NPASS Compound

Structure

NPC259710 OpenBabel07101719522D 32 35 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 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 1.8660 -0.5000 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 -7.7942 2.5000 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 -1.7321 0.0000 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 -2.0000 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 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 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 -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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 11 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 26 1 0 0 0 0 16 30 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 28 2 0 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 15 1 1 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	453.039
LogP:	6.068
LogD:	4.191
LogS:	-2.578
# Rotatable Bonds:	4
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	3.818
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.728
MDCK Permeability:	1.5823296052985825e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	96.94657135009766%
Volume Distribution (VD):	0.64
Pgp-substrate:	5.500120162963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.58
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.915
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.895
CYP2D6-substrate:	0.544
CYP3A4-inhibitor:	0.761
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	1.501
Half-life (T1/2):	0.035

ADMET: Toxicity

hERG Blockers:	0.261
Human Hepatotoxicity (H-HT):	0.877
Drug-inuced Liver Injury (DILI):	0.765
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.677
Skin Sensitization:	0.454
Carcinogencity:	0.25
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.32

Download Data

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

Natural Product: NPC259710

Natural Product ID:	NPC259710
*Common Name:**	Khonklonginol B
IUPAC Name:	(7S,8R)-5,7-dihydroxy-8-(4-methoxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one
Synonyms:	khonklonginol B
Standard InCHIKey:	ACXXSEDDPWHZAU-DHIUTWEWSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-14(2)6-11-18-24-17(12-13-26(3,4)32-24)20(27)19-21(28)22(29)23(31-25(18)19)15-7-9-16(30-5)10-8-15/h6-10,12-13,22-23,27,29H,11H2,1-5H3/t22-,23-/m1/s1
SMILES:	CC(=CCc1c2c(C=CC(C)(C)O2)c(c2C(=O)[C@H]([C@@H](c3ccc(cc3)OC)Oc12)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551513
PubChem CID:	44179864
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

*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
NPO12525	Eriosema chinense	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[19555123]
NPO12525	Eriosema chinense	Species	Fabaceae	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	3
MIC	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.8	ug.mL-1	PMID[514916]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	4.3	ug.mL-1	PMID[514916]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	6.9	ug.mL-1	PMID[514916]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	50.0	ug.mL-1	PMID[514916]

☑ 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 NPC259710 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	381
0.1-0.2	1498
0.2-0.3	3655
0.3-0.4	8986
0.4-0.5	9457
0.5-0.6	3711
0.6-0.7	5415
0.7-0.8	5233
0.8-0.85	2721
0.85-0.9	1170
0.9-0.95	405
0.95-1	65

