NPASS Compound

Structure

NPC194579 OpenBabel07101718332D 28 28 0 0 0 0 0 0 0 0999 V2000 0.0000 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -6.5000 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 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 -1.7321 -0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 16 2 0 0 0 0 10 17 1 0 0 0 0 11 17 2 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 18 2 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.25
Volume:	431.809
LogP:	6.824
LogD:	5.098
LogS:	-3.424
# Rotatable Bonds:	10
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	2.998
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.849
MDCK Permeability:	2.5341478249174543e-05
Pgp-inhibitor:	0.693
Pgp-substrate:	0.292
Human Intestinal Absorption (HIA):	0.308
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.141

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	99.4101333618164%
Volume Distribution (VD):	0.502
Pgp-substrate:	0.6797393560409546%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.337
CYP2C19-inhibitor:	0.831
CYP2C19-substrate:	0.192
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.615
CYP3A4-inhibitor:	0.519
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	6.334
Half-life (T1/2):	0.459

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.653
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.673
Skin Sensitization:	0.953
Carcinogencity:	0.035
Eye Corrosion:	0.011
Eye Irritation:	0.913
Respiratory Toxicity:	0.337

Download Data

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

Natural Product: NPC194579

Natural Product ID:	NPC194579
*Common Name:**	Albatrelin A
IUPAC Name:	methyl 4,6-dihydroxy-2-methyl-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzoate
Synonyms:	Albatrelin A
Standard InCHIKey:	XISGBSYLXCXJCJ-OUBUNXTGSA-N
Standard InCHI:	InChI=1S/C24H34O4/c1-16(2)9-7-10-17(3)11-8-12-18(4)13-14-20-19(5)23(24(27)28-6)22(26)15-21(20)25/h9,11,13,15,25-26H,7-8,10,12,14H2,1-6H3/b17-11+,18-13+
SMILES:	CC(=CCC/C(=C/CC/C(=C/Cc1c(C)c(c(cc1O)O)C(=O)OC)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332228
PubChem CID:	71524348
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23305465]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[458372]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[458372]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[458372]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[458372]

