NPASS Compound

Natural Product: NPC2701

Natural Product ID	NPC2701
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FCVMOPRCAKSDFE-JUERTLPWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101615132
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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 100104 0 0 0 0 0 0 0 0999 V2000 -8.8283 1.5128 -0.4074 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6263 0.0357 -0.0899 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9686 -0.0426 1.2590 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6301 0.6485 1.3281 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6164 0.1095 0.3869 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3192 0.8985 0.5529 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8575 0.6881 1.9755 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2563 0.3954 -0.3716 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7390 0.4844 -1.8408 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4902 0.5866 -2.6828 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3880 0.4602 -1.6647 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1037 1.0746 -2.0620 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7716 1.1181 -0.8308 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1687 2.0223 0.1958 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1142 1.2942 0.6666 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0283 1.2338 -0.4953 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4221 2.6194 -0.9489 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2037 1.3313 -1.1500 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4857 2.4279 -2.1458 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0299 1.6346 0.0797 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4948 1.5178 -0.3777 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8046 0.0624 -0.4487 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9483 -0.6108 -1.4627 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6817 0.0628 -1.7739 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8813 -0.4783 -2.6752 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5959 0.1504 -3.0292 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1111 -0.1105 -4.1553 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1196 -0.2402 -0.7090 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7661 -0.9499 0.2878 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3800 -2.2148 -0.3277 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8686 -3.0537 0.8051 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5367 -2.1993 1.8222 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7924 -0.7861 1.4374 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1930 -0.6403 0.8379 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1369 -1.2833 1.6180 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8401 -0.1622 0.6902 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8746 -2.2405 3.0699 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6309 -4.1422 0.3908 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4461 -2.8729 -1.1260 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9928 -1.4146 1.8637 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3085 -1.4303 3.2149 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4238 -2.4971 1.0168 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8252 1.6673 -0.8632 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8258 2.1181 0.5418 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0051 1.9225 -1.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6123 -0.4509 -0.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0598 -0.4776 -0.8803 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6375 0.5816 1.9381 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3617 0.7325 2.3751 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8262 1.7219 0.9986 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4349 -0.9708 0.4557 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0040 0.2901 -0.6539 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5812 1.9495 0.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6796 1.6091 2.5361 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9093 0.0659 1.9764 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5733 0.0013 2.5055 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9772 -0.6459 -0.1833 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2441 -0.4889 -2.0919 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4437 1.2920 -2.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3952 -0.2886 -3.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4289 1.5009 -3.2798 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2651 -0.5878 -1.3543 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2522 2.0701 -2.5246 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6985 0.0758 -0.3931 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8140 2.0878 1.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0586 3.0321 -0.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5772 1.9164 1.4631 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7999 0.3014 0.9831 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5126 2.7810 -1.0138 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9610 2.9362 -1.8963 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0673 3.3715 -0.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6218 2.7997 -2.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0050 3.3015 -1.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2362 2.0976 -2.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9121 0.8600 0.8704 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8440 2.6572 0.4368 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0745 2.0721 0.3774 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5474 1.9778 -1.3682 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5585 -0.3702 0.5588 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8079 -1.6856 -1.1863 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5203 -0.6626 -2.4368 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1848 -1.4015 -3.1582 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1639 -1.1793 1.1630 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1713 -1.8610 -1.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9479 -3.4896 1.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5463 -2.6597 2.0407 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8529 -0.2017 2.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4898 0.4474 0.8202 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2348 -0.9599 -0.2220 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4486 -2.1373 1.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2003 -1.4401 3.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2367 -5.0193 0.6689 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0807 -3.6249 -0.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0750 -1.6717 2.0981 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7163 -2.3038 3.7800 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5368 -0.5303 3.8028 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2144 -1.6326 3.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4872 -2.8601 1.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1258 -3.3831 1.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3731 -2.2531 -0.0643 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 8 9 1 0 9 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 6 13 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 22 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 30 39 1 0 3 40 1 0 40 41 1 0 40 42 1 0 16 8 1 0 24 18 1 0 36 29 1 0 16 11 1 0 26 12 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 1 4 49 1 0 4 50 1 0 5 51 1 0 5 52 1 0 6 53 1 6 7 54 1 0 7 55 1 0 7 56 1 0 8 57 1 1 9 58 1 0 9 59 1 0 10 60 1 0 10 61 1 0 11 62 1 1 12 63 1 6 13 64 1 1 14 65 1 0 14 66 1 0 15 67 1 0 15 68 1 0 17 69 1 0 17 70 1 0 17 71 1 0 19 72 1 0 19 73 1 0 19 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 21 78 1 0 22 79 1 1 23 80 1 0 23 81 1 0 25 82 1 0 29 83 1 1 30 84 1 6 31 85 1 1 32 86 1 1 33 87 1 1 34 88 1 0 34 89 1 0 35 90 1 0 37 91 1 0 38 92 1 0 39 93 1 0 40 94 1 0 41 95 1 0 41 96 1 0 41 97 1 0 42 98 1 0 42 99 1 0 42100 1 0 M END

