NPASS Compound

Structure

NPC470260 OpenBabel07101718312D 34 36 0 0 1 0 0 0 0 0999 V2000 1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 1.8660 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 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 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 5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8690 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 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 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 14 19 1 0 0 0 0 15 27 2 0 0 0 0 15 31 1 0 0 0 0 16 28 2 0 0 0 0 16 33 1 0 0 0 0 17 29 2 0 0 0 0 17 34 1 0 0 0 0 18 13 1 6 0 0 0 18 22 1 0 0 0 0 19 30 1 6 0 0 0 20 11 1 6 0 0 0 20 23 1 0 0 0 0 20 32 1 0 0 0 0 21 26 1 1 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 26 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.27
Volume:	492.359
LogP:	3.175
LogD:	2.538
LogS:	-3.394
# Rotatable Bonds:	7
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.371
Synthetic Accessibility Score:	6.247
Fsp3:	0.808
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:	-4.863
MDCK Permeability:	6.589463009731844e-05
Pgp-inhibitor:	0.879
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.342

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.322
Plasma Protein Binding (PPB):	53.686279296875%
Volume Distribution (VD):	1.393
Pgp-substrate:	35.643497467041016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.395
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.291
CYP3A4-substrate:	0.442

ADMET: Excretion

Clearance (CL):	3.733
Half-life (T1/2):	0.798

ADMET: Toxicity

hERG Blockers:	0.376
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.881
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.199
Maximum Recommended Daily Dose:	0.137
Skin Sensitization:	0.21
Carcinogencity:	0.138
Eye Corrosion:	0.016
Eye Irritation:	0.026
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC470260

Natural Product ID:	NPC470260
*Common Name:**	Labiatin E
IUPAC Name:	n.a.
Synonyms:	Labiatin E
Standard InCHIKey:	ZRFWYDWQAADALN-LABTTXFKSA-N
Standard InCHI:	InChI=1S/C26H40O8/c1-13(2)18-12-21(31-15(4)27)26(8,34-17(6)29)23-20-11-14(3)19(30)9-10-25(7,33-16(5)28)24(32-20)22(18)23/h13,18-24,30H,3,9-12H2,1-2,4-8H3/t18-,19+,20-,21+,22-,23-,24-,25-,26-/m1/s1
SMILES:	CC(C)C1CC(C(C2C1C3C(CCC(C(=C)CC2O3)O)(C)OC(=O)C)(C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928375
PubChem CID:	21575370
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane 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
NPO32470	octocorallia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[21970540]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	73000.0	nM	PMID[533993]

