NPASS Compound

Structure

NPC104644 OpenBabel07101719152D 25 25 0 0 1 0 0 0 0 0999 V2000 -1.2247 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 15 2 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 21 1 0 0 0 0 7 21 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 16 2 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 16 1 6 0 0 0 19 22 1 6 0 0 0 20 11 1 1 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 22 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.27
Volume:	396.337
LogP:	4.336
LogD:	3.972
LogS:	-4.236
# Rotatable Bonds:	8
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.507
Synthetic Accessibility Score:	4.598
Fsp3:	0.682
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:	-4.562
MDCK Permeability:	2.5469038519077003e-05
Pgp-inhibitor:	0.884
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.634
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	89.69487762451172%
Volume Distribution (VD):	1.676
Pgp-substrate:	10.107913970947266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.638
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.586
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	3.016
Half-life (T1/2):	0.333

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.88
Carcinogencity:	0.092
Eye Corrosion:	0.362
Eye Irritation:	0.728
Respiratory Toxicity:	0.679

Download Data

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

Natural Product: NPC104644

Natural Product ID:	NPC104644
*Common Name:**	Loba-8,10,13(15)-Triene-17,18-Diol-18-Acetate
IUPAC Name:	[(E,3R)-6-[(1S,3R,4R)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-2-hydroxy-2-methylhept-5-en-3-yl] acetate
Synonyms:
Standard InCHIKey:	NSAAWTDAMZJSEO-RMQVCNTQSA-N
Standard InCHI:	InChI=1S/C22H36O3/c1-9-22(8)13-12-18(14-19(22)15(2)3)16(4)10-11-20(21(6,7)24)25-17(5)23/h9-10,18-20,24H,1-2,11-14H2,3-8H3/b16-10+/t18-,19+,20+,22-/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@H](C[C@@H]1C(=C)C)/C(=C/C[C@H](C(O)(C)C)OC(=O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476286
PubChem CID:	10593890
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209732]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	Mindoro, Philippines	n.a.	PMID[9548875]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	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
Others	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	13.0	mm	PMID[485522]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	9.0	mm	PMID[485522]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	5.0	mm	PMID[485522]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	2.0	mm	PMID[485522]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	19.1	ug.mL-1	PMID[485522]

