NPASS Compound

Natural Product: NPC177340

Natural Product ID	NPC177340
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KPSZHLRCVCNGHG-NPIRVHPYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL373768
PubChem CID	16109789
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids 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 2D 93 98 0 0 0 0 0 0 0 0999 V2000 -7.5384 -2.9306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0590 -3.1781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5336 -4.5831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1050 -2.0206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6255 -2.2680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3199 -3.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0275 -2.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5021 -3.6501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3463 -0.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6387 -0.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1641 0.6369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6436 0.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7316 -0.1483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1690 2.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5599 0.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7734 1.7567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1437 1.1466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4812 -0.3150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3572 2.0282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2004 3.5200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4140 4.4017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7843 3.7916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9411 2.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7276 1.4181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1895 1.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5524 2.9405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4734 3.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0081 3.7479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8363 5.4380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7573 6.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1202 7.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5621 8.3489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6411 7.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2782 5.8514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8192 2.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5241 0.5932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4057 1.8067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1454 3.2840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8975 1.6499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7792 2.8635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2710 2.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8811 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9994 0.1228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5076 0.2796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 1.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 -1.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0179 -2.6832 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7859 -4.4101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4732 -1.4321 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1261 -3.6820 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2739 -4.1641 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4919 -4.2574 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4697 -2.3367 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0233 -5.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9029 -3.1247 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8326 -4.3429 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0692 -1.2193 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3389 3.7796 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5740 1.7639 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7641 2.8147 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7169 2.3668 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2870 -0.4370 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9147 4.2926 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2572 5.8935 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9978 4.6733 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3114 1.6897 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8843 -0.0736 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3714 2.4088 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6846 6.0665 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0412 8.9774 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9249 9.8043 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0830 7.7203 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3572 4.8094 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2598 3.1372 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3322 3.5048 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8578 2.6401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6899 2.0982 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0066 4.1492 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4201 3.6708 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2906 0.8232 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7720 -1.1629 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9458 -1.1112 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5054 2.0074 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5228 0.0196 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5304 2.2324 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5054 -2.0074 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5228 -0.0196 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3870 -2.1184 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 10 16 1 6 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 10 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 26 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 37 48 1 0 48 49 1 0 48 50 1 0 48 51 1 0 11 5 1 0 25 20 1 0 35 30 1 0 47 42 1 0 9 49 1 1 38 9 1 0 1 52 1 0 1 53 1 0 1 54 1 0 5 55 1 1 6 56 1 0 6 57 1 0 7 58 1 1 8 59 1 0 8 60 1 0 8 61 1 0 11 62 1 1 15 63 1 0 15 64 1 0 15 65 1 0 16 66 1 0 16 67 1 0 21 68 1 0 22 69 1 0 23 70 1 0 24 71 1 0 25 72 1 0 26 73 1 6 31 74 1 0 32 75 1 0 33 76 1 0 34 77 1 0 35 78 1 0 36 79 1 0 36 80 1 0 37 81 1 6 38 82 1 1 43 83 1 0 44 84 1 0 45 85 1 0 46 86 1 0 47 87 1 0 50 88 1 0 50 89 1 0 50 90 1 0 51 91 1 0 51 92 1 0 51 93 1 0 M END

Standard InCHIKey	KPSZHLRCVCNGHG-NPIRVHPYSA-N
Standard InCHI	InChI=1S/C40H42O11/c1-24-21-31(47-25(2)41)34(48-26(3)42)39(23-46-35(43)27-15-9-6-10-16-27)32(49-36(44)28-17-11-7-12-18-28)22-30-33(40(24,39)51-38(30,4)5)50-37(45)29-19-13-8-14-20-29/h6-20,24,30-34H,21-23H2,1-5H3/t24-,30-,31+,32+,33-,34+,39-,40-/m1/s1
SMILES	CC(=O)O[C@H]1C[C@@H](C)[C@@]23[C@]([C@H]1OC(=O)C)(COC(=O)c1ccccc1)[C@@H](OC(=O)c1ccccc1)C[C@H]([C@H]3OC(=O)c1ccccc1)C(O2)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	698.27	Volume:	708.839 ? Van der Waals volume.
Dense:	0.985	LogP:	4.445 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.732 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.735 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	37.0
TPSA:	140.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.199	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.789	Fsp³:	0.425
MCE-18:	179.825 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.922	Fluc inhibitor:	0.154 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.437 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.231	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.311	MDCK Permeability:	-4.774
Pgp-inhibitor:	0.996	Pgp-substrate:	0.055
PAMPA:	0.028 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.009
50% Bioavailability (F50%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988	MRP1:	1.0
Plasma Protein Binding (PPB):	95.785%	Volume Distribution (VD):	-0.504
Fu:	4.575% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.02
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.997
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.052	CYP3A4-substrate:	0.537
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

1.446

Half-life (T1/2):

