NPASS Compound

Structure

NPC198075 OpenBabel07101719512D 28 31 0 0 0 0 0 0 0 0999 V2000 -0.1715 5.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9036 5.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9036 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1945 -1.2005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1945 -1.2005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1586 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2926 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1586 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 4.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1715 3.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 5.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4265 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1715 2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2926 2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4265 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1715 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 -0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3890 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2926 3.7515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9036 2.7515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 3.7515 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 2 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 14 1 0 0 0 0 12 20 2 0 0 0 0 12 22 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 24 2 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	379.18
Volume:	397.204
LogP:	6.366
LogD:	3.901
LogS:	-3.284
# Rotatable Bonds:	2
TPSA:	82.28
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	3.73
Fsp3:	0.348
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:	-5.013
MDCK Permeability:	1.4781183381273877e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.626
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	99.56302642822266%
Volume Distribution (VD):	1.082
Pgp-substrate:	1.634319543838501%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.41
CYP2C19-substrate:	0.487
CYP2C9-inhibitor:	0.563
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.657

ADMET: Excretion

Clearance (CL):	1.847
Half-life (T1/2):	0.238

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.384
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.596
Rat Oral Acute Toxicity:	0.512
Maximum Recommended Daily Dose:	0.704
Skin Sensitization:	0.682
Carcinogencity:	0.774
Eye Corrosion:	0.004
Eye Irritation:	0.379
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC198075

Natural Product ID:	NPC198075
*Common Name:**	WMURTDFNFBXFFU-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WMURTDFNFBXFFU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H25NO4/c1-11(2)9-10-14-17-18-19(13-7-6-8-15(25)16(13)21(17)27)24-23(4,5)28-22(18)12(3)20(14)26/h6-8,11,25-26H,9-10H2,1-5H3
SMILES:	CC(C)CCc1c2c3C(=NC(C)(C)Oc3c(C)c1O)c1cccc(c1C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152650
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO12925	Streptomyces spinoverrucosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23057874]
NPO12925	Streptomyces spinoverrucosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26489038]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2311	Cell Line	Calu-3	Homo sapiens	IC50	>	50000.0	nM	PMID[509201]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[509201]

☑ 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 NPC198075 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	313
0.1-0.2	1593
0.2-0.3	4012
0.3-0.4	11926
0.4-0.5	5859
0.5-0.6	5707
0.6-0.7	7134
0.7-0.8	5590
0.8-0.85	547
0.85-0.9	15
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8704	High Similarity	NPC329844
0.8589	High Similarity	NPC214632
0.8571	High Similarity	NPC65589
0.8571	High Similarity	NPC97028
0.8571	High Similarity	NPC288036
0.8571	High Similarity	NPC97029
0.8571	High Similarity	NPC158338
0.8571	High Similarity	NPC10027
