NPASS Compound

Natural Product: NPC125881

Natural Product ID	NPC125881
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WBWUKXBPKMFLHV-CXLVWPLDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101630630
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 100105 0 0 0 0 0 0 0 0999 V2000 -8.5017 2.6031 -2.6282 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5691 2.2366 -1.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6582 2.2007 -0.6578 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3601 1.9261 -0.4175 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7229 1.6526 1.0332 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4915 0.8749 1.5247 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3607 -0.1075 0.3579 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1279 -0.9215 0.3888 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7076 -1.1316 1.8172 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4132 -1.8392 2.0114 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3737 -1.3390 1.0659 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0110 -1.9000 1.2835 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0853 -1.2711 0.2677 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4979 -1.7881 -1.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8409 -1.1013 -1.3778 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8733 -1.4392 -0.3603 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4217 -2.8035 -0.7050 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9764 -0.3891 -0.4277 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4234 -0.0570 -1.8053 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4039 1.1146 -1.6317 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6343 0.6725 -0.8862 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4614 -0.1652 -1.8282 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2265 -1.4558 0.5933 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9710 -0.3063 0.7826 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3875 -0.2077 2.2040 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7031 -0.9108 2.4962 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1966 -1.5409 1.2253 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2474 -0.3717 0.2077 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0555 -0.8916 -0.9261 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4064 -0.9132 -0.6159 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9613 0.3736 -0.4930 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6911 0.6214 0.7850 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0662 2.1139 0.7486 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0512 2.2943 -0.3542 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8136 1.4359 -1.5425 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1389 0.6615 -1.7627 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1123 -0.0165 -2.9808 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8327 0.5414 -1.5500 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9752 3.6447 -0.7752 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5757 2.5175 1.9573 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9775 0.3525 1.9424 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9149 -0.2456 -0.1834 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3934 -2.1546 1.4112 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6222 -1.7886 3.5567 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3717 1.1147 2.6116 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4663 -0.9789 0.5234 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5079 3.0839 -2.8605 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2373 3.4462 -2.7504 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6984 1.7792 -3.3150 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6419 2.7980 -0.3813 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7565 2.5863 1.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6091 1.0176 1.1523 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7402 0.2654 2.4218 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6258 1.5230 1.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3919 -1.9380 -0.0326 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4911 -1.7077 2.3549 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6339 -0.1303 2.3246 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4758 -2.9480 2.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0471 -1.5574 3.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2812 -0.2292 1.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6670 -1.5484 2.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9730 -3.0130 1.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2935 -0.1818 0.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6800 -2.8798 -1.0080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1645 -1.5144 -1.8955 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2143 -1.3876 -2.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6365 -0.0155 -1.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9221 -3.3214 0.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1763 -2.6660 -1.5142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6277 -3.4474 -1.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5969 0.5187 0.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0261 -0.8620 -2.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6129 0.3255 -2.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7027 1.5211 -2.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8634 1.8920 -1.0332 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3039 -1.2593 -1.6477 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5450 -0.0093 -1.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1816 -0.0163 -2.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2565 0.5544 0.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6264 -0.7606 2.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4117 -0.1031 2.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4148 -2.2531 0.8347 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5685 0.5587 0.6506 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6823 -1.9126 -1.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8899 -0.3005 -1.8731 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1343 1.1073 -0.6535 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5974 -0.0170 0.8293 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1247 2.6523 0.4993 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0970 2.2133 0.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7451 2.0521 -2.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2111 -0.0590 -0.9263 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9453 1.3877 -1.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6282 -0.8623 -2.9337 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7367 3.8807 -1.3643 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9851 3.4121 1.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4223 0.8900 2.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6805 -2.0370 2.3425 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5177 -1.2693 4.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2189 1.7359 1.8547 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2074 -1.9106 0.3519 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 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 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 13 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 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 35 36 1 0 36 37 1 0 35 38 1 0 34 39 1 0 33 40 1 0 32 41 1 0 28 42 1 0 27 43 1 0 26 44 1 0 25 45 1 0 7 46 1 1 21 4 1 0 42 24 1 0 21 7 1 0 38 31 1 0 18 8 1 0 16 11 1 0 1 47 1 0 1 48 1 0 1 49 1 0 4 50 1 1 5 51 1 0 5 52 1 0 6 53 1 0 6 54 1 0 8 55 1 6 9 56 1 0 9 57 1 0 10 58 1 0 10 59 1 0 11 60 1 1 12 61 1 0 12 62 1 0 13 63 1 6 14 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 17 68 1 0 17 69 1 0 17 70 1 0 18 71 1 1 19 72 1 0 19 73 1 0 20 74 1 0 20 75 1 0 22 76 1 0 22 77 1 0 22 78 1 0 24 79 1 6 25 80 1 1 26 81 1 1 27 82 1 6 28 83 1 1 29 84 1 0 29 85 1 0 31 86 1 6 32 87 1 6 33 88 1 6 34 89 1 1 35 90 1 6 36 91 1 0 36 92 1 0 37 93 1 0 39 94 1 0 40 95 1 0 41 96 1 0 43 97 1 0 44 98 1 0 45 99 1 0 46100 1 0 M END

