NPASS Compound

Natural Product: NPC238943

Natural Product ID	NPC238943
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZQDOJGMOEVMUEY-MXAFTYQDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101781233
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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

Chemical Representations

RDKit 2D 97102 0 0 0 0 0 0 0 0999 V2000 1.5905 -12.5203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 -11.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3509 -11.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -9.7441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3509 -8.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 -8.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 -6.9678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -6.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8886 -5.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2981 -4.5264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -3.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4095 -2.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -4.0753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -1.1209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2981 0.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8366 0.6937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4472 1.3205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1867 2.7977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3358 3.7619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0753 5.2391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2244 6.2033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6339 5.6903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8944 4.2131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 3.2489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3039 3.7000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5644 2.2228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7830 6.6545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9639 7.6805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1130 8.6447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 -3.5623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -6.0037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6009 -9.7441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6114 -6.9678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5481 -8.7799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0586 -11.5562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0677 -12.7808 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7944 -12.4786 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3300 -13.9975 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2605 -11.5562 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3926 -11.8392 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6571 -10.5610 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0586 -7.9320 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3125 -8.1077 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7753 -4.8546 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8366 -7.0266 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6386 -6.3385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7981 -4.5264 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3086 -1.7502 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6595 -0.7860 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -1.1209 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -7.7942 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5861 1.2173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8567 0.8075 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7772 3.3108 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6658 5.7522 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0058 1.7717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0416 2.4833 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0872 1.9624 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8249 0.7456 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1925 6.1414 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1488 9.7938 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0772 7.4956 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2620 9.6089 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1172 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 -6.5167 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 -6.1290 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9577 -9.2929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3166 -10.7392 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 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 30 33 1 0 22 34 1 0 20 35 1 0 12 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 2 0 40 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 47 48 1 0 44 49 1 0 43 50 1 0 50 51 1 0 11 52 1 0 10 53 1 0 6 54 1 0 5 55 1 0 4 56 1 0 3 57 1 0 54 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 46 41 1 0 24 19 1 0 1 58 1 0 1 59 1 0 1 60 1 0 2 61 1 6 3 62 1 1 4 63 1 6 5 64 1 6 6 65 1 1 8 66 1 0 8 67 1 0 9 68 1 6 10 69 1 1 11 70 1 6 12 71 1 1 13 72 1 6 21 73 1 0 23 74 1 0 28 75 1 0 29 76 1 0 31 77 1 0 32 78 1 0 33 79 1 0 34 80 1 0 35 81 1 0 39 82 1 0 40 83 1 0 42 84 1 0 46 85 1 0 48 86 1 0 48 87 1 0 48 88 1 0 49 89 1 0 51 90 1 0 51 91 1 0 51 92 1 0 52 93 1 0 53 94 1 0 55 95 1 0 56 96 1 0 57 97 1 0 M END

Standard InCHIKey	ZQDOJGMOEVMUEY-MXAFTYQDSA-N
Standard InCHI	InChI=1S/C38H40O19/c1-15-27(43)31(47)33(49)37(53-15)52-14-24-29(45)32(48)36(56-25(42)9-4-16-10-22(50-2)28(44)23(11-16)51-3)38(55-24)57-35-30(46)26-20(41)12-19(40)13-21(26)54-34(35)17-5-7-18(39)8-6-17/h4-13,15,24,27,29,31-33,36-41,43-45,47-49H,14H2,1-3H3/b9-4+/t15-,24+,27-,29+,31+,32-,33+,36+,37+,38-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(cc2)O)O)O)OC(=O)/C=C/c2cc(c(c(c2)OC)O)OC)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	800.22	Volume:	747.205 ? Van der Waals volume.
Dense:	1.071	LogP:	1.158 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.418 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.941 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	38.0
TPSA:	293.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.074	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.124	Fsp³:	0.368
MCE-18:	142.154 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.732	Fluc inhibitor:	0.645 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.748 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.696 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.093	Promiscuous compounds:	0.46

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.19	MDCK Permeability:	-5.426
Pgp-inhibitor:	0.003	Pgp-substrate:	0.847
PAMPA:	0.976 ? 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):	0.013
20% Bioavailability (F20%):	0.122	30% Bioavailability (F30%):	0.949
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.36
Plasma Protein Binding (PPB):	88.578%	Volume Distribution (VD):	-0.079
Fu:	9.028% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.987
BSEP inhibitor:	0.733

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.675
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.911 ? 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):

0.958

Half-life (T1/2):

