NPASS Compound

Structure

CID187491 OpenBabel06191715562D 29 32 0 0 1 0 0 0 0 0999 V2000 -6.6291 3.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4480 1.3183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5905 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2596 3.9456 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.5933 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 -4.5468 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0413 2.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 2.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 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 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 -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 0.0000 2.0000 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 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 -3.5686 2.9945 0.0000 C 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 -3.4641 -0.0000 0.0000 O 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 -1.0000 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 10 2 0 0 0 0 2 10 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 11 10 1 6 0 0 0 12 19 1 0 0 0 0 12 22 2 0 0 0 0 13 17 1 1 0 0 0 13 23 1 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 26 2 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	403.788
LogP:	5.436
LogD:	2.963
LogS:	-3.69
# Rotatable Bonds:	2
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	3.961
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.904
MDCK Permeability:	1.261425313714426e-05
Pgp-inhibitor:	0.12
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.054
20% Bioavailability (F20%):	0.231
30% Bioavailability (F30%):	0.201

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	95.27850341796875%
Volume Distribution (VD):	0.654
Pgp-substrate:	10.843667984008789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.49
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.158
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.729
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.228
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	5.223
Half-life (T1/2):	0.378

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.419
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.657
Rat Oral Acute Toxicity:	0.718
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.915
Carcinogencity:	0.718
Eye Corrosion:	0.003
Eye Irritation:	0.895
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC187491

Natural Product ID:	NPC187491
*Common Name:**	5-O-Demethylpaxanthonin
IUPAC Name:	2-[(1S,4S)-2,2-dimethyl-4-prop-1-en-2-ylcyclopentyl]-1,3,5,6-tetrahydroxyxanthen-9-one
Synonyms:	5-O-Demethylpaxanthonin
Standard InCHIKey:	LYMUFMGSOHLCHO-WCQYABFASA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-10(2)11-7-13(23(3,4)9-11)17-15(25)8-16-18(21(17)28)19(26)12-5-6-14(24)20(27)22(12)29-16/h5-6,8,11,13,24-25,27-28H,1,7,9H2,2-4H3/t11-,13+/m0/s1
SMILES:	CC(=C)[C@H]1C[C@@H](C(C1)(C)C)c1c(O)cc2c(c1O)c(=O)c1c(o2)c(O)c(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513385
PubChem CID:	15958474
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24930002]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26358281]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[8862040]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	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
Others	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.75	mM	PMID[572687]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.78	mM	PMID[572687]

