NPASS Compound

Structure

NPC470555 OpenBabel07101718272D 27 29 0 0 1 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 -2.5981 1.5000 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 -0.5000 -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 -1.7321 2.0000 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 1.7321 -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 -0.8660 1.5000 0.0000 C 0 0 3 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 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 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 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 12 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 8 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 24 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.18
Volume:	388.895
LogP:	5.51
LogD:	4.65
LogS:	-4.168
# 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:	0.6
Synthetic Accessibility Score:	3.613
Fsp3:	0.455
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:	-4.749
MDCK Permeability:	1.7408630810678005e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	100.32235717773438%
Volume Distribution (VD):	0.733
Pgp-substrate:	1.5849647521972656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.808
CYP1A2-substrate:	0.827
CYP2C19-inhibitor:	0.832
CYP2C19-substrate:	0.352
CYP2C9-inhibitor:	0.91
CYP2C9-substrate:	0.77
CYP2D6-inhibitor:	0.77
CYP2D6-substrate:	0.228
CYP3A4-inhibitor:	0.537
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	2.775
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.782
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.224
Rat Oral Acute Toxicity:	0.875
Maximum Recommended Daily Dose:	0.54
Skin Sensitization:	0.329
Carcinogencity:	0.888
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.629

Download Data

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

Natural Product: NPC470555

Natural Product ID:	NPC470555
*Common Name:**	Mammea B/Ab Cyclo D
IUPAC Name:	5-hydroxy-8,8-dimethyl-6-(2-methylbutanoyl)-4-propylpyrano[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	UOITWFKGLACCRG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H26O5/c1-6-8-13-11-15(23)26-20-14-9-10-22(4,5)27-21(14)17(19(25)16(13)20)18(24)12(3)7-2/h9-12,25H,6-8H2,1-5H3
SMILES:	CCCc1cc(=O)oc2c1c(O)c(C(=O)C(CC)C)c1c2C=CC(O1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2064611
PubChem CID:	15223666
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	1
Others	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	10.6	%	PMID[487888]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	13.3	%	PMID[487888]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	30000.0	nM	PMID[487888]

