NPASS Compound

Structure

NPC112981 OpenBabel07101719512D 29 31 0 0 0 0 0 0 0 0999 V2000 -2.7105 -1.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 4.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8371 0.0731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -0.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2766 -0.6784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1044 3.7517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8399 0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5382 2.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 2.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6677 4.5779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 0.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0988 3.6022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5984 -0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.2470 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 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 29 1 0 0 0 0 21 28 1 0 0 0 0 22 28 1 0 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	409.708
LogP:	4.351
LogD:	3.574
LogS:	-4.461
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.495
Synthetic Accessibility Score:	3.647
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.998
MDCK Permeability:	1.8396520317764953e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.186
20% Bioavailability (F20%):	0.478
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	98.1484146118164%
Volume Distribution (VD):	0.662
Pgp-substrate:	4.544912815093994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.856
CYP1A2-substrate:	0.859
CYP2C19-inhibitor:	0.441
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.621
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.728
CYP3A4-inhibitor:	0.292
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	10.523
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.025
Drug-inuced Liver Injury (DILI):	0.201
AMES Toxicity:	0.247
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.723
Carcinogencity:	0.248
Eye Corrosion:	0.003
Eye Irritation:	0.819
Respiratory Toxicity:	0.822

Download Data

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

Natural Product: NPC112981

Natural Product ID:	NPC112981
*Common Name:**	1,7-Bis[(E)-But-2-En-2-Yl]-3,9-Dihydroxy-10-(Hydroxymethyl)-4-Methylbenzo[B][1,4]Benzodioxepin-6-One
IUPAC Name:	1,7-bis[(E)-but-2-en-2-yl]-3,9-dihydroxy-10-(hydroxymethyl)-4-methylbenzo[b][1,4]benzodioxepin-6-one
Synonyms:
Standard InCHIKey:	DHFSUMFYDGKIBS-GNXRPPCSSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-6-11(3)14-8-18(26)16(10-24)21-19(14)23(27)29-20-13(5)17(25)9-15(12(4)7-2)22(20)28-21/h6-9,24-26H,10H2,1-5H3/b11-6+,12-7+
SMILES:	C/C=C(/c1cc(O)c(c2c1C(=O)Oc1c(O2)c(cc(c1C)O)/C(=C/C)/C)CO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471886
PubChem CID:	16086599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO33090	bcc 8616	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16989536]

☑ 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

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[482328]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	5.0	ug.mL-1	PMID[482328]

