NPASS Compound

Structure

NPC72958 OpenBabel07101718222D 21 23 0 0 1 0 0 0 0 0999 V2000 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 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 0.0000 -2.0000 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 2.5981 -1.5000 0.0000 C 0 0 1 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 -1.5000 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 -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 0.8660 -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 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 -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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 8 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 1 1 6 0 0 0 8 21 1 0 0 0 0 9 14 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 15 16 2 0 0 0 0 16 18 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	287.755
LogP:	3.655
LogD:	3.03
LogS:	-4.809
# Rotatable Bonds:	2
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.92
Synthetic Accessibility Score:	2.951
Fsp3:	0.312
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:	-4.602
MDCK Permeability:	3.8918798964004964e-05
Pgp-inhibitor:	0.173
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	87.78504180908203%
Volume Distribution (VD):	1.05
Pgp-substrate:	9.790506362915039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.897
CYP2C19-inhibitor:	0.674
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.579
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.817
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.509
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	10.997
Half-life (T1/2):	0.34

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.603
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.586
Rat Oral Acute Toxicity:	0.438
Maximum Recommended Daily Dose:	0.563
Skin Sensitization:	0.405
Carcinogencity:	0.835
Eye Corrosion:	0.004
Eye Irritation:	0.722
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC72958

Natural Product ID:	NPC72958
*Common Name:**	(2S)-5-Hydroxy-6,8-Dimethoxy-2-Methyl-2,3-Dihydrobenzo[G]Chromen-4-One
IUPAC Name:	(2S)-5-hydroxy-6,8-dimethoxy-2-methyl-2,3-dihydrobenzo[g]chromen-4-one
Synonyms:
Standard InCHIKey:	AHQXDHIRTWHABS-QMMMGPOBSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-8-4-11(17)15-13(21-8)6-9-5-10(19-2)7-12(20-3)14(9)16(15)18/h5-8,18H,4H2,1-3H3/t8-/m0/s1
SMILES:	C[C@H]1CC(=O)c2c(cc3cc(cc(c3c2O)OC)OC)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497723
PubChem CID:	10755767
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
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10869195]
NPO4343	Guanomyces polythrix	Species	n.a.	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	23000.0	nM	PMID[508198]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	87000.0	nM	PMID[508198]

☑ 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 NPC72958 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	393
0.1-0.2	1683
0.2-0.3	3825
0.3-0.4	9576
0.4-0.5	8857
0.5-0.6	3506
0.6-0.7	5237
0.7-0.8	5297
0.8-0.85	2411
0.85-0.9	1556
0.9-0.95	328
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC232645
0.9931	High Similarity	NPC87708
0.9726	High Similarity	NPC149526
0.9726	High Similarity	NPC474417
0.9724	High Similarity	NPC97029
0.9724	High Similarity	NPC100985
0.9724	High Similarity	NPC158338
0.9724	High Similarity	NPC288036
0.9724	High Similarity	NPC65589
0.9724	High Similarity	NPC97028
0.9655	High Similarity	NPC7025
0.9655	High Similarity	NPC256672
0.9655	High Similarity	NPC27221
0.9595	High Similarity	NPC210942
