NPASS Compound

Natural Product: NPC94101

Natural Product ID	NPC94101
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RJEUVXAJCYTMIC-LRFNUQPTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21626351
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 85 91 0 0 0 0 0 0 0 0999 V2000 7.7902 -1.3334 0.1397 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9808 -0.3913 -0.6777 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5212 0.4429 -1.4470 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6028 -0.4211 -0.6009 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7335 0.4266 -1.3302 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8925 -0.3030 -2.3254 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4312 -0.3635 -2.0181 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1599 -0.4636 -0.5050 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8175 -1.6989 -0.0452 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6625 0.8245 0.0702 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4408 0.8029 1.5513 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9446 0.9159 1.7845 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1603 -0.1176 1.0326 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2840 -1.3899 1.8774 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6588 -0.4166 -0.3424 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0542 -1.6122 -0.8659 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4231 -1.7714 -0.5519 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0831 -0.8834 0.4456 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5208 -0.6856 0.2301 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0670 0.2000 -0.7730 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5880 -0.0388 -0.8102 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9391 -0.7582 -2.0921 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3611 1.2632 -0.8104 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0572 -0.8436 0.3645 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4494 -0.3830 1.6638 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9803 -0.3359 1.6554 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3607 0.9686 2.0710 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8832 0.7685 2.2121 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2880 0.3023 0.8737 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3592 1.4850 -0.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2690 -1.4035 2.3674 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6195 -1.9419 3.4394 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1571 -1.6995 1.6452 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1512 -1.3373 -1.8364 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0012 1.2867 -0.3682 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9714 2.7023 -0.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8826 1.4495 0.8802 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5340 -1.7950 -0.5437 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1446 -2.1219 0.5299 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2727 -0.8146 0.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4356 1.0789 -1.9321 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9720 0.1567 -3.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3451 -1.3274 -2.4748 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9971 -1.3170 -2.4375 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8577 0.4725 -2.4165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0836 -2.5286 0.1178 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5077 -2.1634 -0.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4340 -1.6110 0.8653 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9432 1.6217 -0.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8837 1.7204 1.9903 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8829 -0.0533 2.0707 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8110 0.7388 2.8945 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6534 1.9517 1.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3866 -1.4377 2.1319 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2076 -1.2894 2.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0584 -2.3023 1.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3888 0.4428 -1.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5292 -2.5218 -1.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8616 -2.8160 -0.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9644 -1.7170 0.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9577 1.2725 -0.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6471 -0.0628 -1.7706 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9423 -0.4035 -2.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8980 -1.8444 -2.0179 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2048 -0.4257 -2.8574 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6029 2.0683 -0.5831 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0898 1.3186 0.0228 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7966 1.5165 -1.7764 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1658 -0.6420 0.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9856 -1.9383 0.2158 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9460 0.5763 1.9727 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7771 -1.1249 2.4441 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6805 1.8079 1.4621 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7468 1.1811 3.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7082 0.0685 3.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4004 1.7383 2.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0538 2.2935 0.3489 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5989 1.2236 -1.0941 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3937 2.0645 -0.1118 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7204 2.6495 -2.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9604 3.1553 -0.8956 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1675 3.3068 -0.5101 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6606 2.4462 1.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7464 0.6151 1.5851 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9283 1.5267 0.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 26 25 1 6 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 26 31 1 0 31 32 2 0 31 33 1 0 17 34 1 0 10 35 1 0 35 36 1 0 35 37 1 0 35 5 1 0 15 8 1 0 34 16 1 0 29 13 1 0 29 18 1 0 18 33 1 1 26 19 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 6 6 42 1 0 6 43 1 0 7 44 1 0 7 45 1 0 9 46 1 0 9 47 1 0 9 48 1 0 10 49 1 6 11 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 14 54 1 0 14 55 1 0 14 56 1 0 15 57 1 6 16 58 1 6 17 59 1 6 19 60 1 6 20 61 1 0 20 62 1 0 22 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 27 74 1 0 28 75 1 0 28 76 1 0 30 77 1 0 30 78 1 0 30 79 1 0 36 80 1 0 36 81 1 0 36 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 M END

Standard InCHIKey	RJEUVXAJCYTMIC-LRFNUQPTSA-N
Standard InCHI	InChI=1S/C32H48O5/c1-18(33)35-21-10-11-28(6)19(27(21,4)5)9-12-29(7)23(28)22-24(36-22)32-20-17-26(2,3)13-15-31(20,25(34)37-32)16-14-30(29,32)8/h19-24H,9-17H2,1-8H3/t19-,20+,21-,22-,23+,24-,28-,29+,30-,31-,32+/m0/s1
SMILES	CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2[C@H]2[C@@H]([C@]45[C@@H]6CC(C)(C)CC[C@@]6(CC[C@@]34C)C(=O)O5)O2)C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.35	Volume:	540.811 ? Van der Waals volume.
Dense:	0.947	LogP:	2.94 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.994 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.236 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	33.0
TPSA:	65.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	7.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.298	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.38	Fsp³:	0.938
MCE-18:	185.484 ? 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:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.862	Fluc inhibitor:	0.001 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.347	Promiscuous compounds:	0.269

