NPASS Compound

Natural Product: NPC291407

Natural Product ID	NPC291407
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FUNWNVWJOMCWIL-WZPNJOEPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11622083
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 99106 0 0 0 0 0 0 0 0999 V2000 -3.1773 1.9005 -1.8710 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4090 3.2473 -1.7027 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5987 3.6667 -1.1669 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5315 2.7136 -0.8114 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2929 1.3682 -0.9821 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0890 0.9339 -1.5246 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9070 -0.5243 -1.6716 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2769 -1.1875 -0.4526 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8153 -1.1879 -0.6083 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5376 -2.0800 -1.7606 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6143 -3.0798 -1.7741 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4490 -3.8356 -2.9232 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1886 -3.6092 -4.0561 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1141 -2.5908 -4.0124 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2957 -1.8273 -2.8826 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2589 -0.7840 -2.8770 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0063 -4.3887 -5.2147 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1917 -3.3774 -0.6503 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9914 -1.5739 0.5039 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3085 -2.5905 1.3740 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4485 -2.8459 2.4188 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7128 -2.1111 2.6066 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0533 -1.0854 1.7436 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2903 -0.3565 1.9964 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6060 0.7558 1.0462 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7850 0.8206 -0.1944 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5764 0.4146 -1.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7096 -0.8962 -1.8090 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4405 -1.2254 -2.9371 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0629 -0.2371 -3.7061 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9374 1.0799 -3.3222 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2130 1.3689 -2.2099 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5657 2.0550 -4.1026 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8019 -0.5462 -4.8436 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5724 -2.5542 -3.3325 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5489 0.1902 -0.1425 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1888 -0.8453 0.7140 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9788 0.6350 0.7301 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8390 1.6492 1.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4334 2.6861 1.7040 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2694 1.5805 0.8013 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1307 2.5905 1.1505 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4583 2.4981 0.8697 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9771 1.3950 0.2302 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0964 0.3862 -0.1150 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7497 0.4590 0.1592 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6467 -0.7290 -0.7656 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3484 1.3332 -0.0428 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2807 3.5699 1.2568 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5444 -2.4089 3.6743 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4813 -3.3517 1.1995 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8367 -0.5165 0.6406 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7783 -0.9786 1.5090 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2409 -2.1385 1.3496 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2420 -0.1326 2.6120 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7707 1.1388 2.8394 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2514 1.8949 3.9080 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2069 1.4007 4.7672 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6946 0.1180 4.5525 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2142 -0.6114 3.5011 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6596 -0.3611 5.4331 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6710 2.1745 5.8271 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7752 3.1897 4.1448 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7454 3.1302 -0.2660 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9032 5.0095 -0.9678 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2252 1.5868 -2.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6522 3.9515 -1.9951 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0608 0.6550 -0.6854 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9301 -1.0056 -1.7812 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6846 -2.2292 -0.4525 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4997 -0.1621 -0.9453 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3072 -4.6408 -2.9067 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7238 -2.3762 -4.8963 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1918 -4.1473 -5.7759 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2215 -4.3267 -0.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7041 -3.6511 3.1058 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3113 0.0565 3.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1115 -1.1367 2.0307 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4951 1.7408 1.5891 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5441 1.9119 -0.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2510 -1.6702 -1.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1178 2.4066 -1.9135 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4326 1.8367 -4.6100 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7417 -1.4966 -5.2427 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6173 -3.3291 -2.6893 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6881 3.4603 1.6608 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0969 -0.3598 -0.1307 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0508 -1.3507 -1.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0381 1.6921 0.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1287 4.0288 2.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5667 -2.4134 3.5319 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0322 -3.6871 1.9658 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0269 1.5671 2.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6114 -1.6160 3.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0587 -1.2903 5.2408 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6296 2.0861 6.1796 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3311 3.8991 4.5690 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7953 3.8482 0.4258 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7905 5.3757 -1.2798 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 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 13 17 1 0 11 18 1 0 9 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 29 35 1 0 26 36 1 0 36 37 1 0 25 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 45 47 1 0 44 48 1 0 43 49 1 0 22 50 1 0 20 51 1 0 8 52 1 0 52 53 1 0 53 54 2 0 53 55 1 0 55 56 2 0 56 57 1 0 57 58 2 0 58 59 1 0 59 60 2 0 59 61 1 0 58 62 1 0 57 63 1 0 4 64 1 0 3 65 1 0 6 1 1 0 16 7 1 0 37 19 1 0 46 41 1 0 60 55 1 0 15 10 1 0 37 23 2 0 32 27 1 0 1 66 1 0 2 67 1 0 5 68 1 0 7 69 1 6 8 70 1 1 9 71 1 6 12 72 1 0 14 73 1 0 17 74 1 0 18 75 1 0 21 76 1 0 24 77 1 0 24 78 1 0 25 79 1 1 26 80 1 6 28 81 1 0 32 82 1 0 33 83 1 0 34 84 1 0 35 85 1 0 42 86 1 0 46 87 1 0 47 88 1 0 48 89 1 0 49 90 1 0 50 91 1 0 51 92 1 0 56 93 1 0 60 94 1 0 61 95 1 0 62 96 1 0 63 97 1 0 64 98 1 0 65 99 1 0 M END

