NPASS Compound

Natural Product: NPC284183

Natural Product ID	NPC284183
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cephaeline
IUPAC Name	(1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol
Synonyms	Cephaeline
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL255708
PubChem CID	442195
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002659] Emetine alkaloids

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 72 76 0 0 0 0 0 0 0 0999 V2000 -1.1354 3.2878 3.2650 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2120 1.8957 2.6814 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2846 1.7221 1.5019 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1342 1.9908 2.0379 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0625 1.8196 0.9341 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3728 2.3299 1.2038 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1738 2.2357 -0.0833 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2465 0.8130 -0.5042 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3224 0.3418 -1.2380 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4109 -0.9811 -1.6416 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3803 -1.8239 -1.2843 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3031 -1.3404 -0.5466 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2119 -0.0352 -0.1464 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0591 0.4067 0.6272 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7134 0.1229 -0.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3102 0.3135 1.0600 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6320 -0.2982 0.7834 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4527 0.3536 -0.2822 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7473 -0.3044 -0.5172 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4443 -0.8288 0.5421 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6757 -1.4581 0.3244 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2155 -1.5694 -0.9214 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5160 -1.0414 -1.9956 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3050 -0.4256 -1.7610 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6089 0.1237 -2.9605 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1237 -0.0207 -2.6560 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7489 0.6716 -1.4712 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.4522 -2.1975 -1.1703 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3645 -1.9827 1.4103 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8735 -1.9074 2.7296 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4660 -3.1474 -1.6859 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4684 -4.1082 -1.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4954 -1.4613 -2.3826 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5355 -0.5708 -2.7312 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2775 3.3352 3.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0876 3.4987 3.7969 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9307 4.0275 2.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2599 1.6731 2.4744 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8795 1.1686 3.4605 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4191 2.4740 0.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3731 1.3224 2.8818 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1954 3.0681 2.3221 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2734 3.3978 1.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8869 1.8403 2.0533 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6219 2.8405 -0.8329 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1870 2.6670 0.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1495 0.9961 -1.5306 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5270 -2.0412 -0.2953 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0021 -0.1221 1.6169 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5562 0.7768 -0.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7102 -0.9626 -0.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1210 -0.2913 1.9204 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1696 -0.3491 1.7519 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4501 -1.3504 0.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7456 1.3667 0.1505 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0904 -0.7833 1.5773 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9624 -1.1421 -2.9697 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8373 -0.4960 -3.8415 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8331 1.2055 -3.1053 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7956 -1.0618 -2.6652 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6021 0.4915 -3.5152 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5445 1.6954 -1.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9500 -2.5109 -0.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4718 -2.5505 3.4106 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8109 -2.2243 2.8161 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9406 -0.8565 3.0776 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2131 -3.9617 -0.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5739 -3.8879 -1.9939 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8573 -5.1311 -1.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3868 -1.1807 -3.1307 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2214 0.1696 -3.5047 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9483 -0.0368 -1.8306 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 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 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 22 28 1 0 21 29 1 0 29 30 1 0 11 31 1 0 31 32 1 0 10 33 1 0 33 34 1 0 16 3 1 0 27 18 1 0 14 5 1 0 24 19 1 0 13 8 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 2 39 1 0 3 40 1 6 4 41 1 0 4 42 1 0 6 43 1 0 6 44 1 0 7 45 1 0 7 46 1 0 9 47 1 0 12 48 1 0 14 49 1 1 15 50 1 0 15 51 1 0 16 52 1 1 17 53 1 0 17 54 1 0 18 55 1 1 20 56 1 0 23 57 1 0 25 58 1 0 25 59 1 0 26 60 1 0 26 61 1 0 27 62 1 0 28 63 1 0 30 64 1 0 30 65 1 0 30 66 1 0 32 67 1 0 32 68 1 0 32 69 1 0 34 70 1 0 34 71 1 0 34 72 1 0 M END

Standard InCHIKey	DTGZHCFJNDAHEN-OZEXIGSWSA-N
Standard InCHI	InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3/t17-,20-,23+,24-/m0/s1
SMILES	CC[C@H]1CN2CCc3cc(c(cc3[C@@H]2C[C@@H]1C[C@@H]1c2cc(c(cc2CCN1)O)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	466.28	Volume:	491.397 ? Van der Waals volume.
Dense:	0.949	LogP:	2.51 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.392 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.627 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	27.0
TPSA:	63.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.647	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.986	Fsp³:	0.571
MCE-18:	96.727 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.603	Fluc inhibitor:	0.073 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.49 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.455 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.557

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.304	MDCK Permeability:	-5.022
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
PAMPA:	0.008 ? 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%):	0.082	30% Bioavailability (F30%):	0.205
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.986
Plasma Protein Binding (PPB):	66.523%	Volume Distribution (VD):	0.148
Fu:	35.711% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.913
OATP1B3 inhibitor:	0.966	BCRP inhibitor:	0.208
BSEP inhibitor:	0.049

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.064	CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.959	CYP3A4-substrate:	0.772
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.024
HLM stability:	0.081 ? 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):

8.441

Half-life (T1/2):

