NPASS Compound

Natural Product: NPC73004

Natural Product ID	NPC73004
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Buergericic Acid
IUPAC Name	(1S,4aR,6aR,6aS,6bR,8aR,9S,10S,11R,12aR,14bS)-1,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	Buergericic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1078652
PubChem CID	46882793
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 84 88 0 0 0 0 0 0 0 0999 V2000 -6.7827 -0.8548 1.5321 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3862 -0.8594 1.5713 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8443 -0.3147 0.2685 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4012 -1.2848 -0.7969 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3974 1.0272 -0.0771 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5388 0.9108 -0.9166 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4258 1.8702 -0.8422 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4760 1.4218 -2.1834 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0608 1.9874 -0.3215 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5913 0.8228 0.5712 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3724 -0.3656 0.1350 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8167 -1.6669 0.7127 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4924 -1.8722 -0.0177 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5920 -0.7627 0.4360 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1371 0.6104 0.3202 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2328 1.5117 1.1509 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1862 1.1918 0.9152 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6261 0.1595 0.1959 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6650 -0.7966 -0.4573 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3579 -0.4021 -1.8603 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2686 -2.1568 -0.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6242 -2.2170 -0.9879 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6163 -1.2251 -0.4654 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1009 0.0242 0.0958 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6683 1.2904 -0.5561 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1752 1.5265 -1.8121 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1820 1.2592 -0.5766 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7277 -0.0254 -1.1056 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5982 -0.8765 -1.5991 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6247 2.3734 -1.5089 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7482 1.6006 0.7990 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4481 -1.9542 0.5213 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4973 -1.5865 1.7090 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1674 -3.0480 0.1012 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0881 -1.1488 1.8082 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8308 1.3067 1.9642 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1211 -0.1413 2.1125 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9724 -0.3775 2.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1167 -1.9519 1.6867 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4216 -2.3109 -0.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7307 -1.3145 -1.6739 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4181 -1.0220 -1.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8203 1.5817 0.8130 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3171 0.6575 -0.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8794 2.9051 -0.8916 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5619 1.3454 -2.5562 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3511 2.0473 -1.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9122 2.9660 0.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1610 -0.4499 -0.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5275 -2.4829 0.5239 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5863 -1.4859 1.7695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7275 -1.8940 -1.0792 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0867 -2.8279 0.3716 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9465 0.9515 -0.7447 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3931 1.3708 2.2474 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5086 2.5539 0.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8961 1.8921 1.3940 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9680 -0.9507 -2.6247 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6919 -0.5333 -2.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5806 0.6859 -2.0651 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6130 -2.8388 -0.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2826 -2.5945 0.6248 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9859 -3.2808 -0.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5676 -2.0998 -2.1006 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4667 0.1203 1.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4091 2.1875 0.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4949 2.2426 -1.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3203 -0.5604 -0.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4172 0.1141 -1.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0668 -1.8569 -1.9134 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1027 -0.4976 -2.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9267 2.5072 -2.3620 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5466 3.3225 -0.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6746 2.2847 -1.8117 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6533 0.9694 1.0220 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1056 2.6509 0.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9773 1.5018 1.5956 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7931 -3.5306 0.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0168 -1.0424 1.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5406 -0.6181 2.6356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2635 -2.2468 2.0229 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1994 2.2418 2.0689 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5735 0.6373 2.7695 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8518 1.6952 2.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 1 3 4 1 0 3 5 1 0 5 6 1 0 5 7 1 0 7 8 1 0 7 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 2 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 27 31 1 0 23 32 1 1 32 33 2 0 32 34 1 0 14 35 1 1 10 36 1 1 11 3 1 0 19 14 1 0 29 23 1 0 15 10 1 0 24 18 1 0 1 37 1 0 2 38 1 0 2 39 1 0 4 40 1 0 4 41 1 0 4 42 1 0 5 43 1 1 6 44 1 0 7 45 1 6 8 46 1 0 9 47 1 0 9 48 1 0 11 49 1 6 12 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 15 54 1 6 16 55 1 0 16 56 1 0 17 57 1 0 20 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 24 65 1 1 25 66 1 1 26 67 1 0 28 68 1 0 28 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 36 82 1 0 36 83 1 0 36 84 1 0 M END

