NPASS Compound

Structure

CID316560 OpenBabel06191716132D 36 38 0 0 1 0 0 0 0 0999 V2000 -6.2860 -4.5028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0927 -5.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -4.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7506 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3310 1.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3566 1.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3189 -2.8088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6559 -4.0660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9081 -3.1249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3449 -4.7550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9067 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0629 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0629 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 -2.4359 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8438 -4.3846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9067 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9067 -2.4359 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 11 1 0 0 0 0 8 13 2 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 14 19 1 0 0 0 0 14 29 2 0 0 0 0 15 20 1 0 0 0 0 15 30 2 0 0 0 0 16 21 1 0 0 0 0 16 24 2 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 18 25 2 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 20 26 2 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 33 2 0 0 0 0 24 36 1 0 0 0 0 25 28 1 0 0 0 0 25 34 1 0 0 0 0 26 28 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.21
Volume:	511.132
LogP:	4.8
LogD:	0.987
LogS:	-2.369
# Rotatable Bonds:	6
TPSA:	135.04
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	4.68
Fsp3:	0.464
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.662
MDCK Permeability:	2.1603264031000435e-05
Pgp-inhibitor:	0.862
Pgp-substrate:	0.855
Human Intestinal Absorption (HIA):	0.339
20% Bioavailability (F20%):	0.601
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	97.7193832397461%
Volume Distribution (VD):	1.133
Pgp-substrate:	1.8221828937530518%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.602
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.664
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.879

ADMET: Excretion

Clearance (CL):	12.664
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.089
Skin Sensitization:	0.051
Carcinogencity:	0.546
Eye Corrosion:	0.004
Eye Irritation:	0.223
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC316560

Natural Product ID:	NPC316560
*Common Name:**	Isodrummondin D
IUPAC Name:	n.a.
Synonyms:	Isodrummondin D
Standard InCHIKey:	QDEXSBYEIYRPIT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H32O8/c1-13(2)8-11-28(7)25(34)18(23(33)20(15(4)30)26(28)35)12-17-22(32)19(14(3)29)21(31)16-9-10-27(5,6)36-24(16)17/h8-10,31-32,34-35H,11-12H2,1-7H3
SMILES:	CC(=CCC1(C)C(=C(Cc2c(O)c(C(=O)C)c(c3c2OC(C)(C)C=C3)O)C(=O)C(=C1O)C(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483235
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO28558	Hypericum drummondii	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[1800634]
NPO28558	Hypericum drummondii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2746258]
NPO28558	Hypericum drummondii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28558	Hypericum drummondii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28558	Hypericum drummondii	Species	Hypericaceae	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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.78	ug.mL-1	PMID[540316]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.2	ug.mL-1	PMID[540316]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	1.56	ug.mL-1	PMID[540316]

