NPASS Compound

Natural Product: NPC273997

Natural Product ID	NPC273997
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SCHSEISSFMEKOL-CCSNDEMQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14702506
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 97101 0 0 0 0 0 0 0 0999 V2000 8.0194 1.6577 1.6141 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6736 1.3501 0.9919 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6204 2.3252 1.5076 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7730 1.3654 -0.4660 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9630 1.7196 -1.0163 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6944 1.1341 -1.4538 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4892 -0.1907 -1.9874 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1363 -1.4240 -1.2820 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0922 -1.8812 -0.2164 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7138 -1.7886 -1.1378 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4677 -3.0793 -0.4170 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3644 -2.7268 0.6065 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5916 -1.7748 -0.2488 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4534 -1.0765 0.3386 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1965 -0.2593 -0.7600 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7344 0.5408 -1.5627 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1100 0.0112 -1.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7010 -0.8001 -0.6622 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0561 0.0198 0.4971 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2237 0.6326 -0.0432 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5455 1.6635 0.8318 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1397 1.3290 -1.0239 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4527 0.6392 -1.1832 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2615 0.4872 0.0582 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3673 0.3893 1.2997 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0998 -0.2038 0.8211 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7975 -1.4413 1.1682 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5764 -2.1486 0.7547 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0782 -2.7903 1.9139 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2733 1.3991 0.2238 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5403 0.7717 0.2719 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1491 1.0281 1.6273 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6186 0.7391 1.6455 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0318 0.0238 0.3829 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5832 0.8149 -0.8011 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6322 -0.0603 -2.0570 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3142 1.3315 -0.7158 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5353 -1.2735 0.3083 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0013 0.0234 2.7872 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9773 2.3811 1.9291 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5185 -3.7014 0.1611 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3607 2.6820 1.4839 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8578 1.5104 2.7259 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7659 0.8878 1.3479 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3792 0.3716 1.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8478 2.5392 0.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1550 1.9338 2.4340 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1814 3.2399 1.8011 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1327 1.7601 -2.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7625 1.9683 -0.3578 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7527 1.6722 -1.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9728 1.8060 -2.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7247 -0.1385 -2.8573 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4371 -0.3650 -2.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4234 -2.2274 -2.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6926 -1.8456 0.8107 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5135 -2.8991 -0.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0192 -1.2525 -0.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -2.0022 -2.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9566 -3.8454 -1.0674 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8077 -3.6517 0.8534 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7748 -2.3129 1.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2484 -2.3451 -1.1369 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5917 -0.4819 1.2374 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7973 -0.9629 -1.3725 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7804 1.5797 -1.1651 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2891 0.6645 -2.5962 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7624 0.8731 -1.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1819 -0.6227 -2.6922 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5341 -0.2091 1.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8302 1.0855 0.2814 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1332 0.0007 0.7734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5551 1.5601 0.8575 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8515 2.7028 0.5490 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8941 1.5609 1.8941 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3086 2.3575 -0.6605 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6709 1.4109 -2.0149 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2576 -0.3393 -1.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0530 1.2292 -1.9127 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7461 -0.5334 0.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8498 -0.1821 2.0935 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1987 1.4533 1.6099 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4864 -2.0157 1.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7013 -2.8570 -0.0668 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0296 -2.1206 2.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4042 -0.3365 0.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6071 0.4675 2.4168 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2250 1.6849 1.6755 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1570 -0.0438 0.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3563 1.6127 -0.9863 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2403 -1.0731 -1.8062 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0156 0.4334 -2.8523 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6641 -0.1052 -2.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9775 -1.8945 0.9354 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3846 -0.7224 2.9818 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4741 2.9026 1.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7478 -4.5789 -0.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 15 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 24 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 34 38 1 0 33 39 1 0 32 40 1 0 11 41 1 0 18 10 1 0 26 20 1 0 37 31 1 0 18 13 1 0 28 14 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 3 46 1 0 3 47 1 0 3 48 1 0 5 49 1 0 5 50 1 0 6 51 1 0 6 52 1 0 7 53 1 0 7 54 1 0 8 55 1 6 9 56 1 0 9 57 1 0 9 58 1 0 10 59 1 6 11 60 1 6 12 61 1 0 12 62 1 0 13 63 1 6 14 64 1 1 15 65 1 6 16 66 1 0 16 67 1 0 17 68 1 0 17 69 1 0 19 70 1 0 19 71 1 0 19 72 1 0 21 73 1 0 21 74 1 0 21 75 1 0 22 76 1 0 22 77 1 0 23 78 1 0 23 79 1 0 24 80 1 6 25 81 1 0 25 82 1 0 27 83 1 0 28 84 1 6 29 85 1 0 31 86 1 6 32 87 1 1 33 88 1 1 34 89 1 1 35 90 1 6 36 91 1 0 36 92 1 0 36 93 1 0 38 94 1 0 39 95 1 0 40 96 1 0 41 97 1 0 M END

