NPASS Compound

Natural Product: NPC177818

Natural Product ID	NPC177818
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ruscogenin
IUPAC Name	n.a.
Synonyms	Ruscogenin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1169820
PubChem CID	441893
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 73 78 0 0 0 0 0 0 0 0999 V2000 7.6127 1.0798 -1.5028 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4521 0.6089 -0.6919 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3716 -0.8862 -0.5739 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0536 -1.4101 -0.1747 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9056 -0.4958 -0.2350 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1857 0.8422 -0.2899 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1201 1.0602 -1.3052 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0092 -0.7815 -1.2863 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9781 0.0885 -1.0522 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8234 0.1973 0.4730 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9334 -0.6806 0.9460 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5528 -0.2510 2.2401 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4526 -0.2961 0.7669 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2680 0.0532 -0.4927 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6296 -0.4585 -1.5489 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6771 -0.4370 -0.4970 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3327 -0.2643 -1.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7583 -0.6599 -1.7151 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4208 -0.4534 -0.5958 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8588 0.1639 0.6290 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3907 0.3719 0.5705 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7215 0.1643 1.9181 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2475 0.4260 1.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3053 -0.6861 1.7986 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6192 1.4879 0.7941 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0922 1.6529 2.0840 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7397 1.6413 -0.1708 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6210 0.4522 -0.3563 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8532 -0.8517 -0.5485 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6130 0.3512 0.6117 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4524 -1.7608 1.0913 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3175 1.3327 -2.5576 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9548 2.0640 -1.0726 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4949 0.4207 -1.4571 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4823 1.0493 0.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7218 -1.3045 -1.5615 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1806 -1.1927 0.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1325 -1.8343 0.8644 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8252 -2.3081 -0.8206 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8732 0.3666 -2.1548 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1670 2.1055 -1.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1528 1.1147 -1.4534 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9750 1.2282 0.8214 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6965 -1.7595 0.9506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8276 0.2133 2.9410 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9091 -1.1861 2.7635 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4714 0.3634 2.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2987 1.1624 -0.5618 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4761 0.0313 -2.5425 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6546 -1.5391 -1.6745 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7852 -1.5005 -0.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8550 -0.9994 -2.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2053 0.7467 -2.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2933 -1.1302 -2.5557 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2068 1.4464 0.3072 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1676 0.8998 2.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9673 -0.8434 2.2930 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0267 1.5042 1.8337 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1755 0.0476 2.8429 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8705 -0.3469 2.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4012 -0.5696 1.9308 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0743 -1.7532 1.6827 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9056 2.3337 0.6119 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9020 2.5697 2.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4016 2.4598 0.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4031 2.0519 -1.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1511 0.6163 -1.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1618 -1.3924 -1.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0018 -1.5683 0.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7194 1.2207 1.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9997 -1.8594 2.0753 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5722 -2.1268 1.3104 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8682 -2.4027 0.3138 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 6 6 7 1 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 20 24 1 1 20 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 13 31 1 1 7 2 1 0 15 9 1 0 21 16 1 0 11 5 1 0 23 13 1 0 29 19 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 1 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 7 40 1 0 7 41 1 0 9 42 1 6 10 43 1 1 11 44 1 1 12 45 1 0 12 46 1 0 12 47 1 0 14 48 1 6 15 49 1 0 15 50 1 0 16 51 1 1 17 52 1 0 17 53 1 0 18 54 1 0 21 55 1 6 22 56 1 0 22 57 1 0 23 58 1 0 23 59 1 0 24 60 1 0 24 61 1 0 24 62 1 0 25 63 1 6 26 64 1 0 27 65 1 0 27 66 1 0 28 67 1 6 29 68 1 0 29 69 1 0 30 70 1 0 31 71 1 0 31 72 1 0 31 73 1 0 M END

