NPASS Compound

Structure

CID316960 OpenBabel06191716132D 34 37 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 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 -0.5000 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 5.1962 -2.0000 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 -0.0000 3.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -0.0000 4.0000 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 -1.7321 1.0000 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 1.7321 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 3.4641 -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 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 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 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 18 2 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 25 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 21 29 1 0 0 0 0 22 27 1 0 0 0 0 22 30 2 0 0 0 0 23 34 1 0 0 0 0 24 27 2 0 0 0 0 24 34 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 28 2 0 0 0 0 27 28 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.17
Volume:	479.722
LogP:	4.663
LogD:	3.129
LogS:	-3.875
# Rotatable Bonds:	8
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.391
Synthetic Accessibility Score:	3.541
Fsp3:	0.214
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:	-5.196
MDCK Permeability:	9.181900168186985e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.164
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	100.8488540649414%
Volume Distribution (VD):	0.294
Pgp-substrate:	0.33203327655792236%

ADMET: Metabolism

CYP1A2-inhibitor:	0.209
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.676
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.932
CYP2C9-substrate:	0.989
CYP2D6-inhibitor:	0.774
CYP2D6-substrate:	0.437
CYP3A4-inhibitor:	0.29
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	0.967
Half-life (T1/2):	0.671

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.817
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.335
Rat Oral Acute Toxicity:	0.913
Maximum Recommended Daily Dose:	0.496
Skin Sensitization:	0.34
Carcinogencity:	0.304
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.527

Download Data

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

Natural Product: NPC316960

Natural Product ID:	NPC316960
*Common Name:**	(+/-)-Chartaceone A
IUPAC Name:	(E)-5-(5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-6-yl)-7-phenylhept-6-enoic acid
Synonyms:	(+/-)-Chartaceone A
Standard InCHIKey:	SBOVSSLXUHHHLZ-CCEZHUSRSA-N
Standard InCHI:	InChI=1S/C28H26O6/c29-21-17-24-27(22(30)16-23(34-24)19-10-5-2-6-11-19)28(33)26(21)20(12-7-13-25(31)32)15-14-18-8-3-1-4-9-18/h1-6,8-11,14-15,17,20,23,29,33H,7,12-13,16H2,(H,31,32)/b15-14+
SMILES:	OC(=O)CCCC(c1c(O)cc2c(c1O)C(=O)CC(O2)c1ccccc1)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1940609
PubChem CID:	56834067
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

*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
NPO11348	Cryptocarya chartacea	Species	Lauraceae	Eukaryota	n.a.	trunk bark	n.a.	PMID[22050318]
NPO11348	Cryptocarya chartacea	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[22050318]
NPO11348	Cryptocarya chartacea	Species	Lauraceae	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	2
Others	1

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	GI	=	3.2	%	PMID[490017]
NPT2	Others	Unspecified		IC50	=	14800.0	nM	PMID[490017]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[490017]

