NPASS Compound

Natural Product: NPC116698

Natural Product ID	NPC116698
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SHEMZXKUXGNYPP-KFQZITOESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID: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 3D 75 79 0 0 0 0 0 0 0 0999 V2000 -6.1115 -2.2149 3.5107 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3085 -1.8493 2.3098 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9963 -2.2470 1.0255 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5277 -1.0007 0.3463 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3218 -0.1249 0.0370 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3730 -0.0528 1.1828 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0587 1.2757 1.4401 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 1.5633 1.5920 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9548 1.3066 0.3577 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3525 2.3776 -0.6705 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1152 2.6160 -1.5279 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4566 1.2792 -1.7587 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0656 0.7524 -0.4410 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5641 1.5368 0.5930 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3487 0.5787 -0.2572 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5960 0.3842 -0.0680 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1051 0.8086 1.1965 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3140 1.3356 2.0482 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4207 0.6617 1.5130 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9391 1.0709 2.7449 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2708 0.9191 3.0588 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1408 0.3515 2.1528 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6270 -0.0511 0.9376 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2782 0.0966 0.6065 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7975 -0.2783 -0.5239 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5206 -0.1735 -0.9170 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2240 -0.6747 -2.2570 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0024 -1.0083 -2.7509 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8150 -1.4082 -4.0770 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8600 -1.4883 -4.9609 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1057 -1.1530 -4.4700 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2820 -0.7592 -3.1602 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6649 -1.8863 -6.2767 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4869 0.2017 2.4784 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3718 -0.3858 1.5464 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0123 1.6425 3.6300 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4592 0.4449 -2.2834 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3182 3.5035 -0.8114 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3899 1.9737 -1.4581 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9977 -0.4985 2.3763 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6693 -0.7761 -1.0317 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3725 -0.2870 1.1647 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1514 -2.9316 0.1778 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4293 -2.7095 4.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4953 -1.3026 4.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9220 -2.9506 3.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3380 -2.4054 2.3353 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8794 -2.8571 1.3135 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0770 -1.3140 -0.5637 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6015 0.8776 -0.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4719 -0.6695 1.0920 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6832 2.6810 1.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2842 1.1205 2.5078 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0537 0.2966 0.0025 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5675 3.3019 -0.0814 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3874 3.1188 -2.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3285 1.3320 -2.5430 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4799 -0.2444 -0.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6416 1.2492 4.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2702 -0.4930 0.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1632 -1.0032 -2.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8235 -1.6645 -4.4251 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9330 -1.2137 -5.1642 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2808 -0.4974 -2.7974 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3716 -2.7831 -6.5814 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1125 -1.4716 1.3976 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4311 -0.2619 1.8394 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2630 0.0629 0.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8446 1.1679 4.5013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4386 0.3928 -3.2511 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8202 4.1917 -0.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9110 2.7926 -1.7412 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9714 -0.3986 -1.8992 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1142 -0.8475 1.5466 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5484 -2.9289 -0.7417 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 34 35 1 0 20 36 1 0 12 37 1 0 11 38 1 0 10 39 1 0 6 40 1 0 5 41 1 0 4 42 1 0 3 43 1 0 40 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 24 19 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 1 3 48 1 1 4 49 1 6 5 50 1 6 6 51 1 6 8 52 1 0 8 53 1 0 9 54 1 6 10 55 1 1 11 56 1 6 12 57 1 6 13 58 1 1 21 59 1 0 23 60 1 0 28 61 1 0 29 62 1 0 31 63 1 0 32 64 1 0 33 65 1 0 35 66 1 0 35 67 1 0 35 68 1 0 36 69 1 0 37 70 1 0 38 71 1 0 39 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 M END

Standard InCHIKey	SHEMZXKUXGNYPP-KFQZITOESA-N
Standard InCHI	InChI=1S/C28H32O15/c1-10-18(31)21(34)23(36)27(40-10)39-9-16-19(32)22(35)24(37)28(42-16)43-26-20(33)17-14(30)7-13(38-2)8-15(17)41-25(26)11-3-5-12(29)6-4-11/h3-8,10,16,18-19,21-24,27-32,34-37H,9H2,1-2H3/t10-,16-,18-,19-,21+,22+,23-,24-,27-,28+/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)OC)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	0.909 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.465 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.453 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.649	Fsp³:	0.464
MCE-18:	118.585 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.622	Fluc inhibitor:	0.27 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.844 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.72 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.063	Promiscuous compounds:	0.406

