NPASS Compound

Structure

NPC473023 OpenBabel07101719252D 31 32 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 -5.1962 -6.0000 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 -9.6603 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1603 -7.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 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 -6.9282 -6.0000 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 -6.9282 -7.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -7.7942 -7.5000 0.0000 C 0 0 3 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -6.0000 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 15 1 0 0 0 0 2 16 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 17 3 1 6 0 0 0 17 31 1 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 23 2 0 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 24 29 2 0 0 0 0 24 31 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.25
Volume:	460.766
LogP:	4.531
LogD:	3.492
LogS:	-3.282
# Rotatable Bonds:	9
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	4.056
Fsp3:	0.56
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:	-4.916
MDCK Permeability:	2.6183568479609676e-05
Pgp-inhibitor:	0.156
Pgp-substrate:	0.251
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.21
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	97.49298858642578%
Volume Distribution (VD):	0.32
Pgp-substrate:	1.0247045755386353%

ADMET: Metabolism

CYP1A2-inhibitor:	0.24
CYP1A2-substrate:	0.144
CYP2C19-inhibitor:	0.147
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.394
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.872
CYP2D6-substrate:	0.417
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	5.749
Half-life (T1/2):	0.713

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.223
Drug-inuced Liver Injury (DILI):	0.207
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.88
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.152

Download Data

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

Natural Product: NPC473023

Natural Product ID:	NPC473023
*Common Name:**	CBQSQQCAFNEQFL-AVSQOZGVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CBQSQQCAFNEQFL-AVSQOZGVSA-N
Standard InCHI:	InChI=1S/C25H36O6/c1-15(7-6-8-16(2)10-12-22(28)25(4,5)30)9-11-18-19-13-17(3)31-24(29)23(19)21(27)14-20(18)26/h8-9,14,17,22,26-28,30H,6-7,10-13H2,1-5H3/b15-9+,16-8+/t17-,22?/m1/s1
SMILES:	CC1CC2=C(C(=CC(=C2C(=O)O1)O)O)CC=C(C)CCC=C(C)CCC(C(C)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3601069
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO33271	penicillium verruculosum	Species	Aspergillaceae	Eukaryota	n.a.	Indonesian	n.a.	PMID[26115570]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	40.0	%	PMID[544006]

