NPASS Compound

Structure

NPC232812 OpenBabel07101718322D 21 21 0 0 1 0 0 0 0 0999 V2000 -4.2711 -0.7996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3122 -0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6450 -2.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9496 0.6032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9127 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6588 -1.8879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9250 0.2904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2957 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6787 -1.1075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3080 -0.3303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0570 3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9230 1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 5 20 1 0 0 0 0 6 9 1 0 0 0 0 7 15 1 0 0 0 0 9 10 1 0 0 0 0 10 14 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 4 1 6 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 8 1 6 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.22
Volume:	329.789
LogP:	4.792
LogD:	4.568
LogS:	-5.035
# Rotatable Bonds:	9
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	4.148
Fsp3:	0.722
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.48
MDCK Permeability:	2.462831253069453e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.832
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.368
Plasma Protein Binding (PPB):	95.34303283691406%
Volume Distribution (VD):	1.49
Pgp-substrate:	3.982578992843628%

ADMET: Metabolism

CYP1A2-inhibitor:	0.941
CYP1A2-substrate:	0.678
CYP2C19-inhibitor:	0.888
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.852
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.945
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	7.91
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.808
Drug-inuced Liver Injury (DILI):	0.537
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.905
Carcinogencity:	0.246
Eye Corrosion:	0.016
Eye Irritation:	0.185
Respiratory Toxicity:	0.909

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC232812

Natural Product ID:	NPC232812
*Common Name:**	Methyl (2Z)-2-[(5R)-3,5-Diethyl-5-[(2S)-2-Methylhexyl]Furan-2-Ylidene]Acetate
IUPAC Name:	methyl (2Z)-2-[(5R)-3,5-diethyl-5-[(2S)-2-methylhexyl]furan-2-ylidene]acetate
Synonyms:
Standard InCHIKey:	HTKSPKWIEZBJMH-ZDFYXSBBSA-N
Standard InCHI:	InChI=1S/C18H30O3/c1-6-9-10-14(4)12-18(8-3)13-15(7-2)16(21-18)11-17(19)20-5/h11,13-14H,6-10,12H2,1-5H3/b16-11-/t14-,18+/m0/s1
SMILES:	CCCC[C@@H](C[C@@]1(CC)O/C(=CC(=O)OC)/C(=C1)CC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443777
PubChem CID:	10685234
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[11720540]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738400]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	rock wall at 96 m depth, near Blue Hole, Orote Peninsula, Guam	n.a.	PMID[19618913]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20235550]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[23186727]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760075]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722495]

