412
PubChem CID	92900
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 88 0 0 0 0 0 0 0 0999 V2000 -5.0680 -3.3404 -0.8408 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5902 -2.1946 0.0153 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6538 -2.6582 1.4571 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4265 -0.9632 -0.1092 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7810 0.1018 -0.9472 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4342 0.5340 -0.3477 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6517 1.1159 -1.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3212 1.5679 -1.0136 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5200 0.3728 -0.5517 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1949 -0.4385 -1.7884 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2880 -0.4446 0.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6826 -1.0467 1.4289 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7730 -1.0315 1.7335 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4693 -0.4259 0.5344 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9546 -0.3406 0.6959 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4004 0.0858 2.0679 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4948 -1.7684 0.5224 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2883 -1.9102 -0.7553 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4528 -0.9481 -0.7260 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9902 0.4826 -0.5729 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7499 1.2480 0.4388 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2526 1.1368 -1.9418 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5023 0.4800 -0.4115 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9308 1.8887 -0.3456 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4724 1.7533 -0.7271 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7419 0.8197 0.1897 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2572 1.6193 1.3689 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2538 -1.3277 0.3674 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7678 -0.6051 0.3423 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1488 -1.8828 -0.3776 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7652 1.6554 0.5837 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5139 1.5917 1.8005 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3691 2.8075 0.1009 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7070 3.9034 0.9328 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0921 -3.0553 -1.9097 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0523 -3.7012 -0.4820 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3571 -4.1847 -0.6615 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4665 -3.3791 1.6352 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8747 -1.7785 2.1191 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7165 -3.1166 1.7853 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6541 -0.5287 0.8912 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3771 -1.2341 -0.5819 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4481 0.9784 -0.9971 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6384 -0.2558 -1.9924 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2580 1.9771 -1.8696 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6599 0.3726 -2.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7612 1.9940 -1.8947 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4512 2.3284 -0.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5611 -1.4896 -1.6940 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7251 -0.0477 -2.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8721 -0.3996 -2.0838 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2850 -1.6441 2.1423 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8756 -0.4059 2.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1214 -2.0621 1.9331 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2970 -1.1963 -0.2788 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2244 1.1200 2.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8897 -0.5636 2.8078 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4919 -0.1804 2.1910 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1414 -2.0859 1.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6705 -2.5146 0.4608 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7408 -2.9371 -0.7085 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6944 -1.8764 -1.6647 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0499 -1.1262 -1.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4314 0.5223 0.9734 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4809 1.9659 -0.0413 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1604 1.8627 1.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4369 2.2376 -1.7930 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0922 0.6591 -2.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3650 1.0631 -2.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1043 0.0495 -1.3624 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4246 2.5711 -1.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9611 2.3050 0.6746 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0339 2.7809 -0.6024 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4121 1.5301 -1.7892 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8824 1.5888 2.2532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7784 1.3869 1.6803 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2100 2.7046 1.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2015 -1.4680 0.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2108 -0.6894 1.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0952 -1.8015 -1.4656 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5454 -2.7495 -0.0408 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4348 4.5289 0.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7879 4.5248 1.0552 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1352 3.5819 1.8931 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 11 29 1 0 29 30 1 0 6 31 1 1 31 32 2 0 31 33 1 0 33 34 1 0 30 2 1 0 29 6 1 0 26 9 1 0 26 14 1 0 23 15 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 7 45 1 0 7 46 1 0 8 47 1 0 8 48 1 0 10 49 1 0 10 50 1 0 10 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 6 16 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 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 1 30 80 1 0 30 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 M END