☑ 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 NPC473023 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	319
0.1-0.2	1277
0.2-0.3	3035
0.3-0.4	6866
0.4-0.5	11184
0.5-0.6	4780
0.6-0.7	6240
0.7-0.8	7122
0.8-0.85	1528
0.85-0.9	262
0.9-0.95	78
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC472604
0.964	High Similarity	NPC472605
0.9568	High Similarity	NPC472601
0.9568	High Similarity	NPC472600
0.9504	High Similarity	NPC471731
0.9504	High Similarity	NPC159721
0.95	High Similarity	NPC472603
0.9437	High Similarity	NPC42540
0.9437	High Similarity	NPC151607
0.9433	High Similarity	NPC471733
0.9429	High Similarity	NPC158472
0.9424	High Similarity	NPC472602
0.9424	High Similarity	NPC94248
0.9424	High Similarity	NPC212693
0.9366	High Similarity	NPC472610
0.9362	High Similarity	NPC53649
0.9357	High Similarity	NPC88269
0.9353	High Similarity	NPC194579
0.9353	High Similarity	NPC70380
0.9296	High Similarity	NPC82913
0.9286	High Similarity	NPC191835
0.9281	High Similarity	NPC235115
0.9247	High Similarity	NPC270160
0.9247	High Similarity	NPC237440
0.9241	High Similarity	NPC471734
0.9236	High Similarity	NPC83272
0.9231	High Similarity	NPC469542
0.9225	High Similarity	NPC158634
0.922	High Similarity	NPC139634
0.922	High Similarity	NPC105456
0.922	High Similarity	NPC32360
0.9214	High Similarity	NPC71256
0.9172	High Similarity	NPC471735
0.9167	High Similarity	NPC210425
0.9167	High Similarity	NPC280404
0.9167	High Similarity	NPC86373
0.9167	High Similarity	NPC277426
0.9161	High Similarity	NPC322112
0.9161	High Similarity	NPC469579
0.9155	High Similarity	NPC64664
0.9149	High Similarity	NPC478200
0.9149	High Similarity	NPC33144
0.9143	High Similarity	NPC291454
0.9122	High Similarity	NPC70016
0.9122	High Similarity	NPC215921
0.911	High Similarity	NPC53362
0.911	High Similarity	NPC166583
0.9097	High Similarity	NPC51106
0.9097	High Similarity	NPC478202
0.9091	High Similarity	NPC478217
0.9091	High Similarity	NPC67650
0.9091	High Similarity	NPC313123
0.9091	High Similarity	NPC1704
0.9085	High Similarity	NPC247409
0.9085	High Similarity	NPC268052
0.9071	High Similarity	NPC142027
0.9065	High Similarity	NPC153783
0.906	High Similarity	NPC167903
0.9054	High Similarity	NPC179178
0.9048	High Similarity	NPC221352
0.9041	High Similarity	NPC260946
0.9028	High Similarity	NPC474385
0.9021	High Similarity	NPC155205
0.9014	High Similarity	NPC475974
0.9014	High Similarity	NPC221104
0.9007	High Similarity	NPC158481
0.9007	High Similarity	NPC50455
0.9007	High Similarity	NPC472599
0.9	High Similarity	NPC471695
0.9	High Similarity	NPC472799
0.8993	High Similarity	NPC476389
0.898	High Similarity	NPC210320
0.8966	High Similarity	NPC472006
0.8958	High Similarity	NPC37530
0.8958	High Similarity	NPC472035
0.8958	High Similarity	NPC470842
0.8958	High Similarity	NPC478201
0.8958	High Similarity	NPC244923
0.8951	High Similarity	NPC275356
0.8944	High Similarity	NPC474771
0.8944	High Similarity	NPC474849
0.8944	High Similarity	NPC65837
0.8944	High Similarity	NPC149372
0.8944	High Similarity	NPC178467
0.894	High Similarity	NPC16082
0.894	High Similarity	NPC82592
0.8936	High Similarity	NPC27407
0.8933	High Similarity	NPC115249
0.8933	High Similarity	NPC478224
0.8926	High Similarity	NPC56204
0.8926	High Similarity	NPC469619
0.8926	High Similarity	NPC472891
0.8926	High Similarity	NPC469670
0.8921	High Similarity	NPC219892
0.8921	High Similarity	NPC189823
0.8919	High Similarity	NPC73411
