NPASS Compound

Structure

NPC201541 OpenBabel07101719242D 21 23 0 0 1 0 0 0 0 0999 V2000 3.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 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 -1.7321 2.0000 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 3.7321 0.0000 0.0000 C 0 0 1 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 0.5000 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 8 1 0 0 0 0 2 4 1 0 0 0 0 2 8 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 12 2 0 0 0 0 7 10 2 0 0 0 0 7 21 1 0 0 0 0 8 16 1 1 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 14 19 2 0 0 0 0 15 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.09
Volume:	281.886
LogP:	0.634
LogD:	1.014
LogS:	-2.515
# Rotatable Bonds:	1
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	3.019
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.184
MDCK Permeability:	9.335602953797206e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.595
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	60.122032165527344%
Volume Distribution (VD):	1.247
Pgp-substrate:	48.66441345214844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.237
CYP1A2-substrate:	0.364
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.465
CYP2D6-substrate:	0.332
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.069

ADMET: Excretion

Clearance (CL):	10.333
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.295
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.242
Rat Oral Acute Toxicity:	0.424
Maximum Recommended Daily Dose:	0.753
Skin Sensitization:	0.588
Carcinogencity:	0.108
Eye Corrosion:	0.005
Eye Irritation:	0.689
Respiratory Toxicity:	0.374

Download Data

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

Natural Product: NPC201541

Natural Product ID:	NPC201541
*Common Name:**	PQNNMOPFCAZSEC-HWJBBNHMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PQNNMOPFCAZSEC-HWJBBNHMSA-N
Standard InCHI:	InChI=1S/C15H16O6/c16-8-1-3-15(20,4-2-8)10-7-21-12-6-9(17)5-11(18)13(12)14(10)19/h5-8,16-18,20H,1-4H2/t8-,15+
SMILES:	C1C[C@@](CC[C@H]1O)(c1coc2cc(cc(c2c1=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081364
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	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
GI50	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
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	75000.0	nM	PMID[455678]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	147000.0	nM	PMID[455678]

