NPASS Compound

Structure

NPC473978 OpenBabel07101718292D 34 37 0 0 1 0 0 0 0 0999 V2000 6.3210 3.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5708 -0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3893 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5889 3.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4550 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 -0.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5889 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9909 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1248 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4550 3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3120 0.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5889 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6390 0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4550 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1907 -1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9909 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8569 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 1.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7229 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7229 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 0.9659 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.4550 4.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0191 1.3449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3210 0.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4495 -2.4495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8569 3.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 2.1213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8569 0.4659 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 14 1 0 0 0 0 3 26 1 0 0 0 0 4 13 1 0 0 0 0 4 15 1 0 0 0 0 5 14 1 0 0 0 0 5 16 1 0 0 0 0 6 15 2 0 0 0 0 6 17 1 0 0 0 0 7 16 2 0 0 0 0 7 18 1 0 0 0 0 8 17 2 0 0 0 0 8 22 1 0 0 0 0 9 18 2 0 0 0 0 9 23 1 0 0 0 0 10 19 2 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 11 26 1 0 0 0 0 12 21 1 0 0 0 0 12 26 1 0 0 0 0 13 27 2 0 0 0 0 14 28 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 33 1 0 0 0 0 20 24 1 0 0 0 0 20 31 2 0 0 0 0 21 25 1 0 0 0 0 21 32 2 0 0 0 0 22 24 2 0 0 0 0 22 33 1 0 0 0 0 23 25 2 0 0 0 0 23 34 1 0 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.15
Volume:	465.347
LogP:	2.042
LogD:	2.037
LogS:	-4.137
# Rotatable Bonds:	6
TPSA:	131.11
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.567
Synthetic Accessibility Score:	3.869
Fsp3:	0.308
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:	-5.111
MDCK Permeability:	1.6211337424465455e-05
Pgp-inhibitor:	0.111
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.347
30% Bioavailability (F30%):	0.584

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	80.1875228881836%
Volume Distribution (VD):	0.75
Pgp-substrate:	10.346173286437988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.486
CYP1A2-substrate:	0.851
CYP2C19-inhibitor:	0.642
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.704
CYP2D6-substrate:	0.839
CYP3A4-inhibitor:	0.883
CYP3A4-substrate:	0.357

ADMET: Excretion

Clearance (CL):	10.671
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.479
Maximum Recommended Daily Dose:	0.807
Skin Sensitization:	0.547
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.047

Download Data

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

Natural Product: NPC473978

Natural Product ID:	NPC473978
*Common Name:**	Chrobisiamone A
IUPAC Name:	7-hydroxy-2-[[7-hydroxy-2-methyl-4-oxo-5-(2-oxopropyl)-3H-chromen-2-yl]methyl]-5-(2-oxopropyl)chromen-4-one
Synonyms:
Standard InCHIKey:	GEBKTFOJHPZDJE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H24O8/c1-13(27)4-15-6-17(29)8-22-24(15)20(31)10-19(33-22)11-26(3)12-21(32)25-16(5-14(2)28)7-18(30)9-23(25)34-26/h6-10,29-30H,4-5,11-12H2,1-3H3
SMILES:	CC(=O)CC1=C2C(=O)CC(OC2=CC(=C1)O)(C)CC3=CC(=O)C4=C(C=C(C=C4O3)O)CC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457048
PubChem CID:	44561380
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO31100	Cassia siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524594]
NPO31100	Cassia siamea	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[19754128]
NPO31100	Cassia siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.6	ug.mL-1	PMID[479928]