0.8919	High Similarity	NPC215711
0.8889	High Similarity	NPC99441
0.8889	High Similarity	NPC470339
0.8882	High Similarity	NPC472050
0.8881	High Similarity	NPC126739
0.8881	High Similarity	NPC197666
0.8874	High Similarity	NPC137301
0.8874	High Similarity	NPC281477
0.8873	High Similarity	NPC156967
0.8867	High Similarity	NPC200773
0.8867	High Similarity	NPC240768
0.8865	High Similarity	NPC175943
0.8859	High Similarity	NPC77325
0.8859	High Similarity	NPC476684
0.8859	High Similarity	NPC4423
0.8851	High Similarity	NPC125801
0.8851	High Similarity	NPC476463
0.8851	High Similarity	NPC81835
0.8851	High Similarity	NPC91902
0.8844	High Similarity	NPC473692
0.8844	High Similarity	NPC257558
0.8831	High Similarity	NPC472055
0.8828	High Similarity	NPC475730
0.8824	High Similarity	NPC246466
0.8824	High Similarity	NPC84935
0.8824	High Similarity	NPC190020
0.8824	High Similarity	NPC77679
0.8824	High Similarity	NPC472889
0.8824	High Similarity	NPC257309
0.8819	High Similarity	NPC474655
0.8816	High Similarity	NPC478230
0.8816	High Similarity	NPC208173
0.8816	High Similarity	NPC69043
0.8816	High Similarity	NPC170189
0.8811	High Similarity	NPC301915
0.8811	High Similarity	NPC135837
0.8811	High Similarity	NPC245058
0.8811	High Similarity	NPC261292
0.8808	High Similarity	NPC184284
0.8808	High Similarity	NPC76041
0.8808	High Similarity	NPC256141
0.8808	High Similarity	NPC273483
0.88	High Similarity	NPC150928
0.8794	High Similarity	NPC180261
0.8794	High Similarity	NPC37299
0.8792	High Similarity	NPC37139
0.8792	High Similarity	NPC471641
0.8792	High Similarity	NPC240253
0.8792	High Similarity	NPC471642
0.8792	High Similarity	NPC240622
0.879	High Similarity	NPC472621
0.8786	High Similarity	NPC214702
0.8786	High Similarity	NPC470831
0.8784	High Similarity	NPC237208
0.8784	High Similarity	NPC107625
0.8784	High Similarity	NPC163846
0.8784	High Similarity	NPC225173
0.8776	High Similarity	NPC478203
0.8776	High Similarity	NPC210966
0.8776	High Similarity	NPC126882
0.8774	High Similarity	NPC117985
0.8767	High Similarity	NPC250755
0.8759	High Similarity	NPC165172
0.8759	High Similarity	NPC168471
0.8758	High Similarity	NPC150227
0.875	High Similarity	NPC478231
0.875	High Similarity	NPC472403
0.875	High Similarity	NPC177307
0.875	High Similarity	NPC192189
0.875	High Similarity	NPC470102
0.875	High Similarity	NPC9121
0.8742	High Similarity	NPC46882
0.8742	High Similarity	NPC132990
0.8734	High Similarity	NPC472622
0.8733	High Similarity	NPC233267
0.8733	High Similarity	NPC291049
0.8732	High Similarity	NPC474394
0.8725	High Similarity	NPC473133
0.8725	High Similarity	NPC47388
0.8725	High Similarity	NPC472036
0.8725	High Similarity	NPC470670
0.8725	High Similarity	NPC8817
0.8716	High Similarity	NPC29577
0.8716	High Similarity	NPC134621
0.8716	High Similarity	NPC472034
0.8714	High Similarity	NPC17840
0.8714	High Similarity	NPC247477
0.871	High Similarity	NPC321399
0.8699	High Similarity	NPC130485
0.8693	High Similarity	NPC99381
0.8693	High Similarity	NPC472890
0.8693	High Similarity	NPC478221
0.8693	High Similarity	NPC199926
0.869	High Similarity	NPC92655
0.869	High Similarity	NPC471819
0.869	High Similarity	NPC52358
0.8684	High Similarity	NPC51824
0.8684	High Similarity	NPC470340
0.8684	High Similarity	NPC470338
0.8684	High Similarity	NPC268992
0.8684	High Similarity	NPC113608
0.8684	High Similarity	NPC470337
0.8684	High Similarity	NPC217447
0.8675	High Similarity	NPC180351

