NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	462.23
Volume:	463.87
LogP:	2.967
LogD:	1.284
LogS:	-3.496
# Rotatable Bonds:	5
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	4.651
Fsp3:	0.68
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:	-5.527
MDCK Permeability:	8.224962584790774e-06
Pgp-inhibitor:	0.017
Pgp-substrate:	0.375
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211
Plasma Protein Binding (PPB):	81.0309829711914%
Volume Distribution (VD):	0.398
Pgp-substrate:	10.981432914733887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.744
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.623
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	6.307
Half-life (T1/2):	0.776

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.551
AMES Toxicity:	0.494
Rat Oral Acute Toxicity:	0.572
Maximum Recommended Daily Dose:	0.208
Skin Sensitization:	0.215
Carcinogencity:	0.607
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.613

Download Data

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

Natural Product: NPC477671

Natural Product ID:	NPC477671
*Common Name:**	3-[(5aS,7R,8S,9S,9aR)-7-hydroxy-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]propanoic acid
IUPAC Name:	3-[(5aS,7R,8S,9S,9aR)-7-hydroxy-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]propanoic acid
Synonyms:
Standard InCHIKey:	NNOMPFCNQCRAIO-IIYTZCCASA-N
Standard InCHI:	InChI=1S/C25H34O8/c1-12-14-11-32-22(29)18(14)20(31-6)13-9-16-24(4,8-7-17(27)28)21(23(2,3)30)15(26)10-25(16,5)33-19(12)13/h15-16,21,26,30H,7-11H2,1-6H3,(H,27,28)/t15-,16-,21+,24+,25+/m1/s1
SMILES:	CC1=C2COC(=O)C2=C(C3=C1O[C@]4(C[C@H]([C@H]([C@@]([C@H]4C3)(C)CCC(=O)O)C(C)(C)O)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	92854697
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	3

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	<	10000	nM	PMID[24852445]
NPT2	Others	Unspecified		IC50	<	10000	nM	PMID[24852445]
NPT2	Others	Unspecified		IC50	=	1000	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 NPC477671 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	353
0.1-0.2	1526
0.2-0.3	3224
0.3-0.4	6497
0.4-0.5	10988
0.5-0.6	6494
0.6-0.7	6093
0.7-0.8	6863
0.8-0.85	581
0.85-0.9	63
0.9-0.95	5
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477687
0.9799	High Similarity	NPC477675
0.9799	High Similarity	NPC477674
0.9796	High Similarity	NPC477673
0.9796	High Similarity	NPC477672
0.9664	High Similarity	NPC477669
0.9463	High Similarity	NPC477676
0.9245	High Similarity	NPC477670
0.9073	High Similarity	NPC470359
0.894	High Similarity	NPC470357
0.8917	High Similarity	NPC4950
0.8917	High Similarity	NPC239118
0.8882	High Similarity	NPC8817
0.882	High Similarity	NPC125465
0.8812	High Similarity	NPC100849
0.8797	High Similarity	NPC218818
0.8782	High Similarity	NPC472799
0.875	High Similarity	NPC75694
0.8734	High Similarity	NPC158542
0.8727	High Similarity	NPC294149
0.8704	High Similarity	NPC472621
0.8701	High Similarity	NPC472345
0.8679	High Similarity	NPC472617
0.8675	High Similarity	NPC324220
0.8675	High Similarity	NPC312630
0.8671	High Similarity	NPC4547
0.8659	High Similarity	NPC477572
0.8659	High Similarity	NPC477573
0.8659	High Similarity	NPC477571
0.8654	High Similarity	NPC473131
0.8654	High Similarity	NPC470675
0.865	High Similarity	NPC472622
0.8642	High Similarity	NPC316262
0.8642	High Similarity	NPC314653
0.8636	High Similarity	NPC304351
0.8636	High Similarity	NPC137296
0.8636	High Similarity	NPC245757
0.8634	High Similarity	NPC473022
