NPASS Compound

Natural Product: NPC89514

Natural Product ID	NPC89514
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Mansonin
IUPAC Name	(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,3R,4S,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms	Mansonin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL444453
PubChem CID	15560101
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 87 92 0 0 0 0 0 0 0 0999 V2000 -7.3989 1.4474 1.8163 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6798 1.3708 0.4856 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5275 0.4851 -0.4029 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6523 -0.7326 -0.7271 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4334 -0.1277 -1.4488 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6633 0.7184 -0.4640 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4161 0.8062 0.7395 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5003 0.1313 -0.1238 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3213 0.8091 -0.2005 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 1.0405 1.1619 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2337 1.3787 0.9236 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4745 0.0522 0.6039 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5599 -0.6738 1.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1829 -0.1969 2.9747 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8745 0.3736 0.0644 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6787 1.2104 1.0064 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7554 0.3979 1.7114 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7460 -0.2024 0.7624 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4286 -1.3593 1.4561 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7264 0.8390 0.2505 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8290 0.5240 -1.2349 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3941 0.1078 -1.6147 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0562 -0.7810 -0.4657 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5972 -0.9112 -0.1559 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8681 -1.7680 -1.1690 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5986 -1.1315 -1.6228 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2783 -0.6661 -0.4611 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2938 0.2748 -1.1224 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8756 -1.7846 0.0706 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5304 -2.0577 -0.7750 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0331 0.7854 0.9389 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2259 0.4936 0.4672 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2031 0.5749 1.5351 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4629 0.3671 1.4881 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5666 0.9293 2.6910 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1992 1.0984 2.3777 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9369 0.6106 -2.5153 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5925 0.0365 -3.7424 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1453 -1.2947 0.4385 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3765 -2.6509 0.5631 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8252 1.0973 -1.6034 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9748 0.5114 2.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7076 1.6571 2.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1372 2.2693 1.7492 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4991 2.3664 0.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4832 0.1850 0.0650 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1646 -1.4289 -1.3888 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8690 -1.0094 -1.8109 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6402 1.7410 -0.8244 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5823 1.8319 -0.5602 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1501 1.9406 1.6484 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7676 0.1579 1.8123 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0803 2.1019 0.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1253 1.7922 1.9043 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9599 -1.6911 2.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6759 0.9069 -0.9091 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2174 1.9984 0.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1233 1.7419 1.7762 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2939 1.1194 2.3632 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3194 -0.3829 2.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5238 -1.3295 1.3988 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1438 -1.4057 2.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1436 -2.3562 1.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2436 1.8232 0.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5517 -0.2731 -1.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1382 1.4329 -1.7644 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8063 1.0193 -1.7031 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4916 -0.4372 -2.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 -1.4964 0.8095 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6747 -2.7922 -0.8226 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5345 -1.8585 -2.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7580 -0.2860 -2.3337 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0133 -1.8965 -2.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7205 -0.2236 -2.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6537 1.0863 -1.5379 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1424 -2.4455 0.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3728 -1.9988 -1.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4602 0.2325 -0.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6082 0.4065 3.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8802 2.1574 2.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0237 0.6705 -4.5460 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9904 -0.9930 -3.8263 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4801 0.0900 -3.8624 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9191 -2.9535 1.5333 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8479 -3.2183 -0.2327 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4358 -2.9366 0.4902 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4923 0.5513 -2.0892 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 13 14 2 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 1 23 30 1 6 20 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 5 37 1 0 37 38 1 0 4 39 1 0 39 40 1 0 3 41 1 0 7 2 1 0 28 9 1 0 36 31 1 0 27 12 1 0 24 15 1 0 23 18 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 6 3 46 1 1 4 47 1 6 5 48 1 6 6 49 1 6 9 50 1 6 10 51 1 0 10 52 1 0 11 53 1 0 11 54 1 0 13 55 1 0 15 56 1 6 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 6 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 24 69 1 1 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 28 74 1 0 28 75 1 0 29 76 1 0 30 77 1 0 32 78 1 0 36 79 1 0 36 80 1 0 38 81 1 0 38 82 1 0 38 83 1 0 40 84 1 0 40 85 1 0 40 86 1 0 41 87 1 0 M END

