NPASS Compound

Natural Product: NPC473482

Natural Product ID	NPC473482
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Globostellatic Acd C Methyl Ester
IUPAC Name	methyl (3E,3aS,5aR,6R,7R,9aR,9bR)-7-acetyloxy-3-[(3E,5E,7E)-10-hydroxy-9-methoxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalene-6-carboxylate
Synonyms	Globostellatic Acd C Methyl Ester
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL443134
PubChem CID	44583713
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 91 93 0 0 0 0 0 0 0 0999 V2000 9.2520 -2.7263 -2.5550 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2618 -1.8770 -1.4467 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3151 -0.8585 -1.5953 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9612 0.4860 -1.5305 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9021 0.5551 -2.5746 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8805 1.5437 -1.7399 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6102 0.7397 -0.1943 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3248 -0.9529 -0.4478 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0783 -0.6321 -0.6006 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1135 -0.7146 0.4844 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8406 -0.3791 0.2994 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9027 -0.4697 1.3888 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6185 -0.1442 1.2626 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7297 -0.2519 2.3794 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5570 0.0356 2.3136 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5301 -0.0655 3.4398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5097 -0.8599 4.3816 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 1.0027 3.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5890 1.1175 1.6985 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3016 0.5369 1.1244 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5840 1.6666 0.4068 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5643 -0.5646 0.1649 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7019 -0.3688 -0.8012 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7558 0.5636 -0.3538 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8339 0.4781 1.1738 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0775 -0.9185 1.6380 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9780 1.4063 1.5826 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2910 0.8668 1.1384 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2078 0.0910 -0.1564 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0611 0.5784 -1.0232 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4840 2.0315 -1.3961 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1238 -0.1594 -2.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1560 -0.7337 -2.7909 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3303 -0.2644 -3.0172 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4197 -0.9635 -4.2253 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4044 0.3904 -0.8512 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3428 -0.5603 -1.2005 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1672 -1.7533 -0.9090 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5664 -0.0968 -1.9365 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2873 -0.6855 3.7301 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4900 -1.1645 1.8360 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0072 -3.5114 -2.4012 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2619 -3.2320 -2.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4696 -2.2045 -3.4918 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8128 -1.0015 -2.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6893 1.0528 -2.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2498 1.5197 -0.8502 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3693 2.5386 -1.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2975 1.2572 -2.6193 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7887 1.1033 0.4846 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3718 1.5468 -0.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0512 -0.1778 0.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7428 -1.3008 0.4704 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7813 -0.2928 -1.5954 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5792 -0.0451 -0.6991 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2379 -0.8237 2.3410 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3122 0.1801 0.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2011 1.9731 3.5942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4651 0.6880 3.6717 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6538 2.2032 1.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2504 2.1015 0.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3058 2.5525 0.3429 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3616 1.4604 -0.6472 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6752 -1.5451 0.7195 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6646 -0.7239 -0.4598 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3096 -0.0175 -1.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1286 -1.3746 -0.9682 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3194 1.6115 -0.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3739 -1.2975 2.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0885 -0.9808 2.1443 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0530 -1.6491 0.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0151 1.5195 2.6893 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7978 2.3906 1.1132 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9959 1.7344 1.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7140 0.2284 1.9403 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1983 -0.9993 0.0086 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2814 2.3984 -0.7362 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5754 2.6508 -1.2429 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7283 2.0978 -2.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4619 -1.3575 -4.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2531 -0.3195 -5.1242 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7309 -1.8047 -4.3007 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8175 0.8967 -1.5318 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4057 -0.8023 -1.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2711 -0.0101 -2.9959 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2782 -0.1749 3.8592 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4390 -1.7749 3.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5969 -0.3890 4.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0084 -2.1363 2.1053 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5652 -1.3120 2.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1930 -0.3714 2.5750 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 4 6 1 0 4 7 1 0 3 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 30 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 29 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 14 40 1 0 10 41 1 0 20 15 1 0 30 24 1 0 25 19 1 0 1 42 1 0 1 43 1 0 1 44 1 0 3 45 1 0 5 46 1 0 6 47 1 0 6 48 1 0 6 49 1 0 7 50 1 0 7 51 1 0 7 52 1 0 8 53 1 0 9 54 1 0 11 55 1 0 12 56 1 0 13 57 1 0 18 58 1 0 18 59 1 0 19 60 1 1 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 24 68 1 1 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 29 76 1 1 31 77 1 0 31 78 1 0 31 79 1 0 35 80 1 0 35 81 1 0 35 82 1 0 39 83 1 0 39 84 1 0 39 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 41 89 1 0 41 90 1 0 41 91 1 0 M END

Standard InCHIKey	JKYUKDUGIIRUKJ-LPFBVOCUSA-N
Standard InCHI	InChI=1S/C34H50O7/c1-21(14-15-27(39-9)31(4,5)38)12-11-13-22(2)29-24(36)20-26-32(6)19-17-28(41-23(3)35)34(8,30(37)40-10)25(32)16-18-33(26,29)7/h11-15,25-28,38H,16-20H2,1-10H3/b13-11+,15-14+,21-12+,29-22-/t25-,26-,27?,28-,32+,33+,34-/m1/s1
SMILES	COC(C(O)(C)C)/C=C/C(=C/C=C/C(=C1/C(=O)C[C@H]2[C@]1(C)CC[C@@H]1[C@]2(C)CC[C@H]([C@]1(C)C(=O)OC)OC(=O)C)/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
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	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
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	3.3	ug.mL-1	PMID[10924170]

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 NPC473482 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	14969
0.1-0.2	29457
0.2-0.3	5264
0.3-0.4	101
0.4-0.5	30
0.5-0.6	23
0.6-0.7	4
0.7-0.8	0
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8254	Intermediate Similarity	NPC473435
0.8254	Intermediate Similarity	NPC473280
0.8254	Intermediate Similarity	NPC471078
0.8182	Intermediate Similarity	NPC473284
0.8	Intermediate Similarity	NPC106425
0.8	Intermediate Similarity	NPC122324
0.7794	Intermediate Similarity	NPC473283
0.7794	Intermediate Similarity	NPC475526
0.7656	Intermediate Similarity	NPC151725
0.6923	Remote Similarity	NPC2049
0.6667	Remote Similarity	NPC318363
0.6154	Remote Similarity	NPC161638
0.6154	Remote Similarity	NPC80335
0.5844	Remote Similarity	NPC329048
0.5802	Remote Similarity	NPC475418
0.5769	Remote Similarity	NPC330011
0.5753	Remote Similarity	NPC471153
0.5733	Remote Similarity	NPC266955
0.5694	Remote Similarity	NPC474842
0.5694	Remote Similarity	NPC475965
0.5694	Remote Similarity	NPC604299
0.5658	Remote Similarity	NPC155332
0.5658	Remote Similarity	NPC114540
0.5584	Remote Similarity	NPC115899
0.5541	Remote Similarity	NPC57079
0.5541	Remote Similarity	NPC108368
0.5479	Remote Similarity	NPC474790
0.5479	Remote Similarity	NPC474976
0.5395	Remote Similarity	NPC605871
0.5325	Remote Similarity	NPC110937
0.5195	Remote Similarity	NPC6206
0.5181	Remote Similarity	NPC329345
0.5132	Remote Similarity	NPC474785
0.5128	Remote Similarity	NPC10064
0.5128	Remote Similarity	NPC170221
0.506	Remote Similarity	NPC475065

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5870
0.1-0.2	3180
0.2-0.3	100
0.3-0.4	0
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