NPASS Compound

Natural Product: NPC309680

Natural Product ID	NPC309680
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CDJCQFDFKCXDKX-GABHVDRYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6324954
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 93 99 0 0 0 0 0 0 0 0999 V2000 -7.8012 -1.4295 -2.3125 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0486 -0.1190 -2.4931 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4813 0.9167 -1.5400 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4071 1.6614 -0.8307 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0953 0.9419 -0.7207 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0095 -0.1228 0.2823 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3104 -0.4585 0.9885 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0746 0.3782 1.3182 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8853 1.8183 0.9476 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4966 2.1201 1.3792 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9064 0.8312 1.9604 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4261 0.8247 1.7425 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2652 -0.1153 2.6584 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6300 -0.5316 2.3147 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0213 -0.4896 0.8706 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5312 -0.3145 0.8541 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1323 -0.0322 -0.4538 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1798 0.1450 -1.5971 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9079 0.8498 -1.2468 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4322 0.6639 0.1487 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8506 1.9275 0.9195 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0606 0.6014 0.2811 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6842 -0.7013 -0.0934 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2022 -0.4469 -0.1039 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6873 -0.2339 1.2874 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7878 -1.5205 2.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9351 0.4181 -2.1770 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0231 -1.0515 -0.7861 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3386 -0.6255 -0.8997 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2494 -1.3065 0.0928 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5246 -0.4675 0.1813 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8666 -0.0190 -1.2126 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2017 -0.8975 -2.2241 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8252 -0.7935 -2.1982 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4511 1.3042 -1.4379 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5593 -1.1830 0.7763 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6522 -1.3762 1.3455 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7577 -1.7220 0.2979 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1416 1.9326 -0.3842 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7760 0.5510 -2.0193 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5932 -0.4303 -2.5193 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1839 -2.1802 -1.7658 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2367 -1.8118 -3.2340 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6520 -1.1993 -1.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3280 0.2280 -3.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1324 0.4294 -0.7573 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1771 1.6673 -2.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1889 2.5828 -1.4531 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7488 2.0827 0.1466 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6186 -1.1061 -0.0860 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8646 -1.2282 0.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9977 -0.9743 1.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8887 0.4077 1.2955 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4424 0.2776 2.3635 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6526 2.4173 1.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5557 2.8271 2.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8516 2.5827 0.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0800 0.7711 3.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0736 1.8638 1.9838 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2853 0.3766 3.6776 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3921 -1.0023 2.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7734 -1.6025 2.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3859 0.0166 2.9554 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9221 -1.2754 1.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7886 0.4605 1.6345 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7711 0.8960 -0.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7255 0.7145 -2.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9710 -0.8392 -2.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0539 1.9271 -1.4787 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9626 1.7567 1.9792 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1726 2.7689 0.6445 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8641 2.2367 0.5281 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4940 1.4018 -0.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5315 -1.4712 0.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4528 -1.0956 -1.0753 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3162 0.5065 -0.6608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6703 -1.3023 -0.6319 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8077 -1.9527 1.8852 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0841 -2.3023 1.7177 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7407 -1.3399 3.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0770 0.8193 -3.0633 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3580 0.4616 -0.6812 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4920 -2.3472 -0.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2707 0.4193 0.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9667 -0.0955 -1.3643 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5567 -1.9462 -2.1076 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5294 -0.5788 -3.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0863 1.8684 -0.9090 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4817 -2.1609 0.6016 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2654 -2.2742 1.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5434 -2.1669 -0.0820 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3549 -1.3817 -1.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2454 -0.6312 -3.5651 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 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 19 27 1 0 17 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 32 35 1 0 31 36 1 0 30 37 1 0 15 38 1 6 9 39 1 0 5 40 1 0 40 41 1 0 41 2 1 0 39 5 1 0 25 8 1 0 34 29 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 6 50 1 0 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 0 9 55 1 0 10 56 1 0 10 57 1 0 11 58 1 0 12 59 1 0 13 60 1 0 13 61 1 0 14 62 1 0 14 63 1 0 16 64 1 0 16 65 1 0 17 66 1 1 18 67 1 0 18 68 1 0 19 69 1 6 21 70 1 0 21 71 1 0 21 72 1 0 22 73 1 0 23 74 1 0 23 75 1 0 24 76 1 0 24 77 1 0 26 78 1 0 26 79 1 0 26 80 1 0 27 81 1 0 29 82 1 1 30 83 1 6 31 84 1 1 32 85 1 1 33 86 1 0 33 87 1 0 35 88 1 0 36 89 1 0 37 90 1 0 38 91 1 0 41 92 1 0 41 93 1 0 M END