0.8625	High Similarity	NPC470358
0.8606	High Similarity	NPC472620
0.8599	High Similarity	NPC271681
0.8599	High Similarity	NPC217447
0.8599	High Similarity	NPC273483
0.8598	High Similarity	NPC102810
0.8598	High Similarity	NPC473202
0.859	High Similarity	NPC150928
0.858	High Similarity	NPC475656
0.858	High Similarity	NPC475148
0.8571	High Similarity	NPC473729
0.8571	High Similarity	NPC473607
0.8563	High Similarity	NPC472661
0.8554	High Similarity	NPC476311
0.8553	High Similarity	NPC146211
0.8545	High Similarity	NPC313717
0.8545	High Similarity	NPC315306
0.8528	High Similarity	NPC21016
0.8528	High Similarity	NPC102372
0.8528	High Similarity	NPC146584
0.8523	High Similarity	NPC156967
0.8523	High Similarity	NPC472599
0.8516	High Similarity	NPC474108
0.8516	High Similarity	NPC177995
0.8509	High Similarity	NPC470810
0.8509	High Similarity	NPC472055
0.8509	High Similarity	NPC472618
0.85	High Similarity	NPC196448
0.85	High Similarity	NPC272196
0.8497	Intermediate Similarity	NPC472344
0.8487	Intermediate Similarity	NPC469818
0.8485	Intermediate Similarity	NPC213416
0.8485	Intermediate Similarity	NPC472619
0.8481	Intermediate Similarity	NPC475131
0.8481	Intermediate Similarity	NPC473509
0.8481	Intermediate Similarity	NPC87708
0.8481	Intermediate Similarity	NPC473770
0.8471	Intermediate Similarity	NPC119929
0.8471	Intermediate Similarity	NPC202595
0.8471	Intermediate Similarity	NPC179178
0.8467	Intermediate Similarity	NPC245058
0.8466	Intermediate Similarity	NPC173587
0.8466	Intermediate Similarity	NPC208120
0.8466	Intermediate Similarity	NPC478044
0.8457	Intermediate Similarity	NPC117985
0.8452	Intermediate Similarity	NPC286038
0.8447	Intermediate Similarity	NPC470339
0.8447	Intermediate Similarity	NPC474373
0.8442	Intermediate Similarity	NPC112749
0.8431	Intermediate Similarity	NPC469579
0.8431	Intermediate Similarity	NPC157497
0.8431	Intermediate Similarity	NPC81337
0.8431	Intermediate Similarity	NPC285659
0.8424	Intermediate Similarity	NPC232936
0.8418	Intermediate Similarity	NPC72958
0.8418	Intermediate Similarity	NPC478148
0.8418	Intermediate Similarity	NPC232645
0.8418	Intermediate Similarity	NPC133856
0.8408	Intermediate Similarity	NPC291049
0.8408	Intermediate Similarity	NPC233267
0.8402	Intermediate Similarity	NPC476199
0.8402	Intermediate Similarity	NPC233978
0.8402	Intermediate Similarity	NPC476210
0.8397	Intermediate Similarity	NPC66991
0.8395	Intermediate Similarity	NPC313368
0.8395	Intermediate Similarity	NPC143050
0.8393	Intermediate Similarity	NPC162248
0.8387	Intermediate Similarity	NPC470674
0.8387	Intermediate Similarity	NPC118059
0.8387	Intermediate Similarity	NPC117716
0.8387	Intermediate Similarity	NPC470673
0.8387	Intermediate Similarity	NPC133060
0.8387	Intermediate Similarity	NPC288910
0.8387	Intermediate Similarity	NPC470554
0.8375	Intermediate Similarity	NPC89625
0.8375	Intermediate Similarity	NPC149618
0.8373	Intermediate Similarity	NPC191653
0.8365	Intermediate Similarity	NPC167903
0.8364	Intermediate Similarity	NPC472452
0.8354	Intermediate Similarity	NPC475055
0.8354	Intermediate Similarity	NPC321387
0.8354	Intermediate Similarity	NPC475460
0.8354	Intermediate Similarity	NPC327059
0.8354	Intermediate Similarity	NPC476509
0.8354	Intermediate Similarity	NPC158866
0.8354	Intermediate Similarity	NPC470908
0.8354	Intermediate Similarity	NPC29055
0.8344	Intermediate Similarity	NPC470982
0.8344	Intermediate Similarity	NPC470983
0.8344	Intermediate Similarity	NPC105415
0.8344	Intermediate Similarity	NPC211625