☑ 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	NP ID	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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LD50	=	7.0	mg/L	PMID[469341]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC232812 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1365
0.2-0.3	6474
0.3-0.4	18378
0.4-0.5	10013
0.5-0.6	4787
0.6-0.7	1288
0.7-0.8	196
0.8-0.85	3
0.85-0.9	2
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC37929
0.9846	High Similarity	NPC64234
0.9231	High Similarity	NPC191233
0.9077	High Similarity	NPC220766
0.8824	High Similarity	NPC470693
0.8806	High Similarity	NPC472266
0.8551	High Similarity	NPC265574
0.8429	Intermediate Similarity	NPC316029
0.8406	Intermediate Similarity	NPC276290
0.8333	Intermediate Similarity	NPC470686
0.8243	Intermediate Similarity	NPC54996
0.8169	Intermediate Similarity	NPC315285
0.8143	Intermediate Similarity	NPC313444
0.8	Intermediate Similarity	NPC315394
0.8	Intermediate Similarity	NPC471225
0.7971	Intermediate Similarity	NPC470688
0.7941	Intermediate Similarity	NPC217940
0.7917	Intermediate Similarity	NPC315597
0.7838	Intermediate Similarity	NPC474758
0.7808	Intermediate Similarity	NPC181587
0.7805	Intermediate Similarity	NPC260343
0.7778	Intermediate Similarity	NPC269841
0.7763	Intermediate Similarity	NPC316324
0.7763	Intermediate Similarity	NPC473825
0.7763	Intermediate Similarity	NPC180290
0.7733	Intermediate Similarity	NPC329852
0.7711	Intermediate Similarity	NPC242877
0.7711	Intermediate Similarity	NPC64913
0.7681	Intermediate Similarity	NPC155849
0.7671	Intermediate Similarity	NPC469660
0.7662	Intermediate Similarity	NPC474005
0.7662	Intermediate Similarity	NPC128276
0.7662	Intermediate Similarity	NPC471220
0.7632	Intermediate Similarity	NPC301525
0.7606	Intermediate Similarity	NPC116013
0.7606	Intermediate Similarity	NPC315115
0.76	Intermediate Similarity	NPC259599
0.76	Intermediate Similarity	NPC294434
0.76	Intermediate Similarity	NPC117746
0.76	Intermediate Similarity	NPC15499
0.7595	Intermediate Similarity	NPC42470
0.759	Intermediate Similarity	NPC472302
0.759	Intermediate Similarity	NPC471956
0.7576	Intermediate Similarity	NPC96663
0.7568	Intermediate Similarity	NPC477084
0.7534	Intermediate Similarity	NPC101622
0.7534	Intermediate Similarity	NPC475004
0.7532	Intermediate Similarity	NPC57744
0.7532	Intermediate Similarity	NPC68156
0.7529	Intermediate Similarity	NPC166110
0.7529	Intermediate Similarity	NPC32494
0.7529	Intermediate Similarity	NPC175842
0.75	Intermediate Similarity	NPC221231
0.75	Intermediate Similarity	NPC471326
0.75	Intermediate Similarity	NPC21998
0.75	Intermediate Similarity	NPC469414
0.75	Intermediate Similarity	NPC83838
0.75	Intermediate Similarity	NPC329826
0.75	Intermediate Similarity	NPC143810
0.7468	Intermediate Similarity	NPC268827
0.7467	Intermediate Similarity	NPC16349
0.7467	Intermediate Similarity	NPC222244
0.7465	Intermediate Similarity	NPC182794
0.7442	Intermediate Similarity	NPC59646
0.7442	Intermediate Similarity	NPC248193
0.7439	Intermediate Similarity	NPC471185
0.7436	Intermediate Similarity	NPC184737
0.7436	Intermediate Similarity	NPC299235
0.7432	Intermediate Similarity	NPC4299
0.7432	Intermediate Similarity	NPC67183
0.7429	Intermediate Similarity	NPC179087
0.7429	Intermediate Similarity	NPC210303
0.7429	Intermediate Similarity	NPC44343
0.7412	Intermediate Similarity	NPC3436
0.7407	Intermediate Similarity	NPC475714
0.7407	Intermediate Similarity	NPC170377
0.7403	Intermediate Similarity	NPC476317
0.7403	Intermediate Similarity	NPC469880
0.7403	Intermediate Similarity	NPC123360
0.7397	Intermediate Similarity	NPC474823
0.7397	Intermediate Similarity	NPC218477
0.7391	Intermediate Similarity	NPC127824
0.7381	Intermediate Similarity	NPC473658
0.7375	Intermediate Similarity	NPC325031
0.7375	Intermediate Similarity	NPC471325
0.7368	Intermediate Similarity	NPC476355
0.7356	Intermediate Similarity	NPC470521
0.7342	Intermediate Similarity	NPC63649
0.7342	Intermediate Similarity	NPC264227
0.7342	Intermediate Similarity	NPC471537
0.7342	Intermediate Similarity	NPC472965
0.7342	Intermediate Similarity	NPC178277
0.7333	Intermediate Similarity	NPC257618
0.7333	Intermediate Similarity	NPC163003
0.7333	Intermediate Similarity	NPC5734
