NPASS Compound

Structure

NPC476107 OpenBabel07101718322D 22 25 0 0 1 0 0 0 0 0999 V2000 -5.1753 0.2681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5116 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7195 1.8849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -0.4945 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 -0.4330 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 4 1 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 20 1 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 16 2 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 1 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 3 1 6 0 0 0 13 20 1 0 0 0 0 14 15 1 6 0 0 0 14 22 1 0 0 0 0 15 19 1 6 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.07
Volume:	282.12
LogP:	1.436
LogD:	0.784
LogS:	-3.81
# Rotatable Bonds:	0
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	6.365
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.278
MDCK Permeability:	3.9875321817817166e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	30.33296012878418%
Volume Distribution (VD):	0.944
Pgp-substrate:	65.5496597290039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.688
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.495

ADMET: Excretion

Clearance (CL):	3.955
Half-life (T1/2):	0.107

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.443
Drug-inuced Liver Injury (DILI):	0.195
AMES Toxicity:	0.509
Rat Oral Acute Toxicity:	0.496
Maximum Recommended Daily Dose:	0.62
Skin Sensitization:	0.549
Carcinogencity:	0.803
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.254

Download Data

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

Natural Product: NPC476107

Natural Product ID:	NPC476107
*Common Name:**	Malettinin D
IUPAC Name:	n.a.
Synonyms:	Malettinin D
Standard InCHIKey:	NXSJMBWUYLXNQM-PUPMMZHASA-N
Standard InCHI:	InChI=1S/C15H14O7/c1-7-6-20-13(11(7)17)3-4-14-8(2)5-9(16)21-15(14,19)10(13)12(18)22-14/h5-6,10,19H,3-4H2,1-2H3/t10-,13+,14-,15-/m0/s1
SMILES:	CC1=CC(=O)OC2(C13CCC4(C2C(=O)O3)C(=O)C(=CO4)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526826
PubChem CID:	44583904
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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
NPO33490	hypoxylon stromata nrrl 29110	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730245]

☑ 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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.0	mm	PMID[512892]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	14.0	mm	PMID[512892]