☑ 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 NPC194579 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	1464
0.2-0.3	3381
0.3-0.4	7899
0.4-0.5	10954
0.5-0.6	3984
0.6-0.7	7079
0.7-0.8	5959
0.8-0.85	1281
0.85-0.9	289
0.9-0.95	84
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9621	High Similarity	NPC158481
0.9549	High Similarity	NPC70380
0.9538	High Similarity	NPC219892
0.9538	High Similarity	NPC189823
0.9481	High Similarity	NPC472601
0.9481	High Similarity	NPC472600
0.9478	High Similarity	NPC212693
0.9478	High Similarity	NPC94248
0.9478	High Similarity	NPC191835
0.9416	High Similarity	NPC159721
0.9412	High Similarity	NPC472605
0.9412	High Similarity	NPC472604
0.9412	High Similarity	NPC472603
0.9403	High Similarity	NPC71256
0.9394	High Similarity	NPC180261
0.9394	High Similarity	NPC153783
0.9394	High Similarity	NPC37299
0.9353	High Similarity	NPC473023
0.9348	High Similarity	NPC151607
0.9348	High Similarity	NPC42540
0.9338	High Similarity	NPC99441
0.9338	High Similarity	NPC165172
0.9333	High Similarity	NPC33144
0.9333	High Similarity	NPC478200
0.9333	High Similarity	NPC472602
0.9328	High Similarity	NPC50455
0.9313	High Similarity	NPC17840
0.9313	High Similarity	NPC247477
0.9286	High Similarity	NPC125801
0.9275	High Similarity	NPC471731
0.9275	High Similarity	NPC472610
0.927	High Similarity	NPC67650
0.927	High Similarity	NPC37530
0.927	High Similarity	NPC313123
0.927	High Similarity	NPC478217
0.927	High Similarity	NPC53649
0.927	High Similarity	NPC1704
0.9265	High Similarity	NPC275356
0.9265	High Similarity	NPC88269
0.9265	High Similarity	NPC139634
0.9265	High Similarity	NPC105456
0.9254	High Similarity	NPC182496
0.9254	High Similarity	NPC180905
0.9214	High Similarity	NPC163846
0.9214	High Similarity	NPC225173
0.9203	High Similarity	NPC250755
0.9203	High Similarity	NPC471733
0.9197	High Similarity	NPC168471
0.9197	High Similarity	NPC158472
0.9185	High Similarity	NPC235115
0.9179	High Similarity	NPC175943
0.9167	High Similarity	NPC296158
0.9137	High Similarity	NPC51106
0.9137	High Similarity	NPC478202
0.9137	High Similarity	NPC472006
0.913	High Similarity	NPC158634
0.913	High Similarity	NPC472035
0.913	High Similarity	NPC475730
0.913	High Similarity	NPC478201
0.9124	High Similarity	NPC32360
0.9118	High Similarity	NPC135837
0.9118	High Similarity	NPC149372
0.9118	High Similarity	NPC474849
0.9118	High Similarity	NPC178467
0.9118	High Similarity	NPC474771
0.9118	High Similarity	NPC65837
0.9111	High Similarity	NPC290803
0.9078	High Similarity	NPC237208
0.9077	High Similarity	NPC201728
0.9077	High Similarity	NPC262671
0.9065	High Similarity	NPC474385
0.9065	High Similarity	NPC82913
0.9051	High Similarity	NPC475974
0.9044	High Similarity	NPC118919
0.9044	High Similarity	NPC291454
0.9021	High Similarity	NPC291049
0.9021	High Similarity	NPC233267
0.9014	High Similarity	NPC471734
0.9008	High Similarity	NPC473691
0.9007	High Similarity	NPC83272
0.9007	High Similarity	NPC29577
0.9007	High Similarity	NPC134621
0.9	High Similarity	NPC469542
0.8993	High Similarity	NPC244923
0.8986	High Similarity	NPC268052
0.8986	High Similarity	NPC92655
0.8986	High Similarity	NPC52358
0.8986	High Similarity	NPC471819
0.8971	High Similarity	NPC278375
0.8963	High Similarity	NPC48036
0.8951	High Similarity	NPC221352
0.8951	High Similarity	NPC37139
0.8951	High Similarity	NPC105415
0.8944	High Similarity	NPC107625
0.8944	High Similarity	NPC471735
