NPASS Compound

Structure

NPC109787 OpenBabel07101719132D 33 39 0 0 1 0 0 0 0 0999 V2000 -0.2719 4.3654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2534 4.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3433 3.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7393 1.0380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0016 1.0175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8174 1.1239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3393 0.3329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1309 0.9776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0016 0.8048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6331 1.0175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9652 -0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7252 0.2033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8293 0.4650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2744 0.9794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 1.4157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3869 2.4742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6700 4.2355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9883 2.6494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1802 0.9657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8174 0.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6331 0.8048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2902 -0.2918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8035 1.7235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8226 0.1987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4489 0.4857 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8054 1.4364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8174 0.4857 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4489 0.6984 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0940 0.3398 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7059 1.7416 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0239 1.9014 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.9158 2.8588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 30 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 10 21 2 0 0 0 0 11 22 2 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 15 1 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 18 31 1 0 0 0 0 18 33 2 0 0 0 0 19 23 1 0 0 0 0 19 24 2 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 23 32 1 6 0 0 0 24 28 1 0 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 26 27 1 1 0 0 0 26 31 1 0 0 0 0 26 32 1 0 0 0 0 27 28 1 6 0 0 0 28 13 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.26
Volume:	464.634
LogP:	3.56
LogD:	3.112
LogS:	-4.256
# Rotatable Bonds:	2
TPSA:	38.82
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	6.204
Fsp3:	0.464
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.203
MDCK Permeability:	2.657097502378747e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.892
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.289
Plasma Protein Binding (PPB):	88.07378387451172%
Volume Distribution (VD):	2.911
Pgp-substrate:	9.06268310546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.866
CYP2C9-substrate:	0.538
CYP2D6-inhibitor:	0.236
CYP2D6-substrate:	0.797
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.742

ADMET: Excretion

Clearance (CL):	3.436
Half-life (T1/2):	0.433

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.942
Drug-inuced Liver Injury (DILI):	0.227
AMES Toxicity:	0.555
Rat Oral Acute Toxicity:	0.468
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.377
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.767

Download Data

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

Natural Product: NPC109787

Natural Product ID:	NPC109787
*Common Name:**	Communesin E
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AJKLOOXVDIANRY-MGDFUXISSA-N
Standard InCHI:	InChI=1S/C28H32N4O/c1-17(2)16-23-19-8-7-11-22-24(19)28-13-15-32(23)26-27(28,12-14-31(26)18(3)33)20-9-5-6-10-21(20)29-25(28)30(22)4/h5-11,16,23,25-26,29H,12-15H2,1-4H3/t23-,25-,26-,27+,28+/m1/s1
SMILES:	CC(=C[C@@H]1c2cccc3c2[C@@]24CCN1[C@@H]1[C@]4(CCN1C(=O)C)c1ccccc1N[C@@H]2N3C)C
Synthetic Gene Cluster:	BGC0001205;
ChEMBL Identifier:	CHEMBL2269099
PubChem CID:	24741372
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001913] Alpha carbolines

*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
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15056914]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270557]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20415462]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24024763]
NPO28107	Penicillium expansum	Species	Aspergillaceae	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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3978	Organism	Bombyx mori	Bombyx mori	LD50	=	80.0	mg.kg-1	PMID[524608]