☑ 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 NPC201541 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	407
0.1-0.2	1671
0.2-0.3	3845
0.3-0.4	9646
0.4-0.5	9166
0.5-0.6	3915
0.6-0.7	5881
0.7-0.8	4580
0.8-0.85	2550
0.85-0.9	923
0.9-0.95	111
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9708	High Similarity	NPC95751
0.9424	High Similarity	NPC476178
0.9424	High Similarity	NPC475705
0.9424	High Similarity	NPC117836
0.9424	High Similarity	NPC51887
0.9407	High Similarity	NPC234560
0.9407	High Similarity	NPC39426
0.9362	High Similarity	NPC51070
0.9362	High Similarity	NPC222298
0.9338	High Similarity	NPC193792
0.9338	High Similarity	NPC235428
0.9338	High Similarity	NPC87545
0.9281	High Similarity	NPC321980
0.9281	High Similarity	NPC469404
0.9281	High Similarity	NPC470087
0.9275	High Similarity	NPC469523
0.927	High Similarity	NPC294409
0.927	High Similarity	NPC181124
0.927	High Similarity	NPC7013
0.927	High Similarity	NPC116632
0.927	High Similarity	NPC303644
0.927	High Similarity	NPC209560
0.927	High Similarity	NPC162680
0.927	High Similarity	NPC212767
0.9265	High Similarity	NPC84699
0.922	High Similarity	NPC224714
0.9209	High Similarity	NPC259166
0.9209	High Similarity	NPC144118
0.9209	High Similarity	NPC80962
0.9209	High Similarity	NPC326109
0.9209	High Similarity	NPC215311
0.9209	High Similarity	NPC48624
0.9209	High Similarity	NPC253822
0.9209	High Similarity	NPC172250
0.9209	High Similarity	NPC219917
0.9209	High Similarity	NPC204985
0.9209	High Similarity	NPC213659
0.9203	High Similarity	NPC309154
0.9203	High Similarity	NPC12175
0.9203	High Similarity	NPC90665
0.9203	High Similarity	NPC55162
0.9203	High Similarity	NPC279668
0.9203	High Similarity	NPC278323
0.9167	High Similarity	NPC61258
0.9155	High Similarity	NPC316769
0.9149	High Similarity	NPC301751
0.9149	High Similarity	NPC245482
0.9143	High Similarity	NPC26051
0.9143	High Similarity	NPC55832
0.9143	High Similarity	NPC268204
0.9143	High Similarity	NPC52789
0.9143	High Similarity	NPC470089
0.9137	High Similarity	NPC283429
0.9137	High Similarity	NPC470211
0.9137	High Similarity	NPC295384
0.9111	High Similarity	NPC65060
0.9104	High Similarity	NPC185497
0.9097	High Similarity	NPC5173
0.9091	High Similarity	NPC85773
0.9085	High Similarity	NPC470890
0.9078	High Similarity	NPC148545
0.9071	High Similarity	NPC101366
0.9071	High Similarity	NPC182421
0.9065	High Similarity	NPC21350
0.9065	High Similarity	NPC472460
0.9065	High Similarity	NPC147686
0.9065	High Similarity	NPC329225
0.9051	High Similarity	NPC164136
0.9051	High Similarity	NPC286336
0.9034	High Similarity	NPC124478
0.9034	High Similarity	NPC37348
0.9034	High Similarity	NPC177308
0.903	High Similarity	NPC60558
0.9028	High Similarity	NPC6511
0.9028	High Similarity	NPC168085
0.9021	High Similarity	NPC472629
0.9	High Similarity	NPC139554
0.9	High Similarity	NPC140890
0.8993	High Similarity	NPC12296
0.8993	High Similarity	NPC296490
0.8993	High Similarity	NPC13768
0.8993	High Similarity	NPC32441
0.8993	High Similarity	NPC84585
0.8993	High Similarity	NPC476480
0.8993	High Similarity	NPC79943
0.8993	High Similarity	NPC243083
0.8993	High Similarity	NPC107586
0.8993	High Similarity	NPC287246
0.8993	High Similarity	NPC317119
0.8993	High Similarity	NPC295261
0.898	High Similarity	NPC472583
0.898	High Similarity	NPC7989
0.898	High Similarity	NPC223701
0.898	High Similarity	NPC469405
0.8978	High Similarity	NPC56031
0.8978	High Similarity	NPC223354
