NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	444.21
Volume:	452.443
LogP:	3.784
LogD:	1.908
LogS:	-3.51
# Rotatable Bonds:	5
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	4.702
Fsp3:	0.6
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:	-5.254
MDCK Permeability:	1.070958751370199e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.371
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	87.64852142333984%
Volume Distribution (VD):	0.686
Pgp-substrate:	8.547160148620605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.875
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	7.321
Half-life (T1/2):	0.679

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.786
Drug-inuced Liver Injury (DILI):	0.644
AMES Toxicity:	0.14
Rat Oral Acute Toxicity:	0.822
Maximum Recommended Daily Dose:	0.337
Skin Sensitization:	0.149
Carcinogencity:	0.267
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.269

Download Data

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

Natural Product: NPC477674

Natural Product ID:	NPC477674
*Common Name:**	3-[(5aS,7R,8S,9R,9aR)-7-hydroxy-11-methoxy-4,5a,9-trimethyl-1-oxo-8-prop-1-en-2-yl-3,6,7,8,9a,10-hexahydro-[2]benzofuro[5,6-b]chromen-9-yl]propanoic acid
IUPAC Name:	3-[(5aS,7R,8S,9R,9aR)-7-hydroxy-11-methoxy-4,5a,9-trimethyl-1-oxo-8-prop-1-en-2-yl-3,6,7,8,9a,10-hexahydro-[2]benzofuro[5,6-b]chromen-9-yl]propanoic acid
Synonyms:
Standard InCHIKey:	DDBYFNVMRYVEDG-FWRBZCNPSA-N
Standard InCHI:	InChI=1S/C25H32O7/c1-12(2)20-16(26)10-25(5)17(24(20,4)8-7-18(27)28)9-14-21(32-25)13(3)15-11-31-23(29)19(15)22(14)30-6/h16-17,20,26H,1,7-11H2,2-6H3,(H,27,28)/t16-,17-,20-,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)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118706610
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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	120	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 NPC477674 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	347
0.1-0.2	1403
0.2-0.3	3010
0.3-0.4	5879
0.4-0.5	10851
0.5-0.6	6986
0.6-0.7	5831
0.7-0.8	7317
0.8-0.85	963
0.85-0.9	94
0.9-0.95	6
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC477669
0.9799	High Similarity	NPC477687
0.9799	High Similarity	NPC477671
0.9733	High Similarity	NPC477675
0.973	High Similarity	NPC477673
0.973	High Similarity	NPC477672
0.94	High Similarity	NPC477676
0.9133	High Similarity	NPC470357
0.9073	High Similarity	NPC8817
0.9068	High Similarity	NPC477670
0.9	High Similarity	NPC125465
0.8994	High Similarity	NPC100849
0.8981	High Similarity	NPC239118
0.8981	High Similarity	NPC4950
0.8968	High Similarity	NPC472799
0.894	High Similarity	NPC75694
0.8889	High Similarity	NPC470359
0.8861	High Similarity	NPC218818
0.8854	High Similarity	NPC4547
0.8824	High Similarity	NPC137296
0.882	High Similarity	NPC314653
0.882	High Similarity	NPC316262
0.8797	High Similarity	NPC158542
0.8782	High Similarity	NPC273483
0.8782	High Similarity	NPC217447
0.8782	High Similarity	NPC271681
0.8774	High Similarity	NPC150928
0.8765	High Similarity	NPC472621
0.8742	High Similarity	NPC472617
0.8735	High Similarity	NPC324220
0.8735	High Similarity	NPC312630
0.872	High Similarity	NPC313717
0.872	High Similarity	NPC477572
0.872	High Similarity	NPC477571
0.872	High Similarity	NPC477573
0.872	High Similarity	NPC315306
0.8718	High Similarity	NPC470675
0.8718	High Similarity	NPC473131
0.8712	High Similarity	NPC472622
0.8696	High Similarity	NPC473022
0.8688	High Similarity	NPC470358
0.8688	High Similarity	NPC470810
0.8684	High Similarity	NPC472344
0.8679	High Similarity	NPC196448
0.8679	High Similarity	NPC272196
0.8675	High Similarity	NPC294149
0.8667	High Similarity	NPC472620
0.8662	High Similarity	NPC87708
0.8659	High Similarity	NPC102810
0.8659	High Similarity	NPC473202
0.8654	High Similarity	NPC119929
0.8654	High Similarity	NPC202595
0.8639	High Similarity	NPC475656
0.8639	High Similarity	NPC475148
0.8636	High Similarity	NPC286038
0.8631	High Similarity	NPC473607
0.8631	High Similarity	NPC473729
0.8625	High Similarity	NPC474373
0.8625	High Similarity	NPC470339
0.8623	High Similarity	NPC472661
0.8618	High Similarity	NPC469579
0.8616	High Similarity	NPC146211
0.8614	High Similarity	NPC476311
0.8599	High Similarity	NPC232645
0.8599	High Similarity	NPC72958
0.8599	High Similarity	NPC478148
