NPASS Compound

Structure

NPC471379 OpenBabel07101718332D 31 33 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 -2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5963 -0.2579 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 0.6923 -1.8035 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 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 -3.2709 0.5000 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 -2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6453 0.0511 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 1.0000 0.0000 C 0 0 1 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 -0.5878 -0.8090 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 -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 0.5878 -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 2.4373 1.0292 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 -4.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5013 -1.2158 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 -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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 24 1 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 11 23 1 0 0 0 0 13 17 1 0 0 0 0 14 25 2 0 0 0 0 14 29 1 0 0 0 0 15 26 2 0 0 0 0 15 31 1 0 0 0 0 16 12 1 1 0 0 0 16 21 1 0 0 0 0 17 27 1 1 0 0 0 18 11 1 6 0 0 0 18 20 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 6 0 0 0 19 29 1 0 0 0 0 20 13 1 1 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 23 28 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.26
Volume:	451.613
LogP:	2.482
LogD:	2.396
LogS:	-3.071
# Rotatable Bonds:	5
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	6.164
Fsp3:	0.833
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:	-4.792
MDCK Permeability:	8.469864405924454e-05
Pgp-inhibitor:	0.494
Pgp-substrate:	0.741
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.343

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.281
Plasma Protein Binding (PPB):	55.89106750488281%
Volume Distribution (VD):	1.233
Pgp-substrate:	34.57728576660156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.669
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.306
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	4.155
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.358
Human Hepatotoxicity (H-HT):	0.884
Drug-inuced Liver Injury (DILI):	0.781
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.517
Maximum Recommended Daily Dose:	0.814
Skin Sensitization:	0.159
Carcinogencity:	0.157
Eye Corrosion:	0.017
Eye Irritation:	0.022
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC471379

Natural Product ID:	NPC471379
*Common Name:**	CTJSBYKSXKTLNF-MEUIQICESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CTJSBYKSXKTLNF-MEUIQICESA-N
Standard InCHI:	InChI=1S/C24H38O7/c1-12(2)16-10-17(27)13(3)20-18-11-23(6,28)19(29-14(4)25)8-9-24(7,31-15(5)26)22(30-18)21(16)20/h12,16-22,27-28H,3,8-11H2,1-2,4-7H3/t16-,17-,18+,19-,20+,21+,22+,23-,24+/m0/s1
SMILES:	CC(=O)O[C@]1(C)CC[C@H](OC(=O)C)[C@@](C[C@H]2O[C@@H]1[C@@H]1[C@@H](C[C@@H](C(=C)[C@H]21)O)C(C)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426316
PubChem CID:	73346221
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
NPO16055	Klyxum molle	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22004052]
NPO16055	Klyxum molle	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[24020806]
NPO16055	Klyxum molle	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
IC50	2
Others	2

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	7.33	%	PMID[533187]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[533187]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	14.74	%	PMID[533187]

☑ 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 NPC471379 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	174
0.1-0.2	1597
0.2-0.3	5373
0.3-0.4	14172
0.4-0.5	8888
0.5-0.6	7959
0.6-0.7	4199
0.7-0.8	290
0.8-0.85	12
0.85-0.9	14
