NPASS Compound

Natural Product: NPC162168

Natural Product ID	NPC162168
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IWSKYCJOAZZKEJ-OFFVNLDOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101357917
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 58 60 0 0 0 0 0 0 0 0999 V2000 1.6122 2.9012 -0.1905 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5420 1.8605 -0.1745 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0966 1.7295 1.2160 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3599 0.8852 0.9379 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8937 -0.4687 0.5324 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8559 -1.5857 0.6597 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2760 -1.1816 0.9944 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4738 -2.5499 1.8011 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9326 -2.4627 -0.5704 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5860 -2.9081 -1.0508 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4783 -1.8545 -0.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1062 -0.4568 -0.7657 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8409 -0.0522 -1.9734 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0795 0.4755 -0.4962 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0798 0.4749 -1.5799 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3794 0.1769 -0.8854 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0488 -0.1063 0.5284 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9522 -0.4035 1.4807 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3597 -0.4670 1.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1760 -0.7444 2.0701 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8124 -0.2270 -0.1085 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6835 -0.0095 0.6725 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1557 1.5773 0.0362 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3654 2.1267 0.4089 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7268 1.9811 1.6054 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2433 2.8714 -0.5331 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2415 3.7594 0.4369 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 3.3114 -1.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5654 2.5579 0.2590 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2377 2.1106 -0.9072 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3478 2.6988 1.6403 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5449 1.0921 1.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8622 0.8285 1.9122 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0651 -0.6913 1.2887 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2951 -0.6805 1.9646 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8279 -2.1620 1.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7952 -0.7022 0.1692 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8876 -3.5428 1.6188 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3684 -2.5174 1.8840 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8524 -2.0661 2.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4969 -3.3864 -0.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5534 -1.9670 -1.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2924 -3.8259 -0.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6853 -3.2080 -2.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0575 -2.0529 0.0161 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1700 -1.9594 -1.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7803 -0.8692 -2.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2944 0.8049 -2.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8713 0.2677 -1.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8718 -0.1853 -2.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1662 1.5042 -2.0403 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0545 1.0759 -0.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8861 -0.7034 -1.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5767 -0.5896 2.4778 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7687 0.1495 -0.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6815 3.2344 -1.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1620 2.3276 -0.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5588 3.8043 0.0100 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 6 8 1 0 6 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 17 22 1 0 4 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 14 2 1 0 12 5 1 0 14 22 1 1 1 27 1 0 1 28 1 0 1 29 1 0 2 30 1 6 3 31 1 0 3 32 1 0 4 33 1 1 5 34 1 1 7 35 1 0 7 36 1 0 7 37 1 0 8 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 9 42 1 0 10 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 13 47 1 0 13 48 1 0 13 49 1 0 15 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 18 54 1 0 21 55 1 0 26 56 1 0 26 57 1 0 26 58 1 0 M END

Standard InCHIKey	IWSKYCJOAZZKEJ-OFFVNLDOSA-N
Standard InCHI	InChI=1S/C21H32O5/c1-13-11-16(25-14(2)22)18-19(3,4)8-6-9-20(18,5)21(13)10-7-15(26-21)12-17(23)24/h12-13,16,18H,6-11H2,1-5H3,(H,23,24)/b15-12+/t13-,16-,18+,20+,21-/m1/s1
SMILES	C[C@@H]1C[C@H]([C@H]2C(C)(C)CCC[C@]2(C)[C@]21CC/C(=CC(=O)O)/O2)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	364.22	Volume:	382.145 ? Van der Waals volume.
Dense:	0.953	LogP:	2.491 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.247 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.553 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	19.0
TPSA:	72.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.584	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.107	Fsp³:	0.81
MCE-18:	87.158 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.091	Fluc inhibitor:	0.005 ? 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:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.424	Promiscuous compounds:	0.716

