NPASS Compound

Natural Product: NPC84949

Natural Product ID	NPC84949
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-Hydroxy-3-[(2R,4S,5R,6R)-5-Hydroxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-10,13-Dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-Tetradecahydrocyclopenta[A]Phenanthren-17-Yl]-2H-Furan-5-One
IUPAC Name	3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1993326
PubChem CID	12310598
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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 83 88 0 0 0 0 0 0 0 0999 V2000 -7.3667 2.9069 0.6014 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8156 1.5802 0.0630 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3840 0.5032 0.9751 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8151 -0.8147 0.4959 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3091 -0.7862 0.4505 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7837 0.4903 -0.1711 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4553 1.6158 0.2378 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4477 0.6203 0.2694 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5525 0.5957 -0.7780 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7340 1.8419 -0.9205 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2996 1.4099 -1.1914 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2906 0.7562 0.0654 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2978 1.7600 1.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5611 -0.4454 0.3567 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2133 -1.7403 0.3650 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4650 -1.6889 1.1760 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3132 -0.5344 0.7340 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6867 0.2991 -0.3328 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5827 1.4591 -0.6587 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8173 1.5303 0.1753 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5775 0.2365 0.2652 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4197 0.2915 1.5224 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4707 0.0122 -0.9363 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3185 -1.4861 -1.2487 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8077 -1.6138 -0.9817 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6924 -0.9645 0.3477 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1981 -1.8593 1.2954 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8941 0.3420 -0.6790 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8779 -0.5330 -0.7069 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1391 0.1187 -0.4116 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2630 -0.4567 -0.3644 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8281 1.4450 -0.2067 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4610 1.6635 -0.3658 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -0.6218 -0.6407 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3445 -1.0759 -0.7690 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1165 -2.2360 -0.7552 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7572 0.4929 0.8250 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7271 3.7173 0.2095 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4283 2.9883 0.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2717 2.9237 1.7229 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1573 1.4930 -0.9710 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0570 0.7262 2.0010 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1485 -1.6038 1.1887 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9939 -1.6428 -0.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8855 -0.9857 1.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7326 0.4026 -1.2779 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1198 0.4758 -1.7476 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0382 2.4596 -1.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7459 2.4897 -0.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2752 2.2706 -1.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2981 0.6622 -2.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0561 1.6036 1.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3719 2.7833 0.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6960 1.7164 1.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.3062 1.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4539 -2.5165 0.8078 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4554 -2.0903 -0.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0300 -2.6127 1.0045 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2284 -1.6656 2.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4328 0.1320 1.6390 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5158 -0.3696 -1.2282 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8478 1.5303 -1.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9941 2.3986 -0.4388 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5534 1.9267 1.1804 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4999 2.2761 -0.2890 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9907 -0.4137 2.2816 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4586 -0.0312 1.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3554 1.2860 2.0108 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1352 0.6210 -1.7846 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5694 -1.7158 -2.2866 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8322 -2.0802 -0.4902 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3284 -1.0796 -1.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5154 -2.6876 -0.9807 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0629 -2.7785 0.9663 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8101 -1.6153 -0.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9906 2.1617 0.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3220 2.2855 -1.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3495 -1.4275 -0.1985 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3456 -1.0404 -1.6053 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5380 -3.1201 -0.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6011 -2.3312 -1.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9417 -2.0866 -0.0171 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2488 0.6266 1.6732 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 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 1 23 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 14 34 1 0 4 35 1 0 35 36 1 0 3 37 1 0 7 2 1 0 34 9 1 0 18 12 1 0 26 21 1 0 33 28 1 0 26 17 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 6 3 42 1 1 4 43 1 1 5 44 1 0 5 45 1 0 6 46 1 6 9 47 1 6 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 13 52 1 0 13 53 1 0 13 54 1 0 14 55 1 1 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 1 18 61 1 6 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 22 66 1 0 22 67 1 0 22 68 1 0 23 69 1 6 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 27 74 1 0 29 75 1 0 33 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 36 80 1 0 36 81 1 0 36 82 1 0 37 83 1 0 M END

Standard InCHIKey	YBZZSZQZDODUAA-QBHHOFBOSA-N
Standard InCHI	InChI=1S/C30H46O7/c1-17-27(32)24(34-4)15-26(36-17)37-20-7-10-28(2)19(14-20)5-6-23-22(28)8-11-29(3)21(9-12-30(23,29)33)18-13-25(31)35-16-18/h13,17,19-24,26-27,32-33H,5-12,14-16H2,1-4H3/t17-,19-,20+,21-,22+,23-,24+,26+,27-,28+,29-,30+/m1/s1
SMILES	C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.32	Volume:	532.356 ? Van der Waals volume.
Dense:	0.974	LogP:	3.159 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.242 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.595 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	32.0
TPSA:	94.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.427	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.04	Fsp³:	0.9
MCE-18:	106.667 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.85	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? 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:	0.185	Promiscuous compounds:	0.335