☑ 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 NPC109787 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	466
0.1-0.2	2549
0.2-0.3	18564
0.3-0.4	13952
0.4-0.5	4941
0.5-0.6	1917
0.6-0.7	264
0.7-0.8	32
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8519	High Similarity	NPC256288
0.8466	Intermediate Similarity	NPC2933
0.8415	Intermediate Similarity	NPC259626
0.8364	Intermediate Similarity	NPC473615
0.8313	Intermediate Similarity	NPC229484
0.8263	Intermediate Similarity	NPC292675
0.8258	Intermediate Similarity	NPC222029
0.8205	Intermediate Similarity	NPC276085
0.8151	Intermediate Similarity	NPC471123
0.8086	Intermediate Similarity	NPC242269
0.7935	Intermediate Similarity	NPC66936
0.7902	Intermediate Similarity	NPC252794
0.7847	Intermediate Similarity	NPC145754
0.7801	Intermediate Similarity	NPC475915
0.78	Intermediate Similarity	NPC469560
0.7643	Intermediate Similarity	NPC473329
0.7632	Intermediate Similarity	NPC130251
0.755	Intermediate Similarity	NPC267508
0.7468	Intermediate Similarity	NPC186284
0.7468	Intermediate Similarity	NPC22082
0.7378	Intermediate Similarity	NPC68650
0.7355	Intermediate Similarity	NPC301760
0.7333	Intermediate Similarity	NPC469741
0.7288	Intermediate Similarity	NPC128582
0.7267	Intermediate Similarity	NPC206592
0.7262	Intermediate Similarity	NPC63047
0.7262	Intermediate Similarity	NPC475248
0.7261	Intermediate Similarity	NPC469537
0.7257	Intermediate Similarity	NPC307396
0.7235	Intermediate Similarity	NPC285622
0.7233	Intermediate Similarity	NPC264589
0.7212	Intermediate Similarity	NPC471122
0.7143	Intermediate Similarity	NPC471124
0.7135	Intermediate Similarity	NPC473743
0.7021	Intermediate Similarity	NPC477173
0.7019	Intermediate Similarity	NPC469735
0.6994	Remote Similarity	NPC318086
0.6984	Remote Similarity	NPC470488
0.6968	Remote Similarity	NPC162417
0.6968	Remote Similarity	NPC316104
0.6964	Remote Similarity	NPC309531
0.6964	Remote Similarity	NPC472102
0.6961	Remote Similarity	NPC276430
0.6951	Remote Similarity	NPC243756
0.6951	Remote Similarity	NPC154602
0.6932	Remote Similarity	NPC286994
0.6923	Remote Similarity	NPC99632
0.6923	Remote Similarity	NPC282339
0.6909	Remote Similarity	NPC117032
0.6901	Remote Similarity	NPC279527
0.6901	Remote Similarity	NPC214960
0.6879	Remote Similarity	NPC355
0.6849	Remote Similarity	NPC313673
0.6848	Remote Similarity	NPC475763
0.6845	Remote Similarity	NPC113946
0.6839	Remote Similarity	NPC214626
0.6839	Remote Similarity	NPC139085
0.6839	Remote Similarity	NPC251212
0.6825	Remote Similarity	NPC477179
0.6824	Remote Similarity	NPC286871
0.68	Remote Similarity	NPC475097
0.6789	Remote Similarity	NPC477178
0.6789	Remote Similarity	NPC254850
0.6789	Remote Similarity	NPC477181
0.6789	Remote Similarity	NPC477180
0.6772	Remote Similarity	NPC471436
0.6771	Remote Similarity	NPC470491
0.6771	Remote Similarity	NPC475259
0.6771	Remote Similarity	NPC471950
0.6771	Remote Similarity	NPC471945
0.6768	Remote Similarity	NPC469740
0.6768	Remote Similarity	NPC212799
0.6765	Remote Similarity	NPC225319
0.6757	Remote Similarity	NPC264580
0.6754	Remote Similarity	NPC477174
0.6754	Remote Similarity	NPC470490
0.6744	Remote Similarity	NPC472106
0.6744	Remote Similarity	NPC475420
0.6743	Remote Similarity	NPC161861
0.674	Remote Similarity	NPC141612
0.674	Remote Similarity	NPC135601
0.674	Remote Similarity	NPC17273
0.6736	Remote Similarity	NPC471946
0.6736	Remote Similarity	NPC471951
0.6725	Remote Similarity	NPC472120
0.6725	Remote Similarity	NPC176983
0.6725	Remote Similarity	NPC472101
0.6707	Remote Similarity	NPC285381
0.6707	Remote Similarity	NPC122106
0.6706	Remote Similarity	NPC221786
0.6706	Remote Similarity	NPC193410
0.6706	Remote Similarity	NPC36495
0.6706	Remote Similarity	NPC474880
