NPASS Compound

Structure

NPC209473 OpenBabel07101718312D 37 41 0 0 1 0 0 0 0 0999 V2000 3.5838 -2.1161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0227 0.2815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4446 3.0149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7810 3.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2056 3.8760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8247 -2.1946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9199 -1.2885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9923 -2.5652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1828 -0.7529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2552 -2.0296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7005 -0.8323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9772 0.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2360 -1.5694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5127 -0.6419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4446 1.1927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6556 -0.1740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3505 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0711 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1422 -1.4742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4446 0.2815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6556 1.6482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8665 0.2815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4021 1.9298 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4021 1.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8665 1.1927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5355 2.2113 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1392 2.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5355 0.7371 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.4742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2540 3.0778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9715 2.0947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6777 -2.2113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2337 -0.1740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6556 2.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0439 3.3714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5355 2.2113 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 32 1 0 0 0 0 2 33 1 0 0 0 0 3 34 1 0 0 0 0 4 35 1 0 0 0 0 5 36 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 24 1 0 0 0 0 18 28 1 0 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 21 25 2 0 0 0 0 21 34 1 0 0 0 0 22 25 1 0 0 0 0 22 37 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 23 27 1 6 0 0 0 24 28 1 1 0 0 0 25 29 1 0 0 0 0 26 29 1 6 0 0 0 26 30 1 0 0 0 0 27 31 2 0 0 0 0 27 35 1 0 0 0 0 28 29 1 1 0 0 0 28 37 1 0 0 0 0 29 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	168.04
Volume:	162.983
LogP:	1.376
LogD:	1.116
LogS:	-1.886
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	2.307
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.843
MDCK Permeability:	9.629229680285789e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	82.68657684326172%
Volume Distribution (VD):	0.833
Pgp-substrate:	19.429452896118164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.917
CYP1A2-substrate:	0.365
CYP2C19-inhibitor:	0.111
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.32
CYP2C9-substrate:	0.839
CYP2D6-inhibitor:	0.56
CYP2D6-substrate:	0.305
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	14.256
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.084
Drug-inuced Liver Injury (DILI):	0.756
AMES Toxicity:	0.526
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.198
Skin Sensitization:	0.895
Carcinogencity:	0.055
Eye Corrosion:	0.663
Eye Irritation:	0.96
Respiratory Toxicity:	0.739

Download Data

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

Natural Product: NPC209473

Natural Product ID:	NPC209473
*Common Name:**	Methyl 8B-Omethylrocaglate
IUPAC Name:	methyl (1R,2R,3S,3aR,8bS)-1-hydroxy-6,8,8b-trimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
Synonyms:	Methyl 8B-Omethylrocaglate
Standard InCHIKey:	OAKWLIZTUWAJDM-IDAMAFBJSA-N
Standard InCHI:	InChI=1S/C29H30O8/c1-32-19-13-11-18(12-14-19)28-24(17-9-7-6-8-10-17)23(27(31)35-4)26(30)29(28,36-5)25-21(34-3)15-20(33-2)16-22(25)37-28/h6-16,23-24,26,30H,1-5H3/t23-,24-,26-,28+,29+/m1/s1
SMILES:	COc1ccc(cc1)[C@]12Oc3c([C@]2(OC)[C@@H]([C@@H]([C@H]1c1ccccc1)C(=O)OC)O)c(OC)cc(c3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2331812
PubChem CID:	21670099
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0003109] Flavaglines

*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
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO4720	Aglaia perviridis	Species	Meliaceae	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
ED50	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	4.9	uM	PMID[549428]
NPT27	Others	Unspecified		ED50	>	50.0	uM	PMID[549428]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	>	20.0	uM	PMID[549428]