☑ 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 NPC316560 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	1576
0.2-0.3	3936
0.3-0.4	9718
0.4-0.5	9401
0.5-0.6	4551
0.6-0.7	6602
0.7-0.8	4782
0.8-0.85	1141
0.85-0.9	536
0.9-0.95	59
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC316911
0.9926	High Similarity	NPC323884
0.9926	High Similarity	NPC321629
0.9926	High Similarity	NPC321148
0.9926	High Similarity	NPC326193
0.9778	High Similarity	NPC180501
0.9778	High Similarity	NPC54820
0.9778	High Similarity	NPC268178
0.9412	High Similarity	NPC101752
0.9357	High Similarity	NPC325346
0.9348	High Similarity	NPC272844
0.9348	High Similarity	NPC254168
0.9348	High Similarity	NPC248995
0.9281	High Similarity	NPC240305
0.9214	High Similarity	NPC221173
0.9214	High Similarity	NPC471587
0.9209	High Similarity	NPC477056
0.9209	High Similarity	NPC477055
0.9209	High Similarity	NPC470669
0.9209	High Similarity	NPC470668
0.9155	High Similarity	NPC11700
0.9149	High Similarity	NPC470555
0.9149	High Similarity	NPC205006
0.9149	High Similarity	NPC147688
0.9149	High Similarity	NPC64908
0.9149	High Similarity	NPC156590
0.9149	High Similarity	NPC118840
0.9143	High Similarity	NPC303633
0.9143	High Similarity	NPC96565
0.9143	High Similarity	NPC53181
0.9143	High Similarity	NPC216978
0.9143	High Similarity	NPC472343
0.9143	High Similarity	NPC23257
0.9143	High Similarity	NPC55018
0.9143	High Similarity	NPC220062
0.9143	High Similarity	NPC217186
0.9143	High Similarity	NPC270913
0.9143	High Similarity	NPC301217
0.9122	High Similarity	NPC470354
0.9091	High Similarity	NPC206212
0.9091	High Similarity	NPC278175
0.9091	High Similarity	NPC71184
0.9091	High Similarity	NPC257236
0.9085	High Similarity	NPC299080
0.9085	High Similarity	NPC78803
0.9085	High Similarity	NPC217083
0.9085	High Similarity	NPC214236
0.9085	High Similarity	NPC59739
0.9085	High Similarity	NPC62840
0.9085	High Similarity	NPC11561
0.9085	High Similarity	NPC293852
0.9085	High Similarity	NPC226636
0.9078	High Similarity	NPC235239
0.9078	High Similarity	NPC150522
0.9078	High Similarity	NPC261227
0.9078	High Similarity	NPC289660
0.9078	High Similarity	NPC164697
0.9078	High Similarity	NPC82920
0.9078	High Similarity	NPC159275
0.9078	High Similarity	NPC172986
0.9078	High Similarity	NPC305355
0.9078	High Similarity	NPC241100
0.9078	High Similarity	NPC475680
0.9078	High Similarity	NPC270883
0.9071	High Similarity	NPC201395
0.9071	High Similarity	NPC131130
0.9071	High Similarity	NPC470083
0.9071	High Similarity	NPC219584
0.9065	High Similarity	NPC174999
0.9048	High Similarity	NPC470353
0.9041	High Similarity	NPC188403
0.9028	High Similarity	NPC329678
0.9021	High Similarity	NPC473813
0.9021	High Similarity	NPC219915
0.9021	High Similarity	NPC38219
0.9021	High Similarity	NPC473812
0.9014	High Similarity	NPC111201
0.9014	High Similarity	NPC282300
0.9014	High Similarity	NPC103362
0.9014	High Similarity	NPC110969
0.9007	High Similarity	NPC78913
0.9007	High Similarity	NPC19476
0.9007	High Similarity	NPC18260
0.9007	High Similarity	NPC241975
0.9	High Similarity	NPC474624
0.9	High Similarity	NPC131782
0.9	High Similarity	NPC138047
0.8993	High Similarity	NPC151113
0.8993	High Similarity	NPC470352
0.8986	High Similarity	NPC108113
0.8986	High Similarity	NPC93756
0.8986	High Similarity	NPC16197
0.898	High Similarity	NPC81474
0.8966	High Similarity	NPC283234
0.8958	High Similarity	NPC469935
0.8958	High Similarity	NPC472447
0.8958	High Similarity	NPC469953
0.8958	High Similarity	NPC234629
0.8958	High Similarity	NPC178627
0.8958	High Similarity	NPC472446
0.8958	High Similarity	NPC311741
0.8951	High Similarity	NPC204469
0.8951	High Similarity	NPC144499