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC217706
1.0	High Similarity	NPC48579
1.0	High Similarity	NPC304207
1.0	High Similarity	NPC207809
0.9932	High Similarity	NPC248793
0.9932	High Similarity	NPC180301
0.9865	High Similarity	NPC304745
0.9865	High Similarity	NPC111341
0.9797	High Similarity	NPC7989
0.9797	High Similarity	NPC472583
0.9797	High Similarity	NPC236756
0.9797	High Similarity	NPC223701
0.9797	High Similarity	NPC311579
0.9797	High Similarity	NPC268193
0.9796	High Similarity	NPC262039
0.9796	High Similarity	NPC278476
0.9796	High Similarity	NPC254412
0.9796	High Similarity	NPC319910
0.9796	High Similarity	NPC262038
0.9732	High Similarity	NPC476169
0.973	High Similarity	NPC216035
0.973	High Similarity	NPC475790
0.973	High Similarity	NPC56232
0.973	High Similarity	NPC150123
0.973	High Similarity	NPC244583
0.973	High Similarity	NPC138288
0.973	High Similarity	NPC171651
0.973	High Similarity	NPC243171
0.973	High Similarity	NPC217149
0.973	High Similarity	NPC161881
0.973	High Similarity	NPC10807
0.973	High Similarity	NPC35567
0.9728	High Similarity	NPC105136
0.9667	High Similarity	NPC215917
0.9667	High Similarity	NPC10754
0.9667	High Similarity	NPC20530
0.9664	High Similarity	NPC88983
0.9664	High Similarity	NPC244250
0.9664	High Similarity	NPC20907
0.9664	High Similarity	NPC469405
0.9664	High Similarity	NPC293286
0.9662	High Similarity	NPC209846
0.9662	High Similarity	NPC471676
0.9662	High Similarity	NPC244577
0.9662	High Similarity	NPC289774
0.9662	High Similarity	NPC474023
0.9662	High Similarity	NPC472420
0.9662	High Similarity	NPC474021
0.9662	High Similarity	NPC328740
0.9662	High Similarity	NPC477897
0.9662	High Similarity	NPC472422
0.9662	High Similarity	NPC263384
0.9662	High Similarity	NPC471677
0.96	High Similarity	NPC477958
0.96	High Similarity	NPC470681
0.9597	High Similarity	NPC210597
0.9595	High Similarity	NPC61258
0.9592	High Similarity	NPC296869
0.9545	High Similarity	NPC183672
0.9545	High Similarity	NPC472625
0.9533	High Similarity	NPC100134
0.9533	High Similarity	NPC326592
0.9533	High Similarity	NPC109594
0.9533	High Similarity	NPC209760
0.9533	High Similarity	NPC112701
0.953	High Similarity	NPC472636
0.953	High Similarity	NPC471675
0.9527	High Similarity	NPC5173
0.9527	High Similarity	NPC472628
0.9524	High Similarity	NPC211466
0.9524	High Similarity	NPC176869
0.9524	High Similarity	NPC476182
0.9524	High Similarity	NPC473077
0.9524	High Similarity	NPC40086
0.9524	High Similarity	NPC296998
0.9524	High Similarity	NPC44721
0.9524	High Similarity	NPC472627
0.9524	High Similarity	NPC85773
0.9524	High Similarity	NPC122828
0.9524	High Similarity	NPC472918
0.9524	High Similarity	NPC3779
0.9481	High Similarity	NPC131745
0.9477	High Similarity	NPC475784
0.9474	High Similarity	NPC282390
0.9474	High Similarity	NPC281137
0.947	High Similarity	NPC477530
0.947	High Similarity	NPC471116
0.9467	High Similarity	NPC476238
0.9467	High Similarity	NPC327269
0.9467	High Similarity	NPC285623
0.9467	High Similarity	NPC31627
0.9467	High Similarity	NPC473996
0.9463	High Similarity	NPC472633
0.9463	High Similarity	NPC124478
0.9463	High Similarity	NPC177308
0.9459	High Similarity	NPC244407
0.9459	High Similarity	NPC10097
0.9456	High Similarity	NPC214774
0.9456	High Similarity	NPC67805
0.9456	High Similarity	NPC88964
