NPASS Compound

Natural Product: NPC13710

Natural Product ID	NPC13710
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UUDZDKPKXAEKLA-YHLOYHKPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL447760
PubChem CID	10031398
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

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 80 83 0 0 0 0 0 0 0 0999 V2000 2.6476 -1.5701 -0.6644 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8682 -0.1472 -0.3499 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8642 0.7134 -0.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4891 0.3142 -0.5864 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5207 1.1658 -0.5555 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9368 0.7437 -0.8353 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2821 1.2581 -2.1920 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7533 1.3076 0.2867 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0847 0.8886 1.5833 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0043 -0.1181 2.2381 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7911 -0.6206 1.0101 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8982 -1.4271 1.5403 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0152 -1.7466 0.6628 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6666 -0.9513 -0.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3946 0.4932 -0.3939 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9446 0.6861 -0.8021 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1191 0.7221 0.4338 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8115 1.4539 1.4249 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0968 2.7922 1.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7331 3.4641 0.3933 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8280 3.4343 2.4898 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7676 -1.5338 -0.9446 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0964 -2.7284 -0.8467 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4836 -0.7420 -1.8300 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5535 -1.3055 -2.5873 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8441 -1.3591 0.1210 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7843 -2.6238 0.2252 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0688 -0.6598 -0.7783 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2182 0.3281 -0.0682 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4686 1.5301 0.2065 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2833 -0.5418 -0.0945 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5943 -0.0762 0.1798 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2215 -0.7756 1.3443 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2143 -1.8275 0.9666 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1827 -1.3984 -0.0997 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7121 -0.1040 -0.7343 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4068 0.0102 -2.0752 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8922 1.1148 -2.7523 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3410 -0.2657 -0.9815 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4501 -1.2770 0.4420 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4979 -2.9652 0.5883 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7926 0.1272 2.2583 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6172 -2.0187 -0.9651 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3419 -2.1305 0.2558 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9579 -1.7389 -1.5143 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1031 1.7418 -0.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3321 -0.7289 -0.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2690 2.1866 -0.3164 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 0.6264 -2.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6766 2.2937 -2.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3481 1.2491 -2.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6843 2.3903 0.2337 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1389 0.3191 1.4059 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8810 1.7571 2.2428 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4714 -0.9466 2.7263 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6939 0.4222 2.8876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2460 -0.9838 2.5213 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4469 -2.4137 1.8615 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4023 -2.7598 0.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6405 1.0100 0.5532 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0935 0.8715 -1.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8537 1.5538 -1.4482 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6895 -0.2780 -1.3377 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8502 3.6625 2.1145 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9391 2.7576 3.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3195 4.3422 2.8743 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2328 -2.1371 -3.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0111 -0.4747 -3.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3408 -1.6191 -1.8592 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6022 1.0154 0.3990 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3963 -1.2941 1.9070 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7647 -2.1152 1.8960 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1893 -2.1903 -0.8834 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9105 0.7695 -0.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3074 -0.9307 -2.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4825 0.1919 -1.9329 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4011 1.9329 -2.4541 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7873 -0.3546 0.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9929 -2.7755 -0.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3686 1.0138 2.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 6 6 8 1 0 8 9 1 0 9 10 1 0 11 10 1 1 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 18 19 1 0 19 20 2 0 19 21 1 0 14 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 11 26 1 0 26 27 2 0 26 28 1 0 2 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 28 6 1 0 39 32 1 0 17 8 1 0 17 11 1 0 1 43 1 0 1 44 1 0 1 45 1 0 3 46 1 0 4 47 1 0 5 48 1 0 7 49 1 0 7 50 1 0 7 51 1 0 8 52 1 6 9 53 1 0 9 54 1 0 10 55 1 0 10 56 1 0 12 57 1 0 12 58 1 0 13 59 1 0 15 60 1 0 15 61 1 0 16 62 1 0 16 63 1 0 21 64 1 0 21 65 1 0 21 66 1 0 25 67 1 0 25 68 1 0 25 69 1 0 32 70 1 1 33 71 1 1 34 72 1 1 35 73 1 6 36 74 1 1 37 75 1 0 37 76 1 0 38 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 M END

