NPASS Compound

Structure

NPC26078 OpenBabel07101719252D 27 28 0 0 1 0 0 0 0 0999 V2000 7.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 -4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 0.0570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 3 15 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 14 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 27 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 2 1 6 0 0 0 14 18 1 0 0 0 0 15 20 2 0 0 0 0 15 27 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 22 4 1 1 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	400.088
LogP:	4.222
LogD:	2.909
LogS:	-4.863
# Rotatable Bonds:	9
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	4.282
Fsp3:	0.545
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:	-4.705
MDCK Permeability:	2.333440352231264e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.342

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	94.3218994140625%
Volume Distribution (VD):	2.987
Pgp-substrate:	5.086633205413818%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.797
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.884
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.837
CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.962
CYP3A4-substrate:	0.822

ADMET: Excretion

Clearance (CL):	2.093
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.349
Drug-inuced Liver Injury (DILI):	0.508
AMES Toxicity:	0.489
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.745
Skin Sensitization:	0.894
Carcinogencity:	0.911
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC26078

Natural Product ID:	NPC26078
*Common Name:**	Sequoiatone C
IUPAC Name:	methyl (6E,7R)-7-hydroxy-1,7-dimethyl-6-[(3S)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate
Synonyms:	Sequoiatone C
Standard InCHIKey:	DYUPDLYFDGWNBP-TVXHFNGESA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-6-7-8-9-10-14(2)18(23)13-17-19(21(24)26-5)16-11-12-27-15(3)20(16)22(17,4)25/h11-14,25H,6-10H2,1-5H3/b17-13+/t14-,22+/m0/s1
SMILES:	CCCCCC[C@H](C)C(=O)/C=C/1C(=C2C=COC(=C2[C@]1(C)O)C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495442
PubChem CID:	10915738
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans

*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
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678666]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027772]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15184162]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22103394]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24738739]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	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	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	=	260.0	uM	PMID[478459]

