NPASS Compound

Natural Product: NPC515911

Natural Product ID	NPC515911
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	octadec-6-enoic acid
IUPAC Name	octadec-6-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 54 53 0 0 0 0 0 0 0 0999 V2000 7.5467 -1.7229 0.3319 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0440 -1.0864 1.6071 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6492 -0.5393 1.3779 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7535 0.4826 0.2747 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4287 1.1237 -0.0677 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 0.0544 -0.5234 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1003 0.7060 -0.8749 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1259 -0.3363 -1.3278 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1901 0.2834 -1.6929 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7876 0.9678 -0.5182 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1267 1.5962 -0.9130 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0498 0.5641 -1.3602 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2068 0.2984 -0.7881 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6840 1.0378 0.3812 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9254 0.2672 1.6065 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0317 -0.6378 1.7616 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4230 -1.7559 0.9240 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0077 -1.5137 -0.4000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3628 -0.3860 -0.8038 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1883 -2.5762 -1.2725 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4414 -2.3682 0.5572 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9106 -0.9787 -0.4016 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7290 -2.3603 -0.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7124 -0.2290 1.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0317 -1.8638 2.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0044 -1.3912 1.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2925 -0.0338 2.2903 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5047 1.2371 0.5435 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0672 -0.0928 -0.6447 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0258 1.7355 0.7489 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6289 1.7860 -0.9496 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2961 -0.6958 0.2636 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8108 -0.4013 -1.4579 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7495 1.2946 -0.0072 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3371 1.4323 -1.6692 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5793 -0.8688 -2.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9174 -1.0815 -0.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9098 -0.4786 -2.0714 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0234 1.0370 -2.5030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1431 1.7270 -0.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9850 0.2005 0.2836 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3999 2.2291 -0.0814 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9058 2.2998 -1.7700 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7956 -0.0505 -2.2517 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7627 -0.4969 -1.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0912 1.9858 0.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7037 1.5355 0.1267 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8649 1.0150 2.4945 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9444 -0.3419 1.8021 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9812 -1.0248 2.8758 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0011 0.0221 1.9211 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5523 -2.4878 0.8114 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2319 -2.3379 1.4954 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8626 -2.6074 -2.0006 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 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 3 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 1 21 1 0 1 22 1 0 1 23 1 0 2 24 1 0 2 25 1 0 3 26 1 0 3 27 1 0 4 28 1 0 4 29 1 0 5 30 1 0 5 31 1 0 6 32 1 0 6 33 1 0 7 34 1 0 7 35 1 0 8 36 1 0 8 37 1 0 9 38 1 0 9 39 1 0 10 40 1 0 10 41 1 0 11 42 1 0 11 43 1 0 12 44 1 0 13 45 1 0 14 46 1 0 14 47 1 0 15 48 1 0 15 49 1 0 16 50 1 0 16 51 1 0 17 52 1 0 17 53 1 0 20 54 1 0 M END

Standard InCHIKey	CNVZJPUDSLNTQU-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)
SMILES	CCCCCCCCCCCC=CCCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	282.26	Volume:	332.192 ? Van der Waals volume.
Dense:	0.85	LogP:	7.142 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.773 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.028 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	2.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.291	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.033	Fsp³:	0.833
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.159	Fluc inhibitor:	0.193 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.022 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.995	Promiscuous compounds:	0.891

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091	MDCK Permeability:	-4.734
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
PAMPA:	0.086 ? 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):	0.64
20% Bioavailability (F20%):	0.393	30% Bioavailability (F30%):	0.831
50% Bioavailability (F50%):	0.257

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022	MRP1:	0.982
Plasma Protein Binding (PPB):	98.206%	Volume Distribution (VD):	-0.227
Fu:	0.724% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.469
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.066
BSEP inhibitor:	0.358

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.95	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.0 ? 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):

4.947

Half-life (T1/2):