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.383	MDCK Permeability:	-5.111
Pgp-inhibitor:	0.482	Pgp-substrate:	0.701
PAMPA:	0.929 ? 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):	0.007
20% Bioavailability (F20%):	0.174	30% Bioavailability (F30%):	0.113
50% Bioavailability (F50%):	0.757

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095	MRP1:	0.768
Plasma Protein Binding (PPB):	91.005%	Volume Distribution (VD):	0.109
Fu:	7.15% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	0.861	BCRP inhibitor:	0.252
BSEP inhibitor:	0.966

ADMET: Metabolism

CYP1A2-inhibitor:	0.988	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.989
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.046
HLM stability:	0.474 ? 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):

9.907

Half-life (T1/2):

2.472

ADMET: Toxicity

hERG Blockers:	0.226	hERG Blockers (10um):	0.774
Human Hepatotoxicity (H-HT):	0.56	Drug-induced Liver Injury (DILI):	0.98
AMES Toxicity:	0.95	Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.953	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.995
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.685
Hematotoxicity:	0.788	Drug-induced Nephrotoxicity:	0.98
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.82
A549 Cytotoxicity:	0.741	Hek293 Cytotoxicity:	0.979
BCF:	0.694 ? 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:	3.435 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.971 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.332 ? 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
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)89267-5]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)98060-9]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1042/bst0160071]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11559179]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12882150]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15666542]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18001808]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23479199]
NPO3447	Beaumontia murtonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28598616]
NPO40841	Eugenia operculata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28598616]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36500609]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	trunk bark	n.a.	PMID[556731]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tuber	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3447	Beaumontia murtonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17694	Nicotiana tabacum	Species	Solanaceae	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
GI50	60

Activity Type	# Activity
Cell line	60

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
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	11.35	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	14.86	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	49.77	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	15.78	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	24.55	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	11.04	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	16.79	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	15.1	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	15.0	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	13.4	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	11.35	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	12.5	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	11.12	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	13.68	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	18.45	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	23.99	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	69.5	nM	PubChem BioAssay data set