☑ 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 NPC470260 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	1665
0.2-0.3	5406
0.3-0.4	13909
0.4-0.5	9253
0.5-0.6	7608
0.6-0.7	4280
0.7-0.8	339
0.8-0.85	23
0.85-0.9	11
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC75443
0.9756	High Similarity	NPC475684
0.9647	High Similarity	NPC91251
0.9643	High Similarity	NPC161560
0.9639	High Similarity	NPC44538
0.9529	High Similarity	NPC312471
0.9529	High Similarity	NPC471378
0.9524	High Similarity	NPC476723
0.9524	High Similarity	NPC92370
0.9524	High Similarity	NPC476724
0.9412	High Similarity	NPC291875
0.9398	High Similarity	NPC471379
0.9398	High Similarity	NPC196911
0.939	High Similarity	NPC5958
0.9195	High Similarity	NPC122057
0.9146	High Similarity	NPC77003
0.8977	High Similarity	NPC312805
0.8941	High Similarity	NPC476725
0.8929	High Similarity	NPC127917
0.8916	High Similarity	NPC118116
0.8706	High Similarity	NPC239308
0.8621	High Similarity	NPC322922
0.8621	High Similarity	NPC321812
0.8588	High Similarity	NPC103171
0.8556	High Similarity	NPC8729
0.8511	High Similarity	NPC272223
0.8478	Intermediate Similarity	NPC476720
0.8454	Intermediate Similarity	NPC470263
0.8333	Intermediate Similarity	NPC264610
0.8333	Intermediate Similarity	NPC43463
0.8313	Intermediate Similarity	NPC293223
0.8313	Intermediate Similarity	NPC329626
0.8313	Intermediate Similarity	NPC136424
0.8298	Intermediate Similarity	NPC473244
0.8298	Intermediate Similarity	NPC111348
0.828	Intermediate Similarity	NPC241047
0.8256	Intermediate Similarity	NPC211049
0.8222	Intermediate Similarity	NPC309656
0.8202	Intermediate Similarity	NPC214315
0.8193	Intermediate Similarity	NPC36479
0.8191	Intermediate Similarity	NPC306797
0.8191	Intermediate Similarity	NPC292718
0.8191	Intermediate Similarity	NPC169270
0.8191	Intermediate Similarity	NPC111834
0.8152	Intermediate Similarity	NPC208839
0.814	Intermediate Similarity	NPC186594
0.8118	Intermediate Similarity	NPC252483
0.8118	Intermediate Similarity	NPC191345
0.8046	Intermediate Similarity	NPC116320
0.8046	Intermediate Similarity	NPC119922
0.8	Intermediate Similarity	NPC284194
0.8	Intermediate Similarity	NPC471765
0.8	Intermediate Similarity	NPC211810
0.8	Intermediate Similarity	NPC221801
0.8	Intermediate Similarity	NPC476719
0.798	Intermediate Similarity	NPC473543
0.7979	Intermediate Similarity	NPC472360
0.7979	Intermediate Similarity	NPC472416
0.7957	Intermediate Similarity	NPC41838
0.7957	Intermediate Similarity	NPC165180
0.7957	Intermediate Similarity	NPC219516
0.7955	Intermediate Similarity	NPC216800
0.7938	Intermediate Similarity	NPC188968
0.7917	Intermediate Similarity	NPC472998
0.7917	Intermediate Similarity	NPC274793
0.7895	Intermediate Similarity	NPC292178
0.7895	Intermediate Similarity	NPC86893
0.7889	Intermediate Similarity	NPC164424
0.7879	Intermediate Similarity	NPC471467
0.7879	Intermediate Similarity	NPC61442
0.7879	Intermediate Similarity	NPC473523
0.7872	Intermediate Similarity	NPC26046
0.7857	Intermediate Similarity	NPC144486
0.7857	Intermediate Similarity	NPC472554
0.7857	Intermediate Similarity	NPC49532
0.7849	Intermediate Similarity	NPC194485
0.7849	Intermediate Similarity	NPC53890
0.7849	Intermediate Similarity	NPC153853
0.7849	Intermediate Similarity	NPC219937
0.7849	Intermediate Similarity	NPC123252
0.7835	Intermediate Similarity	NPC469725
0.7826	Intermediate Similarity	NPC160304
0.7812	Intermediate Similarity	NPC472995
0.7802	Intermediate Similarity	NPC279260
0.7789	Intermediate Similarity	NPC476722
0.7778	Intermediate Similarity	NPC472552
0.7778	Intermediate Similarity	NPC299963
0.7778	Intermediate Similarity	NPC476471
0.7778	Intermediate Similarity	NPC470972
0.7778	Intermediate Similarity	NPC31085
0.7778	Intermediate Similarity	NPC475344
0.7755	Intermediate Similarity	NPC38855
0.7755	Intermediate Similarity	NPC475877
0.7753	Intermediate Similarity	NPC477446
0.7753	Intermediate Similarity	NPC477447
0.7753	Intermediate Similarity	NPC470155
0.7742	Intermediate Similarity	NPC246028
0.7742	Intermediate Similarity	NPC194642
0.7738	Intermediate Similarity	NPC476718