0.9595	High Similarity	NPC169990
0.9592	High Similarity	NPC478148
0.9586	High Similarity	NPC123202
0.9586	High Similarity	NPC7943
0.9586	High Similarity	NPC22005
0.9527	High Similarity	NPC40356
0.9527	High Similarity	NPC154683
0.9524	High Similarity	NPC202595
0.9524	High Similarity	NPC325983
0.9517	High Similarity	NPC290133
0.9517	High Similarity	NPC187282
0.9517	High Similarity	NPC24136
0.947	High Similarity	NPC85121
0.9463	High Similarity	NPC329844
0.9452	High Similarity	NPC34802
0.9444	High Similarity	NPC310340
0.9444	High Similarity	NPC84266
0.9396	High Similarity	NPC217447
0.9392	High Similarity	NPC470568
0.9379	High Similarity	NPC189650
0.9375	High Similarity	NPC96408
0.9375	High Similarity	NPC17170
0.9375	High Similarity	NPC156190
0.9375	High Similarity	NPC279650
0.9375	High Similarity	NPC94076
0.9375	High Similarity	NPC182255
0.9375	High Similarity	NPC258630
0.9375	High Similarity	NPC166689
0.9351	High Similarity	NPC197168
0.9346	High Similarity	NPC18380
0.9342	High Similarity	NPC195167
0.9333	High Similarity	NPC135522
0.9329	High Similarity	NPC470569
0.9329	High Similarity	NPC258249
0.9324	High Similarity	NPC233267
0.9324	High Similarity	NPC329933
0.9324	High Similarity	NPC291049
0.932	High Similarity	NPC300988
0.932	High Similarity	NPC10990
0.9315	High Similarity	NPC271288
0.9315	High Similarity	NPC470890
0.931	High Similarity	NPC194432
0.931	High Similarity	NPC296917
0.931	High Similarity	NPC227579
0.931	High Similarity	NPC64915
0.931	High Similarity	NPC167624
0.931	High Similarity	NPC166482
0.931	High Similarity	NPC73028
0.931	High Similarity	NPC107572
0.931	High Similarity	NPC10937
0.931	High Similarity	NPC76372
0.931	High Similarity	NPC223500
0.931	High Similarity	NPC78
0.931	High Similarity	NPC324436
0.931	High Similarity	NPC125855
0.931	High Similarity	NPC32739
0.931	High Similarity	NPC76338
0.931	High Similarity	NPC324134
0.931	High Similarity	NPC228504
0.931	High Similarity	NPC161506
0.931	High Similarity	NPC328164
0.931	High Similarity	NPC148757
0.931	High Similarity	NPC66515
0.931	High Similarity	NPC177354
0.931	High Similarity	NPC37496
0.931	High Similarity	NPC182852
0.931	High Similarity	NPC40833
0.931	High Similarity	NPC166934
0.931	High Similarity	NPC306829
0.931	High Similarity	NPC220998
0.931	High Similarity	NPC265040
0.931	High Similarity	NPC1089
0.9306	High Similarity	NPC275734
0.929	High Similarity	NPC25361
0.9286	High Similarity	NPC15374
0.9281	High Similarity	NPC292863
0.9281	High Similarity	NPC184326
0.9281	High Similarity	NPC470810
0.9276	High Similarity	NPC272196
0.9267	High Similarity	NPC273483
0.9267	High Similarity	NPC474843
0.9262	High Similarity	NPC227122
0.9262	High Similarity	NPC472633
0.9257	High Similarity	NPC105415
0.9257	High Similarity	NPC35150
0.9257	High Similarity	NPC106328
0.9252	High Similarity	NPC469758
0.9252	High Similarity	NPC472629
0.9252	High Similarity	NPC196114
0.9247	High Similarity	NPC478086
0.9247	High Similarity	NPC75049
0.9247	High Similarity	NPC221432
0.9247	High Similarity	NPC185276
0.9247	High Similarity	NPC175504
0.9247	High Similarity	NPC223812
0.9247	High Similarity	NPC107177
0.9247	High Similarity	NPC214166
0.9247	High Similarity	NPC85162
0.9247	High Similarity	NPC169591
0.9247	High Similarity	NPC164980
0.9247	High Similarity	NPC149026
0.9247	High Similarity	NPC77794
0.9247	High Similarity	NPC81697
0.9247	High Similarity	NPC278249
0.9247	High Similarity	NPC143896
0.9247	High Similarity	NPC125894
0.9247	High Similarity	NPC257097
0.9247	High Similarity	NPC150408
0.9247	High Similarity	NPC316816
0.9247	High Similarity	NPC39329
