NPASS Compound

Natural Product: NPC249797

Natural Product ID	NPC249797
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(13Ar)-3,10-Dimethoxy-6,8,13,13A-Tetrahydro-5H-Isoquinolino[2,1-B]Isoquinoline-2,9-Diol
IUPAC Name	(13aR)-3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1395394
PubChem CID	1152279
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids 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 45 48 0 0 0 0 0 0 0 0999 V2000 -6.4700 1.4843 1.0993 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6437 1.3671 -0.0439 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4046 0.7603 0.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9692 0.2788 1.3275 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7606 -0.3209 1.5119 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9047 -0.4599 0.4034 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6017 -1.1103 0.6039 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3009 -0.8764 -0.5511 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6753 -0.6266 0.0033 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0218 -1.3229 1.1511 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2626 -1.1400 1.7094 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1309 -0.2628 1.1054 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7713 0.4305 -0.0471 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5272 0.2504 -0.6112 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1419 0.9839 -1.8400 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9031 0.3606 -2.4484 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0796 0.1999 -1.4143 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3965 -0.1398 -1.9843 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3294 0.0163 -0.8119 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5579 0.6178 -0.9641 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8891 1.0644 -2.2386 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3771 -0.1034 1.6984 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2850 0.7937 1.0937 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6310 -1.8390 2.8750 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4536 1.9454 0.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0398 2.1915 1.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6947 0.4918 1.5545 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6434 0.3957 2.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4064 -0.7057 2.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1991 -0.7193 1.5694 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7741 -2.2156 0.6841 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4007 -1.7812 -1.2147 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3515 -2.0251 1.6476 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5128 1.1032 -0.4614 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0179 2.0641 -1.6388 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9662 0.8529 -2.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1691 -0.6087 -2.9007 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5627 1.0703 -3.2485 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3393 -1.2029 -2.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6665 0.5163 -2.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3835 0.4234 -2.8729 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2308 0.8522 1.6515 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5122 0.4809 0.0328 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8597 1.8226 1.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9957 -2.7909 2.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 12 22 1 0 22 23 1 0 11 24 1 0 20 3 1 0 19 6 1 0 17 8 1 0 14 9 1 0 1 25 1 0 1 26 1 0 1 27 1 0 4 28 1 0 5 29 1 0 7 30 1 0 7 31 1 0 8 32 1 6 10 33 1 0 13 34 1 0 15 35 1 0 15 36 1 0 16 37 1 0 16 38 1 0 18 39 1 0 18 40 1 0 21 41 1 0 23 42 1 0 23 43 1 0 23 44 1 0 24 45 1 0 M END

Standard InCHIKey	KNWVMRVOBAFFMH-OAHLLOKOSA-N
Standard InCHI	InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m1/s1
SMILES	COc1ccc2C[C@@H]3c4cc(c(cc4CCN3Cc2c1O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	327.15	Volume:	333.293 ? Van der Waals volume.
Dense:	0.982	LogP:	1.38 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.599 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.491 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	21.0
TPSA:	62.16 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.888	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.994	Fsp³:	0.368
MCE-18:	74.462 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.281	Fluc inhibitor:	0.019 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.626 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.446 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.103

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.094	MDCK Permeability:	-4.752
Pgp-inhibitor:	0.779	Pgp-substrate:	0.337
PAMPA:	0.005 ? 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):	0.007
20% Bioavailability (F20%):	0.22	30% Bioavailability (F30%):	0.175
50% Bioavailability (F50%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.525	MRP1:	0.93
Plasma Protein Binding (PPB):	85.945%	Volume Distribution (VD):	-0.325
Fu:	13.028% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.867
BSEP inhibitor:	0.867

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.999
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.994	CYP3A4-substrate:	0.946
CYP2B6-substrate:	0.936	CYP2C8-inhibitor:	0.931
HLM stability:	0.988 ? 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):

3.652

Half-life (T1/2):