0.7732	Intermediate Similarity	NPC254121
0.7732	Intermediate Similarity	NPC120446
0.7717	Intermediate Similarity	NPC471377
0.7708	Intermediate Similarity	NPC469583
0.77	Intermediate Similarity	NPC475623
0.77	Intermediate Similarity	NPC475334
0.77	Intermediate Similarity	NPC473694
0.77	Intermediate Similarity	NPC474124
0.7692	Intermediate Similarity	NPC93616
0.7692	Intermediate Similarity	NPC157476
0.7684	Intermediate Similarity	NPC147272
0.7677	Intermediate Similarity	NPC475617
0.7677	Intermediate Similarity	NPC98225
0.766	Intermediate Similarity	NPC10274
0.766	Intermediate Similarity	NPC220216
0.766	Intermediate Similarity	NPC48732
0.7647	Intermediate Similarity	NPC470170
0.7647	Intermediate Similarity	NPC471205
0.7647	Intermediate Similarity	NPC470169
0.764	Intermediate Similarity	NPC470154
0.764	Intermediate Similarity	NPC470156
0.7629	Intermediate Similarity	NPC472996
0.7629	Intermediate Similarity	NPC284518
0.7629	Intermediate Similarity	NPC129569
0.7629	Intermediate Similarity	NPC475304
0.7629	Intermediate Similarity	NPC256227
0.7629	Intermediate Similarity	NPC472997
0.7624	Intermediate Similarity	NPC181104
0.7624	Intermediate Similarity	NPC288502
0.7624	Intermediate Similarity	NPC121518
0.7624	Intermediate Similarity	NPC103298
0.7624	Intermediate Similarity	NPC475331
0.7624	Intermediate Similarity	NPC80809
0.7624	Intermediate Similarity	NPC475335
0.7624	Intermediate Similarity	NPC201144
0.7609	Intermediate Similarity	NPC228593
0.7609	Intermediate Similarity	NPC235196
0.7609	Intermediate Similarity	NPC246347
0.7604	Intermediate Similarity	NPC476716
0.7604	Intermediate Similarity	NPC182826
0.7604	Intermediate Similarity	NPC178949
0.7604	Intermediate Similarity	NPC105375
0.7604	Intermediate Similarity	NPC96736
0.7604	Intermediate Similarity	NPC3359
0.7604	Intermediate Similarity	NPC39453
0.76	Intermediate Similarity	NPC177701
0.76	Intermediate Similarity	NPC165578
0.7582	Intermediate Similarity	NPC102048
0.7579	Intermediate Similarity	NPC124374
0.7579	Intermediate Similarity	NPC473675
0.7579	Intermediate Similarity	NPC130840
0.7576	Intermediate Similarity	NPC79303
0.7573	Intermediate Similarity	NPC217921
0.7573	Intermediate Similarity	NPC38948
0.7573	Intermediate Similarity	NPC128795
0.7573	Intermediate Similarity	NPC135015
0.7573	Intermediate Similarity	NPC48548
0.7556	Intermediate Similarity	NPC472504
0.7553	Intermediate Similarity	NPC261320
0.7551	Intermediate Similarity	NPC474395
0.7551	Intermediate Similarity	NPC473963
0.7551	Intermediate Similarity	NPC475033
0.7551	Intermediate Similarity	NPC475032
0.7549	Intermediate Similarity	NPC60315
0.7549	Intermediate Similarity	NPC470980
0.7549	Intermediate Similarity	NPC165405
0.7549	Intermediate Similarity	NPC470767
0.7549	Intermediate Similarity	NPC470763
0.7528	Intermediate Similarity	NPC472943
0.7528	Intermediate Similarity	NPC472951
0.7527	Intermediate Similarity	NPC166857
0.7526	Intermediate Similarity	NPC259042
0.7526	Intermediate Similarity	NPC276110
0.7526	Intermediate Similarity	NPC157686
0.7525	Intermediate Similarity	NPC72842
0.7525	Intermediate Similarity	NPC99510
0.7525	Intermediate Similarity	NPC474575
0.7524	Intermediate Similarity	NPC17791
0.75	Intermediate Similarity	NPC476132
0.75	Intermediate Similarity	NPC473570
0.75	Intermediate Similarity	NPC206618
0.75	Intermediate Similarity	NPC11974
0.75	Intermediate Similarity	NPC475586
0.75	Intermediate Similarity	NPC52755
0.75	Intermediate Similarity	NPC235920
0.75	Intermediate Similarity	NPC40728
0.75	Intermediate Similarity	NPC96784
0.75	Intermediate Similarity	NPC154906
0.75	Intermediate Similarity	NPC316974
0.75	Intermediate Similarity	NPC308824
0.75	Intermediate Similarity	NPC476715
0.75	Intermediate Similarity	NPC99653
0.7476	Intermediate Similarity	NPC88013
0.7476	Intermediate Similarity	NPC125423
0.7476	Intermediate Similarity	NPC475781
0.7475	Intermediate Similarity	NPC470067
0.7475	Intermediate Similarity	NPC470066
0.7475	Intermediate Similarity	NPC477875
0.7475	Intermediate Similarity	NPC470068
0.7475	Intermediate Similarity	NPC477876
0.7475	Intermediate Similarity	NPC247233