0.7326	Intermediate Similarity	NPC470520
0.7324	Intermediate Similarity	NPC34883
0.7317	Intermediate Similarity	NPC14575
0.7317	Intermediate Similarity	NPC475706
0.7317	Intermediate Similarity	NPC196487
0.7308	Intermediate Similarity	NPC187568
0.7308	Intermediate Similarity	NPC41780
0.7308	Intermediate Similarity	NPC189206
0.7308	Intermediate Similarity	NPC476439
0.7297	Intermediate Similarity	NPC329656
0.7294	Intermediate Similarity	NPC95364
0.7294	Intermediate Similarity	NPC142159
0.7294	Intermediate Similarity	NPC225283
0.7294	Intermediate Similarity	NPC307092
0.7284	Intermediate Similarity	NPC35556
0.7284	Intermediate Similarity	NPC173609
0.7284	Intermediate Similarity	NPC474028
0.7284	Intermediate Similarity	NPC474439
0.7284	Intermediate Similarity	NPC471218
0.7273	Intermediate Similarity	NPC244166
0.7262	Intermediate Similarity	NPC191283
0.7262	Intermediate Similarity	NPC125925
0.725	Intermediate Similarity	NPC474510
0.7246	Intermediate Similarity	NPC133600
0.7241	Intermediate Similarity	NPC1108
0.7237	Intermediate Similarity	NPC476489
0.7237	Intermediate Similarity	NPC476490
0.7237	Intermediate Similarity	NPC287878
0.7229	Intermediate Similarity	NPC67081
0.7229	Intermediate Similarity	NPC471223
0.7229	Intermediate Similarity	NPC197903
0.7229	Intermediate Similarity	NPC472442
0.7229	Intermediate Similarity	NPC99395
0.7222	Intermediate Similarity	NPC471556
0.7215	Intermediate Similarity	NPC315765
0.72	Intermediate Similarity	NPC475310
0.7195	Intermediate Similarity	NPC475947
0.7195	Intermediate Similarity	NPC30502
0.7195	Intermediate Similarity	NPC193198
0.7195	Intermediate Similarity	NPC474809
0.7195	Intermediate Similarity	NPC288281
0.7195	Intermediate Similarity	NPC311070
0.7195	Intermediate Similarity	NPC474193
0.7195	Intermediate Similarity	NPC12283
0.7191	Intermediate Similarity	NPC301596
0.7191	Intermediate Similarity	NPC299396
0.7191	Intermediate Similarity	NPC172998
0.7179	Intermediate Similarity	NPC473223
0.7179	Intermediate Similarity	NPC4509
0.7179	Intermediate Similarity	NPC27205
0.7179	Intermediate Similarity	NPC235906
0.7176	Intermediate Similarity	NPC26078
0.7164	Intermediate Similarity	NPC478117
0.7162	Intermediate Similarity	NPC470256
0.7162	Intermediate Similarity	NPC310210
0.716	Intermediate Similarity	NPC112868
0.716	Intermediate Similarity	NPC78677
0.716	Intermediate Similarity	NPC141810
0.716	Intermediate Similarity	NPC184208
0.716	Intermediate Similarity	NPC315731
0.716	Intermediate Similarity	NPC475944
0.716	Intermediate Similarity	NPC59994
0.716	Intermediate Similarity	NPC8538
0.716	Intermediate Similarity	NPC474894
0.7143	Intermediate Similarity	NPC19241
0.7143	Intermediate Similarity	NPC477204
0.7143	Intermediate Similarity	NPC234038
0.7143	Intermediate Similarity	NPC140287
0.7143	Intermediate Similarity	NPC291712
0.7143	Intermediate Similarity	NPC471219
0.7143	Intermediate Similarity	NPC122502
0.7143	Intermediate Similarity	NPC429928
0.7126	Intermediate Similarity	NPC2882
0.7126	Intermediate Similarity	NPC32944
0.7126	Intermediate Similarity	NPC193396
0.7125	Intermediate Similarity	NPC271632
0.7125	Intermediate Similarity	NPC617
0.7125	Intermediate Similarity	NPC469690
0.7123	Intermediate Similarity	NPC248125
0.7108	Intermediate Similarity	NPC82297
0.7108	Intermediate Similarity	NPC149869
0.7108	Intermediate Similarity	NPC471301
0.7108	Intermediate Similarity	NPC96055
0.7108	Intermediate Similarity	NPC475100
0.7108	Intermediate Similarity	NPC471302
0.7108	Intermediate Similarity	NPC318515
0.7105	Intermediate Similarity	NPC472254
0.7105	Intermediate Similarity	NPC84038
0.7105	Intermediate Similarity	NPC129665
0.7105	Intermediate Similarity	NPC186531
0.7093	Intermediate Similarity	NPC51358
0.7089	Intermediate Similarity	NPC84360
0.7089	Intermediate Similarity	NPC65603
0.7089	Intermediate Similarity	NPC470240
0.7089	Intermediate Similarity	NPC53581
0.7089	Intermediate Similarity	NPC262747
0.7089	Intermediate Similarity	NPC103987
0.7089	Intermediate Similarity	NPC476794
0.7083	Intermediate Similarity	NPC226066
0.7083	Intermediate Similarity	NPC477457
0.7083	Intermediate Similarity	NPC477456
0.7079	Intermediate Similarity	NPC234339
0.7079	Intermediate Similarity	NPC273197
0.7073	Intermediate Similarity	NPC474291
0.7073	Intermediate Similarity	NPC16321

