NPASS Compound

Structure

NPC5958 OpenBabel07101718222D 27 29 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 -2.4049 -2.0000 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 0.5000 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 -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 -2.4049 -1.0000 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 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 -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 -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 -0.5000 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 13 2 0 0 0 0 5 14 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 11 1 6 0 0 0 15 20 1 0 0 0 0 16 24 1 6 0 0 0 17 25 1 1 0 0 0 18 9 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 13 1 1 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	100.09
Volume:	118.486
LogP:	1.552
LogD:	1.429
LogS:	-1.244
# Rotatable Bonds:	4
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	2.053
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.346
MDCK Permeability:	2.5495253794360906e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.854
30% Bioavailability (F30%):	0.741

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984
Plasma Protein Binding (PPB):	31.107261657714844%
Volume Distribution (VD):	1.171
Pgp-substrate:	75.61015319824219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.578
CYP1A2-substrate:	0.802
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.632
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.708
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.373
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	7.511
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.556
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.957
Carcinogencity:	0.185
Eye Corrosion:	0.993
Eye Irritation:	0.991
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC5958

Natural Product ID:	NPC5958
*Common Name:**	XIPCRMWPXWHXFY-ZQFPTXTCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XIPCRMWPXWHXFY-ZQFPTXTCSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-11(2)15-10-17(25)13(4)19-18-9-12(3)16(24)7-8-22(6,27-14(5)23)21(26-18)20(15)19/h11,15-21,24-25H,3-4,7-10H2,1-2,5-6H3/t15-,16+,17+,18-,19-,20-,21-,22-/m1/s1
SMILES:	CC(C)[C@H]1C[C@@H](C(=C)[C@@H]2[C@H]3CC(=C)[C@H](CC[C@](C)([C@@H]([C@H]12)O3)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426318
PubChem CID:	73346222
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	=	0.62	%	PMID[520725]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[520725]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	3.2	%	PMID[520725]

☑ 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 NPC5958 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	159
0.1-0.2	1551
0.2-0.3	5450
0.3-0.4	14803
0.4-0.5	8404
0.5-0.6	8259
0.6-0.7	3812
0.7-0.8	220
0.8-0.85	9
0.85-0.9	10
0.9-0.95	14
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC471379
0.9747	High Similarity	NPC196911
0.974	High Similarity	NPC77003
0.9625	High Similarity	NPC475684
0.9506	High Similarity	NPC44538
0.939	High Similarity	NPC75443
0.939	High Similarity	NPC470260
0.939	High Similarity	NPC92370
0.939	High Similarity	NPC476723
0.939	High Similarity	NPC476724
0.9277	High Similarity	NPC161560
0.9277	High Similarity	NPC291875
0.9241	High Similarity	NPC118116
0.9167	High Similarity	NPC312471
0.9167	High Similarity	NPC471378
0.9146	High Similarity	NPC321812
0.9146	High Similarity	NPC322922
0.9125	High Similarity	NPC103171
0.9059	High Similarity	NPC91251
0.9012	High Similarity	NPC239308
0.8861	High Similarity	NPC264610
0.8846	High Similarity	NPC329626
0.8837	High Similarity	NPC122057
0.8795	High Similarity	NPC476725
0.878	High Similarity	NPC127917