Standard InCHIKey	CDJCQFDFKCXDKX-GABHVDRYSA-N
Standard InCHI	InChI=1S/C32H52O9/c1-16-5-10-32(39-14-16)17(2)25-23(41-32)12-21-19-6-9-31(37)13-18(40-28-27(36)26(35)22(33)15-38-28)11-24(34)30(31,4)20(19)7-8-29(21,25)3/h16-28,33-37H,5-15H2,1-4H3/t16?,17?,18-,19?,20?,21?,22+,23?,24+,25?,26-,27+,28-,29?,30?,31-,32?/m0/s1
SMILES	CC1CCC2(C(C)C3C(CC4C5CC[C@@]6(C[C@H](C[C@H](C6(C)C5CCC34C)O)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	580.36	Volume:	581.245 ? Van der Waals volume.
Dense:	0.998	LogP:	2.163 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.766 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.325 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	36.0
TPSA:	138.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	7.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.312	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.062	Fsp³:	1.0
MCE-18:	178.25 ? 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:	0.44	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.025 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.113	Promiscuous compounds:	0.055

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.405	MDCK Permeability:	-5.03
Pgp-inhibitor:	0.0	Pgp-substrate:	0.979
PAMPA:	0.994 ? 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%):	0.162	30% Bioavailability (F30%):	0.088
50% Bioavailability (F50%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156	MRP1:	0.967
Plasma Protein Binding (PPB):	59.582%	Volume Distribution (VD):	-0.194
Fu:	43.3% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.977
OATP1B3 inhibitor:	0.972	BCRP inhibitor:	0.022
BSEP inhibitor:	0.879

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.691	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.067	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.024
HLM stability:	0.843 ? 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):

8.394

Half-life (T1/2):

3.224

ADMET: Toxicity

hERG Blockers:	0.123	hERG Blockers (10um):	0.298
Human Hepatotoxicity (H-HT):	0.606	Drug-induced Liver Injury (DILI):	0.06
AMES Toxicity:	0.3	Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.757	Skin Sensitization:	0.943
Carcinogencity:	0.179	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.418
Drug-induced Neurotoxicity:	0.023	Ototoxicity:	0.98
Hematotoxicity:	0.044	Drug-induced Nephrotoxicity:	0.287
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.207
A549 Cytotoxicity:	0.499	Hek293 Cytotoxicity:	0.481
BCF:	1.42 ? 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:	3.741 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.246 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.347 ? 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
NPO23518	Polygonatum odoratum	Species	Asparagaceae	Eukaryota	fibrous roots	n.a.	n.a.	PMID[20158245]
NPO23518	Polygonatum odoratum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23639538]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23518	Polygonatum odoratum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23518	Polygonatum odoratum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23518	Polygonatum odoratum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23518	Polygonatum odoratum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23518	Polygonatum odoratum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23518	Polygonatum odoratum	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 NPC309680 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	25899
0.1-0.2	21944
0.2-0.3	1698
0.3-0.4	155
0.4-0.5	107
0.5-0.6	43
0.6-0.7	4
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
0.631	Remote Similarity	NPC88962
0.6279	Remote Similarity	NPC481418
0.6264	Remote Similarity	NPC250393
0.6111	Remote Similarity	NPC177834
0.5895	Remote Similarity	NPC264101
0.5699	Remote Similarity	NPC485591
0.5686	Remote Similarity	NPC471464
0.5579	Remote Similarity	NPC312678
0.5579	Remote Similarity	NPC253268
0.5446	Remote Similarity	NPC475351
0.5429	Remote Similarity	NPC97700
0.5429	Remote Similarity	NPC30856
0.5421	Remote Similarity	NPC475625
0.5408	Remote Similarity	NPC485590
0.5333	Remote Similarity	NPC128572
0.5319	Remote Similarity	NPC481423
0.5263	Remote Similarity	NPC325828
0.5229	Remote Similarity	NPC232037
0.5213	Remote Similarity	NPC485594
0.5152	Remote Similarity	NPC211354
0.5152	Remote Similarity	NPC107188
0.514	Remote Similarity	NPC294129
0.5138	Remote Similarity	NPC475333
0.5138	Remote Similarity	NPC224098
0.5138	Remote Similarity	NPC208383
0.5135	Remote Similarity	NPC476112
0.5135	Remote Similarity	NPC307534
0.5116	Remote Similarity	NPC52585
0.5104	Remote Similarity	NPC297348
0.5104	Remote Similarity	NPC249204
0.5104	Remote Similarity	NPC48339
0.5104	Remote Similarity	NPC141769
0.5104	Remote Similarity	NPC13190
0.5104	Remote Similarity	NPC477547
0.5096	Remote Similarity	NPC473601
0.5089	Remote Similarity	NPC132080
0.5057	Remote Similarity	NPC68630
0.5055	Remote Similarity	NPC144790
0.5055	Remote Similarity	NPC149400
0.5054	Remote Similarity	NPC481420
0.5054	Remote Similarity	NPC473774
0.5054	Remote Similarity	NPC481419
0.5054	Remote Similarity	NPC481417
0.5054	Remote Similarity	NPC481421
0.5052	Remote Similarity	NPC234352
0.505	Remote Similarity	NPC107962
0.505	Remote Similarity	NPC215408

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC309680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7647
0.1-0.2	1457
0.2-0.3	39
0.3-0.4	3
0.4-0.5	2
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
0.5263	Remote Similarity	NPD8171	Phase 2

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