0.8571	High Similarity	NPC100985
0.8571	High Similarity	NPC65775
0.8528	High Similarity	NPC40356
0.8528	High Similarity	NPC154683
0.8509	High Similarity	NPC7025
0.8509	High Similarity	NPC27221
0.8509	High Similarity	NPC256672
0.8494	Intermediate Similarity	NPC186113
0.8476	Intermediate Similarity	NPC178964
0.8476	Intermediate Similarity	NPC135522
0.8476	Intermediate Similarity	NPC169990
0.8476	Intermediate Similarity	NPC280530
0.8476	Intermediate Similarity	NPC95842
0.8476	Intermediate Similarity	NPC210942
0.8466	Intermediate Similarity	NPC258249
0.8466	Intermediate Similarity	NPC474417
0.8466	Intermediate Similarity	NPC149526
0.8466	Intermediate Similarity	NPC478148
0.8457	Intermediate Similarity	NPC329933
0.8447	Intermediate Similarity	NPC22005
0.8447	Intermediate Similarity	NPC123202
0.8447	Intermediate Similarity	NPC7943
0.8434	Intermediate Similarity	NPC44199
0.8415	Intermediate Similarity	NPC87708
0.8405	Intermediate Similarity	NPC158866
0.8405	Intermediate Similarity	NPC227122
0.8383	Intermediate Similarity	NPC177650
0.8354	Intermediate Similarity	NPC232645
0.8354	Intermediate Similarity	NPC305965
0.8354	Intermediate Similarity	NPC72958
0.8344	Intermediate Similarity	NPC269420
0.8343	Intermediate Similarity	NPC473961
0.8333	Intermediate Similarity	NPC126767
0.8333	Intermediate Similarity	NPC118027
0.8333	Intermediate Similarity	NPC190648
0.8333	Intermediate Similarity	NPC71055
0.8333	Intermediate Similarity	NPC312929
0.8333	Intermediate Similarity	NPC34802
0.8333	Intermediate Similarity	NPC186325
0.8333	Intermediate Similarity	NPC289042
0.8333	Intermediate Similarity	NPC56433
0.8333	Intermediate Similarity	NPC245584
0.8333	Intermediate Similarity	NPC312993
0.8323	Intermediate Similarity	NPC201127
0.8323	Intermediate Similarity	NPC272196
0.8313	Intermediate Similarity	NPC66508
0.8313	Intermediate Similarity	NPC55662
0.8313	Intermediate Similarity	NPC1534
0.8313	Intermediate Similarity	NPC226656
0.8313	Intermediate Similarity	NPC166054
0.8313	Intermediate Similarity	NPC254351
0.8303	Intermediate Similarity	NPC45934
0.8303	Intermediate Similarity	NPC142527
0.8294	Intermediate Similarity	NPC207690
0.8293	Intermediate Similarity	NPC202595
0.8293	Intermediate Similarity	NPC470568
0.8293	Intermediate Similarity	NPC471115
0.8293	Intermediate Similarity	NPC290954
0.8293	Intermediate Similarity	NPC29777
0.8293	Intermediate Similarity	NPC255641
0.8284	Intermediate Similarity	NPC273467
0.8284	Intermediate Similarity	NPC18380
0.8284	Intermediate Similarity	NPC189552
0.8282	Intermediate Similarity	NPC105415
0.8282	Intermediate Similarity	NPC37139
0.8274	Intermediate Similarity	NPC474373
0.8274	Intermediate Similarity	NPC46736
0.8274	Intermediate Similarity	NPC55443
0.8274	Intermediate Similarity	NPC195167
0.8274	Intermediate Similarity	NPC18699
0.8272	Intermediate Similarity	NPC473135
0.8272	Intermediate Similarity	NPC469758
0.8272	Intermediate Similarity	NPC470676
0.8272	Intermediate Similarity	NPC473132
0.8263	Intermediate Similarity	NPC146211
0.8261	Intermediate Similarity	NPC189650
0.8261	Intermediate Similarity	NPC11700
0.8261	Intermediate Similarity	NPC219915
0.825	Intermediate Similarity	NPC14871
0.825	Intermediate Similarity	NPC282300
0.8242	Intermediate Similarity	NPC470569
0.8239	Intermediate Similarity	NPC301217
0.8239	Intermediate Similarity	NPC55018
0.8239	Intermediate Similarity	NPC220062
0.8239	Intermediate Similarity	NPC216978
0.8239	Intermediate Similarity	NPC303633
0.8239	Intermediate Similarity	NPC96565
0.8232	Intermediate Similarity	NPC233267
0.8232	Intermediate Similarity	NPC473978
0.8232	Intermediate Similarity	NPC474052
0.8232	Intermediate Similarity	NPC70764
0.8232	Intermediate Similarity	NPC291049
0.8225	Intermediate Similarity	NPC292863
0.8225	Intermediate Similarity	NPC470810
0.8225	Intermediate Similarity	NPC297212
0.8225	Intermediate Similarity	NPC471973
0.8225	Intermediate Similarity	NPC476280
0.8225	Intermediate Similarity	NPC184326
0.8221	Intermediate Similarity	NPC308200
0.8214	Intermediate Similarity	NPC164110
