NPASS Compound

Structure

NPC288036 OpenBabel07101719522D 23 25 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 4 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 17 18 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.12
Volume:	319.711
LogP:	3.803
LogD:	3.25
LogS:	-4.586
# Rotatable Bonds:	4
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	2.656
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.801
MDCK Permeability:	1.5862538930377923e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.765
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.644

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	89.03176879882812%
Volume Distribution (VD):	0.901
Pgp-substrate:	10.850919723510742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.432
CYP2C9-inhibitor:	0.791
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.673
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.542
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	7.537
Half-life (T1/2):	0.647

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.577
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.645
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.83
Skin Sensitization:	0.587
Carcinogencity:	0.064
Eye Corrosion:	0.012
Eye Irritation:	0.755
Respiratory Toxicity:	0.582

Download Data

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

Natural Product: NPC288036

Natural Product ID:	NPC288036
*Common Name:**	8-Hydroxy-5,10-Dimethoxy-2-Propylbenzo[H]Chromen-4-One
IUPAC Name:	8-hydroxy-5,10-dimethoxy-2-propylbenzo[h]chromen-4-one
Synonyms:
Standard InCHIKey:	QUPYOVWNMKVWDO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-4-5-12-9-13(20)17-14(21-2)7-10-6-11(19)8-15(22-3)16(10)18(17)23-12/h6-9,19H,4-5H2,1-3H3
SMILES:	CCCc1cc(=O)c2c(o1)c1c(OC)cc(cc1cc2OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172279
PubChem CID:	44136693
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO32950	crinoids	Class	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20627559]

☑ 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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	5900.0	nM	PMID[532777]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Inhibition	=	46.3	%	PMID[532777]

