NPASS Compound

Natural Product: NPC113941

Natural Product ID	NPC113941
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HAPQAPVIZTWVQY-KDYKUWAWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6325913
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 108114 0 0 0 0 0 0 0 0999 V2000 4.7830 0.5331 -1.9073 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0906 -0.5466 -0.9079 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8958 0.0210 0.2372 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5000 -0.8000 1.4645 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0956 -0.4379 1.8171 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2630 -0.5114 0.5324 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9470 -1.2063 -0.4619 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0856 -1.2217 0.7698 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9319 -0.4660 0.5653 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1685 -0.4175 1.8403 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3037 -0.7022 1.6866 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8898 -0.0298 0.4629 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4897 1.4515 0.5929 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2188 -0.5586 -0.7639 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0172 -1.6287 -1.4569 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3767 -1.1519 -1.9320 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9072 -0.0839 -1.0336 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3685 -0.1434 0.3878 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9886 -1.2491 1.1892 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3163 -1.7063 0.6546 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1234 -0.5691 0.1053 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4798 0.3943 1.1931 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3901 -1.1540 -0.4967 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5409 -1.2306 0.3782 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7255 -0.6902 0.1919 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5840 -1.0200 1.3169 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7794 -0.6664 1.4678 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8796 -1.7910 2.2084 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5695 -1.9363 1.6842 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5568 -0.3290 -1.7492 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0750 -0.5052 -2.2564 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3939 0.0916 -1.0468 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7368 1.4435 -1.0082 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7760 1.0335 -1.5347 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6855 1.7242 -2.2925 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3475 1.1576 -3.1992 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8699 3.1845 -2.0076 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1670 -1.0805 -0.5582 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0698 0.8572 2.2814 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3977 -0.5874 2.5012 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2428 -0.0753 0.1159 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9490 1.1116 0.2724 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9499 1.0826 1.3612 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2387 1.7475 0.9361 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8134 1.0707 -0.2980 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6871 0.7798 -1.2782 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5029 -0.7138 -1.3209 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5203 -1.0854 -2.2519 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5255 1.3821 -0.9381 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6861 1.9665 -0.9035 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1473 1.6010 1.9774 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5466 1.7693 2.5101 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5761 0.6400 -2.6880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8376 0.3675 -2.4608 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6815 1.5435 -1.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6963 -1.3289 -1.4491 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5218 1.0535 0.4509 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5299 -1.8698 1.1276 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7324 -1.1771 2.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9818 0.5027 0.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3084 0.5502 0.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6443 -1.0914 2.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3183 0.6175 2.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3958 -1.8110 1.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8067 -0.2523 2.5678 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2564 1.7293 1.6221 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3984 2.0681 0.3198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7328 1.7327 -0.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1169 0.3058 -1.4867 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1723 -2.5131 -0.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3862 -1.9670 -2.3308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1841 -0.6846 -2.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0602 -2.0060 -2.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5018 0.8821 -1.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7831 0.8044 0.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1335 -0.9776 2.2567 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3492 -2.1772 1.2262 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8737 -2.1658 1.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2041 -2.5418 -0.0889 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0815 1.4335 0.9917 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1317 0.1298 2.1901 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5875 0.5652 1.2659 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1290 -2.1955 -0.8599 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0692 -0.0838 -0.6614 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3068 -3.0096 1.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8799 -1.4908 2.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1740 -0.8102 -2.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0040 -1.6023 -2.3255 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9290 0.0460 -3.1789 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9388 2.0063 -0.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5922 3.3902 -0.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9442 3.4042 -2.1448 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2245 3.7526 -2.6827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1289 -2.1995 -0.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7988 -0.9533 -1.4861 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1034 1.0985 2.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8647 -0.5916 3.3400 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2461 1.9671 0.4749 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1253 0.0370 1.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0356 2.8197 0.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3792 0.1744 -0.0077 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9978 1.0675 -2.3233 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2191 -1.1711 -0.3564 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4264 -1.2382 -1.6602 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6780 -2.0344 -2.5491 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3571 2.3280 -1.7476 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9811 2.1024 1.8567 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3627 2.7165 2.2810 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 1 12 14 1 0 14 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 1 21 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 23 30 1 0 30 31 1 0 31 32 1 0 32 33 1 1 30 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 14 38 1 0 5 39 1 0 4 40 1 0 3 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 45 50 1 0 44 51 1 0 43 52 1 0 7 2 1 0 38 9 1 0 49 42 1 0 18 12 1 0 32 21 1 0 32 17 1 0 29 24 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 6 3 57 1 1 4 58 1 6 5 59 1 1 6 60 1 6 9 61 1 0 10 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 13 66 1 0 13 67 1 0 13 68 1 0 14 69 1 6 15 70 1 0 15 71 1 0 16 72 1 0 16 73 1 0 17 74 1 0 18 75 1 0 19 76 1 0 19 77 1 0 20 78 1 0 20 79 1 0 22 80 1 0 22 81 1 0 22 82 1 0 23 83 1 0 25 84 1 0 29 85 1 0 29 86 1 0 30 87 1 0 31 88 1 0 31 89 1 0 33 90 1 0 37 91 1 0 37 92 1 0 37 93 1 0 38 94 1 0 38 95 1 0 39 96 1 0 40 97 1 0 42 98 1 1 43 99 1 1 44100 1 6 45101 1 1 46102 1 6 47103 1 0 47104 1 0 48105 1 0 50106 1 0 51107 1 0 52108 1 0 M END