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.199	MDCK Permeability:	-4.903
Pgp-inhibitor:	0.14	Pgp-substrate:	0.003
PAMPA:	0.861 ? 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):	0.001
20% Bioavailability (F20%):	0.03	30% Bioavailability (F30%):	0.037
50% Bioavailability (F50%):	0.142

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.991
Plasma Protein Binding (PPB):	93.061%	Volume Distribution (VD):	-0.614
Fu:	7.337% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.959	BCRP inhibitor:	0.001
BSEP inhibitor:	0.971

ADMET: Metabolism

CYP1A2-inhibitor:	0.254	CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.182	CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.087	CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.534	CYP3A4-substrate:	0.027
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.958
HLM stability:	0.915 ? 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):

2.775

Half-life (T1/2):

1.025

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.061
Human Hepatotoxicity (H-HT):	0.606	Drug-induced Liver Injury (DILI):	0.819
AMES Toxicity:	0.211	Rat Oral Acute Toxicity:	0.352
Maximum Recommended Daily Dose:	0.294	Skin Sensitization:	0.979
Carcinogencity:	0.636	Eye Corrosion:	0.861
Eye Irritation:	0.945	Respiratory Toxicity:	0.518
Drug-induced Neurotoxicity:	0.102	Ototoxicity:	0.377
Hematotoxicity:	0.444	Drug-induced Nephrotoxicity:	0.848
Genotoxicity:	0.66	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.023	Hek293 Cytotoxicity:	0.065
BCF:	0.648 ? 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:	3.527 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.164 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.419 ? 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
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180830]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	leaves	Tam Kim, Cao Bang Province, in North Vietnam	2000-JUN	PMID[16989521]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	whole plant	Cholistan desert near district Bahawalpur (Punjab), Pakistan	2003-Oct	PMID[20542692]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[2082684]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21922656]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO18530	Shigella flexneri	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26918643]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3254039]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3256207]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3668556]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21298	Leucanthemum maximum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22582	Smenospongia echina	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21798	Dacrydium biforme	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20536	Salvia nubicola	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18571	Drypetes roxburghii	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7080	Monascus purpureus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21875	Persea indica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7865	Scapania nemorea	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20678	Grindelia nana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14394	Hakea saligna	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16146	Osmundaria colensoi	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17108	Lecanora lividocinerea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20184	Streptomyces misawanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22762	Eremophila serrulata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22994	Cordyline indivisa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21875	Persea indica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21998	Corydalis cornuta	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22940	Delphinium campylocentrum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18571	Drypetes roxburghii	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19074	Buddleja variabilis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16146	Osmundaria colensoi	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21798	Dacrydium biforme	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7865	Scapania nemorea	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21875	Persea indica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14394	Hakea saligna	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22323	Pinus picea	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12225	Amsinckia menziesii	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23057	Primula hirsuta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21113	Coronophora gregaria	Species	Nitschkiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20043	Vallaris solanacea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18530	Shigella flexneri	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23135	Formica fusca	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21298	Leucanthemum maximum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20808	Halopitys incurvus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20536	Salvia nubicola	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21736	Abies nobilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5952	Phegopteris bukoensis	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19921	Polyphaga sinensis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23178	Jasminum grandiflorum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20360	Mentha pulegiformis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22454	Picris radicata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20678	Grindelia nana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20184	Streptomyces misawanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21636	Didemnum inarmatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17108	Lecanora lividocinerea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22762	Eremophila serrulata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22994	Cordyline indivisa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22710	Acrocomia sclerocarpa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21505	Calea megacephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22062	Leptothorax acervorum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22582	Smenospongia echina	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22248	Alkanna hirsutissima	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14247	Melaleuca uncinata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22188	Piper aequale	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7080	Monascus purpureus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21247	Nephroma australe	Species	Nephromataceae	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 NPC162168 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	23879
0.1-0.2	24556
0.2-0.3	1382
0.3-0.4	34
0.4-0.5	5
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.5818	Remote Similarity	NPC109510
0.5469	Remote Similarity	NPC170633

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC162168 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5908
0.1-0.2	3209
0.2-0.3	33
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

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