☑ 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 NPC476107 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	245
0.1-0.2	1439
0.2-0.3	4215
0.3-0.4	6764
0.4-0.5	11303
0.5-0.6	12255
0.6-0.7	5207
0.7-0.8	1255
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8407	Intermediate Similarity	NPC29827
0.8279	Intermediate Similarity	NPC24651
0.8175	Intermediate Similarity	NPC475139
0.8175	Intermediate Similarity	NPC180902
0.8145	Intermediate Similarity	NPC476008
0.813	Intermediate Similarity	NPC470922
0.8115	Intermediate Similarity	NPC312833
0.8067	Intermediate Similarity	NPC207217
0.8065	Intermediate Similarity	NPC217901
0.8065	Intermediate Similarity	NPC477745
0.8049	Intermediate Similarity	NPC91693
0.8049	Intermediate Similarity	NPC265557
0.8049	Intermediate Similarity	NPC105926
0.8049	Intermediate Similarity	NPC18945
0.8047	Intermediate Similarity	NPC475154
0.8047	Intermediate Similarity	NPC471137
0.8047	Intermediate Similarity	NPC473548
0.8047	Intermediate Similarity	NPC475500
0.8047	Intermediate Similarity	NPC223356
0.8047	Intermediate Similarity	NPC471136
0.8047	Intermediate Similarity	NPC100017
0.8047	Intermediate Similarity	NPC182266
0.8016	Intermediate Similarity	NPC162495
0.8	Intermediate Similarity	NPC477116
0.8	Intermediate Similarity	NPC475273
0.8	Intermediate Similarity	NPC27999
0.8	Intermediate Similarity	NPC168849
0.8	Intermediate Similarity	NPC596
0.7984	Intermediate Similarity	NPC476729
0.7969	Intermediate Similarity	NPC168879
0.7953	Intermediate Similarity	NPC251564
0.7953	Intermediate Similarity	NPC475606
0.7953	Intermediate Similarity	NPC477189
0.7953	Intermediate Similarity	NPC475314
0.7953	Intermediate Similarity	NPC476852
0.7951	Intermediate Similarity	NPC107338
0.7951	Intermediate Similarity	NPC109607
0.7951	Intermediate Similarity	NPC472004
0.7951	Intermediate Similarity	NPC112038
0.7934	Intermediate Similarity	NPC204552
0.7934	Intermediate Similarity	NPC188667
0.7923	Intermediate Similarity	NPC471089
0.7923	Intermediate Similarity	NPC68282
0.7923	Intermediate Similarity	NPC190065
0.7923	Intermediate Similarity	NPC141215
0.792	Intermediate Similarity	NPC225049
0.7917	Intermediate Similarity	NPC478216
0.7917	Intermediate Similarity	NPC471816
0.7917	Intermediate Similarity	NPC270478
0.7903	Intermediate Similarity	NPC473802
0.7903	Intermediate Similarity	NPC67251
0.7899	Intermediate Similarity	NPC478212
0.7899	Intermediate Similarity	NPC477126
0.7891	Intermediate Similarity	NPC473485
0.7891	Intermediate Similarity	NPC474508
0.7886	Intermediate Similarity	NPC102822
0.7886	Intermediate Similarity	NPC470779
0.7886	Intermediate Similarity	NPC477046
0.7874	Intermediate Similarity	NPC476851
0.7869	Intermediate Similarity	NPC469488
0.7869	Intermediate Similarity	NPC268958
0.7869	Intermediate Similarity	NPC470777
0.7869	Intermediate Similarity	NPC475775
0.7869	Intermediate Similarity	NPC476529
0.7863	Intermediate Similarity	NPC140045
0.7863	Intermediate Similarity	NPC38154
0.7863	Intermediate Similarity	NPC295885
0.7851	Intermediate Similarity	NPC122033
0.7851	Intermediate Similarity	NPC287343
0.7851	Intermediate Similarity	NPC13713
0.7851	Intermediate Similarity	NPC53396
0.7851	Intermediate Similarity	NPC474654
0.7851	Intermediate Similarity	NPC478204
0.7851	Intermediate Similarity	NPC469684
0.7851	Intermediate Similarity	NPC58662
0.7851	Intermediate Similarity	NPC470854
0.7851	Intermediate Similarity	NPC98249
0.7851	Intermediate Similarity	NPC97908
0.7846	Intermediate Similarity	NPC262813
0.7845	Intermediate Similarity	NPC474716
0.784	Intermediate Similarity	NPC473919
0.784	Intermediate Similarity	NPC473709
0.7833	Intermediate Similarity	NPC117712
0.7815	Intermediate Similarity	NPC269530
0.7815	Intermediate Similarity	NPC472002
0.7812	Intermediate Similarity	NPC475389
0.7812	Intermediate Similarity	NPC473838
0.7797	Intermediate Similarity	NPC99760
0.7797	Intermediate Similarity	NPC5103
0.7795	Intermediate Similarity	NPC476859
0.7787	Intermediate Similarity	NPC284707
0.7787	Intermediate Similarity	NPC297179
0.7787	Intermediate Similarity	NPC251310
0.7787	Intermediate Similarity	NPC17772
0.7787	Intermediate Similarity	NPC478206
0.7787	Intermediate Similarity	NPC240509
0.7787	Intermediate Similarity	NPC108581