0.8978	High Similarity	NPC337373
0.8978	High Similarity	NPC18877
0.8978	High Similarity	NPC242294
0.8978	High Similarity	NPC294593
0.8978	High Similarity	NPC263670
0.8978	High Similarity	NPC312318
0.8978	High Similarity	NPC472365
0.8978	High Similarity	NPC144051
0.8978	High Similarity	NPC82225
0.8978	High Similarity	NPC159623
0.8978	High Similarity	NPC28753
0.8978	High Similarity	NPC192304
0.8978	High Similarity	NPC204960
0.8978	High Similarity	NPC139813
0.8978	High Similarity	NPC175098
0.8978	High Similarity	NPC223457
0.8978	High Similarity	NPC20560
0.8978	High Similarity	NPC188646
0.8973	High Similarity	NPC471676
0.8973	High Similarity	NPC244577
0.8973	High Similarity	NPC472422
0.8973	High Similarity	NPC472420
0.8973	High Similarity	NPC263384
0.8971	High Similarity	NPC313618
0.8966	High Similarity	NPC89442
0.8966	High Similarity	NPC317492
0.8958	High Similarity	NPC473077
0.8958	High Similarity	NPC202494
0.8958	High Similarity	NPC201731
0.8958	High Similarity	NPC97716
0.8958	High Similarity	NPC104406
0.8958	High Similarity	NPC237635
0.8958	High Similarity	NPC110303
0.8958	High Similarity	NPC296998
0.8958	High Similarity	NPC79469
0.8958	High Similarity	NPC23728
0.8958	High Similarity	NPC24673
0.8951	High Similarity	NPC124780
0.8951	High Similarity	NPC476055
0.8951	High Similarity	NPC209040
0.8951	High Similarity	NPC234629
0.8951	High Similarity	NPC87486
0.8951	High Similarity	NPC311741
0.8944	High Similarity	NPC226636
0.8944	High Similarity	NPC73028
0.8944	High Similarity	NPC162476
0.8944	High Similarity	NPC11561
0.8936	High Similarity	NPC6407
0.8936	High Similarity	NPC188243
0.8936	High Similarity	NPC110228
0.8929	High Similarity	NPC124269
0.8929	High Similarity	NPC131130
0.8929	High Similarity	NPC25427
0.8921	High Similarity	NPC477243
0.8921	High Similarity	NPC41461
0.8921	High Similarity	NPC477244
0.8921	High Similarity	NPC168105
0.8921	High Similarity	NPC213603
0.8921	High Similarity	NPC25287
0.8921	High Similarity	NPC470397
0.8921	High Similarity	NPC12165
0.8921	High Similarity	NPC249606
0.8921	High Similarity	NPC1486
0.8921	High Similarity	NPC98115
0.8921	High Similarity	NPC66349
0.8921	High Similarity	NPC477242
0.8921	High Similarity	NPC186838
0.8921	High Similarity	NPC150399
0.8921	High Similarity	NPC473391
0.8921	High Similarity	NPC472364
0.8921	High Similarity	NPC274109
0.8919	High Similarity	NPC470681
0.8913	High Similarity	NPC172262
0.8912	High Similarity	NPC256141
0.8912	High Similarity	NPC323626
0.8912	High Similarity	NPC470340
0.8912	High Similarity	NPC31627
0.8912	High Similarity	NPC285623
0.8912	High Similarity	NPC476238
0.8912	High Similarity	NPC327269
0.8912	High Similarity	NPC324233
0.8905	High Similarity	NPC205468
0.8905	High Similarity	NPC87231
0.8905	High Similarity	NPC257756
0.8905	High Similarity	NPC129132
0.8905	High Similarity	NPC182428
0.8905	High Similarity	NPC212631
0.8904	High Similarity	NPC472633
0.8904	High Similarity	NPC180351
0.8904	High Similarity	NPC239363
0.8897	High Similarity	NPC266572
0.8897	High Similarity	NPC218490
0.8897	High Similarity	NPC132592
0.8897	High Similarity	NPC10097
0.8897	High Similarity	NPC470460
0.8897	High Similarity	NPC160821
0.8889	High Similarity	NPC83357
0.8889	High Similarity	NPC470647
0.8889	High Similarity	NPC474302
0.8889	High Similarity	NPC470458
0.8889	High Similarity	NPC1940
0.8889	High Similarity	NPC124729
0.8889	High Similarity	NPC267375
0.8889	High Similarity	NPC246948