☑ 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 NPC26078 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	179
0.1-0.2	994
0.2-0.3	4258
0.3-0.4	9367
0.4-0.5	16979
0.5-0.6	7154
0.6-0.7	3266
0.7-0.8	493
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC51358
0.9759	High Similarity	NPC473658
0.9643	High Similarity	NPC307092
0.8214	Intermediate Similarity	NPC316324
0.8	Intermediate Similarity	NPC234038
0.7912	Intermediate Similarity	NPC72513
0.7907	Intermediate Similarity	NPC315765
0.7802	Intermediate Similarity	NPC316426
0.7802	Intermediate Similarity	NPC315395
0.7791	Intermediate Similarity	NPC315394
0.7778	Intermediate Similarity	NPC14575
0.7778	Intermediate Similarity	NPC196487
0.7742	Intermediate Similarity	NPC212598
0.7701	Intermediate Similarity	NPC93763
0.7701	Intermediate Similarity	NPC108816
0.7701	Intermediate Similarity	NPC267231
0.7677	Intermediate Similarity	NPC469851
0.767	Intermediate Similarity	NPC228477
0.767	Intermediate Similarity	NPC137911
0.7667	Intermediate Similarity	NPC16488
0.766	Intermediate Similarity	NPC179394
0.766	Intermediate Similarity	NPC144133
0.764	Intermediate Similarity	NPC325031
0.7609	Intermediate Similarity	NPC305475
0.7609	Intermediate Similarity	NPC475461
0.7609	Intermediate Similarity	NPC116575
0.76	Intermediate Similarity	NPC197835
0.76	Intermediate Similarity	NPC189609
0.76	Intermediate Similarity	NPC291500
0.76	Intermediate Similarity	NPC303653
0.76	Intermediate Similarity	NPC140591
0.7582	Intermediate Similarity	NPC141193
0.7582	Intermediate Similarity	NPC96259
0.7579	Intermediate Similarity	NPC111114
0.7579	Intermediate Similarity	NPC300312
0.7579	Intermediate Similarity	NPC261607
0.7579	Intermediate Similarity	NPC166110
0.7556	Intermediate Similarity	NPC85772
0.7553	Intermediate Similarity	NPC115179
0.7553	Intermediate Similarity	NPC106040
0.7553	Intermediate Similarity	NPC268298
0.7551	Intermediate Similarity	NPC208094
0.7527	Intermediate Similarity	NPC113370
0.7527	Intermediate Similarity	NPC103743
0.7527	Intermediate Similarity	NPC476079
0.7527	Intermediate Similarity	NPC160138
0.7526	Intermediate Similarity	NPC295347
0.7526	Intermediate Similarity	NPC304886
0.7526	Intermediate Similarity	NPC91408
0.75	Intermediate Similarity	NPC261380
0.75	Intermediate Similarity	NPC469657
0.75	Intermediate Similarity	NPC474369
0.75	Intermediate Similarity	NPC476049
0.75	Intermediate Similarity	NPC316029
0.75	Intermediate Similarity	NPC165162
0.75	Intermediate Similarity	NPC244456
0.75	Intermediate Similarity	NPC315597
0.75	Intermediate Similarity	NPC248193
0.75	Intermediate Similarity	NPC307112
0.75	Intermediate Similarity	NPC192006
0.75	Intermediate Similarity	NPC125290
0.75	Intermediate Similarity	NPC255307
0.75	Intermediate Similarity	NPC315285
0.7476	Intermediate Similarity	NPC469853
0.7474	Intermediate Similarity	NPC129419
0.7474	Intermediate Similarity	NPC475855
0.7474	Intermediate Similarity	NPC265856
0.7474	Intermediate Similarity	NPC166554
0.7473	Intermediate Similarity	NPC40746
0.7473	Intermediate Similarity	NPC250315
0.7473	Intermediate Similarity	NPC169575
0.7451	Intermediate Similarity	NPC309190
0.7447	Intermediate Similarity	NPC260343
0.7444	Intermediate Similarity	NPC42470
0.7444	Intermediate Similarity	NPC112868
0.7442	Intermediate Similarity	NPC227396
0.7423	Intermediate Similarity	NPC198853
0.7423	Intermediate Similarity	NPC167219
0.7423	Intermediate Similarity	NPC470010
0.7423	Intermediate Similarity	NPC477131
0.7423	Intermediate Similarity	NPC470013
0.7423	Intermediate Similarity	NPC262133
0.7423	Intermediate Similarity	NPC323008
0.7423	Intermediate Similarity	NPC53685
0.7419	Intermediate Similarity	NPC198314
0.7419	Intermediate Similarity	NPC122502
0.7416	Intermediate Similarity	NPC63649
0.7416	Intermediate Similarity	NPC472965
0.7416	Intermediate Similarity	NPC264227
0.7396	Intermediate Similarity	NPC193396
0.7396	Intermediate Similarity	NPC32944
0.7391	Intermediate Similarity	NPC476804
0.7391	Intermediate Similarity	NPC114979
0.7391	Intermediate Similarity	NPC470918
0.7391	Intermediate Similarity	NPC191476
0.7386	Intermediate Similarity	NPC116177
0.7386	Intermediate Similarity	NPC320630