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 NPC470260 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	2295
0.2-0.3	3855
0.3-0.4	1968
0.4-0.5	502
0.5-0.6	291
0.6-0.7	66
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
0.75	Intermediate Similarity	NPD5344	Discontinued
0.7228	Intermediate Similarity	NPD6648	Approved
0.6961	Remote Similarity	NPD4225	Approved
0.6893	Remote Similarity	NPD7639	Approved
0.6893	Remote Similarity	NPD7640	Approved
0.6804	Remote Similarity	NPD7524	Approved
0.6796	Remote Similarity	NPD7638	Approved
0.6759	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8133	Approved
0.6754	Remote Similarity	NPD7516	Approved
0.6705	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6638	Remote Similarity	NPD8033	Approved
0.6636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3168	Discontinued
0.66	Remote Similarity	NPD7838	Discovery
0.66	Remote Similarity	NPD46	Approved
0.66	Remote Similarity	NPD6698	Approved
0.6562	Remote Similarity	NPD6695	Phase 3
0.6552	Remote Similarity	NPD8294	Approved
0.6552	Remote Similarity	NPD8377	Approved
0.6545	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8035	Phase 2
0.6535	Remote Similarity	NPD8034	Phase 2
0.6535	Remote Similarity	NPD7983	Approved
0.6496	Remote Similarity	NPD8335	Approved
0.6496	Remote Similarity	NPD8380	Approved
0.6496	Remote Similarity	NPD8379	Approved
0.6496	Remote Similarity	NPD8378	Approved
0.6496	Remote Similarity	NPD8296	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6465	Remote Similarity	NPD4250	Approved
0.6465	Remote Similarity	NPD4251	Approved
0.6455	Remote Similarity	NPD6686	Approved
0.6449	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7525	Registered
0.6395	Remote Similarity	NPD371	Approved
0.6373	Remote Similarity	NPD7637	Suspended
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4249	Approved
0.6356	Remote Similarity	NPD8513	Phase 3
0.6356	Remote Similarity	NPD8515	Approved
0.6356	Remote Similarity	NPD8517	Approved
0.6356	Remote Similarity	NPD8516	Approved
0.6356	Remote Similarity	NPD7503	Approved
0.6321	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6399	Phase 3
0.63	Remote Similarity	NPD7750	Discontinued
0.6296	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7115	Discovery
0.6283	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7507	Approved
0.6273	Remote Similarity	NPD5739	Approved
0.6273	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD7128	Approved
0.6273	Remote Similarity	NPD6675	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD6931	Approved
0.625	Remote Similarity	NPD6930	Phase 2
0.625	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD4819	Approved
0.6235	Remote Similarity	NPD1145	Discontinued
0.6224	Remote Similarity	NPD3669	Approved
0.6224	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6921	Approved
0.6216	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7492	Approved
0.6174	Remote Similarity	NPD4632	Approved
0.6161	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6154	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6616	Approved
0.6146	Remote Similarity	NPD7645	Phase 2
0.6146	Remote Similarity	NPD6929	Approved
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD6649	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6134	Remote Similarity	NPD6059	Approved
0.6129	Remote Similarity	NPD7319	Approved
0.6126	Remote Similarity	NPD5357	Phase 1
0.6126	Remote Similarity	NPD6008	Approved
0.6098	Remote Similarity	NPD7078	Approved
0.6098	Remote Similarity	NPD8074	Phase 3
0.6098	Remote Similarity	NPD8293	Discontinued
0.6095	Remote Similarity	NPD7748	Approved
0.6087	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD6053	Discontinued
0.6075	Remote Similarity	NPD7902	Approved
0.6071	Remote Similarity	NPD5697	Approved
0.6071	Remote Similarity	NPD6412	Phase 2