☑ 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 NPC112981 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	385
0.1-0.2	1665
0.2-0.3	4046
0.3-0.4	9298
0.4-0.5	9012
0.5-0.6	3429
0.6-0.7	5073
0.7-0.8	6466
0.8-0.85	2655
0.85-0.9	586
0.9-0.95	70
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC20216
0.9935	High Similarity	NPC156082
0.9748	High Similarity	NPC17219
0.9747	High Similarity	NPC292788
0.9747	High Similarity	NPC272485
0.9625	High Similarity	NPC20543
0.9625	High Similarity	NPC246716
0.9625	High Similarity	NPC239440
0.9563	High Similarity	NPC26568
0.9506	High Similarity	NPC181523
0.9503	High Similarity	NPC1827
0.9503	High Similarity	NPC10576
0.9484	High Similarity	NPC471800
0.9448	High Similarity	NPC139350
0.9448	High Similarity	NPC289147
0.9427	High Similarity	NPC238381
0.9427	High Similarity	NPC168616
0.9427	High Similarity	NPC83763
0.9355	High Similarity	NPC273483
0.9321	High Similarity	NPC49487
0.9321	High Similarity	NPC99613
0.9317	High Similarity	NPC29160
0.9313	High Similarity	NPC474350
0.9313	High Similarity	NPC300984
0.9308	High Similarity	NPC303565
0.9277	High Similarity	NPC240887
0.9277	High Similarity	NPC113446
0.9277	High Similarity	NPC329161
0.9277	High Similarity	NPC470091
0.9264	High Similarity	NPC109827
0.9264	High Similarity	NPC124470
0.9259	High Similarity	NPC234331
0.9255	High Similarity	NPC267153
0.925	High Similarity	NPC93739
0.9207	High Similarity	NPC158226
0.9202	High Similarity	NPC165979
0.9202	High Similarity	NPC163130
0.9193	High Similarity	NPC284007
0.9193	High Similarity	NPC197168
0.9193	High Similarity	NPC234004
0.9187	High Similarity	NPC66288
0.9177	High Similarity	NPC472456
0.9161	High Similarity	NPC291049
0.9161	High Similarity	NPC233267
0.9136	High Similarity	NPC25361
0.9136	High Similarity	NPC8070
0.913	High Similarity	NPC8300
0.9125	High Similarity	NPC475886
0.9125	High Similarity	NPC47623
0.9125	High Similarity	NPC143050
0.9125	High Similarity	NPC200594
0.9125	High Similarity	NPC474287
0.9119	High Similarity	NPC165977
0.9119	High Similarity	NPC217677
0.9097	High Similarity	NPC105415
0.908	High Similarity	NPC472452
0.9074	High Similarity	NPC270837
0.9074	High Similarity	NPC7483
0.9074	High Similarity	NPC236132
0.9068	High Similarity	NPC474351
0.9068	High Similarity	NPC475883
0.9068	High Similarity	NPC474186
0.9068	High Similarity	NPC474187
0.9062	High Similarity	NPC45846
0.9057	High Similarity	NPC54928
0.9045	High Similarity	NPC133856
0.9018	High Similarity	NPC130920
0.9018	High Similarity	NPC85057
0.9012	High Similarity	NPC294965
0.9012	High Similarity	NPC144843
0.9012	High Similarity	NPC108767
0.9006	High Similarity	NPC56085
0.9006	High Similarity	NPC14353
0.9006	High Similarity	NPC228785
0.8994	High Similarity	NPC149618
0.8994	High Similarity	NPC89625
0.8987	High Similarity	NPC199773
0.8987	High Similarity	NPC289968
0.8981	High Similarity	NPC225129
0.8951	High Similarity	NPC349525
0.8951	High Similarity	NPC278052
0.8951	High Similarity	NPC40491
0.8951	High Similarity	NPC103201
0.8951	High Similarity	NPC473106
0.8951	High Similarity	NPC61010
0.8944	High Similarity	NPC85121
0.8944	High Similarity	NPC100123
0.8938	High Similarity	NPC146211
0.8931	High Similarity	NPC475895
0.8924	High Similarity	NPC204350
0.8909	High Similarity	NPC477154
0.8909	High Similarity	NPC474024
0.8909	High Similarity	NPC6588
0.8909	High Similarity	NPC117854
0.8903	High Similarity	NPC134621
0.8902	High Similarity	NPC326520
