NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	270.459
LogP:	2.629
LogD:	2.092
LogS:	-3.22
# Rotatable Bonds:	1
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.833
Synthetic Accessibility Score:	3.055
Fsp3:	0.267
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:	-4.741
MDCK Permeability:	1.6999039871734567e-05
Pgp-inhibitor:	0.227
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.459

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	88.27526092529297%
Volume Distribution (VD):	0.905
Pgp-substrate:	11.338027000427246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.71
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.372
CYP2C9-inhibitor:	0.269
CYP2C9-substrate:	0.794
CYP2D6-inhibitor:	0.617
CYP2D6-substrate:	0.344
CYP3A4-inhibitor:	0.286
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	3.38
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.579
Drug-inuced Liver Injury (DILI):	0.766
AMES Toxicity:	0.277
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.441
Skin Sensitization:	0.648
Carcinogencity:	0.855
Eye Corrosion:	0.003
Eye Irritation:	0.05
Respiratory Toxicity:	0.699

Download Data

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

Natural Product: NPC255133

Natural Product ID:	NPC255133
*Common Name:**	Greveichromenol
IUPAC Name:	5-hydroxy-8-(hydroxymethyl)-2,2-dimethylpyrano[3,2-g]chromen-6-one
Synonyms:	Greveichromenol
Standard InCHIKey:	MJSXHUBIQAPDNC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-15(2)4-3-9-11(20-15)6-12-13(14(9)18)10(17)5-8(7-16)19-12/h3-6,16,18H,7H2,1-2H3
SMILES:	CC1(C)C=Cc2c(cc3c(c(=O)cc(CO)o3)c2O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204368
PubChem CID:	71450427
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO19141	Aframomum melegueta	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22789014]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO8415	Tetragonotheca ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3089	Cistus villosus	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO470	Prismatomeris connata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19141	Aframomum melegueta	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3435	Saussurea katochaete	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6728	Rubus niveus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3268	Callyspongia flammea	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7941	Marshallia obovata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1953	Miltochrista calamina	Species	Erebidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3848	Myrtopsis macrocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1513	Penicillium nalgiovense	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4821	Hypselodoris infucata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4194	Teucrium buxifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8415	Tetragonotheca ludoviciana	Species	Asteraceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	50.0	ug.mL-1	PMID[476893]

☑ 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 NPC255133 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	386
0.1-0.2	1650
0.2-0.3	4248
0.3-0.4	10425
0.4-0.5	7815
0.5-0.6	4036
0.6-0.7	5707
0.7-0.8	4280
0.8-0.85	2363
0.85-0.9	1604
0.9-0.95	175
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC242100
0.9708	High Similarity	NPC471697
0.9565	High Similarity	NPC473076
0.9507	High Similarity	NPC85773
0.9424	High Similarity	NPC23257
0.9416	High Similarity	NPC60667
0.9375	High Similarity	NPC472628
0.9371	High Similarity	NPC472627
0.9371	High Similarity	NPC202494
0.9366	High Similarity	NPC297788
