NPASS Compound

Structure

NPC469840 OpenBabel07101719242D 32 36 0 0 1 0 0 0 0 0999 V2000 2.8300 -0.5782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5791 1.6439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0934 1.5702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1392 -2.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4926 -1.5365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5328 1.5702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7197 0.1618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7197 1.5702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3131 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9394 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5328 0.1618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3131 2.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1231 -2.1207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4604 -1.1794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8138 -0.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7434 0.9872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3857 -0.8001 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.8299 -0.5951 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3395 0.4341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8131 3.1404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7697 -2.8836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0382 1.9428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2364 -1.3258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6101 1.3969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3110 0.1971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 29 1 0 0 0 0 3 4 1 0 0 0 0 3 13 2 0 0 0 0 4 15 2 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 20 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 23 2 0 0 0 0 15 31 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 21 1 0 0 0 0 18 24 2 0 0 0 0 19 25 1 0 0 0 0 19 30 1 0 0 0 0 20 1 1 6 0 0 0 21 29 1 6 0 0 0 21 30 1 0 0 0 0 26 32 1 0 0 0 0 27 32 2 0 0 0 0 28 32 2 0 0 0 0 31 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.06
Volume:	414.309
LogP:	0.866
LogD:	0.515
LogS:	-1.816
# Rotatable Bonds:	3
TPSA:	156.66
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	4.538
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.351
MDCK Permeability:	7.348465260292869e-06
Pgp-inhibitor:	0.03
Pgp-substrate:	0.642
Human Intestinal Absorption (HIA):	0.123
20% Bioavailability (F20%):	0.678
30% Bioavailability (F30%):	0.769

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	96.17839813232422%
Volume Distribution (VD):	0.428
Pgp-substrate:	3.071047782897949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.991
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.602
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.734

ADMET: Excretion

Clearance (CL):	2.214
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.832
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.581
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.805
Carcinogencity:	0.749
Eye Corrosion:	0.003
Eye Irritation:	0.214
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC469840

Natural Product ID:	NPC469840
*Common Name:**	Xestosaprol C Methylacetal
IUPAC Name:	n.a.
Synonyms:	Xestosaprol C Methylacetal
Standard InCHIKey:	VEGXLIPPUQZJQC-AKQSQHNNSA-N
Standard InCHI:	InChI=1S/C21H18O10S/c1-20-6-5-14(23)16-17(20)21(29-2,30-19(16)25)18(24)11-7-9-10(8-12(11)20)15(4-3-13(9)22)31-32(26,27)28/h3-4,7-8,19,22,25H,5-6H2,1-2H3,(H,26,27,28)/t19?,20-,21-/m0/s1
SMILES:	CO[C@@]12OC(C3=C2[C@@](c2c(C1=O)cc1c(O)ccc(c1c2)OS(=O)(=O)O)(C)CCC3=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1214424
PubChem CID:	49863899
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO32714	xestospongia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843588]
NPO32714	xestospongia	Genus	Petrosiidae	Eukaryota	n.a.	South Pacific	n.a.	PMID[20634081]

☑ 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	6

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	2
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	570000.0	nM	PMID[513901]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	42000.0	nM	PMID[513901]
NPT2	Others	Unspecified		IC50	=	6710.0	nM	PMID[513901]
NPT1180	Protein Complex	Protein farnesyltransferase	Homo sapiens	IC50	=	4340.0	nM	PMID[513901]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	>	21000.0	nM	PMID[513901]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	21000.0	nM	PMID[513901]

