NPASS Compound

Structure

NPC221173 OpenBabel07101719242D 26 28 0 0 0 0 0 0 0 0999 V2000 -2.5981 4.5000 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 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 -3.4641 3.0000 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 -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 -4.3301 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 -1.7321 -0.0000 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 -4.3301 0.5000 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 -0.8660 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 -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 -0.0000 -1.0000 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 5 1 0 0 0 0 2 6 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	371.599
LogP:	5.545
LogD:	4.531
LogS:	-3.78
# Rotatable Bonds:	5
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	3.104
Fsp3:	0.429
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:	-4.756
MDCK Permeability:	1.8496471966500394e-05
Pgp-inhibitor:	0.939
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	99.26457214355469%
Volume Distribution (VD):	0.659
Pgp-substrate:	1.7332028150558472%

ADMET: Metabolism

CYP1A2-inhibitor:	0.806
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.884
CYP2C19-substrate:	0.236
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.841
CYP2D6-inhibitor:	0.776
CYP2D6-substrate:	0.316
CYP3A4-inhibitor:	0.479
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	3.205
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.673
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.315
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.532
Skin Sensitization:	0.381
Carcinogencity:	0.904
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.377

Download Data

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

Natural Product: NPC221173

Natural Product ID:	NPC221173
*Common Name:**	Mammea B/Ac Cyclo D
IUPAC Name:	6-butanoyl-5-hydroxy-8,8-dimethyl-4-propylpyrano[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	SMRSMFDNXPPPCA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-5-7-12-11-15(23)25-19-13-9-10-21(3,4)26-20(13)17(14(22)8-6-2)18(24)16(12)19/h9-11,24H,5-8H2,1-4H3
SMILES:	CCCC(=O)c1c2OC(C)(C)C=Cc2c2c(c1O)c(CCC)cc(=O)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2064612
PubChem CID:	70684457
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular 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
NPO32974	mammea siamensis	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22831798]
NPO32974	mammea siamensis	Species	Calophyllaceae	Eukaryota	flower	n.a.	n.a.	PMID[23206866]

☑ 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	10
Others	2

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	9.9	%	PMID[455781]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	13.8	%	PMID[455781]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	30000.0	nM	PMID[455781]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[455782]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	50000.0	nM	PMID[455782]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	50000.0	nM	PMID[455782]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	50000.0	nM	PMID[455782]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	47560.0	nM	PMID[455782]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	37190.0	nM	PMID[455782]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[455782]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[455782]

