NPASS Compound

Natural Product: NPC14042

Natural Product ID	NPC14042
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HCXVJBMSMIARIN-OSFBXNEZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	124762119
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

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 78 81 0 0 0 0 0 0 0 0999 V2000 4.5059 -1.9086 -1.8495 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6518 -0.9203 -1.8679 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6010 -0.0304 -0.6492 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3166 0.7459 -0.5976 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4335 0.5885 0.3645 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1380 1.3531 0.4412 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1919 2.0993 1.7556 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0572 0.3072 0.4041 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2430 -0.5944 1.5823 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1375 -1.0255 1.9396 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1033 -0.0774 1.3217 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1990 -0.7653 0.5836 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9836 -1.7641 1.4029 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9425 -2.3846 0.4425 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6471 -1.5848 -0.3455 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5964 -2.2421 -1.2974 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6833 -1.3694 -1.7997 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6025 0.0718 -1.4267 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1620 0.5386 -1.4277 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4869 -0.1285 -0.2485 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3212 0.3078 0.9703 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0970 0.2828 -0.0267 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3401 0.7816 -1.2404 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 0.5405 -1.1033 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3335 0.7708 0.3084 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5717 2.2042 0.6478 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9636 -1.8403 -1.4303 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7925 0.9122 -0.6124 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0935 0.1760 -0.5704 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7031 1.7927 0.6109 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3336 -2.1703 -0.7679 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5698 -1.4187 -2.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7284 -2.8441 -2.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 -1.5122 -1.8075 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6495 -0.3638 -2.8187 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6843 -0.6879 0.2397 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0689 1.4763 -1.3661 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6360 -0.1270 1.1516 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1161 2.0112 -0.4442 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3632 3.1859 1.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0483 1.7848 2.4031 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2895 1.9327 2.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3053 -0.3225 -0.5047 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7856 -0.1125 2.4219 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8552 -1.4958 1.3270 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2930 -2.0944 1.6414 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2015 -1.0475 3.0672 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5487 0.5428 2.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7933 -1.3576 -0.2826 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4274 -1.3767 2.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2705 -2.5624 1.7030 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0582 -3.4789 0.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0605 -3.1300 -0.7950 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9625 -2.6620 -2.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6982 -1.4311 -2.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1414 0.6580 -2.2299 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1424 0.2875 -0.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0945 1.6359 -1.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7311 0.2817 -2.3909 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0497 -0.4372 1.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8808 1.2583 0.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6529 0.5993 1.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0970 1.1249 0.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5900 1.8225 -1.4687 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6595 0.1231 -2.1007 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3654 1.3532 -1.7202 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5121 -0.3996 -1.5422 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9675 2.3256 1.6780 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3928 2.6065 -0.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2823 2.8752 0.4232 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6395 -1.1426 -1.5144 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8120 1.5566 -1.5348 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8900 0.7853 -0.0991 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4125 -0.2341 -1.5504 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9538 -0.7167 0.0963 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7517 2.0317 0.9483 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1988 1.2897 1.4394 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2019 2.7395 0.2911 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 2 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 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 17 27 1 0 3 28 1 0 28 29 1 0 28 30 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 2 35 1 0 3 36 1 1 4 37 1 0 5 38 1 0 6 39 1 6 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 6 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 1 12 49 1 6 13 50 1 0 13 51 1 0 14 52 1 0 16 53 1 0 16 54 1 0 17 55 1 6 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 1 23 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	HCXVJBMSMIARIN-OSFBXNEZSA-N
Standard InCHI	InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21+,23-,24+,25+,26+,27+,28-,29+/m0/s1
SMILES	CC[C@H](/C=C/[C@H](C)[C@H]1CC[C@@H]2[C@H]3CC=C4C[C@H](CC[C@]4(C)[C@@H]3CC[C@]12C)O)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.37	Volume:	479.432 ? Van der Waals volume.
Dense:	0.86	LogP:	6.249 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.82 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.652 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.457	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.571	Fsp³:	0.862
MCE-18:	69.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.989	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.621	Promiscuous compounds:	0.023

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.059	MDCK Permeability:	-4.788
Pgp-inhibitor:	0.866	Pgp-substrate:	0.037
PAMPA:	0.006 ? 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):	0.0
20% Bioavailability (F20%):	0.696	30% Bioavailability (F30%):	0.792
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.271
Plasma Protein Binding (PPB):	98.468%	Volume Distribution (VD):	-0.067
Fu:	1.048% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.764
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.011
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.008	CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.745	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.749 ? 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):

13.138

Half-life (T1/2):

