NPASS Compound

Structure

NPC470674 OpenBabel07101718182D 25 27 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 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 2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 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 -2.5000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 3 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -1.0000 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 1.7321 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 1 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 -2.5981 -1.5000 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 12 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 24 2 0 0 0 0 19 25 1 0 0 0 0 21 5 1 6 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.21
Volume:	370.718
LogP:	5.573
LogD:	4.762
LogS:	-4.08
# Rotatable Bonds:	3
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	4.03
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.733
MDCK Permeability:	2.1602410924970172e-05
Pgp-inhibitor:	0.062
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.084

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.352
Plasma Protein Binding (PPB):	99.5160140991211%
Volume Distribution (VD):	1.204
Pgp-substrate:	1.376511573791504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.657
CYP1A2-substrate:	0.866
CYP2C19-inhibitor:	0.668
CYP2C19-substrate:	0.637
CYP2C9-inhibitor:	0.533
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.79
CYP2D6-substrate:	0.672
CYP3A4-inhibitor:	0.483
CYP3A4-substrate:	0.487

ADMET: Excretion

Clearance (CL):	2.919
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.286
Drug-inuced Liver Injury (DILI):	0.429
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.535
Maximum Recommended Daily Dose:	0.675
Skin Sensitization:	0.641
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.881
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC470674

Natural Product ID:	NPC470674
*Common Name:**	Empetriferdinan B
IUPAC Name:	1-[(8aR,10aR)-1,3-dihydroxy-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-4-yl]-2-methylbutan-1-one
Synonyms:	Empetriferdinan B
Standard InCHIKey:	OHOUGQQSZUNTBK-DMXAWCJTSA-N
Standard InCHI:	InChI=1S/C21H30O4/c1-6-12(2)18(24)17-15(23)11-14(22)13-10-16-20(3,4)8-7-9-21(16,5)25-19(13)17/h11-12,16,22-23H,6-10H2,1-5H3/t12?,16-,21-/m1/s1
SMILES:	CCC(C)C(=O)C1=C(C=C(C2=C1OC3(CCCC(C3C2)(C)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152498
PubChem CID:	71461986
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO33078	hypericum empetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23030826]

☑ 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	=	16600.0	nM	PMID[493773]