0.9357	High Similarity	NPC471587
0.9343	High Similarity	NPC125920
0.932	High Similarity	NPC470681
0.9315	High Similarity	NPC285623
0.9306	High Similarity	NPC6511
0.9306	High Similarity	NPC10097
0.9301	High Similarity	NPC474302
0.9286	High Similarity	NPC18260
0.9286	High Similarity	NPC139554
0.9286	High Similarity	NPC78913
0.9281	High Similarity	NPC160972
0.9275	High Similarity	NPC151113
0.927	High Similarity	NPC93756
0.927	High Similarity	NPC108113
0.927	High Similarity	NPC223457
0.9252	High Similarity	NPC223701
0.9252	High Similarity	NPC7989
0.9252	High Similarity	NPC472583
0.9247	High Similarity	NPC263384
0.9247	High Similarity	NPC244577
0.9247	High Similarity	NPC472422
0.9247	High Similarity	NPC472420
0.9247	High Similarity	NPC471676
0.9247	High Similarity	NPC471677
0.9247	High Similarity	NPC471675
0.9241	High Similarity	NPC5173
0.9241	High Similarity	NPC139966
0.9241	High Similarity	NPC307052
0.9236	High Similarity	NPC47388
0.9236	High Similarity	NPC104406
0.9236	High Similarity	NPC97716
0.9236	High Similarity	NPC473133
0.9236	High Similarity	NPC201731
0.9236	High Similarity	NPC470670
0.9236	High Similarity	NPC79469
0.9236	High Similarity	NPC91902
0.9236	High Similarity	NPC237635
0.9236	High Similarity	NPC24673
0.9231	High Similarity	NPC319752
0.9225	High Similarity	NPC59739
0.9225	High Similarity	NPC293852
0.9225	High Similarity	NPC226636
0.9225	High Similarity	NPC162476
0.9225	High Similarity	NPC299080
0.9225	High Similarity	NPC11561
0.9225	High Similarity	NPC217083
0.9225	High Similarity	NPC78803
0.9225	High Similarity	NPC214236
0.9225	High Similarity	NPC62840
0.922	High Similarity	NPC150522
0.922	High Similarity	NPC159275
0.922	High Similarity	NPC241100
0.9214	High Similarity	NPC470668
0.9214	High Similarity	NPC201395
0.9214	High Similarity	NPC131130
0.9214	High Similarity	NPC470669
0.9209	High Similarity	NPC174999
0.9189	High Similarity	NPC259710
0.9189	High Similarity	NPC87404
0.9189	High Similarity	NPC207809
0.9189	High Similarity	NPC217706
0.9189	High Similarity	NPC304207
0.9189	High Similarity	NPC48579
0.9189	High Similarity	NPC92395
0.9184	High Similarity	NPC476238
0.9184	High Similarity	NPC327269
0.9184	High Similarity	NPC475790
0.9184	High Similarity	NPC161881
0.9184	High Similarity	NPC256141
0.9184	High Similarity	NPC244583
0.9184	High Similarity	NPC56232
0.9184	High Similarity	NPC150123
0.9184	High Similarity	NPC31627
0.9184	High Similarity	NPC10807
0.9172	High Similarity	NPC161191
0.9172	High Similarity	NPC211811
0.9172	High Similarity	NPC321623
0.9172	High Similarity	NPC189087
0.9172	High Similarity	NPC266572
0.9167	High Similarity	NPC111786
0.9167	High Similarity	NPC301276
0.9167	High Similarity	NPC214774
0.9167	High Similarity	NPC475052
0.9167	High Similarity	NPC20488
0.9167	High Similarity	NPC312973
0.9167	High Similarity	NPC83357
0.9167	High Similarity	NPC195621
0.9167	High Similarity	NPC267375
0.9167	High Similarity	NPC474161
0.9167	High Similarity	NPC54577
0.9167	High Similarity	NPC246948
0.9167	High Similarity	NPC142405
0.9167	High Similarity	NPC67805
0.9167	High Similarity	NPC176229
0.9167	High Similarity	NPC470647
0.9167	High Similarity	NPC476088
0.9167	High Similarity	NPC88964
0.9161	High Similarity	NPC214166
0.9161	High Similarity	NPC478086
0.9161	High Similarity	NPC316816
0.9155	High Similarity	NPC64908
0.9155	High Similarity	NPC4743
0.9155	High Similarity	NPC147688
0.9155	High Similarity	NPC282300
0.9155	High Similarity	NPC3188
0.9155	High Similarity	NPC324386
0.9155	High Similarity	NPC213322
0.9155	High Similarity	NPC103362
0.9155	High Similarity	NPC205006
0.9155	High Similarity	NPC156590
0.9155	High Similarity	NPC118840
0.9155	High Similarity	NPC110969
