NPASS Compound

Natural Product: NPC193770

Natural Product ID	NPC193770
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Abietadien-18-Al
IUPAC Name	(1R,4aR,4bR,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carbaldehyde
Synonyms	Abietadien-18-al
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL563793
PubChem CID	443479
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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 51 53 0 0 0 0 0 0 0 0999 V2000 -5.1686 1.8516 -0.7417 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3084 1.5071 0.0343 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4601 0.3002 -0.1690 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9224 -0.3146 -1.4792 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8442 -0.6470 0.9484 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8320 -1.7005 1.1990 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4433 -1.1814 1.4082 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0217 -0.2849 0.2878 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0512 0.7251 -0.1350 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5778 1.3319 -1.4239 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1100 1.3643 -1.5433 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7573 1.0267 -0.6075 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1897 0.5721 0.6870 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1491 -0.0888 1.5878 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4179 -0.5613 0.9703 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9959 0.3325 -0.0531 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1999 1.0839 -0.7988 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4643 0.4161 -0.2751 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0811 0.9248 1.0139 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0574 -0.9093 -0.6727 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5394 -1.1687 -0.8457 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1408 2.0975 0.9196 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9329 -0.7663 -1.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3121 -1.1302 -1.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0532 0.4906 -2.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0067 -0.0878 1.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8008 -1.1179 0.6870 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1234 -2.2496 2.1197 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8632 -2.4469 0.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7791 -2.0967 1.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3637 -0.6672 2.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9884 1.5605 0.6312 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0560 0.8370 -2.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9481 2.3802 -1.4610 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3032 1.6957 -2.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1933 1.5161 1.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7216 -0.9689 2.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4401 0.6188 2.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1899 -0.6423 1.7936 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3658 -1.6127 0.5717 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5631 1.7578 -1.5640 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6786 1.1274 -1.0969 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3224 1.0617 1.8176 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5222 1.9232 0.8382 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8830 0.2229 1.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8797 -1.1330 -1.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6865 -1.7532 -0.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1539 -0.8465 -0.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9383 -0.9258 -1.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5650 -1.1731 -0.9427 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8087 -2.2513 -0.6642 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 6 3 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 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 18 20 1 0 8 21 1 6 9 3 1 0 17 12 1 0 13 8 1 0 2 22 1 0 4 23 1 0 4 24 1 0 4 25 1 0 5 26 1 0 5 27 1 0 6 28 1 0 6 29 1 0 7 30 1 0 7 31 1 0 9 32 1 1 10 33 1 0 10 34 1 0 11 35 1 0 13 36 1 1 14 37 1 0 14 38 1 0 15 39 1 0 15 40 1 0 17 41 1 0 18 42 1 0 19 43 1 0 19 44 1 0 19 45 1 0 20 46 1 0 20 47 1 0 20 48 1 0 21 49 1 0 21 50 1 0 21 51 1 0 M END

Standard InCHIKey	HOFSYSONRIGEAC-LWYYNNOASA-N
Standard InCHI	InChI=1S/C20H30O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h7,12-14,17-18H,5-6,8-11H2,1-4H3/t17-,18-,19-,20+/m0/s1
SMILES	O=C[C@]1(C)CCC[C@]2([C@H]1CC=C1[C@@H]2CCC(=C1)C(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	286.23	Volume:	329.688 ? Van der Waals volume.
Dense:	0.868	LogP:	4.572 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.881 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.698 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	17.0
TPSA:	17.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.628	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.43	Fsp³:	0.75
MCE-18:	51.429 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.812	Fluc inhibitor:	0.188 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.951	Promiscuous compounds:	0.034

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.43	MDCK Permeability:	-4.755
Pgp-inhibitor:	0.995	Pgp-substrate:	0.001
PAMPA:	0.019 ? 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%):	0.152	30% Bioavailability (F30%):	0.232
50% Bioavailability (F50%):	0.816

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113	MRP1:	0.896
Plasma Protein Binding (PPB):	95.869%	Volume Distribution (VD):	0.393
Fu:	3.758% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.764
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.998	CYP1A2-substrate:	0.843
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.628
CYP2C9-inhibitor:	0.525	CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.014	CYP2D6-substrate:	0.964
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.356	CYP2C8-inhibitor:	0.904
HLM stability:	0.981 ? 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):

9.166

Half-life (T1/2):

