NPASS Compound

Structure

NPC276565 OpenBabel07101719132D 29 30 0 0 1 0 0 0 0 0999 V2000 -4.0226 -1.2424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5743 -2.9154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0908 -0.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3496 -1.6907 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1248 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3155 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 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 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 -0.8660 1.5000 0.0000 C 0 0 2 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 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 -0.8660 0.5000 0.0000 C 0 0 1 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 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 -1.7321 3.0000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 13 2 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 16 1 0 0 0 0 11 23 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 15 19 1 0 0 0 0 15 24 2 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 6 0 0 0 18 29 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 28 1 0 0 0 0 23 6 1 1 0 0 0 23 28 1 0 0 0 0 27 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.22
Volume:	426.174
LogP:	5.767
LogD:	2.925
LogS:	-3.501
# Rotatable Bonds:	7
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	4.339
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.799
MDCK Permeability:	1.1817899576271884e-05
Pgp-inhibitor:	0.921
Pgp-substrate:	0.829
Human Intestinal Absorption (HIA):	0.176
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	88.4258804321289%
Volume Distribution (VD):	3.839
Pgp-substrate:	9.988025665283203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.257
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.245
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.804
CYP2D6-inhibitor:	0.181
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.154
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	6.175
Half-life (T1/2):	0.229

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.281
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.795
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.766
Carcinogencity:	0.288
Eye Corrosion:	0.003
Eye Irritation:	0.411
Respiratory Toxicity:	0.555

Download Data

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

Natural Product: NPC276565

Natural Product ID:	NPC276565
*Common Name:**	Harrisolanol A
IUPAC Name:	1-[(2R,3R)-3-hydroperoxy-5,7-dihydroxy-2-methyl-6-(3-methylbut-2-enyl)-2-(4-methylpent-3-enyl)-3,4-dihydrochromen-8-yl]ethanone
Synonyms:
Standard InCHIKey:	SPYURBRWMRJZNS-WZONZLPQSA-N
Standard InCHI:	InChI=1S/C23H32O6/c1-13(2)8-7-11-23(6)18(29-27)12-17-20(25)16(10-9-14(3)4)21(26)19(15(5)24)22(17)28-23/h8-9,18,25-27H,7,10-12H2,1-6H3/t18-,23-/m1/s1
SMILES:	CC(=CCC[C@]1(C)[C@@H](Cc2c(c(CC=C(C)C)c(c(C(=O)C)c2O1)O)O)OO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2398519
PubChem CID:	25223416
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[16394547]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23688954]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21362	Harrisonia perforata	Species	Rutaceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	31040.0	nM	PMID[490728]

