NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	502.29
Volume:	524.263
LogP:	5.171
LogD:	4.22
LogS:	-4.09
# Rotatable Bonds:	9
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	4.443
Fsp3:	0.724
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.966
MDCK Permeability:	2.4120547095662914e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.348

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	95.40167999267578%
Volume Distribution (VD):	0.906
Pgp-substrate:	3.1533844470977783%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.84
CYP2C19-inhibitor:	0.227
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.341
CYP2C9-substrate:	0.777
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.548
CYP3A4-substrate:	0.39

ADMET: Excretion

Clearance (CL):	6.871
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.347
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.377
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.257
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.19
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC477672

Natural Product ID:	NPC477672
*Common Name:**	butyl 3-[(5aS,8R,9R,9aR)-8-(2-hydroxypropan-2-yl)-11-methoxy-4,5a,9-trimethyl-1-oxo-3,6,7,8,9a,10-hexahydro-[2]benzofuro[5,6-b]chromen-9-yl]propanoate
IUPAC Name:	butyl 3-[(5aS,8R,9R,9aR)-8-(2-hydroxypropan-2-yl)-11-methoxy-4,5a,9-trimethyl-1-oxo-3,6,7,8,9a,10-hexahydro-[2]benzofuro[5,6-b]chromen-9-yl]propanoate
Synonyms:
Standard InCHIKey:	VZKSJYFCTRVSHA-KMQZGOFYSA-N
Standard InCHI:	InChI=1S/C29H42O7/c1-8-9-14-34-22(30)11-12-28(5)20(27(3,4)32)10-13-29(6)21(28)15-18-24(36-29)17(2)19-16-35-26(31)23(19)25(18)33-7/h20-21,32H,8-16H2,1-7H3/t20-,21+,28+,29-/m0/s1
SMILES:	CCCCOC(=O)CC[C@@]1([C@@H](CC[C@]2([C@@H]1CC3=C(O2)C(=C4COC(=O)C4=C3OC)C)C)C(C)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118706608
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	Lazurnaya Bay, the Sea of Japan	n.a.	PMID[24852445]
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	isolated from superficial mycobiota of the brown alga Sargassum miyabei (Lazurnaya Bay, the Sea of Japan)	n.a.	PMID[24852445]
NPO33623	Penicillium lividum	Species	Aspergillaceae	Eukaryota	n.a.	Lazurnaya Bay, the Sea of Japan	n.a.	PMID[24852445]
NPO33623	Penicillium lividum	Species	Aspergillaceae	Eukaryota	n.a.	isolated from superficial mycobiota of the brown alga Sargassum miyabei (Lazurnaya Bay, the Sea of Japan)	n.a.	PMID[24852445]
NPO29375	Penicillium thomii	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
IC50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	34	%	PMID[24852445]
NPT2	Others	Unspecified		IC50	=	100	nM	PMID[24852445]

☑ 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 NPC477672 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	351
0.1-0.2	1585
0.2-0.3	3295
0.3-0.4	6895
0.4-0.5	11035
0.5-0.6	5993
0.6-0.7	6323
0.7-0.8	6537
0.8-0.85	597
0.85-0.9	73
0.9-0.95	0
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477673
0.9863	High Similarity	NPC477669
0.9796	High Similarity	NPC477687
0.9796	High Similarity	NPC477671
0.973	High Similarity	NPC477675
0.973	High Similarity	NPC477674
0.9658	High Similarity	NPC477676
0.9057	High Similarity	NPC477670
0.8968	High Similarity	NPC239118
0.8954	High Similarity	NPC472799
0.8926	High Similarity	NPC75694
0.8903	High Similarity	NPC158542
0.8874	High Similarity	NPC470359
0.8868	High Similarity	NPC125465
0.8867	High Similarity	NPC470357
0.8846	High Similarity	NPC4950
0.8839	High Similarity	NPC4547
0.8808	High Similarity	NPC245757
0.8808	High Similarity	NPC8817
0.8808	High Similarity	NPC137296
0.8808	High Similarity	NPC304351