☑ 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 NPC469840 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	370
0.1-0.2	1598
0.2-0.3	3229
0.3-0.4	8605
0.4-0.5	10943
0.5-0.6	6308
0.6-0.7	9969
0.7-0.8	1671
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8526	High Similarity	NPC478160
0.8397	Intermediate Similarity	NPC478164
0.8187	Intermediate Similarity	NPC478163
0.8182	Intermediate Similarity	NPC67197
0.8165	Intermediate Similarity	NPC100242
0.8121	Intermediate Similarity	NPC283480
0.8121	Intermediate Similarity	NPC148323
0.8107	Intermediate Similarity	NPC470735
0.8107	Intermediate Similarity	NPC329647
0.8072	Intermediate Similarity	NPC208651
0.8072	Intermediate Similarity	NPC206641
0.8061	Intermediate Similarity	NPC3898
0.8061	Intermediate Similarity	NPC192219
0.8061	Intermediate Similarity	NPC82190
0.8061	Intermediate Similarity	NPC174599
0.8061	Intermediate Similarity	NPC478159
0.8061	Intermediate Similarity	NPC478161
0.8024	Intermediate Similarity	NPC53139
0.8023	Intermediate Similarity	NPC478021
0.8023	Intermediate Similarity	NPC470580
0.8012	Intermediate Similarity	NPC473945
0.8	Intermediate Similarity	NPC205172
0.8	Intermediate Similarity	NPC209393
0.8	Intermediate Similarity	NPC478020
0.8	Intermediate Similarity	NPC478022
0.7988	Intermediate Similarity	NPC97637
0.7988	Intermediate Similarity	NPC187934
0.7977	Intermediate Similarity	NPC294501
0.7965	Intermediate Similarity	NPC264063
0.7965	Intermediate Similarity	NPC175477
0.7965	Intermediate Similarity	NPC469486
0.7952	Intermediate Similarity	NPC3449
0.7931	Intermediate Similarity	NPC229051
0.7898	Intermediate Similarity	NPC47191
0.7886	Intermediate Similarity	NPC470583
0.7886	Intermediate Similarity	NPC470667
0.7886	Intermediate Similarity	NPC19056
0.7875	Intermediate Similarity	NPC308572
0.7874	Intermediate Similarity	NPC270027
0.7874	Intermediate Similarity	NPC183441
0.7871	Intermediate Similarity	NPC78307
0.787	Intermediate Similarity	NPC284495
0.7866	Intermediate Similarity	NPC116292
0.7866	Intermediate Similarity	NPC267469
0.7866	Intermediate Similarity	NPC179128
0.7866	Intermediate Similarity	NPC87630
0.7857	Intermediate Similarity	NPC471851
0.7853	Intermediate Similarity	NPC472135
0.7844	Intermediate Similarity	NPC66029
0.7844	Intermediate Similarity	NPC472835
0.7841	Intermediate Similarity	NPC102053
0.7834	Intermediate Similarity	NPC475549
0.7834	Intermediate Similarity	NPC155211
0.7829	Intermediate Similarity	NPC131862
0.7821	Intermediate Similarity	NPC202225
0.7797	Intermediate Similarity	NPC470581
0.7797	Intermediate Similarity	NPC266513
0.7797	Intermediate Similarity	NPC115447
0.7797	Intermediate Similarity	NPC470582
0.7791	Intermediate Similarity	NPC472134
0.7791	Intermediate Similarity	NPC147250
0.7785	Intermediate Similarity	NPC475957
0.7784	Intermediate Similarity	NPC474824
0.7784	Intermediate Similarity	NPC182921
0.7784	Intermediate Similarity	NPC218870
0.7784	Intermediate Similarity	NPC186800
0.7784	Intermediate Similarity	NPC70862
0.7784	Intermediate Similarity	NPC470408
0.7778	Intermediate Similarity	NPC146837
0.7778	Intermediate Similarity	NPC278329
0.7778	Intermediate Similarity	NPC212099
0.7778	Intermediate Similarity	NPC101116
0.7778	Intermediate Similarity	NPC216752
0.7771	Intermediate Similarity	NPC478002
0.7765	Intermediate Similarity	NPC470332
0.7764	Intermediate Similarity	NPC201297
0.7764	Intermediate Similarity	NPC474300
0.7758	Intermediate Similarity	NPC35160
0.7758	Intermediate Similarity	NPC162569
0.7756	Intermediate Similarity	NPC52407
0.7753	Intermediate Similarity	NPC72783
0.7753	Intermediate Similarity	NPC187441
0.7753	Intermediate Similarity	NPC283980
0.7753	Intermediate Similarity	NPC58538
0.7747	Intermediate Similarity	NPC314672
0.7746	Intermediate Similarity	NPC469419
0.7744	Intermediate Similarity	NPC5568
0.7744	Intermediate Similarity	NPC119767
0.7744	Intermediate Similarity	NPC478018
0.774	Intermediate Similarity	NPC176246
0.773	Intermediate Similarity	NPC170055
0.773	Intermediate Similarity	NPC208293
0.773	Intermediate Similarity	NPC475923
0.7727	Intermediate Similarity	NPC276238
0.7727	Intermediate Similarity	NPC470336
0.7727	Intermediate Similarity	NPC203751
0.7727	Intermediate Similarity	NPC199357