☑ 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 NPC276565 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	357
0.1-0.2	1407
0.2-0.3	3649
0.3-0.4	8452
0.4-0.5	10556
0.5-0.6	4068
0.6-0.7	6175
0.7-0.8	5456
0.8-0.85	1758
0.85-0.9	722
0.9-0.95	88
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC18886
0.9574	High Similarity	NPC91902
0.9496	High Similarity	NPC74397
0.9437	High Similarity	NPC47388
0.9437	High Similarity	NPC473133
0.9437	High Similarity	NPC470670
0.931	High Similarity	NPC471677
0.9301	High Similarity	NPC85773
0.9291	High Similarity	NPC112829
0.9241	High Similarity	NPC476509
0.9241	High Similarity	NPC180351
0.9236	High Similarity	NPC10097
0.9231	High Similarity	NPC474302
0.9225	High Similarity	NPC470553
0.9225	High Similarity	NPC33653
0.9225	High Similarity	NPC184738
0.9225	High Similarity	NPC112749
0.9225	High Similarity	NPC307895
0.9203	High Similarity	NPC101752
0.9178	High Similarity	NPC474021
0.9178	High Similarity	NPC474023
0.9178	High Similarity	NPC244577
0.9178	High Similarity	NPC471676
0.9178	High Similarity	NPC472636
0.9178	High Similarity	NPC472420
0.9178	High Similarity	NPC263384
0.9178	High Similarity	NPC472422
0.9172	High Similarity	NPC307052
0.9172	High Similarity	NPC139966
0.9172	High Similarity	NPC472628
0.9167	High Similarity	NPC202494
0.9161	High Similarity	NPC133060
0.9161	High Similarity	NPC118059
0.9161	High Similarity	NPC288910
0.9161	High Similarity	NPC470890
0.9161	High Similarity	NPC470554
0.9155	High Similarity	NPC470556
0.9155	High Similarity	NPC294432
0.9149	High Similarity	NPC471587
0.9149	High Similarity	NPC477272
0.9143	High Similarity	NPC474487
0.9143	High Similarity	NPC470671
0.9143	High Similarity	NPC470672
0.9143	High Similarity	NPC474504
0.9143	High Similarity	NPC131130
0.9122	High Similarity	NPC477958
0.9116	High Similarity	NPC477957
0.9116	High Similarity	NPC473996
0.9116	High Similarity	NPC475790
0.9116	High Similarity	NPC256141
0.9116	High Similarity	NPC138288
0.911	High Similarity	NPC321387
0.911	High Similarity	NPC105136
0.911	High Similarity	NPC472421
0.911	High Similarity	NPC470908
0.911	High Similarity	NPC327059
0.9103	High Similarity	NPC472345
0.9097	High Similarity	NPC472629
0.9097	High Similarity	NPC470910
0.9097	High Similarity	NPC187282
0.9097	High Similarity	NPC290133
0.9097	High Similarity	NPC285630
0.9097	High Similarity	NPC24136
0.9097	High Similarity	NPC127059
0.9091	High Similarity	NPC478086
0.9091	High Similarity	NPC96216
0.9091	High Similarity	NPC470909
0.9091	High Similarity	NPC185276
0.9091	High Similarity	NPC474939
0.9091	High Similarity	NPC316816
0.9091	High Similarity	NPC214166
0.9085	High Similarity	NPC171870
0.9085	High Similarity	NPC156190
0.9085	High Similarity	NPC248372
0.9085	High Similarity	NPC279650
0.9085	High Similarity	NPC17170
0.9085	High Similarity	NPC166689
0.9085	High Similarity	NPC110038
0.9085	High Similarity	NPC96408
0.9085	High Similarity	NPC258630
0.9078	High Similarity	NPC139554
0.9078	High Similarity	NPC23257
0.906	High Similarity	NPC215917
0.906	High Similarity	NPC20530
0.906	High Similarity	NPC10754
0.9054	High Similarity	NPC236756
0.9054	High Similarity	NPC100134
0.9054	High Similarity	NPC311579
0.9054	High Similarity	NPC7989
0.9054	High Similarity	NPC223701
0.9054	High Similarity	NPC248793
0.9054	High Similarity	NPC180301
0.9054	High Similarity	NPC472583
0.9054	High Similarity	NPC293286
0.9054	High Similarity	NPC469405
0.9054	High Similarity	NPC209760