0.8766	High Similarity	NPC271681
0.8766	High Similarity	NPC217447
0.8758	High Similarity	NPC150928
0.8742	High Similarity	NPC100849
0.8726	High Similarity	NPC218818
0.8688	High Similarity	NPC316262
0.8688	High Similarity	NPC314653
0.8679	High Similarity	NPC473022
0.8662	High Similarity	NPC272196
0.8658	High Similarity	NPC469818
0.8645	High Similarity	NPC273483
0.8636	High Similarity	NPC119929
0.8634	High Similarity	NPC472621
0.8608	High Similarity	NPC472617
0.8608	High Similarity	NPC474373
0.8606	High Similarity	NPC472661
0.8599	High Similarity	NPC146211
0.8589	High Similarity	NPC477572
0.8589	High Similarity	NPC477573
0.8589	High Similarity	NPC477571
0.8581	High Similarity	NPC478148
0.8581	High Similarity	NPC473131
0.8581	High Similarity	NPC470675
0.858	High Similarity	NPC472622
0.8571	High Similarity	NPC102372
0.8571	High Similarity	NPC233267
0.8571	High Similarity	NPC472599
0.8571	High Similarity	NPC291049
0.8571	High Similarity	NPC156967
0.8553	High Similarity	NPC470673
0.8553	High Similarity	NPC117716
0.8553	High Similarity	NPC470810
0.8553	High Similarity	NPC470674
0.8545	High Similarity	NPC294149
0.8544	High Similarity	NPC196448
0.8543	High Similarity	NPC472344
0.8537	High Similarity	NPC472620
0.8526	High Similarity	NPC87708
0.8516	High Similarity	NPC158866
0.8516	High Similarity	NPC202595
0.8514	High Similarity	NPC245058
0.8514	High Similarity	NPC470982
0.8514	High Similarity	NPC470983
0.8512	High Similarity	NPC475656
0.8512	High Similarity	NPC475148
0.8509	High Similarity	NPC173587
0.8509	High Similarity	NPC208120
0.8509	High Similarity	NPC29055
0.8506	High Similarity	NPC37139
0.8506	High Similarity	NPC105415
0.8506	High Similarity	NPC472345
0.8494	Intermediate Similarity	NPC312630
0.8494	Intermediate Similarity	NPC324220
0.8477	Intermediate Similarity	NPC111201
0.8476	Intermediate Similarity	NPC313717
0.8476	Intermediate Similarity	NPC315306
0.8471	Intermediate Similarity	NPC169990
0.8471	Intermediate Similarity	NPC210942
0.8466	Intermediate Similarity	NPC232936
0.8462	Intermediate Similarity	NPC474417
0.8462	Intermediate Similarity	NPC133856
0.8462	Intermediate Similarity	NPC149526
0.8462	Intermediate Similarity	NPC72958
0.8462	Intermediate Similarity	NPC232645
0.8457	Intermediate Similarity	NPC146584
0.8457	Intermediate Similarity	NPC21016
0.8452	Intermediate Similarity	NPC471114
0.8447	Intermediate Similarity	NPC475106
0.8442	Intermediate Similarity	NPC474108
0.8442	Intermediate Similarity	NPC125801
0.8442	Intermediate Similarity	NPC177995
0.8438	Intermediate Similarity	NPC143050
0.8438	Intermediate Similarity	NPC313368
0.8438	Intermediate Similarity	NPC472618
0.8438	Intermediate Similarity	NPC470358
0.8431	Intermediate Similarity	NPC206212
0.8431	Intermediate Similarity	NPC71184
0.8418	Intermediate Similarity	NPC149618
0.8418	Intermediate Similarity	NPC89625
0.8415	Intermediate Similarity	NPC472619
0.8415	Intermediate Similarity	NPC473202
0.8415	Intermediate Similarity	NPC213416
0.8415	Intermediate Similarity	NPC102810
0.8411	Intermediate Similarity	NPC289660
0.8411	Intermediate Similarity	NPC82920
0.8411	Intermediate Similarity	NPC164697
0.8408	Intermediate Similarity	NPC175978
0.8408	Intermediate Similarity	NPC40356
0.8408	Intermediate Similarity	NPC154683
0.8405	Intermediate Similarity	NPC472452
0.8397	Intermediate Similarity	NPC179178
0.8397	Intermediate Similarity	NPC474660
0.8395	Intermediate Similarity	NPC475055
0.8393	Intermediate Similarity	NPC473607
0.8393	Intermediate Similarity	NPC473729
0.8387	Intermediate Similarity	NPC211625
0.8387	Intermediate Similarity	NPC145467
0.8385	Intermediate Similarity	NPC117985
0.8377	Intermediate Similarity	NPC473927