0.8621	High Similarity	NPC312805
0.8608	High Similarity	NPC293223
0.8481	Intermediate Similarity	NPC36479
0.8409	Intermediate Similarity	NPC208839
0.8409	Intermediate Similarity	NPC8729
0.8333	Intermediate Similarity	NPC476720
0.8276	Intermediate Similarity	NPC309656
0.8152	Intermediate Similarity	NPC111348
0.8148	Intermediate Similarity	NPC136424
0.8046	Intermediate Similarity	NPC214315
0.8023	Intermediate Similarity	NPC102048
0.7979	Intermediate Similarity	NPC272223
0.7957	Intermediate Similarity	NPC473244
0.7952	Intermediate Similarity	NPC191345
0.7952	Intermediate Similarity	NPC252483
0.7952	Intermediate Similarity	NPC43463
0.7938	Intermediate Similarity	NPC470263
0.7931	Intermediate Similarity	NPC164424
0.7831	Intermediate Similarity	NPC476719
0.7826	Intermediate Similarity	NPC472416
0.7826	Intermediate Similarity	NPC472360
0.7802	Intermediate Similarity	NPC165180
0.7778	Intermediate Similarity	NPC246028
0.7765	Intermediate Similarity	NPC76054
0.7742	Intermediate Similarity	NPC86893
0.7742	Intermediate Similarity	NPC292178
0.7742	Intermediate Similarity	NPC241047
0.7717	Intermediate Similarity	NPC147272
0.7717	Intermediate Similarity	NPC26046
0.7692	Intermediate Similarity	NPC194485
0.7692	Intermediate Similarity	NPC153853
0.7692	Intermediate Similarity	NPC48732
0.7692	Intermediate Similarity	NPC53890
0.7692	Intermediate Similarity	NPC123252
0.7692	Intermediate Similarity	NPC220216
0.7692	Intermediate Similarity	NPC219937
0.7674	Intermediate Similarity	NPC211049
0.7667	Intermediate Similarity	NPC160304
0.7667	Intermediate Similarity	NPC291665
0.7667	Intermediate Similarity	NPC263079
0.766	Intermediate Similarity	NPC306797
0.766	Intermediate Similarity	NPC284194
0.766	Intermediate Similarity	NPC211810
0.766	Intermediate Similarity	NPC471765
0.766	Intermediate Similarity	NPC292718
0.766	Intermediate Similarity	NPC169270
0.766	Intermediate Similarity	NPC111834
0.766	Intermediate Similarity	NPC221801
0.7634	Intermediate Similarity	NPC476722
0.7614	Intermediate Similarity	NPC3464
0.7614	Intermediate Similarity	NPC151176
0.7614	Intermediate Similarity	NPC475963
0.7614	Intermediate Similarity	NPC299963
0.7609	Intermediate Similarity	NPC124374
0.7609	Intermediate Similarity	NPC471747
0.7609	Intermediate Similarity	NPC219516
0.7609	Intermediate Similarity	NPC473675
0.7604	Intermediate Similarity	NPC38855
0.759	Intermediate Similarity	NPC12696
0.7586	Intermediate Similarity	NPC472504
0.7582	Intermediate Similarity	NPC194642
0.7582	Intermediate Similarity	NPC261320
0.7579	Intermediate Similarity	NPC120446
0.7579	Intermediate Similarity	NPC254121
0.7561	Intermediate Similarity	NPC476718
0.7558	Intermediate Similarity	NPC186594
0.7529	Intermediate Similarity	NPC3852
0.7527	Intermediate Similarity	NPC99653
0.7527	Intermediate Similarity	NPC53555
0.7526	Intermediate Similarity	NPC144486
0.75	Intermediate Similarity	NPC10274
0.75	Intermediate Similarity	NPC471370
0.75	Intermediate Similarity	NPC469725
0.75	Intermediate Similarity	NPC471371
0.75	Intermediate Similarity	NPC209816
0.7475	Intermediate Similarity	NPC473543
0.7474	Intermediate Similarity	NPC256227
0.7474	Intermediate Similarity	NPC284518
0.7474	Intermediate Similarity	NPC475304
0.7471	Intermediate Similarity	NPC116320
0.7471	Intermediate Similarity	NPC119922
0.7449	Intermediate Similarity	NPC470972
0.7449	Intermediate Similarity	NPC31085
0.7447	Intermediate Similarity	NPC178949
0.7447	Intermediate Similarity	NPC105490
0.7447	Intermediate Similarity	NPC476716
0.7447	Intermediate Similarity	NPC3359
0.7447	Intermediate Similarity	NPC474922
0.7447	Intermediate Similarity	NPC39453
0.7447	Intermediate Similarity	NPC96736
0.7444	Intermediate Similarity	NPC476217
0.7442	Intermediate Similarity	NPC72755