Standard InCHIKey	IFIQVSCCFRXSJV-SBAYXHKCSA-N
Standard InCHI	InChI=1S/C30H48O6/c1-25(2)11-13-30(24(35)36)14-12-28(5)17(21(30)23(25)34)7-8-20-26(3)15-18(32)22(33)27(4,16-31)19(26)9-10-29(20,28)6/h7,18-23,31-34H,8-16H2,1-6H3,(H,35,36)/t18-,19-,20-,21-,22-,23+,26+,27-,28-,29-,30+/m1/s1
SMILES	OC[C@@]1(C)[C@H](O)[C@H](O)C[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@H](O)C(CC1)(C)C)C(=O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.35	Volume:	532.122 ? Van der Waals volume.
Dense:	0.948	LogP:	2.569 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.511 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.167 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	118.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.361	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.094	Fsp³:	0.9
MCE-18:	110.772 ? 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:	0.603	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.062 ? 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:	0.289	Promiscuous compounds:	0.101

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.844	MDCK Permeability:	-5.1
Pgp-inhibitor:	0.0	Pgp-substrate:	0.335
PAMPA:	1.0 ? 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):	0.001
20% Bioavailability (F20%):	0.817	30% Bioavailability (F30%):	0.169
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.472	MRP1:	0.986
Plasma Protein Binding (PPB):	76.588%	Volume Distribution (VD):	-0.283
Fu:	21.555% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.738	BCRP inhibitor:	0.005
BSEP inhibitor:	0.578

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.007
HLM stability:	0.003 ? 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):

2.853

Half-life (T1/2):

1.684

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.047
Human Hepatotoxicity (H-HT):	0.551	Drug-induced Liver Injury (DILI):	0.402
AMES Toxicity:	0.236	Rat Oral Acute Toxicity:	0.234
Maximum Recommended Daily Dose:	0.407	Skin Sensitization:	0.961
Carcinogencity:	0.757	Eye Corrosion:	0.001
Eye Irritation:	0.317	Respiratory Toxicity:	0.845
Drug-induced Neurotoxicity:	0.015	Ototoxicity:	0.864
Hematotoxicity:	0.407	Drug-induced Nephrotoxicity:	0.906
Genotoxicity:	0.538	RPMI-8226 Immunitoxicity:	0.047
A549 Cytotoxicity:	0.078	Hek293 Cytotoxicity:	0.105
BCF:	0.511 ? 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:	3.35 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.994 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.111 ? 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
NPO23655.1	Rubus ellipticus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19795885]
NPO23655.1	Rubus ellipticus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[38455614]
NPO23655.1	Rubus ellipticus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

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
NPT2	Others	Unspecified	n.a.	IC50	=	1800000.0	nM	PMID[24224794]