0.8896	High Similarity	NPC229632
0.8889	High Similarity	NPC119224
0.8889	High Similarity	NPC299436
0.8889	High Similarity	NPC292415
0.8889	High Similarity	NPC320359
0.8889	High Similarity	NPC36217
0.8882	High Similarity	NPC108456
0.8882	High Similarity	NPC241904
0.8882	High Similarity	NPC300727
0.8882	High Similarity	NPC223787
0.8875	High Similarity	NPC20541
0.8875	High Similarity	NPC16082
0.8875	High Similarity	NPC82592
0.8868	High Similarity	NPC217447
0.8868	High Similarity	NPC175978
0.8861	High Similarity	NPC213382
0.8861	High Similarity	NPC164527
0.8848	High Similarity	NPC170245
0.8848	High Similarity	NPC43319
0.8848	High Similarity	NPC272502
0.8848	High Similarity	NPC37870
0.8846	High Similarity	NPC237208
0.8846	High Similarity	NPC225173
0.8846	High Similarity	NPC163846
0.8841	High Similarity	NPC474240
0.8841	High Similarity	NPC152659
0.8841	High Similarity	NPC220313
0.8841	High Similarity	NPC248638
0.8841	High Similarity	NPC477689
0.8841	High Similarity	NPC236521
0.8839	High Similarity	NPC66404
0.8839	High Similarity	NPC95123
0.8827	High Similarity	NPC329091
0.8827	High Similarity	NPC476242
0.882	High Similarity	NPC142339
0.882	High Similarity	NPC274730
0.882	High Similarity	NPC227062
0.8812	High Similarity	NPC280937
0.8812	High Similarity	NPC281477
0.8812	High Similarity	NPC135522
0.8812	High Similarity	NPC298802
0.8797	High Similarity	NPC285527
0.8797	High Similarity	NPC106334
0.8797	High Similarity	NPC328119
0.8795	High Similarity	NPC218226
0.879	High Similarity	NPC125801
0.8788	High Similarity	NPC239752
0.8788	High Similarity	NPC475888
0.8788	High Similarity	NPC472450
0.8788	High Similarity	NPC303174
0.8788	High Similarity	NPC275780
0.8782	High Similarity	NPC29577
0.878	High Similarity	NPC25152
0.878	High Similarity	NPC52204
0.878	High Similarity	NPC470694
0.878	High Similarity	NPC201800
0.878	High Similarity	NPC211107
0.8773	High Similarity	NPC321399
0.8773	High Similarity	NPC84571
0.8765	High Similarity	NPC476981
0.8765	High Similarity	NPC236796
0.8765	High Similarity	NPC77679
0.8765	High Similarity	NPC181960
0.8765	High Similarity	NPC262286
0.8765	High Similarity	NPC36852
0.8765	High Similarity	NPC84935
0.8765	High Similarity	NPC469584
0.8765	High Similarity	NPC474055
0.8765	High Similarity	NPC472598
0.8765	High Similarity	NPC190020
0.8765	High Similarity	NPC78225
0.8758	High Similarity	NPC470327
0.8758	High Similarity	NPC37392
0.8758	High Similarity	NPC477503
0.8758	High Similarity	NPC226025
0.8758	High Similarity	NPC286052
0.8758	High Similarity	NPC472909
0.8758	High Similarity	NPC45849
0.8758	High Similarity	NPC200761
0.8757	High Similarity	NPC199533
0.8757	High Similarity	NPC470454
0.875	High Similarity	NPC471982
0.875	High Similarity	NPC260263
0.875	High Similarity	NPC475669
0.875	High Similarity	NPC214901
0.8743	High Similarity	NPC476637
0.8742	High Similarity	NPC338131
0.8742	High Similarity	NPC202595
0.8742	High Similarity	NPC119929
0.8735	High Similarity	NPC39091
0.8735	High Similarity	NPC30027
0.8734	High Similarity	NPC37139
0.8734	High Similarity	NPC5537
0.8727	High Similarity	NPC41301
0.8727	High Similarity	NPC470459
0.8727	High Similarity	NPC189473
0.8727	High Similarity	NPC273959
0.8727	High Similarity	NPC186686
0.8727	High Similarity	NPC23298
0.8727	High Similarity	NPC207690
0.8727	High Similarity	NPC475985
0.8726	High Similarity	NPC473927
0.872	High Similarity	NPC474239
0.872	High Similarity	NPC278427