0.7386	Intermediate Similarity	NPC7563
0.7379	Intermediate Similarity	NPC469852
0.7368	Intermediate Similarity	NPC95364
0.7368	Intermediate Similarity	NPC36668
0.7368	Intermediate Similarity	NPC118011
0.7368	Intermediate Similarity	NPC142159
0.7363	Intermediate Similarity	NPC474252
0.7353	Intermediate Similarity	NPC25666
0.7353	Intermediate Similarity	NPC271059
0.7347	Intermediate Similarity	NPC272050
0.7347	Intermediate Similarity	NPC209355
0.734	Intermediate Similarity	NPC472007
0.734	Intermediate Similarity	NPC237540
0.7333	Intermediate Similarity	NPC160582
0.7333	Intermediate Similarity	NPC47951
0.7327	Intermediate Similarity	NPC206079
0.7326	Intermediate Similarity	NPC238948
0.7326	Intermediate Similarity	NPC12815
0.7326	Intermediate Similarity	NPC215745
0.732	Intermediate Similarity	NPC475838
0.732	Intermediate Similarity	NPC125674
0.732	Intermediate Similarity	NPC1108
0.732	Intermediate Similarity	NPC228451
0.7312	Intermediate Similarity	NPC471185
0.7312	Intermediate Similarity	NPC470755
0.7312	Intermediate Similarity	NPC471223
0.7312	Intermediate Similarity	NPC78089
0.7312	Intermediate Similarity	NPC67081
0.7303	Intermediate Similarity	NPC128276
0.73	Intermediate Similarity	NPC141191
0.73	Intermediate Similarity	NPC64742
0.7292	Intermediate Similarity	NPC473448
0.7292	Intermediate Similarity	NPC145666
0.7292	Intermediate Similarity	NPC3436
0.7292	Intermediate Similarity	NPC469372
0.7292	Intermediate Similarity	NPC77337
0.729	Intermediate Similarity	NPC66108
0.729	Intermediate Similarity	NPC123855
0.729	Intermediate Similarity	NPC138757
0.729	Intermediate Similarity	NPC76550
0.7283	Intermediate Similarity	NPC473390
0.7283	Intermediate Similarity	NPC475083
0.7283	Intermediate Similarity	NPC131669
0.7282	Intermediate Similarity	NPC472868
0.7273	Intermediate Similarity	NPC172998
0.7273	Intermediate Similarity	NPC301596
0.7273	Intermediate Similarity	NPC299396
0.7273	Intermediate Similarity	NPC473223
0.7263	Intermediate Similarity	NPC476805
0.7263	Intermediate Similarity	NPC475819
0.7263	Intermediate Similarity	NPC60765
0.7262	Intermediate Similarity	NPC313444
0.7255	Intermediate Similarity	NPC471599
0.7255	Intermediate Similarity	NPC235369
0.7253	Intermediate Similarity	NPC141810
0.7253	Intermediate Similarity	NPC281949
0.7253	Intermediate Similarity	NPC25684
0.7253	Intermediate Similarity	NPC301477
0.7253	Intermediate Similarity	NPC24417
0.7253	Intermediate Similarity	NPC52861
0.7253	Intermediate Similarity	NPC471325
0.7245	Intermediate Similarity	NPC474247
0.7245	Intermediate Similarity	NPC477241
0.7245	Intermediate Similarity	NPC65829
0.7245	Intermediate Similarity	NPC474338
0.7241	Intermediate Similarity	NPC476355
0.7241	Intermediate Similarity	NPC470686
0.7238	Intermediate Similarity	NPC220155
0.7234	Intermediate Similarity	NPC261721
0.7234	Intermediate Similarity	NPC150755
0.7234	Intermediate Similarity	NPC164393
0.7234	Intermediate Similarity	NPC469483
0.7234	Intermediate Similarity	NPC472009
0.7234	Intermediate Similarity	NPC203795
0.7234	Intermediate Similarity	NPC107787
0.7222	Intermediate Similarity	NPC178277
0.7222	Intermediate Similarity	NPC469617
0.7222	Intermediate Similarity	NPC46269
0.7222	Intermediate Similarity	NPC270126
0.7222	Intermediate Similarity	NPC106395
0.7216	Intermediate Similarity	NPC45579
0.7216	Intermediate Similarity	NPC470520
0.7216	Intermediate Similarity	NPC133698
0.7216	Intermediate Similarity	NPC472705
0.7212	Intermediate Similarity	NPC478208
0.7212	Intermediate Similarity	NPC189863
0.7209	Intermediate Similarity	NPC288667
0.7204	Intermediate Similarity	NPC31086
0.7204	Intermediate Similarity	NPC295799
0.7204	Intermediate Similarity	NPC243618
0.7204	Intermediate Similarity	NPC115786
0.7204	Intermediate Similarity	NPC82297
0.7204	Intermediate Similarity	NPC70424
0.7204	Intermediate Similarity	NPC158756
0.72	Intermediate Similarity	NPC69385
0.72	Intermediate Similarity	NPC265662
0.72	Intermediate Similarity	NPC134083
0.72	Intermediate Similarity	NPC169205
0.72	Intermediate Similarity	NPC20066
0.72	Intermediate Similarity	NPC53844
0.72	Intermediate Similarity	NPC202705
0.72	Intermediate Similarity	NPC239895
0.7191	Intermediate Similarity	NPC41780

