NPASS Compound

Natural Product: NPC229073

Natural Product ID	NPC229073
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MFIXLWYJTVEVGO-MDRUUOAKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6324832
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 -7.7290 0.7861 0.7540 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4667 0.0019 1.0669 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8766 0.4029 2.3942 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3732 0.2028 2.4639 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9587 -0.9225 1.4929 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4826 -1.1547 1.6570 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7987 -1.8067 0.4709 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1525 -1.2128 -0.8438 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0102 -2.2620 -1.5974 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0141 -0.0468 -0.5203 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6055 1.1635 -0.7320 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2914 1.6099 -1.2947 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3963 0.4736 -1.6199 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9504 0.4847 -0.9628 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6605 1.7058 -1.5592 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9977 0.7623 0.5111 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0838 0.0189 1.2362 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3636 -0.2236 0.4841 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1563 -0.7634 -0.9104 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9700 -0.1263 -1.9740 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5408 -2.2634 -0.9652 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -0.7984 -1.1393 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2186 -1.4634 -2.3888 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1673 -1.9870 -2.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0910 -0.8319 -1.8022 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9105 -0.7391 -3.1334 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2701 0.8182 0.5764 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3932 0.5615 1.3040 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6336 0.6157 0.4454 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5788 1.7084 0.8287 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7505 1.9698 2.2745 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7365 1.2057 3.0637 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5146 1.3452 2.4467 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0362 1.6920 2.7416 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2385 2.9029 0.1524 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3253 -0.6026 0.4252 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3058 -0.4171 0.1086 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4191 0.5336 0.0459 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0301 0.4742 -1.3547 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2365 1.8218 0.4720 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6951 -2.1029 1.9639 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3950 -2.0617 3.0475 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7365 -3.3468 1.3479 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7247 1.7987 1.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8782 0.9296 -0.3362 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6263 0.2027 1.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6705 -1.0497 0.9234 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0280 1.5245 2.4512 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4294 -0.0207 3.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7893 1.1084 2.3297 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1598 -0.2000 3.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0345 -0.1878 1.9517 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3456 -1.8351 2.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7269 -1.8343 0.7254 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1185 -2.8690 0.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7415 -1.8079 -2.2572 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2567 -2.9245 -2.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5248 -2.9458 -0.9272 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3374 1.9574 -0.4576 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5810 2.2585 -2.1742 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8957 2.3365 -0.5657 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1293 0.7243 -2.7201 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8419 2.4884 -1.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3952 2.1498 -0.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9548 1.5488 -2.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0439 1.8425 0.7614 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0521 0.4022 0.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3499 0.6222 2.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7108 -0.9562 1.6443 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8641 -1.0562 1.0739 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5120 -0.2218 -2.9944 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2448 0.9253 -1.7517 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9767 -0.6341 -2.1093 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7907 -2.5329 -2.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4546 -2.4404 -0.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7504 -2.8901 -0.5580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3454 -1.4748 -0.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1214 -0.7320 -3.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8855 -2.3096 -2.6979 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4410 -2.6139 -2.9403 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0619 -2.6333 -1.1690 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2509 -0.0832 -3.7817 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8198 -0.1601 -2.9859 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9724 -1.6803 -3.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3205 -0.4862 1.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3354 0.8099 -0.6055 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5908 1.4395 0.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5602 3.0571 2.4839 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6547 1.7035 4.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0142 0.1597 3.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5491 2.5224 2.8791 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4667 3.3311 0.6439 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2842 -0.4922 0.3141 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6611 -1.3357 -0.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2059 0.2146 -2.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4322 1.4315 -1.6840 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7342 -0.3761 -1.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7318 2.4812 -0.0814 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7185 -4.1677 1.9210 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 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 18 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 31 34 1 0 30 35 1 0 29 36 1 0 10 37 1 0 37 38 1 0 38 39 1 0 38 40 1 1 5 41 1 1 41 42 2 0 41 43 1 0 38 2 1 0 37 5 1 0 25 8 1 0 33 28 1 0 25 13 1 0 22 14 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 6 52 1 0 6 53 1 0 7 54 1 0 7 55 1 0 9 56 1 0 9 57 1 0 9 58 1 0 11 59 1 0 12 60 1 0 12 61 1 0 13 62 1 0 15 63 1 0 15 64 1 0 15 65 1 0 16 66 1 0 16 67 1 0 17 68 1 0 17 69 1 0 18 70 1 1 20 71 1 0 20 72 1 0 20 73 1 0 21 74 1 0 21 75 1 0 21 76 1 0 22 77 1 0 23 78 1 0 23 79 1 0 24 80 1 0 24 81 1 0 26 82 1 0 26 83 1 0 26 84 1 0 28 85 1 1 29 86 1 6 30 87 1 6 31 88 1 6 32 89 1 0 32 90 1 0 34 91 1 0 35 92 1 0 36 93 1 0 37 94 1 6 39 95 1 0 39 96 1 0 39 97 1 0 40 98 1 0 43 99 1 0 M END