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 NPC473023 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	879
0.2-0.3	1756
0.3-0.4	2584
0.4-0.5	1980
0.5-0.6	1084
0.6-0.7	429
0.7-0.8	147
0.8-0.85	10
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.869	High Similarity	NPD970	Clinical (unspecified phase)
0.8627	High Similarity	NPD7819	Suspended
0.8591	High Similarity	NPD2534	Approved
0.8591	High Similarity	NPD2533	Approved
0.8591	High Similarity	NPD2532	Approved
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8387	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD4380	Phase 2
0.8151	Intermediate Similarity	NPD230	Phase 1
0.8137	Intermediate Similarity	NPD6232	Discontinued
0.8101	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7473	Discontinued
0.8089	Intermediate Similarity	NPD1934	Approved
0.8089	Intermediate Similarity	NPD6801	Discontinued
0.8075	Intermediate Similarity	NPD6959	Discontinued
0.8025	Intermediate Similarity	NPD5711	Approved
0.8025	Intermediate Similarity	NPD7411	Suspended
0.8025	Intermediate Similarity	NPD5710	Approved
0.8	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1549	Phase 2
0.7937	Intermediate Similarity	NPD7768	Phase 2
0.7937	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2935	Discontinued
0.7922	Intermediate Similarity	NPD6799	Approved
0.7892	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1510	Phase 2
0.7861	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6599	Discontinued
0.7844	Intermediate Similarity	NPD7074	Phase 3
0.7843	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1240	Approved
0.7836	Intermediate Similarity	NPD8150	Discontinued
0.7818	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6166	Phase 2
0.7806	Intermediate Similarity	NPD7390	Discontinued
0.7784	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD3749	Approved
0.7764	Intermediate Similarity	NPD3817	Phase 2
0.7756	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6559	Discontinued
0.7738	Intermediate Similarity	NPD7472	Approved
0.7733	Intermediate Similarity	NPD6651	Approved
0.7733	Intermediate Similarity	NPD1607	Approved
0.7727	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3750	Approved
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7718	Intermediate Similarity	NPD943	Approved
0.7716	Intermediate Similarity	NPD3882	Suspended
0.7703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2801	Approved
0.7697	Intermediate Similarity	NPD5408	Approved
0.7697	Intermediate Similarity	NPD5405	Approved
0.7697	Intermediate Similarity	NPD5406	Approved
0.7697	Intermediate Similarity	NPD5404	Approved
0.7697	Intermediate Similarity	NPD2796	Approved
0.7692	Intermediate Similarity	NPD1511	Approved
0.7662	Intermediate Similarity	NPD2800	Approved
0.766	Intermediate Similarity	NPD9545	Approved
0.7647	Intermediate Similarity	NPD7251	Discontinued
0.7632	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3818	Discontinued
0.7602	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7808	Phase 3
0.7595	Intermediate Similarity	NPD1512	Approved
0.7593	Intermediate Similarity	NPD1465	Phase 2
0.7588	Intermediate Similarity	NPD6797	Phase 2
0.7584	Intermediate Similarity	NPD3764	Approved
0.7582	Intermediate Similarity	NPD1551	Phase 2
0.7582	Intermediate Similarity	NPD6100	Approved
0.7582	Intermediate Similarity	NPD6099	Approved
0.7576	Intermediate Similarity	NPD5494	Approved
0.7548	Intermediate Similarity	NPD1243	Approved
0.7548	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5403	Approved
0.7546	Intermediate Similarity	NPD5402	Approved
0.7518	Intermediate Similarity	NPD9493	Approved
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8312	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.7453	Intermediate Similarity	NPD3226	Approved
0.7453	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6190	Approved
0.7438	Intermediate Similarity	NPD920	Approved
0.7434	Intermediate Similarity	NPD5124	Phase 1
0.7434	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7435	Discontinued
0.7423	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD5401	Approved
0.7419	Intermediate Similarity	NPD8151	Discontinued
0.7419	Intermediate Similarity	NPD2346	Discontinued
0.7412	Intermediate Similarity	NPD7228	Approved
0.741	Intermediate Similarity	NPD6234	Discontinued
0.741	Intermediate Similarity	NPD919	Approved
0.7405	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2799	Discontinued
0.7403	Intermediate Similarity	NPD3748	Approved
0.7397	Intermediate Similarity	NPD9269	Phase 2
0.7394	Intermediate Similarity	NPD4966	Approved
0.7394	Intermediate Similarity	NPD4967	Phase 2
0.7394	Intermediate Similarity	NPD4965	Approved
0.7391	Intermediate Similarity	NPD8319	Approved
0.7391	Intermediate Similarity	NPD8320	Phase 1
0.7384	Intermediate Similarity	NPD5953	Discontinued
0.7374	Intermediate Similarity	NPD6534	Approved
0.7374	Intermediate Similarity	NPD6535	Approved
0.7368	Intermediate Similarity	NPD7286	Phase 2
0.7365	Intermediate Similarity	NPD1164	Approved
0.7348	Intermediate Similarity	NPD7700	Phase 2
0.7348	Intermediate Similarity	NPD7699	Phase 2
0.7345	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1201	Approved
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.7312	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD7229	Phase 3
0.7268	Intermediate Similarity	NPD6777	Approved
0.7268	Intermediate Similarity	NPD6781	Approved
0.7268	Intermediate Similarity	NPD6779	Approved
0.7268	Intermediate Similarity	NPD6782	Approved
0.7268	Intermediate Similarity	NPD6778	Approved
0.7268	Intermediate Similarity	NPD6780	Approved
0.7268	Intermediate Similarity	NPD6776	Approved
0.7255	Intermediate Similarity	NPD4060	Phase 1
0.7249	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7783	Phase 2
0.7248	Intermediate Similarity	NPD1470	Approved
0.7241	Intermediate Similarity	NPD9268	Approved
0.7237	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6832	Phase 2
0.7209	Intermediate Similarity	NPD3751	Discontinued
0.72	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7874	Approved
0.7196	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4626	Approved
0.7176	Intermediate Similarity	NPD3787	Discontinued
0.7175	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4625	Phase 3
0.717	Intermediate Similarity	NPD8166	Discontinued
0.7162	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7696	Phase 3
0.7151	Intermediate Similarity	NPD7697	Approved
0.7151	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7133	Intermediate Similarity	NPD1203	Approved
0.7126	Intermediate Similarity	NPD5353	Approved
0.7124	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5691	Approved
0.7117	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7871	Phase 2
0.7112	Intermediate Similarity	NPD7870	Phase 2
0.7097	Intermediate Similarity	NPD6823	Phase 2
0.7097	Intermediate Similarity	NPD447	Suspended
0.7097	Intermediate Similarity	NPD6355	Discontinued
0.7095	Intermediate Similarity	NPD422	Phase 1
0.709	Intermediate Similarity	NPD7701	Phase 2
0.7089	Intermediate Similarity	NPD7266	Discontinued
0.7086	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6663	Approved
0.7067	Intermediate Similarity	NPD1283	Approved
0.7066	Intermediate Similarity	NPD8455	Phase 2
0.7063	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD3027	Phase 3
0.7055	Intermediate Similarity	NPD6273	Approved
0.7047	Intermediate Similarity	NPD1608	Approved
0.7047	Intermediate Similarity	NPD7930	Approved
0.7045	Intermediate Similarity	NPD7240	Approved
0.7045	Intermediate Similarity	NPD7685	Pre-registration
0.7039	Intermediate Similarity	NPD5736	Approved
0.7037	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6213	Phase 3
0.7033	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6212	Phase 3
0.7032	Intermediate Similarity	NPD1613	Approved
0.7032	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2438	Suspended
0.7018	Intermediate Similarity	NPD1247	Approved
0.7013	Intermediate Similarity	NPD2313	Discontinued
0.7013	Intermediate Similarity	NPD411	Approved
0.7007	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4749	Approved
0.7	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD2654	Approved
0.6995	Remote Similarity	NPD4363	Phase 3

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