Standard InCHIKey	HAPQAPVIZTWVQY-KDYKUWAWSA-N
Standard InCHI	InChI=1S/C37H56O15/c1-16-32(52-34-30(44)28(42)27(41)24(14-38)51-34)29(43)31(45)33(48-16)50-20-7-9-35(3)19(12-20)5-6-22-21(35)8-10-36(4)26(18-11-25(40)47-15-18)23(49-17(2)39)13-37(22,36)46/h11,16,19-24,26-34,38,41-46H,5-10,12-15H2,1-4H3/t16-,19+,20?,21?,22?,23?,24+,26?,27+,28-,29-,30+,31+,32-,33-,34-,35-,36+,37-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC1CC[C@@]2(C)[C@H](CCC3C2CC[C@]2(C)C(C4=CC(=O)OC4)C(C[C@]32O)OC(=O)C)C1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.36	Volume:	712.557 ? Van der Waals volume.
Dense:	1.039	LogP:	0.536 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.141 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.948 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	39.0
TPSA:	231.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.133	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.731	Fsp³:	0.892
MCE-18:	137.2 ? 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:	0.543	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.008 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.093	Promiscuous compounds:	0.165

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.27	MDCK Permeability:	-5.17
Pgp-inhibitor:	0.0	Pgp-substrate:	0.317
PAMPA:	0.999 ? 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):	0.028
20% Bioavailability (F20%):	0.054	30% Bioavailability (F30%):	0.296
50% Bioavailability (F50%):	0.836

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028	MRP1:	0.917
Plasma Protein Binding (PPB):	65.061%	Volume Distribution (VD):	-0.504
Fu:	33.744% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.0
BSEP inhibitor:	0.042

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.084	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.025
HLM stability:	0.008 ? 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):

0.974

Half-life (T1/2):