0.8214	Intermediate Similarity	NPC246647
0.8214	Intermediate Similarity	NPC268360
0.8214	Intermediate Similarity	NPC212967
0.8214	Intermediate Similarity	NPC96342
0.821	Intermediate Similarity	NPC234629
0.821	Intermediate Similarity	NPC271288
0.821	Intermediate Similarity	NPC326500
0.821	Intermediate Similarity	NPC469764
0.821	Intermediate Similarity	NPC311741
0.8204	Intermediate Similarity	NPC275575
0.8199	Intermediate Similarity	NPC310340
0.8199	Intermediate Similarity	NPC78803
0.8199	Intermediate Similarity	NPC293852
0.8199	Intermediate Similarity	NPC217083
0.8199	Intermediate Similarity	NPC214236
0.8199	Intermediate Similarity	NPC62840
0.8199	Intermediate Similarity	NPC84266
0.8199	Intermediate Similarity	NPC59739
0.8199	Intermediate Similarity	NPC299080
0.8198	Intermediate Similarity	NPC37870
0.8198	Intermediate Similarity	NPC30027
0.8193	Intermediate Similarity	NPC217447
0.8187	Intermediate Similarity	NPC241100
0.8187	Intermediate Similarity	NPC270883
0.8187	Intermediate Similarity	NPC172986
0.8187	Intermediate Similarity	NPC261227
0.8187	Intermediate Similarity	NPC275734
0.8187	Intermediate Similarity	NPC159275
0.8182	Intermediate Similarity	NPC120105
0.8182	Intermediate Similarity	NPC101957
0.8182	Intermediate Similarity	NPC150928
0.8182	Intermediate Similarity	NPC294646
0.8182	Intermediate Similarity	NPC472633
0.8182	Intermediate Similarity	NPC147735
0.8182	Intermediate Similarity	NPC325983
0.8176	Intermediate Similarity	NPC201395
0.8176	Intermediate Similarity	NPC137232
0.8176	Intermediate Similarity	NPC278427
0.8176	Intermediate Similarity	NPC66288
0.8171	Intermediate Similarity	NPC106328
0.8171	Intermediate Similarity	NPC5537
0.8171	Intermediate Similarity	NPC37135
0.8171	Intermediate Similarity	NPC266572
0.8171	Intermediate Similarity	NPC186397
0.8171	Intermediate Similarity	NPC39195
0.8171	Intermediate Similarity	NPC35150
0.8171	Intermediate Similarity	NPC145467
0.8166	Intermediate Similarity	NPC197856
0.8166	Intermediate Similarity	NPC324736
0.816	Intermediate Similarity	NPC225173
0.816	Intermediate Similarity	NPC477955
0.816	Intermediate Similarity	NPC474161
0.816	Intermediate Similarity	NPC163846
0.816	Intermediate Similarity	NPC476088
0.816	Intermediate Similarity	NPC154217
0.816	Intermediate Similarity	NPC196114
0.8155	Intermediate Similarity	NPC56049
0.8155	Intermediate Similarity	NPC192587
0.8155	Intermediate Similarity	NPC180924
0.8155	Intermediate Similarity	NPC54830
0.8155	Intermediate Similarity	NPC4547
0.815	Intermediate Similarity	NPC225419
0.815	Intermediate Similarity	NPC76647
0.8148	Intermediate Similarity	NPC19896
0.8148	Intermediate Similarity	NPC38219
0.8148	Intermediate Similarity	NPC9117
0.8148	Intermediate Similarity	NPC24821
0.8148	Intermediate Similarity	NPC190637
0.8148	Intermediate Similarity	NPC212932
0.8148	Intermediate Similarity	NPC293053
0.8144	Intermediate Similarity	NPC193200
0.8144	Intermediate Similarity	NPC235333
0.8144	Intermediate Similarity	NPC208806
0.8144	Intermediate Similarity	NPC477691
0.814	Intermediate Similarity	NPC469664
0.814	Intermediate Similarity	NPC156432
0.814	Intermediate Similarity	NPC303174
0.8137	Intermediate Similarity	NPC126534
0.8137	Intermediate Similarity	NPC64908
0.8137	Intermediate Similarity	NPC94076
0.8137	Intermediate Similarity	NPC232021
0.8137	Intermediate Similarity	NPC147688
0.8137	Intermediate Similarity	NPC110969
0.8137	Intermediate Similarity	NPC118840
0.8137	Intermediate Similarity	NPC40118
0.8137	Intermediate Similarity	NPC49108
0.8137	Intermediate Similarity	NPC156590
0.8137	Intermediate Similarity	NPC182255
0.8137	Intermediate Similarity	NPC205006
0.8133	Intermediate Similarity	NPC178484
0.8133	Intermediate Similarity	NPC133856
0.8129	Intermediate Similarity	NPC15374

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 NPC198075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	859
0.2-0.3	1125
0.3-0.4	2465
0.4-0.5	2312
0.5-0.6	1446
0.6-0.7	564
0.7-0.8	131
