NPASS Compound

Natural Product: NPC249817

Natural Product ID	NPC249817
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	27-Trans-P-Coumaroyloxyursolic Acid
IUPAC Name	(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1,2,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL442938
PubChem CID	14758720
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 2.3300 -0.1583 -2.5593 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5551 -0.5120 -1.3654 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7190 -0.0493 -0.3987 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6201 0.8018 -0.6621 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1754 1.1772 0.5496 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7287 1.8515 1.4948 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4718 2.9546 0.7901 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5117 4.0522 0.4345 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9185 3.6685 0.4523 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2163 2.2321 0.2030 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3826 1.8661 -0.2840 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8172 0.4537 -0.5426 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8959 -0.4918 0.1027 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9884 0.0342 1.1526 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8463 0.6570 2.2619 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1308 -0.9812 1.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3886 -2.4026 1.5963 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4522 -2.7748 0.6284 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5908 -1.8104 0.5006 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5824 -1.7469 1.5532 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3122 -2.2114 -0.8054 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7354 -3.6519 -0.7797 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6261 -4.6156 -0.5235 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8430 -4.2165 0.7100 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5291 -5.0123 0.6042 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5363 -4.6621 1.9277 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1764 -5.8804 -0.3250 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7976 4.5523 -0.3717 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0768 4.8265 0.4357 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2302 5.9084 -0.6671 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1823 5.9387 -1.1038 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9496 4.6755 -0.8789 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1442 6.5756 -1.7255 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7925 5.1415 1.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0647 5.5009 2.3030 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0280 5.7659 1.4804 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6627 -1.3836 -1.0078 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4904 -1.8562 -1.9069 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6087 -2.7284 -1.5950 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4291 -3.1873 -2.6265 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5033 -4.0135 -2.4016 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7936 -4.4115 -1.1170 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0228 -3.9909 -0.0713 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9436 -3.1562 -0.3322 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8679 -5.2400 -0.8775 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8991 1.6920 -1.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0458 0.1450 -1.4003 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2849 2.3421 2.3795 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5379 1.1724 1.8988 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2861 3.3576 1.4917 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9814 2.6591 -0.1469 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2350 3.9144 1.5397 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0986 2.6491 -0.5258 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7996 0.3537 -1.6609 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8899 0.3148 -0.2826 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2834 -0.9076 -0.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2773 1.3107 2.9389 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1789 -0.1563 2.9790 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7284 1.1716 1.9411 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1493 -0.8182 2.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9293 -0.7463 1.5914 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6317 -2.9567 2.5551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5546 -2.9370 1.2569 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9471 -2.6973 -0.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3022 -2.1737 2.5382 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4796 -2.3928 1.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0509 -0.7430 1.6041 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6892 -2.0231 -1.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2567 -1.6128 -0.8029 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0971 -3.8637 -1.8297 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6028 -3.8610 -0.1360 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9068 -4.6078 -1.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7378 -6.0599 0.2710 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0441 -4.9481 1.5802 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1248 -4.4862 -0.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6526 -4.5584 1.8733 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3874 -5.7829 2.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1691 -4.2588 2.8753 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1288 -5.8979 -0.5521 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0467 4.1081 -1.3658 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1697 4.1531 1.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0436 5.8583 0.8978 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9713 4.8382 -0.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4078 6.5559 0.2371 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1938 6.1304 -2.2027 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6736 6.8071 -0.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9608 3.9989 -1.7281 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0249 4.9825 -0.7128 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5023 5.7892 -2.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5275 7.3468 -2.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0245 7.0395 -1.2537 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3548 6.1248 2.3893 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8021 -1.6441 0.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3053 -1.5621 -2.9386 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2115 -2.8824 -3.6302 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1266 -4.3549 -3.2414 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2511 -4.3020 0.9342 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3248 -2.8195 0.5104 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7910 -6.2499 -0.7627 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 5 4 1 6 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 23 27 1 0 9 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 8 34 1 1 34 35 2 0 34 36 1 0 2 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 42 45 1 0 10 5 1 0 19 13 1 0 44 39 1 0 14 5 1 0 24 18 1 0 32 8 1 0 4 46 1 0 4 47 1 0 6 48 1 0 6 49 1 0 7 50 1 0 7 51 1 0 9 52 1 1 11 53 1 0 12 54 1 0 12 55 1 0 13 56 1 6 15 57 1 0 15 58 1 0 15 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 17 63 1 0 18 64 1 6 20 65 1 0 20 66 1 0 20 67 1 0 21 68 1 0 21 69 1 0 22 70 1 0 22 71 1 0 23 72 1 6 25 73 1 0 25 74 1 0 25 75 1 0 26 76 1 0 26 77 1 0 26 78 1 0 27 79 1 0 28 80 1 6 29 81 1 0 29 82 1 0 29 83 1 0 30 84 1 1 31 85 1 0 31 86 1 0 32 87 1 0 32 88 1 0 33 89 1 0 33 90 1 0 33 91 1 0 36 92 1 0 37 93 1 0 38 94 1 0 40 95 1 0 41 96 1 0 43 97 1 0 44 98 1 0 45 99 1 0 M END