☑ 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 NPC187491 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	458
0.1-0.2	1802
0.2-0.3	3475
0.3-0.4	9789
0.4-0.5	9019
0.5-0.6	4052
0.6-0.7	5795
0.7-0.8	5513
0.8-0.85	1870
0.85-0.9	798
0.9-0.95	121
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC319200
0.9675	High Similarity	NPC161960
0.9675	High Similarity	NPC187745
0.9675	High Similarity	NPC304008
0.961	High Similarity	NPC115853
0.9548	High Similarity	NPC180011
0.9548	High Similarity	NPC219867
0.949	High Similarity	NPC234644
0.9487	High Similarity	NPC235448
0.9481	High Similarity	NPC49402
0.9481	High Similarity	NPC33051
0.9481	High Similarity	NPC70433
0.9481	High Similarity	NPC227337
0.9481	High Similarity	NPC273462
0.9434	High Similarity	NPC472277
0.9427	High Similarity	NPC188433
0.9419	High Similarity	NPC117992
0.9419	High Similarity	NPC230149
0.9419	High Similarity	NPC168247
0.9419	High Similarity	NPC57674
0.9419	High Similarity	NPC152951
0.9371	High Similarity	NPC205265
0.9371	High Similarity	NPC472281
0.9371	High Similarity	NPC18100
0.9367	High Similarity	NPC57715
0.9367	High Similarity	NPC472275
0.9363	High Similarity	NPC185258
0.9363	High Similarity	NPC172770
0.9299	High Similarity	NPC79053
0.9299	High Similarity	NPC474681
0.9299	High Similarity	NPC299520
0.9299	High Similarity	NPC129684
0.9299	High Similarity	NPC136674
0.9299	High Similarity	NPC218313
0.9295	High Similarity	NPC472280
0.9295	High Similarity	NPC256925
0.9259	High Similarity	NPC288813
0.9255	High Similarity	NPC235610
0.925	High Similarity	NPC306321
0.925	High Similarity	NPC220313
0.925	High Similarity	NPC303460
0.9245	High Similarity	NPC472906
0.9241	High Similarity	NPC204879
0.9236	High Similarity	NPC472455
0.9236	High Similarity	NPC68093
0.9236	High Similarity	NPC5322
0.9236	High Similarity	NPC191146
0.9236	High Similarity	NPC133970
0.9236	High Similarity	NPC138243
0.9236	High Similarity	NPC6633
0.9236	High Similarity	NPC470600
0.9231	High Similarity	NPC469550
0.9187	High Similarity	NPC474150
0.9187	High Similarity	NPC474162
0.9182	High Similarity	NPC471973
0.9182	High Similarity	NPC45146
0.9182	High Similarity	NPC235018
0.9177	High Similarity	NPC36852
0.9177	High Similarity	NPC262286
0.9177	High Similarity	NPC78225
0.9177	High Similarity	NPC291508
0.9172	High Similarity	NPC31018
0.9172	High Similarity	NPC255807
0.9172	High Similarity	NPC234255
0.9172	High Similarity	NPC200246
0.9167	High Similarity	NPC237994
0.9167	High Similarity	NPC472912
0.9167	High Similarity	NPC477231
0.9167	High Similarity	NPC260979
0.9167	High Similarity	NPC257648
0.9161	High Similarity	NPC29231
0.9161	High Similarity	NPC472279
0.9156	High Similarity	NPC272721
0.9156	High Similarity	NPC196277
0.9156	High Similarity	NPC43669
0.913	High Similarity	NPC329669
0.913	High Similarity	NPC124038
0.913	High Similarity	NPC473313
0.913	High Similarity	NPC472278
0.9125	High Similarity	NPC266314
0.9125	High Similarity	NPC32694
0.9125	High Similarity	NPC29876
0.9125	High Similarity	NPC167678
0.9119	High Similarity	NPC197856
0.9119	High Similarity	NPC100123
0.9119	High Similarity	NPC46736
0.9114	High Similarity	NPC35038
0.9114	High Similarity	NPC472907
0.9114	High Similarity	NPC278778
0.9114	High Similarity	NPC291878
0.9114	High Similarity	NPC3980
0.9114	High Similarity	NPC195796
0.9108	High Similarity	NPC472905
0.9103	High Similarity	NPC154345
0.9103	High Similarity	NPC31363
0.9102	High Similarity	NPC120102