0.9048	High Similarity	NPC262038
0.9048	High Similarity	NPC474744
0.9048	High Similarity	NPC278476
0.9048	High Similarity	NPC254412
0.9048	High Similarity	NPC319910
0.9048	High Similarity	NPC472580
0.9048	High Similarity	NPC262039
0.9048	High Similarity	NPC474772
0.9048	High Similarity	NPC472423
0.9048	High Similarity	NPC471675
0.9034	High Similarity	NPC283234
0.9034	High Similarity	NPC296998
0.9034	High Similarity	NPC285748
0.9034	High Similarity	NPC473077
0.9034	High Similarity	NPC472627
0.9028	High Similarity	NPC297788
0.9028	High Similarity	NPC235217
0.9028	High Similarity	NPC131568
0.9028	High Similarity	NPC224714
0.9028	High Similarity	NPC473014
0.9028	High Similarity	NPC209040
0.9028	High Similarity	NPC87486
0.9028	High Similarity	NPC131579
0.9028	High Similarity	NPC236766
0.9028	High Similarity	NPC197252
0.9028	High Similarity	NPC124780
0.9021	High Similarity	NPC324436
0.9021	High Similarity	NPC32739
0.9021	High Similarity	NPC194432
0.9021	High Similarity	NPC223500
0.9021	High Similarity	NPC472344
0.9021	High Similarity	NPC66515
0.9021	High Similarity	NPC177354
0.9021	High Similarity	NPC182852
0.9021	High Similarity	NPC306829
0.9021	High Similarity	NPC228504
0.9021	High Similarity	NPC328164
0.9021	High Similarity	NPC64915
0.9021	High Similarity	NPC40833
0.9021	High Similarity	NPC125855
0.9021	High Similarity	NPC166934
0.9021	High Similarity	NPC296917
0.9021	High Similarity	NPC265040
0.9021	High Similarity	NPC166482
0.9021	High Similarity	NPC324134
0.9021	High Similarity	NPC161506
0.9021	High Similarity	NPC78
0.9021	High Similarity	NPC148757
0.9021	High Similarity	NPC37496
0.9021	High Similarity	NPC76372
0.9021	High Similarity	NPC167624
0.9021	High Similarity	NPC107572
0.9021	High Similarity	NPC1089
0.9021	High Similarity	NPC10937
0.9021	High Similarity	NPC220998
0.9021	High Similarity	NPC76338
0.9021	High Similarity	NPC227579
0.9	High Similarity	NPC156910
0.9	High Similarity	NPC470398
0.9	High Similarity	NPC174999
0.8993	High Similarity	NPC48579
0.8993	High Similarity	NPC259710
0.8993	High Similarity	NPC304207
0.8993	High Similarity	NPC207809
0.8993	High Similarity	NPC217706
0.8993	High Similarity	NPC226025
0.8986	High Similarity	NPC31627
0.8986	High Similarity	NPC171651
0.8986	High Similarity	NPC56232
0.8986	High Similarity	NPC150123
0.8986	High Similarity	NPC35567
0.8986	High Similarity	NPC216035
0.8986	High Similarity	NPC217149
0.8986	High Similarity	NPC327269
0.8986	High Similarity	NPC244583
0.8986	High Similarity	NPC10807
0.8986	High Similarity	NPC476238
0.8986	High Similarity	NPC161881
0.8986	High Similarity	NPC243171
0.8986	High Similarity	NPC210597
0.898	High Similarity	NPC472633
0.898	High Similarity	NPC38775
0.8973	High Similarity	NPC160821
0.8973	High Similarity	NPC132592
0.8973	High Similarity	NPC145467
0.8966	High Similarity	NPC246948
0.8966	High Similarity	NPC267375
0.8966	High Similarity	NPC176229
0.8966	High Similarity	NPC20488
0.8966	High Similarity	NPC67805
0.8966	High Similarity	NPC142405
0.8966	High Similarity	NPC316769
0.8966	High Similarity	NPC111786
0.8966	High Similarity	NPC301276
0.8966	High Similarity	NPC214774
0.8966	High Similarity	NPC83357
0.8966	High Similarity	NPC82534
0.8966	High Similarity	NPC475052
0.8966	High Similarity	NPC54577
0.8966	High Similarity	NPC312973
0.8966	High Similarity	NPC88964
0.8966	High Similarity	NPC470647
0.8966	High Similarity	NPC195621
0.8958	High Similarity	NPC150408