0.6706	Remote Similarity	NPC475990
0.6702	Remote Similarity	NPC470489
0.6691	Remote Similarity	NPC291610
0.669	Remote Similarity	NPC79618
0.6688	Remote Similarity	NPC478079
0.6687	Remote Similarity	NPC311330
0.6667	Remote Similarity	NPC248117
0.6647	Remote Similarity	NPC61013
0.6647	Remote Similarity	NPC33421
0.6615	Remote Similarity	NPC191817
0.6615	Remote Similarity	NPC475359
0.6614	Remote Similarity	NPC106118
0.6606	Remote Similarity	NPC470440
0.6588	Remote Similarity	NPC29285
0.6588	Remote Similarity	NPC469536
0.6577	Remote Similarity	NPC313449
0.6575	Remote Similarity	NPC470205
0.657	Remote Similarity	NPC229173
0.6554	Remote Similarity	NPC473880
0.655	Remote Similarity	NPC104345
0.655	Remote Similarity	NPC469428
0.6538	Remote Similarity	NPC472294
0.6536	Remote Similarity	NPC260075
0.6532	Remote Similarity	NPC472117
0.6532	Remote Similarity	NPC194881
0.6529	Remote Similarity	NPC476219
0.6529	Remote Similarity	NPC476297
0.6527	Remote Similarity	NPC21605
0.6517	Remote Similarity	NPC470548
0.6508	Remote Similarity	NPC162440
0.648	Remote Similarity	NPC320147
0.6477	Remote Similarity	NPC224970
0.6477	Remote Similarity	NPC223595
0.6477	Remote Similarity	NPC167724
0.6471	Remote Similarity	NPC478076
0.6471	Remote Similarity	NPC471386
0.6464	Remote Similarity	NPC16659
0.6461	Remote Similarity	NPC177261
0.6458	Remote Similarity	NPC434
0.6456	Remote Similarity	NPC126458
0.6453	Remote Similarity	NPC123241
0.645	Remote Similarity	NPC470732
0.645	Remote Similarity	NPC470731
0.6442	Remote Similarity	NPC315051
0.6433	Remote Similarity	NPC209389
0.6432	Remote Similarity	NPC285841
0.6424	Remote Similarity	NPC473868
0.6424	Remote Similarity	NPC63157
0.6414	Remote Similarity	NPC302790
0.6409	Remote Similarity	NPC265710
0.6402	Remote Similarity	NPC471164
0.6377	Remote Similarity	NPC329430
0.6369	Remote Similarity	NPC96901
0.6368	Remote Similarity	NPC470787
0.6368	Remote Similarity	NPC472540
0.6368	Remote Similarity	NPC472539
0.6364	Remote Similarity	NPC105055
0.6364	Remote Similarity	NPC22689
0.6354	Remote Similarity	NPC240088
0.6354	Remote Similarity	NPC473380
0.635	Remote Similarity	NPC471663
0.6348	Remote Similarity	NPC472118
0.6348	Remote Similarity	NPC474897
0.6343	Remote Similarity	NPC293458
0.6341	Remote Similarity	NPC243162
0.6335	Remote Similarity	NPC472541
0.6335	Remote Similarity	NPC472542
0.6327	Remote Similarity	NPC225400
0.6322	Remote Similarity	NPC56765
0.6312	Remote Similarity	NPC53044
0.6312	Remote Similarity	NPC473962
0.6311	Remote Similarity	NPC40455
0.6307	Remote Similarity	NPC271797
0.6307	Remote Similarity	NPC21174
0.6304	Remote Similarity	NPC477159
0.6303	Remote Similarity	NPC470301
0.6303	Remote Similarity	NPC88097
0.6298	Remote Similarity	NPC203202
0.6298	Remote Similarity	NPC264482
0.6294	Remote Similarity	NPC472538
0.6294	Remote Similarity	NPC471155
0.6294	Remote Similarity	NPC470786
0.6292	Remote Similarity	NPC33507
0.6287	Remote Similarity	NPC20144
0.6286	Remote Similarity	NPC201424
0.6279	Remote Similarity	NPC295021
0.6277	Remote Similarity	NPC473569
0.6277	Remote Similarity	NPC473298
0.6269	Remote Similarity	NPC473006
0.6266	Remote Similarity	NPC476950
0.6265	Remote Similarity	NPC2949
0.6263	Remote Similarity	NPC270241
0.6258	Remote Similarity	NPC268534
0.6258	Remote Similarity	NPC325599
0.625	Remote Similarity	NPC471199
0.6237	Remote Similarity	NPC476095
0.6235	Remote Similarity	NPC313352
0.6234	Remote Similarity	NPC316582
0.623	Remote Similarity	NPC6974
0.623	Remote Similarity	NPC218594
0.623	Remote Similarity	NPC99043
0.6229	Remote Similarity	NPC41257
0.6225	Remote Similarity	NPC248601
0.6213	Remote Similarity	NPC204141
0.6212	Remote Similarity	NPC477065
0.6209	Remote Similarity	NPC228515
0.62	Remote Similarity	NPC187036