0.498

ADMET: Toxicity

hERG Blockers:	0.141	hERG Blockers (10um):	0.344
Human Hepatotoxicity (H-HT):	0.273	Drug-induced Liver Injury (DILI):	0.012
AMES Toxicity:	0.087	Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.154	Skin Sensitization:	0.998
Carcinogencity:	0.174	Eye Corrosion:	0.997
Eye Irritation:	0.998	Respiratory Toxicity:	0.808
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.236
Hematotoxicity:	0.072	Drug-induced Nephrotoxicity:	0.302
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.167	Hek293 Cytotoxicity:	0.056
BCF:	0.813 ? 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:	3.883 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.502 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.611 ? 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
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	DOI[10.1016/0045-6535(91)90110-Y]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.abb.2017.09.009]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2008.08.002]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/j.indcrop.2012.04.060]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003Ã¢â‚¬â€œ2005	DOI[10.1016/j.jfca.2006.05.007]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(02)00288-1]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0885-5765(05)80069-4]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	callus	n.a.	PMID[10552648]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	roots	n.a.	n.a.	PMID[16989524]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18214349]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19778086]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21800857]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22863942]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24042007]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25340465]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[25340465]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25577087]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30827604]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32515616]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33444950]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34885954]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36362399]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432786]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432786]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432786]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37331322]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37379658]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446712]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38719900]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38719900]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38719900]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38838926]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38977255]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15705	Herba coriandri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26967	Phallus impudicus	Species	Phallaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4384	Cetraria aculeata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11192	Hedera helix	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO42652	Streptomyces chumphonensis BDK01	Genus	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf Wax	n.a.	n.a.	Database[FooDB]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11192	Hedera helix	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26967	Phallus impudicus	Species	Phallaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26967	Phallus impudicus	Species	Phallaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11192	Hedera helix	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15705	Herba coriandri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11192	Hedera helix	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4384	Cetraria aculeata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6997	Anthriscus cerefolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11192	Hedera helix	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26967	Phallus impudicus	Species	Phallaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2345	Coriandrum sativum	Species	Apiaceae	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 NPC515911 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	37835
0.1-0.2	10089
0.2-0.3	1478
0.3-0.4	249
0.4-0.5	88
0.5-0.6	47
0.6-0.7	25
0.7-0.8	5
0.8-0.85	8
0.85-0.9	2
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC92114
0.9259	High Similarity	NPC424
0.9259	High Similarity	NPC36061
0.9259	High Similarity	NPC69510
0.9259	High Similarity	NPC77272
0.9259	High Similarity	NPC290563
0.9259	High Similarity	NPC139029
0.9259	High Similarity	NPC281972
0.9259	High Similarity	NPC261831
0.9259	High Similarity	NPC87564
