NPASS Compound

Natural Product: NPC50988

Natural Product ID	NPC50988
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RXPXPIXYLTUYHE-NKEJTZRQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 99104 0 0 0 0 0 0 0 0999 V2000 -7.8955 -2.0712 1.0108 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0176 -1.6704 -0.1526 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2018 -2.7732 -1.2143 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5300 -0.4180 -0.7837 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0600 0.8678 -0.2053 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6225 0.7890 0.3396 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9719 2.1134 0.0299 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5156 2.0343 0.3581 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7599 0.9734 -0.4094 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5163 1.6033 -1.7783 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5479 -0.2926 -0.5739 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8844 -1.3711 -0.9628 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4201 -1.3948 -1.2442 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6684 -0.2566 -0.6615 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6782 -0.6987 -0.1128 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6020 -1.9471 0.7381 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4256 -1.1490 -1.3909 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8665 -1.3189 -0.9533 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4124 0.1115 -0.9888 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5475 1.0345 -0.2062 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1287 2.1728 -1.0908 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4700 1.6833 0.8480 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4367 0.3913 0.5681 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6109 1.4609 1.2125 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6136 1.8613 0.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4684 0.6056 0.2695 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7256 0.0178 1.6059 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7526 0.0628 -0.5601 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8282 0.3142 -1.3962 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5714 0.5970 -2.5894 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2266 0.2547 -0.9131 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5126 -0.0370 0.3222 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8790 -0.0921 0.7818 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1264 -0.4077 2.1079 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3941 -0.4853 2.6419 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4740 -0.2403 1.8317 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2543 0.0741 0.5148 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9586 0.1501 -0.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3457 0.3256 -0.3201 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7454 -0.3199 2.3749 O 0 0 0 0 0 1 0 0 0 0 0 0 3.5444 -2.0212 -1.9477 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9854 -0.3576 -0.3701 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5435 -1.6032 0.2410 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7427 0.6502 1.8011 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9118 0.6919 2.3254 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7208 0.4756 2.6975 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8266 -1.4848 1.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3248 -2.0045 1.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2115 -3.1442 0.9531 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2620 -2.7643 -1.4826 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8825 -3.7123 -0.7072 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5102 -2.5272 -2.0296 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6590 -0.4691 -0.6810 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3913 -0.4682 -1.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1209 1.6488 -1.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7455 1.2358 0.6003 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1878 2.4701 -0.9911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4199 2.8587 0.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0765 3.0285 0.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4525 1.9354 1.4576 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0569 0.9568 -2.5101 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5625 1.7894 -2.1718 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0843 2.5881 -1.6114 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3772 -2.3489 -1.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9917 -2.4105 -1.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3754 -1.4014 -2.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3932 0.4229 -1.5045 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3788 -2.3742 0.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1319 -1.7164 1.7122 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2290 -2.7973 0.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0441 -2.1661 -1.6316 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3151 -0.4354 -2.2038 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9599 -1.7655 0.0349 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4192 0.3804 -2.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0752 2.4897 -1.6266 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4196 1.9351 -1.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8526 3.0979 -0.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4126 1.1107 1.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2307 2.7545 0.9813 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5247 1.6475 0.5055 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9684 -0.1086 1.4430 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3536 1.2322 2.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2538 2.3878 1.3060 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2166 2.5135 1.1460 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4468 2.4169 -0.4473 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8255 -0.3985 2.1061 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5524 -0.7119 1.5531 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0294 0.8261 2.3032 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9728 0.4680 -1.6511 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6630 -0.2350 0.9809 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2958 -0.6061 2.7716 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5718 -0.7335 3.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8559 0.4022 -1.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6262 -0.4099 -0.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4905 -2.1457 -1.7454 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4202 -0.3251 -1.4386 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5238 -1.5510 1.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0926 -2.5423 -0.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7359 0.7707 3.6669 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 19 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 37 39 1 0 36 40 1 0 18 41 1 0 11 42 1 0 42 43 1 0 6 44 1 1 44 45 2 0 44 46 1 0 43 2 1 0 42 6 1 0 26 9 1 0 38 33 1 0 26 14 1 0 23 15 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 10 61 1 0 10 62 1 0 10 63 1 0 12 64 1 0 13 65 1 0 13 66 1 0 14 67 1 6 16 68 1 0 16 69 1 0 16 70 1 0 17 71 1 0 17 72 1 0 18 73 1 1 19 74 1 6 21 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 22 80 1 0 23 81 1 1 24 82 1 0 24 83 1 0 25 84 1 0 25 85 1 0 27 86 1 0 27 87 1 0 27 88 1 0 31 89 1 0 32 90 1 0 34 91 1 0 35 92 1 0 38 93 1 0 39 94 1 0 41 95 1 0 42 96 1 6 43 97 1 0 43 98 1 0 46 99 1 0 M CHG 1 40 -1 M END