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.427	MDCK Permeability:	-5.204
Pgp-inhibitor:	0.0	Pgp-substrate:	0.687
PAMPA:	0.999 ? 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):	0.423
20% Bioavailability (F20%):	0.027	30% Bioavailability (F30%):	0.894
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.003
Plasma Protein Binding (PPB):	85.371%	Volume Distribution (VD):	-0.007
Fu:	14.304% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.73
BSEP inhibitor:	0.296

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:	0.012
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.989
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.79 ? 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):

1.127

Half-life (T1/2):

3.971

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.207
Human Hepatotoxicity (H-HT):	0.45	Drug-induced Liver Injury (DILI):	0.967
AMES Toxicity:	0.699	Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.057	Skin Sensitization:	0.956
Carcinogencity:	0.064	Eye Corrosion:	0.0
Eye Irritation:	0.729	Respiratory Toxicity:	0.021
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.781
Hematotoxicity:	0.067	Drug-induced Nephrotoxicity:	0.543
Genotoxicity:	0.487	RPMI-8226 Immunitoxicity:	0.176
A549 Cytotoxicity:	0.415	Hek293 Cytotoxicity:	0.375
BCF:	0.689 ? 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:	3.411 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.879 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.081 ? 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
NPO25128	Panax vietnamensis	Species	Araliaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[11325227]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO22637	Kunzea ambigua	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043420]
NPO10407	Petromyzon marinus	Species	Petromyzontidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15193266]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25557	Alternaria porri	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16885	Phonus arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25321	Acantholimon glumaceum	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5676	Annulohypoxylon multiforme	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28771	Clematis delavayi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24735	Cupania latifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24591	Trichosanthes dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19721	Impatiens roylei	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8943	Juniperus californica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22637	Kunzea ambigua	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17249	Lespedeza capitata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25410	Manilkara bidentata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24821	Nidorella resedifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25128	Panax vietnamensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10407	Petromyzon marinus	Species	Petromyzontidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24549	Scutellaria cordifrons	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24866	Smilax aspera	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23489	Stachys anisochila	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25468	Tabernaemontana amygdalifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16885	Phonus arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28771	Clematis delavayi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24821	Nidorella resedifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25128	Panax vietnamensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24591	Trichosanthes dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17249	Lespedeza capitata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10407	Petromyzon marinus	Species	Petromyzontidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24866	Smilax aspera	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24549	Scutellaria cordifrons	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24735	Cupania latifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25468	Tabernaemontana amygdalifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19721	Impatiens roylei	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23489	Stachys anisochila	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22637	Kunzea ambigua	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8943	Juniperus californica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25321	Acantholimon glumaceum	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25557	Alternaria porri	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25410	Manilkara bidentata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5676	Annulohypoxylon multiforme	Species	Xylariaceae	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 NPC116698 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	19391
0.1-0.2	26284
0.2-0.3	3122
0.3-0.4	514
0.4-0.5	272
0.5-0.6	104
0.6-0.7	55
0.7-0.8	2
0.8-0.85	8
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC186816
0.8333	Intermediate Similarity	NPC46420
0.8161	Intermediate Similarity	NPC142142
0.8095	Intermediate Similarity	NPC173582
0.8095	Intermediate Similarity	NPC265885
0.8095	Intermediate Similarity	NPC181465
0.8095	Intermediate Similarity	NPC215710
0.8095	Intermediate Similarity	NPC473438
0.8095	Intermediate Similarity	NPC253788
0.7907	Intermediate Similarity	NPC473571
0.7907	Intermediate Similarity	NPC110941
0.7848	Intermediate Similarity	NPC249281
0.7674	Intermediate Similarity	NPC44931
0.766	Intermediate Similarity	NPC25523
0.7619	Intermediate Similarity	NPC276377
0.7586	Intermediate Similarity	NPC65563
0.7586	Intermediate Similarity	NPC470949
0.7528	Intermediate Similarity	NPC470443
0.7439	Intermediate Similarity	NPC271692
0.7386	Intermediate Similarity	NPC203259
0.7386	Intermediate Similarity	NPC33054
0.7386	Intermediate Similarity	NPC176740
0.7386	Intermediate Similarity	NPC471725
0.7386	Intermediate Similarity	NPC134532
0.7386	Intermediate Similarity	NPC602582
0.7294	Intermediate Similarity	NPC116458
0.7294	Intermediate Similarity	NPC246943
0.7283	Intermediate Similarity	NPC476472
0.7283	Intermediate Similarity	NPC294815
0.7283	Intermediate Similarity	NPC16194
0.7273	Intermediate Similarity	NPC67105
0.7222	Intermediate Similarity	NPC126784
0.7222	Intermediate Similarity	NPC241423
0.7191	Intermediate Similarity	NPC210073
0.7191	Intermediate Similarity	NPC150164
0.7158	Intermediate Similarity	NPC121703
0.7065	Intermediate Similarity	NPC473327
0.7033	Intermediate Similarity	NPC240306
0.7	Intermediate Similarity	NPC22062
0.7	Intermediate Similarity	NPC473634
0.7	Intermediate Similarity	NPC138811
0.6966	Remote Similarity	NPC471079
0.6939	Remote Similarity	NPC480441
0.6915	Remote Similarity	NPC473073
0.6905	Remote Similarity	NPC297987
0.6905	Remote Similarity	NPC158674
0.6889	Remote Similarity	NPC39834
0.6882	Remote Similarity	NPC32641
0.6882	Remote Similarity	NPC256188
0.6882	Remote Similarity	NPC209296
0.6882	Remote Similarity	NPC72016
0.6703	Remote Similarity	NPC227508
0.6702	Remote Similarity	NPC35119
0.6667	Remote Similarity	NPC611303
0.663	Remote Similarity	NPC303913
0.6596	Remote Similarity	NPC12013
0.6596	Remote Similarity	NPC11432
0.6596	Remote Similarity	NPC477613
0.6571	Remote Similarity	NPC209550
0.6566	Remote Similarity	NPC189564
0.6517	Remote Similarity	NPC605784
0.6495	Remote Similarity	NPC470449
0.6471	Remote Similarity	NPC111929
0.6471	Remote Similarity	NPC320283
0.6471	Remote Similarity	NPC41121
0.6465	Remote Similarity	NPC203145
0.6458	Remote Similarity	NPC486577
0.6452	Remote Similarity	NPC156869
0.6392	Remote Similarity	NPC470447
0.6344	Remote Similarity	NPC67326
0.6327	Remote Similarity	NPC101636
0.6327	Remote Similarity	NPC221342
0.6327	Remote Similarity	NPC476470
0.6316	Remote Similarity	NPC488073
0.6316	Remote Similarity	NPC488074
0.6263	Remote Similarity	NPC602448
0.6214	Remote Similarity	NPC277532
0.6207	Remote Similarity	NPC108831
0.6207	Remote Similarity	NPC182634
0.62	Remote Similarity	NPC14187
0.6146	Remote Similarity	NPC64425
0.6136	Remote Similarity	NPC136042
0.6111	Remote Similarity	NPC138990
0.6092	Remote Similarity	NPC331652
0.6067	Remote Similarity	NPC84362
0.6067	Remote Similarity	NPC27640
0.6055	Remote Similarity	NPC175429
0.6042	Remote Similarity	NPC204693
0.604	Remote Similarity	NPC470455
0.6023	Remote Similarity	NPC289667
0.6022	Remote Similarity	NPC116864