0.9091	High Similarity	NPC77378
0.9085	High Similarity	NPC472276
0.9085	High Similarity	NPC131866
0.9074	High Similarity	NPC300053
0.9074	High Similarity	NPC108433
0.9068	High Similarity	NPC78332
0.9068	High Similarity	NPC472448
0.9068	High Similarity	NPC206605
0.9068	High Similarity	NPC470694
0.9068	High Similarity	NPC83922
0.9062	High Similarity	NPC476283
0.9062	High Similarity	NPC80375
0.9062	High Similarity	NPC320359
0.9062	High Similarity	NPC56085
0.9062	High Similarity	NPC476280
0.9062	High Similarity	NPC36217
0.9062	High Similarity	NPC204290
0.9062	High Similarity	NPC476980
0.9062	High Similarity	NPC14353
0.9062	High Similarity	NPC472624
0.9062	High Similarity	NPC228785
0.9062	High Similarity	NPC297212
0.9057	High Similarity	NPC472911
0.9057	High Similarity	NPC27337
0.9057	High Similarity	NPC52889
0.9057	High Similarity	NPC474055
0.9057	High Similarity	NPC472914
0.9057	High Similarity	NPC222814
0.9057	High Similarity	NPC245758
0.9057	High Similarity	NPC181960
0.9057	High Similarity	NPC472963
0.9057	High Similarity	NPC96167
0.9057	High Similarity	NPC469584
0.9057	High Similarity	NPC472913
0.9057	High Similarity	NPC472910
0.9057	High Similarity	NPC472598
0.9051	High Similarity	NPC200761
0.9051	High Similarity	NPC477503
0.9051	High Similarity	NPC113906
0.9051	High Similarity	NPC45849
0.9051	High Similarity	NPC470327
0.9045	High Similarity	NPC471982
0.9045	High Similarity	NPC60972
0.9045	High Similarity	NPC39732
0.9038	High Similarity	NPC88804
0.9038	High Similarity	NPC151473
0.9038	High Similarity	NPC3825
0.9012	High Similarity	NPC189473
0.9012	High Similarity	NPC23298
0.9012	High Similarity	NPC12461
0.9006	High Similarity	NPC259456
0.9006	High Similarity	NPC40491
0.9006	High Similarity	NPC278052
0.9006	High Similarity	NPC134783
0.9006	High Similarity	NPC61010
0.9006	High Similarity	NPC258331
0.9	High Similarity	NPC95936
0.9	High Similarity	NPC55738
0.9	High Similarity	NPC74178
0.9	High Similarity	NPC184755
0.9	High Similarity	NPC250214
0.8994	High Similarity	NPC472626
0.8994	High Similarity	NPC142339
0.8994	High Similarity	NPC472916
0.8994	High Similarity	NPC274730
0.8994	High Similarity	NPC209614
0.8994	High Similarity	NPC470328
0.8994	High Similarity	NPC471985
0.8987	High Similarity	NPC18727
0.8987	High Similarity	NPC213896
0.8987	High Similarity	NPC271779
0.8987	High Similarity	NPC88645
0.8987	High Similarity	NPC167091
0.8987	High Similarity	NPC292214
0.8987	High Similarity	NPC192083
0.8987	High Similarity	NPC206238
0.8987	High Similarity	NPC189130
0.8981	High Similarity	NPC256406
0.8981	High Similarity	NPC251110
0.8974	High Similarity	NPC105512
0.8968	High Similarity	NPC168803
0.8963	High Similarity	NPC476306
0.8957	High Similarity	NPC473286
0.8957	High Similarity	NPC62261
0.8957	High Similarity	NPC472450
0.8957	High Similarity	NPC275780
0.8957	High Similarity	NPC239752
0.8957	High Similarity	NPC326520
0.8951	High Similarity	NPC476247
0.8951	High Similarity	NPC474034
0.8951	High Similarity	NPC25152
0.8951	High Similarity	NPC472635
0.8951	High Similarity	NPC474033
0.8951	High Similarity	NPC81679
0.8951	High Similarity	NPC201800
0.8951	High Similarity	NPC329760
0.8944	High Similarity	NPC287328
0.8944	High Similarity	NPC118256
0.8944	High Similarity	NPC119209
0.8944	High Similarity	NPC328102
0.8944	High Similarity	NPC474960
0.8944	High Similarity	NPC28241
0.8944	High Similarity	NPC282009
0.8944	High Similarity	NPC192686