Standard InCHIKey	RXPXPIXYLTUYHE-NKEJTZRQSA-N
Standard InCHI	InChI=1S/C39H54O7/c1-34(2)16-18-39(33(44)45)19-17-37(6)24(25(39)21-34)10-12-30-36(5)22-28(42)32(35(3,4)29(36)14-15-38(30,37)7)46-31(43)13-9-23-8-11-26(40)27(41)20-23/h8-11,13,20,25,28-30,32,40-42H,12,14-19,21-22H2,1-7H3,(H,44,45)/p-1/b13-9+/t25-,28-,29-,30-,32+,36+,37-,38-,39+/m1/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@H]5CC[C@@]34C)OC(=O)/C=C/c3ccc(c(c3)O)[O-])O)[C@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.39	Volume:	674.838 ? Van der Waals volume.
Dense:	0.94	LogP:	4.61 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.746 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.98 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	35.0
TPSA:	124.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.115	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.033	Fsp³:	0.692
MCE-18:	169.485 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.987	Fluc inhibitor:	0.686 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.236 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.042 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.123	Promiscuous compounds:	0.131

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.521	MDCK Permeability:	-5.066
Pgp-inhibitor:	0.017	Pgp-substrate:	0.0
PAMPA:	0.992 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.858	30% Bioavailability (F30%):	0.785
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.773
Plasma Protein Binding (PPB):	94.632%	Volume Distribution (VD):	-0.128
Fu:	5.69% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
BSEP inhibitor:	0.946

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.983
HLM stability:	0.661 ? 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):

4.838

Half-life (T1/2):

1.315

ADMET: Toxicity

hERG Blockers:	0.053	hERG Blockers (10um):	0.147
Human Hepatotoxicity (H-HT):	0.578	Drug-induced Liver Injury (DILI):	0.624
AMES Toxicity:	0.2	Rat Oral Acute Toxicity:	0.189
Maximum Recommended Daily Dose:	0.631	Skin Sensitization:	0.984
Carcinogencity:	0.6	Eye Corrosion:	0.002
Eye Irritation:	0.401	Respiratory Toxicity:	0.572
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.872
Hematotoxicity:	0.089	Drug-induced Nephrotoxicity:	0.678
Genotoxicity:	0.696	RPMI-8226 Immunitoxicity:	0.01
A549 Cytotoxicity:	0.24	Hek293 Cytotoxicity:	0.134
BCF:	1.525 ? 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:	4.737 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.471 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.813 ? 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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 17014425]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/bab.1236]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2010.09.006]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	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 NPC50988 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	7444
0.1-0.2	37899
0.2-0.3	3840
0.3-0.4	414
0.4-0.5	194
0.5-0.6	40
0.6-0.7	14
0.7-0.8	0
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8444	Intermediate Similarity	NPC605663
0.8315	Intermediate Similarity	NPC171007
0.8315	Intermediate Similarity	NPC190849
0.8021	Intermediate Similarity	NPC601567
0.8021	Intermediate Similarity	NPC606631
0.7071	Intermediate Similarity	NPC482051
0.7041	Intermediate Similarity	NPC304110
0.7041	Intermediate Similarity	NPC27518
0.7041	Intermediate Similarity	NPC611516
0.6869	Remote Similarity	NPC132126
0.6869	Remote Similarity	NPC25491
0.6762	Remote Similarity	NPC53520
0.6735	Remote Similarity	NPC22676
0.6731	Remote Similarity	NPC118033
0.6667	Remote Similarity	NPC479745
0.6571	Remote Similarity	NPC481234
0.6571	Remote Similarity	NPC479431
0.6569	Remote Similarity	NPC610795
0.6471	Remote Similarity	NPC178093
0.6408	Remote Similarity	NPC324798
0.6408	Remote Similarity	NPC479742
0.6176	Remote Similarity	NPC198621
0.6176	Remote Similarity	NPC216940
0.581	Remote Similarity	NPC488214
0.5686	Remote Similarity	NPC173569
0.5684	Remote Similarity	NPC230151
0.566	Remote Similarity	NPC172311
0.5619	Remote Similarity	NPC488215
0.5566	Remote Similarity	NPC262970
0.5543	Remote Similarity	NPC120840
0.5534	Remote Similarity	NPC43353
0.5514	Remote Similarity	NPC482052
0.5472	Remote Similarity	NPC101863
0.5472	Remote Similarity	NPC477873
0.5464	Remote Similarity	NPC233012
0.5437	Remote Similarity	NPC485587
0.5413	Remote Similarity	NPC479739
0.537	Remote Similarity	NPC479744
0.5357	Remote Similarity	NPC206232
0.5357	Remote Similarity	NPC14515
0.5333	Remote Similarity	NPC475138
0.5326	Remote Similarity	NPC84319
0.5326	Remote Similarity	NPC52021
0.5326	Remote Similarity	NPC599947
0.5321	Remote Similarity	NPC606782
0.5283	Remote Similarity	NPC477874
0.5269	Remote Similarity	NPC110308
0.5268	Remote Similarity	NPC479740
0.5268	Remote Similarity	NPC479741
0.5217	Remote Similarity	NPC480946
0.5217	Remote Similarity	NPC130577
0.5217	Remote Similarity	NPC142415
0.5217	Remote Similarity	NPC102683
0.5208	Remote Similarity	NPC296164
0.5172	Remote Similarity	NPC481235
0.514	Remote Similarity	NPC26045
0.5135	Remote Similarity	NPC479747
0.5135	Remote Similarity	NPC479746
0.5106	Remote Similarity	NPC231063
0.5106	Remote Similarity	NPC282395
0.5106	Remote Similarity	NPC481360
0.5053	Remote Similarity	NPC200752
0.5047	Remote Similarity	NPC18982

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC50988 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3464
0.1-0.2	5623
0.2-0.3	58
0.3-0.4	4
0.4-0.5	0
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
0.5321	Remote Similarity	NPD8166	Discontinued

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