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC196911
0.9747	High Similarity	NPC5958
0.963	High Similarity	NPC475684
0.9512	High Similarity	NPC44538
0.9494	High Similarity	NPC77003
0.9494	High Similarity	NPC118116
0.9405	High Similarity	NPC312471
0.9405	High Similarity	NPC471378
0.9398	High Similarity	NPC75443
0.9398	High Similarity	NPC470260
0.9398	High Similarity	NPC476724
0.9398	High Similarity	NPC92370
0.9398	High Similarity	NPC476723
0.9286	High Similarity	NPC161560
0.9286	High Similarity	NPC291875
0.9259	High Similarity	NPC239308
0.9136	High Similarity	NPC103171
0.907	High Similarity	NPC91251
0.907	High Similarity	NPC122057
0.8929	High Similarity	NPC321812
0.8929	High Similarity	NPC322922
0.8861	High Similarity	NPC293223
0.8861	High Similarity	NPC329626
0.8851	High Similarity	NPC312805
0.881	High Similarity	NPC476725
0.8795	High Similarity	NPC127917
0.8734	High Similarity	NPC36479
0.8642	High Similarity	NPC264610
0.8506	High Similarity	NPC309656
0.8427	Intermediate Similarity	NPC8729
0.8427	Intermediate Similarity	NPC208839
0.8395	Intermediate Similarity	NPC136424
0.8352	Intermediate Similarity	NPC476720
0.8193	Intermediate Similarity	NPC252483
0.8193	Intermediate Similarity	NPC191345
0.8193	Intermediate Similarity	NPC43463
0.8191	Intermediate Similarity	NPC272223
0.8172	Intermediate Similarity	NPC111348
0.8144	Intermediate Similarity	NPC470263
0.8072	Intermediate Similarity	NPC476719
0.8068	Intermediate Similarity	NPC214315
0.7979	Intermediate Similarity	NPC473244
0.7957	Intermediate Similarity	NPC86893
0.7957	Intermediate Similarity	NPC292178
0.7907	Intermediate Similarity	NPC211049
0.7872	Intermediate Similarity	NPC306797
0.7872	Intermediate Similarity	NPC292718
0.7872	Intermediate Similarity	NPC111834
0.7872	Intermediate Similarity	NPC169270
0.7841	Intermediate Similarity	NPC102048
0.7826	Intermediate Similarity	NPC219516
0.7826	Intermediate Similarity	NPC165180
0.7812	Intermediate Similarity	NPC38855
0.7791	Intermediate Similarity	NPC186594
0.7789	Intermediate Similarity	NPC254121
0.7789	Intermediate Similarity	NPC120446
0.7766	Intermediate Similarity	NPC241047
0.7753	Intermediate Similarity	NPC164424
0.7742	Intermediate Similarity	NPC26046
0.7732	Intermediate Similarity	NPC144486
0.7717	Intermediate Similarity	NPC153853
0.7717	Intermediate Similarity	NPC53890
0.7717	Intermediate Similarity	NPC123252
0.7717	Intermediate Similarity	NPC48732
0.7717	Intermediate Similarity	NPC220216
0.7717	Intermediate Similarity	NPC194485
0.7717	Intermediate Similarity	NPC219937
0.7708	Intermediate Similarity	NPC469725
0.7701	Intermediate Similarity	NPC119922
0.7701	Intermediate Similarity	NPC116320
0.7692	Intermediate Similarity	NPC160304
0.7684	Intermediate Similarity	NPC284194
0.7684	Intermediate Similarity	NPC211810
0.7684	Intermediate Similarity	NPC471765
0.7684	Intermediate Similarity	NPC221801
0.766	Intermediate Similarity	NPC472360
0.766	Intermediate Similarity	NPC96736
0.766	Intermediate Similarity	NPC178949
0.766	Intermediate Similarity	NPC39453
0.766	Intermediate Similarity	NPC472416
0.766	Intermediate Similarity	NPC476722
0.7653	Intermediate Similarity	NPC470972
0.7653	Intermediate Similarity	NPC31085
0.764	Intermediate Similarity	NPC151176
0.764	Intermediate Similarity	NPC475963
0.764	Intermediate Similarity	NPC299963
0.764	Intermediate Similarity	NPC3464
0.7634	Intermediate Similarity	NPC41838
0.7634	Intermediate Similarity	NPC124374
0.7634	Intermediate Similarity	NPC471747
0.7629	Intermediate Similarity	NPC475877
0.7629	Intermediate Similarity	NPC188968
0.7624	Intermediate Similarity	NPC38948
0.7619	Intermediate Similarity	NPC12696
0.7614	Intermediate Similarity	NPC216800
0.7609	Intermediate Similarity	NPC77001
0.7609	Intermediate Similarity	NPC246028
0.7609	Intermediate Similarity	NPC253618
0.7609	Intermediate Similarity	NPC261320
0.7609	Intermediate Similarity	NPC194642
0.7604	Intermediate Similarity	NPC472998
0.7604	Intermediate Similarity	NPC274793
0.759	Intermediate Similarity	NPC476718