0.8951	High Similarity	NPC36181
0.8951	High Similarity	NPC200694
0.8944	High Similarity	NPC69769
0.8944	High Similarity	NPC477272
0.8936	High Similarity	NPC199458
0.8936	High Similarity	NPC474504
0.8936	High Similarity	NPC470672
0.8936	High Similarity	NPC470671
0.8936	High Similarity	NPC474487
0.8936	High Similarity	NPC183639
0.8929	High Similarity	NPC470982
0.8929	High Similarity	NPC470983
0.8929	High Similarity	NPC13408
0.8921	High Similarity	NPC125920
0.8913	High Similarity	NPC215875
0.8913	High Similarity	NPC15834
0.8913	High Similarity	NPC10971
0.8904	High Similarity	NPC160821
0.8904	High Similarity	NPC132592
0.8904	High Similarity	NPC469933
0.8897	High Similarity	NPC475052
0.8897	High Similarity	NPC285630
0.8897	High Similarity	NPC83357
0.8897	High Similarity	NPC111786
0.8897	High Similarity	NPC181388
0.8897	High Similarity	NPC246948
0.8897	High Similarity	NPC301276
0.8897	High Similarity	NPC176229
0.8897	High Similarity	NPC54577
0.8897	High Similarity	NPC470647
0.8897	High Similarity	NPC82534
0.8897	High Similarity	NPC124729
0.8897	High Similarity	NPC267375
0.8897	High Similarity	NPC220418
0.8897	High Similarity	NPC214774
0.8897	High Similarity	NPC195621
0.8897	High Similarity	NPC57470
0.8897	High Similarity	NPC127059
0.8897	High Similarity	NPC20488
0.8897	High Similarity	NPC67805
0.8897	High Similarity	NPC88964
0.8897	High Similarity	NPC312973
0.8897	High Similarity	NPC142405
0.8889	High Similarity	NPC316816
0.8889	High Similarity	NPC478086
0.8889	High Similarity	NPC185276
0.8889	High Similarity	NPC196459
0.8889	High Similarity	NPC188632
0.8889	High Similarity	NPC24821
0.8889	High Similarity	NPC190637
0.8889	High Similarity	NPC212932
0.8889	High Similarity	NPC87609
0.8889	High Similarity	NPC293053
0.8889	High Similarity	NPC214166
0.8889	High Similarity	NPC9117
0.8889	High Similarity	NPC166138
0.8889	High Similarity	NPC112791
0.8889	High Similarity	NPC18585
0.8889	High Similarity	NPC5990
0.8889	High Similarity	NPC94794
0.8889	High Similarity	NPC470296
0.8889	High Similarity	NPC106985
0.8881	High Similarity	NPC248372
0.8881	High Similarity	NPC14871
0.8881	High Similarity	NPC110038
0.8873	High Similarity	NPC139554
0.8873	High Similarity	NPC473076
0.8857	High Similarity	NPC60667
0.8857	High Similarity	NPC46869
0.8844	High Similarity	NPC469932
0.8836	High Similarity	NPC97716
0.8836	High Similarity	NPC14001
0.8836	High Similarity	NPC23728
0.8836	High Similarity	NPC110303
0.8836	High Similarity	NPC285748
0.8836	High Similarity	NPC104406
0.8836	High Similarity	NPC473077
0.8836	High Similarity	NPC24673
0.8836	High Similarity	NPC300988
0.8836	High Similarity	NPC237635
0.8836	High Similarity	NPC140120
0.8836	High Similarity	NPC180477
0.8836	High Similarity	NPC201731
0.8836	High Similarity	NPC296998
0.8836	High Similarity	NPC79469
0.8836	High Similarity	NPC166757
0.8836	High Similarity	NPC249942
0.8836	High Similarity	NPC10990
0.8836	High Similarity	NPC297886
0.8828	High Similarity	NPC131568
0.8828	High Similarity	NPC117716
0.8828	High Similarity	NPC131579
0.8828	High Similarity	NPC273538
0.8828	High Similarity	NPC235217
0.8828	High Similarity	NPC470673
0.8828	High Similarity	NPC1886
0.8828	High Similarity	NPC209040

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 NPC316560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	998
0.2-0.3	1765
0.3-0.4	2738
0.4-0.5	1919
0.5-0.6	980
0.6-0.7	284
0.7-0.8	102
0.8-0.85	16
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9124	High Similarity	NPD6651	Approved
0.9091	High Similarity	NPD7410	Clinical (unspecified phase)
0.9007	High Similarity	NPD2800	Approved
0.8828	High Similarity	NPD4378	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1549	Phase 2