0.8377	Intermediate Similarity	NPC260946
0.8377	Intermediate Similarity	NPC473135
0.8377	Intermediate Similarity	NPC237208
0.8377	Intermediate Similarity	NPC470676
0.8377	Intermediate Similarity	NPC225173
0.8377	Intermediate Similarity	NPC286038
0.8377	Intermediate Similarity	NPC473132
0.8377	Intermediate Similarity	NPC163846
0.8375	Intermediate Similarity	NPC470339
0.8373	Intermediate Similarity	NPC476311
0.8366	Intermediate Similarity	NPC470553
0.8366	Intermediate Similarity	NPC307895
0.8366	Intermediate Similarity	NPC470932
0.8365	Intermediate Similarity	NPC180924
0.8355	Intermediate Similarity	NPC285659
0.8355	Intermediate Similarity	NPC81337
0.8355	Intermediate Similarity	NPC157497
0.8355	Intermediate Similarity	NPC469579
0.8354	Intermediate Similarity	NPC135522
0.8354	Intermediate Similarity	NPC76647
0.8354	Intermediate Similarity	NPC273248
0.8344	Intermediate Similarity	NPC290671
0.8344	Intermediate Similarity	NPC473286
0.8344	Intermediate Similarity	NPC270913
0.8333	Intermediate Similarity	NPC158338
0.8333	Intermediate Similarity	NPC472402
0.8333	Intermediate Similarity	NPC97028
0.8333	Intermediate Similarity	NPC97029
0.8333	Intermediate Similarity	NPC303989
0.8333	Intermediate Similarity	NPC100985
0.8333	Intermediate Similarity	NPC65589
0.8333	Intermediate Similarity	NPC233978
0.8333	Intermediate Similarity	NPC288036
0.8323	Intermediate Similarity	NPC472055
0.8323	Intermediate Similarity	NPC308200
0.8323	Intermediate Similarity	NPC66991
0.8323	Intermediate Similarity	NPC162248
0.8323	Intermediate Similarity	NPC47623
0.8313	Intermediate Similarity	NPC164110
0.8313	Intermediate Similarity	NPC123153
0.8313	Intermediate Similarity	NPC263483
0.8313	Intermediate Similarity	NPC246647
0.8313	Intermediate Similarity	NPC118128
0.8313	Intermediate Similarity	NPC212967
0.8313	Intermediate Similarity	NPC96342
0.8312	Intermediate Similarity	NPC473692
0.8312	Intermediate Similarity	NPC470554
0.8312	Intermediate Similarity	NPC288910
0.8312	Intermediate Similarity	NPC133060
0.8312	Intermediate Similarity	NPC29577
0.8312	Intermediate Similarity	NPC118059
0.8312	Intermediate Similarity	NPC134621
0.8311	Intermediate Similarity	NPC475645
0.8302	Intermediate Similarity	NPC469934
0.8301	Intermediate Similarity	NPC112829
0.8301	Intermediate Similarity	NPC226942
0.8301	Intermediate Similarity	NPC96791
0.8301	Intermediate Similarity	NPC470636
0.8301	Intermediate Similarity	NPC159721
0.8301	Intermediate Similarity	NPC470556
0.8291	Intermediate Similarity	NPC473770
0.8291	Intermediate Similarity	NPC475131
0.8291	Intermediate Similarity	NPC161778
0.8291	Intermediate Similarity	NPC167903
0.8291	Intermediate Similarity	NPC477690
0.8291	Intermediate Similarity	NPC473509
0.8289	Intermediate Similarity	NPC90411
0.8288	Intermediate Similarity	NPC296158
0.8282	Intermediate Similarity	NPC478044
0.828	Intermediate Similarity	NPC327059
0.828	Intermediate Similarity	NPC476509
0.828	Intermediate Similarity	NPC470107
0.828	Intermediate Similarity	NPC321387
0.828	Intermediate Similarity	NPC29777
0.828	Intermediate Similarity	NPC473466
0.828	Intermediate Similarity	NPC321896
0.828	Intermediate Similarity	NPC471115
0.828	Intermediate Similarity	NPC470908
0.828	Intermediate Similarity	NPC476185
0.828	Intermediate Similarity	NPC227122

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 NPC477672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	1025
0.2-0.3	1948
0.3-0.4	2587
0.4-0.5	1922
0.5-0.6	894
0.6-0.7	342
0.7-0.8	113
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8926	High Similarity	NPD2532	Approved
0.8926	High Similarity	NPD2533	Approved
0.8926	High Similarity	NPD2534	Approved