0.859	High Similarity	NPC291049
0.859	High Similarity	NPC233267
0.8581	High Similarity	NPC304351
0.8581	High Similarity	NPC66991
0.8581	High Similarity	NPC177995
0.8581	High Similarity	NPC245757
0.8581	High Similarity	NPC474108
0.8571	High Similarity	NPC472055
0.8571	High Similarity	NPC470554
0.8571	High Similarity	NPC472618
0.8571	High Similarity	NPC288910
0.8571	High Similarity	NPC133060
0.8571	High Similarity	NPC313368
0.8571	High Similarity	NPC118059
0.8545	High Similarity	NPC472619
0.8544	High Similarity	NPC167903
0.8535	High Similarity	NPC158866
0.8535	High Similarity	NPC179178
0.8535	High Similarity	NPC470908
0.8526	High Similarity	NPC211625
0.8526	High Similarity	NPC37139
0.8526	High Similarity	NPC105415
0.8526	High Similarity	NPC472345
0.8519	High Similarity	NPC117985
0.8516	High Similarity	NPC470910
0.8509	High Similarity	NPC186113
0.8506	High Similarity	NPC474939
0.8506	High Similarity	NPC470932
0.8506	High Similarity	NPC96216
0.8506	High Similarity	NPC33653
0.8506	High Similarity	NPC184738
0.8506	High Similarity	NPC307895
0.8506	High Similarity	NPC470909
0.8506	High Similarity	NPC470553
0.85	High Similarity	NPC164427
0.8491	Intermediate Similarity	NPC135522
0.8491	Intermediate Similarity	NPC210942
0.8491	Intermediate Similarity	NPC169990
0.8485	Intermediate Similarity	NPC225419
0.8481	Intermediate Similarity	NPC149526
0.8481	Intermediate Similarity	NPC133856
0.8481	Intermediate Similarity	NPC290671
0.8481	Intermediate Similarity	NPC48671
0.8481	Intermediate Similarity	NPC474417
0.8476	Intermediate Similarity	NPC102372
0.8476	Intermediate Similarity	NPC146584
0.8476	Intermediate Similarity	NPC21016
0.8476	Intermediate Similarity	NPC473286
0.8471	Intermediate Similarity	NPC237440
0.8471	Intermediate Similarity	NPC471114
0.8471	Intermediate Similarity	NPC270160
0.8467	Intermediate Similarity	NPC472599
0.8467	Intermediate Similarity	NPC156967
0.8466	Intermediate Similarity	NPC473961
0.8466	Intermediate Similarity	NPC475106
0.8462	Intermediate Similarity	NPC476199
0.8462	Intermediate Similarity	NPC476210
0.8462	Intermediate Similarity	NPC285748
0.8462	Intermediate Similarity	NPC233978
0.8462	Intermediate Similarity	NPC125801
0.8457	Intermediate Similarity	NPC143050
0.8452	Intermediate Similarity	NPC470673
0.8452	Intermediate Similarity	NPC162248
0.8452	Intermediate Similarity	NPC470674
0.8452	Intermediate Similarity	NPC117716
0.8447	Intermediate Similarity	NPC282390
0.8447	Intermediate Similarity	NPC281137
0.8443	Intermediate Similarity	NPC118128
0.8442	Intermediate Similarity	NPC469542
0.8442	Intermediate Similarity	NPC112829
0.8442	Intermediate Similarity	NPC51106
0.8442	Intermediate Similarity	NPC159721
0.8442	Intermediate Similarity	NPC470556
0.8442	Intermediate Similarity	NPC471731
0.8442	Intermediate Similarity	NPC294432
0.8438	Intermediate Similarity	NPC175192
0.8438	Intermediate Similarity	NPC149618
0.8438	Intermediate Similarity	NPC89625
0.8434	Intermediate Similarity	NPC213416
0.8431	Intermediate Similarity	NPC469818
0.8428	Intermediate Similarity	NPC51824
0.8428	Intermediate Similarity	NPC40356
0.8428	Intermediate Similarity	NPC154683
0.8428	Intermediate Similarity	NPC175978
0.8428	Intermediate Similarity	NPC470340
0.8428	Intermediate Similarity	NPC114880
0.8428	Intermediate Similarity	NPC268992
0.8428	Intermediate Similarity	NPC474843
0.8428	Intermediate Similarity	NPC470338
0.8428	Intermediate Similarity	NPC113608
0.8428	Intermediate Similarity	NPC470337
0.8424	Intermediate Similarity	NPC472452
0.8418	Intermediate Similarity	NPC476509
0.8418	Intermediate Similarity	NPC474660
0.8418	Intermediate Similarity	NPC321387
0.8418	Intermediate Similarity	NPC327059
0.8418	Intermediate Similarity	NPC476185
0.8418	Intermediate Similarity	NPC474735
0.8418	Intermediate Similarity	NPC321896
0.8418	Intermediate Similarity	NPC475460
0.8415	Intermediate Similarity	NPC208120
0.8415	Intermediate Similarity	NPC173587
0.8415	Intermediate Similarity	NPC475055
0.8411	Intermediate Similarity	NPC245058
0.8408	Intermediate Similarity	NPC145467
0.8402	Intermediate Similarity	NPC227275
0.8402	Intermediate Similarity	NPC478050
0.8402	Intermediate Similarity	NPC475233
0.8397	Intermediate Similarity	NPC473023
0.8397	Intermediate Similarity	NPC290133
0.8397	Intermediate Similarity	NPC24136
0.8397	Intermediate Similarity	NPC237208
0.8397	Intermediate Similarity	NPC225173
