NPASS Compound

Natural Product: NPC290287

Natural Product ID	NPC290287
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VOXZDWNPVJITMN-PNKHAZJDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	126969992
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001466] Estrane steroids [CHEMONTID:0003570] Estrogens 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 44 47 0 0 0 0 0 0 0 0999 V2000 -3.0390 -1.4833 0.5787 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1707 -0.5734 -0.2274 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2762 -1.2865 -1.2011 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1925 -2.0839 -0.5266 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6261 -1.3176 0.4416 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7546 -0.5589 -0.1381 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1758 -0.6346 -1.4261 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2384 0.0998 -1.9094 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9070 0.9564 -1.0337 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4896 1.0395 0.2671 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4250 0.2948 0.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9582 0.3720 2.1347 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4808 0.3961 2.2749 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2626 -0.5025 1.3267 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3270 0.2830 0.6523 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8730 1.3784 -0.2341 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0153 1.5509 -1.2318 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9782 0.4395 -1.0001 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0821 0.8748 -0.2519 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9842 1.7093 -1.4984 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0546 -1.5908 0.1271 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2253 -0.9670 1.5651 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5692 -2.4368 0.8167 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8326 -0.5159 -1.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8864 -1.9748 -1.7979 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3593 -2.6259 -1.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7303 -2.8920 0.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1147 -2.0814 1.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6663 -1.2939 -2.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5939 0.0586 -2.9287 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9950 1.7036 0.9784 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4596 -0.4295 2.7387 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3785 1.3369 2.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1534 1.4693 2.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2469 0.1813 3.3549 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8004 -1.2581 1.9797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9613 0.7242 1.4500 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7960 2.3475 0.3017 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0271 1.2043 -0.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6612 1.4869 -2.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 2.5073 -1.1246 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3439 -0.0266 -1.9413 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8454 1.7505 0.1767 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4224 2.3686 -0.8977 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 9 20 1 0 15 2 1 0 18 2 1 0 14 5 1 0 11 6 1 0 1 21 1 0 1 22 1 0 1 23 1 0 3 24 1 0 3 25 1 0 4 26 1 0 4 27 1 0 5 28 1 1 7 29 1 0 8 30 1 0 10 31 1 0 12 32 1 0 12 33 1 0 13 34 1 0 13 35 1 0 14 36 1 1 15 37 1 1 16 38 1 0 16 39 1 0 17 40 1 0 17 41 1 0 18 42 1 6 19 43 1 0 20 44 1 0 M END

Standard InCHIKey	VOXZDWNPVJITMN-PNKHAZJDSA-N
Standard InCHI	InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15+,16+,17-,18-/m0/s1
SMILES	C[C@]12CC[C@H]3c4ccc(cc4CC[C@H]3[C@H]1CC[C@@H]2O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	272.18	Volume:	295.329 ? Van der Waals volume.
Dense:	0.922	LogP:	3.884 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.628 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.574 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	20.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.757	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.585	Fsp³:	0.667
MCE-18:	82.133 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.285	Fluc inhibitor:	0.308 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.064 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.41	Promiscuous compounds:	0.194

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.788	MDCK Permeability:	-4.658
Pgp-inhibitor:	0.006	Pgp-substrate:	0.893
PAMPA:	0.385 ? 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):	0.001
20% Bioavailability (F20%):	0.974	30% Bioavailability (F30%):	0.914
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992	MRP1:	0.916
Plasma Protein Binding (PPB):	82.086%	Volume Distribution (VD):	0.047
Fu:	21.923% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.915
OATP1B3 inhibitor:	0.987	BCRP inhibitor:	0.56
BSEP inhibitor:	0.339

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.271
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.392
CYP2D6-inhibitor:	0.978	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.176	CYP3A4-substrate:	0.885
CYP2B6-substrate:	0.997	CYP2C8-inhibitor:	0.99
HLM stability:	0.985 ? 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):

13.284

Half-life (T1/2):

