NPASS Compound

Natural Product: NPC288464

Natural Product ID	NPC288464
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RWIALJIVPUCERT-DRCQUEPLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	15226717
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 91 0 0 0 0 0 0 0 0999 V2000 7.6661 -0.6568 1.8229 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5667 0.7032 1.2068 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6811 1.5475 2.1319 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8757 0.6792 -0.1088 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5209 1.1712 -1.1542 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5140 0.1123 -0.1733 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9409 0.1808 -1.5635 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5632 -0.3624 -1.7139 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5149 0.2963 -0.8902 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3274 1.7563 -1.1419 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8375 1.9842 -1.2699 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3048 0.8593 -0.4475 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4593 1.0257 1.0246 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0894 0.4975 -0.7347 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9147 1.3149 -1.3974 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3211 0.8177 -1.6230 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7068 0.1437 -0.3061 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1762 0.0761 -0.0781 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7142 1.5082 -0.2188 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9470 -0.7828 -1.0062 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3488 -0.3215 1.3927 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7005 -1.6477 1.6364 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2355 -1.5947 1.3210 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9684 -1.1289 -0.0908 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2723 -2.2154 -1.0640 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5008 -0.8142 -0.2440 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5762 -1.6856 0.0451 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8902 -1.4551 -0.0846 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1568 -0.3077 -0.9891 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7167 -0.6698 -2.3828 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6753 -0.2479 1.8116 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1260 0.6373 2.7826 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2744 1.4064 3.3002 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5629 0.6836 3.2043 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7545 2.5438 -0.0721 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6019 -1.8297 -1.5805 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2862 -2.6241 -2.5276 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9859 -2.4453 -0.4075 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8312 -0.8324 2.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7372 -1.4711 1.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5929 -0.6937 2.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5773 1.1497 1.1370 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2925 1.9313 2.9770 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8975 0.8451 2.5119 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2166 2.3504 1.5360 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0868 1.1886 -2.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5276 1.5854 -1.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6510 -0.9844 0.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8986 0.5733 0.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0748 1.1825 -2.0294 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6149 -0.4896 -2.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2487 -0.1744 -2.7902 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8326 0.1942 0.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8683 2.1428 -2.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5062 2.9390 -0.8167 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4801 1.8524 -2.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6275 2.1103 1.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2503 0.4529 1.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4879 0.7621 1.5804 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5571 2.2560 -1.7295 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9411 1.7344 -1.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3886 0.1445 -2.4769 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3172 0.8599 0.4829 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9807 2.2447 0.1568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6955 1.5774 0.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9473 1.6329 -1.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3293 -1.7265 -0.5143 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4226 -1.0185 -1.9653 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8998 -0.2731 -1.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7371 0.4381 1.9637 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7936 -1.8654 2.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2058 -2.4854 1.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8314 -2.6324 1.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7367 -0.9528 2.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4463 -2.9819 -0.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2008 -2.7707 -0.8713 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1781 -1.8505 -2.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9028 -2.6633 0.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2618 -2.3776 -0.6295 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4224 -1.4649 0.8676 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2695 -0.1625 -3.1739 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6947 -1.7765 -2.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3676 -0.3848 -2.5180 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0556 -0.2781 3.0257 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1181 1.4692 2.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5693 0.9798 4.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9376 1.9302 0.6805 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6577 -3.3727 -0.1833 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 6 21 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 10 35 1 0 8 36 1 0 36 37 2 0 36 38 1 0 29 9 1 0 29 12 1 0 26 14 1 0 24 17 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 3 43 1 0 3 44 1 0 3 45 1 0 5 46 1 0 5 47 1 0 6 48 1 0 6 49 1 0 7 50 1 0 7 51 1 0 8 52 1 6 9 53 1 1 10 54 1 6 11 55 1 0 11 56 1 0 13 57 1 0 13 58 1 0 13 59 1 0 15 60 1 0 16 61 1 0 16 62 1 0 17 63 1 1 19 64 1 0 19 65 1 0 19 66 1 0 20 67 1 0 20 68 1 0 20 69 1 0 21 70 1 1 22 71 1 0 22 72 1 0 23 73 1 0 23 74 1 0 25 75 1 0 25 76 1 0 25 77 1 0 27 78 1 0 28 79 1 0 28 80 1 0 30 81 1 0 30 82 1 0 30 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 35 87 1 0 38 88 1 0 M END

Standard InCHIKey	RWIALJIVPUCERT-DRCQUEPLSA-N
Standard InCHI	InChI=1S/C33H50O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h12,14,19,22,25-28,35H,3,10-11,13,15-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1
SMILES	CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)OC(=O)C)O)C(=O)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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO6117	Poria	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6117	Poria	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	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	4

Activity Type	# Activity
Cell line	4

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	=	18600.0	nM	PMID[27808511]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	7300.0	nM	PMID[27808511]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	=	2700.0	nM	PMID[27808511]
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	=	13800.0	nM	PMID[27808511]

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 NPC288464 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	15626
0.1-0.2	28280
0.2-0.3	5617
0.3-0.4	249
0.4-0.5	45
0.5-0.6	18
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
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	NPC477813
1.0	High Similarity	NPC607198
0.8235	Intermediate Similarity	NPC484969
0.75	Intermediate Similarity	NPC45324
0.75	Intermediate Similarity	NPC162001
0.7083	Intermediate Similarity	NPC263347
0.7042	Intermediate Similarity	NPC152897
0.7042	Intermediate Similarity	NPC484967
0.6944	Remote Similarity	NPC184848
0.6575	Remote Similarity	NPC123854
0.6438	Remote Similarity	NPC186810
0.6164	Remote Similarity	NPC48866
0.6133	Remote Similarity	NPC484973
0.6133	Remote Similarity	NPC484968
0.6053	Remote Similarity	NPC155676
0.6027	Remote Similarity	NPC222845
0.6027	Remote Similarity	NPC296577
0.6	Remote Similarity	NPC484975
0.6	Remote Similarity	NPC321301
0.6	Remote Similarity	NPC608955
0.5844	Remote Similarity	NPC69548
0.5789	Remote Similarity	NPC48647
0.5658	Remote Similarity	NPC66429
0.5658	Remote Similarity	NPC77168
0.5641	Remote Similarity	NPC276127
0.5641	Remote Similarity	NPC7165
0.5641	Remote Similarity	NPC478307
0.5584	Remote Similarity	NPC484966
0.5584	Remote Similarity	NPC477812
0.5443	Remote Similarity	NPC478313
0.5443	Remote Similarity	NPC489790
0.5432	Remote Similarity	NPC469432
0.5325	Remote Similarity	NPC474889
0.5256	Remote Similarity	NPC45269
0.5256	Remote Similarity	NPC203035
0.5176	Remote Similarity	NPC484972
0.5119	Remote Similarity	NPC94393
0.5065	Remote Similarity	NPC23434

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC288464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5418
0.1-0.2	3616
0.2-0.3	114
0.3-0.4	2
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