4.139

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.261
Human Hepatotoxicity (H-HT):	0.429	Drug-induced Liver Injury (DILI):	0.853
AMES Toxicity:	0.8	Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.194	Skin Sensitization:	0.995
Carcinogencity:	0.074	Eye Corrosion:	0.0
Eye Irritation:	0.107	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.861
Hematotoxicity:	0.027	Drug-induced Nephrotoxicity:	0.28
Genotoxicity:	0.929	RPMI-8226 Immunitoxicity:	0.234
A549 Cytotoxicity:	0.74	Hek293 Cytotoxicity:	0.922
BCF:	0.621 ? 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:	3.467 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.785 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.136 ? 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
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	bud covers	n.a.	n.a.	PMID[11975520]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[12662107]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16643051]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[16989517]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3839140]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7684040]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9868153]
NPO10892	Xanthorrhoea resinosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5380	Eucalyptus australiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10594	Centaurea solstitialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14075	Streptomyces viridogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12726	Piptostigma fugax	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO875	Cryptocarya oblata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7608	Phelline lucida	Species	Phellinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13192	Chara ceratophylla	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16013	Inga velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12726	Piptostigma fugax	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12035	Rhododendron ungerni	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20585	Urochloa decumbens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16306	Curcuma caesia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13683	Cosmos diversifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9342	Solenopsis punctaticeps	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO206	Ormosia nobilis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1398	Trichodesma incanum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11046	Ocimum pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10892	Xanthorrhoea resinosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10594	Centaurea solstitialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5380	Eucalyptus australiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12207	Lagochilus leiacanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14075	Streptomyces viridogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10928	Xenia obscuronata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3059	Erythrina pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2046	Cathormion altissimum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12557	Strychnos tricalysioides	Species	Loganiaceae	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 NPC238943 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	16150
0.1-0.2	29366
0.2-0.3	3445
0.3-0.4	522
0.4-0.5	186
0.5-0.6	118
0.6-0.7	49
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8785	High Similarity	NPC473554
0.8208	Intermediate Similarity	NPC162394
0.7778	Intermediate Similarity	NPC487500
0.7547	Intermediate Similarity	NPC173837
0.7525	Intermediate Similarity	NPC12013
0.7525	Intermediate Similarity	NPC11432
0.7525	Intermediate Similarity	NPC477613
0.7308	Intermediate Similarity	NPC89127
0.7238	Intermediate Similarity	NPC221342
0.7238	Intermediate Similarity	NPC476470
0.7196	Intermediate Similarity	NPC89052
0.717	Intermediate Similarity	NPC218161
0.717	Intermediate Similarity	NPC602448
0.7131	Intermediate Similarity	NPC487501
0.6952	Remote Similarity	NPC122467
0.6942	Remote Similarity	NPC249560
0.686	Remote Similarity	NPC487502
0.678	Remote Similarity	NPC25946
0.675	Remote Similarity	NPC231787
0.6639	Remote Similarity	NPC72554
0.6638	Remote Similarity	NPC474522
0.6635	Remote Similarity	NPC173582
0.6635	Remote Similarity	NPC265885
0.6635	Remote Similarity	NPC181465
0.6635	Remote Similarity	NPC215710
0.6635	Remote Similarity	NPC473438
0.6635	Remote Similarity	NPC253788
0.6612	Remote Similarity	NPC275977
0.6574	Remote Similarity	NPC142142
0.6525	Remote Similarity	NPC241781
0.6481	Remote Similarity	NPC473327
0.6455	Remote Similarity	NPC292929
0.6429	Remote Similarity	NPC97817
0.641	Remote Similarity	NPC470713
0.6408	Remote Similarity	NPC476215
0.6404	Remote Similarity	NPC303694
0.6371	Remote Similarity	NPC30011
0.6364	Remote Similarity	NPC476472
0.6364	Remote Similarity	NPC294815
0.6364	Remote Similarity	NPC16194
0.6356	Remote Similarity	NPC156785
0.6311	Remote Similarity	NPC21359
0.6311	Remote Similarity	NPC460984