0.8355	Intermediate Similarity	NPD7411	Suspended
0.8333	Intermediate Similarity	NPD1510	Phase 2
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.831	Intermediate Similarity	NPD1240	Approved
0.8289	Intermediate Similarity	NPD4380	Phase 2
0.8276	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD7819	Suspended
0.8247	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1607	Approved
0.8182	Intermediate Similarity	NPD6801	Discontinued
0.8133	Intermediate Similarity	NPD1511	Approved
0.8129	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD3750	Approved
0.8026	Intermediate Similarity	NPD1512	Approved
0.8013	Intermediate Similarity	NPD2801	Approved
0.7975	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2533	Approved
0.7961	Intermediate Similarity	NPD2532	Approved
0.7961	Intermediate Similarity	NPD2534	Approved
0.7949	Intermediate Similarity	NPD1934	Approved
0.7935	Intermediate Similarity	NPD6599	Discontinued
0.7933	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7768	Phase 2
0.7905	Intermediate Similarity	NPD6099	Approved
0.7905	Intermediate Similarity	NPD6100	Approved
0.7901	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6799	Approved
0.7867	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1243	Approved
0.7826	Intermediate Similarity	NPD6959	Discontinued
0.7793	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5124	Phase 1
0.7755	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3749	Approved
0.7736	Intermediate Similarity	NPD3817	Phase 2
0.7718	Intermediate Similarity	NPD3748	Approved
0.7688	Intermediate Similarity	NPD3882	Suspended
0.7683	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6166	Phase 2
0.7683	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD2313	Discontinued
0.7651	Intermediate Similarity	NPD7054	Approved
0.7636	Intermediate Similarity	NPD7473	Discontinued
0.7628	Intermediate Similarity	NPD5403	Approved
0.7628	Intermediate Similarity	NPD920	Approved
0.7616	Intermediate Similarity	NPD2344	Approved
0.7605	Intermediate Similarity	NPD7472	Approved
0.7605	Intermediate Similarity	NPD7074	Phase 3
0.76	Intermediate Similarity	NPD2799	Discontinued
0.7597	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3818	Discontinued
0.7582	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6232	Discontinued
0.756	Intermediate Similarity	NPD5953	Discontinued
0.755	Intermediate Similarity	NPD1551	Phase 2
0.755	Intermediate Similarity	NPD2935	Discontinued
0.7545	Intermediate Similarity	NPD7286	Phase 2
0.7535	Intermediate Similarity	NPD422	Phase 1
0.7515	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9717	Approved
0.7471	Intermediate Similarity	NPD7808	Phase 3
0.7456	Intermediate Similarity	NPD6797	Phase 2
0.7448	Intermediate Similarity	NPD1203	Approved
0.7439	Intermediate Similarity	NPD5494	Approved
0.7432	Intermediate Similarity	NPD3268	Approved
0.7421	Intermediate Similarity	NPD3226	Approved
0.7419	Intermediate Similarity	NPD2309	Approved
0.7415	Intermediate Similarity	NPD6832	Phase 2
0.7412	Intermediate Similarity	NPD6559	Discontinued
0.7368	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7033	Discontinued
0.7362	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4628	Phase 3
0.7349	Intermediate Similarity	NPD5710	Approved
0.7349	Intermediate Similarity	NPD5711	Approved
0.7329	Intermediate Similarity	NPD2797	Approved
0.7325	Intermediate Similarity	NPD7390	Discontinued
0.7315	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5402	Approved
0.729	Intermediate Similarity	NPD2654	Approved
0.7279	Intermediate Similarity	NPD2798	Approved
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD919	Approved
0.7267	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4308	Phase 3
