NPASS Compound

Natural Product: NPC233012

Natural Product ID	NPC233012
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3 Beta-Acetyl Tormentic Acid
IUPAC Name	(1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10-acetyloxy-1,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	3 Beta-Acetyl Tormentic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL239296
PubChem CID	44436804
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 88 92 0 0 0 0 0 0 0 0999 V2000 8.3876 0.8423 1.1935 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0514 0.6339 1.7899 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9354 0.4442 2.9988 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9491 0.6516 1.0026 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6122 0.4665 1.4301 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7665 1.6766 1.2738 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7427 2.4263 2.4848 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3407 1.4509 0.9238 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1420 0.4067 -0.1901 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7004 -0.8221 0.4148 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1141 -0.8053 0.8330 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2610 -1.9244 1.8794 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0484 -1.3035 -0.2838 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3869 -1.9467 -0.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8846 -2.1478 -0.3903 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1041 -0.9755 -0.9536 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6719 0.2749 -0.3933 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1145 1.4463 -1.1334 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3457 1.3491 -0.9217 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0377 0.2647 -0.6446 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3603 -1.0549 -0.5065 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4829 -1.6634 0.8618 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1679 -1.9859 -1.4251 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6369 -1.9290 -1.0885 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2885 -0.6150 -1.2144 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5004 0.4718 -0.5403 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0419 0.9392 0.7672 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2021 2.0795 1.2838 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3548 0.0073 1.7061 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4174 1.6002 0.4923 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1411 1.8319 1.7755 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2675 0.7003 -0.3765 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6536 -0.6682 -0.5633 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4557 -0.2864 -2.6767 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8974 0.7439 -3.1284 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1910 -1.0618 -3.5419 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2259 -1.1373 -2.4496 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8640 0.9050 -1.4051 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8966 1.7579 1.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0453 -0.0679 1.3178 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3092 0.9925 0.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7145 0.3118 2.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1728 2.4275 0.5583 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0904 3.1478 2.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8255 1.0139 1.8281 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8725 2.3968 0.7030 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0872 -1.0247 1.3453 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2578 -2.3640 1.8809 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4551 -2.6603 1.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1484 -1.4206 2.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1320 -0.6141 -1.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6941 -2.2750 -0.6828 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0135 -1.5166 0.2286 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7347 -1.8266 -1.5409 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8382 -2.8718 -0.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 -3.0899 -0.9406 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7821 -2.2466 0.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2673 0.2963 0.6714 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5155 2.4227 -0.8178 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2495 1.4031 -2.2298 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8851 2.2951 -1.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5332 -1.8689 1.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1270 -2.7384 0.8720 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8932 -1.1643 1.6387 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8969 -3.0392 -1.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1030 -1.6920 -2.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1136 -2.5755 -1.8987 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9430 -2.4209 -0.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8016 1.3766 -1.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3887 2.9905 0.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1387 1.8562 1.3395 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5905 2.3004 2.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7278 0.0665 2.4696 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2755 2.5422 -0.0499 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6142 2.4876 2.4816 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0877 2.3774 1.5125 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4674 0.8698 2.2407 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4037 1.1279 -1.4072 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2685 0.5169 0.0904 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3128 -1.1841 -1.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6915 -1.3042 0.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4192 -0.7417 -4.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1521 -2.1294 -2.7991 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2853 -0.3852 -3.0389 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2759 -1.1586 -2.8010 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2265 1.6749 -1.8845 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8120 1.4312 -1.1624 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 0.1615 -2.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 11 13 1 0 10 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 2 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 1 27 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 25 34 1 6 34 35 2 0 34 36 1 0 16 37 1 6 9 38 1 6 11 5 1 0 21 16 1 0 33 25 1 0 17 9 1 0 26 20 1 0 1 39 1 0 1 40 1 0 1 41 1 0 5 42 1 1 6 43 1 6 7 44 1 0 8 45 1 0 8 46 1 0 10 47 1 1 12 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 17 58 1 1 18 59 1 0 18 60 1 0 19 61 1 0 22 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 26 69 1 6 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 30 74 1 6 31 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 33 80 1 0 33 81 1 0 36 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 38 86 1 0 38 87 1 0 38 88 1 0 M END

Standard InCHIKey	HWGMGZJITMCAFQ-BGJCYSRJSA-N
Standard InCHI	InChI=1S/C32H50O6/c1-18-11-14-32(26(35)36)16-15-29(6)20(24(32)31(18,8)37)9-10-23-28(5)17-21(34)25(38-19(2)33)27(3,4)22(28)12-13-30(23,29)7/h9,18,21-25,34,37H,10-17H2,1-8H3,(H,35,36)/t18-,21-,22+,23-,24-,25+,28+,29-,30-,31-,32+/m1/s1
SMILES	CC(=O)O[C@H]1[C@H](O)C[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@H](C)CC1)C(=O)O)C)C