Standard InCHIKey	BTXWOKJOAGWCSN-JBYJGCOVSA-N
Standard InCHI	InChI=1S/C31H50O3/c1-26(2)15-17-31(25(33)34-8)18-16-29(6)20(21(31)19-26)9-10-23-28(5)13-12-24(32)27(3,4)22(28)11-14-30(23,29)7/h9,21-24,32H,10-19H2,1-8H3/t21-,22-,23+,24-,28-,29+,30+,31-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2C1)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.38	Volume:	523.047 ? Van der Waals volume.
Dense:	0.899	LogP:	5.404 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.558 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.124 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.322	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.608	Fsp³:	0.903
MCE-18:	104.441 ? 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:	0.899	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.49	Promiscuous compounds:	0.183

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.287	MDCK Permeability:	-4.968
Pgp-inhibitor:	0.28	Pgp-substrate:	0.043
PAMPA:	0.967 ? 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):	0.001
20% Bioavailability (F20%):	0.74	30% Bioavailability (F30%):	0.278
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956	MRP1:	0.823
Plasma Protein Binding (PPB):	96.258%	Volume Distribution (VD):	0.092
Fu:	4.936% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.72
BSEP inhibitor:	0.955

ADMET: Metabolism

CYP1A2-inhibitor:	0.094	CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.993	CYP2C19-substrate:	0.999
CYP2C9-inhibitor:	0.642	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.397	CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.065	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.999 ? 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):

8.481

Half-life (T1/2):

0.409

ADMET: Toxicity

hERG Blockers:	0.124	hERG Blockers (10um):	0.259
Human Hepatotoxicity (H-HT):	0.661	Drug-induced Liver Injury (DILI):	0.269
AMES Toxicity:	0.318	Rat Oral Acute Toxicity:	0.582
Maximum Recommended Daily Dose:	0.688	Skin Sensitization:	0.808
Carcinogencity:	0.869	Eye Corrosion:	0.023
Eye Irritation:	0.311	Respiratory Toxicity:	0.926
Drug-induced Neurotoxicity:	0.087	Ototoxicity:	0.473
Hematotoxicity:	0.398	Drug-induced Nephrotoxicity:	0.682
Genotoxicity:	0.592	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.561	Hek293 Cytotoxicity:	0.414
BCF:	2.654 ? 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:	4.749 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.849 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.58 ? 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
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	DOI[10.1016/j.tetlet.2016.12.029]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	bark	n.a.	DOI[10.1021/np50040a042]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11411539]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15577255]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO4042	Gardenia aubryi	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190447]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20000694]
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22304303]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2832544]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30188125]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38732062]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[9987830]
NPO6586	Dipsacus fullonum	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11487	Senecio madagascariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4387	Mariscus psilostachys	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5370	Chorda filum	Species	Chordaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4042	Gardenia aubryi	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20559	Buxus bodinieri	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1348	Ligustrum japonicus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3636	Gibbaria ilicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4387	Mariscus psilostachys	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8145	Tenebrio molitor	Species	Tenebrionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28189	Metzgeria pubescens	Species	Metzgeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5370	Chorda filum	Species	Chordaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14253	Bothriocline longipes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11003	Euphorbia sancta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20559	Buxus bodinieri	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4042	Gardenia aubryi	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO191	Amaranthus hybr	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6586	Dipsacus fullonum	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1974	Distaplia stylifera	Species	Clavelinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11814	Asphodeline tenuior	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3033	Echinothrix diadema	Species	Diadematidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11985	Glycyrrhiza triphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13164	Iris hoogiana	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11487	Senecio madagascariensis	Species	Asteraceae	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
IC50	11
Ki	1
Activity	9
GI	6
Inhibition	3
EC50	3