☑ 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 NPC316960 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	364
0.1-0.2	1507
0.2-0.3	3443
0.3-0.4	7908
0.4-0.5	10625
0.5-0.6	3668
0.6-0.7	5559
0.7-0.8	5629
0.8-0.85	2410
0.85-0.9	1172
0.9-0.95	397
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC204561
1.0	High Similarity	NPC78835
1.0	High Similarity	NPC309512
1.0	High Similarity	NPC317715
1.0	High Similarity	NPC148945
0.9592	High Similarity	NPC209142
0.9592	High Similarity	NPC312549
0.9592	High Similarity	NPC178484
0.9583	High Similarity	NPC470135
0.9583	High Similarity	NPC39045
0.9583	High Similarity	NPC470136
0.9536	High Similarity	NPC114147
0.9533	High Similarity	NPC324358
0.9533	High Similarity	NPC323627
0.9533	High Similarity	NPC318527
0.9533	High Similarity	NPC322459
0.9517	High Similarity	NPC470132
0.9517	High Similarity	NPC470133
0.9517	High Similarity	NPC470131
0.9517	High Similarity	NPC473078
0.9517	High Similarity	NPC109183
0.9517	High Similarity	NPC470134
0.9474	High Similarity	NPC175513
0.9474	High Similarity	NPC97812
0.9474	High Similarity	NPC114652
0.9463	High Similarity	NPC121568
0.9456	High Similarity	NPC19238
0.9456	High Similarity	NPC104236
0.9456	High Similarity	NPC164205
0.9456	High Similarity	NPC473016
0.9448	High Similarity	NPC271288
0.9388	High Similarity	NPC122894
0.9384	High Similarity	NPC228779
0.9384	High Similarity	NPC25844
0.9379	High Similarity	NPC85162
0.9379	High Similarity	NPC278249
0.9379	High Similarity	NPC81697
0.9379	High Similarity	NPC125894
0.9379	High Similarity	NPC107177
0.9379	High Similarity	NPC223812
0.9379	High Similarity	NPC77794
0.9338	High Similarity	NPC32867
0.9338	High Similarity	NPC69531
0.9324	High Similarity	NPC3642
0.932	High Similarity	NPC308200
0.932	High Similarity	NPC296998
0.932	High Similarity	NPC300988
0.932	High Similarity	NPC473077
0.932	High Similarity	NPC10990
0.9315	High Similarity	NPC131579
0.9315	High Similarity	NPC473014
0.9315	High Similarity	NPC235217
0.9315	High Similarity	NPC473013
0.9315	High Similarity	NPC131568
0.9315	High Similarity	NPC473015
0.931	High Similarity	NPC194432
0.931	High Similarity	NPC227579
0.931	High Similarity	NPC64915
0.931	High Similarity	NPC166482
0.931	High Similarity	NPC107572
0.931	High Similarity	NPC10937
0.931	High Similarity	NPC76372
0.931	High Similarity	NPC223500
0.931	High Similarity	NPC78
0.931	High Similarity	NPC125855
0.931	High Similarity	NPC228504
0.931	High Similarity	NPC32739
0.931	High Similarity	NPC37496
0.931	High Similarity	NPC76338
0.931	High Similarity	NPC167624
0.931	High Similarity	NPC161506
0.931	High Similarity	NPC328164
0.931	High Similarity	NPC148757
0.931	High Similarity	NPC296917
0.931	High Similarity	NPC324436
0.931	High Similarity	NPC66515
0.931	High Similarity	NPC177354
0.931	High Similarity	NPC182852
0.931	High Similarity	NPC40833
0.931	High Similarity	NPC166934
0.931	High Similarity	NPC306829
0.931	High Similarity	NPC220998
0.931	High Similarity	NPC324134
0.931	High Similarity	NPC265040
0.931	High Similarity	NPC1089
0.9276	High Similarity	NPC475184
0.9276	High Similarity	NPC257166
0.9276	High Similarity	NPC1796
0.9272	High Similarity	NPC134171
0.9272	High Similarity	NPC66441
0.9272	High Similarity	NPC300668
0.9272	High Similarity	NPC182555
0.9267	High Similarity	NPC174086
0.9262	High Similarity	NPC474735
0.9262	High Similarity	NPC471115
0.9262	High Similarity	NPC29777