0.8889	High Similarity	NPC281245
0.8621	High Similarity	NPC5413
0.8333	Intermediate Similarity	NPC154245
0.8333	Intermediate Similarity	NPC85813
0.8333	Intermediate Similarity	NPC223697
0.8333	Intermediate Similarity	NPC6095
0.8276	Intermediate Similarity	NPC95145
0.8276	Intermediate Similarity	NPC325642
0.8276	Intermediate Similarity	NPC65174
0.8	Intermediate Similarity	NPC321062
0.7742	Intermediate Similarity	NPC59051
0.7419	Intermediate Similarity	NPC91495
0.7188	Intermediate Similarity	NPC52955
0.7188	Intermediate Similarity	NPC88966
0.7188	Intermediate Similarity	NPC25417
0.7188	Intermediate Similarity	NPC1813
0.7097	Intermediate Similarity	NPC149821
0.7037	Intermediate Similarity	NPC171736
0.7037	Intermediate Similarity	NPC301585
0.7037	Intermediate Similarity	NPC261080
0.7037	Intermediate Similarity	NPC132565
0.7037	Intermediate Similarity	NPC209970
0.7037	Intermediate Similarity	NPC216630
0.7037	Intermediate Similarity	NPC201844
0.7037	Intermediate Similarity	NPC301696
0.7037	Intermediate Similarity	NPC196924
0.7037	Intermediate Similarity	NPC307783
0.7037	Intermediate Similarity	NPC154186
0.7037	Intermediate Similarity	NPC149184
0.7037	Intermediate Similarity	NPC279026
0.7037	Intermediate Similarity	NPC113928
0.7037	Intermediate Similarity	NPC14227
0.6944	Remote Similarity	NPC477201
0.6875	Remote Similarity	NPC70387
0.6667	Remote Similarity	NPC155263
0.6579	Remote Similarity	NPC243532
0.6562	Remote Similarity	NPC207292
0.6486	Remote Similarity	NPC106851
0.6486	Remote Similarity	NPC282788
0.6486	Remote Similarity	NPC274927
0.641	Remote Similarity	NPC68343
0.641	Remote Similarity	NPC328089
0.6389	Remote Similarity	NPC487561
0.6389	Remote Similarity	NPC606120
0.6333	Remote Similarity	NPC180534
0.6333	Remote Similarity	NPC611531
0.6316	Remote Similarity	NPC179764
0.6296	Remote Similarity	NPC175342
0.6154	Remote Similarity	NPC251042
0.6154	Remote Similarity	NPC255863
0.6154	Remote Similarity	NPC473863
0.6154	Remote Similarity	NPC174447
0.6154	Remote Similarity	NPC136164
0.6154	Remote Similarity	NPC122521
0.6154	Remote Similarity	NPC245947
0.6	Remote Similarity	NPC318420
0.6	Remote Similarity	NPC326268
0.5946	Remote Similarity	NPC225929
0.5938	Remote Similarity	NPC34416
0.5926	Remote Similarity	NPC214610
0.5926	Remote Similarity	NPC118968
0.5926	Remote Similarity	NPC183424
0.5926	Remote Similarity	NPC294085
0.5882	Remote Similarity	NPC48162
0.5769	Remote Similarity	NPC174368
0.5758	Remote Similarity	NPC129972
0.5758	Remote Similarity	NPC8219
0.5758	Remote Similarity	NPC301528
0.5758	Remote Similarity	NPC71317
0.5758	Remote Similarity	NPC163746
0.5758	Remote Similarity	NPC103286
0.575	Remote Similarity	NPC323597
0.575	Remote Similarity	NPC211752
0.575	Remote Similarity	NPC318814
0.575	Remote Similarity	NPC320669
0.575	Remote Similarity	NPC323498
0.561	Remote Similarity	NPC317583
0.5588	Remote Similarity	NPC18712
0.5588	Remote Similarity	NPC74845
0.5556	Remote Similarity	NPC134782
0.5556	Remote Similarity	NPC268826
0.5476	Remote Similarity	NPC320642
0.5476	Remote Similarity	NPC329550
0.5455	Remote Similarity	NPC117572
0.5455	Remote Similarity	NPC262968
0.5429	Remote Similarity	NPC87394
0.5429	Remote Similarity	NPC324004
0.5429	Remote Similarity	NPC328497
0.5429	Remote Similarity	NPC602547
0.5405	Remote Similarity	NPC40082
0.5366	Remote Similarity	NPC187777
0.5349	Remote Similarity	NPC323045
0.5349	Remote Similarity	NPC49863
0.5349	Remote Similarity	NPC317881
0.5312	Remote Similarity	NPC55023
0.5312	Remote Similarity	NPC21844
0.5278	Remote Similarity	NPC174560
0.5278	Remote Similarity	NPC125312
0.525	Remote Similarity	NPC28205
0.5227	Remote Similarity	NPC322461
0.5161	Remote Similarity	NPC604140
0.5122	Remote Similarity	NPC274290
0.5111	Remote Similarity	NPC605544
0.5111	Remote Similarity	NPC607260

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC515911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6701
0.1-0.2	2161
0.2-0.3	217
0.3-0.4	43
0.4-0.5	9
0.5-0.6	8
0.6-0.7	2
0.7-0.8	5
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9259	High Similarity	NPD3195	Phase 2
0.9259	High Similarity	NPD3196	Approved
0.8621	High Similarity	NPD3173	Phase 4
0.8333	Intermediate Similarity	NPD4266	Phase 2
0.7353	Intermediate Similarity	NPD3194	Phase 4
0.7188	Intermediate Similarity	NPD3172	Approved
0.7037	Intermediate Similarity	NPD2270	Pre-clinical
0.7037	Intermediate Similarity	NPD633	Phase 3
0.7037	Intermediate Similarity	NPD9448	Phase 2
0.6842	Remote Similarity	NPD39	Phase 4
0.6333	Remote Similarity	NPD622	Pre-clinical
0.5926	Remote Similarity	NPD9655	Phase 4
0.5455	Remote Similarity	NPD28	Approved
0.5455	Remote Similarity	NPD29	Phase 4
0.5455	Remote Similarity	NPD4222	Phase 3
0.5429	Remote Similarity	NPD3197	Phase 1
0.5429	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5349	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5143	Remote Similarity	NPD3174	Discontinued

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