1.591

ADMET: Toxicity

hERG Blockers:	0.154	hERG Blockers (10um):	0.596
Human Hepatotoxicity (H-HT):	0.736	Drug-induced Liver Injury (DILI):	0.048
AMES Toxicity:	0.44	Rat Oral Acute Toxicity:	0.427
Maximum Recommended Daily Dose:	0.706	Skin Sensitization:	0.911
Carcinogencity:	0.942	Eye Corrosion:	0.026
Eye Irritation:	0.935	Respiratory Toxicity:	0.902
Drug-induced Neurotoxicity:	0.111	Ototoxicity:	0.6
Hematotoxicity:	0.23	Drug-induced Nephrotoxicity:	0.189
Genotoxicity:	0.122	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.49	Hek293 Cytotoxicity:	0.656
BCF:	1.578 ? 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:	4.106 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.205 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.822 ? 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
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[10670815]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038554]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[17226159]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17237222]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	Malatya Fruit Research Institute	between the first and third weeks of 2005-Jul.	PMID[18038980]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18044840]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21381684]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21381684]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	stem	n.a.	PMID[21381684]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22187429]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23784883]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24400858]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26934105]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[27133212]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7792	Coreopsis grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15434	Rhodomicrobium vannielii	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13740	Aconitum kamtschaticum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16109	Actinidia kolomikta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15679	Amyris marshii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12470	Brachyspira hyodysenteriae	Species	Brachyspiraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7077	Canarium strictum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15312	Coelogorgia palmosa	Species	Coelogorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14604	Dipteronia dyeriana	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9386	Ectropis bicolor	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14914	Esox saurus	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11962	Garcinia macrophylla	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14442	Gouania microcarpa	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13582	Leucopaxillus giganteus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13273	Maytenus loeseneri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5750	Monomorium floricola	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10452	Odontites rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3697	Ongokea klaineana	Species	Aptandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2607	Ophiorrhiza blumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16625	Phalaenopsis aphrodite	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8671	Physalis solanaceus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15570	Plectranthus mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15159	Podocarpus salignus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11644	Prosopis ruscifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15178	Psychotria bahiensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16311	Rusavskia elegans	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11376	Schistostephium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1723	Sideritis syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12457	Siphocampylus verticillatus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22056.1	Streptomyces fervens	Subspecies	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12951	Talaromyces coalescens	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14747	Usnea florida	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22053	Vepris pilosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16541	Veratrum stenophyllum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12547	Viburnum chingii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26256	Zanthoxylum chiriquinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13740	Aconitum kamtschaticum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15679	Amyris marshii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15570	Plectranthus mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16625	Phalaenopsis aphrodite	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16541	Veratrum stenophyllum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16311	Rusavskia elegans	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12470	Brachyspira hyodysenteriae	Species	Brachyspiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15434	Rhodomicrobium vannielii	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15159	Podocarpus salignus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12547	Viburnum chingii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13582	Leucopaxillus giganteus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12951	Talaromyces coalescens	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11644	Prosopis ruscifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12457	Siphocampylus verticillatus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13273	Maytenus loeseneri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9386	Ectropis bicolor	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10452	Odontites rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8671	Physalis solanaceus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16109	Actinidia kolomikta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22056.1	Streptomyces fervens	Subspecies	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14604	Dipteronia dyeriana	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2607	Ophiorrhiza blumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3697	Ongokea klaineana	Species	Aptandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14747	Usnea florida	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22053	Vepris pilosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7077	Canarium strictum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7792	Coreopsis grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11376	Schistostephium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14914	Esox saurus	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1723	Sideritis syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26256	Zanthoxylum chiriquinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5750	Monomorium floricola	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15312	Coelogorgia palmosa	Species	Coelogorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15178	Psychotria bahiensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11962	Garcinia macrophylla	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14442	Gouania microcarpa	Species	Gobiesocidae	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 NPC290287 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	17657
0.1-0.2	30705
0.2-0.3	1434
0.3-0.4	38
0.4-0.5	7
0.5-0.6	3
0.6-0.7	7
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC48342
1.0	High Similarity	NPC329477
1.0	High Similarity	NPC164649
0.7593	Intermediate Similarity	NPC328504
0.7547	Intermediate Similarity	NPC321402
0.7143	Intermediate Similarity	NPC77569
0.7143	Intermediate Similarity	NPC142198
0.7143	Intermediate Similarity	NPC324264
0.678	Remote Similarity	NPC321502
0.6607	Remote Similarity	NPC322753
0.6271	Remote Similarity	NPC190501
0.6271	Remote Similarity	NPC318552
0.623	Remote Similarity	NPC30491
0.623	Remote Similarity	NPC99734
0.623	Remote Similarity	NPC262936
0.5574	Remote Similarity	NPC475166
0.5325	Remote Similarity	NPC485859
0.5316	Remote Similarity	NPC10945

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC290287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5678
0.1-0.2	3346
0.2-0.3	88
0.3-0.4	19
0.4-0.5	2
0.5-0.6	8
0.6-0.7	7
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3091	Phase 4
0.7143	Intermediate Similarity	NPD3092	Phase 4
0.678	Remote Similarity	NPD3619	Phase 2
0.678	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD3094	Phase 4
0.6271	Remote Similarity	NPD3019	Phase 4
0.623	Remote Similarity	NPD4059	Phase 4
0.619	Remote Similarity	NPD4140	Phase 4
0.6032	Remote Similarity	NPD3638	Discontinued
0.5909	Remote Similarity	NPD3095	Discontinued
0.5833	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.5571	Remote Similarity	NPD6273	Phase 4
0.5429	Remote Similarity	NPD5736	Phase 4
0.5417	Remote Similarity	NPD5699	Phase 3
0.5325	Remote Similarity	NPD7742	Phase 4
0.5325	Remote Similarity	NPD7743	Approved
0.5205	Remote Similarity	NPD6663	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