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 NPC201541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	919
0.2-0.3	1707
0.3-0.4	2619
0.4-0.5	1944
0.5-0.6	1082
0.6-0.7	333
0.7-0.8	112
0.8-0.85	39
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9407	High Similarity	NPD1510	Phase 2
0.9065	High Similarity	NPD1549	Phase 2
0.9034	High Similarity	NPD4380	Phase 2
0.8993	High Similarity	NPD1550	Clinical (unspecified phase)
0.8993	High Similarity	NPD1552	Clinical (unspecified phase)
0.8971	High Similarity	NPD1240	Approved
0.8841	High Similarity	NPD1607	Approved
0.8819	High Similarity	NPD4378	Clinical (unspecified phase)
0.8786	High Similarity	NPD2796	Approved
0.8675	High Similarity	NPD4381	Clinical (unspecified phase)
0.8562	High Similarity	NPD7410	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1511	Approved
0.8477	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1934	Approved
0.8403	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1512	Approved
0.8355	Intermediate Similarity	NPD2801	Approved
0.8312	Intermediate Similarity	NPD7075	Discontinued
0.8301	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD6801	Discontinued
0.8288	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD3818	Discontinued
0.8235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD7411	Suspended
0.8163	Intermediate Similarity	NPD3750	Approved
0.8138	Intermediate Similarity	NPD2935	Discontinued
0.8138	Intermediate Similarity	NPD1551	Phase 2
0.8121	Intermediate Similarity	NPD6799	Approved
0.8117	Intermediate Similarity	NPD7819	Suspended
0.8113	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6166	Phase 2
0.8113	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD5403	Approved
0.8075	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD5402	Approved
0.8056	Intermediate Similarity	NPD6651	Approved
0.8038	Intermediate Similarity	NPD6959	Discontinued
0.8013	Intermediate Similarity	NPD3882	Suspended
0.8013	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2800	Approved
0.7963	Intermediate Similarity	NPD7054	Approved
0.7962	Intermediate Similarity	NPD3749	Approved
0.7949	Intermediate Similarity	NPD3817	Phase 2
0.7947	Intermediate Similarity	NPD2534	Approved
0.7947	Intermediate Similarity	NPD2532	Approved
0.7947	Intermediate Similarity	NPD5401	Approved
0.7947	Intermediate Similarity	NPD2533	Approved
0.7922	Intermediate Similarity	NPD6599	Discontinued
0.7917	Intermediate Similarity	NPD943	Approved
0.7914	Intermediate Similarity	NPD7472	Approved
0.7914	Intermediate Similarity	NPD7074	Phase 3
0.7898	Intermediate Similarity	NPD7768	Phase 2
0.7888	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6797	Phase 2
0.7862	Intermediate Similarity	NPD5494	Approved
0.7852	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1243	Approved
0.7843	Intermediate Similarity	NPD920	Approved
0.7829	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD3748	Approved
0.7818	Intermediate Similarity	NPD7251	Discontinued
0.7815	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7808	Phase 3
0.777	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6232	Discontinued
0.7746	Intermediate Similarity	NPD2798	Approved
0.773	Intermediate Similarity	NPD7473	Discontinued
0.7711	Intermediate Similarity	NPD6559	Discontinued
0.7703	Intermediate Similarity	NPD7033	Discontinued
0.7682	Intermediate Similarity	NPD4628	Phase 3
0.7676	Intermediate Similarity	NPD1203	Approved
0.7665	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD2313	Discontinued
0.7651	Intermediate Similarity	NPD6100	Approved
0.7651	Intermediate Similarity	NPD6099	Approved
0.7651	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5844	Phase 1
0.7619	Intermediate Similarity	NPD230	Phase 1
0.7616	Intermediate Similarity	NPD2654	Approved
0.7609	Intermediate Similarity	NPD1548	Phase 1
0.76	Intermediate Similarity	NPD2344	Approved
0.7545	Intermediate Similarity	NPD5953	Discontinued
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.753	Intermediate Similarity	NPD7286	Phase 2
0.7518	Intermediate Similarity	NPD1610	Phase 2
0.7485	Intermediate Similarity	NPD1247	Approved
0.7482	Intermediate Similarity	NPD9545	Approved
0.7467	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2799	Discontinued
0.7465	Intermediate Similarity	NPD9717	Approved
0.7464	Intermediate Similarity	NPD9493	Approved
