NPASS Compound

Structure

CID159387 OpenBabel06191715532D 33 35 0 0 1 0 0 0 0 0999 V2000 -4.0121 2.2142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3179 2.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3192 -4.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4531 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5871 -4.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1852 -3.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3192 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7211 -3.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8532 0.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1100 -1.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0611 1.9052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4531 -3.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1852 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 -1.9563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5352 -3.2653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7211 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 -1.6473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1230 -2.4563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8532 -0.9271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0512 -2.4563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8443 -4.2164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5871 -2.4563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -1.9563 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 -2.8551 -2.4563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 -0.3601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 6 1 0 0 0 0 3 15 2 0 0 0 0 4 7 2 0 0 0 0 4 15 1 0 0 0 0 5 8 2 0 0 0 0 5 15 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 25 1 0 0 0 0 12 16 2 0 0 0 0 12 31 1 0 0 0 0 13 24 1 0 0 0 0 13 32 1 0 0 0 0 16 18 1 0 0 0 0 17 26 1 0 0 0 0 18 10 1 1 0 0 0 18 22 1 0 0 0 0 19 24 1 6 0 0 0 19 27 1 0 0 0 0 20 28 2 0 0 0 0 20 32 1 0 0 0 0 21 29 2 0 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 1 0 0 0 23 31 1 0 0 0 0 23 33 1 6 0 0 0 24 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.19
Volume:	458.648
LogP:	2.536
LogD:	1.855
LogS:	-3.58
# Rotatable Bonds:	10
TPSA:	142.75
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	4.485
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.12
MDCK Permeability:	1.889019949885551e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.102
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.21
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.861
Plasma Protein Binding (PPB):	65.12017059326172%
Volume Distribution (VD):	0.737
Pgp-substrate:	26.527694702148438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.406
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.458
CYP2C9-substrate:	0.192
CYP2D6-inhibitor:	0.179
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.512
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	5.986
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.46
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.288
AMES Toxicity:	0.934
Rat Oral Acute Toxicity:	0.901
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.938
Carcinogencity:	0.873
Eye Corrosion:	0.003
Eye Irritation:	0.039
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC159387

Natural Product ID:	NPC159387
*Common Name:**	Luzonoid D
IUPAC Name:	[(1S,4aS,6S,7R,7aS)-6,7-dihydroxy-4-(hydroxymethyl)-7-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate
Synonyms:	Luzonoid D
Standard InCHIKey:	QDYVLLOYMJYQAA-BPJBXTEKSA-N
Standard InCHI:	InChI=1S/C24H30O9/c1-14(2)9-21(29)33-23-22-18(16(11-25)12-31-23)10-19(27)24(22,30)13-32-20(28)8-5-15-3-6-17(26)7-4-15/h3-8,12,14,18-19,22-23,25-27,30H,9-11,13H2,1-2H3/b8-5-/t18-,19+,22-,23+,24-/m1/s1
SMILES:	OCC1=CO[C@H]([C@H]2[C@@H]1C[C@@H]([C@]2(O)COC(=O)/C=Cc1ccc(cc1)O)O)OC(=O)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485662
PubChem CID:	11155452
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568771]
