NPASS Compound

Natural Product: NPC302170

Natural Product ID	NPC302170
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NLDMNSXOCDLTTB-LQZDAVIGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10056061
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 82 87 0 0 0 0 0 0 0 0999 V2000 -1.8703 4.8561 -1.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8177 3.9250 -0.6059 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1656 4.3470 0.6569 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5551 5.6635 0.8990 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5923 6.5625 -0.1507 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2489 6.1574 -1.4130 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2891 7.0635 -2.4569 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9841 7.8754 0.1088 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9006 6.0624 2.1814 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4167 2.5657 -0.8467 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0999 2.2122 -2.0352 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3562 1.6101 0.1572 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9454 0.3093 -0.2143 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2587 -0.5111 -0.0918 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0898 -1.9554 -0.3602 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0628 -2.4600 0.4846 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0572 -1.8141 0.1337 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3419 -2.4751 0.5883 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4067 -1.7869 0.0007 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7121 -2.0895 0.1323 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1451 -3.0075 0.7957 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6471 -1.2339 -0.5997 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1518 -1.9256 -1.7413 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0071 -1.2789 -2.5969 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3523 0.0183 -2.3269 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8584 0.6554 -1.2297 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9857 0.0140 -0.3429 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6311 0.8021 0.8198 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4429 1.2384 1.2202 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 2.0758 2.3738 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4645 2.4440 3.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6953 1.9730 2.6476 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7678 1.1857 1.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9923 0.7184 1.1313 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8474 2.3485 3.3802 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4154 3.2556 4.2065 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0776 1.0299 0.7284 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6342 1.9417 0.0104 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2477 0.0109 0.9572 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0038 -0.3680 0.6654 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1937 1.9920 -0.9234 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2172 0.6826 -3.1888 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4911 -1.9697 -3.7088 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2690 -2.6189 0.0513 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9552 -3.4266 -0.8497 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4588 -3.5114 -2.0084 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1588 -4.1419 -0.5313 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7615 -4.9150 -1.4971 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9342 -5.6300 -1.2332 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4980 -5.5634 0.0077 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9190 -4.7992 0.9937 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7464 -4.0899 0.7146 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5309 -4.7671 2.2314 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6697 -6.2740 0.2815 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5001 -6.3974 -2.2527 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2680 0.0965 -0.7967 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6004 4.5424 -2.6170 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1392 3.6572 1.4744 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8301 7.9158 -2.3667 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9828 8.0757 0.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5797 5.4781 2.6711 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7063 0.2287 -1.3060 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5231 -0.4022 1.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8553 -2.1856 -1.4193 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0774 -1.7288 -0.9902 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3924 -2.5341 1.6853 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3335 -3.5108 0.1935 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8308 -2.9532 -1.8605 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3617 2.4308 2.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7373 0.5587 1.7850 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0863 1.9048 4.2474 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5229 3.6266 4.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5739 -0.5272 1.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9291 2.6581 -1.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1709 0.3573 -3.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1534 -2.7156 -3.4954 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3556 -5.0026 -2.4981 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3160 -3.5046 1.4944 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0262 -4.5976 3.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9485 -6.5660 1.1915 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2153 -7.3808 -2.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7790 -0.5077 -1.3908 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 5 8 1 0 4 9 1 0 2 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 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 2 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 32 35 1 0 31 36 1 0 29 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 26 41 1 0 25 42 1 0 24 43 1 0 15 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 51 53 1 0 50 54 1 0 49 55 1 0 14 56 1 0 6 1 1 0 40 13 1 0 52 47 1 0 40 17 1 0 27 22 1 0 33 28 1 0 1 57 1 0 3 58 1 0 7 59 1 0 8 60 1 0 9 61 1 0 13 62 1 6 14 63 1 1 15 64 1 6 17 65 1 6 18 66 1 0 18 67 1 0 23 68 1 0 30 69 1 0 34 70 1 0 35 71 1 0 36 72 1 0 40 73 1 1 41 74 1 0 42 75 1 0 43 76 1 0 48 77 1 0 52 78 1 0 53 79 1 0 54 80 1 0 55 81 1 0 56 82 1 0 M END

Standard InCHIKey	NLDMNSXOCDLTTB-LQZDAVIGSA-N
Standard InCHI	InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(48)55-29-27(47)34(56-31(49)9-3-14(37)22(42)15(38)4-9)53-18-7-52-32(50)10-5-16(39)23(43)25(45)19(10)20-11(33(51)54-28(18)29)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-47H,7H2/t18-,27-,28-,29-,34+/m1/s1
SMILES	c1c(cc(c(c1O)O)O)C(=O)O[C@@H]1[C@H]([C@@H](O[C@@H]2COC(=O)c3cc(c(c(c3-c3c(cc(c(c3O)O)O)C(=O)O[C@@H]12)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	786.09	Volume:	696.483 ? Van der Waals volume.
Dense:	1.129	LogP:	-0.149 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.079 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.037 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	42.0
TPSA:	377.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.077	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.402	Fsp³:	0.176
MCE-18:	148.5 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.987	Fluc inhibitor:	0.104 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.446 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.657 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.543	Promiscuous compounds:	0.986

