NPASS Compound

Structure

CID206212 OpenBabel06191715592D 24 26 0 0 0 0 0 0 0 0999 V2000 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 6 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 6 18 1 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 20 2 0 0 0 0 12 21 2 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.13
Volume:	337.007
LogP:	4.132
LogD:	3.012
LogS:	-4.147
# Rotatable Bonds:	2
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	3.224
Fsp3:	0.368
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:	-4.655
MDCK Permeability:	2.7116357159684412e-05
Pgp-inhibitor:	0.833
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	88.42606353759766%
Volume Distribution (VD):	1.144
Pgp-substrate:	9.788082122802734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.869
CYP1A2-substrate:	0.776
CYP2C19-inhibitor:	0.773
CYP2C19-substrate:	0.222
CYP2C9-inhibitor:	0.797
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.678
CYP2D6-substrate:	0.432
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	1.796
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.897
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.29
Carcinogencity:	0.904
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.504

Download Data

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

Natural Product: NPC206212

Natural Product ID:	NPC206212
*Common Name:**	5-Hydroxy-2,2-Dimethyl-10-(2-Methylbut-3-En-2-Yl)-3H-Pyrano[3,2-G]Chromene-4,8-Dione
IUPAC Name:	5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-3H-pyrano[3,2-g]chromene-4,8-dione
Synonyms:
Standard InCHIKey:	RDROOFQFFWIIDK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O5/c1-6-18(2,3)14-16-10(7-8-12(21)23-16)15(22)13-11(20)9-19(4,5)24-17(13)14/h6-8,22H,1,9H2,2-5H3
SMILES:	C=CC(c1c2OC(C)(C)CC(=O)c2c(c2c1oc(=O)cc2)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL423237
PubChem CID:	5315947
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003486] Linear pyranocoumarins

*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
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000023]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19266	Clausena excavata	Species	Rutaceae	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
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	200.0	ug.mL-1	PMID[506987]