0.9456	High Similarity	NPC312973
0.9456	High Similarity	NPC470647
0.9456	High Similarity	NPC111786
0.9456	High Similarity	NPC301276
0.9456	High Similarity	NPC474302
0.9456	High Similarity	NPC54577
0.9456	High Similarity	NPC195621
0.9456	High Similarity	NPC472629
0.9456	High Similarity	NPC475052
0.9456	High Similarity	NPC20488
0.9456	High Similarity	NPC83357
0.9456	High Similarity	NPC246948
0.9456	High Similarity	NPC142405
0.9456	High Similarity	NPC124729
0.9456	High Similarity	NPC267375
0.9456	High Similarity	NPC176229
0.9419	High Similarity	NPC66087
0.9419	High Similarity	NPC278419
0.9419	High Similarity	NPC179198
0.9416	High Similarity	NPC474038
0.9416	High Similarity	NPC289771
0.9412	High Similarity	NPC22192
0.9412	High Similarity	NPC123544
0.9408	High Similarity	NPC78492
0.9408	High Similarity	NPC146636
0.9408	High Similarity	NPC208152
0.9404	High Similarity	NPC203080
0.94	High Similarity	NPC472580
0.94	High Similarity	NPC474772
0.94	High Similarity	NPC472423
0.94	High Similarity	NPC471229
0.94	High Similarity	NPC474744
0.9396	High Similarity	NPC470461
0.9396	High Similarity	NPC139966
0.9396	High Similarity	NPC89442
0.9396	High Similarity	NPC307052
0.9396	High Similarity	NPC277032
0.9392	High Similarity	NPC470670
0.9392	High Similarity	NPC473133
0.9392	High Similarity	NPC110303
0.9392	High Similarity	NPC47388
0.9392	High Similarity	NPC166757
0.9392	High Similarity	NPC23728
0.9392	High Similarity	NPC91902
0.9392	High Similarity	NPC222298
0.9392	High Similarity	NPC51070
0.9392	High Similarity	NPC283234
0.9392	High Similarity	NPC14001
0.9388	High Similarity	NPC124780
0.9388	High Similarity	NPC208176
0.9388	High Similarity	NPC62290
0.9388	High Similarity	NPC273538
0.9388	High Similarity	NPC49130
0.9388	High Similarity	NPC216538
0.9388	High Similarity	NPC224714
0.9388	High Similarity	NPC326506
0.9388	High Similarity	NPC470890
0.9388	High Similarity	NPC87486
0.9388	High Similarity	NPC4152
0.9388	High Similarity	NPC142731
0.9388	High Similarity	NPC279417
0.9388	High Similarity	NPC306607
0.9355	High Similarity	NPC259834
0.9351	High Similarity	NPC471976
0.9351	High Similarity	NPC119209
0.9351	High Similarity	NPC287328
0.9351	High Similarity	NPC118256
0.9351	High Similarity	NPC192686
0.9351	High Similarity	NPC282009
0.9346	High Similarity	NPC210048
0.9346	High Similarity	NPC284820
0.9346	High Similarity	NPC473272
0.9338	High Similarity	NPC256141
0.9338	High Similarity	NPC477957
0.9333	High Similarity	NPC267117
0.9333	High Similarity	NPC471115
0.9333	High Similarity	NPC472421
0.9333	High Similarity	NPC29777
0.9329	High Similarity	NPC218569
0.9329	High Similarity	NPC6511
0.9329	High Similarity	NPC161191
0.9329	High Similarity	NPC132592
0.9329	High Similarity	NPC160821
0.9329	High Similarity	NPC470460
0.9324	High Similarity	NPC316769
0.9324	High Similarity	NPC148011
0.9324	High Similarity	NPC5820
0.9324	High Similarity	NPC229190
0.9324	High Similarity	NPC470458
0.9324	High Similarity	NPC1940
0.9324	High Similarity	NPC178343
0.9324	High Similarity	NPC220418
0.9324	High Similarity	NPC306488
0.932	High Similarity	NPC214166
0.932	High Similarity	NPC478086
0.932	High Similarity	NPC190637
0.932	High Similarity	NPC212932
0.932	High Similarity	NPC293053
0.932	High Similarity	NPC9117
0.932	High Similarity	NPC219915