☑ 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 NPC288036 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	412
0.1-0.2	1832
0.2-0.3	4107
0.3-0.4	10832
0.4-0.5	7466
0.5-0.6	3782
0.6-0.7	5349
0.7-0.8	4841
0.8-0.85	2221
0.85-0.9	1553
0.9-0.95	278
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC65589
1.0	High Similarity	NPC97029
1.0	High Similarity	NPC100985
1.0	High Similarity	NPC158338
1.0	High Similarity	NPC97028
0.993	High Similarity	NPC256672
0.993	High Similarity	NPC27221
0.993	High Similarity	NPC7025
0.9859	High Similarity	NPC22005
0.9859	High Similarity	NPC7943
0.9859	High Similarity	NPC123202
0.9726	High Similarity	NPC169990
0.9726	High Similarity	NPC210942
0.9726	High Similarity	NPC329844
0.9724	High Similarity	NPC474417
0.9724	High Similarity	NPC149526
0.9724	High Similarity	NPC232645
0.9724	High Similarity	NPC72958
0.9658	High Similarity	NPC87708
0.9648	High Similarity	NPC189650
0.9589	High Similarity	NPC258249
0.9589	High Similarity	NPC478148
0.9583	High Similarity	NPC34802
0.9577	High Similarity	NPC84266
0.9524	High Similarity	NPC40356
0.9524	High Similarity	NPC154683
0.9521	High Similarity	NPC325983
0.9507	High Similarity	NPC182255
0.9507	High Similarity	NPC94076
0.9452	High Similarity	NPC10027
0.9452	High Similarity	NPC65775
0.9452	High Similarity	NPC329933
0.9452	High Similarity	NPC233267
0.9452	High Similarity	NPC291049
0.9441	High Similarity	NPC310340
0.9404	High Similarity	NPC186325
0.9392	High Similarity	NPC217447
0.9388	High Similarity	NPC202595
0.9384	High Similarity	NPC105415
0.9342	High Similarity	NPC66288
0.9342	High Similarity	NPC273467
0.9342	High Similarity	NPC189552
0.9338	High Similarity	NPC177650
0.9333	High Similarity	NPC180924
0.9329	High Similarity	NPC214632
0.9324	High Similarity	NPC133856
0.932	High Similarity	NPC269420
0.9315	High Similarity	NPC259632
0.9315	High Similarity	NPC312929
0.9315	High Similarity	NPC245584
0.9315	High Similarity	NPC289042
0.9315	High Similarity	NPC56433
0.9315	High Similarity	NPC118027
0.9315	High Similarity	NPC126767
0.9315	High Similarity	NPC190648
0.9301	High Similarity	NPC159275
0.9301	High Similarity	NPC241100
0.9301	High Similarity	NPC275734
0.9276	High Similarity	NPC312993
0.9272	High Similarity	NPC164110
0.9272	High Similarity	NPC212967
0.9272	High Similarity	NPC96342
0.9272	High Similarity	NPC246647
0.9262	High Similarity	NPC273483
0.9262	High Similarity	NPC175978
0.9257	High Similarity	NPC158866
0.9257	High Similarity	NPC227122
0.9257	High Similarity	NPC470568
0.9252	High Similarity	NPC37139
0.9247	High Similarity	NPC473927
0.9247	High Similarity	NPC163846
0.9247	High Similarity	NPC196114
0.9247	High Similarity	NPC290133
0.9247	High Similarity	NPC24136
0.9247	High Similarity	NPC225173
0.9247	High Similarity	NPC187282
0.9241	High Similarity	NPC11700
0.9236	High Similarity	NPC110969
0.9236	High Similarity	NPC282300
0.9231	High Similarity	NPC96565
0.9231	High Similarity	NPC217186
0.9231	High Similarity	NPC216978
0.9231	High Similarity	NPC78913
0.9231	High Similarity	NPC55018
0.9231	High Similarity	NPC18260
0.9231	High Similarity	NPC220062
0.9231	High Similarity	NPC301217
0.9231	High Similarity	NPC303633
0.9231	High Similarity	NPC53181
0.9221	High Similarity	NPC270837
0.9211	High Similarity	NPC55443
0.9211	High Similarity	NPC18699
0.9211	High Similarity	NPC85121
0.9205	High Similarity	NPC146211
0.92	High Similarity	NPC93552
0.92	High Similarity	NPC280530