0.8936	High Similarity	NPC86373
0.8936	High Similarity	NPC66404
0.8936	High Similarity	NPC95123
0.8936	High Similarity	NPC210425
0.8936	High Similarity	NPC277426
0.8936	High Similarity	NPC210966
0.8936	High Similarity	NPC280404
0.8936	High Similarity	NPC478203
0.8936	High Similarity	NPC126882
0.8931	High Similarity	NPC477454
0.8929	High Similarity	NPC469579
0.8929	High Similarity	NPC322112
0.8921	High Similarity	NPC155205
0.8913	High Similarity	NPC177307
0.8913	High Similarity	NPC9121
0.8913	High Similarity	NPC472403
0.8913	High Similarity	NPC221104
0.8905	High Similarity	NPC472599
0.8904	High Similarity	NPC472799
0.8897	High Similarity	NPC474394
0.8897	High Similarity	NPC133856
0.8897	High Similarity	NPC470984
0.8889	High Similarity	NPC476389
0.8881	High Similarity	NPC166583
0.8881	High Similarity	NPC53362
0.8873	High Similarity	NPC257558
0.8873	High Similarity	NPC473692
0.8873	High Similarity	NPC312789
0.8873	High Similarity	NPC472034
0.8873	High Similarity	NPC75694
0.8872	High Similarity	NPC41263
0.8865	High Similarity	NPC84266
0.8864	High Similarity	NPC95309
0.8857	High Similarity	NPC470842
0.8857	High Similarity	NPC90411
0.8849	High Similarity	NPC474655
0.8849	High Similarity	NPC247409
0.8836	High Similarity	NPC273483
0.8832	High Similarity	NPC27407
0.8832	High Similarity	NPC142027
0.8828	High Similarity	NPC150928
0.8828	High Similarity	NPC60413
0.8828	High Similarity	NPC158866
0.8824	High Similarity	NPC470988
0.8819	High Similarity	NPC172329
0.8819	High Similarity	NPC2569
0.8811	High Similarity	NPC260946
0.8811	High Similarity	NPC472033
0.8797	High Similarity	NPC209959
0.8794	High Similarity	NPC94076
0.8794	High Similarity	NPC182255
0.8794	High Similarity	NPC105648
0.8794	High Similarity	NPC49108
0.8786	High Similarity	NPC470986
0.8786	High Similarity	NPC472366
0.8768	High Similarity	NPC156967
0.8768	High Similarity	NPC191976
0.8759	High Similarity	NPC6923
0.8759	High Similarity	NPC282780
0.8759	High Similarity	NPC475645
0.8759	High Similarity	NPC476684
0.8759	High Similarity	NPC166480
0.875	High Similarity	NPC185624
0.875	High Similarity	NPC472036
0.875	High Similarity	NPC8817
0.875	High Similarity	NPC210320
0.875	High Similarity	NPC137296
0.875	High Similarity	NPC27490
0.875	High Similarity	NPC34802
0.8741	High Similarity	NPC21378
0.8741	High Similarity	NPC259942
0.8741	High Similarity	NPC84772
0.8741	High Similarity	NPC34482
0.8741	High Similarity	NPC62219
0.8741	High Similarity	NPC470987
0.8732	High Similarity	NPC354984
0.8731	High Similarity	NPC293453
0.8723	High Similarity	NPC307990
0.8723	High Similarity	NPC220106
0.8723	High Similarity	NPC16455
0.8716	High Similarity	NPC149618
0.8716	High Similarity	NPC89625
0.8707	High Similarity	NPC175978
0.8707	High Similarity	NPC217447
0.8705	High Similarity	NPC261292
0.8705	High Similarity	NPC301915
0.8705	High Similarity	NPC245058
0.8705	High Similarity	NPC470989
0.8705	High Similarity	NPC470985
0.8702	High Similarity	NPC91105
0.8699	High Similarity	NPC307780
0.8699	High Similarity	NPC469619
0.8699	High Similarity	NPC205766
0.8699	High Similarity	NPC179178
0.8699	High Similarity	NPC309979
0.8699	High Similarity	NPC119929
0.8699	High Similarity	NPC469670
0.8699	High Similarity	NPC56204
0.869	High Similarity	NPC471642
0.869	High Similarity	NPC73411
0.869	High Similarity	NPC215711
0.869	High Similarity	NPC240622
0.869	High Similarity	NPC471641
0.869	High Similarity	NPC240253
0.8681	High Similarity	NPC470357

