NPASS Compound

Natural Product: NPC165991

Natural Product ID	NPC165991
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SJFTVAAHLRFBST-NSHQGHFVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	126843388
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003534] Flavonoid-7-O-glucuronides

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 70 74 0 0 0 0 0 0 0 0999 V2000 7.4877 1.5547 0.3333 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1910 2.6647 -0.1166 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5436 3.6286 -0.8223 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2099 3.4898 -1.0782 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5177 2.3860 -0.6290 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1528 1.3874 0.0933 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3857 0.2373 0.5495 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9870 -0.7678 1.2665 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2528 -1.8719 1.7050 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7981 -2.8032 2.3663 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9110 -1.8798 1.3736 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1503 -2.9616 1.7929 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8165 -2.9644 1.4605 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2002 -1.9563 0.7382 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9843 -0.9006 0.3394 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3485 -0.8490 0.6518 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0839 0.1593 0.2676 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1365 -2.0780 0.4721 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9467 -1.1777 -0.2376 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1805 -0.7838 0.5948 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6096 -2.1126 1.2181 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8646 -3.1349 0.1817 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0992 -3.0234 -1.0809 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1421 -4.1486 -1.2467 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0484 -3.9216 -1.5764 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5757 -5.4334 -1.0352 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4647 -1.8569 -1.3335 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2617 -3.1770 -0.0379 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6132 -2.5568 2.1041 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1568 -0.4246 -0.3008 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6754 0.8415 -0.1070 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1906 0.7441 0.1134 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6641 2.1586 0.3699 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4484 2.9141 -0.9429 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9496 2.8453 -1.2223 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7356 3.4938 -2.5361 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2191 2.8682 -3.4921 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1020 4.8132 -2.7429 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5030 1.5514 -1.2885 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8501 4.2299 -0.8409 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9888 2.2083 0.7692 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4946 -0.1138 1.1589 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7540 -3.9662 2.5101 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2445 4.7347 -1.2706 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0474 0.8368 0.8783 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2472 2.7796 0.0832 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6632 4.2393 -1.6378 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4492 2.2729 -0.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0400 -0.7230 1.5048 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2506 -3.8365 1.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5544 -0.0957 -0.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4217 -0.2976 -0.6062 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9336 -0.0349 1.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4982 -1.9025 1.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6344 -4.1434 0.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8434 -3.1716 -1.9238 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9864 -6.2560 -1.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4688 -3.2972 -0.9865 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5131 -1.8925 2.8353 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1828 1.3091 0.7489 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6470 0.4209 -0.8418 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9839 2.6528 1.1049 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0429 2.4008 -1.7021 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4544 3.4493 -0.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5378 5.4080 -3.3524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6031 4.3591 -0.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1967 1.3046 1.1606 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4649 0.4298 1.9883 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9286 -4.8994 2.1277 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0372 4.6405 -1.8781 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 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 23 27 1 0 22 28 1 0 21 29 1 0 20 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 35 39 1 0 34 40 1 0 33 41 1 0 32 42 1 0 12 43 1 0 3 44 1 0 6 1 1 0 17 7 1 0 27 19 1 0 39 31 1 0 16 11 1 0 1 45 1 0 2 46 1 0 4 47 1 0 5 48 1 0 8 49 1 0 13 50 1 0 15 51 1 0 19 52 1 6 20 53 1 1 21 54 1 1 22 55 1 1 23 56 1 6 26 57 1 0 28 58 1 0 29 59 1 0 31 60 1 1 32 61 1 6 33 62 1 1 34 63 1 6 35 64 1 1 38 65 1 0 40 66 1 0 41 67 1 0 42 68 1 0 43 69 1 0 44 70 1 0 M END

Standard InCHIKey	SJFTVAAHLRFBST-NSHQGHFVSA-N
Standard InCHI	InChI=1S/C27H26O17/c28-9-3-1-8(2-4-9)13-7-12(30)15-11(29)5-10(6-14(15)41-13)40-27-23(19(34)18(33)22(43-27)25(38)39)44-26-20(35)16(31)17(32)21(42-26)24(36)37/h1-7,16-23,26-29,31-35H,(H,36,37)(H,38,39)/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27+/m1/s1
SMILES	c1cc(ccc1c1cc(=O)c2c(cc(cc2o1)O[C@@H]1[C@H]([C@@H]([C@H]([C@H](C(=O)O)O1)O)O)O[C@@H]1[C@H]([C@@H]([C@H]([C@H](C(=O)O)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	622.12	Volume:	555.835 ? Van der Waals volume.
Dense:	1.119	LogP:	0.438 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.92 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.726 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	32.0
TPSA:	283.34 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.138	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.737	Fsp³:	0.37
MCE-18:	123.919 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.48	Fluc inhibitor:	0.37 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.848 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.65 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.438	Promiscuous compounds:	0.423