0.6022	Remote Similarity	NPC244776
0.602	Remote Similarity	NPC122467
0.602	Remote Similarity	NPC606657
0.6019	Remote Similarity	NPC292019
0.6019	Remote Similarity	NPC202908
0.598	Remote Similarity	NPC89052
0.5979	Remote Similarity	NPC153755
0.5957	Remote Similarity	NPC251417
0.5941	Remote Similarity	NPC470446
0.59	Remote Similarity	NPC89127
0.5895	Remote Similarity	NPC187379
0.5889	Remote Similarity	NPC24043
0.5876	Remote Similarity	NPC129264
0.5865	Remote Similarity	NPC173837
0.5859	Remote Similarity	NPC473623
0.5843	Remote Similarity	NPC127546
0.5843	Remote Similarity	NPC57625
0.5843	Remote Similarity	NPC173637
0.5843	Remote Similarity	NPC317489
0.5843	Remote Similarity	NPC238376
0.5843	Remote Similarity	NPC223424
0.5843	Remote Similarity	NPC600591
0.5842	Remote Similarity	NPC298171
0.5842	Remote Similarity	NPC470445
0.5833	Remote Similarity	NPC275454
0.5824	Remote Similarity	NPC59534
0.5816	Remote Similarity	NPC470125
0.5816	Remote Similarity	NPC64051
0.5806	Remote Similarity	NPC223747
0.58	Remote Similarity	NPC488089
0.5789	Remote Similarity	NPC483159
0.5789	Remote Similarity	NPC483160
0.5784	Remote Similarity	NPC470450
0.5784	Remote Similarity	NPC135358
0.5773	Remote Similarity	NPC473512
0.5773	Remote Similarity	NPC479405
0.5773	Remote Similarity	NPC129827
0.5769	Remote Similarity	NPC146679
0.5758	Remote Similarity	NPC65711
0.5745	Remote Similarity	NPC476215
0.5743	Remote Similarity	NPC85751
0.5743	Remote Similarity	NPC19240
0.5729	Remote Similarity	NPC609888
0.5714	Remote Similarity	NPC305811
0.5714	Remote Similarity	NPC479404
0.57	Remote Similarity	NPC270448
0.5686	Remote Similarity	NPC36138
0.5684	Remote Similarity	NPC265115
0.5673	Remote Similarity	NPC11468
0.5667	Remote Similarity	NPC77672
0.5667	Remote Similarity	NPC133671
0.5667	Remote Similarity	NPC19709
0.5667	Remote Similarity	NPC135391
0.5667	Remote Similarity	NPC78263
0.5667	Remote Similarity	NPC250069
0.5652	Remote Similarity	NPC473554
0.5636	Remote Similarity	NPC474522
0.5604	Remote Similarity	NPC265530
0.5591	Remote Similarity	NPC219904
0.5577	Remote Similarity	NPC214621
0.5577	Remote Similarity	NPC34267
0.5545	Remote Similarity	NPC298666
0.5543	Remote Similarity	NPC488080
0.5543	Remote Similarity	NPC169977
0.5536	Remote Similarity	NPC241781
0.5534	Remote Similarity	NPC292929
0.5521	Remote Similarity	NPC172807
0.5514	Remote Similarity	NPC303694
0.551	Remote Similarity	NPC163242
0.551	Remote Similarity	NPC272068
0.55	Remote Similarity	NPC475366
0.549	Remote Similarity	NPC270675
0.549	Remote Similarity	NPC195685
0.5487	Remote Similarity	NPC192539
0.5484	Remote Similarity	NPC27942
0.5474	Remote Similarity	NPC99957
0.5472	Remote Similarity	NPC470416
0.5455	Remote Similarity	NPC605592
0.5446	Remote Similarity	NPC483414
0.5446	Remote Similarity	NPC479403
0.5446	Remote Similarity	NPC470720
0.5446	Remote Similarity	NPC483415
0.5437	Remote Similarity	NPC80068
0.5437	Remote Similarity	NPC471669
0.5435	Remote Similarity	NPC323593
0.5435	Remote Similarity	NPC203500
0.5421	Remote Similarity	NPC480796
0.5421	Remote Similarity	NPC472993
0.5417	Remote Similarity	NPC66087
0.5408	Remote Similarity	NPC480466
0.5408	Remote Similarity	NPC139320
0.5405	Remote Similarity	NPC480445
0.54	Remote Similarity	NPC470444
0.5393	Remote Similarity	NPC54802
0.5393	Remote Similarity	NPC197304
0.5392	Remote Similarity	NPC483416
0.5392	Remote Similarity	NPC229409
0.5385	Remote Similarity	NPC135599
0.5385	Remote Similarity	NPC73855
0.5385	Remote Similarity	NPC113968
0.5385	Remote Similarity	NPC328940
0.5385	Remote Similarity	NPC277174
0.5385	Remote Similarity	NPC606877
0.5376	Remote Similarity	NPC349108
0.537	Remote Similarity	NPC473644
0.537	Remote Similarity	NPC217520
0.537	Remote Similarity	NPC164704
0.5357	Remote Similarity	NPC156785
0.5357	Remote Similarity	NPC162394

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC116698 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5178
0.1-0.2	3908
0.2-0.3	56
0.3-0.4	1
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8068	Intermediate Similarity	NPD7251	Phase 2
0.7386	Intermediate Similarity	NPD6797	Phase 2
0.734	Intermediate Similarity	NPD7808	Phase 3
0.6882	Remote Similarity	NPD7054	Phase 4
0.5524	Remote Similarity	NPD7472	Pre-clinical

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