0.7727	Intermediate Similarity	NPC65118
0.7727	Intermediate Similarity	NPC470335
0.7727	Intermediate Similarity	NPC85368
0.7727	Intermediate Similarity	NPC171460
0.7722	Intermediate Similarity	NPC474311
0.7716	Intermediate Similarity	NPC476473
0.7716	Intermediate Similarity	NPC469885
0.7712	Intermediate Similarity	NPC471530
0.7711	Intermediate Similarity	NPC315520
0.7707	Intermediate Similarity	NPC50924
0.7707	Intermediate Similarity	NPC23894
0.7697	Intermediate Similarity	NPC83331
0.7697	Intermediate Similarity	NPC470334
0.7697	Intermediate Similarity	NPC478000
0.7692	Intermediate Similarity	NPC205721
0.7692	Intermediate Similarity	NPC469507
0.7692	Intermediate Similarity	NPC474861
0.7688	Intermediate Similarity	NPC178281
0.7683	Intermediate Similarity	NPC300540
0.7683	Intermediate Similarity	NPC285122
0.7677	Intermediate Similarity	NPC136588
0.7677	Intermediate Similarity	NPC27659
0.7677	Intermediate Similarity	NPC199253
0.7673	Intermediate Similarity	NPC245923
0.7673	Intermediate Similarity	NPC186647
0.7673	Intermediate Similarity	NPC305060
0.767	Intermediate Similarity	NPC111536
0.767	Intermediate Similarity	NPC271385
0.767	Intermediate Similarity	NPC76128
0.767	Intermediate Similarity	NPC30432
0.767	Intermediate Similarity	NPC5029
0.7669	Intermediate Similarity	NPC300684
0.7669	Intermediate Similarity	NPC218866
0.7669	Intermediate Similarity	NPC84568
0.7669	Intermediate Similarity	NPC48130
0.7669	Intermediate Similarity	NPC79627
0.7667	Intermediate Similarity	NPC478001
0.7665	Intermediate Similarity	NPC472838
0.7665	Intermediate Similarity	NPC306011
0.7662	Intermediate Similarity	NPC48248
0.7662	Intermediate Similarity	NPC96024
0.7658	Intermediate Similarity	NPC283088
0.7657	Intermediate Similarity	NPC473095
0.7657	Intermediate Similarity	NPC259905
0.7657	Intermediate Similarity	NPC473096
0.7657	Intermediate Similarity	NPC246274
0.7654	Intermediate Similarity	NPC153578
0.7654	Intermediate Similarity	NPC277710
0.7654	Intermediate Similarity	NPC469520
0.7654	Intermediate Similarity	NPC299149
0.7654	Intermediate Similarity	NPC114257
0.7654	Intermediate Similarity	NPC69755
0.7651	Intermediate Similarity	NPC478219
0.7651	Intermediate Similarity	NPC474310
0.7651	Intermediate Similarity	NPC247219
0.7647	Intermediate Similarity	NPC254492
0.7647	Intermediate Similarity	NPC29552
0.7647	Intermediate Similarity	NPC71610
0.7644	Intermediate Similarity	NPC178851
0.7643	Intermediate Similarity	NPC225051
0.764	Intermediate Similarity	NPC475233
0.764	Intermediate Similarity	NPC289876
0.764	Intermediate Similarity	NPC475246
0.7633	Intermediate Similarity	NPC478133
0.7633	Intermediate Similarity	NPC474501
0.7628	Intermediate Similarity	NPC85342
0.7627	Intermediate Similarity	NPC470333
0.7627	Intermediate Similarity	NPC98776
0.7625	Intermediate Similarity	NPC173980
0.7625	Intermediate Similarity	NPC475104
0.7624	Intermediate Similarity	NPC292706
0.7624	Intermediate Similarity	NPC224557
0.7622	Intermediate Similarity	NPC474630
0.7622	Intermediate Similarity	NPC474309
0.7622	Intermediate Similarity	NPC478019
0.7619	Intermediate Similarity	NPC474533
0.7619	Intermediate Similarity	NPC474534
0.7616	Intermediate Similarity	NPC477627
0.7614	Intermediate Similarity	NPC298778
0.7613	Intermediate Similarity	NPC131684
0.7611	Intermediate Similarity	NPC315221
0.761	Intermediate Similarity	NPC474813
0.761	Intermediate Similarity	NPC472308
0.761	Intermediate Similarity	NPC471670
0.7607	Intermediate Similarity	NPC143898
0.7607	Intermediate Similarity	NPC66593
0.7605	Intermediate Similarity	NPC205766
0.7605	Intermediate Similarity	NPC477914
0.7602	Intermediate Similarity	NPC228654
0.7602	Intermediate Similarity	NPC324736
0.7602	Intermediate Similarity	NPC314795
0.76	Intermediate Similarity	NPC63470
0.76	Intermediate Similarity	NPC473094
0.7597	Intermediate Similarity	NPC72667
0.7597	Intermediate Similarity	NPC78364
0.7597	Intermediate Similarity	NPC84672
0.7597	Intermediate Similarity	NPC69424
0.7597	Intermediate Similarity	NPC176130
0.7595	Intermediate Similarity	NPC12070
0.7593	Intermediate Similarity	NPC477595
0.7593	Intermediate Similarity	NPC124365
0.7593	Intermediate Similarity	NPC110810
0.759	Intermediate Similarity	NPC470479