Standard InCHIKey	FCVMOPRCAKSDFE-JUERTLPWSA-N
Standard InCHI	InChI=1S/C35H58O7/c1-7-21(19(2)3)9-8-20(4)24-10-11-25-29-26(13-15-35(24,25)6)34(5)14-12-23(16-22(34)17-27(29)37)41-33-32(40)31(39)30(38)28(18-36)42-33/h17,19-21,23-26,28-33,36,38-40H,7-16,18H2,1-6H3/t20-,21-,23+,24-,25+,26+,28-,29+,30-,31+,32-,33-,34+,35-/m1/s1
SMILES	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H](CC1=CC3=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	590.42	Volume:	627.392 ? Van der Waals volume.
Dense:	0.941	LogP:	4.769 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.537 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.953 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	27.0
TPSA:	116.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	7.0

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:	5.109	Fsp³:	0.914
MCE-18:	92.418 ? 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:	0.985	Fluc inhibitor:	0.006 ? 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:	0.187	Promiscuous compounds:	0.302

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.402	MDCK Permeability:	-5.126
Pgp-inhibitor:	0.0	Pgp-substrate:	0.035
PAMPA:	0.722 ? 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%):	0.003	30% Bioavailability (F30%):	0.653
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.001
Plasma Protein Binding (PPB):	74.203%	Volume Distribution (VD):	-0.486
Fu:	21.143% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.099
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.996	CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.797 ? 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):

3.483

Half-life (T1/2):

1.232

ADMET: Toxicity

hERG Blockers:	0.063	hERG Blockers (10um):	0.195
Human Hepatotoxicity (H-HT):	0.765	Drug-induced Liver Injury (DILI):	0.925
AMES Toxicity:	0.722	Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.035	Skin Sensitization:	1.0
Carcinogencity:	0.347	Eye Corrosion:	0.001
Eye Irritation:	0.242	Respiratory Toxicity:	0.183
Drug-induced Neurotoxicity:	0.023	Ototoxicity:	0.919
Hematotoxicity:	0.689	Drug-induced Nephrotoxicity:	0.652
Genotoxicity:	0.01	RPMI-8226 Immunitoxicity:	0.105
A549 Cytotoxicity:	0.887	Hek293 Cytotoxicity:	0.54
BCF:	2.626 ? 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:	4.398 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.181 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.003 ? 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
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	Leaves	Huangshan, Anhui Province, China	2008-NOV	PMID[21384845]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21384845]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23632365]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4855	Colchicum speciosum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3868	Senecio sinuatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11165	Spirographis spallanzani	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1507	Cissus quinquefolia	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4855	Colchicum speciosum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9388	Heliomeris multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

Organism ID	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 NPC2701 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	13686
0.1-0.2	28304
0.2-0.3	6710
0.3-0.4	1060
0.4-0.5	78
0.5-0.6	7
0.6-0.7	6
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC22140
0.8	Intermediate Similarity	NPC243728
0.7397	Intermediate Similarity	NPC470434
0.7067	Intermediate Similarity	NPC608180
0.6986	Remote Similarity	NPC473890
0.6463	Remote Similarity	NPC486114
0.6364	Remote Similarity	NPC158088
0.6232	Remote Similarity	NPC145879
0.6203	Remote Similarity	NPC282669
0.6047	Remote Similarity	NPC295389
0.5333	Remote Similarity	NPC272015
0.5309	Remote Similarity	NPC267510
0.52	Remote Similarity	NPC44083
0.5135	Remote Similarity	NPC31564
0.5125	Remote Similarity	NPC207617
0.5125	Remote Similarity	NPC607440
0.5055	Remote Similarity	NPC181845

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC2701 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5775
0.1-0.2	3128
0.2-0.3	230
0.3-0.4	14
0.4-0.5	3
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