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 NPC109787 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	529
0.2-0.3	1135
0.3-0.4	1691
0.4-0.5	3363
0.5-0.6	1878
0.6-0.7	288
0.7-0.8	21
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
0.7655	Intermediate Similarity	NPD1950	Approved
0.7655	Intermediate Similarity	NPD1949	Approved
0.7534	Intermediate Similarity	NPD3240	Phase 2
0.75	Intermediate Similarity	NPD6358	Phase 2
0.7383	Intermediate Similarity	NPD8263	Discontinued
0.7357	Intermediate Similarity	NPD5179	Approved
0.7357	Intermediate Similarity	NPD2914	Approved
0.7357	Intermediate Similarity	NPD2913	Approved
0.7357	Intermediate Similarity	NPD5181	Approved
0.7357	Intermediate Similarity	NPD5180	Approved
0.723	Intermediate Similarity	NPD8128	Discontinued
0.7229	Intermediate Similarity	NPD5551	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3001	Approved
0.7214	Intermediate Similarity	NPD2039	Approved
0.7214	Intermediate Similarity	NPD2038	Approved
0.7214	Intermediate Similarity	NPD2999	Approved
0.7211	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6768	Approved
0.7181	Intermediate Similarity	NPD2840	Approved
0.7172	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6342	Discontinued
0.7143	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6318	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4116	Approved
0.7048	Intermediate Similarity	NPD8630	Approved
0.703	Intermediate Similarity	NPD7072	Phase 2
0.7019	Intermediate Similarity	NPD5839	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8240	Discontinued
0.695	Remote Similarity	NPD7633	Discontinued
0.6944	Remote Similarity	NPD5629	Discontinued
0.6933	Remote Similarity	NPD7464	Phase 3
0.6928	Remote Similarity	NPD3424	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3625	Discontinued
0.6909	Remote Similarity	NPD8402	Approved
0.6909	Remote Similarity	NPD3248	Phase 1
0.6909	Remote Similarity	NPD8401	Approved
0.6909	Remote Similarity	NPD8400	Approved
0.6903	Remote Similarity	NPD7578	Phase 2
0.6899	Remote Similarity	NPD7254	Discontinued
0.6894	Remote Similarity	NPD5918	Discontinued
0.6887	Remote Similarity	NPD2962	Approved
0.6887	Remote Similarity	NPD2961	Approved
0.6886	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3545	Approved
0.6857	Remote Similarity	NPD3546	Approved
0.6852	Remote Similarity	NPD5932	Phase 3
0.6852	Remote Similarity	NPD5931	Phase 3
0.6852	Remote Similarity	NPD5933	Phase 3
0.6852	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5517	Phase 2
0.6824	Remote Similarity	NPD5516	Phase 2
0.6818	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4114	Approved
0.6809	Remote Similarity	NPD4115	Approved
0.6795	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1723	Phase 2
0.6781	Remote Similarity	NPD1720	Phase 2
0.6776	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2790	Discontinued
0.6753	Remote Similarity	NPD2908	Phase 3
0.6753	Remote Similarity	NPD2909	Phase 3
0.675	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1064	Approved
0.6738	Remote Similarity	NPD1065	Approved
0.6732	Remote Similarity	NPD6900	Discontinued
0.6728	Remote Similarity	NPD5526	Phase 2
0.6728	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5024	Approved
0.6723	Remote Similarity	NPD5600	Discontinued
0.6708	Remote Similarity	NPD2010	Phase 3
0.6703	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5253	Approved
0.6667	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6566	Discontinued
0.6667	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6489	Phase 3
0.6667	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8060	Phase 1
0.6645	Remote Similarity	NPD4549	Discontinued
0.6627	Remote Similarity	NPD5941	Approved
0.6627	Remote Similarity	NPD5942	Approved
0.6625	Remote Similarity	NPD5318	Discontinued
0.661	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5131	Approved
0.6601	Remote Similarity	NPD2938	Approved
0.6601	Remote Similarity	NPD2940	Approved
0.6591	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2150	Discontinued
0.6585	Remote Similarity	NPD7099	Approved
0.6577	Remote Similarity	NPD7480	Approved
0.6577	Remote Similarity	NPD7481	Approved