0.7586	Intermediate Similarity	NPC472951
0.7586	Intermediate Similarity	NPC472943
0.7586	Intermediate Similarity	NPC76054
0.7576	Intermediate Similarity	NPC61442
0.7576	Intermediate Similarity	NPC471467
0.7576	Intermediate Similarity	NPC475334
0.7576	Intermediate Similarity	NPC475623
0.7576	Intermediate Similarity	NPC473694
0.7558	Intermediate Similarity	NPC3852
0.7556	Intermediate Similarity	NPC476715
0.7553	Intermediate Similarity	NPC53555
0.7553	Intermediate Similarity	NPC474835
0.7553	Intermediate Similarity	NPC147272
0.7553	Intermediate Similarity	NPC99653
0.7551	Intermediate Similarity	NPC49532
0.7551	Intermediate Similarity	NPC98225
0.7551	Intermediate Similarity	NPC308824
0.7551	Intermediate Similarity	NPC475617
0.7551	Intermediate Similarity	NPC472554
0.7549	Intermediate Similarity	NPC206618
0.7527	Intermediate Similarity	NPC206614
0.7527	Intermediate Similarity	NPC209816
0.7527	Intermediate Similarity	NPC474323
0.7527	Intermediate Similarity	NPC10274
0.7526	Intermediate Similarity	NPC470067
0.7526	Intermediate Similarity	NPC470068
0.7526	Intermediate Similarity	NPC470066
0.75	Intermediate Similarity	NPC103298
0.75	Intermediate Similarity	NPC263079
0.75	Intermediate Similarity	NPC256227
0.75	Intermediate Similarity	NPC201144
0.75	Intermediate Similarity	NPC121518
0.75	Intermediate Similarity	NPC181104
0.75	Intermediate Similarity	NPC291665
0.75	Intermediate Similarity	NPC475335
0.75	Intermediate Similarity	NPC288502
0.75	Intermediate Similarity	NPC475331
0.75	Intermediate Similarity	NPC472995
0.75	Intermediate Similarity	NPC284518
0.75	Intermediate Similarity	NPC475304
0.75	Intermediate Similarity	NPC473543
0.75	Intermediate Similarity	NPC80809
0.75	Intermediate Similarity	NPC129569
0.7475	Intermediate Similarity	NPC472552
0.7475	Intermediate Similarity	NPC177701
0.7475	Intermediate Similarity	NPC165578
0.7474	Intermediate Similarity	NPC476716
0.7474	Intermediate Similarity	NPC3359
0.7473	Intermediate Similarity	NPC476217
0.7473	Intermediate Similarity	NPC279260
0.7471	Intermediate Similarity	NPC72755
0.7471	Intermediate Similarity	NPC476367
0.7447	Intermediate Similarity	NPC235051
0.7447	Intermediate Similarity	NPC249034
0.7447	Intermediate Similarity	NPC473675
0.7447	Intermediate Similarity	NPC130840
0.7444	Intermediate Similarity	NPC222634
0.7444	Intermediate Similarity	NPC474780
0.7442	Intermediate Similarity	NPC40049
0.7442	Intermediate Similarity	NPC476703
0.7426	Intermediate Similarity	NPC470980
0.7426	Intermediate Similarity	NPC60315
0.7426	Intermediate Similarity	NPC470056
0.7426	Intermediate Similarity	NPC470763
0.7426	Intermediate Similarity	NPC165405
0.7426	Intermediate Similarity	NPC470767
0.7426	Intermediate Similarity	NPC470055
0.7423	Intermediate Similarity	NPC205143
0.7423	Intermediate Similarity	NPC475032
0.7423	Intermediate Similarity	NPC475033
0.7423	Intermediate Similarity	NPC474395
0.7423	Intermediate Similarity	NPC473963
0.7419	Intermediate Similarity	NPC133450
0.7419	Intermediate Similarity	NPC115607
0.7416	Intermediate Similarity	NPC472504
0.7416	Intermediate Similarity	NPC477447
0.7416	Intermediate Similarity	NPC477446
0.7416	Intermediate Similarity	NPC470155
0.7404	Intermediate Similarity	NPC157476
0.74	Intermediate Similarity	NPC69171
0.74	Intermediate Similarity	NPC473523
0.74	Intermediate Similarity	NPC474165
0.74	Intermediate Similarity	NPC72842
0.74	Intermediate Similarity	NPC156681
0.74	Intermediate Similarity	NPC99510
0.74	Intermediate Similarity	NPC474124
0.7396	Intermediate Similarity	NPC276110
0.7396	Intermediate Similarity	NPC469583
0.7396	Intermediate Similarity	NPC157686
0.7396	Intermediate Similarity	NPC286612
0.7396	Intermediate Similarity	NPC259042
0.7396	Intermediate Similarity	NPC230347
0.7396	Intermediate Similarity	NPC275310
0.7391	Intermediate Similarity	NPC245004
0.7391	Intermediate Similarity	NPC471377
0.7391	Intermediate Similarity	NPC471779
0.7391	Intermediate Similarity	NPC166857

