NPASS Compound

Structure

NPC475944 OpenBabel07101718232D 30 31 0 0 1 0 0 0 0 0999 V2000 -4.3871 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8512 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7532 -0.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2532 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 -2.0878 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 -5.2532 -2.0878 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 -6.1192 -1.5878 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 -6.1192 1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2532 0.9122 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 -0.9230 -0.5878 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 -4.3871 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9852 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9230 -1.5878 0.0000 C 0 0 0 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 -6.1192 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9852 0.9122 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2532 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 -0.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3122 0.3601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8512 1.4122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 17 2 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 19 2 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 25 1 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 27 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 29 2 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.27
Volume:	454.612
LogP:	2.839
LogD:	3.041
LogS:	-3.827
# Rotatable Bonds:	10
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.404
Synthetic Accessibility Score:	4.276
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.09
MDCK Permeability:	6.96017832524376e-06
Pgp-inhibitor:	0.07
Pgp-substrate:	0.276
Human Intestinal Absorption (HIA):	0.103
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	87.80288696289062%
Volume Distribution (VD):	1.483
Pgp-substrate:	3.558161497116089%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.25
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.188
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.294

ADMET: Excretion

Clearance (CL):	7.073
Half-life (T1/2):	0.944

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.132
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.356
Skin Sensitization:	0.227
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC475944

Natural Product ID:	NPC475944
*Common Name:**	Luffariolide F
IUPAC Name:	3-(hydroxymethyl)-2-[(2Z,6E)-3-(hydroxymethyl)-9-(3-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-7-methylnona-2,6-dienyl]-2H-furan-5-one
Synonyms:	Luffariolide F
Standard InCHIKey:	BKHHGIGVYWPIJC-GPKGBNBSSA-N
Standard InCHI:	InChI=1S/C25H38O5/c1-17(8-10-21-18(2)22(28)12-13-25(21,3)4)6-5-7-19(15-26)9-11-23-20(16-27)14-24(29)30-23/h6,9,14,22-23,26-28H,5,7-8,10-13,15-16H2,1-4H3/b17-6+,19-9-
SMILES:	CC1=C(C(CCC1O)(C)C)CCC(=CCCC(=CCC2C(=CC(=O)O2)CO)CO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519166
PubChem CID:	10047645
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO32622	luffariella sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1624940]
NPO32622	luffariella sp.	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[8482949]

☑ 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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	1.6	ug.mL-1	PMID[492292]
NPT91	Cell Line	KB	Homo sapiens	GI	=	33.4	%	PMID[492292]