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 NPC469840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	961
0.2-0.3	1611
0.3-0.4	2838
0.4-0.5	2153
0.5-0.6	941
0.6-0.7	285
0.7-0.8	39
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
0.7833	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6535	Approved
0.7554	Intermediate Similarity	NPD6534	Approved
0.7545	Intermediate Similarity	NPD7458	Discontinued
0.7447	Intermediate Similarity	NPD6780	Approved
0.7447	Intermediate Similarity	NPD6778	Approved
0.7447	Intermediate Similarity	NPD6776	Approved
0.7447	Intermediate Similarity	NPD6782	Approved
0.7447	Intermediate Similarity	NPD6781	Approved
0.7447	Intermediate Similarity	NPD6777	Approved
0.7447	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD7699	Phase 2
0.7433	Intermediate Similarity	NPD7700	Phase 2
0.7432	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7435	Discontinued
0.7349	Intermediate Similarity	NPD7390	Discontinued
0.7344	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7697	Approved
0.733	Intermediate Similarity	NPD7696	Phase 3
0.733	Intermediate Similarity	NPD7698	Approved
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.7314	Intermediate Similarity	NPD6959	Discontinued
0.7312	Intermediate Similarity	NPD6212	Phase 3
0.7312	Intermediate Similarity	NPD6213	Phase 3
0.7312	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7871	Phase 2
0.7292	Intermediate Similarity	NPD7870	Phase 2
0.7278	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7003	Approved
0.7263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8312	Approved
0.7253	Intermediate Similarity	NPD8313	Approved
0.7239	Intermediate Similarity	NPD5404	Approved
0.7239	Intermediate Similarity	NPD2935	Discontinued
0.7239	Intermediate Similarity	NPD5405	Approved
0.7239	Intermediate Similarity	NPD5406	Approved
0.7239	Intermediate Similarity	NPD5408	Approved
0.7238	Intermediate Similarity	NPD6559	Discontinued
0.7235	Intermediate Similarity	NPD3226	Approved
0.7207	Intermediate Similarity	NPD7799	Discontinued
0.7202	Intermediate Similarity	NPD8320	Phase 1
0.7202	Intermediate Similarity	NPD8319	Approved
0.7195	Intermediate Similarity	NPD2346	Discontinued
0.7194	Intermediate Similarity	NPD7874	Approved
0.7194	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7236	Approved
0.7179	Intermediate Similarity	NPD7701	Phase 2
0.7178	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7239	Suspended
0.7167	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1470	Approved
0.7111	Intermediate Similarity	NPD3751	Discontinued
0.7104	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1201	Approved
0.7088	Intermediate Similarity	NPD6797	Phase 2
0.7086	Intermediate Similarity	NPD7058	Phase 2
0.7086	Intermediate Similarity	NPD7057	Phase 3
0.7079	Intermediate Similarity	NPD6232	Discontinued
0.7071	Intermediate Similarity	NPD7801	Approved
0.7069	Intermediate Similarity	NPD7819	Suspended
0.7066	Intermediate Similarity	NPD8166	Discontinued
0.7059	Intermediate Similarity	NPD6273	Approved
0.7056	Intermediate Similarity	NPD7473	Discontinued
0.7049	Intermediate Similarity	NPD7251	Discontinued
0.7017	Intermediate Similarity	NPD3818	Discontinued
0.7011	Intermediate Similarity	NPD7808	Phase 3
0.701	Intermediate Similarity	NPD6823	Phase 2
0.7	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4380	Phase 2
0.6982	Remote Similarity	NPD3300	Phase 2
0.6968	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7075	Discontinued
0.694	Remote Similarity	NPD7074	Phase 3
0.6923	Remote Similarity	NPD3023	Approved
0.6923	Remote Similarity	NPD3026	Approved
0.6914	Remote Similarity	NPD6801	Discontinued
0.6905	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2532	Approved
0.6901	Remote Similarity	NPD2534	Approved
0.6901	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2533	Approved
0.6898	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6599	Discontinued
0.6889	Remote Similarity	NPD3787	Discontinued
0.6885	Remote Similarity	NPD7054	Approved
0.6875	Remote Similarity	NPD2798	Approved
0.6864	Remote Similarity	NPD4628	Phase 3
0.6862	Remote Similarity	NPD8434	Phase 2