Standard InCHIKey	QMQIQBOGXYYATH-IDABPMKMSA-N
Standard InCHI	InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
SMILES	C[C@@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)[C@H](O)C[C@@H](C3)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	430.31	Volume:	456.734 ? Van der Waals volume.
Dense:	0.942	LogP:	5.044 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.272 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.318 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	30.0
TPSA:	58.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.548	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.453	Fsp³:	0.926
MCE-18:	140.885 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.719	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.196	Promiscuous compounds:	0.246

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.164	MDCK Permeability:	-4.964
Pgp-inhibitor:	0.024	Pgp-substrate:	0.96
PAMPA:	0.83 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.151	30% Bioavailability (F30%):	0.176
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.51	MRP1:	0.318
Plasma Protein Binding (PPB):	93.001%	Volume Distribution (VD):	0.461
Fu:	9.113% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.984
BSEP inhibitor:	0.968

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.98	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.948
HLM stability:	0.533 ? 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):

15.564

Half-life (T1/2):

2.326

ADMET: Toxicity

hERG Blockers:	0.166	hERG Blockers (10um):	0.335
Human Hepatotoxicity (H-HT):	0.577	Drug-induced Liver Injury (DILI):	0.624
AMES Toxicity:	0.18	Rat Oral Acute Toxicity:	0.345
Maximum Recommended Daily Dose:	0.969	Skin Sensitization:	0.987
Carcinogencity:	0.852	Eye Corrosion:	0.009
Eye Irritation:	0.297	Respiratory Toxicity:	0.25
Drug-induced Neurotoxicity:	0.08	Ototoxicity:	0.825
Hematotoxicity:	0.024	Drug-induced Nephrotoxicity:	0.603
Genotoxicity:	0.046	RPMI-8226 Immunitoxicity:	0.128
A549 Cytotoxicity:	0.154	Hek293 Cytotoxicity:	0.742
BCF:	1.547 ? 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:	3.483 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.799 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.211 ? 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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO25265	Sophora secundiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)78784-3]
NPO26956	Crambe crambe	Species	Esperiopsidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00019a049]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11325235]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[14575439]
NPO26173	Anomospermum grandifolium	Species	Menispermaceae	Eukaryota	Stems	n.a.	n.a.	PMID[14695805]
NPO26683	Dichomitus squalens	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620268]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO24757	Meryta denhamii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18442289]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18547115]
NPO24883	Angiopteris caudatiformis	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19371069]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	roots	n.a.	n.a.	PMID[20346658]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20581114]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23439553]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25515814]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36014413]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	Underground parts	n.a.	n.a.	PMID[9784168]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	tuber	n.a.	Database[Article]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5275	Liriope muscari	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24375	Micrococcus luteus	Species	Micrococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24883	Angiopteris caudatiformis	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20000	Adina rubescens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29139	Agave huachucensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12552	Aloe indica	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26173	Anomospermum grandifolium	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26489	Arthrobacter viscosus	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24150	Baptisia lecontii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23463	Basanacantha spinosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25729	Centaurea aemulans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18404	Clarkia unguiculata	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26577	Clinostemon mahuba	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26956	Crambe crambe	Species	Esperiopsidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26020	Dahlstedtia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26693	Daphne papyracea	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26683	Dichomitus squalens	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26915	Erinus alpinus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25210	Fulmarus glacialis	Species	Procellariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27000	Geranium macrorrhizum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26222	Gonepteryx rhamni	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23068	Guettarda eximia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25025	Gypothamnium pinifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26843	Heliconius cydno	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26427	Heterocapsa triquetra	Species	Heterocapsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23570	Hypolaena fastigiata	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26106	Lactarius pubescens	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27053	Maclura aurantiaca	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24757	Meryta denhamii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26444	Mimosa invisa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26467	Nipaecoccus aurilanatus	Species	Pseudococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25592	Pedicularis densispica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26300	Penianthus zenkeri	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26862	Pentaceraster alveolatus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24594	Polypodium hastatum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24509	Randia longispina	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27027	Renilla muelleri	Species	Renillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27038	Senecio macrophyllus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25843	Solanum chacoense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25265	Sophora secundiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2096	Stenostomum acutatum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26793	Trichia carnea	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25783	Tulipa silvestris	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25438	Xiphophora gladiata	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25843	Solanum chacoense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25843	Solanum chacoense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5275	Liriope muscari	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26915	Erinus alpinus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5275	Liriope muscari	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25592	Pedicularis densispica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26173	Anomospermum grandifolium	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23570	Hypolaena fastigiata	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26683	Dichomitus squalens	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26300	Penianthus zenkeri	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12552	Aloe indica	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26793	Trichia carnea	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26222	Gonepteryx rhamni	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26956	Crambe crambe	Species	Esperiopsidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27000	Geranium macrorrhizum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25843	Solanum chacoense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26843	Heliconius cydno	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26577	Clinostemon mahuba	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25438	Xiphophora gladiata	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20000	Adina rubescens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26020	Dahlstedtia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2096	Stenostomum acutatum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25210	Fulmarus glacialis	Species	Procellariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24883	Angiopteris caudatiformis	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24757	Meryta denhamii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26467	Nipaecoccus aurilanatus	Species	Pseudococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26444	Mimosa invisa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23068	Guettarda eximia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24594	Polypodium hastatum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25783	Tulipa silvestris	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24375	Micrococcus luteus	Species	Micrococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27027	Renilla muelleri	Species	Renillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26106	Lactarius pubescens	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25729	Centaurea aemulans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26427	Heterocapsa triquetra	Species	Heterocapsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18404	Clarkia unguiculata	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24509	Randia longispina	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25265	Sophora secundiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24150	Baptisia lecontii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23463	Basanacantha spinosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27038	Senecio macrophyllus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27053	Maclura aurantiaca	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25025	Gypothamnium pinifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26862	Pentaceraster alveolatus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26693	Daphne papyracea	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26489	Arthrobacter viscosus	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29139	Agave huachucensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26915	Erinus alpinus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5275	Liriope muscari	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell line	3