2.235

ADMET: Toxicity

hERG Blockers:	0.234	hERG Blockers (10um):	0.611
Human Hepatotoxicity (H-HT):	0.555	Drug-induced Liver Injury (DILI):	0.094
AMES Toxicity:	0.634	Rat Oral Acute Toxicity:	0.486
Maximum Recommended Daily Dose:	0.741	Skin Sensitization:	0.822
Carcinogencity:	0.65	Eye Corrosion:	0.003
Eye Irritation:	0.729	Respiratory Toxicity:	0.864
Drug-induced Neurotoxicity:	0.49	Ototoxicity:	0.472
Hematotoxicity:	0.156	Drug-induced Nephrotoxicity:	0.285
Genotoxicity:	0.344	RPMI-8226 Immunitoxicity:	0.097
A549 Cytotoxicity:	0.307	Hek293 Cytotoxicity:	0.461
BCF:	1.513 ? 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:	3.997 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.198 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.647 ? 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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 21030913]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	small food enterprises (Zvijezda d.d., Zagreb, Croatia)	n.a.	DOI[10.1002/EJLT.200900231]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)98060-9]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1042/BA20020118]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1042/bst0160071]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1556/abot.45.2003.3-4.15]
NPO29263	Tylopilus plumbeoviolaceus	Species	Boletaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[10785434]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11559179]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16660462]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17366734]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	flower petals	n.a.	n.a.	PMID[17480100]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18001808]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23479199]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34964904]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36500609]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36529712]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37685099]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[6361218]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2466	Aloe microstigma	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7312	Aplidium multiplicatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10176	Chrozophora prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17311	Penicillium vulpinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29441	Eremophila oppositifolia	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29206	Lycopodium chinense	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29263	Tylopilus plumbeoviolaceus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29246	Ixeris repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29086	Dovyalis hebecarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29868	Dicentra spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29271	Erycibe obtusifolia	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29868	Dicentra spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12329	Erycibe schmidtii	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15036	Rhus lanceolata	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12329	Erycibe schmidtii	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17796	Lamprocapnos spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29271	Erycibe obtusifolia	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15036	Rhus lanceolata	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12329	Erycibe schmidtii	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29868	Dicentra spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29271	Erycibe obtusifolia	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12329	Erycibe schmidtii	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29271	Erycibe obtusifolia	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7312	Aplidium multiplicatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2466	Aloe microstigma	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15036	Rhus lanceolata	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29347	Hydnum aurantiacum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10176	Chrozophora prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17311	Penicillium vulpinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29441	Eremophila oppositifolia	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29490	Taxillus yadoriki	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29086	Dovyalis hebecarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29246	Ixeris repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29263	Tylopilus plumbeoviolaceus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29206	Lycopodium chinense	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17796	Lamprocapnos spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	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
Potency	12
AC50	4
Ki	1
Inhibition	4

Activity Type	# Activity
Individual protein	20
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT213	Individual protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT277	Individual protein	Caspase-1	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	31.6	nM	PubChem BioAssay data set
NPT213	Individual protein	Cytochrome P450 2C19	Homo sapiens	AC50	=	7943.28	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	12589.25	nM	PubChem BioAssay data set
NPT208	Individual protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	15848.93	nM	PubChem BioAssay data set
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	31.62	nM	PubChem BioAssay data set
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	Ki	=	529.0	nM	PMID[23332346]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	Inhibition	=	84.5	%	PMID[23332346]
NPT243	Individual protein	Dopamine D2 receptor	Homo sapiens	Inhibition	=	31.8	%	PMID[23332346]
NPT290	Individual protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Inhibition	=	26.3	%	PMID[23332346]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	1122.0	nM	PubChem BioAssay data set
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT444	Individual protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	39990.7	nM	PubChem BioAssay data set
NPT444	Individual protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT92	Individual protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Inhibition	=	2.0	%	PMID[23332346]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2238.7	nM	PubChem BioAssay data set

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 NPC249797 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	27628
0.1-0.2	19722
0.2-0.3	2241
0.3-0.4	203
0.4-0.5	30
0.5-0.6	14
0.6-0.7	9
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC193949
0.8036	Intermediate Similarity	NPC276588
0.8036	Intermediate Similarity	NPC127674
0.8036	Intermediate Similarity	NPC278799
0.7377	Intermediate Similarity	NPC276944
0.7377	Intermediate Similarity	NPC238530
0.7167	Intermediate Similarity	NPC295691
0.7167	Intermediate Similarity	NPC207757
0.7167	Intermediate Similarity	NPC54379
0.7143	Intermediate Similarity	NPC88249
0.6833	Remote Similarity	NPC189266
0.6833	Remote Similarity	NPC2413
0.6833	Remote Similarity	NPC110416
0.6515	Remote Similarity	NPC232514
0.6349	Remote Similarity	NPC204828
0.6349	Remote Similarity	NPC5238
0.6271	Remote Similarity	NPC220858
0.6032	Remote Similarity	NPC469817
0.6032	Remote Similarity	NPC172765
0.5968	Remote Similarity	NPC151895
0.5806	Remote Similarity	NPC147390
0.5806	Remote Similarity	NPC428
0.5469	Remote Similarity	NPC321505
0.5469	Remote Similarity	NPC179825
0.5385	Remote Similarity	NPC39701
0.5385	Remote Similarity	NPC184026
0.5294	Remote Similarity	NPC264850
0.5156	Remote Similarity	NPC210437
0.5156	Remote Similarity	NPC16107
0.5156	Remote Similarity	NPC106295
0.5147	Remote Similarity	NPC312025
0.5085	Remote Similarity	NPC192768
0.5077	Remote Similarity	NPC51957

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC249797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4112
0.1-0.2	4871
0.2-0.3	157
0.3-0.4	8
0.4-0.5	1
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5156	Remote Similarity	NPD4584	Phase 2

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