☑ 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 NPC104644 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	152
0.1-0.2	1178
0.2-0.3	6630
0.3-0.4	15718
0.4-0.5	7704
0.5-0.6	8069
0.6-0.7	3128
0.7-0.8	111
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8831	High Similarity	NPC49208
0.8696	High Similarity	NPC250977
0.859	High Similarity	NPC23748
0.8205	Intermediate Similarity	NPC233332
0.8077	Intermediate Similarity	NPC233295
0.8077	Intermediate Similarity	NPC100906
0.8052	Intermediate Similarity	NPC283619
0.8	Intermediate Similarity	NPC283247
0.7975	Intermediate Similarity	NPC474592
0.7952	Intermediate Similarity	NPC245004
0.7895	Intermediate Similarity	NPC71152
0.7875	Intermediate Similarity	NPC142163
0.7821	Intermediate Similarity	NPC40049
0.7792	Intermediate Similarity	NPC113639
0.7791	Intermediate Similarity	NPC303697
0.7765	Intermediate Similarity	NPC20946
0.7738	Intermediate Similarity	NPC131329
0.7711	Intermediate Similarity	NPC35933
0.7683	Intermediate Similarity	NPC42476
0.7654	Intermediate Similarity	NPC327002
0.7654	Intermediate Similarity	NPC25554
0.7639	Intermediate Similarity	NPC329698
0.7625	Intermediate Similarity	NPC242767
0.7595	Intermediate Similarity	NPC325946
0.7564	Intermediate Similarity	NPC12696
0.7561	Intermediate Similarity	NPC16321
0.7558	Intermediate Similarity	NPC82876
0.7528	Intermediate Similarity	NPC275310
0.7528	Intermediate Similarity	NPC286612
0.7528	Intermediate Similarity	NPC230347
0.75	Intermediate Similarity	NPC189745
0.75	Intermediate Similarity	NPC329738
0.75	Intermediate Similarity	NPC471795
0.75	Intermediate Similarity	NPC321514
0.747	Intermediate Similarity	NPC52108
0.747	Intermediate Similarity	NPC474789
0.747	Intermediate Similarity	NPC476927
0.7467	Intermediate Similarity	NPC273508
0.7467	Intermediate Similarity	NPC209327
0.7442	Intermediate Similarity	NPC309656
0.7436	Intermediate Similarity	NPC160540
0.7416	Intermediate Similarity	NPC215700
0.7412	Intermediate Similarity	NPC175145
0.7412	Intermediate Similarity	NPC324063
0.7412	Intermediate Similarity	NPC474970
0.7412	Intermediate Similarity	NPC475069
0.7407	Intermediate Similarity	NPC327674
0.7407	Intermediate Similarity	NPC153987
0.7407	Intermediate Similarity	NPC44083
0.7381	Intermediate Similarity	NPC306951
0.7363	Intermediate Similarity	NPC239547
0.7363	Intermediate Similarity	NPC155319
0.7363	Intermediate Similarity	NPC125551
0.7363	Intermediate Similarity	NPC309503
0.7363	Intermediate Similarity	NPC91197
0.7363	Intermediate Similarity	NPC96597
0.7356	Intermediate Similarity	NPC79027
0.7356	Intermediate Similarity	NPC246028
0.7349	Intermediate Similarity	NPC256112
0.7333	Intermediate Similarity	NPC193029
0.7333	Intermediate Similarity	NPC473357
0.7317	Intermediate Similarity	NPC103634
0.7308	Intermediate Similarity	NPC471799
0.7303	Intermediate Similarity	NPC53555
0.7294	Intermediate Similarity	NPC191965
0.7294	Intermediate Similarity	NPC476602
0.7284	Intermediate Similarity	NPC179028
0.7284	Intermediate Similarity	NPC167891
0.7284	Intermediate Similarity	NPC83351
0.7273	Intermediate Similarity	NPC214844
0.7273	Intermediate Similarity	NPC15059
0.7262	Intermediate Similarity	NPC161045
0.7262	Intermediate Similarity	NPC473592
0.7253	Intermediate Similarity	NPC471903
0.725	Intermediate Similarity	NPC265588
0.7241	Intermediate Similarity	NPC474629
0.7237	Intermediate Similarity	NPC208999
0.7234	Intermediate Similarity	NPC11956
0.7229	Intermediate Similarity	NPC473420
0.7229	Intermediate Similarity	NPC170303
0.7229	Intermediate Similarity	NPC70927
0.7229	Intermediate Similarity	NPC159148
0.7229	Intermediate Similarity	NPC108476
0.7229	Intermediate Similarity	NPC118116
0.7222	Intermediate Similarity	NPC469491
0.7222	Intermediate Similarity	NPC211238
0.7215	Intermediate Similarity	NPC168975
0.7215	Intermediate Similarity	NPC75485
0.7215	Intermediate Similarity	NPC471797
0.7209	Intermediate Similarity	NPC137306
0.7209	Intermediate Similarity	NPC471219
0.7209	Intermediate Similarity	NPC73038
0.7209	Intermediate Similarity	NPC325594
0.7209	Intermediate Similarity	NPC84121
0.7204	Intermediate Similarity	NPC473510
0.7204	Intermediate Similarity	NPC38855
0.72	Intermediate Similarity	NPC242945