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 NPC26078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1384
0.2-0.3	3463
0.3-0.4	2688
0.4-0.5	1056
0.5-0.6	326
0.6-0.7	75
0.7-0.8	5
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
0.7667	Intermediate Similarity	NPD7154	Phase 3
0.7474	Intermediate Similarity	NPD5785	Approved
0.7473	Intermediate Similarity	NPD5362	Discontinued
0.7386	Intermediate Similarity	NPD4756	Discovery
0.7312	Intermediate Similarity	NPD5363	Approved
0.7174	Intermediate Similarity	NPD4270	Approved
0.7174	Intermediate Similarity	NPD4269	Approved
0.7065	Intermediate Similarity	NPD5369	Approved
0.7053	Intermediate Similarity	NPD5786	Approved
0.7041	Intermediate Similarity	NPD5284	Approved
0.7041	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4252	Approved
0.6957	Remote Similarity	NPD4821	Approved
0.6957	Remote Similarity	NPD4820	Approved
0.6957	Remote Similarity	NPD4822	Approved
0.6957	Remote Similarity	NPD4819	Approved
0.6944	Remote Similarity	NPD6371	Approved
0.6939	Remote Similarity	NPD46	Approved
0.6939	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5282	Discontinued
0.6818	Remote Similarity	NPD6053	Discontinued
0.6809	Remote Similarity	NPD5209	Approved
0.6778	Remote Similarity	NPD8039	Approved
0.6774	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1694	Approved
0.6739	Remote Similarity	NPD4268	Approved
0.6739	Remote Similarity	NPD4271	Approved
0.6737	Remote Similarity	NPD5332	Approved
0.6737	Remote Similarity	NPD5331	Approved
0.6702	Remote Similarity	NPD4790	Discontinued
0.6701	Remote Similarity	NPD4249	Approved
0.67	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1695	Approved
0.6634	Remote Similarity	NPD5778	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.6633	Remote Similarity	NPD4250	Approved
0.6633	Remote Similarity	NPD4251	Approved
0.6632	Remote Similarity	NPD6435	Approved
0.6632	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7838	Discovery
0.6596	Remote Similarity	NPD5368	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6505	Remote Similarity	NPD5695	Phase 3
0.6476	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD6399	Phase 3
0.6458	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7839	Suspended
0.6437	Remote Similarity	NPD3704	Approved
0.6437	Remote Similarity	NPD7331	Phase 2
0.6436	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD1696	Phase 3
0.6429	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4518	Approved
0.6381	Remote Similarity	NPD6084	Phase 2
0.6381	Remote Similarity	NPD6083	Phase 2
0.6373	Remote Similarity	NPD5693	Phase 1
0.6373	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7637	Suspended
0.6373	Remote Similarity	NPD5694	Approved
0.6364	Remote Similarity	NPD4623	Approved
0.6364	Remote Similarity	NPD4519	Discontinued
0.6339	Remote Similarity	NPD2067	Discontinued
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5370	Suspended
0.6337	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5909	Discontinued
0.6327	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7341	Phase 2
0.6321	Remote Similarity	NPD4225	Approved
0.6279	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5692	Phase 3
0.6263	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6648	Approved
0.6262	Remote Similarity	NPD7639	Approved
0.6262	Remote Similarity	NPD7640	Approved
0.6239	Remote Similarity	NPD6647	Phase 2
0.6218	Remote Similarity	NPD8513	Phase 3
0.6216	Remote Similarity	NPD5697	Approved
0.6214	Remote Similarity	NPD6411	Approved
0.6214	Remote Similarity	NPD6050	Approved
0.62	Remote Similarity	NPD4694	Approved
0.62	Remote Similarity	NPD5279	Phase 3
0.62	Remote Similarity	NPD5280	Approved
0.619	Remote Similarity	NPD5210	Approved
0.619	Remote Similarity	NPD4629	Approved