Standard InCHIKey	WBWUKXBPKMFLHV-CXLVWPLDSA-N
Standard InCHI	InChI=1S/C33H54O13/c1-15(35)18-8-11-33(42)20-5-4-16-12-17(6-9-31(16,2)19(20)7-10-32(18,33)3)44-30-28(41)26(39)24(37)22(46-30)14-43-29-27(40)25(38)23(36)21(13-34)45-29/h16-30,34,36-42H,4-14H2,1-3H3/t16-,17-,18+,19-,20+,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31-,32+,33-/m0/s1
SMILES	CC(=O)[C@H]1CC[C@@]2([C@@H]3CC[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	658.36	Volume:	639.622 ? Van der Waals volume.
Dense:	1.029	LogP:	1.095 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.775 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.882 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	33.0
TPSA:	215.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.16	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.43	Fsp³:	0.97
MCE-18:	121.723 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.607	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.271	Promiscuous compounds:	0.292

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.411	MDCK Permeability:	-5.083
Pgp-inhibitor:	0.0	Pgp-substrate:	0.741
PAMPA:	0.984 ? 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):	0.051
20% Bioavailability (F20%):	0.039	30% Bioavailability (F30%):	0.899
50% Bioavailability (F50%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012	MRP1:	0.055
Plasma Protein Binding (PPB):	60.226%	Volume Distribution (VD):	-0.426
Fu:	31.335% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.009
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.102	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.167	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	0.197
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.461
HLM stability:	0.041 ? 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):

1.082

Half-life (T1/2):

3.035

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.06
Human Hepatotoxicity (H-HT):	0.647	Drug-induced Liver Injury (DILI):	0.543
AMES Toxicity:	0.853	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.086	Skin Sensitization:	1.0
Carcinogencity:	0.496	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.02
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.99
Hematotoxicity:	0.443	Drug-induced Nephrotoxicity:	0.861
Genotoxicity:	0.347	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.55	Hek293 Cytotoxicity:	0.754
BCF:	1.085 ? 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:	3.215 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.306 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.687 ? 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
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12987	Rhododendron farrerae	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12987	Rhododendron farrerae	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18054	Curvularia coicis	Species	Pleosporaceae	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 NPC125881 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	19716
0.1-0.2	25094
0.2-0.3	3679
0.3-0.4	1126
0.4-0.5	166
0.5-0.6	46
0.6-0.7	24
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
0.7561	Intermediate Similarity	NPC30483
0.7561	Intermediate Similarity	NPC470897
0.6889	Remote Similarity	NPC479357
0.6739	Remote Similarity	NPC486144
0.6739	Remote Similarity	NPC486145
0.6739	Remote Similarity	NPC486147
0.6739	Remote Similarity	NPC486148
0.6707	Remote Similarity	NPC5311
0.6559	Remote Similarity	NPC479358
0.6559	Remote Similarity	NPC475590
0.6452	Remote Similarity	NPC479360
0.6452	Remote Similarity	NPC479359
0.6421	Remote Similarity	NPC475419
0.6354	Remote Similarity	NPC474908
0.6354	Remote Similarity	NPC486134
0.6354	Remote Similarity	NPC486141
0.6222	Remote Similarity	NPC479353
0.6222	Remote Similarity	NPC479354
0.6162	Remote Similarity	NPC474423
0.6111	Remote Similarity	NPC236973
0.6111	Remote Similarity	NPC292467
0.6087	Remote Similarity	NPC486143
0.6087	Remote Similarity	NPC486142
0.6087	Remote Similarity	NPC486149
0.6061	Remote Similarity	NPC488945
0.6061	Remote Similarity	NPC488946
0.5882	Remote Similarity	NPC99620
0.5876	Remote Similarity	NPC486136
0.5842	Remote Similarity	NPC488947
0.5806	Remote Similarity	NPC231518
0.5806	Remote Similarity	NPC488944
0.5747	Remote Similarity	NPC77299
0.5747	Remote Similarity	NPC480906
0.5682	Remote Similarity	NPC480914
0.5625	Remote Similarity	NPC486146
0.5591	Remote Similarity	NPC40749
0.549	Remote Similarity	NPC486150
0.5474	Remote Similarity	NPC488941
0.5474	Remote Similarity	NPC488940
0.5455	Remote Similarity	NPC488943
0.5455	Remote Similarity	NPC488942
0.5446	Remote Similarity	NPC120390
0.5435	Remote Similarity	NPC480907
0.5435	Remote Similarity	NPC20028
0.5376	Remote Similarity	NPC80191
0.5368	Remote Similarity	NPC480910
0.5368	Remote Similarity	NPC240070
0.5368	Remote Similarity	NPC480909
0.5357	Remote Similarity	NPC246399
0.5357	Remote Similarity	NPC34977
0.5357	Remote Similarity	NPC221196
0.5333	Remote Similarity	NPC76572
0.5333	Remote Similarity	NPC193382
0.5294	Remote Similarity	NPC74259
0.5263	Remote Similarity	NPC32177
0.5263	Remote Similarity	NPC469756
0.5263	Remote Similarity	NPC275901
0.5258	Remote Similarity	NPC486135
0.5258	Remote Similarity	NPC486137
0.5208	Remote Similarity	NPC188234
0.5208	Remote Similarity	NPC310031
0.5204	Remote Similarity	NPC232785
0.5204	Remote Similarity	NPC486139
0.52	Remote Similarity	NPC475219
0.5172	Remote Similarity	NPC39485
0.5165	Remote Similarity	NPC65550
0.5165	Remote Similarity	NPC172838
0.5149	Remote Similarity	NPC488938
0.5149	Remote Similarity	NPC488937
0.5102	Remote Similarity	NPC208193
0.5055	Remote Similarity	NPC469750
0.505	Remote Similarity	NPC486131

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC125881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6647
0.1-0.2	2369
0.2-0.3	111
0.3-0.4	14
0.4-0.5	8
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
0.5806	Remote Similarity	NPD8033	Approved

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