0.6271	Remote Similarity	NPC480445
0.6198	Remote Similarity	NPC192539
0.6176	Remote Similarity	NPC216496
0.6168	Remote Similarity	NPC163242
0.6168	Remote Similarity	NPC272068
0.6154	Remote Similarity	NPC470718
0.6129	Remote Similarity	NPC487499
0.6126	Remote Similarity	NPC221288
0.6126	Remote Similarity	NPC194836
0.6126	Remote Similarity	NPC91493
0.6126	Remote Similarity	NPC605081
0.6121	Remote Similarity	NPC470712
0.6111	Remote Similarity	NPC203259
0.6111	Remote Similarity	NPC33054
0.6111	Remote Similarity	NPC176740
0.6111	Remote Similarity	NPC471725
0.6111	Remote Similarity	NPC134532
0.6111	Remote Similarity	NPC602582
0.6071	Remote Similarity	NPC85751
0.6071	Remote Similarity	NPC19240
0.5965	Remote Similarity	NPC483767
0.5965	Remote Similarity	NPC483769
0.5965	Remote Similarity	NPC483768
0.5965	Remote Similarity	NPC483766
0.5929	Remote Similarity	NPC220173
0.5917	Remote Similarity	NPC488734
0.5917	Remote Similarity	NPC488735
0.5917	Remote Similarity	NPC488739
0.5917	Remote Similarity	NPC488732
0.5917	Remote Similarity	NPC488738
0.5913	Remote Similarity	NPC214621
0.5913	Remote Similarity	NPC34267
0.5913	Remote Similarity	NPC483765
0.5909	Remote Similarity	NPC473571
0.5909	Remote Similarity	NPC110941
0.5902	Remote Similarity	NPC480444
0.5888	Remote Similarity	NPC95866
0.5862	Remote Similarity	NPC203145
0.5847	Remote Similarity	NPC217520
0.5847	Remote Similarity	NPC25523
0.5841	Remote Similarity	NPC101399
0.5841	Remote Similarity	NPC217822
0.5841	Remote Similarity	NPC11847
0.5841	Remote Similarity	NPC198938
0.5841	Remote Similarity	NPC603079
0.582	Remote Similarity	NPC470717
0.5785	Remote Similarity	NPC474093
0.5785	Remote Similarity	NPC104910
0.578	Remote Similarity	NPC471079
0.5778	Remote Similarity	NPC33083
0.5772	Remote Similarity	NPC470720
0.5763	Remote Similarity	NPC477895
0.5755	Remote Similarity	NPC224530
0.5752	Remote Similarity	NPC104883
0.5752	Remote Similarity	NPC488679
0.5727	Remote Similarity	NPC39834
0.5726	Remote Similarity	NPC488737
0.569	Remote Similarity	NPC223426
0.568	Remote Similarity	NPC480443
0.5676	Remote Similarity	NPC155877
0.5676	Remote Similarity	NPC304741
0.5648	Remote Similarity	NPC170052
0.5648	Remote Similarity	NPC135846
0.5631	Remote Similarity	NPC111929
0.5631	Remote Similarity	NPC320283
0.5631	Remote Similarity	NPC41121
0.562	Remote Similarity	NPC139571
0.5603	Remote Similarity	NPC260504
0.5603	Remote Similarity	NPC89809
0.56	Remote Similarity	NPC209550
0.5565	Remote Similarity	NPC488740
0.5565	Remote Similarity	NPC488736
0.5565	Remote Similarity	NPC488733
0.5546	Remote Similarity	NPC470416
0.5546	Remote Similarity	NPC189564
0.5536	Remote Similarity	NPC65563
0.5536	Remote Similarity	NPC470949
0.5514	Remote Similarity	NPC219904
0.5508	Remote Similarity	NPC478277
0.5508	Remote Similarity	NPC96605
0.5508	Remote Similarity	NPC280642
0.5508	Remote Similarity	NPC478276
0.5508	Remote Similarity	NPC478275
0.5508	Remote Similarity	NPC92815
0.5508	Remote Similarity	NPC81042
0.5487	Remote Similarity	NPC129264
0.5487	Remote Similarity	NPC470444
0.5487	Remote Similarity	NPC186816
0.5455	Remote Similarity	NPC164704
0.5446	Remote Similarity	NPC470405
0.5439	Remote Similarity	NPC470125
0.5439	Remote Similarity	NPC126784
0.5439	Remote Similarity	NPC240306
0.5439	Remote Similarity	NPC241423
0.5439	Remote Similarity	NPC153755
0.5431	Remote Similarity	NPC97119
0.5413	Remote Similarity	NPC223747
0.5403	Remote Similarity	NPC295625
0.5398	Remote Similarity	NPC156869
0.5385	Remote Similarity	NPC470447
0.5357	Remote Similarity	NPC609888
0.5351	Remote Similarity	NPC35167
0.5345	Remote Similarity	NPC270448
0.5339	Remote Similarity	NPC36138
0.5328	Remote Similarity	NPC480441
0.5321	Remote Similarity	NPC259957
0.5317	Remote Similarity	NPC470719
0.531	Remote Similarity	NPC67326
0.5304	Remote Similarity	NPC61904
0.5299	Remote Similarity	NPC205824
0.5271	Remote Similarity	NPC480442
0.5229	Remote Similarity	NPC48093
0.5221	Remote Similarity	NPC187379
0.5217	Remote Similarity	NPC255157
0.5217	Remote Similarity	NPC259896
0.521	Remote Similarity	NPC470449
0.5203	Remote Similarity	NPC470715
0.5179	Remote Similarity	NPC254855
0.5179	Remote Similarity	NPC116864
0.5179	Remote Similarity	NPC244776
0.5179	Remote Similarity	NPC94610
0.5172	Remote Similarity	NPC296018
0.514	Remote Similarity	NPC127546
0.514	Remote Similarity	NPC57625
0.514	Remote Similarity	NPC173637
0.514	Remote Similarity	NPC317489
0.514	Remote Similarity	NPC223424
0.514	Remote Similarity	NPC600591
0.5128	Remote Similarity	NPC470443
0.5126	Remote Similarity	NPC76831
0.5122	Remote Similarity	NPC219043
0.5122	Remote Similarity	NPC292019
0.5122	Remote Similarity	NPC48984
0.5122	Remote Similarity	NPC202908
0.5093	Remote Similarity	NPC265530
0.5091	Remote Similarity	NPC159579
0.5088	Remote Similarity	NPC258044
0.5088	Remote Similarity	NPC217387

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC238943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4979
0.1-0.2	4118
0.2-0.3	44
0.3-0.4	4
0.4-0.5	4
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
0.6111	Remote Similarity	NPD6797	Phase 2

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