☑ 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 NPC473978 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	429
0.1-0.2	1770
0.2-0.3	4174
0.3-0.4	11176
0.4-0.5	7144
0.5-0.6	3968
0.6-0.7	5479
0.7-0.8	4755
0.8-0.85	2476
0.85-0.9	1202
0.9-0.95	119
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9441	High Similarity	NPC310340
0.9437	High Similarity	NPC275734
0.9329	High Similarity	NPC178964
0.9329	High Similarity	NPC95842
0.9329	High Similarity	NPC280530
0.932	High Similarity	NPC10027
0.932	High Similarity	NPC6923
0.932	High Similarity	NPC65775
0.9296	High Similarity	NPC57380
0.9257	High Similarity	NPC60413
0.9241	High Similarity	NPC219915
0.92	High Similarity	NPC329844
0.92	High Similarity	NPC214632
0.9189	High Similarity	NPC100985
0.9189	High Similarity	NPC97028
0.9189	High Similarity	NPC288036
0.9189	High Similarity	NPC65589
0.9189	High Similarity	NPC158338
0.9189	High Similarity	NPC97029
0.9184	High Similarity	NPC259632
0.9178	High Similarity	NPC312789
0.9145	High Similarity	NPC201127
0.9139	High Similarity	NPC55662
0.9139	High Similarity	NPC166054
0.9128	High Similarity	NPC227122
0.9128	High Similarity	NPC472633
0.9122	High Similarity	NPC256672
0.9122	High Similarity	NPC27221
0.9122	High Similarity	NPC35150
0.9122	High Similarity	NPC7025
0.9122	High Similarity	NPC106328
0.9116	High Similarity	NPC470676
0.9116	High Similarity	NPC196114
0.9116	High Similarity	NPC473135
0.9116	High Similarity	NPC473132
0.911	High Similarity	NPC38219
0.9085	High Similarity	NPC242712
0.9073	High Similarity	NPC210942
0.9073	High Similarity	NPC169990
0.9067	High Similarity	NPC149526
0.9067	High Similarity	NPC305965
0.9067	High Similarity	NPC478148
0.9067	High Similarity	NPC474417
0.9067	High Similarity	NPC72958
0.9067	High Similarity	NPC232645
0.906	High Similarity	NPC474052
0.9054	High Similarity	NPC12305
0.9054	High Similarity	NPC123202
0.9054	High Similarity	NPC296998
0.9054	High Similarity	NPC22005
0.9054	High Similarity	NPC7943
0.9054	High Similarity	NPC473077
0.9048	High Similarity	NPC117716
0.9048	High Similarity	NPC470674
0.9048	High Similarity	NPC134621
0.9048	High Similarity	NPC29577
0.9048	High Similarity	NPC32470
0.9048	High Similarity	NPC470673
0.9041	High Similarity	NPC144499
0.9041	High Similarity	NPC78803
0.9041	High Similarity	NPC62840
0.9041	High Similarity	NPC217083
0.9041	High Similarity	NPC214236
0.9041	High Similarity	NPC73028
0.9041	High Similarity	NPC293852
0.9041	High Similarity	NPC59739
0.9041	High Similarity	NPC299080
0.9026	High Similarity	NPC474960
0.9026	High Similarity	NPC471973
0.9021	High Similarity	NPC13408
0.9013	High Similarity	NPC99199
0.9013	High Similarity	NPC254351
0.9007	High Similarity	NPC142527
0.9007	High Similarity	NPC217447
0.9007	High Similarity	NPC474843
0.9007	High Similarity	NPC87708
0.9	High Similarity	NPC101957
0.9	High Similarity	NPC471115
0.9	High Similarity	NPC120105
0.9	High Similarity	NPC309979
0.9	High Similarity	NPC307780
0.9	High Similarity	NPC29777
0.8993	High Similarity	NPC296869
0.8993	High Similarity	NPC240253
0.8993	High Similarity	NPC471641
0.8993	High Similarity	NPC471642
0.8993	High Similarity	NPC240622
0.8986	High Similarity	NPC477955
0.8986	High Similarity	NPC83357
0.8986	High Similarity	NPC195621
0.8986	High Similarity	NPC267509
0.8986	High Similarity	NPC470647
0.8986	High Similarity	NPC67805
0.8986	High Similarity	NPC142405
0.8986	High Similarity	NPC20488
0.8986	High Similarity	NPC187282