☑ 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 NPC221173 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	375
0.1-0.2	1671
0.2-0.3	4071
0.3-0.4	10206
0.4-0.5	8305
0.5-0.6	3928
0.6-0.7	6080
0.7-0.8	4910
0.8-0.85	1916
0.85-0.9	955
0.9-0.95	234
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC470555
0.9778	High Similarity	NPC472343
0.964	High Similarity	NPC57470
0.963	High Similarity	NPC474624
0.963	High Similarity	NPC138047
0.963	High Similarity	NPC131782
0.9571	High Similarity	NPC180477
0.9571	High Similarity	NPC285748
0.9571	High Similarity	NPC297886
0.9571	High Similarity	NPC249942
0.9565	High Similarity	NPC36181
0.9559	High Similarity	NPC183639
0.9559	High Similarity	NPC219584
0.9559	High Similarity	NPC470083
0.9559	High Similarity	NPC199458
0.9504	High Similarity	NPC208303
0.9504	High Similarity	NPC161864
0.9504	High Similarity	NPC469933
0.9496	High Similarity	NPC470296
0.9496	High Similarity	NPC196459
0.9496	High Similarity	NPC112791
0.9496	High Similarity	NPC94794
0.9496	High Similarity	NPC188632
0.9496	High Similarity	NPC87609
0.9489	High Similarity	NPC241975
0.9489	High Similarity	NPC19476
0.9485	High Similarity	NPC38153
0.9481	High Similarity	NPC101752
0.9437	High Similarity	NPC469932
0.9433	High Similarity	NPC140120
0.9429	High Similarity	NPC178627
0.9429	High Similarity	NPC206212
0.9429	High Similarity	NPC1886
0.9429	High Similarity	NPC196137
0.9429	High Similarity	NPC71184
0.9429	High Similarity	NPC469953
0.9429	High Similarity	NPC469935
0.9412	High Similarity	NPC470983
0.9412	High Similarity	NPC470982
0.9371	High Similarity	NPC151973
0.9362	High Similarity	NPC470322
0.9362	High Similarity	NPC181388
0.9362	High Similarity	NPC154217
0.9296	High Similarity	NPC474108
0.9296	High Similarity	NPC177995
0.9286	High Similarity	NPC62840
0.9286	High Similarity	NPC59739
0.9286	High Similarity	NPC112829
0.9286	High Similarity	NPC214236
0.9286	High Similarity	NPC293852
0.9286	High Similarity	NPC299080
0.9286	High Similarity	NPC217083
0.9286	High Similarity	NPC470556
0.9286	High Similarity	NPC294432
0.9286	High Similarity	NPC78803
0.9275	High Similarity	NPC470668
0.9275	High Similarity	NPC254168
0.9275	High Similarity	NPC272844
0.9275	High Similarity	NPC268178
0.9275	High Similarity	NPC180501
0.9275	High Similarity	NPC54820
0.9275	High Similarity	NPC248995
0.9275	High Similarity	NPC470669
0.922	High Similarity	NPC96216
0.922	High Similarity	NPC470553
0.922	High Similarity	NPC184738
0.922	High Similarity	NPC474939
0.922	High Similarity	NPC307895
0.922	High Similarity	NPC33653
0.922	High Similarity	NPC470909
0.9214	High Similarity	NPC64908
0.9214	High Similarity	NPC147688
0.9214	High Similarity	NPC205006
0.9214	High Similarity	NPC156590
0.9214	High Similarity	NPC316560
0.9214	High Similarity	NPC118840
0.9214	High Similarity	NPC316911
0.9214	High Similarity	NPC201820
0.9209	High Similarity	NPC55018
0.9209	High Similarity	NPC220062
0.9209	High Similarity	NPC301217
0.9209	High Similarity	NPC303633
0.9209	High Similarity	NPC53181
0.9209	High Similarity	NPC96565
0.9209	High Similarity	NPC217186
0.9209	High Similarity	NPC23257
0.9209	High Similarity	NPC216978
0.9209	High Similarity	NPC240305
0.9203	High Similarity	NPC332594
0.9179	High Similarity	NPC21378
0.9179	High Similarity	NPC470987
0.9167	High Similarity	NPC164205
0.9167	High Similarity	NPC104236
0.9167	High Similarity	NPC19238
0.9155	High Similarity	NPC470554
0.9155	High Similarity	NPC118059