Standard InCHIKey	FUNWNVWJOMCWIL-WZPNJOEPSA-N
Standard InCHI	InChI=1S/C44H34O21/c45-18-10-23(49)33-31(11-18)62-40(14-1-2-20(46)22(48)3-14)42(65-44(61)17-8-29(55)38(59)30(56)9-17)35(33)34-24(50)13-21(47)19-12-32(63-43(60)16-6-27(53)37(58)28(54)7-16)39(64-41(19)34)15-4-25(51)36(57)26(52)5-15/h1-11,13,32,35,39-40,42,45-59H,12H2/t32-,35-,39-,40-,42-/m1/s1
SMILES	c1cc(c(cc1[C@@H]1[C@@H]([C@H](c2c(cc(cc2O1)O)O)c1c(cc(c2C[C@H]([C@@H](c3cc(c(c(c3)O)O)O)Oc12)OC(=O)c1cc(c(c(c1)O)O)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	898.16	Volume:	832.994 ? Van der Waals volume.
Dense:	1.078	LogP:	1.448 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.232 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.692 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	48.0
TPSA:	374.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	15.0	Rings:	8.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.076	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.266	Fsp³:	0.136
MCE-18:	178.2 ? 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:	1.0	Fluc inhibitor:	0.346 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.349 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.661 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.721	Promiscuous compounds:	0.638

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-8.006	MDCK Permeability:	-4.724
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	0.588 ? 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%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	89.054%	Volume Distribution (VD):	-0.157
Fu:	10.516% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.872
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.911
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:	0.0 ? 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):

5.527

Half-life (T1/2):

4.882

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.993
Human Hepatotoxicity (H-HT):	0.105	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.943	Rat Oral Acute Toxicity:	0.581
Maximum Recommended Daily Dose:	0.994	Skin Sensitization:	1.0
Carcinogencity:	0.07	Eye Corrosion:	0.0
Eye Irritation:	0.967	Respiratory Toxicity:	0.533
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.968
BCF:	0.78 ? 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:	3.745 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.911 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.399 ? 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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 16712885]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075766]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11112781]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[153409]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568769]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[17190463]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17870137]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[18239317]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[18239317]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18462007]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO21036	Celaenodendron mexicanum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19299148]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21673922]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317005]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23488669]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27524650]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29115831]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31182315]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31287310]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37255739]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21918	Aconitum heterophylloides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18859	Carica pennata	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21036	Celaenodendron mexicanum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19969	Dermocybe canaria	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17130	Hylotelephium telephium	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21164	Veratrum dahuricum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21542	Vernonia menthaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8808	Artemisia schimperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11558	Atylosia trinervia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27848	Conoideocrella luteorostrata	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9930	Dendrodoris tuberculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12893	Dermolepida albohirtum	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8777	Euryops algoensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4544	Gomortega keule	Species	Gomortegaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11949	Iris ensata	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6259	Keiferia lycopersicella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12317	Naja kaouthia	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12677	Penicillium kapuscinskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13002	Petasites georgicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1038	Phoenix loureiroi	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7050	Picea mariana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11709	Salvia parryi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12081	Streptomyces xanthochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8492	Viburnum urceolatum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7347	Viguiera oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8492	Viburnum urceolatum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27848	Conoideocrella luteorostrata	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1038	Phoenix loureiroi	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9930	Dendrodoris tuberculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17130	Hylotelephium telephium	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12677	Penicillium kapuscinskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6259	Keiferia lycopersicella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12081	Streptomyces xanthochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12893	Dermolepida albohirtum	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4544	Gomortega keule	Species	Gomortegaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11709	Salvia parryi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8777	Euryops algoensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11949	Iris ensata	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7050	Picea mariana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21164	Veratrum dahuricum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18859	Carica pennata	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13002	Petasites georgicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7347	Viguiera oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11558	Atylosia trinervia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21542	Vernonia menthaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21036	Celaenodendron mexicanum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12317	Naja kaouthia	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19969	Dermocybe canaria	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8808	Artemisia schimperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21918	Aconitum heterophylloides	Species	Ranunculaceae	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
NPO8258	Camellia sinensis	Tea Or Coffee	Plant	0.4	0.4	0.4	mg/100g	Database [DUKE]

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 NPC291407 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	24143
0.1-0.2	22991
0.2-0.3	2489
0.3-0.4	135
0.4-0.5	75
0.5-0.6	7
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC98583
0.9091	High Similarity	NPC100251
0.7733	Intermediate Similarity	NPC135021
0.7353	Intermediate Similarity	NPC38779
0.7353	Intermediate Similarity	NPC114179
0.7353	Intermediate Similarity	NPC68324
0.7353	Intermediate Similarity	NPC289322
0.7353	Intermediate Similarity	NPC160512
0.6974	Remote Similarity	NPC65333
0.662	Remote Similarity	NPC156818
0.6618	Remote Similarity	NPC291948
0.6618	Remote Similarity	NPC104983
0.6618	Remote Similarity	NPC250436
0.6618	Remote Similarity	NPC300845
0.6618	Remote Similarity	NPC88803
0.6351	Remote Similarity	NPC601196
0.6164	Remote Similarity	NPC474656
0.5897	Remote Similarity	NPC53889
0.5769	Remote Similarity	NPC603842
0.5641	Remote Similarity	NPC87317
0.5432	Remote Similarity	NPC603291
0.5062	Remote Similarity	NPC40222
0.5062	Remote Similarity	NPC268515
0.5057	Remote Similarity	NPC602382

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC291407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5279
0.1-0.2	3835
0.2-0.3	30
0.3-0.4	2
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
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
0.6618	Remote Similarity	NPD4868	Phase 3

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