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.515	MDCK Permeability:	-5.073
Pgp-inhibitor:	0.0	Pgp-substrate:	0.473
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.066
20% Bioavailability (F20%):	0.013	30% Bioavailability (F30%):	0.052
50% Bioavailability (F50%):	0.838

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.994
Plasma Protein Binding (PPB):	74.498%	Volume Distribution (VD):	-0.194
Fu:	21.158% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.008
OATP1B3 inhibitor:	0.449	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.823
HLM stability:	0.004 ? 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):

0.654

Half-life (T1/2):

4.634

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.008
Human Hepatotoxicity (H-HT):	0.283	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.499	Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.03	Skin Sensitization:	0.989
Carcinogencity:	0.015	Eye Corrosion:	0.0
Eye Irritation:	0.488	Respiratory Toxicity:	0.021
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.854
Hematotoxicity:	0.064	Drug-induced Nephrotoxicity:	0.729
Genotoxicity:	0.962	RPMI-8226 Immunitoxicity:	0.059
A549 Cytotoxicity:	0.046	Hek293 Cytotoxicity:	0.139
BCF:	0.163 ? 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:	2.712 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.24 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.359 ? 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
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[1612412]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[18566831]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	roots	n.a.	n.a.	PMID[19128156]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	exudate	n.a.	n.a.	PMID[20028108]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20674349]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428274]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26169681]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13467	Anarsia lineatella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14057	Apollonias barbujana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8892	Sordaria araneosa	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4671	Persea mexicana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5191	Penicillium cinerascens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO746	Panax innovans	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11998	Ledebouria socialis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO205	Lasianthus fordii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12509	Dipterocarpus dyeri	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13766	Ceanothus velutinus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14057	Apollonias barbujana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13766	Ceanothus velutinus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8892	Sordaria araneosa	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4671	Persea mexicana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11998	Ledebouria socialis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO746	Panax innovans	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13467	Anarsia lineatella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12509	Dipterocarpus dyeri	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO205	Lasianthus fordii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5191	Penicillium cinerascens	Species	Aspergillaceae	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 NPC165991 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	23657
0.1-0.2	23643
0.2-0.3	1786
0.3-0.4	543
0.4-0.5	177
0.5-0.6	38
0.6-0.7	10
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	Natural Product ID
0.7826	Intermediate Similarity	NPC253685
0.7619	Intermediate Similarity	NPC282169
0.6818	Remote Similarity	NPC20505
0.6742	Remote Similarity	NPC608742
0.6421	Remote Similarity	NPC65003
0.6122	Remote Similarity	NPC64051
0.6105	Remote Similarity	NPC8856
0.6067	Remote Similarity	NPC331652
0.6022	Remote Similarity	NPC43211
0.6	Remote Similarity	NPC39360
0.6	Remote Similarity	NPC29763
0.6	Remote Similarity	NPC210003
0.5859	Remote Similarity	NPC122809
0.5859	Remote Similarity	NPC115674
0.5816	Remote Similarity	NPC44931
0.5806	Remote Similarity	NPC27942
0.5686	Remote Similarity	NPC229409
0.5676	Remote Similarity	NPC298666
0.5612	Remote Similarity	NPC606546
0.5579	Remote Similarity	NPC210094
0.549	Remote Similarity	NPC46202
0.5484	Remote Similarity	NPC19709
0.5429	Remote Similarity	NPC195257
0.5426	Remote Similarity	NPC189142
0.5426	Remote Similarity	NPC77660
0.537	Remote Similarity	NPC11468
0.5361	Remote Similarity	NPC610187
0.5354	Remote Similarity	NPC600989
0.5333	Remote Similarity	NPC479766
0.5294	Remote Similarity	NPC210073
0.5263	Remote Similarity	NPC95090
0.5263	Remote Similarity	NPC27408
0.5258	Remote Similarity	NPC237435
0.5208	Remote Similarity	NPC181712
0.5204	Remote Similarity	NPC601144
0.5189	Remote Similarity	NPC270675
0.5189	Remote Similarity	NPC195685
0.5181	Remote Similarity	NPC234133
0.5146	Remote Similarity	NPC22062
0.5146	Remote Similarity	NPC473634
0.5146	Remote Similarity	NPC138811
0.5133	Remote Similarity	NPC488087
0.51	Remote Similarity	NPC190003
0.5093	Remote Similarity	NPC101636
0.5089	Remote Similarity	NPC473644
0.5053	Remote Similarity	NPC473043
0.5051	Remote Similarity	NPC80188
0.5046	Remote Similarity	NPC472994
0.5044	Remote Similarity	NPC311850
0.5043	Remote Similarity	NPC68592

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC165991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4757
0.1-0.2	4321
0.2-0.3	61
0.3-0.4	9
0.4-0.5	1
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
0.5258	Remote Similarity	NPD4338	Clinical (unspecified phase)

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