☑ 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 NPC470555 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	373
0.1-0.2	1635
0.2-0.3	3921
0.3-0.4	9807
0.4-0.5	8877
0.5-0.6	3876
0.6-0.7	6095
0.7-0.8	5070
0.8-0.85	1895
0.85-0.9	888
0.9-0.95	211
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC221173
0.9852	High Similarity	NPC472343
0.9704	High Similarity	NPC138047
0.9704	High Similarity	NPC474624
0.9704	High Similarity	NPC131782
0.9643	High Similarity	NPC297886
0.9643	High Similarity	NPC249942
0.9632	High Similarity	NPC199458
0.9632	High Similarity	NPC183639
0.9632	High Similarity	NPC219584
0.9632	High Similarity	NPC470083
0.9574	High Similarity	NPC469933
0.9574	High Similarity	NPC161864
0.9574	High Similarity	NPC208303
0.9571	High Similarity	NPC57470
0.9568	High Similarity	NPC470296
0.9568	High Similarity	NPC87609
0.9568	High Similarity	NPC188632
0.9568	High Similarity	NPC112791
0.9568	High Similarity	NPC196459
0.9568	High Similarity	NPC94794
0.9562	High Similarity	NPC19476
0.9562	High Similarity	NPC241975
0.9507	High Similarity	NPC469932
0.9504	High Similarity	NPC180477
0.9504	High Similarity	NPC285748
0.95	High Similarity	NPC196137
0.95	High Similarity	NPC1886
0.95	High Similarity	NPC469935
0.95	High Similarity	NPC178627
0.9496	High Similarity	NPC36181
0.9433	High Similarity	NPC470322
0.9433	High Similarity	NPC154217
0.9433	High Similarity	NPC181388
0.9416	High Similarity	NPC38153
0.9412	High Similarity	NPC101752
0.9366	High Similarity	NPC474108
0.9366	High Similarity	NPC140120
0.9366	High Similarity	NPC177995
0.9362	High Similarity	NPC206212
0.9362	High Similarity	NPC469953
0.9362	High Similarity	NPC71184
0.9357	High Similarity	NPC470556
0.9348	High Similarity	NPC470668
0.9348	High Similarity	NPC470669
0.9343	High Similarity	NPC470983
0.9343	High Similarity	NPC470982
0.9306	High Similarity	NPC151973
0.9291	High Similarity	NPC470909
0.9291	High Similarity	NPC307895
0.9291	High Similarity	NPC470553
0.9291	High Similarity	NPC96216
0.9291	High Similarity	NPC474939
0.9286	High Similarity	NPC201820
0.9281	High Similarity	NPC240305
0.9236	High Similarity	NPC104236
0.9236	High Similarity	NPC164205
0.9236	High Similarity	NPC19238
0.9225	High Similarity	NPC288910
0.9225	High Similarity	NPC118059
0.9225	High Similarity	NPC133060
0.9225	High Similarity	NPC470554
0.922	High Similarity	NPC217083
0.922	High Similarity	NPC294432
0.922	High Similarity	NPC78803
0.922	High Similarity	NPC299080
0.922	High Similarity	NPC112829
0.922	High Similarity	NPC293852
0.922	High Similarity	NPC59739
0.922	High Similarity	NPC214236
0.922	High Similarity	NPC62840
0.9209	High Similarity	NPC180501
0.9209	High Similarity	NPC272844
0.9209	High Similarity	NPC254168
0.9209	High Similarity	NPC268178
0.9209	High Similarity	NPC248995
0.9209	High Similarity	NPC54820
0.9172	High Similarity	NPC474735
0.9161	High Similarity	NPC470910
0.9161	High Similarity	NPC329678
0.9155	High Similarity	NPC184738
0.9155	High Similarity	NPC33653
0.9149	High Similarity	NPC205006
0.9149	High Similarity	NPC316911
0.9149	High Similarity	NPC282300
0.9149	High Similarity	NPC316560
0.9149	High Similarity	NPC147688
0.9149	High Similarity	NPC156590
0.9149	High Similarity	NPC64908
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	NPC220062
0.9143	High Similarity	NPC473209
0.9143	High Similarity	NPC23257
0.9143	High Similarity	NPC217186