0.8986	High Similarity	NPC111786
0.8986	High Similarity	NPC214774
0.8986	High Similarity	NPC290133
0.8986	High Similarity	NPC24136
0.8986	High Similarity	NPC237208
0.8986	High Similarity	NPC88964
0.8986	High Similarity	NPC312973
0.8986	High Similarity	NPC176229
0.8986	High Similarity	NPC301276
0.8986	High Similarity	NPC475052
0.8986	High Similarity	NPC246948
0.8986	High Similarity	NPC267375
0.8986	High Similarity	NPC54577
0.898	High Similarity	NPC95123
0.898	High Similarity	NPC11700
0.898	High Similarity	NPC66404
0.898	High Similarity	NPC18585
0.898	High Similarity	NPC166138
0.898	High Similarity	NPC106985
0.8973	High Similarity	NPC64908
0.8973	High Similarity	NPC49108
0.8973	High Similarity	NPC156590
0.8973	High Similarity	NPC105648
0.8973	High Similarity	NPC118840
0.8973	High Similarity	NPC147688
0.8973	High Similarity	NPC205006
0.8966	High Similarity	NPC216978
0.8966	High Similarity	NPC55018
0.8966	High Similarity	NPC301217
0.8966	High Similarity	NPC303633
0.8966	High Similarity	NPC96565
0.8966	High Similarity	NPC140890
0.8966	High Similarity	NPC220062
0.8961	High Similarity	NPC55443
0.8961	High Similarity	NPC18699
0.8961	High Similarity	NPC177650
0.8958	High Similarity	NPC228661
0.8954	High Similarity	NPC472907
0.8954	High Similarity	NPC24640
0.8947	High Similarity	NPC472905
0.8947	High Similarity	NPC89474
0.894	High Similarity	NPC258249
0.894	High Similarity	NPC133856
0.8933	High Similarity	NPC473016
0.8926	High Similarity	NPC79469
0.8926	High Similarity	NPC23728
0.8926	High Similarity	NPC283234
0.8926	High Similarity	NPC14001
0.8926	High Similarity	NPC24673
0.8926	High Similarity	NPC34802
0.8926	High Similarity	NPC201731
0.8926	High Similarity	NPC140120
0.8926	High Similarity	NPC97716
0.8926	High Similarity	NPC237635
0.8926	High Similarity	NPC166757
0.8926	High Similarity	NPC110303
0.8926	High Similarity	NPC104406
0.8919	High Similarity	NPC278175
0.8919	High Similarity	NPC257236
0.8919	High Similarity	NPC311144
0.8919	High Similarity	NPC234629
0.8919	High Similarity	NPC271288
0.8919	High Similarity	NPC311741
0.8912	High Similarity	NPC11561
0.8912	High Similarity	NPC202981
0.8912	High Similarity	NPC226636
0.8912	High Similarity	NPC1534
0.891	High Similarity	NPC329760
0.891	High Similarity	NPC229632
0.8904	High Similarity	NPC477272
0.8904	High Similarity	NPC475680
0.8904	High Similarity	NPC76445
0.8904	High Similarity	NPC150522
0.8904	High Similarity	NPC69769
0.8904	High Similarity	NPC241100
0.8904	High Similarity	NPC235239
0.8904	High Similarity	NPC188243
0.8904	High Similarity	NPC220106
0.8904	High Similarity	NPC6407
0.8904	High Similarity	NPC261227
0.8904	High Similarity	NPC270883
0.8904	High Similarity	NPC110228
0.8904	High Similarity	NPC182421
0.8904	High Similarity	NPC172986
0.8904	High Similarity	NPC129853
0.8904	High Similarity	NPC159275
0.8904	High Similarity	NPC305355
0.8904	High Similarity	NPC284550
0.8903	High Similarity	NPC312993
0.8903	High Similarity	NPC186325
0.8903	High Similarity	NPC139036
0.8903	High Similarity	NPC200746
0.8897	High Similarity	NPC201395
0.8897	High Similarity	NPC470671
0.8897	High Similarity	NPC470672
0.8897	High Similarity	NPC474487
0.8897	High Similarity	NPC474504
0.8897	High Similarity	NPC131130
0.8896	High Similarity	NPC472963
0.8896	High Similarity	NPC263483
0.8896	High Similarity	NPC268360
0.8896	High Similarity	NPC136674
0.8896	High Similarity	NPC272196
0.8889	High Similarity	NPC67396