3.23

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.096
Human Hepatotoxicity (H-HT):	0.813	Drug-induced Liver Injury (DILI):	0.541
AMES Toxicity:	0.952	Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.517	Skin Sensitization:	1.0
Carcinogencity:	0.43	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.998
Hematotoxicity:	0.378	Drug-induced Nephrotoxicity:	0.893
Genotoxicity:	0.842	RPMI-8226 Immunitoxicity:	0.442
A549 Cytotoxicity:	0.708	Hek293 Cytotoxicity:	0.841
BCF:	0.466 ? 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:	3.316 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.038 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.094 ? 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
NPO11308	Rohdea japonica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11308	Rohdea japonica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11308	Rohdea japonica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11308	Rohdea japonica	Species	Asparagaceae	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 NPC113941 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	17311
0.1-0.2	26830
0.2-0.3	4726
0.3-0.4	765
0.4-0.5	124
0.5-0.6	51
0.6-0.7	39
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8652	High Similarity	NPC475219
0.8556	High Similarity	NPC488943
0.8556	High Similarity	NPC488942
0.8021	Intermediate Similarity	NPC488945
0.8021	Intermediate Similarity	NPC488946
0.7957	Intermediate Similarity	NPC488938
0.7957	Intermediate Similarity	NPC488937
0.7865	Intermediate Similarity	NPC236973
0.74	Intermediate Similarity	NPC488947
0.7097	Intermediate Similarity	NPC40749
0.6966	Remote Similarity	NPC5311
0.6915	Remote Similarity	NPC32177
0.6915	Remote Similarity	NPC469756
0.6915	Remote Similarity	NPC275901
0.6842	Remote Similarity	NPC188234
0.6771	Remote Similarity	NPC231518
0.6771	Remote Similarity	NPC488944
0.6702	Remote Similarity	NPC5883
0.6701	Remote Similarity	NPC486143
0.6701	Remote Similarity	NPC486142
0.6701	Remote Similarity	NPC486149
0.6526	Remote Similarity	NPC103534
0.6526	Remote Similarity	NPC44899
0.6526	Remote Similarity	NPC488935
0.6526	Remote Similarity	NPC304260
0.6526	Remote Similarity	NPC488936
0.6526	Remote Similarity	NPC29639
0.6458	Remote Similarity	NPC30483
0.6458	Remote Similarity	NPC470897
0.64	Remote Similarity	NPC486146
0.6373	Remote Similarity	NPC479360
0.6373	Remote Similarity	NPC479359
0.6346	Remote Similarity	NPC120390
0.6346	Remote Similarity	NPC74259
0.6311	Remote Similarity	NPC486144
0.6311	Remote Similarity	NPC486145
0.6311	Remote Similarity	NPC486147
0.6311	Remote Similarity	NPC475590
0.6311	Remote Similarity	NPC486148
0.6224	Remote Similarity	NPC292467
0.62	Remote Similarity	NPC208193
0.6196	Remote Similarity	NPC99620
0.6162	Remote Similarity	NPC32793
0.6162	Remote Similarity	NPC116075
0.61	Remote Similarity	NPC488941
0.61	Remote Similarity	NPC488940
0.6064	Remote Similarity	NPC77299
0.6064	Remote Similarity	NPC480906
0.6	Remote Similarity	NPC480914
0.5981	Remote Similarity	NPC474908
0.5981	Remote Similarity	NPC486134
0.5981	Remote Similarity	NPC486141
0.5922	Remote Similarity	NPC488939
0.5918	Remote Similarity	NPC480907
0.5882	Remote Similarity	NPC125077
0.5882	Remote Similarity	NPC486135
0.5882	Remote Similarity	NPC486137
0.5843	Remote Similarity	NPC119855
0.5842	Remote Similarity	NPC479353
0.5842	Remote Similarity	NPC479354
0.5833	Remote Similarity	NPC117445
0.5833	Remote Similarity	NPC308262
0.5825	Remote Similarity	NPC232785
0.5825	Remote Similarity	NPC486139
0.5818	Remote Similarity	NPC474423
0.5784	Remote Similarity	NPC264336
0.5741	Remote Similarity	NPC475419
0.5686	Remote Similarity	NPC240070
0.567	Remote Similarity	NPC76572
0.567	Remote Similarity	NPC193382
0.5657	Remote Similarity	NPC193893
0.56	Remote Similarity	NPC72260
0.5577	Remote Similarity	NPC59288
0.5566	Remote Similarity	NPC486138
0.5566	Remote Similarity	NPC276838
0.5556	Remote Similarity	NPC486136
0.5534	Remote Similarity	NPC480910
0.5534	Remote Similarity	NPC480909
0.5514	Remote Similarity	NPC479357
0.5464	Remote Similarity	NPC84987
0.5408	Remote Similarity	NPC469750
0.5385	Remote Similarity	NPC475556
0.5385	Remote Similarity	NPC311706
0.5361	Remote Similarity	NPC471633
0.5333	Remote Similarity	NPC475629
0.5327	Remote Similarity	NPC329986
0.5327	Remote Similarity	NPC140092
0.5248	Remote Similarity	NPC471353
0.5221	Remote Similarity	NPC486150
0.5135	Remote Similarity	NPC479358
0.51	Remote Similarity	NPC479356
0.51	Remote Similarity	NPC479355
0.5098	Remote Similarity	NPC93883
0.5096	Remote Similarity	NPC173555
0.5094	Remote Similarity	NPC225385
0.5094	Remote Similarity	NPC486130
0.505	Remote Similarity	NPC199428
0.505	Remote Similarity	NPC109448
0.505	Remote Similarity	NPC310341
0.5047	Remote Similarity	NPC486127

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC113941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6595
0.1-0.2	2456
0.2-0.3	79
0.3-0.4	5
0.4-0.5	10
0.5-0.6	4
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	Drug ID	Developmental Stage
0.6771	Remote Similarity	NPD8033	Approved
0.56	Remote Similarity	NPD8294	Phase 4
0.5283	Remote Similarity	NPD8377	Phase 4
0.5098	Remote Similarity	NPD8380	Approved
0.5096	Remote Similarity	NPD8296	Phase 4

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