NPASS Compound

Natural Product: NPC53475

Natural Product ID	NPC53475
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MQYXUWHLBZFQQO-KTMBBHICSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 81 85 0 0 0 0 0 0 0 0999 V2000 -3.5192 3.0074 0.3790 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9119 2.5783 -0.8022 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5546 3.5709 -1.7465 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7383 1.1701 -1.2085 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1668 0.5984 -1.2934 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2084 -0.5367 -0.2558 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7576 -1.0116 -0.4445 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6636 -1.5417 -1.8165 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3097 -1.9290 0.6354 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8022 -1.9699 0.7504 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1870 -0.6323 0.9811 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7289 0.0020 2.2716 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 0.2833 -0.1366 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9970 -0.0387 -1.4579 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5213 0.0649 -1.2283 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9863 -0.9288 -0.2118 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4817 -0.8986 -0.1863 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0475 -2.1789 0.3100 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9843 -0.6693 -1.6275 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5051 -0.7806 -1.6932 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2268 -0.1207 -0.5894 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4597 0.5122 0.4862 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7428 2.0302 0.4423 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0257 0.1222 1.8644 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9942 0.3457 0.5020 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3595 0.5129 1.8500 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8780 0.5212 1.7374 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3153 -0.7472 1.0962 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5765 -1.8511 2.0852 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1589 0.7873 -1.1623 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1088 0.3374 -0.1848 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0509 2.4522 1.1650 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6801 4.0799 0.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3876 3.2729 -2.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6209 3.7321 -1.4885 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0312 4.5327 -1.5678 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2559 1.1148 -2.2186 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9388 1.3432 -1.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2576 0.1147 -2.2860 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9080 -1.2903 -0.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3908 -0.1615 0.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6770 -1.9185 -2.1663 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0471 -2.4899 -1.8718 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3762 -0.8344 -2.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8255 -1.7769 1.6046 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6093 -2.9742 0.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4408 -2.3219 -0.2590 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5617 -2.7694 1.4382 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4966 1.0863 2.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2072 -0.3709 3.1800 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7901 -0.2474 2.4531 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2527 1.2945 0.1388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2487 0.7584 -2.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1396 -1.0516 -1.8195 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6920 1.1157 -0.9683 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9101 -0.2072 -2.2556 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7038 -1.9437 -0.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0739 -2.4163 -0.0799 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1335 -2.2968 1.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -2.9941 -0.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7933 0.4127 -1.9026 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5631 -1.3830 -2.3318 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7611 -0.3145 -2.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8198 -1.8542 -1.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9169 -0.8955 -0.1322 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2718 2.4417 -0.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2649 2.5422 1.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8331 2.2159 0.3622 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6243 0.7564 2.6627 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1193 0.3998 1.7879 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.9483 2.0394 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5601 1.1888 -0.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8019 -0.1504 2.5841 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6430 1.5567 2.1866 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5995 1.4153 1.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4536 0.7170 2.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8018 -2.8203 1.5935 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3845 -1.5733 2.8290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2647 -2.0740 2.7737 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8404 0.3016 -1.6884 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5053 0.6236 0.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 21 30 1 0 13 31 1 0 31 4 1 0 31 7 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 32 1 0 1 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 4 37 1 6 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 8 42 1 0 8 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 12 49 1 0 12 50 1 0 12 51 1 0 13 52 1 1 14 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 6 18 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 21 65 1 1 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 6 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 31 81 1 1 M END

Standard InCHIKey	MQYXUWHLBZFQQO-KTMBBHICSA-N
Standard InCHI	InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21-,22-,23-,24+,25+,27+,28-,29+,30+/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@@H](CC[C@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.39	Volume:	490.807 ? Van der Waals volume.
Dense:	0.869	LogP:	6.158 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.549 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.034 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.421	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.663	Fsp³:	0.933
MCE-18:	100.793 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.966	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.673	Promiscuous compounds:	0.291

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.108	MDCK Permeability:	-4.854
Pgp-inhibitor:	0.956	Pgp-substrate:	0.001
PAMPA:	0.035 ? 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%):	0.03	30% Bioavailability (F30%):	0.03
50% Bioavailability (F50%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.39	MRP1:	0.448
Plasma Protein Binding (PPB):	94.0%	Volume Distribution (VD):	0.25
Fu:	6.41% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.657
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.97	CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.034	CYP2C9-substrate:	0.805
CYP2D6-inhibitor:	0.968	CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.01	CYP2C8-inhibitor:	0.929
HLM stability:	0.876 ? 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):

16.489

Half-life (T1/2):