0.9247	High Similarity	NPC68104
0.9247	High Similarity	NPC91560
0.9247	High Similarity	NPC310130
0.9241	High Similarity	NPC312391
0.9241	High Similarity	NPC110038
0.9241	High Similarity	NPC324386
0.9241	High Similarity	NPC4743
0.9241	High Similarity	NPC213322
0.9241	High Similarity	NPC248372
0.9236	High Similarity	NPC140890
0.9231	High Similarity	NPC178851
0.9221	High Similarity	NPC137232
0.9216	High Similarity	NPC210459
0.9216	High Similarity	NPC186113
0.9211	High Similarity	NPC180924
0.9205	High Similarity	NPC472799
0.9205	High Similarity	NPC193200
0.92	High Similarity	NPC133856
0.9195	High Similarity	NPC473016
0.9195	High Similarity	NPC10027
0.9195	High Similarity	NPC65775
0.9189	High Similarity	NPC126767
0.9189	High Similarity	NPC56433
0.9189	High Similarity	NPC245584
0.9189	High Similarity	NPC473077
0.9189	High Similarity	NPC312929
0.9189	High Similarity	NPC308200
0.9189	High Similarity	NPC289042
0.9189	High Similarity	NPC71055
0.9189	High Similarity	NPC190648
0.9189	High Similarity	NPC118027
0.9189	High Similarity	NPC296998
0.9184	High Similarity	NPC209040
0.9184	High Similarity	NPC236766
0.9184	High Similarity	NPC473015
0.9184	High Similarity	NPC131568
0.9184	High Similarity	NPC473014
0.9184	High Similarity	NPC224714
0.9184	High Similarity	NPC131579
0.9184	High Similarity	NPC473013
0.9184	High Similarity	NPC87486
0.9184	High Similarity	NPC469764
0.9184	High Similarity	NPC124780
0.9184	High Similarity	NPC197252
0.9184	High Similarity	NPC235217
0.9172	High Similarity	NPC182421
0.9172	High Similarity	NPC188243
0.9172	High Similarity	NPC6407
0.9172	High Similarity	NPC110228
0.9167	High Similarity	NPC469664
0.9156	High Similarity	NPC186325
0.9156	High Similarity	NPC321399
0.9156	High Similarity	NPC299436
0.9156	High Similarity	NPC36217
0.915	High Similarity	NPC164110
0.915	High Similarity	NPC281137
0.915	High Similarity	NPC212967
0.915	High Similarity	NPC282390
0.915	High Similarity	NPC246647
0.915	High Similarity	NPC96342
0.915	High Similarity	NPC201127
0.9145	High Similarity	NPC149618
0.9145	High Similarity	NPC89625
0.9145	High Similarity	NPC67396
0.9139	High Similarity	NPC106976
0.9133	High Similarity	NPC255641
0.9133	High Similarity	NPC37348
0.9133	High Similarity	NPC150928
0.9133	High Similarity	NPC147735
0.9133	High Similarity	NPC290954
0.9128	High Similarity	NPC39195
0.9128	High Similarity	NPC145467
0.9122	High Similarity	NPC301276
0.9122	High Similarity	NPC83357
0.9122	High Similarity	NPC214774
0.9122	High Similarity	NPC163846

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 NPC72958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	1018
0.2-0.3	1556
0.3-0.4	2593
0.4-0.5	1860
0.5-0.6	1080
0.6-0.7	464
0.7-0.8	163
0.8-0.85	37
0.85-0.9	20
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9346	High Similarity	NPD6959	Discontinued
0.9079	High Similarity	NPD7819	Suspended
0.9079	High Similarity	NPD2393	Clinical (unspecified phase)
0.8966	High Similarity	NPD1550	Clinical (unspecified phase)
0.8966	High Similarity	NPD1552	Clinical (unspecified phase)
0.8926	High Similarity	NPD4378	Clinical (unspecified phase)
0.8904	High Similarity	NPD1549	Phase 2
0.8896	High Similarity	NPD8443	Clinical (unspecified phase)
0.8766	High Similarity	NPD1934	Approved
0.8675	High Similarity	NPD2534	Approved
0.8675	High Similarity	NPD2533	Approved
0.8675	High Similarity	NPD2532	Approved
0.8662	High Similarity	NPD7075	Discontinued
0.8639	High Similarity	NPD2796	Approved
0.8636	High Similarity	NPD4380	Phase 2
0.859	High Similarity	NPD7096	Clinical (unspecified phase)
0.8581	High Similarity	NPD7411	Suspended
0.8571	High Similarity	NPD1510	Phase 2