0.9257	High Similarity	NPC39195
0.9257	High Similarity	NPC106328
0.9257	High Similarity	NPC35150
0.9257	High Similarity	NPC145467
0.9252	High Similarity	NPC176229
0.9252	High Similarity	NPC285630
0.9252	High Similarity	NPC54577
0.9252	High Similarity	NPC246948
0.9252	High Similarity	NPC474161
0.9252	High Similarity	NPC67805
0.9252	High Similarity	NPC88964
0.9252	High Similarity	NPC470647
0.9252	High Similarity	NPC477955
0.9252	High Similarity	NPC475052
0.9252	High Similarity	NPC111786
0.9252	High Similarity	NPC127059
0.9252	High Similarity	NPC195621
0.9252	High Similarity	NPC301276
0.9252	High Similarity	NPC472629
0.9252	High Similarity	NPC470322
0.9252	High Similarity	NPC214774
0.9252	High Similarity	NPC267375
0.9252	High Similarity	NPC154217
0.9252	High Similarity	NPC476088
0.9252	High Similarity	NPC312973
0.9252	High Similarity	NPC20488
0.9252	High Similarity	NPC142405
0.9252	High Similarity	NPC83357
0.9247	High Similarity	NPC478086
0.9247	High Similarity	NPC75049
0.9247	High Similarity	NPC221432
0.9247	High Similarity	NPC185276
0.9247	High Similarity	NPC164980
0.9247	High Similarity	NPC149026
0.9247	High Similarity	NPC214166
0.9247	High Similarity	NPC169591
0.9247	High Similarity	NPC175504
0.9247	High Similarity	NPC310130
0.9247	High Similarity	NPC143896
0.9247	High Similarity	NPC257097
0.9247	High Similarity	NPC150408
0.9247	High Similarity	NPC316816
0.9247	High Similarity	NPC39329
0.9247	High Similarity	NPC68104
0.9247	High Similarity	NPC91560
0.9241	High Similarity	NPC166689
0.9241	High Similarity	NPC279650
0.9241	High Similarity	NPC312391
0.9241	High Similarity	NPC110038
0.9241	High Similarity	NPC324386
0.9241	High Similarity	NPC4743
0.9241	High Similarity	NPC17170
0.9241	High Similarity	NPC156190
0.9241	High Similarity	NPC14871
0.9241	High Similarity	NPC213322
0.9241	High Similarity	NPC96408
0.9241	High Similarity	NPC248372
0.9241	High Similarity	NPC258630
0.9236	High Similarity	NPC316480
0.9221	High Similarity	NPC92589
0.9216	High Similarity	NPC295090
0.9216	High Similarity	NPC105584
0.9216	High Similarity	NPC15815
0.9216	High Similarity	NPC51247
0.9216	High Similarity	NPC195167
0.9211	High Similarity	NPC471787
0.9205	High Similarity	NPC244250
0.9205	High Similarity	NPC20907
0.92	High Similarity	NPC290671
0.9195	High Similarity	NPC471114
0.9189	High Similarity	NPC110303
0.9189	High Similarity	NPC283234
0.9189	High Similarity	NPC23728
0.9189	High Similarity	NPC140120
0.9184	High Similarity	NPC209040
0.9184	High Similarity	NPC1886
0.9184	High Similarity	NPC236766
0.9184	High Similarity	NPC311144
0.9184	High Similarity	NPC196137
0.9184	High Similarity	NPC470890
0.9184	High Similarity	NPC87486
0.9184	High Similarity	NPC319752
0.9184	High Similarity	NPC124780
0.9184	High Similarity	NPC197252
0.9178	High Similarity	NPC202981
0.9172	High Similarity	NPC129853
0.9172	High Similarity	NPC188243
0.9172	High Similarity	NPC6407
0.9172	High Similarity	NPC110228
0.9172	High Similarity	NPC76445
0.9172	High Similarity	NPC284550
0.9167	High Similarity	NPC118813
0.9161	High Similarity	NPC310603
0.9156	High Similarity	NPC226462
0.9156	High Similarity	NPC292863
0.9156	High Similarity	NPC42965
0.9156	High Similarity	NPC195136
0.9156	High Similarity	NPC184326
0.9156	High Similarity	NPC98023
0.9145	High Similarity	NPC258474
0.9145	High Similarity	NPC201227
0.9145	High Similarity	NPC37253
0.9145	High Similarity	NPC79375
0.9139	High Similarity	NPC115601