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 NPC194579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	979
0.2-0.3	1667
0.3-0.4	2641
0.4-0.5	1913
0.5-0.6	1118
0.6-0.7	404
0.7-0.8	122
0.8-0.85	17
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8986	High Similarity	NPD970	Clinical (unspecified phase)
0.8873	High Similarity	NPD2532	Approved
0.8873	High Similarity	NPD2534	Approved
0.8873	High Similarity	NPD2533	Approved
0.8649	High Similarity	NPD7819	Suspended
0.8377	Intermediate Similarity	NPD6232	Discontinued
0.8369	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.831	Intermediate Similarity	NPD2935	Discontinued
0.8231	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1240	Approved
0.8163	Intermediate Similarity	NPD7390	Discontinued
0.8156	Intermediate Similarity	NPD230	Phase 1
0.8117	Intermediate Similarity	NPD7075	Discontinued
0.8112	Intermediate Similarity	NPD1510	Phase 2
0.8099	Intermediate Similarity	NPD1607	Approved
0.8099	Intermediate Similarity	NPD6651	Approved
0.8056	Intermediate Similarity	NPD5406	Approved
0.8056	Intermediate Similarity	NPD5405	Approved
0.8056	Intermediate Similarity	NPD5404	Approved
0.8056	Intermediate Similarity	NPD5408	Approved
0.8052	Intermediate Similarity	NPD7768	Phase 2
0.8039	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD9493	Approved
0.8026	Intermediate Similarity	NPD7411	Suspended
0.8025	Intermediate Similarity	NPD5711	Approved
0.8025	Intermediate Similarity	NPD5710	Approved
0.7987	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6959	Discontinued
0.7959	Intermediate Similarity	NPD3750	Approved
0.791	Intermediate Similarity	NPD9545	Approved
0.7891	Intermediate Similarity	NPD2800	Approved
0.7877	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD4380	Phase 2
0.7838	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD943	Approved
0.7823	Intermediate Similarity	NPD1549	Phase 2
0.7817	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6799	Approved
0.7771	Intermediate Similarity	NPD3749	Approved
0.777	Intermediate Similarity	NPD1243	Approved
0.7742	Intermediate Similarity	NPD1934	Approved
0.7742	Intermediate Similarity	NPD6801	Discontinued
0.7727	Intermediate Similarity	NPD6599	Discontinued
0.7714	Intermediate Similarity	NPD1164	Approved
0.7692	Intermediate Similarity	NPD3764	Approved
0.7692	Intermediate Similarity	NPD2801	Approved
0.7687	Intermediate Similarity	NPD1551	Phase 2
0.7687	Intermediate Similarity	NPD2796	Approved
0.7682	Intermediate Similarity	NPD1511	Approved
0.7681	Intermediate Similarity	NPD1201	Approved
0.7669	Intermediate Similarity	NPD5844	Phase 1
0.7664	Intermediate Similarity	NPD4626	Approved
0.7662	Intermediate Similarity	NPD3226	Approved
0.7651	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3817	Phase 2
0.7626	Intermediate Similarity	NPD9269	Phase 2
0.7619	Intermediate Similarity	NPD2799	Discontinued
0.7619	Intermediate Similarity	NPD3748	Approved
0.7595	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3882	Suspended
0.7591	Intermediate Similarity	NPD9268	Approved
0.7589	Intermediate Similarity	NPD1470	Approved
0.7582	Intermediate Similarity	NPD1512	Approved
0.7568	Intermediate Similarity	NPD6100	Approved
0.7568	Intermediate Similarity	NPD6099	Approved
0.7532	Intermediate Similarity	NPD920	Approved
0.7517	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD1465	Phase 2
0.7464	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7286	Phase 2
0.7438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD74	Approved
0.7424	Intermediate Similarity	NPD9266	Approved
0.7417	Intermediate Similarity	NPD2654	Approved
0.741	Intermediate Similarity	NPD7074	Phase 3
0.7403	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1283	Approved
0.7391	Intermediate Similarity	NPD919	Approved
0.7378	Intermediate Similarity	NPD6166	Phase 2
0.7378	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7003	Approved
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7362	Intermediate Similarity	NPD7229	Phase 3
0.7349	Intermediate Similarity	NPD7054	Approved
0.7348	Intermediate Similarity	NPD9267	Approved
0.7348	Intermediate Similarity	NPD9263	Approved
0.7348	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9264	Approved
0.7346	Intermediate Similarity	NPD5494	Approved
0.7343	Intermediate Similarity	NPD1203	Approved
0.7341	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5691	Approved
0.7329	Intermediate Similarity	NPD411	Approved
0.7321	Intermediate Similarity	NPD6559	Discontinued
0.731	Intermediate Similarity	NPD8150	Discontinued
0.731	Intermediate Similarity	NPD6832	Phase 2
0.7308	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7472	Approved
0.7305	Intermediate Similarity	NPD422	Phase 1
0.7297	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD37	Approved
0.729	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3818	Discontinued
0.7254	Intermediate Similarity	NPD1608	Approved
0.7219	Intermediate Similarity	NPD7251	Discontinued
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2313	Discontinued
0.7205	Intermediate Similarity	NPD5402	Approved
0.7197	Intermediate Similarity	NPD5403	Approved
0.7183	Intermediate Similarity	NPD1281	Approved
0.7178	Intermediate Similarity	NPD6234	Discontinued
0.7176	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7808	Phase 3
0.7172	Intermediate Similarity	NPD2798	Approved
0.7172	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2344	Approved
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD6797	Phase 2
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7126	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4060	Phase 1
0.7111	Intermediate Similarity	NPD4750	Phase 3
0.7103	Intermediate Similarity	NPD2797	Approved
0.7101	Intermediate Similarity	NPD9281	Approved
0.7099	Intermediate Similarity	NPD846	Approved
0.7099	Intermediate Similarity	NPD4288	Approved
0.7099	Intermediate Similarity	NPD940	Approved
0.7095	Intermediate Similarity	NPD3268	Approved
0.7095	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7199	Phase 2
0.707	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5401	Approved
0.7067	Intermediate Similarity	NPD5124	Phase 1
0.7067	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6663	Approved
0.7045	Intermediate Similarity	NPD9261	Approved
0.7042	Intermediate Similarity	NPD17	Approved
0.7039	Intermediate Similarity	NPD7033	Discontinued
0.7035	Intermediate Similarity	NPD8312	Approved
0.7035	Intermediate Similarity	NPD8313	Approved
0.7032	Intermediate Similarity	NPD8166	Discontinued
0.7027	Intermediate Similarity	NPD8151	Discontinued
0.7019	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5736	Approved
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.7006	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2979	Phase 3
0.6993	Remote Similarity	NPD4477	Approved
0.6993	Remote Similarity	NPD4476	Approved
0.6988	Remote Similarity	NPD1247	Approved
0.6987	Remote Similarity	NPD6190	Approved
0.6987	Remote Similarity	NPD2309	Approved
0.6982	Remote Similarity	NPD7228	Approved
0.6982	Remote Similarity	NPD7177	Discontinued
0.698	Remote Similarity	NPD1296	Phase 2
0.698	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1651	Approved
0.6966	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4749	Approved
0.6961	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4908	Phase 1
0.6948	Remote Similarity	NPD6005	Phase 3
0.6948	Remote Similarity	NPD6004	Phase 3
0.6948	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6002	Phase 3
0.6943	Remote Similarity	NPD3300	Phase 2
0.694	Remote Similarity	NPD7435	Discontinued
0.6939	Remote Similarity	NPD1019	Discontinued
0.6928	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD2932	Approved
0.6923	Remote Similarity	NPD1778	Approved
0.6923	Remote Similarity	NPD3019	Approved
0.6918	Remote Similarity	NPD6273	Approved
0.6912	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD8320	Phase 1
0.6902	Remote Similarity	NPD8319	Approved
0.6897	Remote Similarity	NPD3972	Approved
0.6892	Remote Similarity	NPD9494	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