0.8562	High Similarity	NPD1607	Approved
0.8562	High Similarity	NPD6232	Discontinued
0.8553	High Similarity	NPD7410	Clinical (unspecified phase)
0.8528	High Similarity	NPD5844	Phase 1
0.8523	High Similarity	NPD970	Clinical (unspecified phase)
0.8519	High Similarity	NPD7473	Discontinued
0.8457	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1240	Approved
0.8389	Intermediate Similarity	NPD6099	Approved
0.8389	Intermediate Similarity	NPD6100	Approved
0.8373	Intermediate Similarity	NPD6559	Discontinued
0.8366	Intermediate Similarity	NPD1511	Approved
0.8366	Intermediate Similarity	NPD7390	Discontinued
0.8365	Intermediate Similarity	NPD7768	Phase 2
0.8354	Intermediate Similarity	NPD2801	Approved
0.8344	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD5494	Approved
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3749	Approved
0.8291	Intermediate Similarity	NPD6801	Discontinued
0.8289	Intermediate Similarity	NPD3750	Approved
0.828	Intermediate Similarity	NPD6599	Discontinued
0.8258	Intermediate Similarity	NPD1512	Approved
0.825	Intermediate Similarity	NPD3882	Suspended
0.8224	Intermediate Similarity	NPD2800	Approved
0.8219	Intermediate Similarity	NPD4625	Phase 3
0.8217	Intermediate Similarity	NPD3226	Approved
0.8212	Intermediate Similarity	NPD2346	Discontinued
0.8193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1551	Phase 2
0.8144	Intermediate Similarity	NPD7074	Phase 3
0.8137	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6799	Approved
0.811	Intermediate Similarity	NPD5711	Approved
0.811	Intermediate Similarity	NPD5710	Approved
0.8105	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7054	Approved
0.8075	Intermediate Similarity	NPD3817	Phase 2
0.8052	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7472	Approved
0.8026	Intermediate Similarity	NPD2935	Discontinued
0.8024	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD1243	Approved
0.7962	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD3748	Approved
0.7947	Intermediate Similarity	NPD6651	Approved
0.7941	Intermediate Similarity	NPD7251	Discontinued
0.7935	Intermediate Similarity	NPD4628	Phase 3
0.7919	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1465	Phase 2
0.7895	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7808	Phase 3
0.7862	Intermediate Similarity	NPD920	Approved
0.7857	Intermediate Similarity	NPD2344	Approved
0.7843	Intermediate Similarity	NPD2799	Discontinued
0.7841	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD5406	Approved
0.7792	Intermediate Similarity	NPD5405	Approved
0.7792	Intermediate Similarity	NPD5408	Approved
0.7792	Intermediate Similarity	NPD5404	Approved
0.7791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4908	Phase 1
0.7778	Intermediate Similarity	NPD5953	Discontinued
0.775	Intermediate Similarity	NPD5403	Approved
0.7746	Intermediate Similarity	NPD8312	Approved
0.7746	Intermediate Similarity	NPD8313	Approved
0.7744	Intermediate Similarity	NPD5402	Approved
0.7736	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD919	Approved
0.7687	Intermediate Similarity	NPD4749	Approved
0.7682	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7229	Phase 3
0.7674	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1201	Approved
0.7671	Intermediate Similarity	NPD1610	Phase 2
0.7671	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7286	Phase 2
0.7658	Intermediate Similarity	NPD2309	Approved
0.7654	Intermediate Similarity	NPD4363	Phase 3
0.7654	Intermediate Similarity	NPD4360	Phase 2
0.7637	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3926	Phase 2