Standard InCHIKey	MFIXLWYJTVEVGO-MDRUUOAKSA-N
Standard InCHI	InChI=1S/C35H56O8/c1-19-10-15-35(29(39)40)17-16-32(5)20(27(35)34(19,7)41)8-9-23-31(4)13-12-24(30(2,3)22(31)11-14-33(23,32)6)43-28-26(38)25(37)21(36)18-42-28/h8,19,21-28,36-38,41H,9-18H2,1-7H3,(H,39,40)/t19?,21-,22?,23?,24+,25+,26-,27-,28+,31+,32?,33-,34-,35+/m1/s1
SMILES	CC1CC[C@@]2(CCC3(C)C(=CCC4[C@@]5(C)CC[C@@H](C(C)(C)C5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)[C@@H]2[C@]1(C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	604.4	Volume:	627.626 ? Van der Waals volume.
Dense:	0.963	LogP:	3.119 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.131 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.012 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	33.0
TPSA:	136.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.232	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.347	Fsp³:	0.914
MCE-18:	129.075 ? 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:	0.84	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? 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:	0.138	Promiscuous compounds:	0.071

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.714	MDCK Permeability:	-5.133
Pgp-inhibitor:	0.001	Pgp-substrate:	0.01
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):	0.0
20% Bioavailability (F20%):	0.028	30% Bioavailability (F30%):	0.015
50% Bioavailability (F50%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.982
Plasma Protein Binding (PPB):	76.866%	Volume Distribution (VD):	-0.531
Fu:	16.069% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.938	BCRP inhibitor:	0.0
BSEP inhibitor:	0.87

ADMET: Metabolism

CYP1A2-inhibitor:	0.013	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.393	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.889	CYP3A4-substrate:	0.12
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

0.847

Half-life (T1/2):