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.377	MDCK Permeability:	-4.723
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	1.0 ? 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%):	0.619	30% Bioavailability (F30%):	0.953
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	74.235%	Volume Distribution (VD):	-0.152
Fu:	16.958% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.649
OATP1B3 inhibitor:	0.688	BCRP inhibitor:	0.094
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.014 ? 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):

4.539

Half-life (T1/2):

4.74

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.981
Human Hepatotoxicity (H-HT):	0.117	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.988	Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.833	Skin Sensitization:	1.0
Carcinogencity:	0.204	Eye Corrosion:	0.0
Eye Irritation:	0.963	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.008
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.263
BCF:	0.183 ? 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:	3.181 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.029 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.052 ? 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
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO20417	Tamarix nilotica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20405847]
NPO20417	Tamarix nilotica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23675651]
NPO20786	Tamarix tetrandra	Species	Tamaricaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26938659]
NPO20417	Tamarix nilotica	Species	Tamaricaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26938659]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[31301930]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34770801]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36985392]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836118]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39684253]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39699537]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964790]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1456	Bersama abyssinica	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5834	Pellicularia sasakii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20786	Tamarix tetrandra	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9233	Plexaura homomalla	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20417	Tamarix nilotica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2395	Siphonaria australis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20417	Tamarix nilotica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO173	Aconitum sajanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6072	Andinobates bombetes	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12409	Artemisia jacutica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5834	Pellicularia sasakii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6041	Lithocolletis coryli	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9456	Rubus sanctus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15735	Galeocerdo arcticus	Species	Carcharhinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1456	Bersama abyssinica	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7383	Puccinia lagenophorae	Species	Pucciniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9233	Plexaura homomalla	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2395	Siphonaria australis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20786	Tamarix tetrandra	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5859	Bacterium sa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20417	Tamarix nilotica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO199	Dryopteris aitoniana	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4504	Cassia jahnii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4351	Hedyosmum arborescens	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9718	Cyphelium chrysocephalum	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9598	Psorospermum adamauense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8941	Salacia longipes	Species	Sertulariidae	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
CC50	7

Activity Type	# Activity
Cell line	4
Others	3

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
NPT116	Cell line	HL-60	Homo sapiens	CC50	=	39900.0	nM	PMID[26938659]
NPT2394	Cell line	HSC-4	Homo sapiens	CC50	=	38000.0	nM	PMID[26938659]
NPT2385	Cell line	HSC-3	Homo sapiens	CC50	=	28000.0	nM	PMID[26938659]
NPT924	Cell line	HSC-2	Homo sapiens	CC50	=	14100.0	nM	PMID[26938659]
NPT2	Others	Unspecified	n.a.	CC50	>	100000.0	nM	PMID[26938659]

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 NPC302170 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	19863
0.1-0.2	28951
0.2-0.3	857
0.3-0.4	69
0.4-0.5	67
0.5-0.6	30
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8182	Intermediate Similarity	NPC470271
0.807	Intermediate Similarity	NPC238419
0.746	Intermediate Similarity	NPC291957
0.7167	Intermediate Similarity	NPC283806
0.7031	Intermediate Similarity	NPC488888
0.7031	Intermediate Similarity	NPC14030
0.6769	Remote Similarity	NPC43918
0.6769	Remote Similarity	NPC261411
0.6769	Remote Similarity	NPC190204
0.6667	Remote Similarity	NPC469651
0.6615	Remote Similarity	NPC47521
0.6479	Remote Similarity	NPC470898
0.6471	Remote Similarity	NPC311389
0.6154	Remote Similarity	NPC481310
0.6129	Remote Similarity	NPC16024
0.6119	Remote Similarity	NPC175793
0.6119	Remote Similarity	NPC159913
0.5938	Remote Similarity	NPC205037
0.5938	Remote Similarity	NPC3746
0.5814	Remote Similarity	NPC65489
0.5733	Remote Similarity	NPC8940
0.5696	Remote Similarity	NPC80956
0.5538	Remote Similarity	NPC61152
0.5538	Remote Similarity	NPC125546
0.5495	Remote Similarity	NPC479371
0.5467	Remote Similarity	NPC217781
0.5435	Remote Similarity	NPC479373
0.5373	Remote Similarity	NPC31034
0.5366	Remote Similarity	NPC112211
0.5366	Remote Similarity	NPC254925
0.5244	Remote Similarity	NPC481308
0.5238	Remote Similarity	NPC223534
0.5238	Remote Similarity	NPC483712
0.5238	Remote Similarity	NPC158214
0.5238	Remote Similarity	NPC214202
0.5181	Remote Similarity	NPC481309
0.5176	Remote Similarity	NPC290289
0.5169	Remote Similarity	NPC111490
0.5169	Remote Similarity	NPC261623
0.5152	Remote Similarity	NPC114791
0.5152	Remote Similarity	NPC104222
0.5152	Remote Similarity	NPC210501
0.5152	Remote Similarity	NPC318826
0.5152	Remote Similarity	NPC141331
0.5104	Remote Similarity	NPC220876
0.5059	Remote Similarity	NPC470272
0.5059	Remote Similarity	NPC97924

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC302170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5756
0.1-0.2	3375
0.2-0.3	18
0.3-0.4	1
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