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD5401	Approved
0.7619	Intermediate Similarity	NPD1247	Approved
0.7602	Intermediate Similarity	NPD7177	Discontinued
0.7602	Intermediate Similarity	NPD3751	Discontinued
0.7595	Intermediate Similarity	NPD7003	Approved
0.7595	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD8151	Discontinued
0.7586	Intermediate Similarity	NPD1651	Approved
0.7584	Intermediate Similarity	NPD1470	Approved
0.7582	Intermediate Similarity	NPD943	Approved
0.7574	Intermediate Similarity	NPD3787	Discontinued
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7541	Intermediate Similarity	NPD6781	Approved
0.7541	Intermediate Similarity	NPD6780	Approved
0.7541	Intermediate Similarity	NPD6776	Approved
0.7541	Intermediate Similarity	NPD6779	Approved
0.7541	Intermediate Similarity	NPD6782	Approved
0.7541	Intermediate Similarity	NPD6778	Approved
0.7541	Intermediate Similarity	NPD6777	Approved
0.7532	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1283	Approved
0.7516	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7469	Intermediate Similarity	NPD6273	Approved
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1203	Approved
0.7455	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3268	Approved
0.7439	Intermediate Similarity	NPD7458	Discontinued
0.7434	Intermediate Similarity	NPD6832	Phase 2
0.7421	Intermediate Similarity	NPD7783	Phase 2
0.7421	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7698	Approved
0.7419	Intermediate Similarity	NPD7697	Approved
0.7419	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7696	Phase 3
0.7419	Intermediate Similarity	NPD5124	Phase 1
0.7419	Intermediate Similarity	NPD7435	Discontinued
0.7418	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4361	Phase 2
0.7417	Intermediate Similarity	NPD2798	Approved
0.7416	Intermediate Similarity	NPD8150	Discontinued
0.7412	Intermediate Similarity	NPD7199	Phase 2
0.7405	Intermediate Similarity	NPD1471	Phase 3
0.7399	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7389	Intermediate Similarity	NPD4308	Phase 3
0.7383	Intermediate Similarity	NPD1608	Approved
0.7383	Intermediate Similarity	NPD3972	Approved
0.738	Intermediate Similarity	NPD7870	Phase 2
0.738	Intermediate Similarity	NPD7871	Phase 2
0.7368	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2861	Phase 2
0.7355	Intermediate Similarity	NPD4060	Phase 1
0.7355	Intermediate Similarity	NPD2979	Phase 3
0.7351	Intermediate Similarity	NPD2797	Approved
0.7342	Intermediate Similarity	NPD2438	Suspended
0.7338	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD4287	Approved
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4288	Approved
0.732	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1281	Approved
0.7312	Intermediate Similarity	NPD2654	Approved
0.7308	Intermediate Similarity	NPD230	Phase 1
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7228	Approved
0.7297	Intermediate Similarity	NPD4626	Approved
0.7283	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6823	Phase 2
0.7268	Intermediate Similarity	NPD6535	Approved
0.7268	Intermediate Similarity	NPD6534	Approved
0.7267	Intermediate Similarity	NPD9717	Approved
0.7263	Intermediate Similarity	NPD7701	Phase 2
0.7262	Intermediate Similarity	NPD5761	Phase 2
0.7262	Intermediate Similarity	NPD5760	Phase 2
0.7233	Intermediate Similarity	NPD4476	Approved
0.7233	Intermediate Similarity	NPD4477	Approved
0.7232	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5691	Approved
0.7226	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD8434	Phase 2

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