1.655

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.041
Human Hepatotoxicity (H-HT):	0.858	Drug-induced Liver Injury (DILI):	0.163
AMES Toxicity:	0.134	Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.442	Skin Sensitization:	0.991
Carcinogencity:	0.544	Eye Corrosion:	0.0
Eye Irritation:	0.062	Respiratory Toxicity:	0.231
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.963
Hematotoxicity:	0.065	Drug-induced Nephrotoxicity:	0.907
Genotoxicity:	0.121	RPMI-8226 Immunitoxicity:	0.051
A549 Cytotoxicity:	0.208	Hek293 Cytotoxicity:	0.275
BCF:	1.658 ? 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:	4.502 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.951 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.271 ? 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
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	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 NPC229073 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	18970
0.1-0.2	25689
0.2-0.3	3782
0.3-0.4	918
0.4-0.5	368
0.5-0.6	98
0.6-0.7	25
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
0.7683	Intermediate Similarity	NPC283849
0.6977	Remote Similarity	NPC177246
0.686	Remote Similarity	NPC28198
0.686	Remote Similarity	NPC476123
0.6818	Remote Similarity	NPC242611
0.6809	Remote Similarity	NPC6377
0.6809	Remote Similarity	NPC208381
0.6629	Remote Similarity	NPC100383
0.6548	Remote Similarity	NPC233012
0.65	Remote Similarity	NPC202728
0.65	Remote Similarity	NPC158059
0.6458	Remote Similarity	NPC488561
0.6364	Remote Similarity	NPC104400
0.6364	Remote Similarity	NPC10320
0.6353	Remote Similarity	NPC327179
0.6327	Remote Similarity	NPC469945
0.6296	Remote Similarity	NPC136697
0.622	Remote Similarity	NPC191412
0.622	Remote Similarity	NPC114159
0.622	Remote Similarity	NPC6818
0.6111	Remote Similarity	NPC606107
0.6078	Remote Similarity	NPC481082
0.6078	Remote Similarity	NPC73829
0.6078	Remote Similarity	NPC164419
0.6071	Remote Similarity	NPC187933
0.6019	Remote Similarity	NPC79718
0.5978	Remote Similarity	NPC286347
0.5977	Remote Similarity	NPC96693
0.5977	Remote Similarity	NPC54909
0.596	Remote Similarity	NPC488516
0.5952	Remote Similarity	NPC148964
0.5918	Remote Similarity	NPC56713
0.5904	Remote Similarity	NPC259733
0.5904	Remote Similarity	NPC158371
0.5904	Remote Similarity	NPC207922
0.5888	Remote Similarity	NPC280941
0.5888	Remote Similarity	NPC235772
0.5859	Remote Similarity	NPC127056
0.5833	Remote Similarity	NPC204458
0.5833	Remote Similarity	NPC132824
0.5833	Remote Similarity	NPC247139
0.5773	Remote Similarity	NPC127853
0.5765	Remote Similarity	NPC62516
0.5747	Remote Similarity	NPC603658
0.5714	Remote Similarity	NPC256247
0.5714	Remote Similarity	NPC488515
0.5698	Remote Similarity	NPC157113
0.5647	Remote Similarity	NPC35239
0.5591	Remote Similarity	NPC57362
0.5545	Remote Similarity	NPC114441
0.5536	Remote Similarity	NPC471384
0.5514	Remote Similarity	NPC37134
0.551	Remote Similarity	NPC90856
0.551	Remote Similarity	NPC473481
0.55	Remote Similarity	NPC482052
0.5487	Remote Similarity	NPC166422
0.5484	Remote Similarity	NPC204407
0.5474	Remote Similarity	NPC31839
0.5465	Remote Similarity	NPC118519
0.5463	Remote Similarity	NPC75318
0.5455	Remote Similarity	NPC164194
0.5446	Remote Similarity	NPC25491
0.5437	Remote Similarity	NPC22956
0.5435	Remote Similarity	NPC600756
0.5421	Remote Similarity	NPC484832
0.5421	Remote Similarity	NPC119794
0.5413	Remote Similarity	NPC477193
0.5412	Remote Similarity	NPC235053
0.5402	Remote Similarity	NPC137072
0.5402	Remote Similarity	NPC118964
0.537	Remote Similarity	NPC145899
0.5361	Remote Similarity	NPC128925
0.5354	Remote Similarity	NPC189884
0.5354	Remote Similarity	NPC138334
0.5347	Remote Similarity	NPC136877
0.5341	Remote Similarity	NPC284865
0.534	Remote Similarity	NPC472949
0.534	Remote Similarity	NPC482051
0.5321	Remote Similarity	NPC324875
0.5321	Remote Similarity	NPC292677
0.5306	Remote Similarity	NPC284807
0.5294	Remote Similarity	NPC174679
0.5294	Remote Similarity	NPC25605
0.5294	Remote Similarity	NPC279554
0.5294	Remote Similarity	NPC108748
0.5294	Remote Similarity	NPC59804
0.5288	Remote Similarity	NPC80843
0.5287	Remote Similarity	NPC485589
0.5283	Remote Similarity	NPC180550
0.5283	Remote Similarity	NPC35405
0.5273	Remote Similarity	NPC488209
0.5268	Remote Similarity	NPC288205
0.5268	Remote Similarity	NPC51465
0.5243	Remote Similarity	NPC109079
0.5225	Remote Similarity	NPC477194
0.5221	Remote Similarity	NPC200788
0.52	Remote Similarity	NPC480938
0.5185	Remote Similarity	NPC257468
0.5182	Remote Similarity	NPC291903
0.5179	Remote Similarity	NPC11242
0.5172	Remote Similarity	NPC475140
0.5172	Remote Similarity	NPC120840
0.5169	Remote Similarity	NPC147232
0.5152	Remote Similarity	NPC294112
0.5149	Remote Similarity	NPC1046
0.5149	Remote Similarity	NPC78046
0.5133	Remote Similarity	NPC475119
0.513	Remote Similarity	NPC243680
0.51	Remote Similarity	NPC191410
0.5096	Remote Similarity	NPC480424
0.5096	Remote Similarity	NPC482049
0.5096	Remote Similarity	NPC482050
0.5094	Remote Similarity	NPC75417
0.5093	Remote Similarity	NPC481234
0.5093	Remote Similarity	NPC479431
0.5089	Remote Similarity	NPC187290
0.5088	Remote Similarity	NPC473824
0.5086	Remote Similarity	NPC219180
0.5055	Remote Similarity	NPC485586
0.5055	Remote Similarity	NPC485588
0.5047	Remote Similarity	NPC114304
0.5045	Remote Similarity	NPC301449
0.5045	Remote Similarity	NPC601290
0.5044	Remote Similarity	NPC62725

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC229073 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6074
0.1-0.2	3000
0.2-0.3	64
0.3-0.4	10
0.4-0.5	1
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
0.56	Remote Similarity	NPD8295	Clinical (unspecified phase)

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