0.7787	Intermediate Similarity	NPC478205
0.7786	Intermediate Similarity	NPC251998
0.7778	Intermediate Similarity	NPC471939
0.7769	Intermediate Similarity	NPC477509
0.776	Intermediate Similarity	NPC472399
0.776	Intermediate Similarity	NPC120724
0.7759	Intermediate Similarity	NPC472645
0.7752	Intermediate Similarity	NPC102316
0.7752	Intermediate Similarity	NPC476193
0.7742	Intermediate Similarity	NPC472000
0.7742	Intermediate Similarity	NPC471999
0.7734	Intermediate Similarity	NPC231529
0.7731	Intermediate Similarity	NPC304180
0.7731	Intermediate Similarity	NPC179798
0.7731	Intermediate Similarity	NPC469656
0.7731	Intermediate Similarity	NPC474846
0.7731	Intermediate Similarity	NPC469655
0.7724	Intermediate Similarity	NPC19028
0.7724	Intermediate Similarity	NPC9674
0.7719	Intermediate Similarity	NPC305085
0.7719	Intermediate Similarity	NPC84042
0.7717	Intermediate Similarity	NPC471940
0.7717	Intermediate Similarity	NPC470780
0.7712	Intermediate Similarity	NPC101018
0.7705	Intermediate Similarity	NPC176513
0.7705	Intermediate Similarity	NPC470775
0.7705	Intermediate Similarity	NPC473590
0.7686	Intermediate Similarity	NPC299849
0.768	Intermediate Similarity	NPC287236
0.768	Intermediate Similarity	NPC170538
0.7674	Intermediate Similarity	NPC476855
0.7674	Intermediate Similarity	NPC476862
0.7674	Intermediate Similarity	NPC476863
0.7672	Intermediate Similarity	NPC296950
0.7672	Intermediate Similarity	NPC146731
0.7672	Intermediate Similarity	NPC258532
0.7661	Intermediate Similarity	NPC317635
0.7661	Intermediate Similarity	NPC478051
0.7661	Intermediate Similarity	NPC329008
0.7656	Intermediate Similarity	NPC476078
0.7656	Intermediate Similarity	NPC270109
0.7656	Intermediate Similarity	NPC476091
0.7652	Intermediate Similarity	NPC58329
0.7647	Intermediate Similarity	NPC474567
0.7647	Intermediate Similarity	NPC478209
0.7647	Intermediate Similarity	NPC253906
0.7647	Intermediate Similarity	NPC472666
0.7647	Intermediate Similarity	NPC235014
0.7642	Intermediate Similarity	NPC470776
0.7638	Intermediate Similarity	NPC473635
0.7638	Intermediate Similarity	NPC181999
0.7638	Intermediate Similarity	NPC293112
0.7634	Intermediate Similarity	NPC471234
0.7632	Intermediate Similarity	NPC469551
0.7627	Intermediate Similarity	NPC192813
0.7627	Intermediate Similarity	NPC277017
0.7627	Intermediate Similarity	NPC154608
0.7623	Intermediate Similarity	NPC138372
0.7623	Intermediate Similarity	NPC251236
0.7623	Intermediate Similarity	NPC106228
0.7623	Intermediate Similarity	NPC152199
0.7623	Intermediate Similarity	NPC328374
0.7623	Intermediate Similarity	NPC134869
0.7623	Intermediate Similarity	NPC179626
0.7623	Intermediate Similarity	NPC190185
0.7623	Intermediate Similarity	NPC40632
0.7623	Intermediate Similarity	NPC96312
0.7623	Intermediate Similarity	NPC235539
0.7623	Intermediate Similarity	NPC213084
0.7619	Intermediate Similarity	NPC471392
0.7619	Intermediate Similarity	NPC11895
0.7619	Intermediate Similarity	NPC469352
0.7603	Intermediate Similarity	NPC7921
0.7603	Intermediate Similarity	NPC469463
0.7603	Intermediate Similarity	NPC51978
0.7603	Intermediate Similarity	NPC208998
0.7603	Intermediate Similarity	NPC471204
0.7603	Intermediate Similarity	NPC33360
0.7603	Intermediate Similarity	NPC94509
0.7603	Intermediate Similarity	NPC470120
0.7603	Intermediate Similarity	NPC469496
0.7603	Intermediate Similarity	NPC198539
0.7603	Intermediate Similarity	NPC56448
0.7603	Intermediate Similarity	NPC49451
0.7603	Intermediate Similarity	NPC321496
0.7603	Intermediate Similarity	NPC469454
0.76	Intermediate Similarity	NPC472001
0.76	Intermediate Similarity	NPC472401
0.7597	Intermediate Similarity	NPC264192
0.7597	Intermediate Similarity	NPC476854
0.7586	Intermediate Similarity	NPC320154
0.7586	Intermediate Similarity	NPC72842
0.7586	Intermediate Similarity	NPC475945
0.7586	Intermediate Similarity	NPC475871
0.7586	Intermediate Similarity	NPC99510
0.7583	Intermediate Similarity	NPC247031
0.7583	Intermediate Similarity	NPC317107
0.7583	Intermediate Similarity	NPC171888
0.7583	Intermediate Similarity	NPC201992
0.7583	Intermediate Similarity	NPC146945
0.7583	Intermediate Similarity	NPC97939
0.7583	Intermediate Similarity	NPC132790
0.7583	Intermediate Similarity	NPC100329