0.6573	Remote Similarity	NPD4075	Phase 2
0.6571	Remote Similarity	NPD7890	Discontinued
0.6566	Remote Similarity	NPD4402	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6467	Approved
0.6566	Remote Similarity	NPD6466	Approved
0.6562	Remote Similarity	NPD8125	Discontinued
0.6559	Remote Similarity	NPD6200	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4430	Phase 2
0.6522	Remote Similarity	NPD4411	Phase 1
0.6522	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6069	Approved
0.651	Remote Similarity	NPD6070	Approved
0.6506	Remote Similarity	NPD1524	Phase 1
0.6503	Remote Similarity	NPD2093	Discontinued
0.6497	Remote Similarity	NPD7663	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7091	Discontinued
0.6486	Remote Similarity	NPD5631	Phase 3
0.648	Remote Similarity	NPD6044	Discontinued
0.6478	Remote Similarity	NPD2949	Approved
0.6478	Remote Similarity	NPD2950	Approved
0.6474	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5993	Phase 1
0.6471	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6878	Phase 2
0.6464	Remote Similarity	NPD6879	Phase 2
0.6453	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2143	Discontinued
0.6446	Remote Similarity	NPD5060	Phase 1
0.6441	Remote Similarity	NPD5531	Discontinued
0.6438	Remote Similarity	NPD7200	Approved
0.6433	Remote Similarity	NPD5606	Discontinued
0.6429	Remote Similarity	NPD5423	Phase 2
0.6424	Remote Similarity	NPD5657	Phase 3
0.6424	Remote Similarity	NPD6301	Phase 2
0.6424	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6664	Approved
0.6416	Remote Similarity	NPD7599	Phase 2
0.6402	Remote Similarity	NPD7044	Discontinued
0.64	Remote Similarity	NPD3790	Phase 2
0.6393	Remote Similarity	NPD3318	Approved
0.6393	Remote Similarity	NPD3319	Phase 1
0.6393	Remote Similarity	NPD3320	Approved
0.6392	Remote Similarity	NPD4365	Phase 2
0.6387	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4347	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7786	Discontinued
0.6379	Remote Similarity	NPD5989	Phase 1
0.6378	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD3551	Approved
0.637	Remote Similarity	NPD3548	Approved
0.6369	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7088	Discontinued
0.6358	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD8355	Approved
0.6353	Remote Similarity	NPD8353	Approved
0.6352	Remote Similarity	NPD4781	Approved
0.6352	Remote Similarity	NPD4783	Approved
0.6352	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7210	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6771	Discontinued
0.6341	Remote Similarity	NPD1870	Approved
0.634	Remote Similarity	NPD6892	Discontinued
0.6337	Remote Similarity	NPD5743	Approved
0.6337	Remote Similarity	NPD5741	Approved
0.6337	Remote Similarity	NPD5742	Approved
0.6331	Remote Similarity	NPD2005	Discontinued
0.6325	Remote Similarity	NPD2820	Phase 3
0.6325	Remote Similarity	NPD2129	Approved
0.6319	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD3077	Approved
0.6319	Remote Similarity	NPD3078	Approved
0.6319	Remote Similarity	NPD3079	Approved
0.6319	Remote Similarity	NPD3076	Approved
0.6307	Remote Similarity	NPD3583	Phase 2
0.6307	Remote Similarity	NPD3323	Discontinued
0.6303	Remote Similarity	NPD5518	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD2463	Approved
0.6291	Remote Similarity	NPD2464	Approved
0.6291	Remote Similarity	NPD2467	Approved
0.6289	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7600	Phase 2
0.6284	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4120	Approved
0.6279	Remote Similarity	NPD4121	Phase 3
0.6279	Remote Similarity	NPD8354	Approved
0.6278	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3498	Approved
0.6275	Remote Similarity	NPD3499	Approved
0.6273	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD4970	Phase 2
0.6272	Remote Similarity	NPD4968	Phase 2
0.6272	Remote Similarity	NPD4969	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD1683	Approved
0.627	Remote Similarity	NPD7564	Discontinued
0.6269	Remote Similarity	NPD6603	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD5630	Phase 1
0.6267	Remote Similarity	NPD2508	Discontinued

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