0.9143	High Similarity	NPC55018
0.9143	High Similarity	NPC301217
0.9137	High Similarity	NPC332594
0.9118	High Similarity	NPC185624
0.9111	High Similarity	NPC21378
0.9111	High Similarity	NPC470987
0.911	High Similarity	NPC290671
0.9085	High Similarity	NPC321629
0.9085	High Similarity	NPC226636
0.9085	High Similarity	NPC321148
0.9085	High Similarity	NPC326193
0.9085	High Similarity	NPC11561
0.9085	High Similarity	NPC472344
0.9085	High Similarity	NPC323884
0.9078	High Similarity	NPC150522
0.9078	High Similarity	NPC261227
0.9078	High Similarity	NPC235239
0.9078	High Similarity	NPC159275
0.9078	High Similarity	NPC172986
0.9078	High Similarity	NPC471587
0.9078	High Similarity	NPC305355
0.9078	High Similarity	NPC241100
0.9078	High Similarity	NPC475680
0.9078	High Similarity	NPC270883
0.9071	High Similarity	NPC470672
0.9071	High Similarity	NPC201395
0.9071	High Similarity	NPC470671
0.9071	High Similarity	NPC131130
0.9071	High Similarity	NPC474487
0.9071	High Similarity	NPC474504
0.9065	High Similarity	NPC174999
0.9054	High Similarity	NPC469934
0.9051	High Similarity	NPC470988
0.9041	High Similarity	NPC321387
0.9041	High Similarity	NPC327059
0.9041	High Similarity	NPC158866
0.9041	High Similarity	NPC470908
0.9034	High Similarity	NPC211811
0.9028	High Similarity	NPC474161
0.9028	High Similarity	NPC476088
0.9028	High Similarity	NPC220418
0.9021	High Similarity	NPC219915
0.9021	High Similarity	NPC38219
0.9014	High Similarity	NPC103362
0.9014	High Similarity	NPC110969
0.9007	High Similarity	NPC78913
0.9007	High Similarity	NPC473076
0.9007	High Similarity	NPC18260
0.9	High Similarity	NPC253616
0.8993	High Similarity	NPC109967
0.8993	High Similarity	NPC129053
0.8993	High Similarity	NPC474738
0.8993	High Similarity	NPC151113
0.8993	High Similarity	NPC321372
0.8993	High Similarity	NPC469936
0.8993	High Similarity	NPC46869
0.8993	High Similarity	NPC474609
0.8993	High Similarity	NPC78554
0.8993	High Similarity	NPC475797
0.8986	High Similarity	NPC470984
0.8986	High Similarity	NPC108113
0.8986	High Similarity	NPC93756
0.898	High Similarity	NPC209142
0.898	High Similarity	NPC312549
0.8966	High Similarity	NPC282335
0.8966	High Similarity	NPC79469
0.8966	High Similarity	NPC218300
0.8966	High Similarity	NPC14001
0.8966	High Similarity	NPC24673
0.8966	High Similarity	NPC201731
0.8966	High Similarity	NPC97716
0.8966	High Similarity	NPC237635
0.8966	High Similarity	NPC166757
0.8966	High Similarity	NPC104406
0.8958	High Similarity	NPC257236
0.8958	High Similarity	NPC326500
0.8958	High Similarity	NPC131568
0.8958	High Similarity	NPC278175
0.8958	High Similarity	NPC234629
0.8958	High Similarity	NPC131579
0.8958	High Similarity	NPC311741
0.8958	High Similarity	NPC319752
0.8951	High Similarity	NPC266725
0.8951	High Similarity	NPC204469
0.8951	High Similarity	NPC144499
0.8951	High Similarity	NPC200694
0.8944	High Similarity	NPC16455
0.8944	High Similarity	NPC69769
0.8944	High Similarity	NPC307990
0.8944	High Similarity	NPC477272
0.8936	High Similarity	NPC36414
0.8929	High Similarity	NPC187826
0.8929	High Similarity	NPC268081
0.8929	High Similarity	NPC156910
0.8929	High Similarity	NPC13408
0.8926	High Similarity	NPC108937
0.8926	High Similarity	NPC279218
0.8921	High Similarity	NPC125920
0.8913	High Similarity	NPC10971
0.8912	High Similarity	NPC471984
0.8912	High Similarity	NPC180351
0.8904	High Similarity	NPC6511

