NPASS Compound

Natural Product: NPC180664

Natural Product ID	NPC180664
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AIBMPOJXBGZIPQ-QWNFCSOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102158614
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 3D 79 83 0 0 0 0 0 0 0 0999 V2000 -3.9217 0.1004 2.4218 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1191 -1.1971 2.4038 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0325 -2.3474 2.6521 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5966 -2.9742 1.4190 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5611 -2.9443 0.2856 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1099 -1.5136 0.1742 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3013 -1.2987 1.3093 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4182 -1.2950 -0.9898 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9317 -0.2713 -1.7775 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2170 -0.6663 -3.2020 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9627 0.5471 -3.7808 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2103 1.8134 -3.5275 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0623 2.7995 -2.7575 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4518 4.0522 -2.6882 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0147 1.6879 -2.9042 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8717 0.8112 -1.8669 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8267 1.4837 -0.6462 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7223 1.5809 0.1290 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8805 2.2964 1.3258 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1385 2.4878 2.2223 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3736 1.9523 1.9321 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3960 2.1438 2.8273 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2181 2.7877 3.8847 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6409 1.5871 2.5016 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8125 0.8839 1.3338 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1054 0.3101 1.0033 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2300 0.4076 1.7696 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4418 -0.1719 1.3885 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5181 -0.8665 0.2047 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3840 -0.9831 -0.6002 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2143 -0.4020 -0.1942 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5269 -1.6972 -1.7828 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4761 -1.9012 -2.6966 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7176 -1.4688 -0.2217 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5782 -0.0688 2.1706 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4910 0.6501 3.3913 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7727 0.7515 0.5352 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5920 1.2504 0.7912 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5252 1.0757 -0.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0240 3.1968 3.4056 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2584 0.3283 -5.1207 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9885 -1.7812 -3.3642 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1087 -3.4839 -0.8434 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7624 -2.2881 1.0305 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4838 -3.3313 3.4800 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0962 0.4136 3.4800 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9366 -0.0436 1.9682 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3405 0.8910 1.9330 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4472 -1.1289 3.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9140 -1.9443 3.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8793 -4.0169 1.6189 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7003 -3.5432 0.6847 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9954 -0.8589 0.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8381 0.1887 -1.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2609 -0.7077 -3.7982 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9236 0.5841 -3.2302 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0295 2.2845 -4.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3044 2.4999 -1.7377 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0027 2.9606 -3.3573 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4769 4.4265 -1.7722 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9122 0.2859 -2.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8460 2.7386 1.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4402 1.7402 3.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1939 0.9463 2.7004 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3477 -0.5051 -0.8336 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7762 -2.6786 -3.4140 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6032 -2.3143 -2.1234 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2078 -0.9899 -3.2586 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4028 -0.8971 -0.7237 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4672 0.6840 3.9159 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7840 0.1465 4.1136 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1259 1.6631 3.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7255 0.5104 -1.0057 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9041 3.6610 3.5584 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2921 1.1763 -5.6478 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8347 -2.1434 -4.2740 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3401 -3.7683 -1.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9389 -2.4359 0.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1753 -3.8588 3.9453 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 6 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 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 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 30 32 1 0 32 33 1 0 29 34 1 0 28 35 1 0 35 36 1 0 25 37 1 0 37 38 1 0 38 39 2 0 20 40 1 0 11 41 1 0 10 42 1 0 5 43 1 0 4 44 1 0 3 45 1 0 7 2 1 0 16 9 1 0 39 18 1 0 38 21 1 0 31 26 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 1 3 50 1 1 4 51 1 1 5 52 1 1 6 53 1 1 9 54 1 1 10 55 1 6 11 56 1 1 12 57 1 6 13 58 1 0 13 59 1 0 14 60 1 0 16 61 1 6 19 62 1 0 24 63 1 0 27 64 1 0 31 65 1 0 33 66 1 0 33 67 1 0 33 68 1 0 34 69 1 0 36 70 1 0 36 71 1 0 36 72 1 0 39 73 1 0 40 74 1 0 41 75 1 0 42 76 1 0 43 77 1 0 44 78 1 0 45 79 1 0 M END

Standard InCHIKey	AIBMPOJXBGZIPQ-QWNFCSOYSA-N
Standard InCHI	InChI=1S/C29H34O16/c1-10-21(33)24(36)26(38)28(41-10)45-27-25(37)23(35)19(9-30)44-29(27)42-12-6-13(31)20-14(32)8-15(43-16(20)7-12)11-4-17(39-2)22(34)18(5-11)40-3/h4-8,10,19,21,23-31,33-38H,9H2,1-3H3/t10-,19+,21-,23+,24+,25-,26+,27+,28-,29+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1cc(c2c(=O)cc(c3cc(c(c(c3)OC)O)OC)oc2c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.18	Volume:	586.91 ? Van der Waals volume.
Dense:	1.087	LogP:	-0.392 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.628 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.896 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	247.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.752	Fsp³:	0.483
MCE-18:	121.279 ? 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:	0.607	Fluc inhibitor:	0.141 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.942 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.596 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.126	Promiscuous compounds:	0.425

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.245	MDCK Permeability:	-5.393
Pgp-inhibitor:	0.001	Pgp-substrate:	0.795
PAMPA:	0.986 ? 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):	0.972
20% Bioavailability (F20%):	0.145	30% Bioavailability (F30%):	0.98
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.524
Plasma Protein Binding (PPB):	81.443%	Volume Distribution (VD):	-0.155
Fu:	16.373% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.955
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.006
HLM stability:	0.04 ? 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):