☑ 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 NPC206212 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	384
0.1-0.2	1719
0.2-0.3	4034
0.3-0.4	10032
0.4-0.5	8633
0.5-0.6	4192
0.6-0.7	6004
0.7-0.8	5067
0.8-0.85	1728
0.85-0.9	769
0.9-0.95	123
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC71184
0.9441	High Similarity	NPC474108
0.9441	High Similarity	NPC177995
0.9429	High Similarity	NPC221173
0.942	High Similarity	NPC470982
0.942	High Similarity	NPC470983
0.9362	High Similarity	NPC470555
0.9357	High Similarity	NPC472343
0.9306	High Similarity	NPC140120
0.9286	High Similarity	NPC199458
0.9286	High Similarity	NPC183639
0.922	High Similarity	NPC19476
0.922	High Similarity	NPC241975
0.9214	High Similarity	NPC138047
0.9214	High Similarity	NPC131782
0.9214	High Similarity	NPC474624
0.9172	High Similarity	NPC180477
0.9172	High Similarity	NPC285748
0.9167	High Similarity	NPC1886
0.9167	High Similarity	NPC196137
0.9167	High Similarity	NPC469953
0.9161	High Similarity	NPC36181
0.9149	High Similarity	NPC268178
0.9149	High Similarity	NPC54820
0.9149	High Similarity	NPC470083
0.9149	High Similarity	NPC180501
0.9149	High Similarity	NPC219584
0.911	High Similarity	NPC161864
0.911	High Similarity	NPC208303
0.9103	High Similarity	NPC181388
0.9103	High Similarity	NPC470322
0.9103	High Similarity	NPC57470
0.9103	High Similarity	NPC154217
0.9097	High Similarity	NPC470296
0.9097	High Similarity	NPC87609
0.9097	High Similarity	NPC11700
0.9097	High Similarity	NPC94794
0.9097	High Similarity	NPC196459
0.9097	High Similarity	NPC188632
0.9097	High Similarity	NPC112791
0.9091	High Similarity	NPC316560
0.9091	High Similarity	NPC316911
0.9078	High Similarity	NPC38153
0.9071	High Similarity	NPC101752
0.9048	High Similarity	NPC469932
0.9041	High Similarity	NPC249942
0.9041	High Similarity	NPC297886
0.9034	High Similarity	NPC470673
0.9034	High Similarity	NPC469935
0.9034	High Similarity	NPC117716
0.9034	High Similarity	NPC178627
0.9034	High Similarity	NPC470674
0.9028	High Similarity	NPC294432
0.9028	High Similarity	NPC144499
0.9028	High Similarity	NPC470556
0.9028	High Similarity	NPC321148
0.9028	High Similarity	NPC112829
0.9028	High Similarity	NPC321629
0.9028	High Similarity	NPC323884
0.9028	High Similarity	NPC326193
0.9014	High Similarity	NPC248995
0.9014	High Similarity	NPC272844
0.9014	High Similarity	NPC254168
0.8993	High Similarity	NPC83535
0.8986	High Similarity	NPC180351
0.8986	High Similarity	NPC151973
0.898	High Similarity	NPC469933
0.8973	High Similarity	NPC477955
0.8966	High Similarity	NPC96216
0.8966	High Similarity	NPC470909
0.8966	High Similarity	NPC18585
0.8966	High Similarity	NPC219915
0.8966	High Similarity	NPC470553
0.8966	High Similarity	NPC166138
0.8966	High Similarity	NPC184738
0.8966	High Similarity	NPC38219
0.8966	High Similarity	NPC33653
0.8966	High Similarity	NPC307895
0.8966	High Similarity	NPC474939
0.8966	High Similarity	NPC106985
0.8958	High Similarity	NPC147688
0.8958	High Similarity	NPC64908
0.8958	High Similarity	NPC156590
0.8958	High Similarity	NPC118840
0.8958	High Similarity	NPC205006
0.8951	High Similarity	NPC270913
0.8951	High Similarity	NPC240305
0.8944	High Similarity	NPC332594
0.8926	High Similarity	NPC312549
0.8926	High Similarity	NPC305965
0.8926	High Similarity	NPC209142
0.8919	High Similarity	NPC164205
0.8919	High Similarity	NPC104236
0.8919	High Similarity	NPC19238
0.8912	High Similarity	NPC300988
0.8912	High Similarity	NPC10990