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 NPC473978 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	992
0.2-0.3	1579
0.3-0.4	2712
0.4-0.5	1881
0.5-0.6	1052
0.6-0.7	369
0.7-0.8	125
0.8-0.85	41
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD7410	Clinical (unspecified phase)
0.8889	High Similarity	NPD8443	Clinical (unspecified phase)
0.8824	High Similarity	NPD7819	Suspended
0.8792	High Similarity	NPD4378	Clinical (unspecified phase)
0.8726	High Similarity	NPD6959	Discontinued
0.8699	High Similarity	NPD1552	Clinical (unspecified phase)
0.8699	High Similarity	NPD1550	Clinical (unspecified phase)
0.8693	High Similarity	NPD7411	Suspended
0.8649	High Similarity	NPD3750	Approved
0.8639	High Similarity	NPD970	Clinical (unspecified phase)
0.8639	High Similarity	NPD1549	Phase 2
0.86	High Similarity	NPD1511	Approved
0.8581	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD1510	Phase 2
0.8535	High Similarity	NPD3749	Approved
0.8516	High Similarity	NPD1934	Approved
0.8506	High Similarity	NPD4380	Phase 2
0.8503	High Similarity	NPD2796	Approved
0.8487	Intermediate Similarity	NPD1512	Approved
0.8462	Intermediate Similarity	NPD2801	Approved
0.8447	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1240	Approved
0.8378	Intermediate Similarity	NPD6099	Approved
0.8378	Intermediate Similarity	NPD6100	Approved
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD3748	Approved
0.8302	Intermediate Similarity	NPD7075	Discontinued
0.8299	Intermediate Similarity	NPD1607	Approved
0.8205	Intermediate Similarity	NPD3226	Approved
0.8182	Intermediate Similarity	NPD7054	Approved
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD7472	Approved
0.8125	Intermediate Similarity	NPD3882	Suspended
0.8125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD7390	Discontinued
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.8113	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8092	Intermediate Similarity	NPD2800	Approved
0.8084	Intermediate Similarity	NPD6797	Phase 2
0.8072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2532	Approved
0.8065	Intermediate Similarity	NPD2534	Approved
0.8065	Intermediate Similarity	NPD2533	Approved
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.805	Intermediate Similarity	NPD6801	Discontinued
0.8036	Intermediate Similarity	NPD7251	Discontinued
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD6799	Approved
0.7988	Intermediate Similarity	NPD7808	Phase 3
0.7975	Intermediate Similarity	NPD5494	Approved
0.7974	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6599	Discontinued
0.7922	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD3268	Approved
0.7882	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1243	Approved
0.7857	Intermediate Similarity	NPD5844	Phase 1
0.7848	Intermediate Similarity	NPD5403	Approved
0.7843	Intermediate Similarity	NPD2344	Approved
0.7843	Intermediate Similarity	NPD2346	Discontinued
0.784	Intermediate Similarity	NPD5402	Approved
0.7838	Intermediate Similarity	NPD4625	Phase 3
0.7815	Intermediate Similarity	NPD6651	Approved
0.7785	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1551	Phase 2
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.777	Intermediate Similarity	NPD4908	Phase 1
0.7722	Intermediate Similarity	NPD5401	Approved
0.7719	Intermediate Similarity	NPD6559	Discontinued
0.7712	Intermediate Similarity	NPD2799	Discontinued
0.7682	Intermediate Similarity	NPD943	Approved
0.7674	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4749	Approved
0.7667	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2309	Approved
0.7635	Intermediate Similarity	NPD2798	Approved
0.7624	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4288	Approved
0.7619	Intermediate Similarity	NPD3926	Phase 2
0.758	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3266	Approved