0.8397	Intermediate Similarity	NPC187282
0.8397	Intermediate Similarity	NPC163846
0.8397	Intermediate Similarity	NPC473927
0.8395	Intermediate Similarity	NPC472299
0.8395	Intermediate Similarity	NPC85121
0.8395	Intermediate Similarity	NPC279732
0.8393	Intermediate Similarity	NPC98776
0.8387	Intermediate Similarity	NPC18886
0.8387	Intermediate Similarity	NPC151607
0.8387	Intermediate Similarity	NPC42540
0.8385	Intermediate Similarity	NPC129053
0.8385	Intermediate Similarity	NPC470625
0.8385	Intermediate Similarity	NPC474609
0.8385	Intermediate Similarity	NPC475797
0.8385	Intermediate Similarity	NPC180924
0.8385	Intermediate Similarity	NPC469936
0.8385	Intermediate Similarity	NPC474738
0.8385	Intermediate Similarity	NPC78554
0.8385	Intermediate Similarity	NPC321372
0.8385	Intermediate Similarity	NPC109967
0.8383	Intermediate Similarity	NPC241874

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 NPC477674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	946
0.2-0.3	1852
0.3-0.4	2550
0.4-0.5	1961
0.5-0.6	985
0.6-0.7	383
0.7-0.8	152
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.894	High Similarity	NPD2534	Approved
0.894	High Similarity	NPD2532	Approved
0.894	High Similarity	NPD2533	Approved
0.8608	High Similarity	NPD7819	Suspended
0.8354	Intermediate Similarity	NPD5711	Approved
0.8354	Intermediate Similarity	NPD5710	Approved
0.8247	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD6959	Discontinued
0.8148	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD5844	Phase 1
0.8095	Intermediate Similarity	NPD7473	Discontinued
0.8077	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD2346	Discontinued
0.8	Intermediate Similarity	NPD7075	Discontinued
0.7988	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7947	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6100	Approved
0.7935	Intermediate Similarity	NPD6099	Approved
0.7914	Intermediate Similarity	NPD7411	Suspended
0.7892	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6559	Discontinued
0.7857	Intermediate Similarity	NPD6651	Approved
0.7811	Intermediate Similarity	NPD7229	Phase 3
0.7791	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6801	Discontinued
0.7758	Intermediate Similarity	NPD1934	Approved
0.7744	Intermediate Similarity	NPD4380	Phase 2
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7725	Intermediate Similarity	NPD7768	Phase 2
0.7725	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1549	Phase 2
0.7707	Intermediate Similarity	NPD2796	Approved
0.7683	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5124	Phase 1
0.7669	Intermediate Similarity	NPD920	Approved
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3817	Phase 2
0.7654	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD37	Approved
0.764	Intermediate Similarity	NPD8434	Phase 2
0.763	Intermediate Similarity	NPD3818	Discontinued
0.7619	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD4965	Approved
0.7619	Intermediate Similarity	NPD4966	Approved
0.7616	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6273	Approved
0.7605	Intermediate Similarity	NPD5761	Phase 2
0.7605	Intermediate Similarity	NPD5760	Phase 2
0.7597	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6799	Approved
0.7586	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8313	Approved
0.7571	Intermediate Similarity	NPD8312	Approved
0.7562	Intermediate Similarity	NPD1243	Approved
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7074	Phase 3
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7529	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3750	Approved
0.7515	Intermediate Similarity	NPD3882	Suspended
0.7514	Intermediate Similarity	NPD6166	Phase 2
0.7514	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2801	Approved
0.7486	Intermediate Similarity	NPD7054	Approved
0.7484	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1551	Phase 2
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7456	Intermediate Similarity	NPD5402	Approved
0.7453	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7472	Approved
0.7442	Intermediate Similarity	NPD7199	Phase 2
0.7429	Intermediate Similarity	NPD7228	Approved
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1510	Phase 2
0.7421	Intermediate Similarity	NPD3748	Approved
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1607	Approved