0.8904	High Similarity	NPC311741
0.8904	High Similarity	NPC470554
0.8904	High Similarity	NPC133060
0.8904	High Similarity	NPC288910
0.8904	High Similarity	NPC234629
0.8904	High Similarity	NPC118059
0.8897	High Similarity	NPC11561
0.8897	High Similarity	NPC226636
0.8889	High Similarity	NPC289660
0.8889	High Similarity	NPC235239
0.8889	High Similarity	NPC475680
0.8889	High Similarity	NPC270883
0.8889	High Similarity	NPC477272
0.8889	High Similarity	NPC164697
0.8889	High Similarity	NPC172986
0.8889	High Similarity	NPC305355
0.8889	High Similarity	NPC261227
0.8889	High Similarity	NPC82920
0.8889	High Similarity	NPC69769
0.8881	High Similarity	NPC470671
0.8881	High Similarity	NPC474487
0.8881	High Similarity	NPC470669
0.8881	High Similarity	NPC470672
0.8881	High Similarity	NPC474504
0.8881	High Similarity	NPC131130
0.8881	High Similarity	NPC470668
0.8874	High Similarity	NPC469934
0.8867	High Similarity	NPC256141
0.8859	High Similarity	NPC158866
0.8859	High Similarity	NPC474735
0.8859	High Similarity	NPC188403
0.8857	High Similarity	NPC470988
0.8851	High Similarity	NPC37139
0.8851	High Similarity	NPC211811
0.8849	High Similarity	NPC37009
0.8849	High Similarity	NPC66430
0.8844	High Similarity	NPC470910
0.8844	High Similarity	NPC82534
0.8836	High Similarity	NPC5990
0.8828	High Similarity	NPC201820
0.8828	High Similarity	NPC110969
0.8828	High Similarity	NPC103362
0.8828	High Similarity	NPC111201
0.8819	High Similarity	NPC473209
0.8819	High Similarity	NPC53181
0.8819	High Similarity	NPC96565
0.8819	High Similarity	NPC216978
0.8819	High Similarity	NPC472515
0.8819	High Similarity	NPC473076
0.8819	High Similarity	NPC220062
0.8819	High Similarity	NPC217186
0.8819	High Similarity	NPC303633
0.8819	High Similarity	NPC23257
0.8819	High Similarity	NPC301217
0.8819	High Similarity	NPC55018
0.8816	High Similarity	NPC4547
0.8811	High Similarity	NPC253616
0.8803	High Similarity	NPC151113
0.88	High Similarity	NPC290671
0.8794	High Similarity	NPC470984
0.8792	High Similarity	NPC471114
0.8792	High Similarity	NPC65775
0.8792	High Similarity	NPC10027
0.8784	High Similarity	NPC296998
0.8784	High Similarity	NPC473077
0.8784	High Similarity	NPC104406
0.8784	High Similarity	NPC79469
0.8784	High Similarity	NPC201731
0.8784	High Similarity	NPC97716
0.8784	High Similarity	NPC23728
0.8784	High Similarity	NPC110303
0.8784	High Similarity	NPC24673
0.8784	High Similarity	NPC237635
0.8777	High Similarity	NPC470987
0.8777	High Similarity	NPC21378
0.8776	High Similarity	NPC271288
0.8776	High Similarity	NPC278175
0.8776	High Similarity	NPC209040
0.8776	High Similarity	NPC476055
0.8776	High Similarity	NPC257236
0.8774	High Similarity	NPC473022
0.8767	High Similarity	NPC214236
0.8767	High Similarity	NPC299080
0.8767	High Similarity	NPC217083
0.8767	High Similarity	NPC266725
0.8767	High Similarity	NPC62840
0.8767	High Similarity	NPC78803
0.8767	High Similarity	NPC293852
0.8767	High Similarity	NPC472344
0.8767	High Similarity	NPC59739
0.8759	High Similarity	NPC150522
0.8759	High Similarity	NPC11056
0.8759	High Similarity	NPC241100
0.8759	High Similarity	NPC469818
0.8759	High Similarity	NPC471587
0.8759	High Similarity	NPC159275
0.8758	High Similarity	NPC270044
0.875	High Similarity	NPC36414
0.875	High Similarity	NPC473988
0.875	High Similarity	NPC201395
0.875	High Similarity	NPC108937
0.875	High Similarity	NPC279218
0.8741	High Similarity	NPC174999
0.8741	High Similarity	NPC268081