0.72	Intermediate Similarity	NPC259156
0.7195	Intermediate Similarity	NPC328714
0.7195	Intermediate Similarity	NPC192999
0.7195	Intermediate Similarity	NPC476438
0.7195	Intermediate Similarity	NPC471537
0.7191	Intermediate Similarity	NPC177641
0.7191	Intermediate Similarity	NPC208839
0.7179	Intermediate Similarity	NPC242001
0.7179	Intermediate Similarity	NPC160817
0.7179	Intermediate Similarity	NPC477983
0.7179	Intermediate Similarity	NPC167706
0.7179	Intermediate Similarity	NPC477981
0.7179	Intermediate Similarity	NPC472254
0.7176	Intermediate Similarity	NPC102048
0.7174	Intermediate Similarity	NPC475032
0.7174	Intermediate Similarity	NPC475033
0.7174	Intermediate Similarity	NPC124246
0.7174	Intermediate Similarity	NPC210337
0.7162	Intermediate Similarity	NPC290367
0.716	Intermediate Similarity	NPC262747
0.716	Intermediate Similarity	NPC132542
0.7159	Intermediate Similarity	NPC309310
0.7159	Intermediate Similarity	NPC473647
0.7158	Intermediate Similarity	NPC23584
0.7143	Intermediate Similarity	NPC474979
0.7143	Intermediate Similarity	NPC101622
0.7143	Intermediate Similarity	NPC471159
0.7143	Intermediate Similarity	NPC329656
0.7143	Intermediate Similarity	NPC103171
0.7143	Intermediate Similarity	NPC471218
0.7143	Intermediate Similarity	NPC2524
0.7143	Intermediate Similarity	NPC471408
0.7143	Intermediate Similarity	NPC73882
0.7143	Intermediate Similarity	NPC123880
0.7143	Intermediate Similarity	NPC15910
0.7128	Intermediate Similarity	NPC233012
0.7128	Intermediate Similarity	NPC54909
0.7128	Intermediate Similarity	NPC121072
0.7128	Intermediate Similarity	NPC472554
0.7128	Intermediate Similarity	NPC21064
0.7126	Intermediate Similarity	NPC477926
0.7126	Intermediate Similarity	NPC473097
0.7126	Intermediate Similarity	NPC128644
0.7126	Intermediate Similarity	NPC167877
0.7126	Intermediate Similarity	NPC471796
0.7126	Intermediate Similarity	NPC166857
0.7125	Intermediate Similarity	NPC66566
0.7125	Intermediate Similarity	NPC477923
0.7108	Intermediate Similarity	NPC206735
0.7108	Intermediate Similarity	NPC269791
0.7108	Intermediate Similarity	NPC281880
0.7105	Intermediate Similarity	NPC114651
0.7097	Intermediate Similarity	NPC470066
0.7097	Intermediate Similarity	NPC477876
0.7097	Intermediate Similarity	NPC247233
0.7097	Intermediate Similarity	NPC477875
0.7097	Intermediate Similarity	NPC470067
0.7097	Intermediate Similarity	NPC470068
0.7093	Intermediate Similarity	NPC109528
0.7093	Intermediate Similarity	NPC164424
0.7093	Intermediate Similarity	NPC11804
0.7093	Intermediate Similarity	NPC471494
0.7093	Intermediate Similarity	NPC329630
0.7093	Intermediate Similarity	NPC290731
0.7089	Intermediate Similarity	NPC144947
0.7079	Intermediate Similarity	NPC78973
0.7079	Intermediate Similarity	NPC473269
0.7079	Intermediate Similarity	NPC474728
0.7079	Intermediate Similarity	NPC159876
0.7079	Intermediate Similarity	NPC472466
0.7073	Intermediate Similarity	NPC279532
0.7073	Intermediate Similarity	NPC209135
0.7073	Intermediate Similarity	NPC474816
0.7067	Intermediate Similarity	NPC107258
0.7065	Intermediate Similarity	NPC88009
0.7065	Intermediate Similarity	NPC230151
0.7065	Intermediate Similarity	NPC469369
0.7065	Intermediate Similarity	NPC469528
0.7065	Intermediate Similarity	NPC57664
0.7059	Intermediate Similarity	NPC311070
0.7059	Intermediate Similarity	NPC132386
0.7059	Intermediate Similarity	NPC474809
0.7059	Intermediate Similarity	NPC470948
0.7059	Intermediate Similarity	NPC239308
0.7053	Intermediate Similarity	NPC470571
0.7053	Intermediate Similarity	NPC473163
0.7053	Intermediate Similarity	NPC154452
0.7053	Intermediate Similarity	NPC472552
0.7051	Intermediate Similarity	NPC473361
0.7051	Intermediate Similarity	NPC34834
0.7051	Intermediate Similarity	NPC4299
0.7051	Intermediate Similarity	NPC329904
0.7051	Intermediate Similarity	NPC145498
0.7045	Intermediate Similarity	NPC254572
0.7045	Intermediate Similarity	NPC255176
0.7045	Intermediate Similarity	NPC24816
0.7045	Intermediate Similarity	NPC250687
0.7045	Intermediate Similarity	NPC229407
0.7045	Intermediate Similarity	NPC48824
0.7037	Intermediate Similarity	NPC477925
0.7037	Intermediate Similarity	NPC69143
0.7037	Intermediate Similarity	NPC470766
0.7037	Intermediate Similarity	NPC315261