Standard InCHIKey	BGGIZHKHJBQRTI-VTYGAKHASA-N
Standard InCHI	InChI=1S/C31H46O10/c1-17-24(34)25(37-3)26(38-4)27(40-17)41-19-5-10-29(16-32)21-6-9-28(2)20(18-13-23(33)39-15-18)8-12-31(28,36)22(21)7-11-30(29,35)14-19/h13,16-17,19-22,24-27,34-36H,5-12,14-15H2,1-4H3/t17-,19+,20-,21+,22-,24-,25+,26-,27+,28-,29+,30+,31+/m1/s1
SMILES	C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]1CC[C@]2(C=O)[C@H]3CC[C@]4(C)[C@H](CC[C@@]4([C@@H]3CC[C@@]2(C1)O)O)C1=CC(=O)OC1)OC)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.31	Volume:	573.386 ? Van der Waals volume.
Dense:	1.009	LogP:	1.101 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.706 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.526 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	33.0
TPSA:	140.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.244	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.409	Fsp³:	0.871
MCE-18:	114.517 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.81	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.168	Promiscuous compounds:	0.53

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.545	MDCK Permeability:	-5.166
Pgp-inhibitor:	0.011	Pgp-substrate:	0.969
PAMPA:	0.975 ? 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):	0.149
20% Bioavailability (F20%):	0.427	30% Bioavailability (F30%):	0.531
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125	MRP1:	0.531
Plasma Protein Binding (PPB):	66.31%	Volume Distribution (VD):	-0.295
Fu:	29.161% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.056
BSEP inhibitor:	0.486

ADMET: Metabolism

CYP1A2-inhibitor:	0.877	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.74	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.01
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.036 ? 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):

4.083

Half-life (T1/2):

3.565

ADMET: Toxicity

hERG Blockers:	0.185	hERG Blockers (10um):	0.624
Human Hepatotoxicity (H-HT):	0.821	Drug-induced Liver Injury (DILI):	0.676
AMES Toxicity:	0.882	Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.943	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.984
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.719
Hematotoxicity:	0.53	Drug-induced Nephrotoxicity:	0.982
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.859
A549 Cytotoxicity:	0.672	Hek293 Cytotoxicity:	0.988
BCF:	0.573 ? 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:	3.339 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.834 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.153 ? 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
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np020518b]
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762814]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679307]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	Australian rainforest	n.a.	PMID[18039010]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20218657]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[23434030]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4093781]
NPO17202	Lasallia asiae-orientalis	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25866	Kaunia lasiophthalma	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9565	Linum maritimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7535	Mansonia altissima	Species	Culicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11354	Streptomyces galbus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13058	Psychotria brachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2124	Bulgaria inquinans	Species	Bulgariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2124	Bulgaria inquinans	Species	Bulgariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10273	Dictyota flabellata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13058	Psychotria brachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11354	Streptomyces galbus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24924	Saara hardwickii	Species	Agamidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17202	Lasallia asiae-orientalis	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3546	Shorea balangeran	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25866	Kaunia lasiophthalma	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8878	Polygala arenaria	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9794	Dysoxylum fraseranum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11158	Diplopterygium rufopilosum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7535	Mansonia altissima	Species	Culicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6878	Vesperus xatarti	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11510	Astragalus flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12123	Geodia gigas	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4348	Watasenia scintillans	Species	Enoploteuthidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9565	Linum maritimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6423	Vitex cauliflora	Species	Lamiaceae	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
ED50	1

Activity Type	# Activity
Cell line	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
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.042	ug ml-1	PMID[4093781]