☑ 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 NPC475944 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	161
0.1-0.2	1141
0.2-0.3	4919
0.3-0.4	14193
0.4-0.5	10998
0.5-0.6	6628
0.6-0.7	3892
0.7-0.8	692
0.8-0.85	47
0.85-0.9	18
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC209135
0.96	High Similarity	NPC474816
0.9487	High Similarity	NPC474809
0.9467	High Similarity	NPC262747
0.9241	High Similarity	NPC471297
0.9114	High Similarity	NPC471298
0.9114	High Similarity	NPC323251
0.8933	High Similarity	NPC222244
0.8933	High Similarity	NPC16349
0.8889	High Similarity	NPC126518
0.8889	High Similarity	NPC474865
0.8889	High Similarity	NPC31086
0.878	High Similarity	NPC163606
0.8765	High Similarity	NPC472377
0.8706	High Similarity	NPC78973
0.869	High Similarity	NPC472378
0.8659	High Similarity	NPC471301
0.8659	High Similarity	NPC471302
0.8537	High Similarity	NPC42476
0.8537	High Similarity	NPC311070
0.8481	Intermediate Similarity	NPC473756
0.8452	Intermediate Similarity	NPC131813
0.8421	Intermediate Similarity	NPC4299
0.8415	Intermediate Similarity	NPC324170
0.8409	Intermediate Similarity	NPC104925
0.8409	Intermediate Similarity	NPC298973
0.8372	Intermediate Similarity	NPC470734
0.8354	Intermediate Similarity	NPC477202
0.8353	Intermediate Similarity	NPC312561
0.8313	Intermediate Similarity	NPC474193
0.8313	Intermediate Similarity	NPC12283
0.8295	Intermediate Similarity	NPC53555
0.8295	Intermediate Similarity	NPC472812
0.8289	Intermediate Similarity	NPC101622
0.8276	Intermediate Similarity	NPC281942
0.8276	Intermediate Similarity	NPC232426
0.8272	Intermediate Similarity	NPC471299
0.8256	Intermediate Similarity	NPC472810
0.8256	Intermediate Similarity	NPC472809
0.8256	Intermediate Similarity	NPC474629
0.825	Intermediate Similarity	NPC477203
0.8214	Intermediate Similarity	NPC160517
0.8214	Intermediate Similarity	NPC78673
0.8214	Intermediate Similarity	NPC186155
0.8202	Intermediate Similarity	NPC469697
0.8193	Intermediate Similarity	NPC471218
0.8182	Intermediate Similarity	NPC141831
0.8182	Intermediate Similarity	NPC469660
0.8182	Intermediate Similarity	NPC472811
0.8132	Intermediate Similarity	NPC53844
0.8125	Intermediate Similarity	NPC469880
0.8118	Intermediate Similarity	NPC471795
0.8118	Intermediate Similarity	NPC474860
0.8118	Intermediate Similarity	NPC471300
0.8118	Intermediate Similarity	NPC35933
0.8111	Intermediate Similarity	NPC276110
0.809	Intermediate Similarity	NPC152778
0.809	Intermediate Similarity	NPC162615
0.809	Intermediate Similarity	NPC205034
0.8068	Intermediate Similarity	NPC221111
0.8068	Intermediate Similarity	NPC280149
0.8049	Intermediate Similarity	NPC242767
0.8049	Intermediate Similarity	NPC139712
0.8026	Intermediate Similarity	NPC472266
0.8023	Intermediate Similarity	NPC61527
0.8022	Intermediate Similarity	NPC16967
0.8022	Intermediate Similarity	NPC165632
0.8022	Intermediate Similarity	NPC162346
0.8	Intermediate Similarity	NPC282760
0.7978	Intermediate Similarity	NPC329842
0.7978	Intermediate Similarity	NPC72845
0.7976	Intermediate Similarity	NPC256112
0.7975	Intermediate Similarity	NPC477085
0.7957	Intermediate Similarity	NPC38855
0.7931	Intermediate Similarity	NPC476600
0.7931	Intermediate Similarity	NPC199382
0.7931	Intermediate Similarity	NPC166857
0.7927	Intermediate Similarity	NPC184737
0.7907	Intermediate Similarity	NPC42586
0.7907	Intermediate Similarity	NPC11804
0.7907	Intermediate Similarity	NPC473251
0.7889	Intermediate Similarity	NPC115021
0.7889	Intermediate Similarity	NPC139692
0.7889	Intermediate Similarity	NPC472954
0.7882	Intermediate Similarity	NPC161045
0.7882	Intermediate Similarity	NPC23748
0.7865	Intermediate Similarity	NPC182136
0.7865	Intermediate Similarity	NPC310479
0.7857	Intermediate Similarity	NPC315731
0.7857	Intermediate Similarity	NPC112868
0.7857	Intermediate Similarity	NPC170303
0.7857	Intermediate Similarity	NPC159148
0.7849	Intermediate Similarity	NPC275086
0.7849	Intermediate Similarity	NPC325229
0.7848	Intermediate Similarity	NPC472254
0.7848	Intermediate Similarity	NPC477087
0.7848	Intermediate Similarity	NPC477086
0.7848	Intermediate Similarity	NPC257618
0.7826	Intermediate Similarity	NPC234993