0.92	High Similarity	NPC178964
0.92	High Similarity	NPC135522
0.92	High Similarity	NPC193200
0.92	High Similarity	NPC95842
0.9195	High Similarity	NPC470569
0.9189	High Similarity	NPC474052
0.9189	High Similarity	NPC473978
0.9184	High Similarity	NPC125801
0.9178	High Similarity	NPC234629
0.9178	High Similarity	NPC134621
0.9178	High Similarity	NPC311741
0.9178	High Similarity	NPC216538
0.9178	High Similarity	NPC271288
0.9178	High Similarity	NPC273538
0.9178	High Similarity	NPC224714
0.9172	High Similarity	NPC11561
0.9172	High Similarity	NPC226636
0.9172	High Similarity	NPC1534
0.9167	High Similarity	NPC172986
0.9167	High Similarity	NPC261227
0.9167	High Similarity	NPC150522
0.9167	High Similarity	NPC270883
0.9161	High Similarity	NPC469664
0.9161	High Similarity	NPC131130
0.9161	High Similarity	NPC201395
0.9156	High Similarity	NPC294965
0.9155	High Similarity	NPC174999
0.915	High Similarity	NPC470810
0.9145	High Similarity	NPC268360
0.9145	High Similarity	NPC272196
0.9145	High Similarity	NPC44199
0.9145	High Similarity	NPC201127
0.9145	High Similarity	NPC263483
0.9139	High Similarity	NPC149618
0.9139	High Similarity	NPC226656
0.9139	High Similarity	NPC254351
0.9139	High Similarity	NPC66508
0.9139	High Similarity	NPC148938
0.9139	High Similarity	NPC89625
0.9133	High Similarity	NPC45934
0.9133	High Similarity	NPC142527
0.9128	High Similarity	NPC290954
0.9128	High Similarity	NPC255641
0.9128	High Similarity	NPC294646
0.9128	High Similarity	NPC472633
0.9128	High Similarity	NPC147735
0.9128	High Similarity	NPC37348
0.9128	High Similarity	NPC150928
0.9116	High Similarity	NPC99454
0.9116	High Similarity	NPC477955
0.9116	High Similarity	NPC5820
0.9116	High Similarity	NPC124729
0.9116	High Similarity	NPC267509
0.9116	High Similarity	NPC473135
0.9116	High Similarity	NPC470676
0.9116	High Similarity	NPC473132
0.9116	High Similarity	NPC178343
0.9116	High Similarity	NPC306488
0.9116	High Similarity	NPC130176
0.9116	High Similarity	NPC237208
0.911	High Similarity	NPC158874
0.911	High Similarity	NPC19896
0.911	High Similarity	NPC190637
0.911	High Similarity	NPC293053
0.911	High Similarity	NPC66404
0.911	High Similarity	NPC212932
0.911	High Similarity	NPC18585
0.911	High Similarity	NPC9117
0.911	High Similarity	NPC166138
0.911	High Similarity	NPC219915
0.911	High Similarity	NPC95123
0.911	High Similarity	NPC24821
0.911	High Similarity	NPC106985
0.9103	High Similarity	NPC17170
0.9103	High Similarity	NPC232021
0.9103	High Similarity	NPC258630
0.9103	High Similarity	NPC103362
0.9103	High Similarity	NPC205006
0.9103	High Similarity	NPC126534
0.9103	High Similarity	NPC279650
0.9103	High Similarity	NPC156190
0.9103	High Similarity	NPC40118
0.9103	High Similarity	NPC166689
0.9103	High Similarity	NPC49108
0.9103	High Similarity	NPC156590
0.9103	High Similarity	NPC64908
0.9103	High Similarity	NPC118840
0.9103	High Similarity	NPC147688
0.9103	High Similarity	NPC96408
0.9097	High Similarity	NPC472366
0.9097	High Similarity	NPC197168
0.9091	High Similarity	NPC18380
0.9085	High Similarity	NPC195167
0.9085	High Similarity	NPC474373
0.9085	High Similarity	NPC242712
0.9079	High Similarity	NPC13779
0.9079	High Similarity	NPC475799
0.9079	High Similarity	NPC4547
0.9073	High Similarity	NPC472799
0.9073	High Similarity	NPC235333
0.9067	High Similarity	NPC58668
0.9067	High Similarity	NPC106372
0.906	High Similarity	NPC266499
0.9054	High Similarity	NPC97716