Standard InCHIKey	RZHJGXXCTIXCRI-HLWIYMQRSA-N
Standard InCHI	InChI=1S/C39H54O6/c1-24-15-20-38(34(43)44)21-22-39(23-45-32(42)14-9-26-7-10-27(40)11-8-26)28(33(38)25(24)2)12-13-30-36(5)18-17-31(41)35(3,4)29(36)16-19-37(30,39)6/h7-12,14,24-25,29-31,33,40-41H,13,15-23H2,1-6H3,(H,43,44)/b14-9+/t24-,25+,29+,30-,31+,33+,36+,37-,38+,39+/m1/s1
SMILES	O=C(OC[C@@]12CC[C@@]3([C@H](C1=CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)[C@@H](C)[C@@H](CC3)C)C(=O)O)/C=C/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]
NPO40948	Vallaris glabra	Species	n.a.	n.a.	Leaves	n.a.	n.a.	PMID[29072457]
NPO40948	Vallaris glabra	Species	n.a.	n.a.	Stems	n.a.	n.a.	PMID[31820973]

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	3
Activity	1

Activity Type	# Activity
Individual protein	2
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3065	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 1	Rattus norvegicus	IC50	=	73000.0	nM	PMID[23571415]
NPT285	Individual protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	56.48	nM	PMID[30962086]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell line	MDA-MB-231	Homo sapiens	Activity	=	42.03	%	PMID[30962086]
NPT81	Cell line	A549	Homo sapiens	IC50	=	2200.0	nM	PMID[31820973]

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 NPC249817 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	7676
0.1-0.2	36204
0.2-0.3	5234
0.3-0.4	576
0.4-0.5	114
0.5-0.6	26
0.6-0.7	18
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC54627
0.907	High Similarity	NPC475482
0.8571	High Similarity	NPC310729
0.8571	High Similarity	NPC150310
0.809	Intermediate Similarity	NPC262970
0.7263	Intermediate Similarity	NPC479747
0.7263	Intermediate Similarity	NPC479746
0.7097	Intermediate Similarity	NPC475457
0.697	Remote Similarity	NPC206232
0.697	Remote Similarity	NPC14515
0.6771	Remote Similarity	NPC198621
0.6771	Remote Similarity	NPC216940
0.6531	Remote Similarity	NPC479744
0.6465	Remote Similarity	NPC304110
0.6465	Remote Similarity	NPC27518
0.6465	Remote Similarity	NPC611516
0.64	Remote Similarity	NPC178093
0.6275	Remote Similarity	NPC475454
0.6275	Remote Similarity	NPC473579
0.6214	Remote Similarity	NPC479740
0.6214	Remote Similarity	NPC479741
0.6176	Remote Similarity	NPC473773
0.6176	Remote Similarity	NPC475579
0.6078	Remote Similarity	NPC482049
0.6078	Remote Similarity	NPC482050
0.6	Remote Similarity	NPC274330
0.598	Remote Similarity	NPC606782
0.593	Remote Similarity	NPC51700
0.593	Remote Similarity	NPC88716
0.593	Remote Similarity	NPC68160
0.581	Remote Similarity	NPC479745
0.58	Remote Similarity	NPC475627
0.5636	Remote Similarity	NPC53520
0.5619	Remote Similarity	NPC479739
0.5596	Remote Similarity	NPC118033
0.5577	Remote Similarity	NPC172311
0.5566	Remote Similarity	NPC324798
0.5566	Remote Similarity	NPC479742
0.5534	Remote Similarity	NPC488215
0.5429	Remote Similarity	NPC482052
0.5377	Remote Similarity	NPC25491
0.5347	Remote Similarity	NPC485587
0.5294	Remote Similarity	NPC173569
0.5288	Remote Similarity	NPC271494
0.5283	Remote Similarity	NPC605663
0.5238	Remote Similarity	NPC22676
0.5182	Remote Similarity	NPC473680
0.5165	Remote Similarity	NPC61543
0.5165	Remote Similarity	NPC293048
0.5165	Remote Similarity	NPC225585
0.5138	Remote Similarity	NPC475311
0.5093	Remote Similarity	NPC132126

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC249817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3559
0.1-0.2	5483
0.2-0.3	103
0.3-0.4	4
0.4-0.5	0
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
0.598	Remote Similarity	NPD8166	Discontinued

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