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 NPC104644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	1565
0.2-0.3	4230
0.3-0.4	2285
0.4-0.5	549
0.5-0.6	317
0.6-0.7	70
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
0.7037	Intermediate Similarity	NPD6933	Approved
0.6933	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6399	Phase 3
0.6835	Remote Similarity	NPD7143	Approved
0.6835	Remote Similarity	NPD7144	Approved
0.6813	Remote Similarity	NPD7637	Suspended
0.679	Remote Similarity	NPD6924	Approved
0.679	Remote Similarity	NPD6926	Approved
0.675	Remote Similarity	NPD7150	Approved
0.675	Remote Similarity	NPD7152	Approved
0.675	Remote Similarity	NPD7151	Approved
0.6747	Remote Similarity	NPD6932	Approved
0.6742	Remote Similarity	NPD7524	Approved
0.6737	Remote Similarity	NPD4225	Approved
0.6709	Remote Similarity	NPD6923	Approved
0.6709	Remote Similarity	NPD6922	Approved
0.6707	Remote Similarity	NPD7339	Approved
0.6707	Remote Similarity	NPD8264	Approved
0.6707	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7748	Approved
0.663	Remote Similarity	NPD6411	Approved
0.6629	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD7146	Approved
0.6629	Remote Similarity	NPD6409	Approved
0.6629	Remote Similarity	NPD7334	Approved
0.6629	Remote Similarity	NPD6684	Approved
0.6629	Remote Similarity	NPD5330	Approved
0.6627	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5344	Discontinued
0.6593	Remote Similarity	NPD6051	Approved
0.6591	Remote Similarity	NPD4786	Approved
0.6591	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7645	Phase 2
0.6585	Remote Similarity	NPD4784	Approved
0.6585	Remote Similarity	NPD4785	Approved
0.6552	Remote Similarity	NPD3667	Approved
0.6512	Remote Similarity	NPD7514	Phase 3
0.6512	Remote Similarity	NPD7525	Registered
0.6512	Remote Similarity	NPD7332	Phase 2
0.6486	Remote Similarity	NPD6109	Phase 1
0.6484	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6903	Approved
0.6477	Remote Similarity	NPD6695	Phase 3
0.6471	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7145	Approved
0.6458	Remote Similarity	NPD6084	Phase 2
0.6458	Remote Similarity	NPD6083	Phase 2
0.6458	Remote Similarity	NPD7902	Approved
0.6452	Remote Similarity	NPD7515	Phase 2
0.6447	Remote Similarity	NPD4193	Approved
0.6447	Remote Similarity	NPD4194	Approved
0.6447	Remote Similarity	NPD4192	Approved
0.6447	Remote Similarity	NPD4191	Approved
0.6437	Remote Similarity	NPD5369	Approved
0.6421	Remote Similarity	NPD5695	Phase 3
0.6413	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6101	Approved
0.641	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4195	Approved
0.6395	Remote Similarity	NPD6683	Phase 2
0.6392	Remote Similarity	NPD7638	Approved
0.6355	Remote Similarity	NPD7115	Discovery
0.6354	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5776	Phase 2
0.6353	Remote Similarity	NPD6925	Approved
0.6344	Remote Similarity	NPD6698	Approved
0.6344	Remote Similarity	NPD7838	Discovery
0.6344	Remote Similarity	NPD46	Approved
0.6341	Remote Similarity	NPD4243	Approved
0.6327	Remote Similarity	NPD7640	Approved
0.6327	Remote Similarity	NPD6648	Approved
0.6327	Remote Similarity	NPD7639	Approved
0.6322	Remote Similarity	NPD4820	Approved
0.6322	Remote Similarity	NPD6930	Phase 2
0.6322	Remote Similarity	NPD6931	Approved
0.6322	Remote Similarity	NPD4819	Approved
0.6322	Remote Similarity	NPD4821	Approved
0.6322	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7509	Discontinued
0.6322	Remote Similarity	NPD4822	Approved
0.631	Remote Similarity	NPD8039	Approved
0.6304	Remote Similarity	NPD6672	Approved
0.6304	Remote Similarity	NPD5737	Approved
0.6292	Remote Similarity	NPD7154	Phase 3
0.6292	Remote Similarity	NPD5362	Discontinued
0.6286	Remote Similarity	NPD8297	Approved
0.6277	Remote Similarity	NPD7983	Approved
0.6264	Remote Similarity	NPD6098	Approved
0.625	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD6898	Phase 1
0.6234	Remote Similarity	NPD368	Approved
0.6224	Remote Similarity	NPD5696	Approved