Activity Type	# Activity
Individual protein	4
Cell line	19
Organism	3
Others	5
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4440.0	nM	DOI[10.1007/s00044-010-9529-5]
NPT1218	Individual protein	Carbonic anhydrase II	Bos taurus	Ki	>	10000.0	nM	PMID[25147151]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT916	Cell line	SK-MEL	Homo sapiens	IC50	=	103000.0	nM	PMID[10450948]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	80.0	%	PMID[2832544]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	50.0	%	PMID[2832544]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	0.0	%	PMID[2832544]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	100.0	%	PMID[2832544]
NPT81	Cell line	A549	Homo sapiens	IC50	=	55700.0	nM	PMID[15730243]
NPT81	Cell line	A549	Homo sapiens	IC50	=	84000.0	nM	PMID[15730243]
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	=	121000.0	nM	PMID[15730243]
NPT744	Cell line	IMR-32	Homo sapiens	GI	=	55.0	%	DOI[10.1007/s00044-012-0106-y]
NPT81	Cell line	A549	Homo sapiens	GI	=	48.0	%	DOI[10.1007/s00044-012-0106-y]
NPT165	Cell line	HeLa	Homo sapiens	GI	=	18.0	%	DOI[10.1007/s00044-012-0106-y]
NPT2245	Cell line	SiHa	Homo sapiens	GI	=	21.0	%	DOI[10.1007/s00044-012-0106-y]
NPT323	Cell line	SW-620	Homo sapiens	GI	=	8.0	%	DOI[10.1007/s00044-012-0106-y]
NPT407	Cell line	COLO 205	Homo sapiens	GI	=	0.0	%	DOI[10.1007/s00044-012-0106-y]
NPT139	Cell line	HT-29	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT83	Cell line	MCF7	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[26343825]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[26343825]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[26343825]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	90600.0	nM	PMID[15730243]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	>	30000.0	nM	PMID[26177446]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	60.0	%	PMID[23662817]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	30.0	%	PMID[32033878]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	PMID[2832544]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[2832544]
NPT2	Others	Unspecified	n.a.	Activity	=	46.3	%	PMID[2832544]
NPT2	Others	Unspecified	n.a.	Activity	=	29.5	%	PMID[2832544]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	0.0	%	PMID[10794703]