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8098	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6959	Discontinued
0.7988	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD3750	Approved
0.7929	Intermediate Similarity	NPD7819	Suspended
0.7886	Intermediate Similarity	NPD7473	Discontinued
0.7824	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6232	Discontinued
0.7811	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3226	Approved
0.7764	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7768	Phase 2
0.773	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2801	Approved
0.7711	Intermediate Similarity	NPD1511	Approved
0.7706	Intermediate Similarity	NPD7411	Suspended
0.7688	Intermediate Similarity	NPD3749	Approved
0.7669	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2346	Discontinued
0.7665	Intermediate Similarity	NPD2533	Approved
0.7665	Intermediate Similarity	NPD2534	Approved
0.7665	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD1510	Phase 2
0.7654	Intermediate Similarity	NPD3748	Approved
0.7647	Intermediate Similarity	NPD4380	Phase 2
0.764	Intermediate Similarity	NPD1607	Approved
0.7629	Intermediate Similarity	NPD8151	Discontinued
0.7622	Intermediate Similarity	NPD1549	Phase 2
0.7619	Intermediate Similarity	NPD1512	Approved
0.7607	Intermediate Similarity	NPD2796	Approved
0.7605	Intermediate Similarity	NPD7390	Discontinued
0.7592	Intermediate Similarity	NPD6823	Phase 2
0.7558	Intermediate Similarity	NPD1934	Approved
0.7546	Intermediate Similarity	NPD2799	Discontinued
0.7528	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1240	Approved
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.7486	Intermediate Similarity	NPD7075	Discontinued
0.747	Intermediate Similarity	NPD2800	Approved
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7438	Intermediate Similarity	NPD4625	Phase 3
0.743	Intermediate Similarity	NPD6166	Phase 2
0.743	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3882	Suspended
0.7425	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD6746	Phase 2
0.7394	Intermediate Similarity	NPD5405	Approved
0.7394	Intermediate Similarity	NPD5408	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7394	Intermediate Similarity	NPD5404	Approved
0.7394	Intermediate Similarity	NPD5406	Approved
0.7394	Intermediate Similarity	NPD1551	Phase 2
0.7391	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6559	Discontinued
0.7374	Intermediate Similarity	NPD7801	Approved
0.7356	Intermediate Similarity	NPD6801	Discontinued
0.7341	Intermediate Similarity	NPD6599	Discontinued
0.7317	Intermediate Similarity	NPD4097	Suspended
0.7316	Intermediate Similarity	NPD4363	Phase 3
0.7316	Intermediate Similarity	NPD4360	Phase 2
0.7308	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8312	Approved
0.7297	Intermediate Similarity	NPD8313	Approved
0.7296	Intermediate Similarity	NPD1470	Approved
0.7288	Intermediate Similarity	NPD6971	Discontinued
0.7284	Intermediate Similarity	NPD2313	Discontinued
0.7277	Intermediate Similarity	NPD4361	Phase 2
0.7277	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5402	Approved
0.7273	Intermediate Similarity	NPD3817	Phase 2
0.7267	Intermediate Similarity	NPD4908	Phase 1
0.7262	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1201	Approved
0.7253	Intermediate Similarity	NPD3818	Discontinued
0.7253	Intermediate Similarity	NPD7177	Discontinued
0.7241	Intermediate Similarity	NPD6502	Phase 2
0.7236	Intermediate Similarity	NPD7874	Approved
0.7236	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3300	Phase 2
0.7232	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7003	Approved
0.7216	Intermediate Similarity	NPD6776	Approved
0.7216	Intermediate Similarity	NPD6777	Approved
0.7216	Intermediate Similarity	NPD6779	Approved
0.7216	Intermediate Similarity	NPD6781	Approved
0.7216	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6778	Approved
0.7216	Intermediate Similarity	NPD6780	Approved
0.7216	Intermediate Similarity	NPD6782	Approved
0.7213	Intermediate Similarity	NPD7054	Approved
