NPASS Compound

Structure

NPC255246 OpenBabel06302215122D 74 84 0 0 1 0 0 0 0 0999 V2000 4.1564 -0.2445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6564 -1.1105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6564 -1.1105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1564 -0.2445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6564 0.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6564 0.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1564 1.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6564 2.3536 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1564 3.2196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1564 3.2196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6564 4.0856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6564 4.0856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1564 3.2196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6564 2.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1564 1.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1564 1.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3436 2.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3436 2.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8436 1.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3436 0.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8436 -0.2445 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3679 -0.8096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0334 -1.5041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4677 -2.1410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2363 -2.0834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5708 -1.3889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1366 -0.7520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5708 -0.1151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3436 0.6215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0674 1.3115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8319 2.2833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5557 2.9733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5152 2.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7507 1.7195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0269 1.0296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7102 1.4376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2390 3.3813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8436 -0.2445 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8448 -1.4632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -0.4877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6895 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6895 0.9754 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8448 1.4632 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9754 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8448 1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 2.4386 0.0000 O 0 0 0 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 -0.8448 2.4386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5343 1.4632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5343 -0.4877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8436 1.4875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7997 -2.9096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0362 -1.5788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3436 0.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1564 -0.2445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1564 -0.2445 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6564 -1.1105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1564 -1.9766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6564 -2.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6564 -2.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1564 -1.9766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6564 -1.1105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1564 -1.9766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1564 -3.7086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6564 0.6215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6564 0.6215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1564 3.2196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6564 2.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1564 1.4875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1564 3.2196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1564 4.9516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6564 2.3536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1564 -0.2445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1564 -1.9766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 3 74 1 0 0 0 0 4 5 2 0 0 0 0 4 73 1 0 0 0 0 5 6 1 0 0 0 0 7 6 1 1 0 0 0 7 8 1 0 0 0 0 7 69 1 0 0 0 0 8 9 1 0 0 0 0 8 72 1 1 0 0 0 9 10 1 0 0 0 0 10 68 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 11 71 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 70 1 0 0 0 0 14 68 1 0 0 0 0 15 14 1 6 0 0 0 15 16 1 0 0 0 0 15 65 1 0 0 0 0 16 54 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 17 67 1 0 0 0 0 18 19 1 0 0 0 0 19 51 1 0 0 0 0 19 20 2 0 0 0 0 20 54 1 0 0 0 0 21 20 1 1 0 0 0 21 22 1 0 0 0 0 21 38 1 0 0 0 0 22 27 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 23 53 1 0 0 0 0 24 25 1 0 0 0 0 25 26 2 0 0 0 0 25 52 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 28 29 1 0 0 0 0 29 30 1 6 0 0 0 29 38 1 0 0 0 0 29 51 1 0 0 0 0 30 35 2 0 0 0 0 30 31 1 0 0 0 0 31 32 2 0 0 0 0 32 33 1 0 0 0 0 33 34 2 0 0 0 0 33 37 1 0 0 0 0 34 35 1 0 0 0 0 34 36 1 0 0 0 0 38 39 1 1 0 0 0 40 39 1 1 0 0 0 40 41 1 0 0 0 0 40 47 1 0 0 0 0 41 42 1 0 0 0 0 41 50 1 6 0 0 0 42 43 1 0 0 0 0 42 49 1 1 0 0 0 43 44 1 0 0 0 0 43 48 1 1 0 0 0 44 45 1 1 0 0 0 44 47 1 0 0 0 0 45 46 1 0 0 0 0 54 55 1 0 0 0 0 55 56 1 0 0 0 0 56 57 1 1 0 0 0 56 65 1 0 0 0 0 57 62 2 0 0 0 0 57 58 1 0 0 0 0 58 59 2 0 0 0 0 59 60 1 0 0 0 0 60 61 2 0 0 0 0 60 64 1 0 0 0 0 61 62 1 0 0 0 0 61 63 1 0 0 0 0 65 66 1 1 0 0 0 68 69 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1026.24
Volume:	951.25
LogP:	1.818
LogD:	0.898
LogS:	-4.307
# Rotatable Bonds:	7
TPSA:	399.29
# H-Bond Aceptor:	23
# H-Bond Donor:	17
# Rings:	11
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.102
Synthetic Accessibility Score:	6.975
Fsp3:	0.294
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.134
MDCK Permeability:	1.5295632920242497e-06
Pgp-inhibitor:	0.624
Pgp-substrate:	0.329
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.795
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	84.11910247802734%
Volume Distribution (VD):	0.061
Pgp-substrate:	18.671356201171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	5.609
Half-life (T1/2):	0.321

