NPASS Compound

Natural Product: NPC166993

Natural Product ID	NPC166993
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Weisiensin A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL486058
PubChem CID	14355978
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

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 71 74 0 0 0 0 0 0 0 0999 V2000 -3.0577 3.3180 -2.5183 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1340 3.0138 -1.4058 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2973 3.9108 -1.1023 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1170 1.8567 -0.6939 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1803 1.5989 0.4038 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0793 1.6651 1.6211 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8391 0.3759 1.8289 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7856 -0.7002 1.9890 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -0.8847 0.6008 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4866 0.3342 0.1731 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9700 0.1439 0.3633 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3432 -0.2790 1.7810 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8703 1.3098 0.1155 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8597 2.0949 1.3293 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7215 3.4373 1.4207 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5941 4.0759 0.3350 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7155 4.1691 2.7397 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3474 0.9455 0.0092 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7064 -0.3907 -0.4675 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5890 -0.9591 -1.2834 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2791 -0.9768 -0.6257 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7945 -2.2562 -0.0634 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6331 -2.1926 0.3773 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4768 -2.9756 -0.4809 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1471 -4.1039 -0.1113 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0171 -4.5005 1.0955 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0131 -4.8978 -1.0129 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5787 -2.9219 0.8333 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5703 -0.0586 -2.5435 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9631 -2.3306 -1.8371 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7934 -0.2493 -1.3768 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5523 -0.7942 -0.1747 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7151 -1.3393 -1.2874 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5097 -0.0077 0.5713 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7524 0.3190 0.2170 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0536 3.5310 -2.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7138 4.1166 -3.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2233 2.3531 -3.0817 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6029 2.5251 0.4279 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4859 1.8302 2.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8187 2.4785 1.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5481 0.4208 2.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2484 -1.6571 2.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1102 -0.3218 2.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5592 0.2335 -0.9991 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0512 0.5606 2.4376 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9080 -1.1834 2.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4609 -0.2776 1.8347 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5830 1.9861 -0.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6821 3.3879 3.5255 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7297 4.6393 2.8353 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8962 4.8901 2.8033 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8563 1.1031 0.9866 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7964 1.7533 -0.6444 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1167 -1.0813 0.2958 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5680 -0.8269 -1.5153 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8005 -2.9658 -0.9634 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7017 -2.7617 1.3583 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4002 -5.7881 -1.3285 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9576 -5.2101 -0.5334 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2144 -4.2621 -1.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4544 -2.6159 1.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1261 -0.4861 -3.3756 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 0.0742 -2.8724 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9594 0.9369 -2.3419 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3659 -3.0266 -1.1201 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8056 -2.1301 -2.5668 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1394 -2.7065 -2.4739 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6461 -0.1564 -0.8963 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3440 0.9075 0.8732 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1237 -0.0205 -0.7215 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 13 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 1 0 25 26 2 0 25 27 1 0 22 28 1 0 20 29 1 0 20 30 1 0 19 31 1 0 9 32 1 6 32 33 2 0 32 34 1 0 34 35 2 0 10 5 1 0 21 11 1 0 34 7 1 0 23 9 1 0 1 36 1 0 1 37 1 0 1 38 1 0 5 39 1 1 6 40 1 0 6 41 1 0 7 42 1 1 8 43 1 0 8 44 1 0 10 45 1 6 12 46 1 0 12 47 1 0 12 48 1 0 13 49 1 6 17 50 1 0 17 51 1 0 17 52 1 0 18 53 1 0 18 54 1 0 19 55 1 1 21 56 1 6 22 57 1 6 23 58 1 1 27 59 1 0 27 60 1 0 27 61 1 0 28 62 1 0 29 63 1 0 29 64 1 0 29 65 1 0 30 66 1 0 30 67 1 0 30 68 1 0 31 69 1 0 35 70 1 0 35 71 1 0 M END

Standard InCHIKey	QTLPNFQMZWBMDF-LYVLPCRDSA-N
Standard InCHI	InChI=1S/C26H36O9/c1-11-15-8-16(33-12(2)27)20-25(7)18(34-13(3)28)9-17(30)24(5,6)21(25)19(31)23(35-14(4)29)26(20,10-15)22(11)32/h15-21,23,30-31H,1,8-10H2,2-7H3/t15-,16+,17+,18+,19-,20+,21-,23+,25+,26+/m1/s1
SMILES	CC(=O)O[C@H]1C[C@@H]2C[C@]3([C@@H]1[C@]1(C)[C@@H](OC(=O)C)C[C@@H](C([C@H]1[C@H]([C@@H]3OC(=O)C)O)(C)C)O)C(=O)C2=C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	492.24	Volume:	489.956 ? Van der Waals volume.
Dense:	1.005	LogP:	1.643 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.923 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.418 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	136.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.343	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.286	Fsp³:	0.769
MCE-18:	122.696 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.728	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.312	Promiscuous compounds:	0.238