0.7826	Intermediate Similarity	NPC242848
0.7826	Intermediate Similarity	NPC473153
0.7826	Intermediate Similarity	NPC134072
0.7816	Intermediate Similarity	NPC471219
0.7816	Intermediate Similarity	NPC477668
0.7805	Intermediate Similarity	NPC315394
0.7805	Intermediate Similarity	NPC84360
0.7802	Intermediate Similarity	NPC53685
0.7802	Intermediate Similarity	NPC105490
0.7802	Intermediate Similarity	NPC470255
0.7802	Intermediate Similarity	NPC57117
0.7802	Intermediate Similarity	NPC191521
0.7791	Intermediate Similarity	NPC96055
0.7778	Intermediate Similarity	NPC477122
0.7778	Intermediate Similarity	NPC177037
0.7778	Intermediate Similarity	NPC472814
0.7766	Intermediate Similarity	NPC474012
0.7766	Intermediate Similarity	NPC476299
0.7765	Intermediate Similarity	NPC471296
0.7753	Intermediate Similarity	NPC50488
0.7753	Intermediate Similarity	NPC20946
0.7753	Intermediate Similarity	NPC474396
0.7753	Intermediate Similarity	NPC314727
0.7753	Intermediate Similarity	NPC5509
0.7753	Intermediate Similarity	NPC246028
0.7753	Intermediate Similarity	NPC174342
0.775	Intermediate Similarity	NPC476490
0.775	Intermediate Similarity	NPC476489
0.7742	Intermediate Similarity	NPC205143
0.7742	Intermediate Similarity	NPC51499
0.7742	Intermediate Similarity	NPC73911
0.7742	Intermediate Similarity	NPC477719
0.7742	Intermediate Similarity	NPC477718
0.7738	Intermediate Similarity	NPC281880
0.7727	Intermediate Similarity	NPC473891
0.7727	Intermediate Similarity	NPC131329
0.7727	Intermediate Similarity	NPC471796
0.7717	Intermediate Similarity	NPC472441
0.7711	Intermediate Similarity	NPC471220
0.7701	Intermediate Similarity	NPC474013
0.7701	Intermediate Similarity	NPC471494
0.7701	Intermediate Similarity	NPC30984
0.7692	Intermediate Similarity	NPC7349
0.7692	Intermediate Similarity	NPC156553
0.7684	Intermediate Similarity	NPC303559
0.7684	Intermediate Similarity	NPC472554
0.7683	Intermediate Similarity	NPC27205
0.7674	Intermediate Similarity	NPC477667
0.7674	Intermediate Similarity	NPC477124
0.7674	Intermediate Similarity	NPC49208
0.7674	Intermediate Similarity	NPC79945
0.7674	Intermediate Similarity	NPC193198
0.7674	Intermediate Similarity	NPC476927
0.7667	Intermediate Similarity	NPC209816
0.7667	Intermediate Similarity	NPC220216
0.766	Intermediate Similarity	NPC278386
0.766	Intermediate Similarity	NPC159763
0.766	Intermediate Similarity	NPC474440
0.766	Intermediate Similarity	NPC278673
0.766	Intermediate Similarity	NPC124512
0.7654	Intermediate Similarity	NPC477204
0.7654	Intermediate Similarity	NPC474280
0.7647	Intermediate Similarity	NPC25554
0.7647	Intermediate Similarity	NPC8538
0.7647	Intermediate Similarity	NPC184208
0.764	Intermediate Similarity	NPC93411
0.7634	Intermediate Similarity	NPC190713
0.7634	Intermediate Similarity	NPC202833
0.7625	Intermediate Similarity	NPC316185
0.7619	Intermediate Similarity	NPC80471
0.7619	Intermediate Similarity	NPC5908
0.7619	Intermediate Similarity	NPC471537
0.7619	Intermediate Similarity	NPC110373
0.7619	Intermediate Similarity	NPC325869
0.7614	Intermediate Similarity	NPC211892
0.7614	Intermediate Similarity	NPC329692
0.7614	Intermediate Similarity	NPC311163
0.7614	Intermediate Similarity	NPC305475
0.7614	Intermediate Similarity	NPC475461
0.7609	Intermediate Similarity	NPC469491
0.7609	Intermediate Similarity	NPC474554
0.7604	Intermediate Similarity	NPC476081
0.7604	Intermediate Similarity	NPC475038
0.7604	Intermediate Similarity	NPC11956
0.7604	Intermediate Similarity	NPC472552
0.7604	Intermediate Similarity	NPC109195
0.7595	Intermediate Similarity	NPC151481
0.7595	Intermediate Similarity	NPC475004
0.759	Intermediate Similarity	NPC40049
0.759	Intermediate Similarity	NPC283619
0.759	Intermediate Similarity	NPC474278
0.7586	Intermediate Similarity	NPC295799
0.7582	Intermediate Similarity	NPC2882
0.7582	Intermediate Similarity	NPC177641
0.7582	Intermediate Similarity	NPC249034
0.7582	Intermediate Similarity	NPC124374
0.7582	Intermediate Similarity	NPC234335
0.7579	Intermediate Similarity	NPC324841
0.7579	Intermediate Similarity	NPC227865
0.7579	Intermediate Similarity	NPC477716
0.7579	Intermediate Similarity	NPC477721