☑ 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 NPC209473 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	338
0.1-0.2	1323
0.2-0.3	2974
0.3-0.4	6601
0.4-0.5	11121
0.5-0.6	6262
0.6-0.7	6516
0.7-0.8	7448
0.8-0.85	95
0.85-0.9	4
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC73422
0.9934	High Similarity	NPC310399
0.9868	High Similarity	NPC329743
0.9739	High Similarity	NPC90336
0.9375	High Similarity	NPC149502
0.9375	High Similarity	NPC254071
0.9375	High Similarity	NPC271755
0.9375	High Similarity	NPC222665
0.9259	High Similarity	NPC107739
0.9202	High Similarity	NPC23593
0.9139	High Similarity	NPC20360
0.9091	High Similarity	NPC236089
0.9085	High Similarity	NPC263955
0.903	High Similarity	NPC29587
0.8933	High Similarity	NPC470937
0.8874	High Similarity	NPC184607
0.869	High Similarity	NPC206061
0.8642	High Similarity	NPC92589
0.8442	Intermediate Similarity	NPC307287
0.8438	Intermediate Similarity	NPC473236
0.8434	Intermediate Similarity	NPC475621
0.8415	Intermediate Similarity	NPC186228
0.8395	Intermediate Similarity	NPC165483
0.8375	Intermediate Similarity	NPC51543
0.8352	Intermediate Similarity	NPC308709
0.8344	Intermediate Similarity	NPC212697
0.8333	Intermediate Similarity	NPC164152
0.8323	Intermediate Similarity	NPC87363
0.8291	Intermediate Similarity	NPC469700
0.8284	Intermediate Similarity	NPC91043
0.8282	Intermediate Similarity	NPC475797
0.8282	Intermediate Similarity	NPC474738
0.8282	Intermediate Similarity	NPC109967
0.8282	Intermediate Similarity	NPC78554
0.8282	Intermediate Similarity	NPC189730
0.8282	Intermediate Similarity	NPC129053
0.8282	Intermediate Similarity	NPC469936
0.8282	Intermediate Similarity	NPC321372
0.8282	Intermediate Similarity	NPC474609
0.8235	Intermediate Similarity	NPC472584
0.8221	Intermediate Similarity	NPC108937
0.8221	Intermediate Similarity	NPC279218
0.8199	Intermediate Similarity	NPC475379
0.8198	Intermediate Similarity	NPC324220
0.8198	Intermediate Similarity	NPC312630
0.8193	Intermediate Similarity	NPC124747
0.8193	Intermediate Similarity	NPC109061
0.8193	Intermediate Similarity	NPC97812
0.8193	Intermediate Similarity	NPC155754
0.8187	Intermediate Similarity	NPC125570
0.8187	Intermediate Similarity	NPC169605
0.8182	Intermediate Similarity	NPC94220
0.8182	Intermediate Similarity	NPC166456
0.8182	Intermediate Similarity	NPC24339
0.8182	Intermediate Similarity	NPC98083
0.8182	Intermediate Similarity	NPC7543
0.8176	Intermediate Similarity	NPC120220
0.8171	Intermediate Similarity	NPC166116
0.8171	Intermediate Similarity	NPC55463
0.8171	Intermediate Similarity	NPC470625
0.8171	Intermediate Similarity	NPC471787
0.8166	Intermediate Similarity	NPC167231
0.8166	Intermediate Similarity	NPC476459
0.8166	Intermediate Similarity	NPC215802
0.8148	Intermediate Similarity	NPC474744
0.8148	Intermediate Similarity	NPC476434
0.8148	Intermediate Similarity	NPC56184
0.8148	Intermediate Similarity	NPC471675
0.8148	Intermediate Similarity	NPC200773
0.8148	Intermediate Similarity	NPC472423
0.8148	Intermediate Similarity	NPC476335
0.8148	Intermediate Similarity	NPC240768
0.8148	Intermediate Similarity	NPC474772
0.8148	Intermediate Similarity	NPC472636
0.8144	Intermediate Similarity	NPC476244
0.8133	Intermediate Similarity	NPC476337
0.8133	Intermediate Similarity	NPC472055
0.8132	Intermediate Similarity	NPC235698
0.8121	Intermediate Similarity	NPC476340
0.8118	Intermediate Similarity	NPC217378
0.8114	Intermediate Similarity	NPC186746
0.811	Intermediate Similarity	NPC469934
0.811	Intermediate Similarity	NPC473241
0.8107	Intermediate Similarity	NPC476277
0.8098	Intermediate Similarity	NPC476238
0.8098	Intermediate Similarity	NPC285623
0.8098	Intermediate Similarity	NPC31627
0.8098	Intermediate Similarity	NPC473996
0.8098	Intermediate Similarity	NPC258128
0.8098	Intermediate Similarity	NPC327269
0.8098	Intermediate Similarity	NPC65591
0.8098	Intermediate Similarity	NPC178574
0.8095	Intermediate Similarity	NPC134047
0.8095	Intermediate Similarity	NPC214279
0.8095	Intermediate Similarity	NPC471286
0.8095	Intermediate Similarity	NPC223006
0.8095	Intermediate Similarity	NPC91288
0.8095	Intermediate Similarity	NPC272750
