NPASS Compound

Natural Product: NPC105731

Natural Product ID	NPC105731
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZJELZQKROOYPAX-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	545613
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

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 111110 0 0 0 0 0 0 0 0999 V2000 -12.3428 2.1212 -2.1312 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8959 0.7935 -2.5491 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0194 -0.3758 -2.1461 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8857 -0.3434 -0.6037 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0407 -1.4538 -0.1225 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8220 -1.4946 1.3299 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9663 -0.4625 1.9259 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2684 0.9642 1.7601 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2945 1.8422 2.5789 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8583 1.5906 2.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6145 1.8479 0.7089 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1703 1.6201 0.3216 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7991 0.2087 0.6519 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3878 -0.0673 0.2049 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4389 0.8807 0.8597 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0130 0.5680 0.4299 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8074 0.6196 -1.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3502 0.3173 -1.3387 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0073 -0.9026 -0.8266 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2876 -1.3183 -1.0668 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5913 -1.5370 -2.5070 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9109 -1.9550 -2.7496 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5118 -3.0828 -2.2189 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8412 -3.8284 -1.4253 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8922 -3.4990 -2.5061 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5713 -4.0382 -1.2950 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8696 -3.0566 -0.2053 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7721 -2.3306 0.4299 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0678 -1.4070 1.5486 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8919 -0.2152 1.4037 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3202 -0.2919 1.0146 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8325 1.1758 1.0444 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2655 1.2363 0.6447 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1144 0.4440 1.5727 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5602 0.5134 1.1723 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0379 1.9363 1.2131 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5293 2.0048 0.8418 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7747 1.4767 -0.5385 C 0 0 0 0 0 0 0 0 0 0 0 0 15.2767 1.5999 -0.7916 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2628 2.2386 -2.2635 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8705 2.9336 -2.6880 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6257 2.3103 -1.0577 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9043 0.6681 -2.1299 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9681 0.7861 -3.6749 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5631 -1.3008 -2.3965 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0411 -0.3286 -2.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6542 0.6762 -0.3704 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9532 -0.5869 -0.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0660 -1.3881 -0.7021 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4381 -2.4644 -0.4824 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4674 -2.5382 1.6647 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8326 -1.4057 1.8836 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9186 -0.6337 1.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8555 -0.7338 3.0329 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0715 1.3196 0.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2767 1.2582 2.0340 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3805 1.6680 3.6521 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5399 2.8877 2.3207 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5755 0.5601 2.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2288 2.2788 2.7570 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1992 1.1612 0.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8834 2.9154 0.4969 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9841 1.8647 -0.7342 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5777 2.3286 0.9427 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7947 0.0619 1.7745 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5075 -0.5354 0.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1067 -1.0995 0.5104 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3507 0.0022 -0.9151 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6576 1.9427 0.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4763 0.6407 1.9632 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7995 -0.4598 0.7807 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3152 1.2562 0.9036 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0693 1.6695 -1.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4765 -0.0507 -1.6329 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1120 0.4581 -2.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2337 1.0937 -0.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4184 -2.2672 -0.5121 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0384 -0.6039 -0.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9343 -2.3387 -2.9589 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4159 -0.6424 -3.1407 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8646 -4.3361 -3.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4832 -2.6768 -2.9879 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9862 -4.9263 -0.8824 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5577 -4.5106 -1.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3884 -3.6655 0.6029 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6503 -2.3791 -0.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0599 -3.1098 0.8557 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1086 -1.7857 -0.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3921 -2.0543 2.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0409 -1.0509 1.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3811 0.5673 0.7348 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8823 0.3385 2.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8847 -0.8081 1.8242 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5616 -0.6019 0.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7231 1.5109 2.0937 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1802 1.7366 0.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5665 2.3160 0.6849 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4077 0.8231 -0.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8133 -0.6486 1.5654 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0592 0.8146 2.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6531 0.0638 0.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1650 -0.0899 1.8999 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5031 2.6063 0.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8887 2.3696 2.2237 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0946 1.3764 1.5834 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8962 3.0335 0.9878 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2907 2.0967 -1.3159 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4620 0.4210 -0.6549 H 0 0 0 0 0 0 0 0 0 0 0 0 15.5874 0.7856 -1.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7786 1.4644 0.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 15.5162 2.6160 -1.1961 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 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 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 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 37 38 1 0 38 39 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 4 47 1 0 4 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 0 8 56 1 0 9 57 1 0 9 58 1 0 10 59 1 0 10 60 1 0 11 61 1 0 11 62 1 0 12 63 1 0 12 64 1 0 13 65 1 0 13 66 1 0 14 67 1 0 14 68 1 0 15 69 1 0 15 70 1 0 16 71 1 0 16 72 1 0 17 73 1 0 17 74 1 0 18 75 1 0 18 76 1 0 20 77 1 0 20 78 1 0 21 79 1 0 21 80 1 0 25 81 1 0 25 82 1 0 26 83 1 0 26 84 1 0 27 85 1 0 27 86 1 0 28 87 1 0 28 88 1 0 29 89 1 0 29 90 1 0 30 91 1 0 30 92 1 0 31 93 1 0 31 94 1 0 32 95 1 0 32 96 1 0 33 97 1 0 33 98 1 0 34 99 1 0 34100 1 0 35101 1 0 35102 1 0 36103 1 0 36104 1 0 37105 1 0 37106 1 0 38107 1 0 38108 1 0 39109 1 0 39110 1 0 39111 1 0 M END