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 NPC471379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	2188
0.2-0.3	3909
0.3-0.4	1995
0.4-0.5	528
0.5-0.6	297
0.6-0.7	67
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
0.7551	Intermediate Similarity	NPD5344	Discontinued
0.7172	Intermediate Similarity	NPD4225	Approved
0.71	Intermediate Similarity	NPD6648	Approved
0.7021	Intermediate Similarity	NPD7524	Approved
0.6882	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7838	Discovery
0.6804	Remote Similarity	NPD46	Approved
0.6804	Remote Similarity	NPD6698	Approved
0.6789	Remote Similarity	NPD8133	Approved
0.6774	Remote Similarity	NPD6695	Phase 3
0.6765	Remote Similarity	NPD7640	Approved
0.6765	Remote Similarity	NPD7639	Approved
0.6735	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6686	Approved
0.6574	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7637	Suspended
0.6562	Remote Similarity	NPD4249	Approved
0.6552	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7328	Approved
0.6549	Remote Similarity	NPD7327	Approved
0.6522	Remote Similarity	NPD8033	Approved
0.6495	Remote Similarity	NPD7750	Discontinued
0.6491	Remote Similarity	NPD7516	Approved
0.6465	Remote Similarity	NPD3168	Discontinued
0.6455	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4822	Approved
0.6452	Remote Similarity	NPD6930	Phase 2
0.6452	Remote Similarity	NPD4821	Approved
0.6452	Remote Similarity	NPD6931	Approved
0.6452	Remote Similarity	NPD4819	Approved
0.6452	Remote Similarity	NPD4820	Approved
0.6452	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD8377	Approved
0.6435	Remote Similarity	NPD8294	Approved
0.64	Remote Similarity	NPD8034	Phase 2
0.64	Remote Similarity	NPD8035	Phase 2
0.6389	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8296	Approved
0.6379	Remote Similarity	NPD8380	Approved
0.6379	Remote Similarity	NPD8335	Approved
0.6379	Remote Similarity	NPD8379	Approved
0.6379	Remote Similarity	NPD8378	Approved
0.6364	Remote Similarity	NPD6371	Approved
0.6346	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6929	Approved
0.6337	Remote Similarity	NPD6399	Phase 3
0.6321	Remote Similarity	NPD7632	Discontinued
0.6316	Remote Similarity	NPD7115	Discovery
0.6289	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7525	Registered
0.6273	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD1145	Discontinued
0.625	Remote Similarity	NPD7154	Phase 3
0.6239	Remote Similarity	NPD8516	Approved
0.6239	Remote Similarity	NPD8515	Approved
0.6239	Remote Similarity	NPD6412	Phase 2
0.6239	Remote Similarity	NPD8513	Phase 3
0.6239	Remote Similarity	NPD7503	Approved
0.6239	Remote Similarity	NPD8517	Approved
0.6238	Remote Similarity	NPD7087	Discontinued
0.6237	Remote Similarity	NPD4271	Approved
0.6237	Remote Similarity	NPD4268	Approved
0.6235	Remote Similarity	NPD371	Approved
0.6216	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6101	Approved
0.62	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6933	Approved
0.6195	Remote Similarity	NPD4632	Approved
0.6168	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7507	Approved
0.6154	Remote Similarity	NPD6319	Approved
0.6154	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6402	Approved
0.6147	Remote Similarity	NPD5739	Approved
0.6147	Remote Similarity	NPD7128	Approved
0.6147	Remote Similarity	NPD6675	Approved
0.6129	Remote Similarity	NPD6925	Approved
0.6129	Remote Similarity	NPD5776	Phase 2
0.6122	Remote Similarity	NPD6893	Approved
0.6106	Remote Similarity	NPD8297	Approved
0.6106	Remote Similarity	NPD6053	Discontinued
0.6105	Remote Similarity	NPD7514	Phase 3
0.6105	Remote Similarity	NPD7332	Phase 2
0.6083	Remote Similarity	NPD7492	Approved
0.6082	Remote Similarity	NPD5362	Discontinued
0.6078	Remote Similarity	NPD6411	Approved
0.6064	Remote Similarity	NPD7145	Approved
0.6042	Remote Similarity	NPD6898	Phase 1
0.6036	Remote Similarity	NPD7320	Approved
0.6036	Remote Similarity	NPD6899	Approved
0.6036	Remote Similarity	NPD6881	Approved
0.6034	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6616	Approved