0.7254	Intermediate Similarity	NPD1548	Phase 1
0.7241	Intermediate Similarity	NPD3972	Approved
0.7219	Intermediate Similarity	NPD943	Approved
0.7209	Intermediate Similarity	NPD6104	Discontinued
0.7203	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3926	Phase 2
0.72	Intermediate Similarity	NPD1296	Phase 2
0.7192	Intermediate Similarity	NPD4749	Approved
0.7186	Intermediate Similarity	NPD1247	Approved
0.7181	Intermediate Similarity	NPD4908	Phase 1
0.7172	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4360	Phase 2
0.7151	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD3225	Approved
0.7135	Intermediate Similarity	NPD5844	Phase 1
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7117	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4361	Phase 2
0.7099	Intermediate Similarity	NPD7458	Discontinued
0.7095	Intermediate Similarity	NPD3266	Approved
0.7095	Intermediate Similarity	NPD3267	Approved
0.7093	Intermediate Similarity	NPD1729	Discontinued
0.7091	Intermediate Similarity	NPD4288	Approved
0.7055	Intermediate Similarity	NPD1610	Phase 2
0.7055	Intermediate Similarity	NPD6585	Discontinued
0.703	Intermediate Similarity	NPD1465	Phase 2
0.7021	Intermediate Similarity	NPD1241	Discontinued
0.7014	Intermediate Similarity	NPD9545	Approved
0.7006	Intermediate Similarity	NPD8434	Phase 2
0.7005	Intermediate Similarity	NPD7584	Approved
0.6993	Remote Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD9493	Approved
0.6975	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD411	Approved
0.6959	Remote Similarity	NPD2403	Approved
0.6957	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD447	Suspended
0.6944	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5761	Phase 2
0.6928	Remote Similarity	NPD5760	Phase 2
0.6927	Remote Similarity	NPD4287	Approved
0.6918	Remote Similarity	NPD7003	Approved
0.6914	Remote Similarity	NPD5049	Phase 3
0.6913	Remote Similarity	NPD8651	Approved
0.6909	Remote Similarity	NPD5889	Approved
0.6909	Remote Similarity	NPD5890	Approved
0.6892	Remote Similarity	NPD1608	Approved
0.6886	Remote Similarity	NPD2296	Approved
0.6879	Remote Similarity	NPD5404	Approved
0.6879	Remote Similarity	NPD5406	Approved
0.6879	Remote Similarity	NPD5408	Approved
0.6879	Remote Similarity	NPD5405	Approved
0.6863	Remote Similarity	NPD3764	Approved
0.686	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7229	Phase 3
0.6839	Remote Similarity	NPD230	Phase 1
0.6839	Remote Similarity	NPD1933	Approved
0.6835	Remote Similarity	NPD1471	Phase 3
0.6824	Remote Similarity	NPD1201	Approved
0.6821	Remote Similarity	NPD1019	Discontinued
0.6821	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2424	Discontinued
0.6782	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2354	Approved
0.6765	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1470	Approved
0.6755	Remote Similarity	NPD1164	Approved
0.6753	Remote Similarity	NPD6798	Discontinued
0.675	Remote Similarity	NPD1652	Phase 2
0.6742	Remote Similarity	NPD8312	Approved
0.6742	Remote Similarity	NPD8313	Approved
0.674	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6002	Phase 3
0.673	Remote Similarity	NPD6005	Phase 3
0.673	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6004	Phase 3
0.6724	Remote Similarity	NPD3446	Phase 1
0.669	Remote Similarity	NPD6671	Approved
0.6689	Remote Similarity	NPD1778	Approved
0.6689	Remote Similarity	NPD6696	Suspended
0.6689	Remote Similarity	NPD17	Approved
0.6688	Remote Similarity	NPD7095	Approved
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7199	Phase 2
0.6686	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD1613	Approved
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD3142	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