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC232812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1734
0.2-0.3	4117
0.3-0.4	2319
0.4-0.5	628
0.5-0.6	156
0.6-0.7	15
0.7-0.8	3
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
0.8235	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5209	Approved
0.7051	Intermediate Similarity	NPD8039	Approved
0.6629	Remote Similarity	NPD7838	Discovery
0.6588	Remote Similarity	NPD7154	Phase 3
0.6575	Remote Similarity	NPD4194	Approved
0.6575	Remote Similarity	NPD4193	Approved
0.6575	Remote Similarity	NPD4191	Approved
0.6575	Remote Similarity	NPD4192	Approved
0.6512	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4756	Discovery
0.6437	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1694	Approved
0.6437	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6051	Approved
0.6324	Remote Similarity	NPD6927	Phase 3
0.6316	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD46	Approved
0.6264	Remote Similarity	NPD6698	Approved
0.625	Remote Similarity	NPD6648	Approved
0.6196	Remote Similarity	NPD5693	Phase 1
0.6154	Remote Similarity	NPD1695	Approved
0.6087	Remote Similarity	NPD5785	Approved
0.6087	Remote Similarity	NPD5207	Approved
0.6087	Remote Similarity	NPD5692	Phase 3
0.6047	Remote Similarity	NPD4821	Approved
0.6047	Remote Similarity	NPD4820	Approved
0.6047	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4819	Approved
0.6047	Remote Similarity	NPD4822	Approved
0.6029	Remote Similarity	NPD4220	Pre-registration
0.6026	Remote Similarity	NPD7331	Phase 2
0.6023	Remote Similarity	NPD5362	Discontinued
0.6022	Remote Similarity	NPD6050	Approved
0.6022	Remote Similarity	NPD5694	Approved
0.6019	Remote Similarity	NPD2067	Discontinued
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD5909	Discontinued
0.5979	Remote Similarity	NPD7638	Approved
0.5979	Remote Similarity	NPD4225	Approved
0.5934	Remote Similarity	NPD4250	Approved
0.5934	Remote Similarity	NPD4251	Approved
0.5918	Remote Similarity	NPD7639	Approved
0.5918	Remote Similarity	NPD7640	Approved
0.5889	Remote Similarity	NPD5363	Approved
0.587	Remote Similarity	NPD5208	Approved
0.587	Remote Similarity	NPD5737	Approved
0.587	Remote Similarity	NPD6672	Approved
0.587	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6903	Approved
0.5859	Remote Similarity	NPD5344	Discontinued
0.5851	Remote Similarity	NPD7637	Suspended
0.5851	Remote Similarity	NPD7983	Approved
0.5843	Remote Similarity	NPD5331	Approved
0.5843	Remote Similarity	NPD5332	Approved
0.5833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5926	Approved
0.5814	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD4271	Approved
0.5814	Remote Similarity	NPD4268	Approved
0.5806	Remote Similarity	NPD6673	Approved
0.5806	Remote Similarity	NPD6904	Approved
0.5806	Remote Similarity	NPD6080	Approved
0.5795	Remote Similarity	NPD4790	Discontinued
0.5795	Remote Similarity	NPD5369	Approved
0.5789	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5779	Approved
0.5789	Remote Similarity	NPD5778	Approved
0.5789	Remote Similarity	NPD1145	Discontinued
0.5761	Remote Similarity	NPD1282	Approved
0.5761	Remote Similarity	NPD3573	Approved
0.5755	Remote Similarity	NPD6053	Discontinued
0.573	Remote Similarity	NPD4270	Approved
0.573	Remote Similarity	NPD4269	Approved
0.573	Remote Similarity	NPD6435	Approved
0.5728	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6926	Approved
0.5714	Remote Similarity	NPD368	Approved
0.5714	Remote Similarity	NPD6924	Approved
0.5696	Remote Similarity	NPD7341	Phase 2
0.5684	Remote Similarity	NPD5281	Approved
0.5684	Remote Similarity	NPD5284	Approved
0.5673	Remote Similarity	NPD6686	Approved
0.567	Remote Similarity	NPD5695	Phase 3
0.567	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.567	Remote Similarity	NPD5654	Approved
0.5667	Remote Similarity	NPD6695	Phase 3
0.5652	Remote Similarity	NPD5786	Approved
0.5652	Remote Similarity	NPD6098	Approved
0.5638	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6101	Approved
0.5634	Remote Similarity	NPD29	Approved
0.5634	Remote Similarity	NPD28	Approved
0.5632	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD4211	Phase 1
0.5625	Remote Similarity	NPD7503	Approved
0.5612	Remote Similarity	NPD7839	Suspended
0.5604	Remote Similarity	NPD7338	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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