0.653

ADMET: Toxicity

hERG Blockers:	0.083	hERG Blockers (10um):	0.355
Human Hepatotoxicity (H-HT):	0.51	Drug-induced Liver Injury (DILI):	0.15
AMES Toxicity:	0.215	Rat Oral Acute Toxicity:	0.194
Maximum Recommended Daily Dose:	0.614	Skin Sensitization:	0.86
Carcinogencity:	0.918	Eye Corrosion:	0.298
Eye Irritation:	0.913	Respiratory Toxicity:	0.887
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.507
Hematotoxicity:	0.335	Drug-induced Nephrotoxicity:	0.549
Genotoxicity:	0.039	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.278	Hek293 Cytotoxicity:	0.467
BCF:	3.284 ? 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:	5.15 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.683 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.099 ? 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
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542364]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15165157]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21627109]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30817151]
NPO8283	Pseudophegopteris subaurita	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10733	Plantago uniflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10479	Ophiocoma echinata	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10959	Kalanchoe marmorata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5571	Jacobaea arnautorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3940	Erioderma chilense	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4494	Ecbolium linneanum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10833	Heteromma simplicifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1000	Thymus transcaucasicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1000	Thymus transcaucasicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10833	Heteromma simplicifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5571	Jacobaea arnautorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4494	Ecbolium linneanum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8283	Pseudophegopteris subaurita	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10733	Plantago uniflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10479	Ophiocoma echinata	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3940	Erioderma chilense	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10959	Kalanchoe marmorata	Species	Crassulaceae	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

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

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 NPC53475 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	27313
0.1-0.2	19099
0.2-0.3	2754
0.3-0.4	484
0.4-0.5	118
0.5-0.6	37
0.6-0.7	22
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC192638
1.0	High Similarity	NPC25511
1.0	High Similarity	NPC600137
0.8542	High Similarity	NPC248830
0.8542	High Similarity	NPC212241
0.82	Intermediate Similarity	NPC269396
0.78	Intermediate Similarity	NPC231256
0.78	Intermediate Similarity	NPC178383
0.76	Intermediate Similarity	NPC202540
0.75	Intermediate Similarity	NPC246956
0.75	Intermediate Similarity	NPC74595
0.75	Intermediate Similarity	NPC142712
0.75	Intermediate Similarity	NPC264665
0.7347	Intermediate Similarity	NPC480925
0.7347	Intermediate Similarity	NPC48079
0.7308	Intermediate Similarity	NPC93662
0.7255	Intermediate Similarity	NPC104387
0.7255	Intermediate Similarity	NPC240235
0.7255	Intermediate Similarity	NPC14112
0.7255	Intermediate Similarity	NPC301226
0.7222	Intermediate Similarity	NPC12774
0.7059	Intermediate Similarity	NPC97534
0.7059	Intermediate Similarity	NPC195155
0.7059	Intermediate Similarity	NPC102708
0.6923	Remote Similarity	NPC144075
0.6863	Remote Similarity	NPC80297
0.6863	Remote Similarity	NPC475727
0.6863	Remote Similarity	NPC116119
0.6852	Remote Similarity	NPC119355
0.6842	Remote Similarity	NPC607755
0.6604	Remote Similarity	NPC78067
0.6604	Remote Similarity	NPC278091
0.6481	Remote Similarity	NPC42853
0.6429	Remote Similarity	NPC298168
0.6429	Remote Similarity	NPC143133
0.6415	Remote Similarity	NPC185536
0.6346	Remote Similarity	NPC35652
0.6296	Remote Similarity	NPC91573
0.625	Remote Similarity	NPC57469
0.6226	Remote Similarity	NPC606606
0.6207	Remote Similarity	NPC471900
0.6182	Remote Similarity	NPC237460
0.6111	Remote Similarity	NPC43300
0.6071	Remote Similarity	NPC296701
0.6071	Remote Similarity	NPC218616
0.6	Remote Similarity	NPC483720
0.5965	Remote Similarity	NPC305835
0.5938	Remote Similarity	NPC475416
0.5882	Remote Similarity	NPC232112
0.5833	Remote Similarity	NPC264317
0.5833	Remote Similarity	NPC294438
0.5789	Remote Similarity	NPC5767
0.5789	Remote Similarity	NPC211009
0.5789	Remote Similarity	NPC475742
0.5763	Remote Similarity	NPC49599
0.5763	Remote Similarity	NPC49627
0.5738	Remote Similarity	NPC33768
0.5714	Remote Similarity	NPC245869
0.569	Remote Similarity	NPC86305
0.569	Remote Similarity	NPC212879
0.5593	Remote Similarity	NPC103754
0.5593	Remote Similarity	NPC126993
0.5574	Remote Similarity	NPC611062
0.5536	Remote Similarity	NPC475679
0.5424	Remote Similarity	NPC13554
0.541	Remote Similarity	NPC477578
0.541	Remote Similarity	NPC477577
0.5345	Remote Similarity	NPC58631
0.5345	Remote Similarity	NPC285761
0.5345	Remote Similarity	NPC34930
0.5345	Remote Similarity	NPC472742
0.5323	Remote Similarity	NPC201406
0.5323	Remote Similarity	NPC289486
0.5312	Remote Similarity	NPC16377
0.5263	Remote Similarity	NPC472741
0.5254	Remote Similarity	NPC159497
0.5254	Remote Similarity	NPC201725
0.5254	Remote Similarity	NPC602784
0.5238	Remote Similarity	NPC481321
0.5238	Remote Similarity	NPC112009
0.5085	Remote Similarity	NPC293803
0.5077	Remote Similarity	NPC151191
0.5068	Remote Similarity	NPC474092

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC53475 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7809
0.1-0.2	1278
0.2-0.3	57
0.3-0.4	5
0.4-0.5	0
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5833	Remote Similarity	NPD7520	Phase 1

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