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 NPC246708 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	18050
0.1-0.2	25999
0.2-0.3	4475
0.3-0.4	944
0.4-0.5	258
0.5-0.6	92
0.6-0.7	14
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
0.7759	Intermediate Similarity	NPC235341
0.7705	Intermediate Similarity	NPC136313
0.7679	Intermediate Similarity	NPC290598
0.7679	Intermediate Similarity	NPC30590
0.7627	Intermediate Similarity	NPC470588
0.7581	Intermediate Similarity	NPC488519
0.7288	Intermediate Similarity	NPC101475
0.7286	Intermediate Similarity	NPC167383
0.7143	Intermediate Similarity	NPC214756
0.7097	Intermediate Similarity	NPC40552
0.6935	Remote Similarity	NPC267517
0.6769	Remote Similarity	NPC481361
0.6721	Remote Similarity	NPC34177
0.6719	Remote Similarity	NPC162107
0.6719	Remote Similarity	NPC46912
0.6613	Remote Similarity	NPC253807
0.6613	Remote Similarity	NPC158662
0.6452	Remote Similarity	NPC196753
0.64	Remote Similarity	NPC237503
0.6324	Remote Similarity	NPC49776
0.6324	Remote Similarity	NPC63118
0.6324	Remote Similarity	NPC474436
0.629	Remote Similarity	NPC474989
0.619	Remote Similarity	NPC311078
0.5968	Remote Similarity	NPC27765
0.5968	Remote Similarity	NPC122418
0.5968	Remote Similarity	NPC491014
0.5915	Remote Similarity	NPC294360
0.5857	Remote Similarity	NPC164349
0.5846	Remote Similarity	NPC475862
0.5846	Remote Similarity	NPC480924
0.5797	Remote Similarity	NPC7260
0.5797	Remote Similarity	NPC210037
0.5797	Remote Similarity	NPC120968
0.5797	Remote Similarity	NPC171203
0.5797	Remote Similarity	NPC307426
0.5797	Remote Similarity	NPC98442
0.5797	Remote Similarity	NPC242468
0.5797	Remote Similarity	NPC227467
0.5797	Remote Similarity	NPC273621
0.5758	Remote Similarity	NPC95594
0.573	Remote Similarity	NPC104071
0.5714	Remote Similarity	NPC120098
0.5714	Remote Similarity	NPC29069
0.5694	Remote Similarity	NPC481363
0.5652	Remote Similarity	NPC480946
0.5652	Remote Similarity	NPC213412
0.5652	Remote Similarity	NPC130577
0.5652	Remote Similarity	NPC142415
0.5652	Remote Similarity	NPC102683
0.5652	Remote Similarity	NPC2539
0.5616	Remote Similarity	NPC488520
0.5606	Remote Similarity	NPC195334
0.5595	Remote Similarity	NPC214484
0.5571	Remote Similarity	NPC259788
0.5571	Remote Similarity	NPC255589
0.5571	Remote Similarity	NPC307335
0.5571	Remote Similarity	NPC74855
0.5522	Remote Similarity	NPC230295
0.5522	Remote Similarity	NPC159168
0.5522	Remote Similarity	NPC98386
0.5507	Remote Similarity	NPC477579
0.5469	Remote Similarity	NPC601696
0.5467	Remote Similarity	NPC488522
0.5455	Remote Similarity	NPC191763
0.5443	Remote Similarity	NPC46388
0.5441	Remote Similarity	NPC480950
0.5429	Remote Similarity	NPC191965
0.5429	Remote Similarity	NPC295643
0.5429	Remote Similarity	NPC172361
0.5429	Remote Similarity	NPC610937
0.5385	Remote Similarity	NPC142754
0.5373	Remote Similarity	NPC40394
0.5352	Remote Similarity	NPC112866
0.5342	Remote Similarity	NPC480919
0.5325	Remote Similarity	NPC488524
0.5309	Remote Similarity	NPC306746
0.5294	Remote Similarity	NPC224145
0.5294	Remote Similarity	NPC53744
0.5294	Remote Similarity	NPC238992
0.5294	Remote Similarity	NPC3915
0.5286	Remote Similarity	NPC477872
0.5281	Remote Similarity	NPC249848
0.5281	Remote Similarity	NPC107966
0.5278	Remote Similarity	NPC18872
0.5278	Remote Similarity	NPC290614
0.5263	Remote Similarity	NPC283343
0.5211	Remote Similarity	NPC272075
0.5211	Remote Similarity	NPC187722
0.5211	Remote Similarity	NPC10005
0.5211	Remote Similarity	NPC91525
0.5205	Remote Similarity	NPC228784
0.5205	Remote Similarity	NPC324341
0.5205	Remote Similarity	NPC601810
0.5195	Remote Similarity	NPC473160
0.5161	Remote Similarity	NPC102439
0.5161	Remote Similarity	NPC473459
0.5147	Remote Similarity	NPC291379
0.5147	Remote Similarity	NPC478657
0.5139	Remote Similarity	NPC182797
0.5139	Remote Similarity	NPC51700
0.5139	Remote Similarity	NPC88716
0.5139	Remote Similarity	NPC68160
0.5139	Remote Similarity	NPC52169
0.5139	Remote Similarity	NPC488562
0.5139	Remote Similarity	NPC606443
0.5132	Remote Similarity	NPC175006
0.5128	Remote Similarity	NPC480920
0.5114	Remote Similarity	NPC48499
0.5109	Remote Similarity	NPC223301
0.5109	Remote Similarity	NPC171544
0.5067	Remote Similarity	NPC476879
0.5065	Remote Similarity	NPC471433
0.5065	Remote Similarity	NPC273668
0.5065	Remote Similarity	NPC471432
0.5054	Remote Similarity	NPC30735

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC246708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6958
0.1-0.2	2109
0.2-0.3	77
0.3-0.4	4
0.4-0.5	1
0.5-0.6	1
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
0.5797	Remote Similarity	NPD7645	Phase 2

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