0.9155	High Similarity	NPC133060
0.9155	High Similarity	NPC288910
0.9149	High Similarity	NPC321148
0.9149	High Similarity	NPC321629
0.9149	High Similarity	NPC326193
0.9149	High Similarity	NPC11561
0.9149	High Similarity	NPC226636
0.9149	High Similarity	NPC323884
0.9143	High Similarity	NPC172986
0.9143	High Similarity	NPC159275
0.9143	High Similarity	NPC261227
0.9143	High Similarity	NPC150522
0.9143	High Similarity	NPC305355
0.9143	High Similarity	NPC235239
0.9143	High Similarity	NPC471587
0.9143	High Similarity	NPC475680
0.9143	High Similarity	NPC270883
0.9143	High Similarity	NPC241100
0.9137	High Similarity	NPC131130
0.9137	High Similarity	NPC201395
0.913	High Similarity	NPC174999
0.9103	High Similarity	NPC474735
0.9097	High Similarity	NPC211811
0.9091	High Similarity	NPC470910
0.9091	High Similarity	NPC220418
0.9091	High Similarity	NPC329678
0.9085	High Similarity	NPC219915
0.9085	High Similarity	NPC38219
0.9078	High Similarity	NPC282300
0.9078	High Similarity	NPC103362
0.9078	High Similarity	NPC110969
0.9071	High Similarity	NPC473076
0.9071	High Similarity	NPC473209
0.9071	High Similarity	NPC18260
0.9071	High Similarity	NPC78913
0.9065	High Similarity	NPC253616
0.9058	High Similarity	NPC151113
0.9058	High Similarity	NPC46869
0.9051	High Similarity	NPC108113
0.9051	High Similarity	NPC93756
0.9044	High Similarity	NPC185624
0.9041	High Similarity	NPC290671
0.9028	High Similarity	NPC166757
0.9028	High Similarity	NPC79469
0.9028	High Similarity	NPC104406
0.9028	High Similarity	NPC97716
0.9028	High Similarity	NPC14001
0.9028	High Similarity	NPC237635
0.9028	High Similarity	NPC201731
0.9028	High Similarity	NPC24673
0.9021	High Similarity	NPC311741
0.9021	High Similarity	NPC319752
0.9021	High Similarity	NPC257236
0.9021	High Similarity	NPC234629
0.9021	High Similarity	NPC278175
0.9014	High Similarity	NPC144499
0.9014	High Similarity	NPC200694
0.9014	High Similarity	NPC472344
0.9014	High Similarity	NPC266725
0.9007	High Similarity	NPC307990
0.9007	High Similarity	NPC16455
0.9007	High Similarity	NPC69769
0.9	High Similarity	NPC470671
0.9	High Similarity	NPC474487
0.9	High Similarity	NPC474504
0.9	High Similarity	NPC470672
0.8993	High Similarity	NPC13408
0.8993	High Similarity	NPC268081
0.8986	High Similarity	NPC469934
0.8986	High Similarity	NPC125920
0.8986	High Similarity	NPC108937
0.8986	High Similarity	NPC279218
0.8978	High Similarity	NPC10971
0.8978	High Similarity	NPC470988
0.8973	High Similarity	NPC158866
0.8973	High Similarity	NPC470908
0.8973	High Similarity	NPC471984
0.8973	High Similarity	NPC180351
0.8973	High Similarity	NPC321387
0.8973	High Similarity	NPC327059
0.8966	High Similarity	NPC6511
0.8966	High Similarity	NPC321623
0.8966	High Similarity	NPC189087
0.8966	High Similarity	NPC266572
0.8966	High Similarity	NPC244407
0.8966	High Similarity	NPC37139
0.8966	High Similarity	NPC161191
0.8958	High Similarity	NPC111786
0.8958	High Similarity	NPC214774
0.8958	High Similarity	NPC153758
0.8958	High Similarity	NPC475052
0.8958	High Similarity	NPC312973
0.8958	High Similarity	NPC54577
0.8958	High Similarity	NPC176229
0.8958	High Similarity	NPC476088
0.8958	High Similarity	NPC88964
0.8958	High Similarity	NPC470647
0.8958	High Similarity	NPC124729
0.8958	High Similarity	NPC195621
0.8958	High Similarity	NPC474161
0.8958	High Similarity	NPC83357
0.8958	High Similarity	NPC267375
0.8958	High Similarity	NPC20488
0.8958	High Similarity	NPC301276