0.8344	Intermediate Similarity	NPC37139
0.8343	Intermediate Similarity	NPC227275
0.8343	Intermediate Similarity	NPC475233
0.8333	Intermediate Similarity	NPC186113
0.8333	Intermediate Similarity	NPC279732
0.8333	Intermediate Similarity	NPC478042
0.8333	Intermediate Similarity	NPC472299
0.8333	Intermediate Similarity	NPC98776
0.8333	Intermediate Similarity	NPC470910
0.8323	Intermediate Similarity	NPC241874
0.8323	Intermediate Similarity	NPC470932
0.8323	Intermediate Similarity	NPC470553
0.8323	Intermediate Similarity	NPC17219
0.8323	Intermediate Similarity	NPC184738
0.8323	Intermediate Similarity	NPC470909
0.8323	Intermediate Similarity	NPC33653
0.8323	Intermediate Similarity	NPC474939
0.8323	Intermediate Similarity	NPC298778
0.8323	Intermediate Similarity	NPC96216
0.8323	Intermediate Similarity	NPC307895
0.8323	Intermediate Similarity	NPC164427
0.8314	Intermediate Similarity	NPC472662
0.8314	Intermediate Similarity	NPC472663
0.8313	Intermediate Similarity	NPC135522
0.8313	Intermediate Similarity	NPC471695
0.8313	Intermediate Similarity	NPC225419
0.8313	Intermediate Similarity	NPC473094
0.8313	Intermediate Similarity	NPC76647
0.8313	Intermediate Similarity	NPC210942
0.8313	Intermediate Similarity	NPC169990
0.8312	Intermediate Similarity	NPC111201
0.8304	Intermediate Similarity	NPC208069
0.8303	Intermediate Similarity	NPC473286
0.8303	Intermediate Similarity	NPC473908
0.8302	Intermediate Similarity	NPC215921
0.8302	Intermediate Similarity	NPC474417
0.8302	Intermediate Similarity	NPC149526
0.8302	Intermediate Similarity	NPC200773
0.8302	Intermediate Similarity	NPC290671
0.8302	Intermediate Similarity	NPC70016
0.8302	Intermediate Similarity	NPC48671
0.8302	Intermediate Similarity	NPC240768
0.8293	Intermediate Similarity	NPC15374
0.8293	Intermediate Similarity	NPC472402
0.8293	Intermediate Similarity	NPC473961
0.8293	Intermediate Similarity	NPC475106
0.8291	Intermediate Similarity	NPC270160
0.8291	Intermediate Similarity	NPC471114
0.8291	Intermediate Similarity	NPC237440
0.8284	Intermediate Similarity	NPC474345
0.8284	Intermediate Similarity	NPC63105
0.8284	Intermediate Similarity	NPC68381
0.8284	Intermediate Similarity	NPC470454
0.8284	Intermediate Similarity	NPC199533
0.828	Intermediate Similarity	NPC285748
0.828	Intermediate Similarity	NPC125801
0.8274	Intermediate Similarity	NPC118128
0.8272	Intermediate Similarity	NPC123153
0.8272	Intermediate Similarity	NPC281137
0.8272	Intermediate Similarity	NPC263483
0.8272	Intermediate Similarity	NPC282390
0.8269	Intermediate Similarity	NPC71184
0.8269	Intermediate Similarity	NPC206212
0.8263	Intermediate Similarity	NPC473095
0.8263	Intermediate Similarity	NPC473096
0.8261	Intermediate Similarity	NPC175192
0.8261	Intermediate Similarity	NPC68727
0.8258	Intermediate Similarity	NPC112829
0.8258	Intermediate Similarity	NPC51106
0.8258	Intermediate Similarity	NPC294432
0.8258	Intermediate Similarity	NPC159721

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 NPC477671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	1037
0.2-0.3	2006
0.3-0.4	2528
0.4-0.5	1936
0.5-0.6	874
0.6-0.7	338
0.7-0.8	118
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD2532	Approved
0.875	High Similarity	NPD2533	Approved
0.875	High Similarity	NPD2534	Approved
0.8544	High Similarity	NPD7819	Suspended
0.8232	Intermediate Similarity	NPD6959	Discontinued
0.8182	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD5711	Approved
0.8182	Intermediate Similarity	NPD5710	Approved
0.8036	Intermediate Similarity	NPD7473	Discontinued