0.7193	Intermediate Similarity	NPD6799	Approved
0.7189	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7654	Discontinued
0.7174	Intermediate Similarity	NPD7472	Approved
0.7174	Intermediate Similarity	NPD7074	Phase 3
0.7168	Intermediate Similarity	NPD5403	Approved
0.716	Intermediate Similarity	NPD1243	Approved
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD2344	Approved
0.7135	Intermediate Similarity	NPD6797	Phase 2
0.712	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1465	Phase 2
0.7118	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6651	Approved
0.7107	Intermediate Similarity	NPD7697	Approved
0.7107	Intermediate Similarity	NPD7696	Phase 3
0.7107	Intermediate Similarity	NPD7698	Approved
0.7097	Intermediate Similarity	NPD7251	Discontinued
0.7086	Intermediate Similarity	NPD4005	Discontinued
0.7081	Intermediate Similarity	NPD2797	Approved
0.7079	Intermediate Similarity	NPD4288	Approved
0.7073	Intermediate Similarity	NPD3268	Approved
0.7071	Intermediate Similarity	NPD7870	Phase 2
0.7071	Intermediate Similarity	NPD7871	Phase 2
0.7069	Intermediate Similarity	NPD920	Approved
0.7063	Intermediate Similarity	NPD4749	Approved
0.7062	Intermediate Similarity	NPD6844	Discontinued
0.7059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7808	Phase 3
0.7052	Intermediate Similarity	NPD5401	Approved
0.7052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7701	Phase 2
0.7043	Intermediate Similarity	NPD5953	Discontinued
0.7033	Intermediate Similarity	NPD7229	Phase 3
0.703	Intermediate Similarity	NPD7783	Phase 2
0.703	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8067	Phase 3
0.7024	Intermediate Similarity	NPD4308	Phase 3
0.702	Intermediate Similarity	NPD7435	Discontinued
0.7016	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6273	Approved
0.7005	Intermediate Similarity	NPD6104	Discontinued
0.6994	Remote Similarity	NPD4357	Discontinued
0.6989	Remote Similarity	NPD1729	Discontinued
0.6988	Remote Similarity	NPD943	Approved
0.6982	Remote Similarity	NPD4477	Approved
0.6982	Remote Similarity	NPD4476	Approved
0.6977	Remote Similarity	NPD2309	Approved
0.6975	Remote Similarity	NPD1203	Approved
0.6973	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8366	Approved
0.697	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3764	Approved
0.6966	Remote Similarity	NPD37	Approved
0.6961	Remote Similarity	NPD6234	Discontinued
0.6959	Remote Similarity	NPD6534	Approved
0.6959	Remote Similarity	NPD6535	Approved
0.6954	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3823	Discontinued
0.6944	Remote Similarity	NPD4966	Approved
0.6944	Remote Similarity	NPD4967	Phase 2
0.6944	Remote Similarity	NPD4965	Approved
0.6937	Remote Similarity	NPD1610	Phase 2
0.6936	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7286	Phase 2
0.6923	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4628	Phase 3
0.6915	Remote Similarity	NPD7584	Approved
0.6914	Remote Similarity	NPD1283	Approved
0.6904	Remote Similarity	NPD6874	Approved
0.6904	Remote Similarity	NPD8285	Discontinued
0.6902	Remote Similarity	NPD3926	Phase 2
0.69	Remote Similarity	NPD8319	Approved
0.69	Remote Similarity	NPD8320	Phase 1
0.6893	Remote Similarity	NPD7458	Discontinued
0.6889	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1247	Approved
0.6882	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7427	Discontinued
0.6875	Remote Similarity	NPD1898	Discontinued
0.6875	Remote Similarity	NPD7291	Discontinued
0.6868	Remote Similarity	NPD919	Approved
0.6867	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD411	Approved
0.6865	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2654	Approved
0.6857	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7447	Phase 1
0.6855	Remote Similarity	NPD1651	Approved
0.6854	Remote Similarity	NPD6585	Discontinued
0.6853	Remote Similarity	NPD7700	Phase 2
0.6853	Remote Similarity	NPD7699	Phase 2
0.6848	Remote Similarity	NPD7315	Approved
0.6845	Remote Similarity	NPD5123	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