0.7451	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7432	Intermediate Similarity	NPD1613	Approved
0.7432	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4360	Phase 2
0.7429	Intermediate Similarity	NPD4363	Phase 3
0.7414	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2309	Approved
0.7397	Intermediate Similarity	NPD4908	Phase 1
0.7397	Intermediate Similarity	NPD6832	Phase 2
0.7394	Intermediate Similarity	NPD422	Phase 1
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5124	Phase 1
0.7383	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3751	Discontinued
0.7362	Intermediate Similarity	NPD919	Approved
0.7351	Intermediate Similarity	NPD4308	Phase 3
0.7347	Intermediate Similarity	NPD3027	Phase 3
0.7343	Intermediate Similarity	NPD3972	Approved
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.731	Intermediate Similarity	NPD1470	Approved
0.7297	Intermediate Similarity	NPD3268	Approved
0.7297	Intermediate Similarity	NPD3764	Approved
0.7297	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3226	Approved
0.729	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD1201	Approved
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1653	Approved
0.7229	Intermediate Similarity	NPD3787	Discontinued
0.7211	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2797	Approved
0.7192	Intermediate Similarity	NPD1164	Approved
0.7191	Intermediate Similarity	NPD4361	Phase 2
0.7191	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7458	Discontinued
0.7186	Intermediate Similarity	NPD3926	Phase 2
0.7181	Intermediate Similarity	NPD1296	Phase 2
0.7178	Intermediate Similarity	NPD4288	Approved
0.7174	Intermediate Similarity	NPD7584	Approved
0.7162	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD37	Approved
0.7152	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7127	Intermediate Similarity	NPD6778	Approved
0.7127	Intermediate Similarity	NPD6780	Approved
0.7127	Intermediate Similarity	NPD6776	Approved
0.7127	Intermediate Similarity	NPD6782	Approved
0.7127	Intermediate Similarity	NPD6781	Approved
0.7127	Intermediate Similarity	NPD6777	Approved
0.7127	Intermediate Similarity	NPD6779	Approved
0.7123	Intermediate Similarity	NPD3225	Approved
0.7122	Intermediate Similarity	NPD1241	Discontinued
0.7117	Intermediate Similarity	NPD5761	Phase 2
0.7117	Intermediate Similarity	NPD5760	Phase 2
0.7103	Intermediate Similarity	NPD9269	Phase 2
0.7099	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2861	Phase 2
0.7095	Intermediate Similarity	NPD9494	Approved
0.7086	Intermediate Similarity	NPD4307	Phase 2
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7081	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5408	Approved
0.7078	Intermediate Similarity	NPD5405	Approved
0.7078	Intermediate Similarity	NPD5406	Approved
0.7078	Intermediate Similarity	NPD5404	Approved
0.7076	Intermediate Similarity	NPD1729	Discontinued
0.7067	Intermediate Similarity	NPD411	Approved
0.7067	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9268	Approved
0.7055	Intermediate Similarity	NPD4749	Approved
0.7041	Intermediate Similarity	NPD2403	Approved
0.703	Intermediate Similarity	NPD4965	Approved
0.703	Intermediate Similarity	NPD4967	Phase 2
0.703	Intermediate Similarity	NPD4966	Approved
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.7011	Intermediate Similarity	NPD7696	Phase 3
0.7011	Intermediate Similarity	NPD7697	Approved
0.7011	Intermediate Similarity	NPD7435	Discontinued
0.7011	Intermediate Similarity	NPD7698	Approved
0.7007	Intermediate Similarity	NPD74	Approved
0.7007	Intermediate Similarity	NPD1876	Approved
0.7007	Intermediate Similarity	NPD9266	Approved
0.7006	Intermediate Similarity	NPD7003	Approved
0.7006	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4287	Approved
0.6994	Remote Similarity	NPD6104	Discontinued
0.6989	Remote Similarity	NPD8150	Discontinued
0.6987	Remote Similarity	NPD2424	Discontinued
0.6986	Remote Similarity	NPD1481	Phase 2
0.6986	Remote Similarity	NPD1608	Approved
0.6981	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7871	Phase 2
0.6973	Remote Similarity	NPD7870	Phase 2
0.6972	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3267	Approved
0.6959	Remote Similarity	NPD3266	Approved
0.6954	Remote Similarity	NPD6798	Discontinued
0.6946	Remote Similarity	NPD6234	Discontinued

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