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 NPC221173 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	976
0.2-0.3	1592
0.3-0.4	2637
0.4-0.5	1934
0.5-0.6	1145
0.6-0.7	349
0.7-0.8	122
0.8-0.85	41
0.85-0.9	14
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9021	High Similarity	NPD7410	Clinical (unspecified phase)
0.8889	High Similarity	NPD4378	Clinical (unspecified phase)
0.8658	High Similarity	NPD7411	Suspended
0.8542	High Similarity	NPD2800	Approved
0.8531	High Similarity	NPD1552	Clinical (unspecified phase)
0.8531	High Similarity	NPD1550	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7075	Discontinued
0.8477	Intermediate Similarity	NPD6801	Discontinued
0.8472	Intermediate Similarity	NPD1549	Phase 2
0.844	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD5124	Phase 1
0.8421	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD7819	Suspended
0.8414	Intermediate Similarity	NPD1243	Approved
0.8392	Intermediate Similarity	NPD1510	Phase 2
0.838	Intermediate Similarity	NPD6651	Approved
0.8378	Intermediate Similarity	NPD2532	Approved
0.8378	Intermediate Similarity	NPD2534	Approved
0.8378	Intermediate Similarity	NPD2533	Approved
0.8369	Intermediate Similarity	NPD1240	Approved
0.8356	Intermediate Similarity	NPD3750	Approved
0.8345	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2796	Approved
0.8311	Intermediate Similarity	NPD6799	Approved
0.8301	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD3749	Approved
0.8252	Intermediate Similarity	NPD1607	Approved
0.8247	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD4380	Phase 2
0.8194	Intermediate Similarity	NPD7768	Phase 2
0.8188	Intermediate Similarity	NPD1511	Approved
0.8176	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD920	Approved
0.8121	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6599	Discontinued
0.8102	Intermediate Similarity	NPD422	Phase 1
0.8099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD2313	Discontinued
0.8079	Intermediate Similarity	NPD1512	Approved
0.8065	Intermediate Similarity	NPD2801	Approved
0.8043	Intermediate Similarity	NPD9717	Approved
0.8026	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2799	Discontinued
0.8014	Intermediate Similarity	NPD3748	Approved
0.8013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD1203	Approved
0.8	Intermediate Similarity	NPD1934	Approved
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD3268	Approved
0.7959	Intermediate Similarity	NPD2935	Discontinued
0.7959	Intermediate Similarity	NPD1551	Phase 2
0.7914	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5401	Approved
0.7872	Intermediate Similarity	NPD2797	Approved
0.7867	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6232	Discontinued
0.7818	Intermediate Similarity	NPD5953	Discontinued
0.7806	Intermediate Similarity	NPD3226	Approved
0.7805	Intermediate Similarity	NPD7286	Phase 2
0.7801	Intermediate Similarity	NPD3225	Approved
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.777	Intermediate Similarity	NPD4308	Phase 3
0.777	Intermediate Similarity	NPD7033	Discontinued
0.7764	Intermediate Similarity	NPD6959	Discontinued
0.775	Intermediate Similarity	NPD919	Approved
0.7736	Intermediate Similarity	NPD3882	Suspended
0.7724	Intermediate Similarity	NPD1296	Phase 2
0.7716	Intermediate Similarity	NPD5711	Approved
0.7716	Intermediate Similarity	NPD5710	Approved
0.7708	Intermediate Similarity	NPD6832	Phase 2
0.7673	Intermediate Similarity	NPD5402	Approved
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7625	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3266	Approved
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3267	Approved
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6100	Approved
0.76	Intermediate Similarity	NPD6099	Approved
0.759	Intermediate Similarity	NPD7054	Approved
0.759	Intermediate Similarity	NPD5844	Phase 1
0.756	Intermediate Similarity	NPD6559	Discontinued
0.755	Intermediate Similarity	NPD2344	Approved
0.7545	Intermediate Similarity	NPD7074	Phase 3
0.7545	Intermediate Similarity	NPD7472	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4307	Phase 2
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD5494	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7456	Intermediate Similarity	NPD7251	Discontinued
0.745	Intermediate Similarity	NPD447	Suspended
0.7448	Intermediate Similarity	NPD2798	Approved
0.7429	Intermediate Similarity	NPD9545	Approved
0.7421	Intermediate Similarity	NPD6585	Discontinued
0.7417	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7808	Phase 3
0.741	Intermediate Similarity	NPD9493	Approved
0.7401	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1465	Phase 2
0.7375	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4287	Approved
0.7355	Intermediate Similarity	NPD2309	Approved
0.7347	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4288	Approved
0.7338	Intermediate Similarity	NPD2654	Approved
0.7329	Intermediate Similarity	NPD1019	Discontinued
0.7305	Intermediate Similarity	NPD1548	Phase 1
0.7292	Intermediate Similarity	NPD1608	Approved
0.7278	Intermediate Similarity	NPD5049	Phase 3
0.7267	Intermediate Similarity	NPD5890	Approved
0.7267	Intermediate Similarity	NPD5889	Approved
0.7267	Intermediate Similarity	NPD943	Approved
0.7261	Intermediate Similarity	NPD7390	Discontinued
0.7255	Intermediate Similarity	NPD5404	Approved
0.7255	Intermediate Similarity	NPD5406	Approved
0.7255	Intermediate Similarity	NPD5405	Approved
0.7255	Intermediate Similarity	NPD5408	Approved
0.7248	Intermediate Similarity	NPD3764	Approved
0.7233	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4908	Phase 1
0.7229	Intermediate Similarity	NPD1247	Approved
0.7226	Intermediate Similarity	NPD1652	Phase 2
0.7222	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD230	Phase 1
0.7219	Intermediate Similarity	NPD1933	Approved
0.7193	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4363	Phase 3
0.7191	Intermediate Similarity	NPD4360	Phase 2
0.7181	Intermediate Similarity	NPD4625	Phase 3
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD1729	Discontinued
0.7134	Intermediate Similarity	NPD2354	Approved
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4749	Approved
0.7107	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1610	Phase 2
0.7101	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6002	Phase 3
0.7097	Intermediate Similarity	NPD6004	Phase 3
0.7097	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6005	Phase 3
0.7083	Intermediate Similarity	NPD17	Approved
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.7079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7003	Approved
0.7055	Intermediate Similarity	NPD1481	Phase 2
0.7044	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3926	Phase 2
0.7037	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5535	Approved
0.6987	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2353	Approved
0.6986	Remote Similarity	NPD1535	Discovery
0.6957	Remote Similarity	NPD74	Approved
0.6957	Remote Similarity	NPD9266	Approved
0.6954	Remote Similarity	NPD6104	Discontinued
0.6952	Remote Similarity	NPD7584	Approved
0.695	Remote Similarity	NPD1241	Discontinued
0.6944	Remote Similarity	NPD1894	Discontinued
0.6939	Remote Similarity	NPD3972	Approved
0.6923	Remote Similarity	NPD7199	Phase 2
0.6923	Remote Similarity	NPD4476	Approved
0.6923	Remote Similarity	NPD4477	Approved
0.6919	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3887	Approved
0.6908	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2403	Approved
0.6887	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9263	Approved
0.6884	Remote Similarity	NPD9264	Approved
0.6884	Remote Similarity	NPD9267	Approved
0.6883	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD8313	Approved
0.6875	Remote Similarity	NPD8312	Approved
0.6872	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1201	Approved
0.6871	Remote Similarity	NPD1653	Approved
0.6863	Remote Similarity	NPD6233	Phase 2
0.6859	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD8434	Phase 2
0.6852	Remote Similarity	NPD6273	Approved
0.6849	Remote Similarity	NPD4626	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