0.7568	Intermediate Similarity	NPD3267	Approved
0.7568	Intermediate Similarity	NPD2797	Approved
0.7568	Intermediate Similarity	NPD1203	Approved
0.756	Intermediate Similarity	NPD5711	Approved
0.756	Intermediate Similarity	NPD5710	Approved
0.7558	Intermediate Similarity	NPD5953	Discontinued
0.755	Intermediate Similarity	NPD2313	Discontinued
0.7534	Intermediate Similarity	NPD1610	Phase 2
0.7534	Intermediate Similarity	NPD1201	Approved
0.7528	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD920	Approved
0.7514	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3225	Approved
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7484	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4308	Phase 3
0.7483	Intermediate Similarity	NPD1608	Approved
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7467	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3787	Discontinued
0.745	Intermediate Similarity	NPD1470	Approved
0.7444	Intermediate Similarity	NPD4360	Phase 2
0.7444	Intermediate Similarity	NPD4363	Phase 3
0.7436	Intermediate Similarity	NPD5406	Approved
0.7436	Intermediate Similarity	NPD5405	Approved
0.7436	Intermediate Similarity	NPD5408	Approved
0.7436	Intermediate Similarity	NPD5404	Approved
0.7434	Intermediate Similarity	NPD3764	Approved
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7415	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD919	Approved
0.7379	Intermediate Similarity	NPD1548	Phase 1
0.7372	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD9717	Approved
0.7341	Intermediate Similarity	NPD7286	Phase 2
0.733	Intermediate Similarity	NPD8313	Approved
0.733	Intermediate Similarity	NPD8312	Approved
0.732	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2654	Approved
0.729	Intermediate Similarity	NPD5124	Phase 1
0.729	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD6585	Discontinued
0.7267	Intermediate Similarity	NPD2403	Approved
0.7251	Intermediate Similarity	NPD7229	Phase 3
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD4307	Phase 2
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4361	Phase 2
0.7213	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD411	Approved
0.7186	Intermediate Similarity	NPD6844	Discontinued
0.7186	Intermediate Similarity	NPD37	Approved
0.7179	Intermediate Similarity	NPD447	Suspended
0.7179	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD230	Phase 1
0.7176	Intermediate Similarity	NPD6234	Discontinued
0.7174	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD7003	Approved
0.7134	Intermediate Similarity	NPD6273	Approved
0.7133	Intermediate Similarity	NPD3972	Approved
0.7128	Intermediate Similarity	NPD7696	Phase 3
0.7128	Intermediate Similarity	NPD7697	Approved
0.7128	Intermediate Similarity	NPD7698	Approved
0.7128	Intermediate Similarity	NPD7435	Discontinued
0.7127	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5889	Approved
0.7126	Intermediate Similarity	NPD5890	Approved
0.7124	Intermediate Similarity	NPD2861	Phase 2
0.712	Intermediate Similarity	NPD8151	Discontinued
0.7119	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7111	Intermediate Similarity	NPD8150	Discontinued
0.7105	Intermediate Similarity	NPD7584	Approved
0.7101	Intermediate Similarity	NPD2296	Approved
0.7097	Intermediate Similarity	NPD1296	Phase 2
0.709	Intermediate Similarity	NPD7870	Phase 2
0.709	Intermediate Similarity	NPD7871	Phase 2
0.7086	Intermediate Similarity	NPD7228	Approved
0.7086	Intermediate Similarity	NPD7177	Discontinued
0.7086	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1933	Approved
0.7056	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7783	Phase 2
0.7047	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1876	Approved
0.7024	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD405	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