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 NPC112981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	995
0.2-0.3	1889
0.3-0.4	2585
0.4-0.5	1720
0.5-0.6	978
0.6-0.7	436
0.7-0.8	166
0.8-0.85	24
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9085	High Similarity	NPD5844	Phase 1
0.8896	High Similarity	NPD6232	Discontinued
0.8735	High Similarity	NPD7473	Discontinued
0.858	High Similarity	NPD2801	Approved
0.858	High Similarity	NPD2393	Clinical (unspecified phase)
0.8544	High Similarity	NPD2534	Approved
0.8544	High Similarity	NPD2533	Approved
0.8544	High Similarity	NPD2532	Approved
0.8519	High Similarity	NPD1934	Approved
0.8466	Intermediate Similarity	NPD7819	Suspended
0.8415	Intermediate Similarity	NPD3817	Phase 2
0.8323	Intermediate Similarity	NPD5494	Approved
0.828	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6959	Discontinued
0.8253	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD3882	Suspended
0.8242	Intermediate Similarity	NPD1465	Phase 2
0.8235	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6166	Phase 2
0.8218	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7075	Discontinued
0.8199	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6599	Discontinued
0.8153	Intermediate Similarity	NPD2935	Discontinued
0.815	Intermediate Similarity	NPD7074	Phase 3
0.814	Intermediate Similarity	NPD3818	Discontinued
0.8137	Intermediate Similarity	NPD1511	Approved
0.8133	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7054	Approved
0.8072	Intermediate Similarity	NPD6801	Discontinued
0.8061	Intermediate Similarity	NPD4380	Phase 2
0.8047	Intermediate Similarity	NPD919	Approved
0.8046	Intermediate Similarity	NPD7472	Approved
0.8045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1512	Approved
0.8025	Intermediate Similarity	NPD6799	Approved
0.8012	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD3226	Approved
0.7964	Intermediate Similarity	NPD37	Approved
0.7955	Intermediate Similarity	NPD6559	Discontinued
0.795	Intermediate Similarity	NPD4628	Phase 3
0.7929	Intermediate Similarity	NPD4966	Approved
0.7929	Intermediate Similarity	NPD7768	Phase 2
0.7929	Intermediate Similarity	NPD4967	Phase 2
0.7929	Intermediate Similarity	NPD4965	Approved
0.7925	Intermediate Similarity	NPD1551	Phase 2
0.791	Intermediate Similarity	NPD7808	Phase 3
0.7907	Intermediate Similarity	NPD5711	Approved
0.7907	Intermediate Similarity	NPD5710	Approved
0.7898	Intermediate Similarity	NPD6797	Phase 2
0.7898	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5402	Approved
0.787	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7251	Discontinued
0.7849	Intermediate Similarity	NPD1247	Approved
0.7849	Intermediate Similarity	NPD7199	Phase 2
0.7848	Intermediate Similarity	NPD1607	Approved
0.784	Intermediate Similarity	NPD3750	Approved
0.7836	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD1549	Phase 2
0.7816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD447	Suspended
0.7784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3749	Approved
0.7764	Intermediate Similarity	NPD2346	Discontinued
0.7758	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2799	Discontinued
0.775	Intermediate Similarity	NPD1510	Phase 2
0.7722	Intermediate Similarity	NPD1240	Approved
0.7707	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2796	Approved
0.7673	Intermediate Similarity	NPD230	Phase 1
0.7669	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2800	Approved
0.7669	Intermediate Similarity	NPD1243	Approved
0.7665	Intermediate Similarity	NPD920	Approved
0.7657	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7228	Approved
0.7622	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7390	Discontinued
0.7574	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD8312	Approved
0.756	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5403	Approved
0.7557	Intermediate Similarity	NPD3926	Phase 2
0.7545	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7783	Phase 2
0.7531	Intermediate Similarity	NPD3748	Approved
0.753	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1653	Approved
0.7515	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7485	Intermediate Similarity	NPD6100	Approved
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6099	Approved
0.7474	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7435	Discontinued
0.7446	Intermediate Similarity	NPD8150	Discontinued
0.744	Intermediate Similarity	NPD5401	Approved
0.744	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD8151	Discontinued
0.7421	Intermediate Similarity	NPD3027	Phase 3
0.7401	Intermediate Similarity	NPD7229	Phase 3
0.7391	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4060	Phase 1
0.7391	Intermediate Similarity	NPD943	Approved
0.7391	Intermediate Similarity	NPD1613	Approved
0.7389	Intermediate Similarity	NPD1203	Approved
0.7382	Intermediate Similarity	NPD6781	Approved
0.7382	Intermediate Similarity	NPD6778	Approved
0.7382	Intermediate Similarity	NPD6779	Approved
0.7382	Intermediate Similarity	NPD6776	Approved
0.7382	Intermediate Similarity	NPD6780	Approved
0.7382	Intermediate Similarity	NPD6777	Approved
0.7382	Intermediate Similarity	NPD6782	Approved
0.7378	Intermediate Similarity	NPD5406	Approved
0.7378	Intermediate Similarity	NPD5405	Approved
0.7378	Intermediate Similarity	NPD5408	Approved
0.7378	Intermediate Similarity	NPD5404	Approved
0.736	Intermediate Similarity	NPD5242	Approved
0.7358	Intermediate Similarity	NPD6832	Phase 2
0.7351	Intermediate Similarity	NPD8434	Phase 2
0.7346	Intermediate Similarity	NPD1933	Approved
0.7346	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8127	Discontinued
0.7337	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3751	Discontinued
0.7322	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4625	Phase 3
0.7303	Intermediate Similarity	NPD3787	Discontinued
0.7301	Intermediate Similarity	NPD6651	Approved
0.7296	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6273	Approved
0.7294	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4476	Approved
0.7273	Intermediate Similarity	NPD4477	Approved
0.7268	Intermediate Similarity	NPD7698	Approved
0.7268	Intermediate Similarity	NPD7696	Phase 3
0.7268	Intermediate Similarity	NPD7697	Approved
0.7268	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD2313	Discontinued
0.7262	Intermediate Similarity	NPD6190	Approved
0.725	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7177	Discontinued
0.7231	Intermediate Similarity	NPD7871	Phase 2
0.7231	Intermediate Similarity	NPD7870	Phase 2
0.7222	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7874	Approved
0.7215	Intermediate Similarity	NPD1283	Approved
0.7212	Intermediate Similarity	NPD4308	Phase 3
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7202	Intermediate Similarity	NPD7003	Approved
0.7197	Intermediate Similarity	NPD1608	Approved
0.7197	Intermediate Similarity	NPD9717	Approved
0.7178	Intermediate Similarity	NPD2979	Phase 3
0.7174	Intermediate Similarity	NPD7038	Approved
0.7174	Intermediate Similarity	NPD7039	Approved
0.717	Intermediate Similarity	NPD2797	Approved
0.7169	Intermediate Similarity	NPD2438	Suspended
0.716	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3268	Approved
0.7159	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.7134	Intermediate Similarity	NPD422	Phase 1
0.7134	Intermediate Similarity	NPD1611	Approved
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7126	Intermediate Similarity	NPD2344	Approved
0.7121	Intermediate Similarity	NPD7701	Phase 2
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.7115	Intermediate Similarity	NPD4626	Approved
0.7101	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4110	Phase 3
0.7086	Intermediate Similarity	NPD6386	Approved
0.7086	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6385	Approved
0.7081	Intermediate Similarity	NPD7685	Pre-registration
0.7062	Intermediate Similarity	NPD4288	Approved
0.7059	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7985	Registered
0.7051	Intermediate Similarity	NPD5691	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