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
NPT1970	Cell line	THP-1	Homo sapiens	IC50	=	2270.0	nM	PMID[20561785]
NPT1312	Cell line	SW1990	Homo sapiens	IC50	=	8140.0	nM	PMID[36332549]
NPT1081	Cell line	BXPC-3	Homo sapiens	IC50	=	7320.0	nM	PMID[36332549]

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 NPC177818 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	22875
0.1-0.2	24560
0.2-0.3	2122
0.3-0.4	174
0.4-0.5	96
0.5-0.6	21
0.6-0.7	2
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8209	Intermediate Similarity	NPC176406
0.75	Intermediate Similarity	NPC235126
0.75	Intermediate Similarity	NPC242419
0.6901	Remote Similarity	NPC474022
0.6575	Remote Similarity	NPC486119
0.5921	Remote Similarity	NPC100451
0.5795	Remote Similarity	NPC306131
0.5795	Remote Similarity	NPC200802
0.5775	Remote Similarity	NPC248944
0.5775	Remote Similarity	NPC7479
0.5775	Remote Similarity	NPC257296
0.5733	Remote Similarity	NPC474015
0.5694	Remote Similarity	NPC296734
0.5647	Remote Similarity	NPC181845
0.5556	Remote Similarity	NPC227260
0.5543	Remote Similarity	NPC70204
0.5479	Remote Similarity	NPC273290
0.5479	Remote Similarity	NPC232044
0.5467	Remote Similarity	NPC187159
0.5375	Remote Similarity	NPC482599
0.5263	Remote Similarity	NPC305808
0.5227	Remote Similarity	NPC13190
0.5205	Remote Similarity	NPC24556
0.5106	Remote Similarity	NPC470432
0.5106	Remote Similarity	NPC230507
0.51	Remote Similarity	NPC294129

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC177818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7386
0.1-0.2	1635
0.2-0.3	120
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
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
0.5775	Remote Similarity	NPD6928	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data