Standard InCHIKey	SCHSEISSFMEKOL-CCSNDEMQSA-N
Standard InCHI	InChI=1S/C34H56O7/c1-17(2)18(3)8-9-19(4)28-26(36)16-24-27-23(11-13-34(24,28)7)33(6)12-10-22(14-21(33)15-25(27)35)41-32-31(39)30(38)29(37)20(5)40-32/h15,17,19-20,22-32,35-39H,3,8-14,16H2,1-2,4-7H3/t19-,20+,22+,23+,24+,25+,26+,27-,28+,29-,30-,31+,32+,33+,34+/m1/s1
SMILES	CC(C)C(=C)CC[C@@H](C)[C@H]1[C@H](C[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H](CC1=C[C@@H]3O)O[C@H]1[C@H]([C@@H]([C@@H]([C@H](C)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.4	Volume:	610.096 ? Van der Waals volume.
Dense:	0.945	LogP:	4.061 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.899 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.967 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	27.0
TPSA:	119.61 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.286	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.374	Fsp³:	0.882
MCE-18:	97.125 ? 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:	0.924	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? 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:	0.183	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.454	MDCK Permeability:	-5.126
Pgp-inhibitor:	0.009	Pgp-substrate:	0.872
PAMPA:	0.91 ? 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%):	0.303	30% Bioavailability (F30%):	0.94
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.599
Plasma Protein Binding (PPB):	81.873%	Volume Distribution (VD):	-0.238
Fu:	15.931% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.05
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.279 ? 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):

5.4

Half-life (T1/2):

2.044

ADMET: Toxicity

hERG Blockers:	0.078	hERG Blockers (10um):	0.427
Human Hepatotoxicity (H-HT):	0.298	Drug-induced Liver Injury (DILI):	0.274
AMES Toxicity:	0.367	Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.255	Skin Sensitization:	0.771
Carcinogencity:	0.077	Eye Corrosion:	0.0
Eye Irritation:	0.068	Respiratory Toxicity:	0.136
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.982
Hematotoxicity:	0.291	Drug-induced Nephrotoxicity:	0.531
Genotoxicity:	0.008	RPMI-8226 Immunitoxicity:	0.14
A549 Cytotoxicity:	0.131	Hek293 Cytotoxicity:	0.175
BCF:	1.775 ? 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:	3.729 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.063 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.433 ? 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
NPO19125	Hoppea dichotoma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)84903-1]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691710]
NPO19125	Hoppea dichotoma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11190384]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	branch	n.a.	PMID[17202693]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	Kubat, Malaysia	1991	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1965654]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38358042]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778241]
NPO19125	Hoppea dichotoma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18789	Cosmos caudatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16097	Ottonia corcovadensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16826	Streptomyces refuineus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6175	Colletotrichum fragariae	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7783	Agathosma affinis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15968	Annella mollis	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16964	Aplophyllum tenue	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15604	Bombax oleagineum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10708	Colchicum kesselringii	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18846	Gastrolobium grandiflorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18376	Oryctolagus cuniculus	Species	Leporidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1307	Rabdosia trichocarpa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11591	Rhododendron simiarum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18705	Sinularia crassa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12810	Adenostyles alliariae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14472	Sinularia ovispiculata	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16826	Streptomyces refuineus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15196	Aframomum giganteum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15968	Annella mollis	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15604	Bombax oleagineum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11591	Rhododendron simiarum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1307	Rabdosia trichocarpa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18789	Cosmos caudatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16097	Ottonia corcovadensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10708	Colchicum kesselringii	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18846	Gastrolobium grandiflorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19125	Hoppea dichotoma	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7783	Agathosma affinis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14753	Croton argyroglossum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15525	Albertisia delagoensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12810	Adenostyles alliariae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13917	Chondrilla juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18705	Sinularia crassa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16964	Aplophyllum tenue	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18376	Oryctolagus cuniculus	Species	Leporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9552	Phyllobates terribilis	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14472	Sinularia ovispiculata	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6175	Colletotrichum fragariae	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1188	Pteris wallichiana	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14988	Chione glabra	Species	Rubiaceae	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 NPC273997 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	21553
0.1-0.2	23842
0.2-0.3	4004
0.3-0.4	413
0.4-0.5	43
0.5-0.6	4
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
0.5926	Remote Similarity	NPC470434
0.5204	Remote Similarity	NPC141433
0.5169	Remote Similarity	NPC62188
0.5114	Remote Similarity	NPC210178

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC273997 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7407
0.1-0.2	1620
0.2-0.3	112
0.3-0.4	10
0.4-0.5	1
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