☑ 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 NPC470674 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	397
0.1-0.2	1624
0.2-0.3	3471
0.3-0.4	8481
0.4-0.5	10210
0.5-0.6	4073
0.6-0.7	5941
0.7-0.8	5541
0.8-0.85	2074
0.85-0.9	827
0.9-0.95	48
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC117716
1.0	High Similarity	NPC470673
0.9645	High Similarity	NPC473135
0.9645	High Similarity	NPC470676
0.9645	High Similarity	NPC473132
0.9583	High Similarity	NPC305965
0.9583	High Similarity	NPC473131
0.9583	High Similarity	NPC470675
0.9429	High Similarity	NPC477272
0.9424	High Similarity	NPC470671
0.9424	High Similarity	NPC474504
0.9424	High Similarity	NPC470672
0.9424	High Similarity	NPC474487
0.9371	High Similarity	NPC477955
0.9366	High Similarity	NPC11700
0.9324	High Similarity	NPC4547
0.931	High Similarity	NPC471114
0.9306	High Similarity	NPC300988
0.9306	High Similarity	NPC10990
0.9301	High Similarity	NPC271288
0.9296	High Similarity	NPC144499
0.9291	High Similarity	NPC469818
0.9262	High Similarity	NPC272196
0.9231	High Similarity	NPC219915
0.9231	High Similarity	NPC166138
0.9231	High Similarity	NPC18585
0.9231	High Similarity	NPC106985
0.92	High Similarity	NPC472617
0.9178	High Similarity	NPC10027
0.9178	High Similarity	NPC473016
0.9178	High Similarity	NPC65775
0.9172	High Similarity	NPC308200
0.9167	High Similarity	NPC131568
0.9167	High Similarity	NPC131579
0.9161	High Similarity	NPC310340
0.9155	High Similarity	NPC69769
0.9155	High Similarity	NPC275734
0.9149	High Similarity	NPC470669
0.9149	High Similarity	NPC470668
0.9149	High Similarity	NPC131130
0.9139	High Similarity	NPC472618
0.9122	High Similarity	NPC87708
0.9116	High Similarity	NPC227122
0.9116	High Similarity	NPC150928
0.9116	High Similarity	NPC471115
0.9116	High Similarity	NPC29777
0.911	High Similarity	NPC145467
0.911	High Similarity	NPC39195
0.9103	High Similarity	NPC290133
0.9103	High Similarity	NPC24136
0.9103	High Similarity	NPC187282
0.9103	High Similarity	NPC285630
0.9103	High Similarity	NPC127059
0.9097	High Similarity	NPC81697
0.9097	High Similarity	NPC38219
0.9097	High Similarity	NPC478086
0.9097	High Similarity	NPC223812
0.9097	High Similarity	NPC214166
0.9097	High Similarity	NPC316816
0.9097	High Similarity	NPC77794
0.9097	High Similarity	NPC85162
0.9097	High Similarity	NPC107177
0.9097	High Similarity	NPC278249
0.9097	High Similarity	NPC125894
0.9091	High Similarity	NPC279650
0.9091	High Similarity	NPC64908
0.9091	High Similarity	NPC147688
0.9091	High Similarity	NPC258630
0.9091	High Similarity	NPC17170
0.9091	High Similarity	NPC166689
0.9091	High Similarity	NPC282300
0.9091	High Similarity	NPC96408
0.9091	High Similarity	NPC205006
0.9091	High Similarity	NPC156190
0.9091	High Similarity	NPC156590
0.9091	High Similarity	NPC118840
0.9085	High Similarity	NPC55018
0.9085	High Similarity	NPC96565
0.9085	High Similarity	NPC216978
0.9085	High Similarity	NPC220062
0.9085	High Similarity	NPC301217
0.9085	High Similarity	NPC303633
0.906	High Similarity	NPC95842
0.906	High Similarity	NPC280530
0.906	High Similarity	NPC178964
0.9054	High Similarity	NPC232645
0.9054	High Similarity	NPC474417
0.9054	High Similarity	NPC72958
0.9054	High Similarity	NPC149526
0.9054	High Similarity	NPC478148
0.9048	High Similarity	NPC97028
0.9048	High Similarity	NPC288036
0.9048	High Similarity	NPC97029
0.9048	High Similarity	NPC100985
0.9048	High Similarity	NPC158338
0.9048	High Similarity	NPC473978