0.8095	Intermediate Similarity	NPC173729
0.8086	Intermediate Similarity	NPC472421
0.8084	Intermediate Similarity	NPC14822
0.8084	Intermediate Similarity	NPC96031
0.8075	Intermediate Similarity	NPC477698
0.8072	Intermediate Similarity	NPC50430
0.8072	Intermediate Similarity	NPC470339
0.8072	Intermediate Similarity	NPC43761
0.8061	Intermediate Similarity	NPC127406
0.8061	Intermediate Similarity	NPC215917
0.8061	Intermediate Similarity	NPC20530
0.8061	Intermediate Similarity	NPC475378
0.8061	Intermediate Similarity	NPC10754
0.8049	Intermediate Similarity	NPC303950
0.8049	Intermediate Similarity	NPC136757
0.8047	Intermediate Similarity	NPC222531
0.8047	Intermediate Similarity	NPC318472
0.8037	Intermediate Similarity	NPC148945
0.8037	Intermediate Similarity	NPC471229
0.8037	Intermediate Similarity	NPC472580
0.8037	Intermediate Similarity	NPC472422
0.8037	Intermediate Similarity	NPC263384
0.8037	Intermediate Similarity	NPC290671
0.8037	Intermediate Similarity	NPC28724
0.8037	Intermediate Similarity	NPC295650
0.8037	Intermediate Similarity	NPC472420
0.8037	Intermediate Similarity	NPC78835
0.8037	Intermediate Similarity	NPC471677
0.8037	Intermediate Similarity	NPC317715
0.8037	Intermediate Similarity	NPC309512
0.8037	Intermediate Similarity	NPC204561
0.8037	Intermediate Similarity	NPC244577
0.8037	Intermediate Similarity	NPC70016
0.8037	Intermediate Similarity	NPC316960
0.8037	Intermediate Similarity	NPC215921
0.8037	Intermediate Similarity	NPC471676
0.8036	Intermediate Similarity	NPC144557
0.8036	Intermediate Similarity	NPC55121
0.8036	Intermediate Similarity	NPC93215
0.8025	Intermediate Similarity	NPC107197
0.8025	Intermediate Similarity	NPC103116
0.8025	Intermediate Similarity	NPC164299
0.8025	Intermediate Similarity	NPC277032
0.8024	Intermediate Similarity	NPC95472
0.8024	Intermediate Similarity	NPC470810
0.8024	Intermediate Similarity	NPC239270
0.8024	Intermediate Similarity	NPC303210
0.8024	Intermediate Similarity	NPC49009
0.8024	Intermediate Similarity	NPC24164
0.8024	Intermediate Similarity	NPC96593
0.8024	Intermediate Similarity	NPC74749
0.8024	Intermediate Similarity	NPC43971
0.8024	Intermediate Similarity	NPC53889
0.8024	Intermediate Similarity	NPC119910
0.8024	Intermediate Similarity	NPC19554
0.8012	Intermediate Similarity	NPC114179
0.8012	Intermediate Similarity	NPC207584
0.8012	Intermediate Similarity	NPC14875
0.8012	Intermediate Similarity	NPC43638
0.8012	Intermediate Similarity	NPC289322
0.8012	Intermediate Similarity	NPC160512
0.8012	Intermediate Similarity	NPC156818
0.8012	Intermediate Similarity	NPC38779
0.8012	Intermediate Similarity	NPC68324
0.8012	Intermediate Similarity	NPC473395
0.8012	Intermediate Similarity	NPC19947
0.8011	Intermediate Similarity	NPC293347
0.8	Intermediate Similarity	NPC316535
0.8	Intermediate Similarity	NPC119589
0.8	Intermediate Similarity	NPC477530
0.8	Intermediate Similarity	NPC142479
0.8	Intermediate Similarity	NPC43065
0.8	Intermediate Similarity	NPC311144
0.8	Intermediate Similarity	NPC155015
0.8	Intermediate Similarity	NPC82330
0.8	Intermediate Similarity	NPC470681
0.8	Intermediate Similarity	NPC186316
0.7988	Intermediate Similarity	NPC217149
0.7988	Intermediate Similarity	NPC477957
0.7988	Intermediate Similarity	NPC210597
0.7988	Intermediate Similarity	NPC63438
0.7988	Intermediate Similarity	NPC150123
0.7988	Intermediate Similarity	NPC256141
0.7988	Intermediate Similarity	NPC244583
0.7988	Intermediate Similarity	NPC10807
0.7988	Intermediate Similarity	NPC475790
0.7988	Intermediate Similarity	NPC56232
0.7988	Intermediate Similarity	NPC327694
0.7988	Intermediate Similarity	NPC476154
0.7988	Intermediate Similarity	NPC161881
0.7988	Intermediate Similarity	NPC216035
0.7976	Intermediate Similarity	NPC288149
0.7976	Intermediate Similarity	NPC45124
0.7976	Intermediate Similarity	NPC139540
0.7976	Intermediate Similarity	NPC30655
0.7976	Intermediate Similarity	NPC177100
0.7976	Intermediate Similarity	NPC74854
0.7976	Intermediate Similarity	NPC115624
0.7975	Intermediate Similarity	NPC164082
0.7975	Intermediate Similarity	NPC474735
0.7975	Intermediate Similarity	NPC267117
0.7975	Intermediate Similarity	NPC327059