Standard InCHIKey	UUDZDKPKXAEKLA-YHLOYHKPSA-N
Standard InCHI	InChI=1S/C29H38O13/c1-15(23(35)40-25-22(34)21(33)20(32)18(14-30)39-25)6-5-10-27(3)19-9-12-28(26(37)42-27)11-7-17(24(36)38-4)8-13-29(19,28)41-16(2)31/h5-7,10,18-22,25,30,32-34H,8-9,11-14H2,1-4H3/b10-5+,15-6+/t18-,19+,20-,21+,22-,25+,27-,28-,29+/m1/s1
SMILES	C/C(=CC=C[C@]1(C)[C@@H]2CC[C@]3(CC=C(CC[C@]23OC(=O)C)C(=O)OC)C(=O)O1)/C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.23	Volume:	571.732 ? Van der Waals volume.
Dense:	1.039	LogP:	-0.072 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.796 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.06 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	27.0
TPSA:	195.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.135	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.967	Fsp³:	0.655
MCE-18:	85.25 ? 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:	0.712	Fluc inhibitor:	0.05 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.05 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.281 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.173	Promiscuous compounds:	0.124

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.544	MDCK Permeability:	-5.024
Pgp-inhibitor:	0.007	Pgp-substrate:	0.331
PAMPA:	0.995 ? 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):	0.497
20% Bioavailability (F20%):	0.641	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.884
Plasma Protein Binding (PPB):	67.126%	Volume Distribution (VD):	-0.393
Fu:	33.065% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.084
BSEP inhibitor:	0.753

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.015
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.979 ? 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):

2.011

Half-life (T1/2):

1.901

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.065
Human Hepatotoxicity (H-HT):	0.787	Drug-induced Liver Injury (DILI):	0.684
AMES Toxicity:	0.862	Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.169	Skin Sensitization:	0.999
Carcinogencity:	0.452	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.968
Hematotoxicity:	0.406	Drug-induced Nephrotoxicity:	0.898
Genotoxicity:	0.981	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.353	Hek293 Cytotoxicity:	0.216
BCF:	0.558 ? 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:	3.376 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.2 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.333 ? 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
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346966]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root bark	n.a.	n.a.	PMID[14527554]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	tuber	n.a.	PMID[15180301]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	leaves,?stems	USA	n.a.	PMID[16124770]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17291040]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17381154]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078313]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root and trunk bark	n.a.	n.a.	PMID[18078313]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23668986]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25843525]
NPO22563	Sclerocarya birrea	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37463294]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760078]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377017]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20328	Plumeria acutifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20772	Pedalium murex	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21090	Chrysanthemum ornatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20328	Plumeria acutifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21914	Turnera angustifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20772	Pedalium murex	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20262	Delia paludosa	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22563	Sclerocarya birrea	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22700	Dacrydium comosum	Species	Podocarpaceae	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
IZ	1
Activity	3

Activity Type	# Activity
Organism	4

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
NPT20	Organism	Candida albicans	Candida albicans	IZ	<	1.0	mm	PMID[7760078]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	46.59	%	PMID[7760078]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	9.91	%	PMID[7760078]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	10.0	%	PMID[7760078]

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 NPC13710 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	18330
0.1-0.2	27037
0.2-0.3	4204
0.3-0.4	276
0.4-0.5	5
0.5-0.6	3
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	Natural Product ID
0.7349	Intermediate Similarity	NPC470829
0.7108	Intermediate Similarity	NPC473228
0.7027	Intermediate Similarity	NPC47834
0.5595	Remote Similarity	NPC485046
0.5595	Remote Similarity	NPC485047
0.5529	Remote Similarity	NPC66110

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC13710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7058
0.1-0.2	2034
0.2-0.3	55
0.3-0.4	3
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