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 NPC187491 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	936
0.2-0.3	1703
0.3-0.4	2730
0.4-0.5	1944
0.5-0.6	945
0.6-0.7	353
0.7-0.8	109
0.8-0.85	19
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8987	High Similarity	NPD2393	Clinical (unspecified phase)
0.8924	High Similarity	NPD1934	Approved
0.8875	High Similarity	NPD3882	Suspended
0.8868	High Similarity	NPD2801	Approved
0.8712	High Similarity	NPD5494	Approved
0.8654	High Similarity	NPD1511	Approved
0.8544	High Similarity	NPD1512	Approved
0.8512	High Similarity	NPD3818	Discontinued
0.8503	High Similarity	NPD6168	Clinical (unspecified phase)
0.8503	High Similarity	NPD6166	Phase 2
0.8503	High Similarity	NPD6167	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7075	Discontinued
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8304	Intermediate Similarity	NPD7074	Phase 3
0.8303	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7819	Suspended
0.8293	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6232	Discontinued
0.825	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7054	Approved
0.8242	Intermediate Similarity	NPD3817	Phase 2
0.8242	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1549	Phase 2
0.8198	Intermediate Similarity	NPD7472	Approved
0.8182	Intermediate Similarity	NPD1465	Phase 2
0.8165	Intermediate Similarity	NPD2800	Approved
0.8153	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD943	Approved
0.811	Intermediate Similarity	NPD6599	Discontinued
0.8061	Intermediate Similarity	NPD7411	Suspended
0.8057	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6797	Phase 2
0.8036	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD5844	Phase 1
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7975	Intermediate Similarity	NPD2796	Approved
0.7963	Intermediate Similarity	NPD6799	Approved
0.7955	Intermediate Similarity	NPD7808	Phase 3
0.7929	Intermediate Similarity	NPD3749	Approved
0.7898	Intermediate Similarity	NPD1607	Approved
0.7898	Intermediate Similarity	NPD6559	Discontinued
0.7895	Intermediate Similarity	NPD6959	Discontinued
0.7895	Intermediate Similarity	NPD1247	Approved
0.7895	Intermediate Similarity	NPD7199	Phase 2
0.7882	Intermediate Similarity	NPD919	Approved
0.7862	Intermediate Similarity	NPD6100	Approved
0.7862	Intermediate Similarity	NPD6099	Approved
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2799	Discontinued
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3750	Approved
0.7765	Intermediate Similarity	NPD7768	Phase 2
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2344	Approved
0.7701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2533	Approved
0.7697	Intermediate Similarity	NPD2534	Approved
0.7697	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6651	Approved
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD2935	Discontinued
0.7624	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3226	Approved
0.761	Intermediate Similarity	NPD447	Suspended
0.7607	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1243	Approved
0.7602	Intermediate Similarity	NPD5402	Approved
0.7598	Intermediate Similarity	NPD7685	Pre-registration
0.7593	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6234	Discontinued
0.7556	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1613	Approved
0.7547	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD5403	Approved
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3748	Approved
0.7444	Intermediate Similarity	NPD5953	Discontinued
0.7425	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1551	Phase 2
0.7421	Intermediate Similarity	NPD2313	Discontinued
0.7421	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7391	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD8127	Discontinued
0.7384	Intermediate Similarity	NPD37	Approved
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5401	Approved
0.7374	Intermediate Similarity	NPD7228	Approved
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3027	Phase 3
0.7356	Intermediate Similarity	NPD4965	Approved
0.7356	Intermediate Similarity	NPD4966	Approved
0.7356	Intermediate Similarity	NPD4967	Phase 2
0.7342	Intermediate Similarity	NPD9494	Approved
0.7341	Intermediate Similarity	NPD5760	Phase 2
0.7341	Intermediate Similarity	NPD5761	Phase 2
0.7333	Intermediate Similarity	NPD7286	Phase 2
0.7326	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8313	Approved
0.7322	Intermediate Similarity	NPD8312	Approved
0.7321	Intermediate Similarity	NPD7390	Discontinued
0.7312	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7458	Discontinued
0.7308	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4908	Phase 1
0.7278	Intermediate Similarity	NPD2798	Approved
0.7278	Intermediate Similarity	NPD3751	Discontinued
0.725	Intermediate Similarity	NPD4625	Phase 3
0.7247	Intermediate Similarity	NPD5711	Approved
0.7247	Intermediate Similarity	NPD5710	Approved
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6273	Approved
0.7215	Intermediate Similarity	NPD1203	Approved
0.7205	Intermediate Similarity	NPD3268	Approved
0.72	Intermediate Similarity	NPD5977	Approved
0.72	Intermediate Similarity	NPD5978	Approved
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7176	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7028	Phase 2
0.7158	Intermediate Similarity	NPD4360	Phase 2
0.7158	Intermediate Similarity	NPD4363	Phase 3
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7151	Intermediate Similarity	NPD1653	Approved
0.7151	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1608	Approved
0.7125	Intermediate Similarity	NPD2861	Phase 2
0.712	Intermediate Similarity	NPD4361	Phase 2
0.712	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD8150	Discontinued
0.7111	Intermediate Similarity	NPD5242	Approved
0.711	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2797	Approved
0.7107	Intermediate Similarity	NPD1470	Approved
0.7101	Intermediate Similarity	NPD6190	Approved
0.7099	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4749	Approved
0.7083	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7072	Intermediate Similarity	NPD2403	Approved
0.707	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1471	Phase 3
0.7062	Intermediate Similarity	NPD6782	Approved
0.7062	Intermediate Similarity	NPD6781	Approved
0.7062	Intermediate Similarity	NPD6780	Approved
0.7062	Intermediate Similarity	NPD6777	Approved
0.7062	Intermediate Similarity	NPD6776	Approved
0.7062	Intermediate Similarity	NPD6778	Approved
0.7062	Intermediate Similarity	NPD6779	Approved
0.7048	Intermediate Similarity	NPD7033	Discontinued
0.7044	Intermediate Similarity	NPD1876	Approved
0.7041	Intermediate Similarity	NPD7003	Approved
0.7041	Intermediate Similarity	NPD8166	Discontinued
0.7037	Intermediate Similarity	NPD4287	Approved
0.7035	Intermediate Similarity	NPD8151	Discontinued
0.7029	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7025	Intermediate Similarity	NPD9717	Approved
0.7025	Intermediate Similarity	NPD3972	Approved
0.7018	Intermediate Similarity	NPD4357	Discontinued
0.7012	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4060	Phase 1
0.7012	Intermediate Similarity	NPD3620	Phase 2
0.7006	Intermediate Similarity	NPD2296	Approved
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5353	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.6994	Remote Similarity	NPD3764	Approved
0.6983	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD4665	Approved
0.6976	Remote Similarity	NPD4111	Phase 1
0.6975	Remote Similarity	NPD6832	Phase 2
0.6966	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1201	Approved
0.6954	Remote Similarity	NPD7435	Discontinued
0.6952	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8032	Phase 2

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