1.072

ADMET: Toxicity

hERG Blockers:	0.151	hERG Blockers (10um):	0.672
Human Hepatotoxicity (H-HT):	0.039	Drug-induced Liver Injury (DILI):	0.971
AMES Toxicity:	0.247	Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.265	Skin Sensitization:	0.988
Carcinogencity:	0.632	Eye Corrosion:	0.0
Eye Irritation:	0.056	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.755	Ototoxicity:	0.22
Hematotoxicity:	0.021	Drug-induced Nephrotoxicity:	0.51
Genotoxicity:	0.113	RPMI-8226 Immunitoxicity:	0.051
A549 Cytotoxicity:	0.533	Hek293 Cytotoxicity:	0.68
BCF:	0.868 ? 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:	4.297 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.467 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.366 ? 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
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[15467233]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[18471021]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[18471021]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	Stems	n.a.	n.a.	PMID[19534471]
NPO10464	Epipedobates anthonyi	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337496]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8778243]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358636]
NPO22212	Rhizophora mangle	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22272	Raphanus raphanistrum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21776	Sesbania grandiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6425	Betula davurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3277	Salix alba	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5933	Drimia fugax	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5933	Drimia fugax	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22670	Phebalium bilobum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14938	Cybister lateralimarginalis	Species	Dytiscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22212	Rhizophora mangle	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6425	Betula davurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10464	Epipedobates anthonyi	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19561	Garcinia conrauana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21776	Sesbania grandiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22915	Stereocaulon azoreum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22272	Raphanus raphanistrum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17102	Ocypus olens	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3277	Salix alba	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22734	Neopringlea integrifolia	Species	Salicaceae	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
MIC	1

Activity Type	# Activity
Organism	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
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	96000.0	nM	PMID[17315960]

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 NPC177340 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	13613
0.1-0.2	34157
0.2-0.3	1481
0.3-0.4	444
0.4-0.5	90
0.5-0.6	34
0.6-0.7	17
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9344	High Similarity	NPC67777
0.9344	High Similarity	NPC43241
0.873	High Similarity	NPC139067
0.8281	Intermediate Similarity	NPC479047
0.8281	Intermediate Similarity	NPC191082
0.8281	Intermediate Similarity	NPC291638
0.7778	Intermediate Similarity	NPC200592
0.7778	Intermediate Similarity	NPC610542
0.7727	Intermediate Similarity	NPC4341
0.7647	Intermediate Similarity	NPC479044
0.7463	Intermediate Similarity	NPC246480
0.7231	Intermediate Similarity	NPC195647
0.7231	Intermediate Similarity	NPC270498
0.7183	Intermediate Similarity	NPC184747
0.7101	Intermediate Similarity	NPC147217
0.7042	Intermediate Similarity	NPC266265
0.7	Intermediate Similarity	NPC473673
0.6957	Remote Similarity	NPC48017
0.6883	Remote Similarity	NPC75600
0.6883	Remote Similarity	NPC483884
0.6716	Remote Similarity	NPC473081
0.6667	Remote Similarity	NPC92293
0.6486	Remote Similarity	NPC95265
0.6267	Remote Similarity	NPC97667
0.625	Remote Similarity	NPC147880
0.6184	Remote Similarity	NPC607428
0.6154	Remote Similarity	NPC14499
0.6111	Remote Similarity	NPC17877
0.6087	Remote Similarity	NPC283375
0.6087	Remote Similarity	NPC183122
0.6081	Remote Similarity	NPC471100
0.6081	Remote Similarity	NPC605884
0.6053	Remote Similarity	NPC70716
0.6	Remote Similarity	NPC472574
0.5974	Remote Similarity	NPC473112
0.5946	Remote Similarity	NPC148062
0.589	Remote Similarity	NPC473060
0.5789	Remote Similarity	NPC41481
0.5769	Remote Similarity	NPC473613
0.575	Remote Similarity	NPC88593
0.5733	Remote Similarity	NPC27377
0.5696	Remote Similarity	NPC479042
0.5694	Remote Similarity	NPC481047
0.5694	Remote Similarity	NPC481045
0.5676	Remote Similarity	NPC483902
0.5676	Remote Similarity	NPC472577
0.5658	Remote Similarity	NPC254558
0.5658	Remote Similarity	NPC471107
0.5634	Remote Similarity	NPC474608
0.5581	Remote Similarity	NPC294512
0.557	Remote Similarity	NPC473085
0.5542	Remote Similarity	NPC610134
0.5526	Remote Similarity	NPC137718
0.5467	Remote Similarity	NPC51314
0.5467	Remote Similarity	NPC163087
0.5455	Remote Similarity	NPC171207
0.5443	Remote Similarity	NPC96903
0.5417	Remote Similarity	NPC481066
0.5402	Remote Similarity	NPC176413
0.5402	Remote Similarity	NPC483885
0.5357	Remote Similarity	NPC473089
0.5341	Remote Similarity	NPC483868
0.5316	Remote Similarity	NPC479043
0.5195	Remote Similarity	NPC483883
0.5195	Remote Similarity	NPC151585
0.5128	Remote Similarity	NPC270590
0.5125	Remote Similarity	NPC609924
0.5065	Remote Similarity	NPC70973

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC177340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3179
0.1-0.2	5790
0.2-0.3	179
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