0.202

ADMET: Toxicity

hERG Blockers:	0.046	hERG Blockers (10um):	0.287
Human Hepatotoxicity (H-HT):	0.563	Drug-induced Liver Injury (DILI):	0.249
AMES Toxicity:	0.379	Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.577	Skin Sensitization:	0.975
Carcinogencity:	0.848	Eye Corrosion:	0.821
Eye Irritation:	0.964	Respiratory Toxicity:	0.652
Drug-induced Neurotoxicity:	0.272	Ototoxicity:	0.251
Hematotoxicity:	0.565	Drug-induced Nephrotoxicity:	0.62
Genotoxicity:	0.835	RPMI-8226 Immunitoxicity:	0.102
A549 Cytotoxicity:	0.225	Hek293 Cytotoxicity:	0.456
BCF:	2.221 ? 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:	4.485 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.649 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.32 ? 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
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94598-9]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2225/vol5-issue3-fulltext-4]
NPO21179	Streptomyces griseoaurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10048567]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325242]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088440]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713420]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15009205]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038560]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21500777]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25323720]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	rhizomes	Liaoning province, China	2011-SEP	PMID[25927664]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26731565]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31419126]
NPO18735	Pinus mugo	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31475763]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32078653]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35889256]
NPO54216	Pinus contorta subsp. latifolia	Genus	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36985451]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37241721]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37800169]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38370080]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39684509]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12801	Aglaia meridionalis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18061	Anacystis cyanea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17718	Artemisia schmidtiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19189	Brickellia pendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18377	Chaetomium retardatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17275	Chamaemelum scariosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3050	Cladonia pseudodidyma	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21938	Coleus carnosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18847	Copaifera paupera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9535	Cortinarius basirubescens	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18792	Crotalaria lechnaultii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16829	Dunaliella acidophila	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12072	Escallonia philippiana	Species	Escalloniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17596	Ficus maxima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18242	Gleichenia glauca	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18520	Helipterum strictum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3746	Hesperocyparis nevadensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13594	Hippocratea indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11677	Lactobacillus acidophilus	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11603	Lathyrus macrorrhizus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19057	Lentinellus omphalodes	Species	Auriscalpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18575	Ochtodes crockeri	Species	Rhizophyllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12282	Parmelia conspersa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7807	Polyporus sulphureus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18173	Pyrocystis lunula	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17190	Senecio erraticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10712	Tabebuia rosea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17068	Talaromyces wortmanni	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15608	Tanacetum santolina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17709	Timonius kaniensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18735	Pinus mugo	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14307	Rhizopus oryzae	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22530	Vigna luteola	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13308	Polycitor adriaticus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21179	Streptomyces griseoaurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14307	Rhizopus oryzae	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11677	Lactobacillus acidophilus	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18173	Pyrocystis lunula	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3050	Cladonia pseudodidyma	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9535	Cortinarius basirubescens	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7807	Polyporus sulphureus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17709	Timonius kaniensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3746	Hesperocyparis nevadensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18847	Copaifera paupera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13594	Hippocratea indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18735	Pinus mugo	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22147	Goniothalamus macrophyllus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21938	Coleus carnosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17718	Artemisia schmidtiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18575	Ochtodes crockeri	Species	Rhizophyllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21894	Psychotria granadensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12282	Parmelia conspersa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12072	Escallonia philippiana	Species	Escalloniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17068	Talaromyces wortmanni	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22968	Elaeocarpus serratus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11603	Lathyrus macrorrhizus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15469	Myodocarpus gracilis	Species	Myodocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10712	Tabebuia rosea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6953.1	Aconitum sachalinense subsp. yezoense	Subspecies	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19189	Brickellia pendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20425	Epimedium macranthum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15608	Tanacetum santolina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18520	Helipterum strictum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17275	Chamaemelum scariosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23194	Berberis beaniana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18061	Anacystis cyanea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21704	Papaver suaveolens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17190	Senecio erraticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18242	Gleichenia glauca	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17596	Ficus maxima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18377	Chaetomium retardatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23157	Wigandia kunthii	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16829	Dunaliella acidophila	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19057	Lentinellus omphalodes	Species	Auriscalpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12801	Aglaia meridionalis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18792	Crotalaria lechnaultii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14307	Rhizopus oryzae	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13308	Polycitor adriaticus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21179	Streptomyces griseoaurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22530	Vigna luteola	Species	Fabaceae	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
NPO18735	Pinus mugo	Oil	n.a.	0.1	n.a.	n.a.	%	PMID[31475763]
NPO18735	Pinus mugo	Oil	n.a.	0.2	n.a.	n.a.	%	PMID[31475763]
NPO54216	Pinus contorta subsp. latifolia	Oil	Leaves	0.2	n.a.	n.a.	%	PMID[36985451]
NPO54216	Pinus contorta subsp. latifolia	Oil	Leaves	0.1	n.a.	n.a.	%	PMID[36985451]

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
MIC	1
CC100	1
Activity	2
CC50	2

Activity Type	# Activity
Cell line	3
Organism	3

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
NPT165	Cell line	HeLa	Homo sapiens	CC100	>	50.0	ug ml-1	PMID[19217699]
NPT165	Cell line	HeLa	Homo sapiens	CC50	=	5.6	ug.mL-1	PMID[19217699]
NPT189	Cell line	Vero	Chlorocebus aethiops	CC50	=	31.5	ug.mL-1	PMID[19217699]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	10.0	n.a.	PMID[19217699]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	12.5	ug ml-1	PMID[19217699]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	50.0	ug.mL-1	PMID[19217699]

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 NPC193770 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	26492
0.1-0.2	21267
0.2-0.3	1968
0.3-0.4	120
0.4-0.5	4
0.5-0.6	4
0.6-0.7	3
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
0.68	Remote Similarity	NPC4827
0.6739	Remote Similarity	NPC216460
0.6735	Remote Similarity	NPC899
0.5577	Remote Similarity	NPC483604
0.541	Remote Similarity	NPC15910
0.5185	Remote Similarity	NPC309399
0.5098	Remote Similarity	NPC268039

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC193770 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7698
0.1-0.2	1384
0.2-0.3	67
0.3-0.4	1
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