0.8026	Intermediate Similarity	NPD6651	Approved
0.8	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6232	Discontinued
0.7941	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD7075	Discontinued
0.7927	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7411	Suspended
0.7844	Intermediate Similarity	NPD5494	Approved
0.7821	Intermediate Similarity	NPD2346	Discontinued
0.7805	Intermediate Similarity	NPD6801	Discontinued
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD6599	Discontinued
0.7756	Intermediate Similarity	NPD6099	Approved
0.7756	Intermediate Similarity	NPD6100	Approved
0.773	Intermediate Similarity	NPD3226	Approved
0.7725	Intermediate Similarity	NPD3749	Approved
0.7702	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4380	Phase 2
0.7665	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7229	Phase 3
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD920	Approved
0.7605	Intermediate Similarity	NPD3817	Phase 2
0.7595	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD37	Approved
0.759	Intermediate Similarity	NPD1934	Approved
0.7584	Intermediate Similarity	NPD8434	Phase 2
0.7574	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3818	Discontinued
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.756	Intermediate Similarity	NPD7768	Phase 2
0.756	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD4965	Approved
0.756	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1549	Phase 2
0.7532	Intermediate Similarity	NPD2796	Approved
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7074	Phase 3
0.7457	Intermediate Similarity	NPD6166	Phase 2
0.7457	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1465	Phase 2
0.744	Intermediate Similarity	NPD5760	Phase 2
0.744	Intermediate Similarity	NPD5761	Phase 2
0.7439	Intermediate Similarity	NPD6273	Approved
0.7429	Intermediate Similarity	NPD7054	Approved
0.7423	Intermediate Similarity	NPD6799	Approved
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7985	Registered
0.7396	Intermediate Similarity	NPD5402	Approved
0.7391	Intermediate Similarity	NPD1243	Approved
0.7386	Intermediate Similarity	NPD7472	Approved
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7378	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7228	Approved
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.736	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2799	Discontinued
0.7353	Intermediate Similarity	NPD3882	Suspended
0.7346	Intermediate Similarity	NPD3750	Approved
0.7346	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2801	Approved
0.7312	Intermediate Similarity	NPD1551	Phase 2
0.7312	Intermediate Similarity	NPD2935	Discontinued
0.7308	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7251	Discontinued
0.7293	Intermediate Similarity	NPD8150	Discontinued
0.7284	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7808	Phase 3
0.7256	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1510	Phase 2
0.725	Intermediate Similarity	NPD3748	Approved
0.725	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6797	Phase 2
0.7247	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1607	Approved
0.7232	Intermediate Similarity	NPD7286	Phase 2
0.7219	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1511	Approved
0.7212	Intermediate Similarity	NPD7390	Discontinued
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7207	Intermediate Similarity	NPD7240	Approved
0.7202	Intermediate Similarity	NPD8151	Discontinued
0.72	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2313	Discontinued