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 NPC259710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	878
0.2-0.3	1675
0.3-0.4	2631
0.4-0.5	1878
0.5-0.6	1098
0.6-0.7	456
0.7-0.8	146
0.8-0.85	35
0.85-0.9	17
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9463	High Similarity	NPD4380	Phase 2
0.9388	High Similarity	NPD4378	Clinical (unspecified phase)
0.9221	High Similarity	NPD7075	Discontinued
0.9182	High Similarity	NPD7804	Clinical (unspecified phase)
0.915	High Similarity	NPD7096	Clinical (unspecified phase)
0.915	High Similarity	NPD2393	Clinical (unspecified phase)
0.9097	High Similarity	NPD4381	Clinical (unspecified phase)
0.9085	High Similarity	NPD6801	Discontinued
0.8994	High Similarity	NPD6168	Clinical (unspecified phase)
0.8994	High Similarity	NPD6167	Clinical (unspecified phase)
0.8994	High Similarity	NPD6166	Phase 2
0.8961	High Similarity	NPD1934	Approved
0.8912	High Similarity	NPD1552	Clinical (unspecified phase)
0.8912	High Similarity	NPD1550	Clinical (unspecified phase)
0.8874	High Similarity	NPD7410	Clinical (unspecified phase)
0.8851	High Similarity	NPD1549	Phase 2
0.8846	High Similarity	NPD8443	Clinical (unspecified phase)
0.872	High Similarity	NPD6797	Phase 2
0.8716	High Similarity	NPD2796	Approved
0.8693	High Similarity	NPD1512	Approved
0.8684	High Similarity	NPD6799	Approved
0.8667	High Similarity	NPD7251	Discontinued
0.8662	High Similarity	NPD2801	Approved
0.8654	High Similarity	NPD7411	Suspended
0.8649	High Similarity	NPD1510	Phase 2
0.8636	High Similarity	NPD5403	Approved
0.8614	High Similarity	NPD7808	Phase 3
0.8608	High Similarity	NPD3817	Phase 2
0.8598	High Similarity	NPD7054	Approved
0.8562	High Similarity	NPD1511	Approved
0.8553	High Similarity	NPD3882	Suspended
0.8545	High Similarity	NPD7074	Phase 3
0.8545	High Similarity	NPD7472	Approved
0.8506	High Similarity	NPD5401	Approved
0.8503	High Similarity	NPD4338	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD5402	Approved
0.8471	Intermediate Similarity	NPD6599	Discontinued
0.8457	Intermediate Similarity	NPD6959	Discontinued
0.8428	Intermediate Similarity	NPD7819	Suspended
0.8424	Intermediate Similarity	NPD3818	Discontinued
0.8395	Intermediate Similarity	NPD5494	Approved
0.8378	Intermediate Similarity	NPD1240	Approved
0.8333	Intermediate Similarity	NPD6559	Discontinued
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1607	Approved
0.821	Intermediate Similarity	NPD7768	Phase 2
0.8166	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.8129	Intermediate Similarity	NPD3750	Approved
0.8065	Intermediate Similarity	NPD2800	Approved
0.8065	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3749	Approved
0.8034	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6232	Discontinued
0.7937	Intermediate Similarity	NPD920	Approved
0.7929	Intermediate Similarity	NPD7473	Discontinued
0.7921	Intermediate Similarity	NPD4360	Phase 2
0.7921	Intermediate Similarity	NPD4363	Phase 3
0.7904	Intermediate Similarity	NPD1247	Approved
0.7892	Intermediate Similarity	NPD919	Approved
0.7885	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3751	Discontinued
0.7881	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2935	Discontinued
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7857	Intermediate Similarity	NPD3787	Discontinued
0.7843	Intermediate Similarity	NPD5124	Phase 1
0.7843	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7584	Approved
0.7834	Intermediate Similarity	NPD1243	Approved
0.7812	Intermediate Similarity	NPD2533	Approved
0.7812	Intermediate Similarity	NPD2532	Approved
0.7812	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2534	Approved
0.7806	Intermediate Similarity	NPD7033	Discontinued
0.7806	Intermediate Similarity	NPD3748	Approved
0.7799	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6651	Approved
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7748	Intermediate Similarity	NPD4908	Phase 1
0.7746	Intermediate Similarity	NPD5953	Discontinued
0.7733	Intermediate Similarity	NPD7286	Phase 2
0.7705	Intermediate Similarity	NPD6782	Approved
0.7705	Intermediate Similarity	NPD6778	Approved