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15635247]
NPO7642	Cleome gynandra	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7642	Cleome gynandra	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7642	Cleome gynandra	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6607	Apopellia endiviifolia	Species	Pelliaceae	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	=	4560.0	nM	PMID[468112]

☑ 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 NPC159387 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	288
0.1-0.2	1055
0.2-0.3	2650
0.3-0.4	5968
0.4-0.5	10574
0.5-0.6	9807
0.6-0.7	10385
0.7-0.8	1824
0.8-0.85	106
0.85-0.9	22
0.9-0.95	6
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC137501
1.0	High Similarity	NPC7518
1.0	High Similarity	NPC154262
0.9852	High Similarity	NPC186296
0.9779	High Similarity	NPC251062
0.9779	High Similarity	NPC184464
0.9412	High Similarity	NPC49597
0.9296	High Similarity	NPC96599
0.9275	High Similarity	NPC46644
0.9231	High Similarity	NPC240592
0.9231	High Similarity	NPC117346
0.9214	High Similarity	NPC202391
0.9214	High Similarity	NPC296659
0.9167	High Similarity	NPC289021
0.9167	High Similarity	NPC158546
0.9007	High Similarity	NPC88754
0.9007	High Similarity	NPC302286
0.9007	High Similarity	NPC237872
0.9007	High Similarity	NPC263397
0.9007	High Similarity	NPC116104
0.8986	High Similarity	NPC475378
0.8944	High Similarity	NPC478240
0.8919	High Similarity	NPC475484
0.8904	High Similarity	NPC475379
0.8897	High Similarity	NPC478236
0.8897	High Similarity	NPC478234
0.8897	High Similarity	NPC254819
0.8889	High Similarity	NPC18789
0.8857	High Similarity	NPC220936
0.8857	High Similarity	NPC31745
0.8844	High Similarity	NPC194705
0.8819	High Similarity	NPC37838
0.8784	High Similarity	NPC229354
0.8716	High Similarity	NPC478235
0.8707	High Similarity	NPC147224
0.8705	High Similarity	NPC169398
0.869	High Similarity	NPC475539
0.869	High Similarity	NPC473147
0.869	High Similarity	NPC474268
0.869	High Similarity	NPC119773
0.869	High Similarity	NPC143246
0.8681	High Similarity	NPC194938
0.8658	High Similarity	NPC89693
0.8658	High Similarity	NPC478241
0.8658	High Similarity	NPC229548
0.8649	High Similarity	NPC269914
0.8649	High Similarity	NPC478249
0.8639	High Similarity	NPC161955
0.8623	High Similarity	NPC475824
0.8621	High Similarity	NPC475528
0.8618	High Similarity	NPC179914
0.8611	High Similarity	NPC293154
0.8609	High Similarity	NPC478248
0.86	High Similarity	NPC478232
0.8582	High Similarity	NPC472132
0.8581	High Similarity	NPC35097
0.8571	High Similarity	NPC308178
0.8553	High Similarity	NPC329997
0.8552	High Similarity	NPC473281
0.8552	High Similarity	NPC77922
0.8552	High Similarity	NPC63304
0.8529	High Similarity	NPC276047
0.8529	High Similarity	NPC267733
0.8521	High Similarity	NPC469364
0.8521	High Similarity	NPC65262
0.8521	High Similarity	NPC101686
0.8516	High Similarity	NPC109990
0.8507	High Similarity	NPC52097
0.85	High Similarity	NPC470143
0.85	High Similarity	NPC322503
0.8493	Intermediate Similarity	NPC210330
0.8489	Intermediate Similarity	NPC281798
0.8489	Intermediate Similarity	NPC478255
0.8483	Intermediate Similarity	NPC475213
0.8483	Intermediate Similarity	NPC152796
0.8467	Intermediate Similarity	NPC35288
0.8467	Intermediate Similarity	NPC471882
0.8467	Intermediate Similarity	NPC106677
0.8467	Intermediate Similarity	NPC156692
0.8467	Intermediate Similarity	NPC173150
0.8467	Intermediate Similarity	NPC288416
0.8467	Intermediate Similarity	NPC45224
0.8467	Intermediate Similarity	NPC471881
0.8452	Intermediate Similarity	NPC145847
0.8446	Intermediate Similarity	NPC189631
0.8446	Intermediate Similarity	NPC120728
0.8442	Intermediate Similarity	NPC138993
0.8435	Intermediate Similarity	NPC320734
0.8433	Intermediate Similarity	NPC11724
0.8414	Intermediate Similarity	NPC296643
0.8411	Intermediate Similarity	NPC257847
0.84	Intermediate Similarity	NPC474620
0.8394	Intermediate Similarity	NPC61181
0.8394	Intermediate Similarity	NPC471157
0.8394	Intermediate Similarity	NPC252114
0.8382	Intermediate Similarity	NPC145287