1.689

Half-life (T1/2):

3.996

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.112
Human Hepatotoxicity (H-HT):	0.523	Drug-induced Liver Injury (DILI):	0.976
AMES Toxicity:	0.868	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.009	Skin Sensitization:	0.997
Carcinogencity:	0.112	Eye Corrosion:	0.0
Eye Irritation:	0.236	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.954
Hematotoxicity:	0.189	Drug-induced Nephrotoxicity:	0.555
Genotoxicity:	0.398	RPMI-8226 Immunitoxicity:	0.245
A549 Cytotoxicity:	0.348	Hek293 Cytotoxicity:	0.321
BCF:	0.38 ? 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:	3.073 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.6 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.7 ? 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
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11356-018-3422-z]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO2413	Saccharum officinarum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17019935]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO2413	Saccharum officinarum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21381697]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO2413	Saccharum officinarum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38397470]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO2413	Saccharum officinarum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2413	Saccharum officinarum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2413	Saccharum officinarum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2413	Saccharum officinarum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2413	Saccharum officinarum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2413	Saccharum officinarum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	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 NPC180664 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	21551
0.1-0.2	23835
0.2-0.3	3627
0.3-0.4	546
0.4-0.5	213
0.5-0.6	53
0.6-0.7	23
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8605	High Similarity	NPC195257
0.8118	Intermediate Similarity	NPC65003
0.8023	Intermediate Similarity	NPC115674
0.7356	Intermediate Similarity	NPC8856
0.7143	Intermediate Similarity	NPC311850
0.703	Intermediate Similarity	NPC198199
0.7021	Intermediate Similarity	NPC475382
0.6765	Remote Similarity	NPC68592
0.6705	Remote Similarity	NPC80188
0.6667	Remote Similarity	NPC120952
0.6596	Remote Similarity	NPC240306
0.6566	Remote Similarity	NPC11468
0.6381	Remote Similarity	NPC298666
0.6373	Remote Similarity	NPC473644
0.6364	Remote Similarity	NPC253685
0.6289	Remote Similarity	NPC32641
0.6289	Remote Similarity	NPC256188
0.6264	Remote Similarity	NPC311830
0.625	Remote Similarity	NPC95090
0.625	Remote Similarity	NPC27408
0.625	Remote Similarity	NPC488083
0.6239	Remote Similarity	NPC262222
0.6237	Remote Similarity	NPC239549
0.6154	Remote Similarity	NPC22832
0.6154	Remote Similarity	NPC243930
0.6146	Remote Similarity	NPC122809
0.6122	Remote Similarity	NPC35119
0.6042	Remote Similarity	NPC22062
0.6042	Remote Similarity	NPC473634
0.6042	Remote Similarity	NPC138811
0.5978	Remote Similarity	NPC601144
0.596	Remote Similarity	NPC209296
0.5914	Remote Similarity	NPC607707
0.5843	Remote Similarity	NPC473043
0.5843	Remote Similarity	NPC331652
0.5842	Remote Similarity	NPC220173
0.5833	Remote Similarity	NPC488086
0.5778	Remote Similarity	NPC261866
0.5778	Remote Similarity	NPC39360
0.5778	Remote Similarity	NPC19709
0.5778	Remote Similarity	NPC29763
0.5778	Remote Similarity	NPC210003
0.5714	Remote Similarity	NPC473072
0.5714	Remote Similarity	NPC189142
0.5714	Remote Similarity	NPC77660
0.5696	Remote Similarity	NPC48479
0.5657	Remote Similarity	NPC257566
0.5648	Remote Similarity	NPC488087
0.5612	Remote Similarity	NPC44931
0.5591	Remote Similarity	NPC222936
0.5567	Remote Similarity	NPC606546
0.5565	Remote Similarity	NPC35924
0.5556	Remote Similarity	NPC210073
0.55	Remote Similarity	NPC470444
0.5484	Remote Similarity	NPC181712
0.5472	Remote Similarity	NPC25724
0.5463	Remote Similarity	NPC480441
0.5463	Remote Similarity	NPC25523
0.5455	Remote Similarity	NPC163242
0.5455	Remote Similarity	NPC272068
0.5437	Remote Similarity	NPC142142
0.54	Remote Similarity	NPC155877
0.5377	Remote Similarity	NPC14187
0.5345	Remote Similarity	NPC199172
0.5288	Remote Similarity	NPC479766
0.5283	Remote Similarity	NPC135358
0.5258	Remote Similarity	NPC220169
0.5238	Remote Similarity	NPC473071
0.5225	Remote Similarity	NPC255799
0.5146	Remote Similarity	NPC46202
0.5146	Remote Similarity	NPC606547
0.5106	Remote Similarity	NPC58053
0.5104	Remote Similarity	NPC27942
0.5102	Remote Similarity	NPC136761
0.51	Remote Similarity	NPC473682
0.51	Remote Similarity	NPC251417
0.5086	Remote Similarity	NPC209550
0.5052	Remote Similarity	NPC611303
0.5051	Remote Similarity	NPC601586
0.5048	Remote Similarity	NPC482026
0.5048	Remote Similarity	NPC473623
0.5044	Remote Similarity	NPC488088
0.5043	Remote Similarity	NPC175429

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC180664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5396
0.1-0.2	3674
0.2-0.3	69
0.3-0.4	6
0.4-0.5	4
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
0.596	Remote Similarity	NPD7054	Phase 4

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