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 NPC206212 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	991
0.2-0.3	1696
0.3-0.4	2617
0.4-0.5	1966
0.5-0.6	1042
0.6-0.7	328
0.7-0.8	115
0.8-0.85	36
0.85-0.9	8
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8819	High Similarity	NPD2800	Approved
0.8776	High Similarity	NPD7410	Clinical (unspecified phase)
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8562	High Similarity	NPD7819	Suspended
0.8553	High Similarity	NPD7411	Suspended
0.8516	High Similarity	NPD7075	Discontinued
0.8442	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD6651	Approved
0.8397	Intermediate Similarity	NPD3749	Approved
0.8378	Intermediate Similarity	NPD3750	Approved
0.8377	Intermediate Similarity	NPD6801	Discontinued
0.8367	Intermediate Similarity	NPD1549	Phase 2
0.8313	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1243	Approved
0.8299	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1510	Phase 2
0.8278	Intermediate Similarity	NPD2534	Approved
0.8278	Intermediate Similarity	NPD2532	Approved
0.8278	Intermediate Similarity	NPD2533	Approved
0.8269	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD4380	Phase 2
0.8247	Intermediate Similarity	NPD6599	Discontinued
0.8243	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2796	Approved
0.8217	Intermediate Similarity	NPD7768	Phase 2
0.8205	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD920	Approved
0.8138	Intermediate Similarity	NPD1240	Approved
0.8092	Intermediate Similarity	NPD6799	Approved
0.8082	Intermediate Similarity	NPD5124	Phase 1
0.8082	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3748	Approved
0.8041	Intermediate Similarity	NPD2799	Discontinued
0.8027	Intermediate Similarity	NPD1607	Approved
0.8026	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2313	Discontinued
0.7974	Intermediate Similarity	NPD1511	Approved
0.7922	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1934	Approved
0.7901	Intermediate Similarity	NPD6959	Discontinued
0.7895	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1512	Approved
0.7867	Intermediate Similarity	NPD6099	Approved
0.7867	Intermediate Similarity	NPD2935	Discontinued
0.7867	Intermediate Similarity	NPD1551	Phase 2
0.7867	Intermediate Similarity	NPD6100	Approved
0.7862	Intermediate Similarity	NPD2801	Approved
0.7834	Intermediate Similarity	NPD3226	Approved
0.7831	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD9717	Approved
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7812	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD1203	Approved
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7755	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3268	Approved
0.7746	Intermediate Similarity	NPD422	Phase 1
0.7744	Intermediate Similarity	NPD5711	Approved
0.7744	Intermediate Similarity	NPD5710	Approved
0.7744	Intermediate Similarity	NPD6232	Discontinued
0.7738	Intermediate Similarity	NPD5953	Discontinued
0.7725	Intermediate Similarity	NPD7286	Phase 2
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7711	Intermediate Similarity	NPD7473	Discontinued
0.7707	Intermediate Similarity	NPD5403	Approved
0.7682	Intermediate Similarity	NPD4308	Phase 3
0.7669	Intermediate Similarity	NPD919	Approved
0.7655	Intermediate Similarity	NPD2797	Approved
0.7654	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3882	Suspended
0.764	Intermediate Similarity	NPD1465	Phase 2
0.7622	Intermediate Similarity	NPD5494	Approved
0.7588	Intermediate Similarity	NPD6559	Discontinued
0.7582	Intermediate Similarity	NPD2344	Approved
0.758	Intermediate Similarity	NPD5401	Approved
0.756	Intermediate Similarity	NPD3818	Discontinued
0.7545	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6166	Phase 2
0.7544	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7486	Intermediate Similarity	NPD4287	Approved
0.7485	Intermediate Similarity	NPD5402	Approved
0.7483	Intermediate Similarity	NPD2798	Approved
0.7471	Intermediate Similarity	NPD7472	Approved
0.7471	Intermediate Similarity	NPD7074	Phase 3
0.7451	Intermediate Similarity	NPD7033	Discontinued
0.7451	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6797	Phase 2
0.7417	Intermediate Similarity	NPD4307	Phase 2
0.7415	Intermediate Similarity	NPD3266	Approved
0.7415	Intermediate Similarity	NPD3267	Approved
0.74	Intermediate Similarity	NPD411	Approved
0.74	Intermediate Similarity	NPD1296	Phase 2
0.74	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7389	Intermediate Similarity	NPD2309	Approved
0.7384	Intermediate Similarity	NPD7251	Discontinued
0.7378	Intermediate Similarity	NPD4288	Approved
0.7368	Intermediate Similarity	NPD447	Suspended
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3225	Approved
0.7346	Intermediate Similarity	NPD6585	Discontinued
0.7341	Intermediate Similarity	NPD7808	Phase 3
0.7325	Intermediate Similarity	NPD7003	Approved
0.729	Intermediate Similarity	NPD5406	Approved
0.729	Intermediate Similarity	NPD5408	Approved
0.729	Intermediate Similarity	NPD5405	Approved
0.729	Intermediate Similarity	NPD5404	Approved
0.7285	Intermediate Similarity	NPD3764	Approved
0.7267	Intermediate Similarity	NPD4908	Phase 1
0.7238	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4363	Phase 3
0.7222	Intermediate Similarity	NPD9545	Approved
0.7222	Intermediate Similarity	NPD4360	Phase 2
0.7219	Intermediate Similarity	NPD4625	Phase 3
0.7211	Intermediate Similarity	NPD1608	Approved
0.7207	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9493	Approved
0.7195	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5890	Approved
0.7195	Intermediate Similarity	NPD5889	Approved
0.719	Intermediate Similarity	NPD943	Approved
0.7188	Intermediate Similarity	NPD7390	Discontinued
0.7184	Intermediate Similarity	NPD6104	Discontinued
0.7181	Intermediate Similarity	NPD1164	Approved
0.7178	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4749	Approved
0.716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7134	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1019	Discontinued
0.7099	Intermediate Similarity	NPD5049	Phase 3
0.7099	Intermediate Similarity	NPD6273	Approved
0.7095	Intermediate Similarity	NPD3972	Approved
0.7088	Intermediate Similarity	NPD4361	Phase 2
0.7088	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8434	Phase 2
0.7076	Intermediate Similarity	NPD3926	Phase 2
0.7069	Intermediate Similarity	NPD1729	Discontinued
0.7044	Intermediate Similarity	NPD2654	Approved
0.7044	Intermediate Similarity	NPD1652	Phase 2
0.7041	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6004	Phase 3
0.7025	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6002	Phase 3
0.7018	Intermediate Similarity	NPD7229	Phase 3
0.7007	Intermediate Similarity	NPD17	Approved
0.7006	Intermediate Similarity	NPD8312	Approved
0.7006	Intermediate Similarity	NPD8313	Approved
0.6986	Remote Similarity	NPD1548	Phase 1
0.6984	Remote Similarity	NPD7584	Approved
0.6957	Remote Similarity	NPD2354	Approved
0.6954	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2403	Approved
0.6935	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1653	Approved
0.6906	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5761	Phase 2
0.6905	Remote Similarity	NPD5760	Phase 2
0.6903	Remote Similarity	NPD8032	Phase 2
0.6899	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1778	Approved
0.6883	Remote Similarity	NPD7095	Approved
0.6871	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2296	Approved
0.686	Remote Similarity	NPD7199	Phase 2
0.6859	Remote Similarity	NPD7585	Approved
0.6857	Remote Similarity	NPD7177	Discontinued
0.6857	Remote Similarity	NPD3751	Discontinued
0.6855	Remote Similarity	NPD4476	Approved
0.6855	Remote Similarity	NPD4477	Approved
0.6842	Remote Similarity	NPD1470	Approved
0.6839	Remote Similarity	NPD6798	Discontinued
0.6839	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7435	Discontinued
0.6818	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6355	Discontinued
0.6813	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1471	Phase 3
0.6813	Remote Similarity	NPD2353	Approved
0.6806	Remote Similarity	NPD7583	Approved

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