0.6859	Remote Similarity	NPD2932	Approved
0.6859	Remote Similarity	NPD3019	Approved
0.6857	Remote Similarity	NPD7411	Suspended
0.6852	Remote Similarity	NPD7008	Discontinued
0.6848	Remote Similarity	NPD7472	Approved
0.6845	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD5402	Approved
0.6836	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6190	Approved
0.6816	Remote Similarity	NPD7783	Phase 2
0.6816	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6166	Phase 2
0.6813	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3764	Approved
0.6802	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8151	Discontinued
0.6795	Remote Similarity	NPD3024	Approved
0.6795	Remote Similarity	NPD3025	Approved
0.6786	Remote Similarity	NPD1471	Phase 3
0.6786	Remote Similarity	NPD2344	Approved
0.678	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6663	Approved
0.6766	Remote Similarity	NPD2799	Discontinued
0.6744	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7177	Discontinued
0.673	Remote Similarity	NPD3972	Approved
0.6728	Remote Similarity	NPD5736	Approved
0.671	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2313	Discontinued
0.6704	Remote Similarity	NPD3882	Suspended
0.6704	Remote Similarity	NPD7768	Phase 2
0.6688	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5951	Approved
0.6685	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1510	Phase 2
0.6648	Remote Similarity	NPD3817	Phase 2
0.6647	Remote Similarity	NPD1607	Approved
0.6646	Remote Similarity	NPD1283	Approved
0.6646	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD37	Approved
0.6628	Remote Similarity	NPD2309	Approved
0.6627	Remote Similarity	NPD2979	Phase 3
0.6627	Remote Similarity	NPD4060	Phase 1
0.6611	Remote Similarity	NPD4966	Approved
0.6611	Remote Similarity	NPD4965	Approved
0.6611	Remote Similarity	NPD4967	Phase 2
0.661	Remote Similarity	NPD7028	Phase 2
0.6608	Remote Similarity	NPD2800	Approved
0.6605	Remote Similarity	NPD1164	Approved
0.6604	Remote Similarity	NPD8059	Phase 3
0.6604	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8368	Discontinued
0.6592	Remote Similarity	NPD8455	Phase 2
0.6592	Remote Similarity	NPD2801	Approved
0.6588	Remote Similarity	NPD7266	Discontinued
0.6588	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1651	Approved
0.6579	Remote Similarity	NPD8407	Phase 2
0.6576	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7228	Approved
0.6558	Remote Similarity	NPD7635	Approved
0.6552	Remote Similarity	NPD6799	Approved
0.655	Remote Similarity	NPD1549	Phase 2
0.655	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3095	Discontinued
0.6538	Remote Similarity	NPD6234	Discontinued
0.6536	Remote Similarity	NPD1934	Approved
0.6536	Remote Similarity	NPD6844	Discontinued
0.6534	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5403	Approved
0.6529	Remote Similarity	NPD2531	Phase 2
0.6528	Remote Similarity	NPD8360	Approved
0.6528	Remote Similarity	NPD8361	Approved
0.6528	Remote Similarity	NPD8435	Approved
0.6527	Remote Similarity	NPD1240	Approved
0.6519	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6765	Approved
0.6508	Remote Similarity	NPD6764	Approved
0.6508	Remote Similarity	NPD7685	Pre-registration
0.6491	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD1512	Approved
0.6474	Remote Similarity	NPD4954	Approved
0.6474	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4955	Approved
0.6474	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5028	Approved
0.6474	Remote Similarity	NPD36	Approved
0.6474	Remote Similarity	NPD5026	Approved
0.6474	Remote Similarity	NPD5034	Approved
0.6471	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD8127	Discontinued
0.6467	Remote Similarity	NPD7199	Phase 2
0.6467	Remote Similarity	NPD7961	Discontinued
0.6467	Remote Similarity	NPD1247	Approved
0.6462	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1281	Approved
0.6455	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6651	Approved
0.6438	Remote Similarity	NPD4626	Approved
0.6436	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2796	Approved
0.6433	Remote Similarity	NPD6099	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