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 NPC209473 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	811
0.2-0.3	1714
0.3-0.4	2596
0.4-0.5	2075
0.5-0.6	1105
0.6-0.7	422
0.7-0.8	133
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD7199	Phase 2
0.8424	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6002	Phase 3
0.8013	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6005	Phase 3
0.8013	Intermediate Similarity	NPD6004	Phase 3
0.8	Intermediate Similarity	NPD7033	Discontinued
0.7952	Intermediate Similarity	NPD4965	Approved
0.7952	Intermediate Similarity	NPD4966	Approved
0.7952	Intermediate Similarity	NPD4967	Phase 2
0.7952	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6355	Discontinued
0.7904	Intermediate Similarity	NPD7075	Discontinued
0.7888	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD37	Approved
0.7879	Intermediate Similarity	NPD6801	Discontinued
0.7857	Intermediate Similarity	NPD6234	Discontinued
0.7843	Intermediate Similarity	NPD6798	Discontinued
0.7826	Intermediate Similarity	NPD6799	Approved
0.7824	Intermediate Similarity	NPD7229	Phase 3
0.7818	Intermediate Similarity	NPD7411	Suspended
0.7798	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3817	Phase 2
0.7758	Intermediate Similarity	NPD4380	Phase 2
0.7758	Intermediate Similarity	NPD6599	Discontinued
0.7746	Intermediate Similarity	NPD3818	Discontinued
0.7733	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6166	Phase 2
0.7725	Intermediate Similarity	NPD7819	Suspended
0.7697	Intermediate Similarity	NPD5647	Approved
0.7692	Intermediate Similarity	NPD3749	Approved
0.7677	Intermediate Similarity	NPD6233	Phase 2
0.7665	Intermediate Similarity	NPD1934	Approved
0.7644	Intermediate Similarity	NPD7228	Approved
0.764	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD5760	Phase 2
0.7619	Intermediate Similarity	NPD8455	Phase 2
0.7619	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5761	Phase 2
0.7616	Intermediate Similarity	NPD3787	Discontinued
0.7616	Intermediate Similarity	NPD6232	Discontinued
0.761	Intermediate Similarity	NPD2796	Approved
0.7602	Intermediate Similarity	NPD5494	Approved
0.76	Intermediate Similarity	NPD5844	Phase 1
0.7597	Intermediate Similarity	NPD4908	Phase 1
0.7586	Intermediate Similarity	NPD7473	Discontinued
0.7576	Intermediate Similarity	NPD5403	Approved
0.7574	Intermediate Similarity	NPD5402	Approved
0.7571	Intermediate Similarity	NPD6559	Discontinued
0.7571	Intermediate Similarity	NPD7685	Pre-registration
0.7562	Intermediate Similarity	NPD5762	Approved
0.7562	Intermediate Similarity	NPD5763	Approved
0.7562	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5401	Approved
0.7561	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6653	Approved
0.7529	Intermediate Similarity	NPD7768	Phase 2
0.7529	Intermediate Similarity	NPD3882	Suspended
0.7529	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1549	Phase 2
0.7515	Intermediate Similarity	NPD2801	Approved
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7240	Approved
0.7469	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7074	Phase 3
0.743	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7097	Phase 1
0.7365	Intermediate Similarity	NPD920	Approved
0.7365	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.736	Intermediate Similarity	NPD7472	Approved
0.7356	Intermediate Similarity	NPD6959	Discontinued
0.7356	Intermediate Similarity	NPD8127	Discontinued
0.7349	Intermediate Similarity	NPD2534	Approved
0.7349	Intermediate Similarity	NPD2532	Approved
0.7349	Intermediate Similarity	NPD2533	Approved
0.7345	Intermediate Similarity	NPD3751	Discontinued
0.7329	Intermediate Similarity	NPD1510	Phase 2
0.732	Intermediate Similarity	NPD1608	Approved
0.7318	Intermediate Similarity	NPD6797	Phase 2
0.7317	Intermediate Similarity	NPD3750	Approved