0.9155	High Similarity	NPC312391
0.9149	High Similarity	NPC303633
0.9149	High Similarity	NPC96565
0.9149	High Similarity	NPC53181
0.9149	High Similarity	NPC216978
0.9149	High Similarity	NPC220062
0.9149	High Similarity	NPC55018
0.9149	High Similarity	NPC217186
0.9149	High Similarity	NPC301217
0.9137	High Similarity	NPC46869
0.9137	High Similarity	NPC101752
0.9124	High Similarity	NPC473584
0.9124	High Similarity	NPC31872
0.9124	High Similarity	NPC475589
0.9122	High Similarity	NPC469405
0.9122	High Similarity	NPC248793
0.9122	High Similarity	NPC180301
0.9116	High Similarity	NPC328740
0.9116	High Similarity	NPC474023
0.9116	High Similarity	NPC472580
0.9116	High Similarity	NPC289774
0.9116	High Similarity	NPC474772
0.9116	High Similarity	NPC477897
0.9116	High Similarity	NPC472423
0.9116	High Similarity	NPC81474
0.9116	High Similarity	NPC474021
0.9116	High Similarity	NPC209846
0.9116	High Similarity	NPC262039
0.9116	High Similarity	NPC472636
0.9116	High Similarity	NPC254412
0.9116	High Similarity	NPC319910
0.9116	High Similarity	NPC278476
0.9116	High Similarity	NPC262038
0.9116	High Similarity	NPC474744
0.9103	High Similarity	NPC211466
0.9103	High Similarity	NPC296998
0.9103	High Similarity	NPC3779
0.9103	High Similarity	NPC476182
0.9103	High Similarity	NPC472918
0.9103	High Similarity	NPC110303
0.9103	High Similarity	NPC283234
0.9103	High Similarity	NPC44721
0.9103	High Similarity	NPC473077
0.9103	High Similarity	NPC176869
0.9103	High Similarity	NPC40086
0.9103	High Similarity	NPC222298
0.9103	High Similarity	NPC51070
0.9103	High Similarity	NPC122828
0.9103	High Similarity	NPC129650
0.9103	High Similarity	NPC23728
0.9097	High Similarity	NPC62290
0.9097	High Similarity	NPC49130
0.9097	High Similarity	NPC4152
0.9097	High Similarity	NPC131568
0.9097	High Similarity	NPC234629
0.9097	High Similarity	NPC326506
0.9097	High Similarity	NPC208176
0.9097	High Similarity	NPC311741
0.9097	High Similarity	NPC142731
0.9097	High Similarity	NPC209040
0.9097	High Similarity	NPC279417
0.9097	High Similarity	NPC224714
0.9097	High Similarity	NPC306607
0.9097	High Similarity	NPC131579
0.9091	High Similarity	NPC148757
0.9091	High Similarity	NPC306829
0.9091	High Similarity	NPC265040
0.9091	High Similarity	NPC166934
0.9091	High Similarity	NPC1089
0.9091	High Similarity	NPC125855
0.9091	High Similarity	NPC177354
0.9091	High Similarity	NPC324134
0.9091	High Similarity	NPC167624
0.9091	High Similarity	NPC107572
0.9091	High Similarity	NPC76372
0.9091	High Similarity	NPC161506
0.9091	High Similarity	NPC32739
0.9091	High Similarity	NPC227579

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 NPC255133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	933
0.2-0.3	1711
0.3-0.4	2698
0.4-0.5	1876
0.5-0.6	1043
0.6-0.7	363
0.7-0.8	125
0.8-0.85	36
0.85-0.9	16
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9007	High Similarity	NPD1550	Clinical (unspecified phase)
0.9007	High Similarity	NPD1552	Clinical (unspecified phase)
0.8966	High Similarity	NPD4378	Clinical (unspecified phase)
0.8944	High Similarity	NPD1549	Phase 2
0.8919	High Similarity	NPD4380	Phase 2
0.8865	High Similarity	NPD1510	Phase 2
0.8836	High Similarity	NPD7410	Clinical (unspecified phase)
0.88	High Similarity	NPD6801	Discontinued
0.8742	High Similarity	NPD2393	Clinical (unspecified phase)
0.8714	High Similarity	NPD1240	Approved
0.8693	High Similarity	NPD7075	Discontinued
0.8675	High Similarity	NPD1934	Approved
0.8639	High Similarity	NPD1511	Approved
0.8618	High Similarity	NPD7096	Clinical (unspecified phase)
0.8592	High Similarity	NPD1607	Approved
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8542	High Similarity	NPD2796	Approved