1.854

ADMET: Toxicity

hERG Blockers:	0.71	hERG Blockers (10um):	0.749
Human Hepatotoxicity (H-HT):	0.662	Drug-induced Liver Injury (DILI):	0.101
AMES Toxicity:	0.458	Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.971	Skin Sensitization:	0.723
Carcinogencity:	0.584	Eye Corrosion:	0.0
Eye Irritation:	0.016	Respiratory Toxicity:	0.975
Drug-induced Neurotoxicity:	0.938	Ototoxicity:	0.575
Hematotoxicity:	0.143	Drug-induced Nephrotoxicity:	0.878
Genotoxicity:	0.358	RPMI-8226 Immunitoxicity:	0.155
A549 Cytotoxicity:	0.769	Hek293 Cytotoxicity:	0.623
BCF:	1.54 ? 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:	3.929 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.163 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.495 ? 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
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1171883]
NPO18851	Psychotria klugii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880315]
NPO18851	Psychotria klugii	Species	Rubiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[12880315]
NPO22241	Alangium villosum	Species	Cornaceae	Eukaryota	stem bark	Ceram, Indonesia	1998	PMID[18327911]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19500975]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23387901]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31513408]
NPO22241	Alangium villosum	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32372642]
NPO2719	Amauroascus aureus	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5735362]
NPO24848	Acodontaster conspicuus	Species	Odontasteridae	Eukaryota	n.a.	Antarctic	n.a.	PMID[9358635]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5056	Helichrysum heterolasium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18346	Alangium lamarckii	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18851	Psychotria klugii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25409	Ascochyta caulina	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31365	Cephaelis ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24521	Helichrysum revolutum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21010	Streptomyces avidinii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24848	Acodontaster conspicuus	Species	Odontasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22241	Alangium villosum	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18346	Alangium lamarckii	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31365	Cephaelis ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23138	Swainsona salsula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18346	Alangium lamarckii	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2719	Amauroascus aureus	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22548	Osteospermum jucundum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26637.1	Mentha aquatica var. citrata	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25098	Spinacia glabra	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24211	Parmelia cetrarioides	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24880	Bacterial str	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23138	Swainsona salsula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24646	Coryphantha elephantidens	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23623	Hirsutella nivea	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5056	Helichrysum heterolasium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18432	Poria corticola	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24848	Acodontaster conspicuus	Species	Odontasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21010	Streptomyces avidinii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25360	Helminthosporium ravenelii	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25409	Ascochyta caulina	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24521	Helichrysum revolutum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22241	Alangium villosum	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18851	Psychotria klugii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18346	Alangium lamarckii	Species	Cornaceae	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
MIC	1
IC50	16
Activity	7
Ratio IC50	2
IC90	1
Ratio	1

Activity Type	# Activity
Individual protein	2
Cell line	16
Organism	7
Others	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2536	Individual protein	Leukocyte adhesion glycoprotein LFA-1 alpha	Homo sapiens	MIC	=	6.9	ug.mL-1	PMID[12880315]
NPT2536	Individual protein	Leukocyte adhesion glycoprotein LFA-1 alpha	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[12880315]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell line	DU-145	Homo sapiens	Activity	=	0.0098	ug ml-1	PMID[18327911]
NPT168	Cell line	P388	Mus musculus	Activity	=	0.0027	ug ml-1	PMID[18327911]
NPT377	Cell line	OVCAR-3	Homo sapiens	Activity	=	0.032	ug ml-1	PMID[18327911]
NPT397	Cell line	NCI-H460	Homo sapiens	Activity	=	0.022	ug ml-1	PMID[18327911]
NPT575	Cell line	KM-20L2	Homo sapiens	Activity	=	0.022	ug ml-1	PMID[18327911]
NPT1081	Cell line	BXPC-3	Homo sapiens	Activity	=	0.024	ug ml-1	PMID[18327911]
NPT399	Cell line	SF-295	Homo sapiens	Activity	=	0.018	ug ml-1	PMID[18327911]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	5.3	ug.mL-1	PMID[12880315]
NPT916	Cell line	SK-MEL	Homo sapiens	IC50	=	0.25	ug.mL-1	PMID[12880315]
NPT91	Cell line	KB	Homo sapiens	IC50	=	0.33	ug.mL-1	PMID[12880315]
NPT457	Cell line	BT-549	Homo sapiens	IC50	=	0.86	ug.mL-1	PMID[12880315]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	0.18	ug.mL-1	PMID[12880315]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	14.9	ug.mL-1	PMID[12880315]
NPT81	Cell line	A549	Homo sapiens	IC50	=	3000.0	nM	PMID[31513408]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	7600.0	nM	PMID[31513408]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	100.0	nM	PMID[31513408]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.038	ug.mL-1	PMID[12880315]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0277	ug.mL-1	PMID[12880315]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	3.26	ug.mL-1	DOI[10.1007/s00044-011-9767-1]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	DOI[10.6019/CHEMBL4651402]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	DOI[10.6019/CHEMBL4651402]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	0.03	ug.mL-1	PMID[12880315]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	1.5	ug.mL-1	PMID[12880315]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	132.0	n.a.	PMID[12880315]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	193.0	n.a.	PMID[12880315]
NPT2	Others	Unspecified	n.a.	Ratio	=	2.17	n.a.	PMID[12880315]

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 NPC284183 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	28225
0.1-0.2	20422
0.2-0.3	1092
0.3-0.4	100
0.4-0.5	6
0.5-0.6	7
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC4138
0.8529	High Similarity	NPC80129
0.8529	High Similarity	NPC187022
0.8472	Intermediate Similarity	NPC121275
0.6024	Remote Similarity	NPC109925
0.5904	Remote Similarity	NPC66573
0.589	Remote Similarity	NPC229031
0.5789	Remote Similarity	NPC48291
0.5745	Remote Similarity	NPC280272
0.5625	Remote Similarity	NPC21466
0.5484	Remote Similarity	NPC176284
0.5256	Remote Similarity	NPC479826

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC284183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4667
0.1-0.2	4331
0.2-0.3	139
0.3-0.4	6
0.4-0.5	6
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8529	High Similarity	NPD7298	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