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 NPC89514 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	13908
0.1-0.2	31922
0.2-0.3	3746
0.3-0.4	89
0.4-0.5	101
0.5-0.6	53
0.6-0.7	22
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC6108
0.8289	Intermediate Similarity	NPC10823
0.7949	Intermediate Similarity	NPC180079
0.725	Intermediate Similarity	NPC17896
0.725	Intermediate Similarity	NPC469755
0.725	Intermediate Similarity	NPC284406
0.725	Intermediate Similarity	NPC197707
0.725	Intermediate Similarity	NPC251866
0.7195	Intermediate Similarity	NPC93883
0.7125	Intermediate Similarity	NPC219085
0.6966	Remote Similarity	NPC247190
0.6848	Remote Similarity	NPC329636
0.6829	Remote Similarity	NPC34390
0.6706	Remote Similarity	NPC469753
0.6667	Remote Similarity	NPC469749
0.6517	Remote Similarity	NPC32793
0.6517	Remote Similarity	NPC116075
0.6517	Remote Similarity	NPC608063
0.6413	Remote Similarity	NPC146857
0.6316	Remote Similarity	NPC72772
0.6265	Remote Similarity	NPC474418
0.619	Remote Similarity	NPC99728
0.619	Remote Similarity	NPC87250
0.619	Remote Similarity	NPC244402
0.619	Remote Similarity	NPC50305
0.6122	Remote Similarity	NPC329675
0.6092	Remote Similarity	NPC250556
0.6092	Remote Similarity	NPC484212
0.6071	Remote Similarity	NPC158344
0.6047	Remote Similarity	NPC157376
0.6047	Remote Similarity	NPC142066
0.6047	Remote Similarity	NPC603972
0.596	Remote Similarity	NPC194716
0.593	Remote Similarity	NPC84987
0.5843	Remote Similarity	NPC9499
0.5843	Remote Similarity	NPC471360
0.5843	Remote Similarity	NPC469751
0.5843	Remote Similarity	NPC471361
0.5843	Remote Similarity	NPC86159
0.5843	Remote Similarity	NPC469752
0.5843	Remote Similarity	NPC469754
0.5843	Remote Similarity	NPC70542
0.5824	Remote Similarity	NPC488935
0.5824	Remote Similarity	NPC488936
0.5795	Remote Similarity	NPC199428
0.5795	Remote Similarity	NPC84949
0.5795	Remote Similarity	NPC109448
0.5795	Remote Similarity	NPC480562
0.5795	Remote Similarity	NPC74945
0.5795	Remote Similarity	NPC310341
0.5795	Remote Similarity	NPC31354
0.5795	Remote Similarity	NPC69576
0.5745	Remote Similarity	NPC475629
0.5667	Remote Similarity	NPC471359
0.5667	Remote Similarity	NPC483822
0.5667	Remote Similarity	NPC305574
0.5568	Remote Similarity	NPC484211
0.5521	Remote Similarity	NPC59288
0.5513	Remote Similarity	NPC97487
0.551	Remote Similarity	NPC486138
0.551	Remote Similarity	NPC276838
0.5506	Remote Similarity	NPC486126
0.5506	Remote Similarity	NPC469750
0.5474	Remote Similarity	NPC475556
0.5474	Remote Similarity	NPC311706
0.5393	Remote Similarity	NPC309034
0.5393	Remote Similarity	NPC486129
0.5375	Remote Similarity	NPC10232
0.5361	Remote Similarity	NPC55532
0.5326	Remote Similarity	NPC484202
0.5281	Remote Similarity	NPC99620
0.5281	Remote Similarity	NPC471633
0.5275	Remote Similarity	NPC480914
0.5253	Remote Similarity	NPC486146
0.5217	Remote Similarity	NPC77319
0.5217	Remote Similarity	NPC88668
0.5217	Remote Similarity	NPC471351
0.5217	Remote Similarity	NPC471355
0.5152	Remote Similarity	NPC232785
0.5152	Remote Similarity	NPC486139
0.5143	Remote Similarity	NPC486150
0.5109	Remote Similarity	NPC76572
0.5109	Remote Similarity	NPC193382
0.5062	Remote Similarity	NPC187302
0.5053	Remote Similarity	NPC72260

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC89514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5794
0.1-0.2	3229
0.2-0.3	113
0.3-0.4	2
0.4-0.5	7
0.5-0.6	3
0.6-0.7	1
0.7-0.8	1
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
0.725	Intermediate Similarity	NPD7319	Approved
0.6092	Remote Similarity	NPD7507	Pre-clinical
0.5495	Remote Similarity	NPD7516	Pre-clinical
0.5053	Remote Similarity	NPD8294	Phase 4
0.5051	Remote Similarity	NPD8377	Phase 4

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