0.7705	Intermediate Similarity	NPD6781	Approved
0.7705	Intermediate Similarity	NPD6777	Approved
0.7705	Intermediate Similarity	NPD6776	Approved
0.7705	Intermediate Similarity	NPD6779	Approved
0.7705	Intermediate Similarity	NPD6780	Approved
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7658	Intermediate Similarity	NPD2424	Discontinued
0.7651	Intermediate Similarity	NPD1465	Phase 2
0.7647	Intermediate Similarity	NPD6798	Discontinued
0.7643	Intermediate Similarity	NPD6100	Approved
0.7643	Intermediate Similarity	NPD6099	Approved
0.7635	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8312	Approved
0.7614	Intermediate Similarity	NPD8313	Approved
0.7602	Intermediate Similarity	NPD3926	Phase 2
0.7595	Intermediate Similarity	NPD2344	Approved
0.7584	Intermediate Similarity	NPD8150	Discontinued
0.7584	Intermediate Similarity	NPD8434	Phase 2
0.7581	Intermediate Similarity	NPD7435	Discontinued
0.7548	Intermediate Similarity	NPD943	Approved
0.7545	Intermediate Similarity	NPD8455	Phase 2
0.7531	Intermediate Similarity	NPD7390	Discontinued
0.753	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7698	Approved
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7486	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4361	Phase 2
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6233	Phase 2
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7457	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7870	Phase 2
0.7447	Intermediate Similarity	NPD7871	Phase 2
0.7443	Intermediate Similarity	NPD3823	Discontinued
0.7434	Intermediate Similarity	NPD1203	Approved
0.7432	Intermediate Similarity	NPD6534	Approved
0.7432	Intermediate Similarity	NPD6535	Approved
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7701	Phase 2
0.7421	Intermediate Similarity	NPD7585	Approved
0.7419	Intermediate Similarity	NPD3268	Approved
0.741	Intermediate Similarity	NPD7458	Discontinued
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6190	Approved
0.7407	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.7386	Intermediate Similarity	NPD2798	Approved
0.7381	Intermediate Similarity	NPD6844	Discontinued
0.7368	Intermediate Similarity	NPD7583	Approved
0.7358	Intermediate Similarity	NPD4308	Phase 3
0.7356	Intermediate Similarity	NPD2403	Approved
0.7355	Intermediate Similarity	NPD4625	Phase 3
0.7344	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7874	Approved
0.7341	Intermediate Similarity	NPD5710	Approved
0.7341	Intermediate Similarity	NPD5711	Approved
0.7333	Intermediate Similarity	NPD5049	Phase 3
0.7326	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4060	Phase 1
0.732	Intermediate Similarity	NPD2797	Approved
0.7312	Intermediate Similarity	NPD7699	Phase 2
0.7312	Intermediate Similarity	NPD7700	Phase 2
0.7308	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7801	Approved
0.7306	Intermediate Similarity	NPD7783	Phase 2
0.7301	Intermediate Similarity	NPD2354	Approved
0.7301	Intermediate Similarity	NPD3887	Approved
0.7299	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.7289	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7283	Intermediate Similarity	NPD7199	Phase 2
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD4662	Approved
0.7273	Intermediate Similarity	NPD4661	Approved
0.7255	Intermediate Similarity	NPD3225	Approved
0.725	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6823	Phase 2
0.7246	Intermediate Similarity	NPD1653	Approved
0.7237	Intermediate Similarity	NPD9717	Approved
0.7219	Intermediate Similarity	NPD5889	Approved
0.7219	Intermediate Similarity	NPD5890	Approved
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4288	Approved
0.7191	Intermediate Similarity	NPD1729	Discontinued
0.7188	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4538	Approved
0.7188	Intermediate Similarity	NPD4536	Approved
0.7178	Intermediate Similarity	NPD2654	Approved
0.7178	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD37	Approved
0.7175	Intermediate Similarity	NPD7228	Approved
0.7173	Intermediate Similarity	NPD8319	Approved
0.7173	Intermediate Similarity	NPD8320	Phase 1

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