0.6176	Remote Similarity	NPD4753	Phase 2
0.6168	Remote Similarity	NPD7638	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6147	Remote Similarity	NPD5211	Phase 2
0.614	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD5739	Approved
0.6126	Remote Similarity	NPD7128	Approved
0.6126	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD6675	Approved
0.6122	Remote Similarity	NPD4223	Phase 3
0.6122	Remote Similarity	NPD4221	Approved
0.6106	Remote Similarity	NPD6372	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6106	Remote Similarity	NPD6373	Approved
0.6083	Remote Similarity	NPD8516	Approved
0.6083	Remote Similarity	NPD8515	Approved
0.6083	Remote Similarity	NPD8517	Approved
0.6082	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4695	Discontinued
0.6078	Remote Similarity	NPD6672	Approved
0.6078	Remote Similarity	NPD5737	Approved
0.6075	Remote Similarity	NPD7902	Approved
0.6071	Remote Similarity	NPD5701	Approved
0.6067	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6110	Phase 1
0.6055	Remote Similarity	NPD5344	Discontinued
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.6047	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5330	Approved
0.604	Remote Similarity	NPD7334	Approved
0.604	Remote Similarity	NPD5690	Phase 2
0.604	Remote Similarity	NPD6409	Approved
0.604	Remote Similarity	NPD7521	Approved
0.604	Remote Similarity	NPD7146	Approved
0.604	Remote Similarity	NPD6684	Approved
0.6038	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5654	Approved
0.6036	Remote Similarity	NPD5141	Approved
0.6019	Remote Similarity	NPD6904	Approved
0.6019	Remote Similarity	NPD6673	Approved
0.6019	Remote Similarity	NPD6080	Approved
0.6018	Remote Similarity	NPD6686	Approved
0.6018	Remote Similarity	NPD7320	Approved
0.6017	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD4197	Approved
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6847	Approved
0.5982	Remote Similarity	NPD6008	Approved
0.5977	Remote Similarity	NPD4194	Approved
0.5977	Remote Similarity	NPD4193	Approved
0.5977	Remote Similarity	NPD4192	Approved
0.5977	Remote Similarity	NPD4191	Approved
0.5963	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD5286	Approved
0.5963	Remote Similarity	NPD5285	Approved
0.5962	Remote Similarity	NPD4096	Approved
0.595	Remote Similarity	NPD7503	Approved
0.5948	Remote Similarity	NPD6882	Approved
0.5948	Remote Similarity	NPD8297	Approved
0.5943	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7748	Approved
0.5941	Remote Similarity	NPD5329	Approved
0.5932	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5959	Approved
0.5926	Remote Similarity	NPD4755	Approved
0.5922	Remote Similarity	NPD6903	Approved
0.5922	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5208	Approved
0.5918	Remote Similarity	NPD7332	Phase 2
0.5913	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5223	Approved
0.5906	Remote Similarity	NPD7260	Phase 2
0.5905	Remote Similarity	NPD7515	Phase 2
0.5897	Remote Similarity	NPD4632	Approved
0.5882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4688	Approved
0.5882	Remote Similarity	NPD4689	Approved
0.5882	Remote Similarity	NPD5205	Approved
0.5882	Remote Similarity	NPD4690	Approved
0.5882	Remote Similarity	NPD4693	Phase 3
0.5882	Remote Similarity	NPD3618	Phase 1
0.5882	Remote Similarity	NPD4138	Approved
0.5868	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5226	Approved
0.5856	Remote Similarity	NPD4633	Approved
0.5856	Remote Similarity	NPD5224	Approved
0.5856	Remote Similarity	NPD5225	Approved
0.5856	Remote Similarity	NPD7632	Discontinued
0.5849	Remote Similarity	NPD5133	Approved
0.5843	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5842	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