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 NPC316960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	942
0.2-0.3	1521
0.3-0.4	2466
0.4-0.5	1998
0.5-0.6	1205
0.6-0.7	454
0.7-0.8	172
0.8-0.85	49
0.85-0.9	13
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.94	High Similarity	NPD8443	Clinical (unspecified phase)
0.9329	High Similarity	NPD7411	Suspended
0.9097	High Similarity	NPD1550	Clinical (unspecified phase)
0.9097	High Similarity	NPD1552	Clinical (unspecified phase)
0.9045	High Similarity	NPD7852	Clinical (unspecified phase)
0.9034	High Similarity	NPD1549	Phase 2
0.9026	High Similarity	NPD7075	Discontinued
0.8961	High Similarity	NPD7768	Phase 2
0.8954	High Similarity	NPD7819	Suspended
0.8954	High Similarity	NPD7096	Clinical (unspecified phase)
0.8926	High Similarity	NPD7410	Clinical (unspecified phase)
0.8926	High Similarity	NPD4378	Clinical (unspecified phase)
0.8882	High Similarity	NPD4380	Phase 2
0.8831	High Similarity	NPD2393	Clinical (unspecified phase)
0.8782	High Similarity	NPD3749	Approved
0.8734	High Similarity	NPD6959	Discontinued
0.8716	High Similarity	NPD7421	Clinical (unspecified phase)
0.8699	High Similarity	NPD1510	Phase 2
0.8662	High Similarity	NPD4381	Clinical (unspecified phase)
0.8658	High Similarity	NPD3750	Approved
0.8645	High Similarity	NPD6801	Discontinued
0.8639	High Similarity	NPD2796	Approved
0.8599	High Similarity	NPD4868	Clinical (unspecified phase)
0.8526	High Similarity	NPD1934	Approved
0.8487	Intermediate Similarity	NPD6799	Approved
0.8457	Intermediate Similarity	NPD6166	Phase 2
0.8457	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1240	Approved
0.8415	Intermediate Similarity	NPD5844	Phase 1
0.8415	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7473	Discontinued
0.84	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD6599	Discontinued
0.8389	Intermediate Similarity	NPD1551	Phase 2
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD5403	Approved
0.8323	Intermediate Similarity	NPD5494	Approved
0.8322	Intermediate Similarity	NPD3748	Approved
0.8322	Intermediate Similarity	NPD2799	Discontinued
0.8312	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1607	Approved
0.8288	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD4908	Phase 1
0.8247	Intermediate Similarity	NPD1511	Approved
0.8217	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2533	Approved
0.8194	Intermediate Similarity	NPD2532	Approved
0.8194	Intermediate Similarity	NPD2534	Approved
0.8194	Intermediate Similarity	NPD5401	Approved
0.8187	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6559	Discontinued
0.8146	Intermediate Similarity	NPD2935	Discontinued
0.8144	Intermediate Similarity	NPD7074	Phase 3
0.8141	Intermediate Similarity	NPD1512	Approved
0.8125	Intermediate Similarity	NPD2801	Approved
0.8107	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1243	Approved
0.8105	Intermediate Similarity	NPD2800	Approved
0.8095	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5953	Discontinued
0.8089	Intermediate Similarity	NPD920	Approved
0.8084	Intermediate Similarity	NPD7054	Approved
0.8077	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD5402	Approved
0.8052	Intermediate Similarity	NPD4628	Phase 3
0.8041	Intermediate Similarity	NPD2313	Discontinued
0.8036	Intermediate Similarity	NPD7472	Approved
0.8025	Intermediate Similarity	NPD3882	Suspended
0.8024	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD5124	Phase 1
0.8	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD3226	Approved
0.7976	Intermediate Similarity	NPD7286	Phase 2
0.7953	Intermediate Similarity	NPD8312	Approved
0.7953	Intermediate Similarity	NPD8313	Approved
0.7947	Intermediate Similarity	NPD6651	Approved
0.7945	Intermediate Similarity	NPD1203	Approved
0.7941	Intermediate Similarity	NPD7251	Discontinued
0.7935	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3268	Approved
0.7917	Intermediate Similarity	NPD1610	Phase 2
0.7895	Intermediate Similarity	NPD7808	Phase 3
0.7888	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7458	Discontinued
0.7865	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2344	Approved
0.7857	Intermediate Similarity	NPD2346	Discontinued
0.7853	Intermediate Similarity	NPD4360	Phase 2
0.7853	Intermediate Similarity	NPD4363	Phase 3
0.7843	Intermediate Similarity	NPD7033	Discontinued