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 NPC288036 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	1023
0.2-0.3	1549
0.3-0.4	2661
0.4-0.5	1875
0.5-0.6	1073
0.6-0.7	389
0.7-0.8	135
0.8-0.85	44
0.85-0.9	17
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9178	High Similarity	NPD4378	Clinical (unspecified phase)
0.9091	High Similarity	NPD6959	Discontinued
0.8947	High Similarity	NPD7819	Suspended
0.8824	High Similarity	NPD2393	Clinical (unspecified phase)
0.8792	High Similarity	NPD7410	Clinical (unspecified phase)
0.8767	High Similarity	NPD970	Clinical (unspecified phase)
0.8699	High Similarity	NPD1552	Clinical (unspecified phase)
0.8699	High Similarity	NPD1550	Clinical (unspecified phase)
0.869	High Similarity	NPD1510	Phase 2
0.8681	High Similarity	NPD1607	Approved
0.8671	High Similarity	NPD6232	Discontinued
0.8667	High Similarity	NPD2533	Approved
0.8667	High Similarity	NPD2532	Approved
0.8667	High Similarity	NPD2534	Approved
0.8645	High Similarity	NPD8443	Clinical (unspecified phase)
0.8639	High Similarity	NPD1549	Phase 2
0.863	High Similarity	NPD2796	Approved
0.8625	High Similarity	NPD7473	Discontinued
0.86	High Similarity	NPD1511	Approved
0.8581	High Similarity	NPD2801	Approved
0.8562	High Similarity	NPD1509	Clinical (unspecified phase)
0.8542	High Similarity	NPD1240	Approved
0.8523	High Similarity	NPD3750	Approved
0.8516	High Similarity	NPD1934	Approved
0.8506	High Similarity	NPD4380	Phase 2
0.8487	Intermediate Similarity	NPD1512	Approved
0.8477	Intermediate Similarity	NPD7390	Discontinued
0.8452	Intermediate Similarity	NPD7411	Suspended
0.8418	Intermediate Similarity	NPD7075	Discontinued
0.8378	Intermediate Similarity	NPD6099	Approved
0.8378	Intermediate Similarity	NPD6100	Approved
0.8354	Intermediate Similarity	NPD7768	Phase 2
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2800	Approved
0.8323	Intermediate Similarity	NPD3226	Approved
0.8302	Intermediate Similarity	NPD3749	Approved
0.8293	Intermediate Similarity	NPD5844	Phase 1
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8269	Intermediate Similarity	NPD6599	Discontinued
0.8239	Intermediate Similarity	NPD3882	Suspended
0.8212	Intermediate Similarity	NPD1243	Approved
0.8207	Intermediate Similarity	NPD4625	Phase 3
0.82	Intermediate Similarity	NPD2346	Discontinued
0.8188	Intermediate Similarity	NPD3748	Approved
0.8187	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8144	Intermediate Similarity	NPD6559	Discontinued
0.8133	Intermediate Similarity	NPD2935	Discontinued
0.8133	Intermediate Similarity	NPD1551	Phase 2
0.8117	Intermediate Similarity	NPD6799	Approved
0.811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6166	Phase 2
0.811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD5494	Approved
0.8072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD6651	Approved
0.8039	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5711	Approved
0.7988	Intermediate Similarity	NPD5710	Approved
0.7964	Intermediate Similarity	NPD7054	Approved
0.7962	Intermediate Similarity	NPD920	Approved
0.7961	Intermediate Similarity	NPD2344	Approved
0.7947	Intermediate Similarity	NPD2799	Discontinued
0.7935	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7472	Approved
0.7917	Intermediate Similarity	NPD7074	Phase 3
0.7905	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5404	Approved
0.7895	Intermediate Similarity	NPD5405	Approved
0.7895	Intermediate Similarity	NPD5408	Approved
0.7895	Intermediate Similarity	NPD5406	Approved
0.7888	Intermediate Similarity	NPD1465	Phase 2
0.787	Intermediate Similarity	NPD6797	Phase 2
0.7862	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7251	Discontinued
0.7806	Intermediate Similarity	NPD4628	Phase 3
0.7805	Intermediate Similarity	NPD919	Approved
0.7785	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2313	Discontinued
0.7778	Intermediate Similarity	NPD1201	Approved
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.7765	Intermediate Similarity	NPD5953	Discontinued
0.7756	Intermediate Similarity	NPD2309	Approved
0.7736	Intermediate Similarity	NPD5403	Approved
0.773	Intermediate Similarity	NPD5402	Approved
0.7725	Intermediate Similarity	NPD3926	Phase 2
0.7722	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1247	Approved
0.7692	Intermediate Similarity	NPD1651	Approved
0.7692	Intermediate Similarity	NPD7003	Approved
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1470	Approved
0.7682	Intermediate Similarity	NPD943	Approved
0.7674	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4749	Approved
0.7667	Intermediate Similarity	NPD3268	Approved
0.7665	Intermediate Similarity	NPD7229	Phase 3
0.7651	Intermediate Similarity	NPD4908	Phase 1
0.7647	Intermediate Similarity	NPD7286	Phase 2
0.7635	Intermediate Similarity	NPD2798	Approved
0.7627	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1283	Approved
0.761	Intermediate Similarity	NPD5401	Approved
0.7597	Intermediate Similarity	NPD4308	Phase 3
0.7588	Intermediate Similarity	NPD7177	Discontinued
0.7568	Intermediate Similarity	NPD1203	Approved
0.7568	Intermediate Similarity	NPD2797	Approved
0.755	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4360	Phase 2
0.7542	Intermediate Similarity	NPD4363	Phase 3
0.7534	Intermediate Similarity	NPD1610	Phase 2
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7527	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4288	Approved
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD4361	Phase 2
0.75	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1471	Phase 3
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7483	Intermediate Similarity	NPD3972	Approved
0.7483	Intermediate Similarity	NPD1608	Approved
0.7457	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD411	Approved
0.7423	Intermediate Similarity	NPD7458	Discontinued
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7415	Intermediate Similarity	NPD1281	Approved
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7415	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2654	Approved
0.7397	Intermediate Similarity	NPD4626	Approved
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7394	Intermediate Similarity	NPD37	Approved
0.7394	Intermediate Similarity	NPD8151	Discontinued
0.7384	Intermediate Similarity	NPD3751	Discontinued
0.7381	Intermediate Similarity	NPD6234	Discontinued
0.7372	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4966	Approved
0.7365	Intermediate Similarity	NPD9717	Approved
0.7365	Intermediate Similarity	NPD4965	Approved
0.7365	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7351	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6273	Approved
0.7338	Intermediate Similarity	NPD4307	Phase 2
0.7338	Intermediate Similarity	NPD2979	Phase 3
0.7338	Intermediate Similarity	NPD4060	Phase 1
0.7337	Intermediate Similarity	NPD6782	Approved
0.7337	Intermediate Similarity	NPD6781	Approved
0.7337	Intermediate Similarity	NPD6778	Approved
0.7337	Intermediate Similarity	NPD6777	Approved
0.7337	Intermediate Similarity	NPD6779	Approved
0.7337	Intermediate Similarity	NPD6780	Approved
0.7337	Intermediate Similarity	NPD6776	Approved
0.7333	Intermediate Similarity	NPD3267	Approved
0.7333	Intermediate Similarity	NPD3266	Approved
0.732	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3764	Approved
0.7318	Intermediate Similarity	NPD4287	Approved
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD230	Phase 1
0.729	Intermediate Similarity	NPD5124	Phase 1
0.729	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD17	Approved
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3225	Approved
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7783	Phase 2
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7696	Phase 3
0.7219	Intermediate Similarity	NPD7698	Approved
0.7219	Intermediate Similarity	NPD1164	Approved
0.7219	Intermediate Similarity	NPD7435	Discontinued
0.7219	Intermediate Similarity	NPD7697	Approved
0.7216	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4476	Approved
0.7215	Intermediate Similarity	NPD4477	Approved
0.7215	Intermediate Similarity	NPD2438	Suspended
0.7211	Intermediate Similarity	NPD5691	Approved
0.7207	Intermediate Similarity	NPD8150	Discontinued
0.7202	Intermediate Similarity	NPD2296	Approved
0.72	Intermediate Similarity	NPD1729	Discontinued
0.72	Intermediate Similarity	NPD3600	Clinical (unspecified phase)

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