0.7442	Intermediate Similarity	NPC476367
0.7426	Intermediate Similarity	NPC38948
0.7423	Intermediate Similarity	NPC475877
0.7423	Intermediate Similarity	NPC188968
0.7419	Intermediate Similarity	NPC130840
0.7419	Intermediate Similarity	NPC249034
0.7419	Intermediate Similarity	NPC41838
0.7416	Intermediate Similarity	NPC474780
0.7416	Intermediate Similarity	NPC97505
0.7416	Intermediate Similarity	NPC222634
0.7412	Intermediate Similarity	NPC40049
0.74	Intermediate Similarity	NPC127609
0.74	Intermediate Similarity	NPC470055
0.74	Intermediate Similarity	NPC470056
0.7396	Intermediate Similarity	NPC274793
0.7396	Intermediate Similarity	NPC472998
0.7396	Intermediate Similarity	NPC475032
0.7396	Intermediate Similarity	NPC475033
0.7396	Intermediate Similarity	NPC473963
0.7391	Intermediate Similarity	NPC77001
0.7391	Intermediate Similarity	NPC253618
0.7391	Intermediate Similarity	NPC477917
0.7391	Intermediate Similarity	NPC170633
0.7391	Intermediate Similarity	NPC115607
0.7386	Intermediate Similarity	NPC216800
0.7374	Intermediate Similarity	NPC473694
0.7374	Intermediate Similarity	NPC473523
0.7374	Intermediate Similarity	NPC475623
0.7374	Intermediate Similarity	NPC471467
0.7374	Intermediate Similarity	NPC475334
0.7374	Intermediate Similarity	NPC61442
0.7368	Intermediate Similarity	NPC276110
0.7368	Intermediate Similarity	NPC259042
0.7368	Intermediate Similarity	NPC157686
0.7363	Intermediate Similarity	NPC471779
0.7363	Intermediate Similarity	NPC166857
0.7363	Intermediate Similarity	NPC245004
0.7356	Intermediate Similarity	NPC472951
0.7356	Intermediate Similarity	NPC472943
0.7353	Intermediate Similarity	NPC206618
0.7347	Intermediate Similarity	NPC49532
0.7347	Intermediate Similarity	NPC472554
0.7347	Intermediate Similarity	NPC97435
0.7347	Intermediate Similarity	NPC475617
0.7347	Intermediate Similarity	NPC308824
0.7347	Intermediate Similarity	NPC98225
0.734	Intermediate Similarity	NPC474835
0.734	Intermediate Similarity	NPC7349
0.7333	Intermediate Similarity	NPC290731
0.7333	Intermediate Similarity	NPC476715
0.7333	Intermediate Similarity	NPC35933
0.732	Intermediate Similarity	NPC470066
0.732	Intermediate Similarity	NPC247233
0.732	Intermediate Similarity	NPC470068
0.732	Intermediate Similarity	NPC470067
0.7312	Intermediate Similarity	NPC232202
0.7312	Intermediate Similarity	NPC206614
0.7312	Intermediate Similarity	NPC474323
0.7303	Intermediate Similarity	NPC23748
0.7303	Intermediate Similarity	NPC49208
0.73	Intermediate Similarity	NPC201144
0.73	Intermediate Similarity	NPC121518
0.73	Intermediate Similarity	NPC181104
0.73	Intermediate Similarity	NPC475335
0.73	Intermediate Similarity	NPC103298
0.73	Intermediate Similarity	NPC288502
0.73	Intermediate Similarity	NPC475331
0.73	Intermediate Similarity	NPC80809
0.7292	Intermediate Similarity	NPC54248
0.7292	Intermediate Similarity	NPC93245
0.7292	Intermediate Similarity	NPC276103
0.7292	Intermediate Similarity	NPC472995
0.7292	Intermediate Similarity	NPC129569
0.7292	Intermediate Similarity	NPC473964
0.7283	Intermediate Similarity	NPC58219
0.7283	Intermediate Similarity	NPC48824
0.7283	Intermediate Similarity	NPC177629
0.7283	Intermediate Similarity	NPC254572
0.7283	Intermediate Similarity	NPC250687
0.7283	Intermediate Similarity	NPC229407
0.7273	Intermediate Similarity	NPC475344
0.7273	Intermediate Similarity	NPC472552
0.7273	Intermediate Similarity	NPC165578

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 NPC5958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2128
0.2-0.3	3990
0.3-0.4	2007
0.4-0.5	495
0.5-0.6	313
0.6-0.7	54
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
0.7347	Intermediate Similarity	NPD5344	Discontinued
0.7071	Intermediate Similarity	NPD6648	Approved
0.697	Remote Similarity	NPD4225	Approved