0.6222	Remote Similarity	NPD3666	Approved
0.6222	Remote Similarity	NPD3665	Phase 1
0.6222	Remote Similarity	NPD3133	Approved
0.6214	Remote Similarity	NPD6881	Approved
0.6214	Remote Similarity	NPD6899	Approved
0.6214	Remote Similarity	NPD6686	Approved
0.6211	Remote Similarity	NPD5778	Approved
0.6211	Remote Similarity	NPD5779	Approved
0.6207	Remote Similarity	NPD6929	Approved
0.6196	Remote Similarity	NPD3573	Approved
0.6196	Remote Similarity	NPD7750	Discontinued
0.618	Remote Similarity	NPD6435	Approved
0.618	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6402	Approved
0.6176	Remote Similarity	NPD7128	Approved
0.6176	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD6675	Approved
0.6154	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7900	Approved
0.6146	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5697	Approved
0.6117	Remote Similarity	NPD6412	Phase 2
0.6111	Remote Similarity	NPD5332	Approved
0.6111	Remote Similarity	NPD5331	Approved
0.6105	Remote Similarity	NPD8034	Phase 2
0.6105	Remote Similarity	NPD8035	Phase 2
0.6105	Remote Similarity	NPD5284	Approved
0.6105	Remote Similarity	NPD5281	Approved
0.6105	Remote Similarity	NPD6079	Approved
0.6095	Remote Similarity	NPD7290	Approved
0.6095	Remote Similarity	NPD7102	Approved
0.6095	Remote Similarity	NPD6883	Approved
0.6092	Remote Similarity	NPD4271	Approved
0.6092	Remote Similarity	NPD4268	Approved
0.6087	Remote Similarity	NPD3618	Phase 1
0.6076	Remote Similarity	NPD3197	Phase 1
0.6075	Remote Similarity	NPD4632	Approved
0.6067	Remote Similarity	NPD4790	Discontinued
0.6064	Remote Similarity	NPD5328	Approved
0.6064	Remote Similarity	NPD6673	Approved
0.6064	Remote Similarity	NPD6080	Approved
0.6064	Remote Similarity	NPD6904	Approved
0.6064	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7320	Approved
0.6058	Remote Similarity	NPD6011	Approved
0.6044	Remote Similarity	NPD3668	Phase 3
0.6038	Remote Similarity	NPD6847	Approved
0.6038	Remote Similarity	NPD8130	Phase 1
0.6038	Remote Similarity	NPD6650	Approved
0.6038	Remote Similarity	NPD6617	Approved
0.6038	Remote Similarity	NPD6869	Approved
0.6038	Remote Similarity	NPD6649	Approved
0.6022	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD4219	Approved
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD4223	Phase 3
0.6	Remote Similarity	NPD6373	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD6012	Approved
0.5982	Remote Similarity	NPD7503	Approved
0.5982	Remote Similarity	NPD8033	Approved
0.5981	Remote Similarity	NPD6882	Approved
0.5978	Remote Similarity	NPD1694	Approved
0.5978	Remote Similarity	NPD5329	Approved
0.5978	Remote Similarity	NPD6893	Approved
0.5978	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5701	Approved
0.5957	Remote Similarity	NPD5208	Approved
0.5955	Remote Similarity	NPD5368	Approved
0.5955	Remote Similarity	NPD4695	Discontinued
0.5955	Remote Similarity	NPD4748	Discontinued
0.5955	Remote Similarity	NPD4252	Approved
0.5946	Remote Similarity	NPD7516	Approved
0.5938	Remote Similarity	NPD5694	Approved
0.5938	Remote Similarity	NPD7087	Discontinued
0.5938	Remote Similarity	NPD6050	Approved
0.593	Remote Similarity	NPD4190	Phase 3
0.593	Remote Similarity	NPD5275	Approved
0.5918	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5786	Approved
0.5914	Remote Similarity	NPD5279	Phase 3
0.5914	Remote Similarity	NPD4519	Discontinued
0.5914	Remote Similarity	NPD5690	Phase 2
0.5914	Remote Similarity	NPD6422	Discontinued
0.5914	Remote Similarity	NPD4623	Approved
0.5905	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4137	Phase 3
0.5897	Remote Similarity	NPD1145	Discontinued
0.5895	Remote Similarity	NPD4753	Phase 2
0.5893	Remote Similarity	NPD8294	Approved
0.5893	Remote Similarity	NPD6319	Approved
0.5893	Remote Similarity	NPD8377	Approved
0.5888	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4732	Discontinued
0.5876	Remote Similarity	NPD4202	Approved
0.587	Remote Similarity	NPD4197	Approved

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