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 NPC276565 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	965
0.2-0.3	1931
0.3-0.4	2621
0.4-0.5	1814
0.5-0.6	1001
0.6-0.7	362
0.7-0.8	111
0.8-0.85	19
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD2393	Clinical (unspecified phase)
0.8767	High Similarity	NPD4378	Clinical (unspecified phase)
0.875	High Similarity	NPD7075	Discontinued
0.8725	High Similarity	NPD4380	Phase 2
0.8681	High Similarity	NPD2800	Approved
0.8675	High Similarity	NPD7096	Clinical (unspecified phase)
0.8671	High Similarity	NPD1550	Clinical (unspecified phase)
0.8671	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD8443	Clinical (unspecified phase)
0.8611	High Similarity	NPD1549	Phase 2
0.8609	High Similarity	NPD1934	Approved
0.8521	High Similarity	NPD6651	Approved
0.8514	High Similarity	NPD7410	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD2532	Approved
0.8389	Intermediate Similarity	NPD2534	Approved
0.8389	Intermediate Similarity	NPD2533	Approved
0.8387	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD2796	Approved
0.8312	Intermediate Similarity	NPD7819	Suspended
0.8301	Intermediate Similarity	NPD7411	Suspended
0.8276	Intermediate Similarity	NPD1510	Phase 2
0.8252	Intermediate Similarity	NPD1240	Approved
0.8247	Intermediate Similarity	NPD6801	Discontinued
0.8228	Intermediate Similarity	NPD6959	Discontinued
0.82	Intermediate Similarity	NPD6799	Approved
0.8194	Intermediate Similarity	NPD2801	Approved
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8138	Intermediate Similarity	NPD1607	Approved
0.8098	Intermediate Similarity	NPD7074	Phase 3
0.8089	Intermediate Similarity	NPD3882	Suspended
0.8079	Intermediate Similarity	NPD1511	Approved
0.805	Intermediate Similarity	NPD5494	Approved
0.8037	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD7472	Approved
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7768	Phase 2
0.7974	Intermediate Similarity	NPD1512	Approved
0.7963	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3817	Phase 2
0.7892	Intermediate Similarity	NPD7251	Discontinued
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7866	Intermediate Similarity	NPD3818	Discontinued
0.7862	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7808	Phase 3
0.784	Intermediate Similarity	NPD5711	Approved
0.784	Intermediate Similarity	NPD5710	Approved
0.7831	Intermediate Similarity	NPD6797	Phase 2
0.7823	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD5124	Phase 1
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1243	Approved
0.7806	Intermediate Similarity	NPD920	Approved
0.7805	Intermediate Similarity	NPD7473	Discontinued
0.7733	Intermediate Similarity	NPD6099	Approved
0.7733	Intermediate Similarity	NPD6100	Approved
0.7733	Intermediate Similarity	NPD2935	Discontinued
0.7733	Intermediate Similarity	NPD1551	Phase 2
0.773	Intermediate Similarity	NPD6232	Discontinued
0.7711	Intermediate Similarity	NPD7286	Phase 2
0.7711	Intermediate Similarity	NPD5844	Phase 1
0.7702	Intermediate Similarity	NPD3749	Approved
0.7692	Intermediate Similarity	NPD5403	Approved
0.7677	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD3750	Approved
0.7647	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5953	Discontinued
0.7578	Intermediate Similarity	NPD5402	Approved
0.7564	Intermediate Similarity	NPD5401	Approved
0.7561	Intermediate Similarity	NPD1247	Approved
0.755	Intermediate Similarity	NPD2799	Discontinued
0.7546	Intermediate Similarity	NPD919	Approved
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2424	Discontinued
0.7515	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2344	Approved
0.7401	Intermediate Similarity	NPD4360	Phase 2
0.7401	Intermediate Similarity	NPD4363	Phase 3
0.7391	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6832	Phase 2
0.7365	Intermediate Similarity	NPD4908	Phase 1
0.7361	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2654	Approved
0.7351	Intermediate Similarity	NPD230	Phase 1
0.7338	Intermediate Similarity	NPD2346	Discontinued