0.8523	High Similarity	NPD1512	Approved
0.8514	High Similarity	NPD6799	Approved
0.8497	Intermediate Similarity	NPD2801	Approved
0.8487	Intermediate Similarity	NPD7411	Suspended
0.8442	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5403	Approved
0.8333	Intermediate Similarity	NPD5401	Approved
0.8301	Intermediate Similarity	NPD6599	Discontinued
0.8299	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD3882	Suspended
0.8258	Intermediate Similarity	NPD7819	Suspended
0.825	Intermediate Similarity	NPD6166	Phase 2
0.825	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2800	Approved
0.8205	Intermediate Similarity	NPD3817	Phase 2
0.8148	Intermediate Similarity	NPD3818	Discontinued
0.8121	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1243	Approved
0.8105	Intermediate Similarity	NPD920	Approved
0.8098	Intermediate Similarity	NPD7054	Approved
0.8082	Intermediate Similarity	NPD6651	Approved
0.8079	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3750	Approved
0.8067	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7074	Phase 3
0.8049	Intermediate Similarity	NPD7472	Approved
0.8041	Intermediate Similarity	NPD1551	Phase 2
0.8038	Intermediate Similarity	NPD7768	Phase 2
0.8025	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7975	Intermediate Similarity	NPD5402	Approved
0.7974	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7251	Discontinued
0.7952	Intermediate Similarity	NPD6559	Discontinued
0.795	Intermediate Similarity	NPD6959	Discontinued
0.7937	Intermediate Similarity	NPD919	Approved
0.7931	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7808	Phase 3
0.7891	Intermediate Similarity	NPD5124	Phase 1
0.7891	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5494	Approved
0.7875	Intermediate Similarity	NPD3749	Approved
0.7857	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD2534	Approved
0.7857	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD1247	Approved
0.7829	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD422	Phase 1
0.7798	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6232	Discontinued
0.777	Intermediate Similarity	NPD1548	Phase 1
0.7758	Intermediate Similarity	NPD7473	Discontinued
0.7746	Intermediate Similarity	NPD9717	Approved
0.7733	Intermediate Similarity	NPD3748	Approved
0.7733	Intermediate Similarity	NPD7033	Discontinued
0.7708	Intermediate Similarity	NPD1203	Approved
0.7703	Intermediate Similarity	NPD943	Approved
0.7687	Intermediate Similarity	NPD2313	Discontinued
0.7682	Intermediate Similarity	NPD2935	Discontinued
0.7679	Intermediate Similarity	NPD5953	Discontinued
0.7676	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5844	Phase 1
0.7665	Intermediate Similarity	NPD7286	Phase 2
0.7632	Intermediate Similarity	NPD2344	Approved
0.7616	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2799	Discontinued
0.7584	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1613	Approved
0.7568	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6099	Approved
0.7566	Intermediate Similarity	NPD6100	Approved
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7533	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD1652	Phase 2
0.7518	Intermediate Similarity	NPD9545	Approved
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1465	Phase 2
0.7468	Intermediate Similarity	NPD2424	Discontinued
0.7458	Intermediate Similarity	NPD4360	Phase 2
0.7458	Intermediate Similarity	NPD4363	Phase 3
0.745	Intermediate Similarity	NPD1296	Phase 2
0.745	Intermediate Similarity	NPD3268	Approved
0.7438	Intermediate Similarity	NPD3226	Approved
0.7436	Intermediate Similarity	NPD2309	Approved
0.7432	Intermediate Similarity	NPD6832	Phase 2