0.6071	Remote Similarity	NPD5701	Approved
0.6061	Remote Similarity	NPD7154	Phase 3
0.6058	Remote Similarity	NPD7515	Phase 2
0.6058	Remote Similarity	NPD7087	Discontinued
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6371	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6048	Remote Similarity	NPD7736	Approved
0.6042	Remote Similarity	NPD6114	Approved
0.6042	Remote Similarity	NPD6115	Approved
0.6042	Remote Similarity	NPD4268	Approved
0.6042	Remote Similarity	NPD6697	Approved
0.6042	Remote Similarity	NPD4271	Approved
0.6042	Remote Similarity	NPD6118	Approved
0.6033	Remote Similarity	NPD6370	Approved
0.6019	Remote Similarity	NPD6101	Approved
0.6019	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6847	Approved
0.5984	Remote Similarity	NPD8328	Phase 3
0.5984	Remote Similarity	NPD7604	Phase 2
0.598	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD6012	Approved
0.5965	Remote Similarity	NPD6014	Approved
0.5957	Remote Similarity	NPD1810	Approved
0.5957	Remote Similarity	NPD1811	Approved
0.595	Remote Similarity	NPD5983	Phase 2
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD6015	Approved
0.5941	Remote Similarity	NPD6893	Approved
0.5938	Remote Similarity	NPD5776	Phase 2
0.5938	Remote Similarity	NPD6116	Phase 1
0.5938	Remote Similarity	NPD6925	Approved
0.5926	Remote Similarity	NPD6084	Phase 2
0.5926	Remote Similarity	NPD6083	Phase 2
0.5918	Remote Similarity	NPD7332	Phase 2
0.5918	Remote Similarity	NPD7514	Phase 3
0.5909	Remote Similarity	NPD1700	Approved
0.5905	Remote Similarity	NPD6411	Approved
0.5902	Remote Similarity	NPD5988	Approved
0.59	Remote Similarity	NPD5362	Discontinued
0.5895	Remote Similarity	NPD7339	Approved
0.5895	Remote Similarity	NPD6942	Approved
0.5887	Remote Similarity	NPD6336	Discontinued
0.5877	Remote Similarity	NPD6011	Approved
0.5876	Remote Similarity	NPD7145	Approved
0.587	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6051	Approved
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6898	Phase 1
0.5856	Remote Similarity	NPD5211	Phase 2
0.5849	Remote Similarity	NPD8171	Discontinued
0.5842	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4786	Approved
0.5833	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6117	Approved
0.5833	Remote Similarity	NPD7839	Suspended
0.5833	Remote Similarity	NPD6933	Approved
0.5833	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.58	Remote Similarity	NPD3667	Approved
0.58	Remote Similarity	NPD6435	Approved
0.5795	Remote Similarity	NPD368	Approved
0.5794	Remote Similarity	NPD5282	Discontinued
0.5794	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7900	Approved
0.5789	Remote Similarity	NPD6926	Approved
0.5789	Remote Similarity	NPD6924	Approved
0.5784	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4755	Approved
0.5773	Remote Similarity	NPD6932	Approved
0.5766	Remote Similarity	NPD4159	Approved
0.5758	Remote Similarity	NPD6928	Phase 2
0.5758	Remote Similarity	NPD7509	Discontinued
0.5752	Remote Similarity	NPD5141	Approved
0.5743	Remote Similarity	NPD5331	Approved
0.5743	Remote Similarity	NPD5332	Approved
0.5741	Remote Similarity	NPD5695	Phase 3
0.5729	Remote Similarity	NPD8264	Approved
0.5728	Remote Similarity	NPD3618	Phase 1
0.5726	Remote Similarity	NPD6067	Discontinued
0.5714	Remote Similarity	NPD1695	Approved
0.5714	Remote Similarity	NPD5328	Approved
0.5701	Remote Similarity	NPD4202	Approved
0.57	Remote Similarity	NPD4790	Discontinued
0.57	Remote Similarity	NPD6902	Approved
0.57	Remote Similarity	NPD5369	Approved
0.5676	Remote Similarity	NPD5285	Approved
0.5676	Remote Similarity	NPD5286	Approved
0.5676	Remote Similarity	NPD4696	Approved
0.5676	Remote Similarity	NPD4700	Approved
0.5669	Remote Similarity	NPD6033	Approved
0.5667	Remote Similarity	NPD6274	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