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.229	MDCK Permeability:	-4.885
Pgp-inhibitor:	0.992	Pgp-substrate:	0.932
PAMPA:	0.797 ? 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):	0.23
20% Bioavailability (F20%):	0.925	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.954
Plasma Protein Binding (PPB):	62.407%	Volume Distribution (VD):	-0.298
Fu:	34.004% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.245
BSEP inhibitor:	0.787

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.19
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.602	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.967 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.407

Half-life (T1/2):

1.498

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.148
Human Hepatotoxicity (H-HT):	0.549	Drug-induced Liver Injury (DILI):	0.703
AMES Toxicity:	0.653	Rat Oral Acute Toxicity:	0.51
Maximum Recommended Daily Dose:	0.524	Skin Sensitization:	0.983
Carcinogencity:	0.562	Eye Corrosion:	0.001
Eye Irritation:	0.117	Respiratory Toxicity:	0.528
Drug-induced Neurotoxicity:	0.096	Ototoxicity:	0.567
Hematotoxicity:	0.623	Drug-induced Nephrotoxicity:	0.657
Genotoxicity:	0.963	RPMI-8226 Immunitoxicity:	0.103
A549 Cytotoxicity:	0.192	Hek293 Cytotoxicity:	0.225
BCF:	0.467 ? 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:	3.379 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.302 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.529 ? 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
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94333-4]
NPO40865	Isodon adenantha	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193013]
NPO15395	Euphorbia portlandica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792416]
NPO3902	Aglaia edulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190457]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	Heartwood	India	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[21784631]
NPO10205	Aspergillus puniceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31095389]
NPO18360	Isodon weisiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12204	Sideritis marmorea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11468	Senecio fuchsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7357	Polypodium fauriei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3902	Aglaia edulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7074	Didymeles madagascariensis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6120	Attalea funifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1531	Chlorella sorokiniana	Species	Chlorellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5138	Colebrookea oppositifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4800	Cyrtocymura cincta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15395	Euphorbia portlandica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6287	Cora pavonia	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO265	Helminthosporium zizaniae	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12452	Artemisia viridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8191	Lecanora epanora	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10205	Aspergillus puniceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11368	Leontodon tuberosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7594	Muricea californica	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8694	Picrasma crenata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4558	Polysaccum crassipes	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21411	Santolina magonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO688	Scorzonera cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3038	Veronica linariifolia	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40865	Isodon adenantha	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6720	Rabdosia adenantha	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11963	Rhamnus disperma	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1618	Ovidia pillo-pillo	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15395	Euphorbia portlandica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8694	Picrasma crenata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18360	Isodon weisiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3902	Aglaia edulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15395	Euphorbia portlandica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6720	Rabdosia adenantha	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8694	Picrasma crenata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5138	Colebrookea oppositifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11963	Rhamnus disperma	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6287	Cora pavonia	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12452	Artemisia viridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10205	Aspergillus puniceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4558	Polysaccum crassipes	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11468	Senecio fuchsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3902	Aglaia edulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7074	Didymeles madagascariensis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15395	Euphorbia portlandica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4800	Cyrtocymura cincta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7594	Muricea californica	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3038	Veronica linariifolia	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11368	Leontodon tuberosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7357	Polypodium fauriei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO688	Scorzonera cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21411	Santolina magonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6720	Rabdosia adenantha	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1531	Chlorella sorokiniana	Species	Chlorellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO265	Helminthosporium zizaniae	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8191	Lecanora epanora	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8694	Picrasma crenata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12204	Sideritis marmorea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6120	Attalea funifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18360	Isodon weisiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1618	Ovidia pillo-pillo	Species	Thymelaeaceae	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

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell line	4

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
NPT111	Cell line	K562	Homo sapiens	IC50	=	4110.0	nM	PMID[18345641]
NPT81	Cell line	A549	Homo sapiens	IC50	=	1880.0	nM	PMID[18345641]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	1430.0	nM	PMID[18345641]
NPT111	Cell line	K562	Homo sapiens	IC50	=	3.3	ug.mL-1	PMID[12193013]

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 NPC166993 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	20295
0.1-0.2	26349
0.2-0.3	3056
0.3-0.4	110
0.4-0.5	31
0.5-0.6	8
0.6-0.7	4
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
0.7288	Intermediate Similarity	NPC275990
0.6825	Remote Similarity	NPC138908
0.6825	Remote Similarity	NPC176949
0.6667	Remote Similarity	NPC274793
0.6667	Remote Similarity	NPC292718
0.5672	Remote Similarity	NPC295366
0.5522	Remote Similarity	NPC200957
0.5373	Remote Similarity	NPC201908
0.5303	Remote Similarity	NPC111834
0.5294	Remote Similarity	NPC20479
0.5224	Remote Similarity	NPC28864
0.5152	Remote Similarity	NPC194485
0.5075	Remote Similarity	NPC46848

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC166993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6653
0.1-0.2	2470
0.2-0.3	27
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
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
		NPD

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