0.8378	Intermediate Similarity	NPC473149
0.8369	Intermediate Similarity	NPC254398
0.8358	Intermediate Similarity	NPC476872
0.8357	Intermediate Similarity	NPC46137
0.8357	Intermediate Similarity	NPC235294
0.8345	Intermediate Similarity	NPC253595
0.8333	Intermediate Similarity	NPC103533
0.8333	Intermediate Similarity	NPC69367
0.8333	Intermediate Similarity	NPC175333
0.8333	Intermediate Similarity	NPC476011
0.8323	Intermediate Similarity	NPC130489
0.8323	Intermediate Similarity	NPC478265
0.8323	Intermediate Similarity	NPC208676
0.8321	Intermediate Similarity	NPC126991
0.8321	Intermediate Similarity	NPC83218
0.8311	Intermediate Similarity	NPC212808
0.8302	Intermediate Similarity	NPC21956
0.8298	Intermediate Similarity	NPC473924
0.8291	Intermediate Similarity	NPC130730
0.8291	Intermediate Similarity	NPC301910
0.8289	Intermediate Similarity	NPC469699
0.8278	Intermediate Similarity	NPC77310
0.8273	Intermediate Similarity	NPC225307
0.8231	Intermediate Similarity	NPC204644
0.8227	Intermediate Similarity	NPC138777
0.8227	Intermediate Similarity	NPC219677
0.8227	Intermediate Similarity	NPC225384
0.8227	Intermediate Similarity	NPC246869
0.8224	Intermediate Similarity	NPC203664
0.8217	Intermediate Similarity	NPC206815
0.8214	Intermediate Similarity	NPC469549
0.8214	Intermediate Similarity	NPC477294
0.8214	Intermediate Similarity	NPC477293
0.8214	Intermediate Similarity	NPC229784
0.8207	Intermediate Similarity	NPC328273
0.8207	Intermediate Similarity	NPC321184
0.8207	Intermediate Similarity	NPC171134
0.8207	Intermediate Similarity	NPC321638
0.8207	Intermediate Similarity	NPC220942
0.8205	Intermediate Similarity	NPC474936
0.8205	Intermediate Similarity	NPC269668
0.8194	Intermediate Similarity	NPC470572
0.8194	Intermediate Similarity	NPC471345
0.8194	Intermediate Similarity	NPC187205
0.8188	Intermediate Similarity	NPC474234
0.8182	Intermediate Similarity	NPC886
0.8182	Intermediate Similarity	NPC34293
0.8182	Intermediate Similarity	NPC471883
0.8182	Intermediate Similarity	NPC287597
0.8169	Intermediate Similarity	NPC473285
0.8143	Intermediate Similarity	NPC232880
0.8133	Intermediate Similarity	NPC97240
0.8125	Intermediate Similarity	NPC263829
0.8125	Intermediate Similarity	NPC476870
0.8125	Intermediate Similarity	NPC208818
0.8112	Intermediate Similarity	NPC114116
0.8108	Intermediate Similarity	NPC478250
0.8088	Intermediate Similarity	NPC476445
0.8088	Intermediate Similarity	NPC476448
0.8088	Intermediate Similarity	NPC469548
0.8085	Intermediate Similarity	NPC295970
0.8082	Intermediate Similarity	NPC81515
0.8082	Intermediate Similarity	NPC197316
0.8082	Intermediate Similarity	NPC226005
0.8082	Intermediate Similarity	NPC476383
0.8082	Intermediate Similarity	NPC89105
0.8082	Intermediate Similarity	NPC64141
0.8082	Intermediate Similarity	NPC472350
0.8082	Intermediate Similarity	NPC68092
0.8079	Intermediate Similarity	NPC23677
0.8079	Intermediate Similarity	NPC169510
0.8077	Intermediate Similarity	NPC475663
0.8077	Intermediate Similarity	NPC286919
0.8071	Intermediate Similarity	NPC476873
0.8069	Intermediate Similarity	NPC471872
0.8069	Intermediate Similarity	NPC154485
0.8069	Intermediate Similarity	NPC157554
0.8069	Intermediate Similarity	NPC27721
0.8054	Intermediate Similarity	NPC96447
0.8054	Intermediate Similarity	NPC196063
0.8054	Intermediate Similarity	NPC300894
0.8054	Intermediate Similarity	NPC141455
0.8054	Intermediate Similarity	NPC296954
0.8041	Intermediate Similarity	NPC284957
0.8041	Intermediate Similarity	NPC140502
0.8026	Intermediate Similarity	NPC478242
0.8025	Intermediate Similarity	NPC76211
0.8025	Intermediate Similarity	NPC469384
0.8015	Intermediate Similarity	NPC282409
0.8015	Intermediate Similarity	NPC469702
0.8014	Intermediate Similarity	NPC475195
0.8014	Intermediate Similarity	NPC260425
0.8014	Intermediate Similarity	NPC476376
0.8014	Intermediate Similarity	NPC78363
0.8014	Intermediate Similarity	NPC170718
0.8013	Intermediate Similarity	NPC478266
0.8013	Intermediate Similarity	NPC296377
0.8012	Intermediate Similarity	NPC286809