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 NPC476107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1734
0.2-0.3	3517
0.3-0.4	2366
0.4-0.5	847
0.5-0.6	318
0.6-0.7	131
0.7-0.8	17
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
0.7333	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7492	Approved
0.7244	Intermediate Similarity	NPD6054	Approved
0.7231	Intermediate Similarity	NPD6616	Approved
0.7213	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7319	Approved
0.7188	Intermediate Similarity	NPD6016	Approved
0.7188	Intermediate Similarity	NPD6015	Approved
0.7176	Intermediate Similarity	NPD7078	Approved
0.7132	Intermediate Similarity	NPD5988	Approved
0.7132	Intermediate Similarity	NPD6370	Approved
0.7131	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7736	Approved
0.7109	Intermediate Similarity	NPD6059	Approved
0.7109	Intermediate Similarity	NPD6319	Approved
0.7107	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4225	Approved
0.7045	Intermediate Similarity	NPD8293	Discontinued
0.7008	Intermediate Similarity	NPD7115	Discovery
0.697	Remote Similarity	NPD7507	Approved
0.6967	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8328	Phase 3
0.6923	Remote Similarity	NPD8513	Phase 3
0.6911	Remote Similarity	NPD6686	Approved
0.6875	Remote Similarity	NPD6009	Approved
0.6833	Remote Similarity	NPD5344	Discontinued
0.6825	Remote Similarity	NPD6053	Discontinued
0.6794	Remote Similarity	NPD8517	Approved
0.6794	Remote Similarity	NPD8515	Approved
0.6794	Remote Similarity	NPD8516	Approved
0.6772	Remote Similarity	NPD4632	Approved
0.6769	Remote Similarity	NPD7516	Approved
0.6752	Remote Similarity	NPD5282	Discontinued
0.6746	Remote Similarity	NPD6649	Approved
0.6746	Remote Similarity	NPD6650	Approved
0.672	Remote Similarity	NPD6372	Approved
0.672	Remote Similarity	NPD6373	Approved
0.6695	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5697	Approved
0.6693	Remote Similarity	NPD6882	Approved
0.6693	Remote Similarity	NPD8297	Approved
0.6692	Remote Similarity	NPD7328	Approved
0.6692	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.664	Remote Similarity	NPD6899	Approved
0.664	Remote Similarity	NPD6881	Approved
0.664	Remote Similarity	NPD7320	Approved
0.6618	Remote Similarity	NPD6033	Approved
0.6615	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6008	Approved
0.6613	Remote Similarity	NPD6675	Approved
0.6613	Remote Similarity	NPD7128	Approved
0.6613	Remote Similarity	NPD6402	Approved
0.6613	Remote Similarity	NPD5739	Approved
0.6612	Remote Similarity	NPD6648	Approved
0.6596	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6013	Approved
0.6587	Remote Similarity	NPD6014	Approved
0.6587	Remote Similarity	NPD6012	Approved
0.656	Remote Similarity	NPD5701	Approved
0.6544	Remote Similarity	NPD8074	Phase 3
0.6541	Remote Similarity	NPD5983	Phase 2
0.6535	Remote Similarity	NPD7102	Approved
0.6535	Remote Similarity	NPD6883	Approved
0.6535	Remote Similarity	NPD6371	Approved
0.6535	Remote Similarity	NPD4634	Approved
0.6535	Remote Similarity	NPD7290	Approved
0.6508	Remote Similarity	NPD6011	Approved
0.6484	Remote Similarity	NPD6617	Approved
0.6484	Remote Similarity	NPD8130	Phase 1
0.6484	Remote Similarity	NPD6847	Approved
0.6484	Remote Similarity	NPD6869	Approved
0.6444	Remote Similarity	NPD7604	Phase 2
0.6423	Remote Similarity	NPD1700	Approved
0.6418	Remote Similarity	NPD8379	Approved
0.6418	Remote Similarity	NPD8296	Approved
0.6418	Remote Similarity	NPD8335	Approved
0.6418	Remote Similarity	NPD7503	Approved
0.6418	Remote Similarity	NPD8380	Approved
0.6418	Remote Similarity	NPD8378	Approved
0.6418	Remote Similarity	NPD8033	Approved
0.6393	Remote Similarity	NPD7638	Approved
0.6357	Remote Similarity	NPD7260	Phase 2
0.6356	Remote Similarity	NPD6698	Approved
0.6356	Remote Similarity	NPD46	Approved
0.635	Remote Similarity	NPD6336	Discontinued
0.6348	Remote Similarity	NPD1694	Approved
0.6348	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD8377	Approved
0.6343	Remote Similarity	NPD8294	Approved
0.6341	Remote Similarity	NPD7639	Approved
0.6341	Remote Similarity	NPD7640	Approved
0.6328	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD6845	Suspended