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
NPO20072	Verbascum dudleyanum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5696	Premna fulva	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6660	Cecropia lyratiloba	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1029	Vernonia jalcana	Species	Asteraceae	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

Activity Type	# Activity
IC50	10

Activity Type	# Activity
Cell line	7
Non-molecular	3

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
NPT111	Cell line	K562	Homo sapiens	IC50	=	56610.0	nM	PMID[17889544]
NPT1215	Cell line	8505C	Homo sapiens	IC50	>	30000.0	nM	PMID[22995818]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	28100.0	nM	PMID[22995818]
NPT81	Cell line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[22995818]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	>	30000.0	nM	PMID[22995818]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	26200.0	nM	PMID[22995818]
NPT886	Cell line	NIH3T3	Mus musculus	IC50	>	30000.0	nM	PMID[22995818]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	72870.0	nM	PMID[17889544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[22995818]

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 NPC233012 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	17405
0.1-0.2	26299
0.2-0.3	5062
0.3-0.4	802
0.4-0.5	214
0.5-0.6	36
0.6-0.7	26
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
0.7671	Intermediate Similarity	NPC230151
0.75	Intermediate Similarity	NPC25491
0.7333	Intermediate Similarity	NPC54909
0.7326	Intermediate Similarity	NPC482051
0.7105	Intermediate Similarity	NPC327179
0.6923	Remote Similarity	NPC481234
0.6923	Remote Similarity	NPC479431
0.6892	Remote Similarity	NPC62516
0.6849	Remote Similarity	NPC259733
0.6849	Remote Similarity	NPC158371
0.6849	Remote Similarity	NPC207922
0.6849	Remote Similarity	NPC202728
0.6849	Remote Similarity	NPC158059
0.6757	Remote Similarity	NPC247139
0.6667	Remote Similarity	NPC148964
0.6622	Remote Similarity	NPC136697
0.6579	Remote Similarity	NPC187933
0.6579	Remote Similarity	NPC157113
0.6533	Remote Similarity	NPC191412
0.6533	Remote Similarity	NPC114159
0.6533	Remote Similarity	NPC132824
0.6533	Remote Similarity	NPC6818
0.641	Remote Similarity	NPC603658
0.6316	Remote Similarity	NPC35239
0.625	Remote Similarity	NPC96693
0.6234	Remote Similarity	NPC118964
0.6184	Remote Similarity	NPC256247
0.6154	Remote Similarity	NPC147232
0.6154	Remote Similarity	NPC284865
0.6053	Remote Similarity	NPC235053
0.6044	Remote Similarity	NPC482052
0.5978	Remote Similarity	NPC304110
0.5978	Remote Similarity	NPC27518
0.5978	Remote Similarity	NPC611516
0.5897	Remote Similarity	NPC118519
0.5889	Remote Similarity	NPC171007
0.5889	Remote Similarity	NPC190849
0.587	Remote Similarity	NPC605663
0.5833	Remote Similarity	NPC600756
0.5823	Remote Similarity	NPC137072
0.56	Remote Similarity	NPC481235
0.5579	Remote Similarity	NPC482049
0.5579	Remote Similarity	NPC482050
0.557	Remote Similarity	NPC120840
0.5556	Remote Similarity	NPC118033
0.55	Remote Similarity	NPC485589
0.5455	Remote Similarity	NPC601567
0.5455	Remote Similarity	NPC606631
0.5417	Remote Similarity	NPC178093
0.5306	Remote Similarity	NPC479745
0.5238	Remote Similarity	NPC485586
0.5238	Remote Similarity	NPC485588
0.5204	Remote Similarity	NPC324798
0.5204	Remote Similarity	NPC479742
0.5181	Remote Similarity	NPC296164
0.5158	Remote Similarity	NPC127853
0.5122	Remote Similarity	NPC9613
0.5062	Remote Similarity	NPC173744
0.5062	Remote Similarity	NPC88116
0.5062	Remote Similarity	NPC204961
0.5062	Remote Similarity	NPC73004
0.5062	Remote Similarity	NPC71074
0.5062	Remote Similarity	NPC37221
0.5062	Remote Similarity	NPC110308
0.5062	Remote Similarity	NPC605937
0.506	Remote Similarity	NPC25299
0.506	Remote Similarity	NPC481322

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC233012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5619
0.1-0.2	3443
0.2-0.3	76
0.3-0.4	12
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