0.8	Intermediate Similarity	NPC85624
0.8	Intermediate Similarity	NPC202729
0.7987	Intermediate Similarity	NPC478268
0.7987	Intermediate Similarity	NPC469367
0.7987	Intermediate Similarity	NPC40305
0.7987	Intermediate Similarity	NPC105005

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 NPC159387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	717
0.2-0.3	1690
0.3-0.4	2746
0.4-0.5	2133
0.5-0.6	1261
0.6-0.7	339
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8082	Intermediate Similarity	NPD7266	Discontinued
0.8037	Intermediate Similarity	NPD7685	Pre-registration
0.7568	Intermediate Similarity	NPD6653	Approved
0.7452	Intermediate Similarity	NPD1653	Approved
0.7451	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6190	Approved
0.7379	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6005	Phase 3
0.7368	Intermediate Similarity	NPD6002	Phase 3
0.7368	Intermediate Similarity	NPD6004	Phase 3
0.7368	Intermediate Similarity	NPD5763	Approved
0.7368	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5762	Approved
0.7329	Intermediate Similarity	NPD5736	Approved
0.731	Intermediate Similarity	NPD3094	Phase 2
0.7273	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD1091	Approved
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD37	Approved
0.726	Intermediate Similarity	NPD5647	Approved
0.7256	Intermediate Similarity	NPD6234	Discontinued
0.7239	Intermediate Similarity	NPD4967	Phase 2
0.7239	Intermediate Similarity	NPD4965	Approved
0.7239	Intermediate Similarity	NPD4966	Approved
0.7225	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8455	Phase 2
0.72	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6362	Approved
0.7181	Intermediate Similarity	NPD3764	Approved
0.7171	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7097	Phase 1
0.716	Intermediate Similarity	NPD3818	Discontinued
0.716	Intermediate Similarity	NPD7228	Approved
0.7153	Intermediate Similarity	NPD3092	Approved
0.7133	Intermediate Similarity	NPD6663	Approved
0.7124	Intermediate Similarity	NPD7033	Discontinued
0.7113	Intermediate Similarity	NPD9545	Approved
0.7093	Intermediate Similarity	NPD6559	Discontinued
0.7086	Intermediate Similarity	NPD4140	Approved
0.7083	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.7059	Intermediate Similarity	NPD7799	Discontinued
0.7039	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5124	Phase 1
0.7037	Intermediate Similarity	NPD4380	Phase 2
0.7037	Intermediate Similarity	NPD7028	Phase 2
0.7018	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD3027	Phase 3
0.6987	Remote Similarity	NPD2424	Discontinued
0.6985	Remote Similarity	NPD6685	Approved
0.698	Remote Similarity	NPD2861	Phase 2
0.6978	Remote Similarity	NPD969	Suspended
0.6974	Remote Similarity	NPD4060	Phase 1
0.6943	Remote Similarity	NPD1652	Phase 2
0.6934	Remote Similarity	NPD1358	Approved
0.6928	Remote Similarity	NPD230	Phase 1
0.6928	Remote Similarity	NPD5735	Approved
0.6919	Remote Similarity	NPD7054	Approved
0.6918	Remote Similarity	NPD5058	Phase 3
0.6918	Remote Similarity	NPD3705	Approved
0.6918	Remote Similarity	NPD422	Phase 1
0.6914	Remote Similarity	NPD8312	Approved
0.6914	Remote Similarity	NPD8313	Approved
0.6908	Remote Similarity	NPD6233	Phase 2
0.6901	Remote Similarity	NPD7157	Approved
0.6899	Remote Similarity	NPD8166	Discontinued
0.6897	Remote Similarity	NPD5125	Phase 3
0.6897	Remote Similarity	NPD5126	Approved
0.6887	Remote Similarity	NPD7095	Approved
0.6886	Remote Similarity	NPD7075	Discontinued
0.6879	Remote Similarity	NPD7074	Phase 3
0.6879	Remote Similarity	NPD7472	Approved
0.6875	Remote Similarity	NPD3091	Approved
0.6871	Remote Similarity	NPD7458	Discontinued
0.6863	Remote Similarity	NPD3620	Phase 2
0.6863	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3134	Approved
0.6857	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6801	Discontinued
0.6846	Remote Similarity	NPD2797	Approved
0.6842	Remote Similarity	NPD6798	Discontinued
0.6839	Remote Similarity	NPD6797	Phase 2
0.6833	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4340	Discontinued