0.859	High Similarity	NPD7819	Suspended
0.8344	Intermediate Similarity	NPD2800	Approved
0.8333	Intermediate Similarity	NPD5711	Approved
0.8333	Intermediate Similarity	NPD5710	Approved
0.816	Intermediate Similarity	NPD6959	Discontinued
0.8072	Intermediate Similarity	NPD7473	Discontinued
0.8067	Intermediate Similarity	NPD6651	Approved
0.8052	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7974	Intermediate Similarity	NPD2346	Discontinued
0.7937	Intermediate Similarity	NPD6599	Discontinued
0.7908	Intermediate Similarity	NPD6099	Approved
0.7908	Intermediate Similarity	NPD6100	Approved
0.7901	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7411	Suspended
0.7879	Intermediate Similarity	NPD5494	Approved
0.787	Intermediate Similarity	NPD5844	Phase 1
0.7866	Intermediate Similarity	NPD3749	Approved
0.7866	Intermediate Similarity	NPD7075	Discontinued
0.7853	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7229	Phase 3
0.7764	Intermediate Similarity	NPD3226	Approved
0.775	Intermediate Similarity	NPD920	Approved
0.7697	Intermediate Similarity	NPD7768	Phase 2
0.7636	Intermediate Similarity	NPD3817	Phase 2
0.763	Intermediate Similarity	NPD6559	Discontinued
0.7628	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1934	Approved
0.7622	Intermediate Similarity	NPD6801	Discontinued
0.759	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1549	Phase 2
0.7566	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2796	Approved
0.7562	Intermediate Similarity	NPD6799	Approved
0.7532	Intermediate Similarity	NPD1243	Approved
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3882	Suspended
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7484	Intermediate Similarity	NPD3750	Approved
0.747	Intermediate Similarity	NPD1465	Phase 2
0.747	Intermediate Similarity	NPD2801	Approved
0.7452	Intermediate Similarity	NPD1551	Phase 2
0.7452	Intermediate Similarity	NPD2935	Discontinued
0.7451	Intermediate Similarity	NPD7985	Registered
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5124	Phase 1
0.7416	Intermediate Similarity	NPD8434	Phase 2
0.741	Intermediate Similarity	NPD37	Approved
0.7399	Intermediate Similarity	NPD3818	Discontinued
0.7391	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1510	Phase 2
0.7389	Intermediate Similarity	NPD3748	Approved
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7372	Intermediate Similarity	NPD1607	Approved
0.7365	Intermediate Similarity	NPD5760	Phase 2
0.7365	Intermediate Similarity	NPD5761	Phase 2
0.7362	Intermediate Similarity	NPD6273	Approved
0.7356	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7346	Intermediate Similarity	NPD1511	Approved
0.7345	Intermediate Similarity	NPD8312	Approved
0.7345	Intermediate Similarity	NPD8313	Approved
0.7338	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2313	Discontinued
0.7337	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7074	Phase 3
0.731	Intermediate Similarity	NPD7199	Phase 2
0.7294	Intermediate Similarity	NPD919	Approved
0.7294	Intermediate Similarity	NPD6234	Discontinued
0.7283	Intermediate Similarity	NPD6166	Phase 2
0.7283	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7003	Approved
0.7257	Intermediate Similarity	NPD7054	Approved
0.7256	Intermediate Similarity	NPD1512	Approved
0.7246	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1240	Approved
0.7239	Intermediate Similarity	NPD7390	Discontinued
0.7229	Intermediate Similarity	NPD7458	Discontinued
0.7225	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5402	Approved
0.7216	Intermediate Similarity	NPD7472	Approved
0.7211	Intermediate Similarity	NPD7644	Approved
0.72	Intermediate Similarity	NPD7228	Approved