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.02	MDCK Permeability:	-4.867
Pgp-inhibitor:	0.999	Pgp-substrate:	0.002
PAMPA:	0.261 ? 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):	0.003
20% Bioavailability (F20%):	0.808	30% Bioavailability (F30%):	0.771
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052	MRP1:	0.453
Plasma Protein Binding (PPB):	92.927%	Volume Distribution (VD):	0.368
Fu:	7.941% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.511
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.013	CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.737
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.938 ? 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):

7.646

Half-life (T1/2):

0.564

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.183
Human Hepatotoxicity (H-HT):	0.547	Drug-induced Liver Injury (DILI):	0.49
AMES Toxicity:	0.859	Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.399	Skin Sensitization:	1.0
Carcinogencity:	0.837	Eye Corrosion:	0.03
Eye Irritation:	0.58	Respiratory Toxicity:	0.259
Drug-induced Neurotoxicity:	0.131	Ototoxicity:	0.519
Hematotoxicity:	0.818	Drug-induced Nephrotoxicity:	0.864
Genotoxicity:	0.71	RPMI-8226 Immunitoxicity:	0.096
A549 Cytotoxicity:	0.613	Hek293 Cytotoxicity:	0.642
BCF:	2.583 ? 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:	4.858 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.053 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.94 ? 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
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[10661881]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430011]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	stems	n.a.	n.a.	PMID[12350169]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387673]
NPO27636	Hippasteria phrygiana	Species	Goniasteridae	Eukaryota	n.a.	pacific	n.a.	PMID[16252922]
NPO27230	Eysenhardtia platycarpa	Species	Fabaceae	Eukaryota	n.a.	branch	n.a.	PMID[17190443]
NPO27230	Eysenhardtia platycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190443]
NPO27449	Halichondria okadai	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21410164]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[28294414]
NPO16125	Micromonas pusilla	Species	Mamiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15349	Acacia sparsiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14936	Agave shawii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15205	Alaria crispa	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9479	Ambrosia grayi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13139	Anatheca montagnei	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14807	Arenaria juncea	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5866	Bitis arietans	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14463	Dirca occidentalis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15797	Drypetes littoralis	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13442	Eucalyptus regnans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12293	Euphorbia iberica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24409	Evasterias troschelii	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5047	Evodiopanax innovans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO820	Grindelia perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12490	Lecidea speirodes	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2038	Myrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14313	Pachybasium candidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16718	Pinna nobilis	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16475	Plumbago pulchella	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2827	Plumeria alba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16557	Polygala ruwenzoriensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8804	Raputia simulans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20219	Rhizobium etli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27733	Rosa hybrid cultivar	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16796	Rumex conglomeratus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4589	Sarcotragus spinosulus	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15588	Senecio desfontainei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16025	Werneria decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6740	Amycolatopsis sulphurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27230	Eysenhardtia platycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9137	Tasmannia lanceolata	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27636	Hippasteria phrygiana	Species	Goniasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27794	Acritopappus longifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27837	Sarracenia flava	Species	Sarraceniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29258	Virola oleifera	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27340	Campylopus clavatus	Species	Leucobryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27594	Viola odorata	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27837	Sarracenia flava	Species	Sarraceniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27837	Sarracenia flava	Species	Sarraceniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27837	Sarracenia flava	Species	Sarraceniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16125	Micromonas pusilla	Species	Mamiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13139	Anatheca montagnei	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27173	Ramalina pollinaria	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14936	Agave shawii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4589	Sarcotragus spinosulus	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9479	Ambrosia grayi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15797	Drypetes littoralis	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16718	Pinna nobilis	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29258	Virola oleifera	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6740	Amycolatopsis sulphurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16557	Polygala ruwenzoriensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16796	Rumex conglomeratus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15588	Senecio desfontainei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27837	Sarracenia flava	Species	Sarraceniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14463	Dirca occidentalis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5866	Bitis arietans	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27733	Rosa hybrid cultivar	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14313	Pachybasium candidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15205	Alaria crispa	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24409	Evasterias troschelii	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27340	Campylopus clavatus	Species	Leucobryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14807	Arenaria juncea	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8804	Raputia simulans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16025	Werneria decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16475	Plumbago pulchella	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12490	Lecidea speirodes	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5047	Evodiopanax innovans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15349	Acacia sparsiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12293	Euphorbia iberica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27636	Hippasteria phrygiana	Species	Goniasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13442	Eucalyptus regnans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27131	Methylosinus trichosporium	Species	Methylocystaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27756	Lepidiota negatoria	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27230	Eysenhardtia platycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2038	Myrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27074	Dermocybe semisanguinea	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20219	Rhizobium etli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27794	Acritopappus longifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO820	Grindelia perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9137	Tasmannia lanceolata	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27449	Halichondria okadai	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2827	Plumeria alba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27709	Rhododendron maximum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27211	Adenocarpus hispanicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27651	Cissus tricuspidata	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27194	Conger myriaster	Species	Congridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27594	Viola odorata	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27411	Liparis nakaharai	Species	Liparidae	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 NPC94101 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	27828
0.1-0.2	20034
0.2-0.3	1884
0.3-0.4	97
0.4-0.5	12
0.5-0.6	2
0.6-0.7	1
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
0.7015	Intermediate Similarity	NPC82633
0.6389	Remote Similarity	NPC223993
0.5541	Remote Similarity	NPC235109
0.5467	Remote Similarity	NPC163685

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC94101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7794
0.1-0.2	1340
0.2-0.3	14
0.3-0.4	2
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