NPASS Compound

Structure

NPC325092 OpenBabel06302215272D 86 88 0 0 1 0 0 0 0 0999 V2000 -18.2381 20.2360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.2381 19.2472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3818 18.7528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3818 17.7641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.5255 17.2697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.5255 16.2809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.6692 15.7865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.6692 14.7978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.8129 14.3034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.8129 13.3146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9566 12.8202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9566 11.8315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1003 11.3371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1003 10.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2440 9.8539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2440 8.8652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3877 8.3708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3877 7.3820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5314 6.8877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5314 5.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6752 5.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6752 4.4157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8189 3.9214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5314 3.9214 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.5314 2.9326 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.6752 2.4382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8189 2.9326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9626 2.4382 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.1063 2.9326 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.2500 2.4382 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.2500 1.4495 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.1063 0.9551 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.9626 1.4495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1063 -0.0337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2500 -0.5281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3937 0.9551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5374 1.4495 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.6811 0.9551 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.8248 1.4495 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.8248 2.4382 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.6811 2.9326 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.5374 2.4382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6811 3.9214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8248 4.4157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9685 2.9326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1122 0.4607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2559 0.9551 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4433 1.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3983 1.3983 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6542 0.4433 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9551 -0.2559 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2110 -1.2110 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5118 -1.9101 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.4433 -1.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6992 -0.6992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7677 -2.8652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1661 -1.4669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6093 0.1873 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3085 0.8865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2635 0.6306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0526 1.8416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0975 2.0975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3850 1.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3995 2.5373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2985 2.3138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6811 -0.0337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3937 2.9326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1063 3.9214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3877 2.4382 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -11.3877 1.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5314 0.9551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5314 -0.0337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6752 -0.5281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6752 -1.5168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8189 -2.0112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8189 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9626 -3.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9626 -4.4831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1063 -4.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1063 -5.9663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2500 -6.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2500 -7.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3937 -7.9438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3937 -8.9326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2440 2.9326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 25 70 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 28 33 1 0 0 0 0 28 29 1 0 0 0 0 29 30 1 0 0 0 0 29 69 1 0 0 0 0 30 31 1 0 0 0 0 30 68 1 0 0 0 0 31 32 1 0 0 0 0 31 36 1 0 0 0 0 32 33 1 0 0 0 0 32 34 1 0 0 0 0 34 35 1 0 0 0 0 36 37 1 0 0 0 0 37 42 1 0 0 0 0 37 38 1 0 0 0 0 38 39 1 0 0 0 0 38 67 1 0 0 0 0 39 40 1 0 0 0 0 39 46 1 0 0 0 0 40 41 1 0 0 0 0 40 45 1 0 0 0 0 41 42 1 0 0 0 0 41 43 1 0 0 0 0 43 44 1 0 0 0 0 46 47 1 0 0 0 0 47 52 1 0 0 0 0 47 48 1 0 0 0 0 47 64 1 0 0 0 0 48 49 1 0 0 0 0 49 50 1 0 0 0 0 49 63 1 0 0 0 0 50 51 1 0 0 0 0 50 59 1 0 0 0 0 51 52 1 0 0 0 0 51 53 1 0 0 0 0 53 54 1 0 0 0 0 53 58 1 0 0 0 0 54 55 1 0 0 0 0 54 57 1 0 0 0 0 55 56 1 0 0 0 0 59 60 1 0 0 0 0 60 61 2 0 0 0 0 60 62 1 0 0 0 0 64 65 2 0 0 0 0 64 66 1 0 0 0 0 70 71 1 0 0 0 0 70 86 1 0 0 0 0 71 72 2 3 0 0 0 72 73 1 0 0 0 0 73 74 1 0 0 0 0 74 75 1 0 0 0 0 75 76 1 0 0 0 0 76 77 1 0 0 0 0 77 78 1 0 0 0 0 78 79 1 0 0 0 0 79 80 1 0 0 0 0 80 81 1 0 0 0 0 81 82 1 0 0 0 0 82 83 1 0 0 0 0 83 84 1 0 0 0 0 84 85 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1236.81
Volume:	1268.577
LogP:	6.11
LogD:	4.046
LogS:	-2.191
# Rotatable Bonds:	51
TPSA:	373.41
# H-Bond Aceptor:	23
# H-Bond Donor:	14
# Rings:	3
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.029
Synthetic Accessibility Score:	6.481
Fsp3:	0.921
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.843
MDCK Permeability:	2.552457772253547e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	96.6403579711914%
Volume Distribution (VD):	0.048
Pgp-substrate:	6.633835315704346%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.804
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.041
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.009

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC325092

Natural Product ID:	NPC325092
*Common Name:**	KTKHFEPBOUGPQO-JOQHOESCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KTKHFEPBOUGPQO-JOQHOESCSA-N
Standard InCHI:	InChI=1S/C63H116N2O21/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-37-50(73)65-44(45(70)36-34-32-30-28-26-24-17-15-13-11-9-7-5-2)42-81-60-55(77)54(76)57(49(41-68)83-60)84-61-56(78)59(53(75)48(40-67)82-61)86-63(62(79)80)38-46(71)51(64-43(3)69)58(85-63)52(74)47(72)39-66/h34,36,44-49,51-61,66-68,70-72,74-78H,4-33,35,37-42H2,1-3H3,(H,64,69)(H,65,73)(H,79,80)/b36-34+/t44-,45+,46-,47+,48+,49+,51+,52+,53-,54+,55+,56+,57+,58+,59-,60+,61-,63-/m0/s1
SMILES:	CCCCCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)OC3(CC(C(C(O3)C(C(CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)C(C=CCCCCCCCCCCCCC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90659796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000257] Sphingolipids [CHEMONTID:0003258] Glycosphingolipids [CHEMONTID:0001439] Gangliosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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	NP ID	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC325092 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score	Similarity Level	Natural Product ID

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC325092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score	Similarity Level	Drug ID	Developmental Stage

Bioactivity similarity: Similar Natural Products in NPASS

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