Standard InCHIKey	ZJELZQKROOYPAX-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C36H72O3/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-33-38-34-35-39-36(37)32-30-28-26-24-22-20-16-14-12-10-8-6-4-2/h3-35H2,1-2H3
SMILES	CCCCCCCCCCCCCCCCCCOCCOC(=O)CCCCCCCCCCCCCCC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.55	Volume:	654.946 ? Van der Waals volume.
Dense:	0.844	LogP:	8.309 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.688 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.94 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	35.0	Rigid Bonds:	1.0
TPSA:	35.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.059	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.128	Fsp³:	0.972
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.6	Fluc inhibitor:	0.286 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.019 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.99	Promiscuous compounds:	0.079

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.134	MDCK Permeability:	-4.929
Pgp-inhibitor:	0.0	Pgp-substrate:	0.09
PAMPA:	0.0 ? 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):	0.995
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.997
Plasma Protein Binding (PPB):	104.286%	Volume Distribution (VD):	2.718
Fu:	0.127% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.231
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.995
BSEP inhibitor:	0.981

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.318
CYP2C9-inhibitor:	0.912	CYP2C9-substrate:	0.53
CYP2D6-inhibitor:	0.943	CYP2D6-substrate:	0.329
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.086	CYP2C8-inhibitor:	1.0
HLM stability:	0.088 ? 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):

4.593

Half-life (T1/2):

3.297

ADMET: Toxicity

hERG Blockers:	0.929	hERG Blockers (10um):	0.977
Human Hepatotoxicity (H-HT):	0.31	Drug-induced Liver Injury (DILI):	0.046
AMES Toxicity:	0.007	Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.112	Skin Sensitization:	0.999
Carcinogencity:	0.299	Eye Corrosion:	0.987
Eye Irritation:	0.99	Respiratory Toxicity:	0.979
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.107
Hematotoxicity:	0.036	Drug-induced Nephrotoxicity:	0.181
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.917	Hek293 Cytotoxicity:	0.292
BCF:	-0.31 ? 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:	5.402 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.939 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.04 ? 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
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26359402]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	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 NPC105731 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	24590
0.1-0.2	23484
0.2-0.3	1531
0.3-0.4	166
0.4-0.5	47
0.5-0.6	34
0.6-0.7	5
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
0.7097	Intermediate Similarity	NPC149299
0.6774	Remote Similarity	NPC80396
0.625	Remote Similarity	NPC154642
0.625	Remote Similarity	NPC80641
0.625	Remote Similarity	NPC603612
0.6129	Remote Similarity	NPC223249
0.5938	Remote Similarity	NPC154396
0.5806	Remote Similarity	NPC250028
0.5806	Remote Similarity	NPC236579
0.5806	Remote Similarity	NPC80234
0.5806	Remote Similarity	NPC203531
0.5806	Remote Similarity	NPC256163
0.5806	Remote Similarity	NPC40597
0.5556	Remote Similarity	NPC152008
0.5556	Remote Similarity	NPC605028
0.5455	Remote Similarity	NPC286695
0.5429	Remote Similarity	NPC26253
0.5312	Remote Similarity	NPC86545
0.5312	Remote Similarity	NPC286498
0.5312	Remote Similarity	NPC223374
0.5312	Remote Similarity	NPC196442
0.5312	Remote Similarity	NPC301398
0.5312	Remote Similarity	NPC608162
0.5312	Remote Similarity	NPC609004
0.5278	Remote Similarity	NPC488257
0.5278	Remote Similarity	NPC469937
0.5278	Remote Similarity	NPC94699
0.5278	Remote Similarity	NPC320588
0.5278	Remote Similarity	NPC53463
0.5263	Remote Similarity	NPC223677
0.5172	Remote Similarity	NPC99700
0.5161	Remote Similarity	NPC53541
0.5152	Remote Similarity	NPC322892
0.5152	Remote Similarity	NPC12904
0.5152	Remote Similarity	NPC476550
0.5143	Remote Similarity	NPC310746
0.5143	Remote Similarity	NPC223675
0.5143	Remote Similarity	NPC68577
0.5135	Remote Similarity	NPC163345
0.5135	Remote Similarity	NPC71761

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC105731 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6415
0.1-0.2	2561
0.2-0.3	144
0.3-0.4	22
0.4-0.5	5
0.5-0.6	3
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
0.5556	Remote Similarity	NPD7536	Phase 4
0.5385	Remote Similarity	NPD631	Phase 4
0.525	Remote Similarity	NPD630	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