0.6288	Remote Similarity	NPD6274	Approved
0.6281	Remote Similarity	NPD5695	Phase 3
0.626	Remote Similarity	NPD5696	Approved
0.626	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8080	Discontinued
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.624	Remote Similarity	NPD5211	Phase 2
0.6231	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5285	Approved
0.621	Remote Similarity	NPD4696	Approved
0.621	Remote Similarity	NPD5286	Approved
0.6179	Remote Similarity	NPD6084	Phase 2
0.6179	Remote Similarity	NPD4755	Approved
0.6179	Remote Similarity	NPD6083	Phase 2
0.6179	Remote Similarity	NPD7902	Approved
0.6176	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6412	Phase 2
0.617	Remote Similarity	NPD5956	Approved
0.6167	Remote Similarity	NPD7983	Approved
0.6148	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD7101	Approved
0.6142	Remote Similarity	NPD5141	Approved
0.6134	Remote Similarity	NPD1695	Approved
0.6119	Remote Similarity	NPD6317	Approved
0.6116	Remote Similarity	NPD6399	Phase 3
0.6111	Remote Similarity	NPD5224	Approved
0.6111	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD4633	Approved
0.6111	Remote Similarity	NPD5226	Approved
0.6098	Remote Similarity	NPD4697	Phase 3
0.608	Remote Similarity	NPD4700	Approved
0.6074	Remote Similarity	NPD6335	Approved
0.6074	Remote Similarity	NPD6313	Approved
0.6074	Remote Similarity	NPD6314	Approved
0.6069	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD5174	Approved
0.6063	Remote Similarity	NPD5175	Approved
0.6059	Remote Similarity	NPD8407	Phase 2
0.6058	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6110	Phase 1
0.6033	Remote Similarity	NPD5693	Phase 1
0.6032	Remote Similarity	NPD5223	Approved
0.6023	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD8415	Approved
0.5988	Remote Similarity	NPD8434	Phase 2
0.5986	Remote Similarity	NPD6334	Approved
0.5986	Remote Similarity	NPD6333	Approved
0.5976	Remote Similarity	NPD8368	Discontinued
0.5971	Remote Similarity	NPD7642	Approved
0.5968	Remote Similarity	NPD5221	Approved
0.5968	Remote Similarity	NPD5222	Approved
0.5968	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD3573	Approved
0.595	Remote Similarity	NPD7838	Discovery
0.5948	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD6908	Approved
0.5942	Remote Similarity	NPD6909	Approved
0.5935	Remote Similarity	NPD7900	Approved
0.5935	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7748	Approved
0.5928	Remote Similarity	NPD7799	Discontinued
0.5926	Remote Similarity	NPD6868	Approved
0.592	Remote Similarity	NPD5173	Approved
0.5917	Remote Similarity	NPD5737	Approved
0.5917	Remote Similarity	NPD6672	Approved
0.5887	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD5128	Approved
0.5878	Remote Similarity	NPD4730	Approved
0.5878	Remote Similarity	NPD4729	Approved
0.5868	Remote Similarity	NPD6101	Approved
0.5868	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8338	Approved
0.5859	Remote Similarity	NPD7632	Discontinued
0.5857	Remote Similarity	NPD7829	Approved
0.5857	Remote Similarity	NPD7830	Approved
0.5857	Remote Similarity	NPD6067	Discontinued
0.5846	Remote Similarity	NPD4768	Approved
0.5846	Remote Similarity	NPD4767	Approved
0.582	Remote Similarity	NPD5785	Approved
0.582	Remote Similarity	NPD3168	Discontinued
0.5814	Remote Similarity	NPD4754	Approved
0.5789	Remote Similarity	NPD5248	Approved
0.5789	Remote Similarity	NPD5247	Approved
0.5789	Remote Similarity	NPD5249	Phase 3
0.5789	Remote Similarity	NPD5251	Approved
0.5789	Remote Similarity	NPD5250	Approved
0.5776	Remote Similarity	NPD4695	Discontinued
0.5775	Remote Similarity	NPD8451	Approved
0.5772	Remote Similarity	NPD6411	Approved
0.5772	Remote Similarity	NPD7515	Phase 2
0.5772	Remote Similarity	NPD6079	Approved
0.5766	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.576	Remote Similarity	NPD4629	Approved
0.576	Remote Similarity	NPD5210	Approved
0.575	Remote Similarity	NPD3618	Phase 1
0.575	Remote Similarity	NPD5786	Approved
0.575	Remote Similarity	NPD4249	Approved
0.5746	Remote Similarity	NPD5215	Approved
0.5746	Remote Similarity	NPD5216	Approved
0.5746	Remote Similarity	NPD5217	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