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 NPC475944 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	1618
0.2-0.3	3840
0.3-0.4	2500
0.4-0.5	691
0.5-0.6	280
0.6-0.7	80
0.7-0.8	6
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD6400	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4225	Approved
0.7396	Intermediate Similarity	NPD7640	Approved
0.7396	Intermediate Similarity	NPD7639	Approved
0.7308	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7638	Approved
0.7283	Intermediate Similarity	NPD46	Approved
0.7283	Intermediate Similarity	NPD6698	Approved
0.7283	Intermediate Similarity	NPD5785	Approved
0.7273	Intermediate Similarity	NPD7154	Phase 3
0.7204	Intermediate Similarity	NPD7637	Suspended
0.7179	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD8039	Approved
0.7126	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7838	Discovery
0.6947	Remote Similarity	NPD5779	Approved
0.6947	Remote Similarity	NPD5778	Approved
0.6932	Remote Similarity	NPD4822	Approved
0.6932	Remote Similarity	NPD4821	Approved
0.6932	Remote Similarity	NPD4820	Approved
0.6932	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD4191	Approved
0.6923	Remote Similarity	NPD4192	Approved
0.6923	Remote Similarity	NPD4194	Approved
0.6923	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4193	Approved
0.6897	Remote Similarity	NPD4268	Approved
0.6897	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4271	Approved
0.6893	Remote Similarity	NPD6686	Approved
0.6889	Remote Similarity	NPD6695	Phase 3
0.6889	Remote Similarity	NPD5362	Discontinued
0.6869	Remote Similarity	NPD6648	Approved
0.6852	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD6411	Approved
0.6813	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6051	Approved
0.6804	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8264	Approved
0.6739	Remote Similarity	NPD1694	Approved
0.6739	Remote Similarity	NPD5363	Approved
0.6733	Remote Similarity	NPD7632	Discontinued
0.6703	Remote Similarity	NPD5331	Approved
0.6703	Remote Similarity	NPD5332	Approved
0.6701	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD7515	Phase 2
0.6632	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6101	Approved
0.6629	Remote Similarity	NPD6929	Approved
0.6604	Remote Similarity	NPD6371	Approved
0.6598	Remote Similarity	NPD6399	Phase 3
0.6596	Remote Similarity	NPD7750	Discontinued
0.6596	Remote Similarity	NPD4251	Approved
0.6596	Remote Similarity	NPD7524	Approved
0.6596	Remote Similarity	NPD4250	Approved
0.6593	Remote Similarity	NPD5209	Approved
0.6593	Remote Similarity	NPD4269	Approved
0.6593	Remote Similarity	NPD4270	Approved
0.6591	Remote Similarity	NPD6925	Approved
0.6591	Remote Similarity	NPD5776	Phase 2
0.6566	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7332	Phase 2
0.6556	Remote Similarity	NPD6931	Approved
0.6556	Remote Similarity	NPD7514	Phase 3
0.6556	Remote Similarity	NPD6930	Phase 2
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6517	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7145	Approved
0.6509	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.65	Remote Similarity	NPD368	Approved
0.65	Remote Similarity	NPD7902	Approved
0.6495	Remote Similarity	NPD7983	Approved
0.6489	Remote Similarity	NPD5786	Approved
0.6489	Remote Similarity	NPD7521	Approved
0.6489	Remote Similarity	NPD7334	Approved
0.6489	Remote Similarity	NPD5330	Approved
0.6489	Remote Similarity	NPD6409	Approved
0.6489	Remote Similarity	NPD6684	Approved
0.6489	Remote Similarity	NPD4249	Approved
0.6489	Remote Similarity	NPD7146	Approved
0.6486	Remote Similarity	NPD7327	Approved
0.6486	Remote Similarity	NPD7328	Approved
0.6484	Remote Similarity	NPD6902	Approved
0.6481	Remote Similarity	NPD6053	Discontinued
0.6465	Remote Similarity	NPD5695	Phase 3
0.646	Remote Similarity	NPD8033	Approved
0.6444	Remote Similarity	NPD7645	Phase 2
0.6437	Remote Similarity	NPD6924	Approved