0.602	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6059	Approved
0.6017	Remote Similarity	NPD6054	Approved
0.6016	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD5357	Phase 1
0.6	Remote Similarity	NPD7645	Phase 2
0.5984	Remote Similarity	NPD8074	Phase 3
0.5984	Remote Similarity	NPD8293	Discontinued
0.5984	Remote Similarity	NPD7078	Approved
0.5982	Remote Similarity	NPD6372	Approved
0.5982	Remote Similarity	NPD6373	Approved
0.5979	Remote Similarity	NPD6435	Approved
0.5978	Remote Similarity	NPD6926	Approved
0.5978	Remote Similarity	NPD6924	Approved
0.5966	Remote Similarity	NPD6921	Approved
0.5962	Remote Similarity	NPD7748	Approved
0.5962	Remote Similarity	NPD5282	Discontinued
0.596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6932	Approved
0.5946	Remote Similarity	NPD5701	Approved
0.5946	Remote Similarity	NPD5697	Approved
0.5946	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6083	Phase 2
0.5943	Remote Similarity	NPD7902	Approved
0.5943	Remote Similarity	NPD6084	Phase 2
0.5938	Remote Similarity	NPD7509	Discontinued
0.5935	Remote Similarity	NPD7736	Approved
0.5929	Remote Similarity	NPD7290	Approved
0.5929	Remote Similarity	NPD6883	Approved
0.5929	Remote Similarity	NPD7102	Approved
0.5922	Remote Similarity	NPD7515	Phase 2
0.5918	Remote Similarity	NPD5331	Approved
0.5918	Remote Similarity	NPD3669	Approved
0.5918	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5332	Approved
0.5917	Remote Similarity	NPD6370	Approved
0.5914	Remote Similarity	NPD8264	Approved
0.5914	Remote Similarity	NPD7339	Approved
0.5914	Remote Similarity	NPD6942	Approved
0.5897	Remote Similarity	NPD6009	Approved
0.5895	Remote Similarity	NPD6114	Approved
0.5895	Remote Similarity	NPD6697	Approved
0.5895	Remote Similarity	NPD6118	Approved
0.5895	Remote Similarity	NPD6115	Approved
0.5889	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6051	Approved
0.5882	Remote Similarity	NPD1695	Approved
0.5877	Remote Similarity	NPD6869	Approved
0.5877	Remote Similarity	NPD6650	Approved
0.5877	Remote Similarity	NPD8130	Phase 1
0.5877	Remote Similarity	NPD6847	Approved
0.5877	Remote Similarity	NPD6649	Approved
0.5877	Remote Similarity	NPD6617	Approved
0.5876	Remote Similarity	NPD5369	Approved
0.5876	Remote Similarity	NPD6902	Approved
0.5876	Remote Similarity	NPD4790	Discontinued
0.5868	Remote Similarity	NPD7604	Phase 2
0.5868	Remote Similarity	NPD8328	Phase 3
0.5865	Remote Similarity	NPD8171	Discontinued
0.5859	Remote Similarity	NPD4786	Approved
0.5851	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7839	Suspended
0.5841	Remote Similarity	NPD6014	Approved
0.5841	Remote Similarity	NPD6013	Approved
0.5841	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD5983	Phase 2
0.5833	Remote Similarity	NPD6683	Phase 2
0.5833	Remote Similarity	NPD6015	Approved
0.5833	Remote Similarity	NPD6016	Approved
0.5826	Remote Similarity	NPD6882	Approved
0.5816	Remote Similarity	NPD4269	Approved
0.5816	Remote Similarity	NPD4270	Approved
0.5816	Remote Similarity	NPD3667	Approved
0.5806	Remote Similarity	NPD1810	Approved
0.5806	Remote Similarity	NPD1811	Approved
0.5789	Remote Similarity	NPD6116	Phase 1
0.5785	Remote Similarity	NPD5988	Approved
0.5773	Remote Similarity	NPD6928	Phase 2
0.5773	Remote Similarity	NPD5368	Approved
0.5772	Remote Similarity	NPD6336	Discontinued
0.5758	Remote Similarity	NPD6110	Phase 1
0.5755	Remote Similarity	NPD5695	Phase 3
0.5755	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6011	Approved
0.5743	Remote Similarity	NPD5786	Approved
0.5739	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD6640	Phase 3
0.5684	Remote Similarity	NPD6117	Approved
0.5664	Remote Similarity	NPD6685	Approved
0.566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7900	Approved
0.5657	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6421	Discontinued
0.5652	Remote Similarity	NPD4634	Approved
0.5648	Remote Similarity	NPD4755	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