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 NPC84949 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	12558
0.1-0.2	32498
0.2-0.3	4452
0.3-0.4	108
0.4-0.5	95
0.5-0.6	85
0.6-0.7	34
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC480562
1.0	High Similarity	NPC74945
1.0	High Similarity	NPC31354
1.0	High Similarity	NPC69576
0.8442	Intermediate Similarity	NPC483822
0.8289	Intermediate Similarity	NPC99080
0.7975	Intermediate Similarity	NPC484202
0.7792	Intermediate Similarity	NPC471633
0.7722	Intermediate Similarity	NPC199428
0.7722	Intermediate Similarity	NPC109448
0.7722	Intermediate Similarity	NPC310341
0.7683	Intermediate Similarity	NPC103534
0.7683	Intermediate Similarity	NPC44899
0.7683	Intermediate Similarity	NPC304260
0.7683	Intermediate Similarity	NPC29639
0.7595	Intermediate Similarity	NPC34390
0.7531	Intermediate Similarity	NPC93883
0.7407	Intermediate Similarity	NPC180079
0.7375	Intermediate Similarity	NPC477580
0.7342	Intermediate Similarity	NPC99620
0.7284	Intermediate Similarity	NPC152615
0.7241	Intermediate Similarity	NPC55532
0.7143	Intermediate Similarity	NPC72260
0.6951	Remote Similarity	NPC5311
0.6667	Remote Similarity	NPC486143
0.6667	Remote Similarity	NPC486142
0.6667	Remote Similarity	NPC486149
0.6632	Remote Similarity	NPC475419
0.6588	Remote Similarity	NPC250556
0.6588	Remote Similarity	NPC484212
0.6522	Remote Similarity	NPC486146
0.6512	Remote Similarity	NPC305574
0.6458	Remote Similarity	NPC120390
0.6404	Remote Similarity	NPC30483
0.6404	Remote Similarity	NPC470897
0.6364	Remote Similarity	NPC474423
0.6353	Remote Similarity	NPC479356
0.6353	Remote Similarity	NPC469750
0.6353	Remote Similarity	NPC479355
0.6333	Remote Similarity	NPC236973
0.6333	Remote Similarity	NPC292467
0.6289	Remote Similarity	NPC74259
0.6279	Remote Similarity	NPC76572
0.6279	Remote Similarity	NPC193382
0.625	Remote Similarity	NPC486144
0.625	Remote Similarity	NPC486145
0.625	Remote Similarity	NPC329636
0.625	Remote Similarity	NPC486147
0.625	Remote Similarity	NPC486148
0.6224	Remote Similarity	NPC474908
0.617	Remote Similarity	NPC329986
0.617	Remote Similarity	NPC140092
0.6118	Remote Similarity	NPC473852
0.6082	Remote Similarity	NPC475590
0.6061	Remote Similarity	NPC486134
0.6061	Remote Similarity	NPC486141
0.6023	Remote Similarity	NPC290693
0.5977	Remote Similarity	NPC77299
0.5977	Remote Similarity	NPC480906
0.5974	Remote Similarity	NPC268829
0.5974	Remote Similarity	NPC295110
0.5934	Remote Similarity	NPC488935
0.5934	Remote Similarity	NPC173555
0.5934	Remote Similarity	NPC5883
0.5934	Remote Similarity	NPC488936
0.5914	Remote Similarity	NPC603096
0.5909	Remote Similarity	NPC480914
0.5889	Remote Similarity	NPC193893
0.5862	Remote Similarity	NPC196429
0.5814	Remote Similarity	NPC474418
0.5795	Remote Similarity	NPC6108
0.5795	Remote Similarity	NPC89514
0.5795	Remote Similarity	NPC480915
0.5789	Remote Similarity	NPC486135
0.5789	Remote Similarity	NPC486137
0.5745	Remote Similarity	NPC240070
0.5729	Remote Similarity	NPC232785
0.5729	Remote Similarity	NPC486139
0.5682	Remote Similarity	NPC486129
0.5652	Remote Similarity	NPC480907
0.5625	Remote Similarity	NPC125077
0.5618	Remote Similarity	NPC486126
0.5612	Remote Similarity	NPC486138
0.5612	Remote Similarity	NPC276838
0.5604	Remote Similarity	NPC179412
0.5604	Remote Similarity	NPC471356
0.5579	Remote Similarity	NPC480910
0.5579	Remote Similarity	NPC480909
0.5568	Remote Similarity	NPC479351
0.5568	Remote Similarity	NPC99728
0.5568	Remote Similarity	NPC87250
0.5568	Remote Similarity	NPC244402
0.5568	Remote Similarity	NPC479352
0.5568	Remote Similarity	NPC50305
0.5543	Remote Similarity	NPC268326
0.5543	Remote Similarity	NPC153085
0.5521	Remote Similarity	NPC231518
0.5521	Remote Similarity	NPC488944
0.5474	Remote Similarity	NPC32177
0.5474	Remote Similarity	NPC469756
0.5474	Remote Similarity	NPC275901
0.5472	Remote Similarity	NPC286809
0.5464	Remote Similarity	NPC208193
0.5446	Remote Similarity	NPC486136
0.5444	Remote Similarity	NPC157376
0.5444	Remote Similarity	NPC17896
0.5444	Remote Similarity	NPC469755
0.5444	Remote Similarity	NPC284406
0.5444	Remote Similarity	NPC197707
0.5444	Remote Similarity	NPC251866
0.5444	Remote Similarity	NPC142066
0.5444	Remote Similarity	NPC603972
0.5435	Remote Similarity	NPC471353
0.5417	Remote Similarity	NPC188234
0.5385	Remote Similarity	NPC10823
0.5354	Remote Similarity	NPC146857
0.5333	Remote Similarity	NPC481208
0.5326	Remote Similarity	NPC88668
0.5288	Remote Similarity	NPC117445
0.5288	Remote Similarity	NPC308262
0.5244	Remote Similarity	NPC222875
0.5244	Remote Similarity	NPC25177
0.5238	Remote Similarity	NPC486150
0.5233	Remote Similarity	NPC246399
0.5233	Remote Similarity	NPC34977
0.5233	Remote Similarity	NPC221196
0.5227	Remote Similarity	NPC39485
0.5196	Remote Similarity	NPC479360
0.5196	Remote Similarity	NPC479359
0.5196	Remote Similarity	NPC488943
0.5196	Remote Similarity	NPC488938
0.5196	Remote Similarity	NPC488937
0.5196	Remote Similarity	NPC488942
0.5185	Remote Similarity	NPC187302
0.5165	Remote Similarity	NPC84987
0.5155	Remote Similarity	NPC115349
0.5122	Remote Similarity	NPC196931
0.5122	Remote Similarity	NPC480913
0.5111	Remote Similarity	NPC158344
0.5102	Remote Similarity	NPC486151
0.5098	Remote Similarity	NPC475219
0.5051	Remote Similarity	NPC475629

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC84949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5628
0.1-0.2	3385
0.2-0.3	121
0.3-0.4	2
0.4-0.5	3
0.5-0.6	4
0.6-0.7	5
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8072	Intermediate Similarity	NPD8377	Phase 4
0.7143	Intermediate Similarity	NPD8294	Phase 4
0.6778	Remote Similarity	NPD8378	Pre-clinical
0.6778	Remote Similarity	NPD8379	Approved
0.6588	Remote Similarity	NPD7507	Pre-clinical
0.6512	Remote Similarity	NPD7516	Pre-clinical
0.6207	Remote Similarity	NPD8335	Phase 4
0.5934	Remote Similarity	NPD8296	Phase 4
0.5778	Remote Similarity	NPD8380	Approved
0.5521	Remote Similarity	NPD8033	Approved
0.5444	Remote Similarity	NPD7319	Approved

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