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	Approved
0.6848	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7524	Approved
0.68	Remote Similarity	NPD7638	Approved
0.6739	Remote Similarity	NPD6695	Phase 3
0.6633	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD5779	Approved
0.6632	Remote Similarity	NPD4250	Approved
0.6632	Remote Similarity	NPD4251	Approved
0.6606	Remote Similarity	NPD8133	Approved
0.6598	Remote Similarity	NPD46	Approved
0.6598	Remote Similarity	NPD6698	Approved
0.6598	Remote Similarity	NPD7838	Discovery
0.6531	Remote Similarity	NPD7637	Suspended
0.6531	Remote Similarity	NPD8035	Phase 2
0.6531	Remote Similarity	NPD8034	Phase 2
0.6531	Remote Similarity	NPD7983	Approved
0.6526	Remote Similarity	NPD4249	Approved
0.6471	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6399	Phase 3
0.6458	Remote Similarity	NPD7750	Discontinued
0.6449	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6686	Approved
0.6442	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD3168	Discontinued
0.6421	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1145	Discontinued
0.6413	Remote Similarity	NPD7525	Registered
0.6413	Remote Similarity	NPD4820	Approved
0.6413	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4822	Approved
0.6413	Remote Similarity	NPD4819	Approved
0.6413	Remote Similarity	NPD6930	Phase 2
0.6413	Remote Similarity	NPD4821	Approved
0.6413	Remote Similarity	NPD6931	Approved
0.6389	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7328	Approved
0.6372	Remote Similarity	NPD7327	Approved
0.6348	Remote Similarity	NPD8033	Approved
0.6322	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7516	Approved
0.6304	Remote Similarity	NPD6929	Approved
0.6273	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8377	Approved
0.6261	Remote Similarity	NPD8294	Approved
0.6211	Remote Similarity	NPD5362	Discontinued
0.6211	Remote Similarity	NPD7154	Phase 3
0.6207	Remote Similarity	NPD8378	Approved
0.6207	Remote Similarity	NPD8296	Approved
0.6207	Remote Similarity	NPD8380	Approved
0.6207	Remote Similarity	NPD8335	Approved
0.6207	Remote Similarity	NPD8379	Approved
0.6204	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7087	Discontinued
0.6196	Remote Similarity	NPD4268	Approved
0.6196	Remote Similarity	NPD4271	Approved
0.6182	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6371	Approved
0.6162	Remote Similarity	NPD6101	Approved
0.6162	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4632	Approved
0.6154	Remote Similarity	NPD6933	Approved
0.614	Remote Similarity	NPD7115	Discovery
0.6132	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD6926	Approved
0.6111	Remote Similarity	NPD6924	Approved
0.6111	Remote Similarity	NPD6008	Approved
0.6111	Remote Similarity	NPD7128	Approved
0.6111	Remote Similarity	NPD6402	Approved
0.6111	Remote Similarity	NPD5739	Approved
0.6091	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6925	Approved
0.6087	Remote Similarity	NPD5776	Phase 2
0.6082	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6893	Approved
0.6078	Remote Similarity	NPD7748	Approved
0.6071	Remote Similarity	NPD8297	Approved
0.6071	Remote Similarity	NPD6053	Discontinued
0.6068	Remote Similarity	NPD8516	Approved
0.6068	Remote Similarity	NPD8513	Phase 3
0.6068	Remote Similarity	NPD8515	Approved
0.6068	Remote Similarity	NPD8517	Approved
0.6068	Remote Similarity	NPD7503	Approved
0.6064	Remote Similarity	NPD7332	Phase 2
0.6064	Remote Similarity	NPD7509	Discontinued
0.6064	Remote Similarity	NPD7514	Phase 3
0.6058	Remote Similarity	NPD7902	Approved
0.6055	Remote Similarity	NPD6412	Phase 2
0.605	Remote Similarity	NPD7492	Approved
0.6044	Remote Similarity	NPD8264	Approved
0.6044	Remote Similarity	NPD6942	Approved
0.6044	Remote Similarity	NPD7339	Approved