0.7186	Intermediate Similarity	NPD5403	Approved
0.7184	Intermediate Similarity	NPD8127	Discontinued
0.7169	Intermediate Similarity	NPD5401	Approved
0.7168	Intermediate Similarity	NPD919	Approved
0.7167	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5953	Discontinued
0.715	Intermediate Similarity	NPD8366	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7003	Approved
0.7126	Intermediate Similarity	NPD1512	Approved
0.712	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1240	Approved
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7079	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6674	Discontinued
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7067	Intermediate Similarity	NPD7644	Approved
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7053	Intermediate Similarity	NPD6778	Approved
0.7053	Intermediate Similarity	NPD6781	Approved
0.7053	Intermediate Similarity	NPD6780	Approved
0.7053	Intermediate Similarity	NPD6777	Approved
0.7053	Intermediate Similarity	NPD6782	Approved
0.7053	Intermediate Similarity	NPD6776	Approved
0.7053	Intermediate Similarity	NPD6779	Approved
0.7045	Intermediate Similarity	NPD3787	Discontinued
0.7031	Intermediate Similarity	NPD7696	Phase 3
0.7031	Intermediate Similarity	NPD7698	Approved
0.7031	Intermediate Similarity	NPD7697	Approved
0.703	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4625	Phase 3
0.701	Intermediate Similarity	NPD8491	Approved
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD8285	Discontinued
0.7	Intermediate Similarity	NPD4140	Approved
0.6995	Remote Similarity	NPD7870	Phase 2
0.6995	Remote Similarity	NPD7871	Phase 2
0.6994	Remote Similarity	NPD5404	Approved
0.6994	Remote Similarity	NPD5406	Approved
0.6994	Remote Similarity	NPD5405	Approved
0.6994	Remote Similarity	NPD5408	Approved
0.699	Remote Similarity	NPD7874	Approved
0.699	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1247	Approved
0.6983	Remote Similarity	NPD3751	Discontinued
0.6982	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8032	Phase 2
0.6936	Remote Similarity	NPD8455	Phase 2
0.6935	Remote Similarity	NPD4287	Approved
0.6923	Remote Similarity	NPD1283	Approved
0.6923	Remote Similarity	NPD6696	Suspended
0.6907	Remote Similarity	NPD8320	Phase 1
0.6907	Remote Similarity	NPD8319	Approved
0.6903	Remote Similarity	NPD1608	Approved
0.6894	Remote Similarity	NPD2979	Phase 3
0.6893	Remote Similarity	NPD8469	Approved
0.6891	Remote Similarity	NPD6823	Phase 2
0.689	Remote Similarity	NPD2438	Suspended
0.6889	Remote Similarity	NPD7177	Discontinued
0.6888	Remote Similarity	NPD7701	Phase 2
0.6887	Remote Similarity	NPD7340	Approved
0.6878	Remote Similarity	NPD6534	Approved
0.6878	Remote Similarity	NPD6535	Approved
0.6878	Remote Similarity	NPD4363	Phase 3
0.6878	Remote Similarity	NPD4360	Phase 2
0.6875	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3764	Approved
0.6872	Remote Similarity	NPD2403	Approved
0.6869	Remote Similarity	NPD7801	Approved
0.6867	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7700	Phase 2
0.6859	Remote Similarity	NPD4749	Approved
0.6859	Remote Similarity	NPD7699	Phase 2
0.6852	Remote Similarity	NPD6355	Discontinued
0.6852	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD230	Phase 1
0.685	Remote Similarity	NPD7930	Approved
0.6848	Remote Similarity	NPD2344	Approved
0.6848	Remote Similarity	NPD5763	Approved
0.6848	Remote Similarity	NPD5762	Approved
0.6845	Remote Similarity	NPD7236	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