0.7432	Intermediate Similarity	NPD4908	Phase 1
0.7432	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2654	Approved
0.7417	Intermediate Similarity	NPD447	Suspended
0.7416	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4361	Phase 2
0.7412	Intermediate Similarity	NPD1729	Discontinued
0.741	Intermediate Similarity	NPD1241	Discontinued
0.7397	Intermediate Similarity	NPD3225	Approved
0.7391	Intermediate Similarity	NPD7584	Approved
0.7386	Intermediate Similarity	NPD4308	Phase 3
0.7376	Intermediate Similarity	NPD9493	Approved
0.7365	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2797	Approved
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6798	Discontinued
0.7321	Intermediate Similarity	NPD3926	Phase 2
0.7303	Intermediate Similarity	NPD1933	Approved
0.7297	Intermediate Similarity	NPD2798	Approved
0.7297	Intermediate Similarity	NPD1019	Discontinued
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.729	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5710	Approved
0.7262	Intermediate Similarity	NPD5711	Approved
0.7248	Intermediate Similarity	NPD9494	Approved
0.7239	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7390	Discontinued
0.723	Intermediate Similarity	NPD3266	Approved
0.723	Intermediate Similarity	NPD3267	Approved
0.7222	Intermediate Similarity	NPD7458	Discontinued
0.7219	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD411	Approved
0.7215	Intermediate Similarity	NPD2354	Approved
0.7205	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7199	Phase 2
0.7188	Intermediate Similarity	NPD4661	Approved
0.7188	Intermediate Similarity	NPD4662	Approved
0.7176	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2403	Approved
0.7162	Intermediate Similarity	NPD8651	Approved
0.716	Intermediate Similarity	NPD3787	Discontinued
0.716	Intermediate Similarity	NPD1653	Approved
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7143	Intermediate Similarity	NPD8312	Approved
0.7126	Intermediate Similarity	NPD6104	Discontinued
0.7124	Intermediate Similarity	NPD4307	Phase 2
0.7119	Intermediate Similarity	NPD8434	Phase 2
0.7108	Intermediate Similarity	NPD4288	Approved
0.7101	Intermediate Similarity	NPD290	Approved
0.7095	Intermediate Similarity	NPD4749	Approved
0.7086	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6355	Discontinued
0.7075	Intermediate Similarity	NPD1201	Approved
0.7075	Intermediate Similarity	NPD1091	Approved
0.7069	Intermediate Similarity	NPD3823	Discontinued
0.7065	Intermediate Similarity	NPD6780	Approved
0.7065	Intermediate Similarity	NPD6778	Approved
0.7065	Intermediate Similarity	NPD6781	Approved
0.7065	Intermediate Similarity	NPD6782	Approved
0.7065	Intermediate Similarity	NPD6777	Approved
0.7065	Intermediate Similarity	NPD6776	Approved
0.7065	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.705	Intermediate Similarity	NPD2684	Approved
0.7048	Intermediate Similarity	NPD8455	Phase 2
0.703	Intermediate Similarity	NPD5889	Approved
0.703	Intermediate Similarity	NPD5890	Approved
0.7027	Intermediate Similarity	NPD3972	Approved
0.7019	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4060	Phase 1
0.7012	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1470	Approved
0.7	Intermediate Similarity	NPD3887	Approved
0.7	Intermediate Similarity	NPD1164	Approved
0.6993	Remote Similarity	NPD3764	Approved
0.6984	Remote Similarity	NPD7585	Approved
0.6972	Remote Similarity	NPD7843	Approved
0.697	Remote Similarity	NPD6585	Discontinued
0.6962	Remote Similarity	NPD6002	Phase 3
0.6962	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1471	Phase 3
0.6962	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2355	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