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 NPC73004 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	23797
0.1-0.2	22631
0.2-0.3	2735
0.3-0.4	428
0.4-0.5	165
0.5-0.6	56
0.6-0.7	23
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC173744
1.0	High Similarity	NPC204961
0.7656	Intermediate Similarity	NPC229281
0.7538	Intermediate Similarity	NPC231063
0.7538	Intermediate Similarity	NPC282395
0.7538	Intermediate Similarity	NPC88116
0.7538	Intermediate Similarity	NPC609452
0.7424	Intermediate Similarity	NPC32407
0.7424	Intermediate Similarity	NPC263548
0.7424	Intermediate Similarity	NPC606320
0.7344	Intermediate Similarity	NPC43686
0.7313	Intermediate Similarity	NPC247139
0.7273	Intermediate Similarity	NPC111214
0.7206	Intermediate Similarity	NPC607666
0.7206	Intermediate Similarity	NPC608261
0.7206	Intermediate Similarity	NPC611078
0.7101	Intermediate Similarity	NPC20235
0.7101	Intermediate Similarity	NPC299996
0.697	Remote Similarity	NPC187722
0.6765	Remote Similarity	NPC38754
0.6761	Remote Similarity	NPC479743
0.6571	Remote Similarity	NPC201657
0.6522	Remote Similarity	NPC73489
0.6522	Remote Similarity	NPC472149
0.6522	Remote Similarity	NPC37221
0.6522	Remote Similarity	NPC110308
0.6471	Remote Similarity	NPC96916
0.6429	Remote Similarity	NPC145667
0.6377	Remote Similarity	NPC194196
0.6377	Remote Similarity	NPC84319
0.6377	Remote Similarity	NPC52021
0.6377	Remote Similarity	NPC599947
0.6338	Remote Similarity	NPC88847
0.6286	Remote Similarity	NPC71074
0.6286	Remote Similarity	NPC605937
0.6197	Remote Similarity	NPC259733
0.6197	Remote Similarity	NPC158371
0.6197	Remote Similarity	NPC207922
0.6111	Remote Similarity	NPC9613
0.6027	Remote Similarity	NPC25299
0.6027	Remote Similarity	NPC481322
0.5972	Remote Similarity	NPC305464
0.5972	Remote Similarity	NPC19376
0.5972	Remote Similarity	NPC25848
0.5915	Remote Similarity	NPC307282
0.5833	Remote Similarity	NPC481314
0.5811	Remote Similarity	NPC481316
0.5753	Remote Similarity	NPC40092
0.5735	Remote Similarity	NPC478657
0.5733	Remote Similarity	NPC116457
0.5694	Remote Similarity	NPC270768
0.5694	Remote Similarity	NPC59263
0.5694	Remote Similarity	NPC210106
0.5694	Remote Similarity	NPC121798
0.5694	Remote Similarity	NPC234346
0.5676	Remote Similarity	NPC191412
0.5676	Remote Similarity	NPC114159
0.5676	Remote Similarity	NPC6818
0.5641	Remote Similarity	NPC188833
0.5641	Remote Similarity	NPC96693
0.5616	Remote Similarity	NPC61543
0.5616	Remote Similarity	NPC293048
0.5616	Remote Similarity	NPC225585
0.5526	Remote Similarity	NPC117663
0.5526	Remote Similarity	NPC481318
0.5455	Remote Similarity	NPC481315
0.5405	Remote Similarity	NPC106112
0.5405	Remote Similarity	NPC261935
0.5405	Remote Similarity	NPC481360
0.5395	Remote Similarity	NPC127689
0.5395	Remote Similarity	NPC130520
0.5333	Remote Similarity	NPC87095
0.5333	Remote Similarity	NPC136697
0.5316	Remote Similarity	NPC481320
0.527	Remote Similarity	NPC182797
0.527	Remote Similarity	NPC306541
0.527	Remote Similarity	NPC52169
0.527	Remote Similarity	NPC488562
0.5263	Remote Similarity	NPC35239
0.525	Remote Similarity	NPC481319
0.5195	Remote Similarity	NPC62516
0.5135	Remote Similarity	NPC480946
0.5135	Remote Similarity	NPC130577
0.5135	Remote Similarity	NPC142415
0.5135	Remote Similarity	NPC102683
0.5132	Remote Similarity	NPC202728
0.5132	Remote Similarity	NPC158059
0.5128	Remote Similarity	NPC174663
0.5128	Remote Similarity	NPC600832
0.5125	Remote Similarity	NPC230151
0.5067	Remote Similarity	NPC282616
0.5067	Remote Similarity	NPC51700
0.5067	Remote Similarity	NPC88716
0.5067	Remote Similarity	NPC68160
0.5065	Remote Similarity	NPC263393
0.5065	Remote Similarity	NPC132824
0.5062	Remote Similarity	NPC233012

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC73004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6523
0.1-0.2	2582
0.2-0.3	41
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
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
		NPD

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