0.9048	High Similarity	NPC65589
0.9041	High Similarity	NPC245757
0.9041	High Similarity	NPC304351
0.9041	High Similarity	NPC473077
0.9041	High Similarity	NPC296998
0.9034	High Similarity	NPC209040
0.9034	High Similarity	NPC470890
0.9034	High Similarity	NPC473013
0.9034	High Similarity	NPC206212
0.9034	High Similarity	NPC71184
0.9034	High Similarity	NPC311144
0.9034	High Similarity	NPC326500
0.9034	High Similarity	NPC311741
0.9034	High Similarity	NPC235217
0.9034	High Similarity	NPC234629
0.9034	High Similarity	NPC473015
0.9034	High Similarity	NPC473014
0.9028	High Similarity	NPC62840
0.9028	High Similarity	NPC32739
0.9028	High Similarity	NPC194432
0.9028	High Similarity	NPC223500
0.9028	High Similarity	NPC328164
0.9028	High Similarity	NPC226636
0.9028	High Similarity	NPC296917
0.9028	High Similarity	NPC66515
0.9028	High Similarity	NPC78803
0.9028	High Similarity	NPC217083
0.9028	High Similarity	NPC182852
0.9028	High Similarity	NPC265040
0.9028	High Similarity	NPC228504
0.9028	High Similarity	NPC306829
0.9028	High Similarity	NPC214236
0.9028	High Similarity	NPC202981
0.9028	High Similarity	NPC64915
0.9028	High Similarity	NPC40833
0.9028	High Similarity	NPC125855
0.9028	High Similarity	NPC10937
0.9028	High Similarity	NPC166934
0.9028	High Similarity	NPC324134
0.9028	High Similarity	NPC148757
0.9028	High Similarity	NPC161506
0.9028	High Similarity	NPC59739
0.9028	High Similarity	NPC78
0.9028	High Similarity	NPC166482
0.9028	High Similarity	NPC293852
0.9028	High Similarity	NPC37496
0.9028	High Similarity	NPC227579
0.9028	High Similarity	NPC167624
0.9028	High Similarity	NPC107572
0.9028	High Similarity	NPC1089
0.9028	High Similarity	NPC177354
0.9028	High Similarity	NPC299080
0.9028	High Similarity	NPC220998
0.9028	High Similarity	NPC76338
0.9028	High Similarity	NPC324436
0.9028	High Similarity	NPC11561
0.9028	High Similarity	NPC76372
0.9021	High Similarity	NPC172986
0.9021	High Similarity	NPC159275
0.9021	High Similarity	NPC129853
0.9021	High Similarity	NPC235239
0.9021	High Similarity	NPC241100
0.9021	High Similarity	NPC305355
0.9021	High Similarity	NPC475680
0.9021	High Similarity	NPC270883
0.9021	High Similarity	NPC76445
0.9021	High Similarity	NPC150522
0.9021	High Similarity	NPC284550
0.9021	High Similarity	NPC261227
0.9021	High Similarity	NPC11056
0.902	High Similarity	NPC206605
0.902	High Similarity	NPC473022
0.902	High Similarity	NPC475106
0.9014	High Similarity	NPC201395
0.9013	High Similarity	NPC476280
0.9013	High Similarity	NPC80375
0.9007	High Similarity	NPC156910
0.9007	High Similarity	NPC174999
0.9007	High Similarity	NPC196448
0.9	High Similarity	NPC55662
0.9	High Similarity	NPC166054
0.9	High Similarity	NPC471116
0.8993	High Similarity	NPC217447
0.8986	High Similarity	NPC188403
0.8986	High Similarity	NPC476185
0.8986	High Similarity	NPC472633
0.8986	High Similarity	NPC158866
0.8986	High Similarity	NPC321896
0.898	High Similarity	NPC256672
0.898	High Similarity	NPC186397
0.898	High Similarity	NPC37135
0.898	High Similarity	NPC27221
0.898	High Similarity	NPC296869
0.898	High Similarity	NPC7025
0.8973	High Similarity	NPC111786
0.8973	High Similarity	NPC301276
0.8973	High Similarity	NPC214774
0.8973	High Similarity	NPC154217
0.8973	High Similarity	NPC475052
0.8973	High Similarity	NPC54577
0.8973	High Similarity	NPC176229
0.8973	High Similarity	NPC88964
0.8973	High Similarity	NPC195621
0.8973	High Similarity	NPC470647