0.7191	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5953	Discontinued
0.7161	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7125	Intermediate Similarity	NPD5405	Approved
0.7125	Intermediate Similarity	NPD5408	Approved
0.7125	Intermediate Similarity	NPD5404	Approved
0.7125	Intermediate Similarity	NPD5406	Approved
0.711	Intermediate Similarity	NPD1247	Approved
0.7102	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6832	Phase 2
0.7095	Intermediate Similarity	NPD7808	Phase 3
0.7079	Intermediate Similarity	NPD6797	Phase 2
0.7079	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8032	Phase 2
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7062	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7783	Phase 2
0.7059	Intermediate Similarity	NPD6696	Suspended
0.7059	Intermediate Similarity	NPD1283	Approved
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7049	Intermediate Similarity	NPD4287	Approved
0.7049	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8151	Discontinued
0.7039	Intermediate Similarity	NPD7240	Approved
0.7039	Intermediate Similarity	NPD1608	Approved
0.7029	Intermediate Similarity	NPD3926	Phase 2
0.7027	Intermediate Similarity	NPD7340	Approved
0.7025	Intermediate Similarity	NPD2979	Phase 3
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD5403	Approved
0.7006	Intermediate Similarity	NPD7177	Discontinued
0.7006	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8366	Approved
0.6994	Remote Similarity	NPD6674	Discontinued
0.6993	Remote Similarity	NPD4749	Approved
0.6989	Remote Similarity	NPD2403	Approved
0.6988	Remote Similarity	NPD5401	Approved
0.6981	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD230	Phase 1
0.6975	Remote Similarity	NPD2344	Approved
0.6975	Remote Similarity	NPD6002	Phase 3
0.6975	Remote Similarity	NPD6004	Phase 3
0.6975	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6005	Phase 3
0.6971	Remote Similarity	NPD3787	Discontinued
0.6968	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4308	Phase 3
0.6954	Remote Similarity	NPD1778	Approved
0.6931	Remote Similarity	NPD8285	Discontinued
0.6918	Remote Similarity	NPD4140	Approved
0.691	Remote Similarity	NPD3751	Discontinued
0.6903	Remote Similarity	NPD2797	Approved
0.6899	Remote Similarity	NPD411	Approved
0.6899	Remote Similarity	NPD3268	Approved
0.6895	Remote Similarity	NPD6781	Approved
0.6895	Remote Similarity	NPD6782	Approved
0.6895	Remote Similarity	NPD6780	Approved
0.6895	Remote Similarity	NPD6778	Approved
0.6895	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6779	Approved
0.6895	Remote Similarity	NPD6776	Approved
0.6895	Remote Similarity	NPD6777	Approved
0.6887	Remote Similarity	NPD5691	Approved
0.6886	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4908	Phase 1
0.6875	Remote Similarity	NPD447	Suspended
0.6875	Remote Similarity	NPD7697	Approved
0.6875	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD7698	Approved
0.6875	Remote Similarity	NPD7696	Phase 3
0.6871	Remote Similarity	NPD1471	Phase 3
0.6863	Remote Similarity	NPD8491	Approved
0.6863	Remote Similarity	NPD1281	Approved
0.6842	Remote Similarity	NPD4626	Approved
0.6842	Remote Similarity	NPD17	Approved
0.6842	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7870	Phase 2
0.6839	Remote Similarity	NPD7871	Phase 2
0.6837	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7874	Approved
0.6826	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1398	Phase 1
0.6821	Remote Similarity	NPD4288	Approved
0.6821	Remote Similarity	NPD5353	Approved
0.6818	Remote Similarity	NPD9717	Approved
0.6813	Remote Similarity	NPD4307	Phase 2

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