0.454

ADMET: Toxicity

hERG Blockers:	0.143	hERG Blockers (10um):	0.299
Human Hepatotoxicity (H-HT):	0.631	Drug-induced Liver Injury (DILI):	0.612
AMES Toxicity:	0.194	Rat Oral Acute Toxicity:	0.2
Maximum Recommended Daily Dose:	0.641	Skin Sensitization:	0.982
Carcinogencity:	0.835	Eye Corrosion:	0.053
Eye Irritation:	0.884	Respiratory Toxicity:	0.902
Drug-induced Neurotoxicity:	0.278	Ototoxicity:	0.587
Hematotoxicity:	0.457	Drug-induced Nephrotoxicity:	0.605
Genotoxicity:	0.116	RPMI-8226 Immunitoxicity:	0.092
A549 Cytotoxicity:	0.396	Hek293 Cytotoxicity:	0.717
BCF:	2.651 ? 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:	4.205 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.942 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.819 ? 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
NPO10700	Filipendula ulmaria	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s10600-006-0064-z]
NPO1528	Dalea elegans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21561780]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO10700	Filipendula ulmaria	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37110746]
NPO10700	Filipendula ulmaria	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39456454]
NPO10700	Filipendula ulmaria	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1412	Artemisia juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9144	Atriplex parvifolia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11000	Eupatorium laevigatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9485	Haplopappus deserticola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19776	Hesperocyparis arizonica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11473	Viburnum lantana	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1785	Corallina rubens	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4471	Blumea densiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6024	Cratoxylum formosum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1528	Dalea elegans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11062	Euonymus grandiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO480	Hygrophila erecta	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8685	Hymenocallis arenicola	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9525	Relicina samoensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4174	Dioscorea deltoidea	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24513	Streptomyces cyaneofuscatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO743	Wardomyces inflatus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11062	Euonymus grandiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4174	Dioscorea deltoidea	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28519	Vachellia luederitzii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10700	Filipendula ulmaria	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8685	Hymenocallis arenicola	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11062	Euonymus grandiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4174	Dioscorea deltoidea	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7314	Rumohra miqueliana	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9485	Haplopappus deserticola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9144	Atriplex parvifolia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4471	Blumea densiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO480	Hygrophila erecta	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24513	Streptomyces cyaneofuscatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9525	Relicina samoensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO743	Wardomyces inflatus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1412	Artemisia juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19776	Hesperocyparis arizonica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11062	Euonymus grandiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11000	Eupatorium laevigatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10700	Filipendula ulmaria	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6024	Cratoxylum formosum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11473	Viburnum lantana	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8685	Hymenocallis arenicola	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1785	Corallina rubens	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1528	Dalea elegans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17450	Calanthe sylvatica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11469	Aspergillus parvathecius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28904	Neonectria fuckeliana	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28977	Tetradesmus obliquus	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28519	Vachellia luederitzii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3522	Stachytarpheta cayennensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4174	Dioscorea deltoidea	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9202	Hololepis pedunculata	Species	Asteraceae	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 NPC14042 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	22782
0.1-0.2	23564
0.2-0.3	3116
0.3-0.4	247
0.4-0.5	80
0.5-0.6	20
0.6-0.7	34
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC113733
0.8571	High Similarity	NPC154330
0.7451	Intermediate Similarity	NPC162742
0.7451	Intermediate Similarity	NPC304309
0.7451	Intermediate Similarity	NPC470228
0.7358	Intermediate Similarity	NPC230301
0.7273	Intermediate Similarity	NPC33913
0.7037	Intermediate Similarity	NPC285893
0.6981	Remote Similarity	NPC22105
0.6981	Remote Similarity	NPC34019
0.6981	Remote Similarity	NPC107059
0.6981	Remote Similarity	NPC600590
0.6909	Remote Similarity	NPC234193
0.6852	Remote Similarity	NPC136188
0.6852	Remote Similarity	NPC28657
0.6852	Remote Similarity	NPC474216
0.6842	Remote Similarity	NPC58063
0.6727	Remote Similarity	NPC198968
0.6727	Remote Similarity	NPC134847
0.6667	Remote Similarity	NPC221758
0.6607	Remote Similarity	NPC241290
0.6607	Remote Similarity	NPC164840
0.6607	Remote Similarity	NPC484739
0.6607	Remote Similarity	NPC209944
0.6607	Remote Similarity	NPC264245
0.6607	Remote Similarity	NPC155986
0.6552	Remote Similarity	NPC603646
0.6491	Remote Similarity	NPC328714
0.6491	Remote Similarity	NPC321381
0.6379	Remote Similarity	NPC472265
0.6379	Remote Similarity	NPC318495
0.6379	Remote Similarity	NPC59453
0.6333	Remote Similarity	NPC47761
0.6333	Remote Similarity	NPC488870
0.6316	Remote Similarity	NPC51014
0.6167	Remote Similarity	NPC243985
0.6167	Remote Similarity	NPC473943
0.6167	Remote Similarity	NPC280710
0.6167	Remote Similarity	NPC240650
0.6167	Remote Similarity	NPC155011
0.6066	Remote Similarity	NPC474164
0.6038	Remote Similarity	NPC96319
0.5965	Remote Similarity	NPC328313
0.5882	Remote Similarity	NPC158088
0.5781	Remote Similarity	NPC601043
0.5781	Remote Similarity	NPC605412
0.5738	Remote Similarity	NPC477522
0.5593	Remote Similarity	NPC76879
0.5574	Remote Similarity	NPC1272
0.5574	Remote Similarity	NPC470614
0.5517	Remote Similarity	NPC151519
0.5424	Remote Similarity	NPC20688
0.5385	Remote Similarity	NPC474189
0.5312	Remote Similarity	NPC474330
0.5254	Remote Similarity	NPC307965
0.5254	Remote Similarity	NPC18603
0.5254	Remote Similarity	NPC491013
0.5217	Remote Similarity	NPC309493
0.5161	Remote Similarity	NPC87604
0.5152	Remote Similarity	NPC474349
0.5082	Remote Similarity	NPC129165
0.5075	Remote Similarity	NPC176012

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC14042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7586
0.1-0.2	1382
0.2-0.3	152
0.3-0.4	18
0.4-0.5	7
0.5-0.6	1
0.6-0.7	3
0.7-0.8	1
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
0.7358	Intermediate Similarity	NPD7339	Approved
0.6852	Remote Similarity	NPD6942	Phase 4
0.6667	Remote Similarity	NPD4786	Phase 1
0.6038	Remote Similarity	NPD3701	Pre-clinical
0.5517	Remote Similarity	NPD3667	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