0.6809	Remote Similarity	NPD7843	Approved
0.68	Remote Similarity	NPD7251	Discontinued
0.68	Remote Similarity	NPD7240	Approved
0.6792	Remote Similarity	NPD4110	Phase 3
0.6792	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3750	Approved
0.679	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5958	Discontinued
0.6765	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5765	Approved
0.6763	Remote Similarity	NPD2684	Approved
0.6761	Remote Similarity	NPD7808	Phase 3
0.6759	Remote Similarity	NPD7741	Discontinued
0.6752	Remote Similarity	NPD2935	Discontinued
0.6748	Remote Similarity	NPD5403	Approved
0.6738	Remote Similarity	NPD6912	Phase 3
0.6732	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3268	Approved
0.673	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6674	Discontinued
0.6728	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1357	Approved
0.6711	Remote Similarity	NPD4908	Phase 1
0.6708	Remote Similarity	NPD7236	Approved
0.6707	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD3095	Discontinued
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD6799	Approved
0.6646	Remote Similarity	NPD2438	Suspended
0.6645	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1613	Approved
0.6644	Remote Similarity	NPD1608	Approved
0.6642	Remote Similarity	NPD6647	Phase 2
0.6627	Remote Similarity	NPD6599	Discontinued
0.6626	Remote Similarity	NPD5401	Approved
0.6623	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD987	Approved
0.6622	Remote Similarity	NPD3496	Discontinued
0.6622	Remote Similarity	NPD3847	Discontinued
0.6621	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7239	Suspended
0.6599	Remote Similarity	NPD7503	Approved
0.6599	Remote Similarity	NPD5691	Approved
0.6597	Remote Similarity	NPD2629	Approved
0.6596	Remote Similarity	NPD2067	Discontinued
0.6596	Remote Similarity	NPD3021	Approved
0.6596	Remote Similarity	NPD3022	Approved
0.6582	Remote Similarity	NPD2799	Discontinued
0.6582	Remote Similarity	NPD1510	Phase 2
0.6579	Remote Similarity	NPD4624	Approved
0.6579	Remote Similarity	NPD2798	Approved
0.6577	Remote Similarity	NPD1610	Phase 2
0.6568	Remote Similarity	NPD3817	Phase 2
0.6562	Remote Similarity	NPD4534	Discontinued
0.6561	Remote Similarity	NPD6353	Approved
0.6556	Remote Similarity	NPD8651	Approved
0.6556	Remote Similarity	NPD3225	Approved
0.6554	Remote Similarity	NPD4059	Approved
0.6554	Remote Similarity	NPD3019	Approved
0.6554	Remote Similarity	NPD2932	Approved
0.6548	Remote Similarity	NPD1934	Approved
0.6538	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5844	Phase 1
0.6529	Remote Similarity	NPD7768	Phase 2
0.6524	Remote Similarity	NPD2532	Approved
0.6524	Remote Similarity	NPD2534	Approved
0.6524	Remote Similarity	NPD2533	Approved
0.6524	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4538	Approved
0.6519	Remote Similarity	NPD8434	Phase 2
0.6519	Remote Similarity	NPD4536	Approved
0.6517	Remote Similarity	NPD6765	Approved
0.6517	Remote Similarity	NPD6764	Approved
0.6509	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5761	Phase 2
0.6509	Remote Similarity	NPD7819	Suspended
0.6509	Remote Similarity	NPD5760	Phase 2
0.6507	Remote Similarity	NPD9493	Approved
0.6503	Remote Similarity	NPD6667	Approved
0.6503	Remote Similarity	NPD6666	Approved
0.649	Remote Similarity	NPD3685	Discontinued
0.649	Remote Similarity	NPD5327	Phase 3
0.6488	Remote Similarity	NPD7411	Suspended
0.6486	Remote Similarity	NPD5585	Approved
0.6481	Remote Similarity	NPD3400	Discontinued
0.648	Remote Similarity	NPD7930	Approved
0.6478	Remote Similarity	NPD4308	Phase 3
0.6478	Remote Similarity	NPD3748	Approved
0.6478	Remote Similarity	NPD5588	Approved
0.6477	Remote Similarity	NPD3751	Discontinued
0.6475	Remote Similarity	NPD5909	Discontinued
0.6474	Remote Similarity	NPD7497	Discontinued
0.6474	Remote Similarity	NPD7435	Discontinued
0.6471	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6085	Phase 2
0.6467	Remote Similarity	NPD3455	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