0.7823	Intermediate Similarity	NPD2797	Approved
0.7821	Intermediate Similarity	NPD7003	Approved
0.7793	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6100	Approved
0.7792	Intermediate Similarity	NPD6099	Approved
0.7792	Intermediate Similarity	NPD5406	Approved
0.7792	Intermediate Similarity	NPD5405	Approved
0.7792	Intermediate Similarity	NPD5408	Approved
0.7792	Intermediate Similarity	NPD5404	Approved
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.7791	Intermediate Similarity	NPD8455	Phase 2
0.7785	Intermediate Similarity	NPD6832	Phase 2
0.7785	Intermediate Similarity	NPD7390	Discontinued
0.7784	Intermediate Similarity	NPD7229	Phase 3
0.774	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4287	Approved
0.7711	Intermediate Similarity	NPD919	Approved
0.7682	Intermediate Similarity	NPD6798	Discontinued
0.7682	Intermediate Similarity	NPD3764	Approved
0.7679	Intermediate Similarity	NPD5711	Approved
0.7679	Intermediate Similarity	NPD5710	Approved
0.7658	Intermediate Similarity	NPD2309	Approved
0.7651	Intermediate Similarity	NPD2798	Approved
0.764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4288	Approved
0.7635	Intermediate Similarity	NPD3225	Approved
0.7628	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1608	Approved
0.7619	Intermediate Similarity	NPD7199	Phase 2
0.7619	Intermediate Similarity	NPD9717	Approved
0.7584	Intermediate Similarity	NPD3266	Approved
0.7584	Intermediate Similarity	NPD3267	Approved
0.7578	Intermediate Similarity	NPD6273	Approved
0.7551	Intermediate Similarity	NPD422	Phase 1
0.7532	Intermediate Similarity	NPD6355	Discontinued
0.7531	Intermediate Similarity	NPD7427	Discontinued
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7514	Intermediate Similarity	NPD4361	Phase 2
0.7514	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7177	Discontinued
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7468	Intermediate Similarity	NPD943	Approved
0.7467	Intermediate Similarity	NPD1164	Approved
0.7455	Intermediate Similarity	NPD5890	Approved
0.7455	Intermediate Similarity	NPD5889	Approved
0.7453	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3926	Phase 2
0.7419	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1933	Approved
0.7416	Intermediate Similarity	NPD8150	Discontinued
0.7415	Intermediate Similarity	NPD17	Approved
0.741	Intermediate Similarity	NPD37	Approved
0.7407	Intermediate Similarity	NPD8151	Discontinued
0.7405	Intermediate Similarity	NPD6002	Phase 3
0.7405	Intermediate Similarity	NPD6005	Phase 3
0.7405	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6004	Phase 3
0.7405	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6233	Phase 2
0.7397	Intermediate Similarity	NPD9545	Approved
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7386	Intermediate Similarity	NPD4625	Phase 3
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD2861	Phase 2
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4060	Phase 1
0.7342	Intermediate Similarity	NPD4477	Approved
0.7342	Intermediate Similarity	NPD4476	Approved
0.7338	Intermediate Similarity	NPD1296	Phase 2
0.733	Intermediate Similarity	NPD7783	Phase 2
0.733	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7435	Discontinued
0.7318	Intermediate Similarity	NPD8434	Phase 2
0.7315	Intermediate Similarity	NPD1201	Approved
0.731	Intermediate Similarity	NPD1247	Approved
0.7308	Intermediate Similarity	NPD230	Phase 1
0.7305	Intermediate Similarity	NPD7577	Discontinued
0.7302	Intermediate Similarity	NPD7584	Approved
0.7299	Intermediate Similarity	NPD7228	Approved
0.7289	Intermediate Similarity	NPD6585	Discontinued
0.7284	Intermediate Similarity	NPD7440	Discontinued
0.7283	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6808	Phase 2
0.726	Intermediate Similarity	NPD9493	Approved
0.7258	Intermediate Similarity	NPD6780	Approved
0.7258	Intermediate Similarity	NPD6781	Approved
0.7258	Intermediate Similarity	NPD6777	Approved
0.7258	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6776	Approved
0.7258	Intermediate Similarity	NPD6778	Approved
0.7258	Intermediate Similarity	NPD6779	Approved
0.7258	Intermediate Similarity	NPD6782	Approved
0.7244	Intermediate Similarity	NPD4307	Phase 2
0.7239	Intermediate Similarity	NPD7213	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