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 NPC470674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	950
0.2-0.3	1632
0.3-0.4	2607
0.4-0.5	1975
0.5-0.6	1072
0.6-0.7	396
0.7-0.8	127
0.8-0.85	25
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8904	High Similarity	NPD4378	Clinical (unspecified phase)
0.8819	High Similarity	NPD2800	Approved
0.8776	High Similarity	NPD7410	Clinical (unspecified phase)
0.875	High Similarity	NPD8443	Clinical (unspecified phase)
0.8741	High Similarity	NPD6100	Approved
0.8741	High Similarity	NPD6099	Approved
0.8684	High Similarity	NPD2393	Clinical (unspecified phase)
0.8684	High Similarity	NPD7819	Suspended
0.8681	High Similarity	NPD1552	Clinical (unspecified phase)
0.8681	High Similarity	NPD1550	Clinical (unspecified phase)
0.8621	High Similarity	NPD1549	Phase 2
0.859	High Similarity	NPD6959	Discontinued
0.8531	High Similarity	NPD6651	Approved
0.8493	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD7411	Suspended
0.8414	Intermediate Similarity	NPD1510	Phase 2
0.8397	Intermediate Similarity	NPD7075	Discontinued
0.8392	Intermediate Similarity	NPD1240	Approved
0.8378	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1934	Approved
0.8366	Intermediate Similarity	NPD4380	Phase 2
0.8356	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD1511	Approved
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD3749	Approved
0.8276	Intermediate Similarity	NPD1607	Approved
0.8255	Intermediate Similarity	NPD3750	Approved
0.8224	Intermediate Similarity	NPD1512	Approved
0.8205	Intermediate Similarity	NPD2801	Approved
0.8199	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD2532	Approved
0.8158	Intermediate Similarity	NPD2533	Approved
0.8158	Intermediate Similarity	NPD2534	Approved
0.8141	Intermediate Similarity	NPD6801	Discontinued
0.8129	Intermediate Similarity	NPD6599	Discontinued
0.8101	Intermediate Similarity	NPD7768	Phase 2
0.8063	Intermediate Similarity	NPD5494	Approved
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2799	Discontinued
0.8037	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD3882	Suspended
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD6799	Approved
0.7963	Intermediate Similarity	NPD6232	Discontinued
0.7947	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1243	Approved
0.7939	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3748	Approved
0.7877	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD7390	Discontinued
0.7857	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD3226	Approved
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7815	Intermediate Similarity	NPD2344	Approved
0.7812	Intermediate Similarity	NPD3817	Phase 2
0.7808	Intermediate Similarity	NPD4625	Phase 3
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD4749	Approved
0.7755	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1465	Phase 2
0.7748	Intermediate Similarity	NPD1551	Phase 2
0.774	Intermediate Similarity	NPD4908	Phase 1
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7725	Intermediate Similarity	NPD7054	Approved
0.7707	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD6559	Discontinued
0.7679	Intermediate Similarity	NPD7472	Approved
0.7665	Intermediate Similarity	NPD3818	Discontinued
0.7662	Intermediate Similarity	NPD4628	Phase 3
0.7636	Intermediate Similarity	NPD5711	Approved
0.7636	Intermediate Similarity	NPD5710	Approved
0.7635	Intermediate Similarity	NPD2313	Discontinued
0.7635	Intermediate Similarity	NPD3268	Approved
0.7633	Intermediate Similarity	NPD5953	Discontinued
0.7633	Intermediate Similarity	NPD6797	Phase 2
0.7622	Intermediate Similarity	NPD1610	Phase 2
0.7619	Intermediate Similarity	NPD7286	Phase 2
0.7613	Intermediate Similarity	NPD2309	Approved
0.7603	Intermediate Similarity	NPD2798	Approved
0.7588	Intermediate Similarity	NPD7251	Discontinued
0.758	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7808	Phase 3
0.7534	Intermediate Similarity	NPD1203	Approved
0.7534	Intermediate Similarity	NPD2797	Approved
0.7533	Intermediate Similarity	NPD943	Approved
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7484	Intermediate Similarity	NPD5403	Approved
0.7483	Intermediate Similarity	NPD5124	Phase 1
0.7483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1608	Approved
0.7448	Intermediate Similarity	NPD9717	Approved
0.7442	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7003	Approved
0.7423	Intermediate Similarity	NPD5761	Phase 2
0.7423	Intermediate Similarity	NPD5760	Phase 2
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7391	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3926	Phase 2
0.7379	Intermediate Similarity	NPD1201	Approved
0.7379	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD422	Phase 1
0.7378	Intermediate Similarity	NPD5402	Approved
0.7374	Intermediate Similarity	NPD4361	Phase 2
0.7374	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2654	Approved
0.7358	Intermediate Similarity	NPD5401	Approved
0.7349	Intermediate Similarity	NPD919	Approved
0.7338	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD4308	Phase 3
0.7337	Intermediate Similarity	NPD2403	Approved
0.7329	Intermediate Similarity	NPD3972	Approved
0.7326	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7229	Phase 3
0.7315	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1470	Approved
0.7297	Intermediate Similarity	NPD3267	Approved
0.7297	Intermediate Similarity	NPD3266	Approved
0.7292	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5406	Approved
0.729	Intermediate Similarity	NPD5408	Approved
0.729	Intermediate Similarity	NPD5405	Approved
0.729	Intermediate Similarity	NPD5404	Approved
0.7288	Intermediate Similarity	NPD4287	Approved
0.7285	Intermediate Similarity	NPD3764	Approved
0.7283	Intermediate Similarity	NPD6104	Discontinued
0.7273	Intermediate Similarity	NPD4288	Approved
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6832	Phase 2
0.7262	Intermediate Similarity	NPD1247	Approved
0.7248	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1471	Phase 3
0.7241	Intermediate Similarity	NPD17	Approved
0.723	Intermediate Similarity	NPD6696	Suspended
0.7226	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1548	Phase 1
0.7205	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD8312	Approved
0.72	Intermediate Similarity	NPD8313	Approved
0.7171	Intermediate Similarity	NPD411	Approved
0.7168	Intermediate Similarity	NPD1729	Discontinued
0.716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7124	Intermediate Similarity	NPD8032	Phase 2
0.7118	Intermediate Similarity	NPD3787	Discontinued
0.7114	Intermediate Similarity	NPD3225	Approved
0.7086	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2861	Phase 2
0.7078	Intermediate Similarity	NPD4307	Phase 2
0.7078	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4060	Phase 1
0.7076	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1164	Approved
0.7066	Intermediate Similarity	NPD2296	Approved
0.7059	Intermediate Similarity	NPD1296	Phase 2
0.7049	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD37	Approved
0.7041	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6234	Discontinued
0.7032	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1933	Approved
0.703	Intermediate Similarity	NPD6585	Discontinued
0.7027	Intermediate Similarity	NPD6782	Approved
0.7027	Intermediate Similarity	NPD6780	Approved
0.7027	Intermediate Similarity	NPD6778	Approved
0.7027	Intermediate Similarity	NPD6777	Approved
0.7027	Intermediate Similarity	NPD6779	Approved
0.7027	Intermediate Similarity	NPD6776	Approved
0.7027	Intermediate Similarity	NPD6781	Approved
0.7025	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4966	Approved
0.7024	Intermediate Similarity	NPD4967	Phase 2
0.7024	Intermediate Similarity	NPD4965	Approved
0.7007	Intermediate Similarity	NPD3019	Approved
0.7007	Intermediate Similarity	NPD2932	Approved
0.7	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD1876	Approved
0.6994	Remote Similarity	NPD3446	Phase 1
0.6993	Remote Similarity	NPD7095	Approved
0.6986	Remote Similarity	NPD9545	Approved
0.6984	Remote Similarity	NPD7584	Approved
0.6983	Remote Similarity	NPD8150	Discontinued
0.6981	Remote Similarity	NPD2424	Discontinued

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