0.6042	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3669	Approved
0.6042	Remote Similarity	NPD5332	Approved
0.6042	Remote Similarity	NPD5331	Approved
0.604	Remote Similarity	NPD6411	Approved
0.604	Remote Similarity	NPD7515	Phase 2
0.6022	Remote Similarity	NPD6114	Approved
0.6022	Remote Similarity	NPD6115	Approved
0.6022	Remote Similarity	NPD6697	Approved
0.6022	Remote Similarity	NPD7145	Approved
0.6022	Remote Similarity	NPD6118	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD6898	Phase 1
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD371	Approved
0.5983	Remote Similarity	NPD6054	Approved
0.5983	Remote Similarity	NPD6059	Approved
0.5983	Remote Similarity	NPD6319	Approved
0.5979	Remote Similarity	NPD4786	Approved
0.5979	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7604	Phase 2
0.5963	Remote Similarity	NPD5357	Phase 1
0.5957	Remote Similarity	NPD7645	Phase 2
0.595	Remote Similarity	NPD8293	Discontinued
0.595	Remote Similarity	NPD7078	Approved
0.5946	Remote Similarity	NPD6373	Approved
0.5946	Remote Similarity	NPD6372	Approved
0.5938	Remote Similarity	NPD3667	Approved
0.5938	Remote Similarity	NPD6435	Approved
0.5938	Remote Similarity	NPD4270	Approved
0.5938	Remote Similarity	NPD4269	Approved
0.5934	Remote Similarity	NPD1811	Approved
0.5934	Remote Similarity	NPD1810	Approved
0.5932	Remote Similarity	NPD5983	Phase 2
0.5922	Remote Similarity	NPD5282	Discontinued
0.5918	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD6116	Phase 1
0.5914	Remote Similarity	NPD6932	Approved
0.5909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5701	Approved
0.5909	Remote Similarity	NPD5697	Approved
0.5905	Remote Similarity	NPD6084	Phase 2
0.5905	Remote Similarity	NPD6083	Phase 2
0.5902	Remote Similarity	NPD7736	Approved
0.5895	Remote Similarity	NPD6928	Phase 2
0.5893	Remote Similarity	NPD6883	Approved
0.5893	Remote Similarity	NPD7102	Approved
0.5893	Remote Similarity	NPD7290	Approved
0.5882	Remote Similarity	NPD6370	Approved
0.5868	Remote Similarity	NPD6336	Discontinued
0.5862	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5786	Approved
0.5856	Remote Similarity	NPD6011	Approved
0.5854	Remote Similarity	NPD7319	Approved
0.5851	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD1695	Approved
0.5841	Remote Similarity	NPD6847	Approved
0.5841	Remote Similarity	NPD6649	Approved
0.5841	Remote Similarity	NPD6650	Approved
0.5841	Remote Similarity	NPD6869	Approved
0.5841	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6617	Approved
0.5841	Remote Similarity	NPD8130	Phase 1
0.5833	Remote Similarity	NPD6902	Approved
0.582	Remote Similarity	NPD8074	Phase 3
0.581	Remote Similarity	NPD7839	Suspended
0.5806	Remote Similarity	NPD6117	Approved
0.5804	Remote Similarity	NPD6013	Approved
0.5804	Remote Similarity	NPD6012	Approved
0.5804	Remote Similarity	NPD6014	Approved
0.5798	Remote Similarity	NPD6921	Approved
0.5798	Remote Similarity	NPD6015	Approved
0.5798	Remote Similarity	NPD6016	Approved
0.5789	Remote Similarity	NPD6683	Phase 2
0.5789	Remote Similarity	NPD6882	Approved
0.5773	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7900	Approved
0.5765	Remote Similarity	NPD368	Approved
0.5761	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5363	Approved
0.575	Remote Similarity	NPD5988	Approved
0.5729	Remote Similarity	NPD4252	Approved
0.5729	Remote Similarity	NPD4748	Discontinued
0.5729	Remote Similarity	NPD5368	Approved
0.5714	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6110	Phase 1
0.5714	Remote Similarity	NPD4788	Approved
0.5714	Remote Similarity	NPD5695	Phase 3
0.5714	Remote Similarity	NPD7151	Approved
0.5714	Remote Similarity	NPD7150	Approved
0.5714	Remote Similarity	NPD7152	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