0.7337	Intermediate Similarity	NPD7584	Approved
0.7321	Intermediate Similarity	NPD2403	Approved
0.732	Intermediate Similarity	NPD7033	Discontinued
0.732	Intermediate Similarity	NPD3748	Approved
0.732	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD9717	Approved
0.7301	Intermediate Similarity	NPD1465	Phase 2
0.7285	Intermediate Similarity	NPD1613	Approved
0.7285	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD943	Approved
0.7279	Intermediate Similarity	NPD1203	Approved
0.7278	Intermediate Similarity	NPD7390	Discontinued
0.7267	Intermediate Similarity	NPD3226	Approved
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3926	Phase 2
0.7261	Intermediate Similarity	NPD2309	Approved
0.7241	Intermediate Similarity	NPD422	Phase 1
0.7241	Intermediate Similarity	NPD1610	Phase 2
0.7237	Intermediate Similarity	NPD447	Suspended
0.7198	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8313	Approved
0.7184	Intermediate Similarity	NPD8312	Approved
0.7181	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6104	Discontinued
0.716	Intermediate Similarity	NPD7458	Discontinued
0.7152	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD4749	Approved
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7133	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD6002	Phase 3
0.7115	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6004	Phase 3
0.7115	Intermediate Similarity	NPD6005	Phase 3
0.7115	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7091	Intermediate Similarity	NPD8455	Phase 2
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7086	Intermediate Similarity	NPD3027	Phase 3
0.7083	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD9545	Approved
0.7072	Intermediate Similarity	NPD4361	Phase 2
0.7072	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8434	Phase 2
0.7048	Intermediate Similarity	NPD5353	Approved
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD3268	Approved
0.7037	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7097	Phase 1
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1933	Approved
0.7013	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6778	Approved
0.7011	Intermediate Similarity	NPD6782	Approved
0.7011	Intermediate Similarity	NPD6780	Approved
0.7011	Intermediate Similarity	NPD3823	Discontinued
0.7011	Intermediate Similarity	NPD6777	Approved
0.7011	Intermediate Similarity	NPD6776	Approved
0.7011	Intermediate Similarity	NPD6779	Approved
0.7011	Intermediate Similarity	NPD6781	Approved
0.7006	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD1019	Discontinued
0.7	Intermediate Similarity	NPD2798	Approved
0.6989	Remote Similarity	NPD7698	Approved
0.6989	Remote Similarity	NPD7696	Phase 3
0.6989	Remote Similarity	NPD7697	Approved
0.6989	Remote Similarity	NPD7435	Discontinued
0.6988	Remote Similarity	NPD5761	Phase 2
0.6988	Remote Similarity	NPD5760	Phase 2
0.6987	Remote Similarity	NPD4308	Phase 3
0.6987	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8151	Discontinued
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5049	Phase 3
0.6972	Remote Similarity	NPD1241	Discontinued
0.6966	Remote Similarity	NPD8150	Discontinued
0.6952	Remote Similarity	NPD7871	Phase 2
0.6952	Remote Similarity	NPD7870	Phase 2
0.6951	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD9493	Approved
0.6937	Remote Similarity	NPD3887	Approved
0.6936	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2797	Approved
0.6931	Remote Similarity	NPD7585	Approved
0.6928	Remote Similarity	NPD6844	Discontinued
0.6928	Remote Similarity	NPD37	Approved
0.6928	Remote Similarity	NPD1296	Phase 2
0.6928	Remote Similarity	NPD411	Approved
0.6923	Remote Similarity	NPD6234	Discontinued
0.6923	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4662	Approved
0.6914	Remote Similarity	NPD4661	Approved
0.6911	Remote Similarity	NPD7783	Phase 2
0.6911	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4967	Phase 2
0.6905	Remote Similarity	NPD4965	Approved
0.6905	Remote Similarity	NPD4966	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