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.239
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.286
Rat Oral Acute Toxicity:	0.687
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.967
Carcinogencity:	0.087
Eye Corrosion:	0.003
Eye Irritation:	0.917
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC255246

Natural Product ID:	NPC255246
*Common Name:**	XIFRPUIQXADIQI-QAMMNMFASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XIFRPUIQXADIQI-QAMMNMFASA-N
Standard InCHI:	InChI=1S/C51H46O23/c52-15-34-41(65)43(67)44(68)50(69-34)72-49-40-35-28(61)10-19(53)11-32(35)73-51(49,18-3-6-23(56)27(60)9-18)74-33-14-30(63)37-39(42(66)46(71-48(37)38(33)40)17-2-5-22(55)26(59)8-17)36-29(62)13-24(57)20-12-31(64)45(70-47(20)36)16-1-4-21(54)25(58)7-16/h1-11,13-14,31,34,39-46,49-50,52-68H,12,15H2/t31-,34-,39+,40-,41+,42-,43+,44-,45-,46-,49-,50+,51+/m1/s1
SMILES:	c1cc(c(cc1[C@@H]1[C@@H](Cc2c(cc(c([C@H]3c4c(cc5c([C@H]6c7c(cc(cc7O[C@](c7ccc(c(c7)O)O)([C@@H]6O[C@H]6[C@@H]([C@H]([C@H]([C@@H](CO)O6)O)O)O)O5)O)O)c4O[C@H](c4ccc(c(c4)O)O)[C@@H]3O)O)c2O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)00169-2]
NPO4654	Critonia quadrangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)81431-4]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575960]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11975485]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15128023]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21446699]
NPO16601	Styrax perkinsiae	Species	Styracaceae	Eukaryota	n.a.	bark	n.a.	PMID[26762060]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31763840]
NPO12697	Baccharis megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3437280]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9748368]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16289	Marrubium supinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15760	Aconitum pseudohuiliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14413	Bombus muscorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18873.8	Salmonella enterica subsp. enterica serovar typhimurium	Subspecies	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14723	Streptomyces xantholiticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15531	Quercus dentata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12438	Fomes cajanderi	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7515	Codium decorticatum	Species	Codiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10802	Rhinoceros sondaicus	Species	Rhinocerotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29175	Strychnos tabascana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14892	Flemingia congesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11233	Pseudocyphellaria impressa	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4448	Relhania pumila	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16435	Cacalia bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13872	Amanita cokeri	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14046	Stevia mercedensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24501	Asteriscus graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9823	Centrosema pascuorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11915	Lecanora planaica	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26436	Citrus glauca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13563	Alstonia deplanchei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16856	Solanum elaeagnifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15969	Alcyonium molle	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16601	Styrax perkinsiae	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9107	Metalasia bolusii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO576	Oxyanthus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4654	Critonia quadrangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12697	Baccharis megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21913	Verbesina rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14572	Senecio latifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13396	Aplophyllum popovii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16522	Ceratozamia fuscoviridis	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15760	Aconitum pseudohuiliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5468	Dacrydium fonki	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2372	Cryptotermes cynocephalus	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16766	Haplophyllum dauricum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16289	Marrubium supinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16071	Erigeron crispus	Species	Asteraceae	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 NPC255246 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	551
0.1-0.2	1862
0.2-0.3	4983
0.3-0.4	10709
0.4-0.5	7443
0.5-0.6	5058
0.6-0.7	7112
0.7-0.8	4165
0.8-0.85	629
0.85-0.9	138
0.9-0.95	28
0.95-1	19

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 NPC255246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	909
0.2-0.3	2078
0.3-0.4	2785
0.4-0.5	1580
0.5-0.6	936
0.6-0.7	373
0.7-0.8	61
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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