0.7396	Intermediate Similarity	NPD1465	Phase 2
0.7381	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1511	Approved
0.7372	Intermediate Similarity	NPD7985	Registered
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.736	Intermediate Similarity	NPD7251	Discontinued
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7326	Intermediate Similarity	NPD919	Approved
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7808	Phase 3
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7303	Intermediate Similarity	NPD6797	Phase 2
0.7303	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7003	Approved
0.7289	Intermediate Similarity	NPD1512	Approved
0.7288	Intermediate Similarity	NPD7286	Phase 2
0.7278	Intermediate Similarity	NPD1240	Approved
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7268	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7783	Phase 2
0.7263	Intermediate Similarity	NPD7240	Approved
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7262	Intermediate Similarity	NPD7458	Discontinued
0.7257	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD8151	Discontinued
0.7246	Intermediate Similarity	NPD5403	Approved
0.7241	Intermediate Similarity	NPD8127	Discontinued
0.7239	Intermediate Similarity	NPD6674	Discontinued
0.7232	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5401	Approved
0.7222	Intermediate Similarity	NPD6002	Phase 3
0.7222	Intermediate Similarity	NPD6004	Phase 3
0.7222	Intermediate Similarity	NPD6005	Phase 3
0.7222	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5953	Discontinued
0.72	Intermediate Similarity	NPD8366	Approved
0.72	Intermediate Similarity	NPD3787	Discontinued
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4625	Phase 3
0.7195	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4140	Approved
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7143	Intermediate Similarity	NPD1247	Approved
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7115	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8032	Phase 2
0.7105	Intermediate Similarity	NPD6776	Approved
0.7105	Intermediate Similarity	NPD6780	Approved
0.7105	Intermediate Similarity	NPD6777	Approved
0.7105	Intermediate Similarity	NPD6782	Approved
0.7105	Intermediate Similarity	NPD6781	Approved
0.7105	Intermediate Similarity	NPD6779	Approved
0.7105	Intermediate Similarity	NPD6778	Approved
0.7097	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD7697	Approved
0.7083	Intermediate Similarity	NPD7696	Phase 3
0.7083	Intermediate Similarity	NPD7698	Approved
0.7081	Intermediate Similarity	NPD4287	Approved
0.7078	Intermediate Similarity	NPD1608	Approved
0.7063	Intermediate Similarity	NPD2979	Phase 3
0.7062	Intermediate Similarity	NPD3926	Phase 2
0.7059	Intermediate Similarity	NPD8491	Approved
0.7053	Intermediate Similarity	NPD8285	Discontinued
0.7047	Intermediate Similarity	NPD7871	Phase 2
0.7047	Intermediate Similarity	NPD7870	Phase 2
0.7044	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3764	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7177	Discontinued
0.7032	Intermediate Similarity	NPD4749	Approved
0.703	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4360	Phase 2
0.7021	Intermediate Similarity	NPD4363	Phase 3
0.702	Intermediate Similarity	NPD7644	Approved
0.7019	Intermediate Similarity	NPD230	Phase 1
0.7019	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7012	Intermediate Similarity	NPD5762	Approved
0.7012	Intermediate Similarity	NPD2344	Approved
0.7012	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD7236	Approved
0.6994	Remote Similarity	NPD4308	Phase 3
0.6994	Remote Similarity	NPD8455	Phase 2
0.6993	Remote Similarity	NPD1778	Approved
0.6987	Remote Similarity	NPD6696	Suspended
0.6978	Remote Similarity	NPD6765	Approved
0.6978	Remote Similarity	NPD6764	Approved
0.6959	Remote Similarity	NPD8320	Phase 1
0.6959	Remote Similarity	NPD8319	Approved
0.6954	Remote Similarity	NPD5353	Approved
0.6951	Remote Similarity	NPD2438	Suspended
0.6943	Remote Similarity	NPD2797	Approved
0.6943	Remote Similarity	NPD6823	Phase 2
0.6942	Remote Similarity	NPD8469	Approved
0.6939	Remote Similarity	NPD7701	Phase 2
0.6937	Remote Similarity	NPD3268	Approved
0.6937	Remote Similarity	NPD411	Approved
0.6931	Remote Similarity	NPD6535	Approved
0.6931	Remote Similarity	NPD6534	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