0.6437	Remote Similarity	NPD6926	Approved
0.6429	Remote Similarity	NPD7516	Approved
0.6415	Remote Similarity	NPD6899	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD6881	Approved
0.6413	Remote Similarity	NPD6435	Approved
0.6404	Remote Similarity	NPD4756	Discovery
0.64	Remote Similarity	NPD7839	Suspended
0.6383	Remote Similarity	NPD1696	Phase 3
0.6374	Remote Similarity	NPD4252	Approved
0.6372	Remote Similarity	NPD8294	Approved
0.6372	Remote Similarity	NPD8377	Approved
0.6364	Remote Similarity	NPD7339	Approved
0.6364	Remote Similarity	NPD6942	Approved
0.6355	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD6373	Approved
0.6354	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6672	Approved
0.6354	Remote Similarity	NPD6903	Approved
0.6354	Remote Similarity	NPD5737	Approved
0.6353	Remote Similarity	NPD6922	Approved
0.6353	Remote Similarity	NPD6923	Approved
0.6327	Remote Similarity	NPD7087	Discontinued
0.6321	Remote Similarity	NPD5701	Approved
0.6321	Remote Similarity	NPD5697	Approved
0.6316	Remote Similarity	NPD8380	Approved
0.6316	Remote Similarity	NPD8379	Approved
0.6316	Remote Similarity	NPD8296	Approved
0.6316	Remote Similarity	NPD8335	Approved
0.6316	Remote Similarity	NPD7503	Approved
0.6316	Remote Similarity	NPD8378	Approved
0.6316	Remote Similarity	NPD3618	Phase 1
0.6304	Remote Similarity	NPD5369	Approved
0.6304	Remote Similarity	NPD6898	Phase 1
0.6296	Remote Similarity	NPD7102	Approved
0.6296	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD6883	Approved
0.6296	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6933	Approved
0.6292	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5328	Approved
0.6282	Remote Similarity	NPD4219	Approved
0.6279	Remote Similarity	NPD7143	Approved
0.6279	Remote Similarity	NPD7144	Approved
0.6277	Remote Similarity	NPD3666	Approved
0.6277	Remote Similarity	NPD3133	Approved
0.6277	Remote Similarity	NPD3665	Phase 1
0.6277	Remote Similarity	NPD4786	Approved
0.6275	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD7505	Discontinued
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.6237	Remote Similarity	NPD3667	Approved
0.6222	Remote Similarity	NPD6932	Approved
0.6211	Remote Similarity	NPD6893	Approved
0.6207	Remote Similarity	NPD7152	Approved
0.6207	Remote Similarity	NPD7150	Approved
0.6207	Remote Similarity	NPD7151	Approved
0.6204	Remote Similarity	NPD6014	Approved
0.6204	Remote Similarity	NPD6013	Approved
0.6204	Remote Similarity	NPD6012	Approved
0.62	Remote Similarity	NPD7900	Approved
0.62	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7525	Registered
0.6196	Remote Similarity	NPD5368	Approved
0.619	Remote Similarity	NPD7331	Phase 2
0.6182	Remote Similarity	NPD8297	Approved
0.6182	Remote Similarity	NPD6882	Approved
0.6173	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6079	Approved
0.6162	Remote Similarity	NPD5693	Phase 1
0.6162	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD342	Phase 1
0.6146	Remote Similarity	NPD5279	Phase 3
0.6136	Remote Similarity	NPD4732	Discontinued
0.6122	Remote Similarity	NPD4753	Phase 2
0.6122	Remote Similarity	NPD5370	Suspended
0.6111	Remote Similarity	NPD6011	Approved
0.6102	Remote Similarity	NPD7507	Approved
0.6095	Remote Similarity	NPD5211	Phase 2
0.6091	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6683	Phase 2
0.6082	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6640	Phase 3
0.6075	Remote Similarity	NPD4211	Phase 1
0.6042	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5282	Discontinued
0.6038	Remote Similarity	NPD6647	Phase 2
0.6022	Remote Similarity	NPD7509	Discontinued
0.6022	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD4755	Approved
0.6019	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD6110	Phase 1
0.5981	Remote Similarity	NPD5141	Approved
0.598	Remote Similarity	NPD6356	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