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 NPC470555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	975
0.2-0.3	1589
0.3-0.4	2623
0.4-0.5	1955
0.5-0.6	1142
0.6-0.7	349
0.7-0.8	123
0.8-0.85	39
0.85-0.9	12
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8958	High Similarity	NPD7410	Clinical (unspecified phase)
0.8828	High Similarity	NPD4378	Clinical (unspecified phase)
0.86	High Similarity	NPD7411	Suspended
0.8511	High Similarity	NPD5123	Clinical (unspecified phase)
0.8511	High Similarity	NPD5124	Phase 1
0.8483	Intermediate Similarity	NPD2800	Approved
0.8472	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD6651	Approved
0.8442	Intermediate Similarity	NPD7075	Discontinued
0.8421	Intermediate Similarity	NPD6801	Discontinued
0.8414	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1549	Phase 2
0.8366	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD7819	Suspended
0.8356	Intermediate Similarity	NPD1243	Approved
0.8333	Intermediate Similarity	NPD1510	Phase 2
0.8322	Intermediate Similarity	NPD2533	Approved
0.8322	Intermediate Similarity	NPD2534	Approved
0.8322	Intermediate Similarity	NPD2532	Approved
0.8312	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1240	Approved
0.8299	Intermediate Similarity	NPD3750	Approved
0.8276	Intermediate Similarity	NPD2796	Approved
0.8255	Intermediate Similarity	NPD6799	Approved
0.8247	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3749	Approved
0.8194	Intermediate Similarity	NPD1607	Approved
0.817	Intermediate Similarity	NPD4380	Phase 2
0.8141	Intermediate Similarity	NPD7768	Phase 2
0.8133	Intermediate Similarity	NPD1511	Approved
0.8125	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD920	Approved
0.8082	Intermediate Similarity	NPD2799	Discontinued
0.8067	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD6599	Discontinued
0.8043	Intermediate Similarity	NPD422	Phase 1
0.8042	Intermediate Similarity	NPD2313	Discontinued
0.8042	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD3268	Approved
0.8026	Intermediate Similarity	NPD1512	Approved
0.8013	Intermediate Similarity	NPD2801	Approved
0.7986	Intermediate Similarity	NPD9717	Approved
0.7975	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD5403	Approved
0.7962	Intermediate Similarity	NPD3817	Phase 2
0.7961	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD3748	Approved
0.7949	Intermediate Similarity	NPD1934	Approved
0.7943	Intermediate Similarity	NPD1203	Approved
0.7943	Intermediate Similarity	NPD2797	Approved
0.7933	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2935	Discontinued
0.7905	Intermediate Similarity	NPD1551	Phase 2
0.7866	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7473	Discontinued
0.7843	Intermediate Similarity	NPD5401	Approved
0.7778	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD5953	Discontinued
0.7758	Intermediate Similarity	NPD7286	Phase 2
0.7756	Intermediate Similarity	NPD3226	Approved
0.7746	Intermediate Similarity	NPD3225	Approved
0.7718	Intermediate Similarity	NPD7033	Discontinued
0.7718	Intermediate Similarity	NPD4308	Phase 3
0.7716	Intermediate Similarity	NPD6959	Discontinued
0.7702	Intermediate Similarity	NPD919	Approved
0.7692	Intermediate Similarity	NPD3267	Approved
0.7692	Intermediate Similarity	NPD3266	Approved
0.7688	Intermediate Similarity	NPD3882	Suspended
0.7679	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1296	Phase 2
0.7669	Intermediate Similarity	NPD5710	Approved
0.7669	Intermediate Similarity	NPD5711	Approved
0.7667	Intermediate Similarity	NPD6100	Approved
0.7667	Intermediate Similarity	NPD6099	Approved
0.7655	Intermediate Similarity	NPD6832	Phase 2
0.7625	Intermediate Similarity	NPD5402	Approved
0.7616	Intermediate Similarity	NPD2346	Discontinued
0.759	Intermediate Similarity	NPD3818	Discontinued
0.7578	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6166	Phase 2
0.7546	Intermediate Similarity	NPD5494	Approved
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.7545	Intermediate Similarity	NPD7054	Approved
0.7517	Intermediate Similarity	NPD2798	Approved
0.7515	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD7472	Approved
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7456	Intermediate Similarity	NPD6797	Phase 2
0.745	Intermediate Similarity	NPD4307	Phase 2
0.7438	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD411	Approved
0.7432	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7251	Discontinued
0.74	Intermediate Similarity	NPD447	Suspended
0.7376	Intermediate Similarity	NPD9545	Approved
0.7375	Intermediate Similarity	NPD6585	Discontinued
0.7368	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7808	Phase 3
0.7361	Intermediate Similarity	NPD1608	Approved
0.736	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD9493	Approved
0.7346	Intermediate Similarity	NPD1465	Phase 2
0.7314	Intermediate Similarity	NPD4287	Approved
0.7308	Intermediate Similarity	NPD2309	Approved
0.7301	Intermediate Similarity	NPD4288	Approved
0.7297	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4908	Phase 1
0.729	Intermediate Similarity	NPD2654	Approved
0.7279	Intermediate Similarity	NPD1019	Discontinued
0.7254	Intermediate Similarity	NPD1548	Phase 1
0.7247	Intermediate Similarity	NPD4360	Phase 2
0.7247	Intermediate Similarity	NPD4363	Phase 3
0.7233	Intermediate Similarity	NPD5049	Phase 3
0.7222	Intermediate Similarity	NPD5890	Approved
0.7222	Intermediate Similarity	NPD5889	Approved
0.7219	Intermediate Similarity	NPD943	Approved
0.7215	Intermediate Similarity	NPD7390	Discontinued
0.7208	Intermediate Similarity	NPD5408	Approved
0.7208	Intermediate Similarity	NPD5405	Approved
0.7208	Intermediate Similarity	NPD5406	Approved
0.7208	Intermediate Similarity	NPD5404	Approved
0.7207	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4361	Phase 2
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.72	Intermediate Similarity	NPD3764	Approved
0.7192	Intermediate Similarity	NPD4749	Approved
0.7188	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1247	Approved
0.7179	Intermediate Similarity	NPD1652	Phase 2
0.7172	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1610	Phase 2
0.7171	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD230	Phase 1
0.7171	Intermediate Similarity	NPD1933	Approved
0.717	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6002	Phase 3
0.7161	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6004	Phase 3
0.7161	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6005	Phase 3
0.7161	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD17	Approved
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7134	Intermediate Similarity	NPD7003	Approved
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7099	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1164	Approved
0.7093	Intermediate Similarity	NPD1729	Discontinued
0.7089	Intermediate Similarity	NPD2354	Approved
0.7086	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1481	Phase 2
0.7	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7199	Phase 2
0.6974	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2403	Approved
0.695	Remote Similarity	NPD5535	Approved
0.6948	Remote Similarity	NPD6355	Discontinued
0.6943	Remote Similarity	NPD2353	Approved
0.6943	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1535	Discovery
0.6932	Remote Similarity	NPD8313	Approved
0.6932	Remote Similarity	NPD8312	Approved
0.6915	Remote Similarity	NPD7584	Approved
0.6914	Remote Similarity	NPD6104	Discontinued
0.6914	Remote Similarity	NPD6273	Approved
0.691	Remote Similarity	NPD8434	Phase 2
0.6906	Remote Similarity	NPD9266	Approved
0.6906	Remote Similarity	NPD74	Approved
0.6901	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1241	Discontinued
0.6897	Remote Similarity	NPD1894	Discontinued
0.6892	Remote Similarity	NPD3972	Approved
0.6883	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4476	Approved
0.6879	Remote Similarity	NPD4477	Approved
0.6875	Remote Similarity	NPD3887	Approved
0.6848	Remote Similarity	NPD6502	Phase 2
0.6842	Remote Similarity	NPD2614	Approved
0.6842	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9263	Approved
0.6835	Remote Similarity	NPD9264	Approved
0.6835	Remote Similarity	NPD9267	Approved
0.6835	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1653	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