0.7305	Intermediate Similarity	NPD6273	Approved
0.7301	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1613	Approved
0.7296	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4140	Approved
0.729	Intermediate Similarity	NPD6362	Approved
0.729	Intermediate Similarity	NPD2797	Approved
0.7289	Intermediate Similarity	NPD1511	Approved
0.7284	Intermediate Similarity	NPD6099	Approved
0.7284	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD7251	Discontinued
0.7273	Intermediate Similarity	NPD6190	Approved
0.7256	Intermediate Similarity	NPD1652	Phase 2
0.7255	Intermediate Similarity	NPD1610	Phase 2
0.725	Intermediate Similarity	NPD5735	Approved
0.725	Intermediate Similarity	NPD5124	Phase 1
0.725	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7808	Phase 3
0.7222	Intermediate Similarity	NPD2799	Discontinued
0.7222	Intermediate Similarity	NPD3748	Approved
0.7215	Intermediate Similarity	NPD7095	Approved
0.7212	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1465	Phase 2
0.7202	Intermediate Similarity	NPD1512	Approved
0.7197	Intermediate Similarity	NPD2861	Phase 2
0.7195	Intermediate Similarity	NPD5958	Discontinued
0.7188	Intermediate Similarity	NPD1240	Approved
0.7178	Intermediate Similarity	NPD1551	Phase 2
0.7175	Intermediate Similarity	NPD3926	Phase 2
0.7152	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD1243	Approved
0.7126	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4062	Phase 3
0.7124	Intermediate Similarity	NPD17	Approved
0.7112	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4110	Phase 3
0.7108	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3027	Phase 3
0.7104	Intermediate Similarity	NPD8313	Approved
0.7104	Intermediate Similarity	NPD8312	Approved
0.7099	Intermediate Similarity	NPD1607	Approved
0.7091	Intermediate Similarity	NPD2424	Discontinued
0.7088	Intermediate Similarity	NPD6764	Approved
0.7088	Intermediate Similarity	NPD6765	Approved
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.7076	Intermediate Similarity	NPD3226	Approved
0.707	Intermediate Similarity	NPD3266	Approved
0.707	Intermediate Similarity	NPD3267	Approved
0.7063	Intermediate Similarity	NPD3764	Approved
0.7053	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD919	Approved
0.7044	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6832	Phase 2
0.7033	Intermediate Similarity	NPD5953	Discontinued
0.703	Intermediate Similarity	NPD2344	Approved
0.703	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7315	Approved
0.7006	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1548	Phase 1
0.6988	Remote Similarity	NPD4534	Discontinued
0.6981	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2935	Discontinued
0.6961	Remote Similarity	NPD7799	Discontinued
0.6957	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2313	Discontinued
0.6935	Remote Similarity	NPD6784	Approved
0.6935	Remote Similarity	NPD6785	Approved
0.6923	Remote Similarity	NPD7497	Discontinued
0.6923	Remote Similarity	NPD5058	Phase 3
0.6923	Remote Similarity	NPD422	Phase 1
0.6923	Remote Similarity	NPD7680	Approved
0.6923	Remote Similarity	NPD7286	Phase 2
0.6919	Remote Similarity	NPD1653	Approved
0.6918	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8032	Phase 2
0.6914	Remote Similarity	NPD6663	Approved
0.691	Remote Similarity	NPD6746	Phase 2
0.6905	Remote Similarity	NPD7466	Approved
0.6905	Remote Similarity	NPD3892	Phase 2
0.6899	Remote Similarity	NPD3225	Approved
0.6893	Remote Similarity	NPD6971	Discontinued
0.6891	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6353	Approved
0.6883	Remote Similarity	NPD1894	Discontinued
0.6882	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7458	Discontinued
0.6872	Remote Similarity	NPD1247	Approved
0.6867	Remote Similarity	NPD4476	Approved
0.6867	Remote Similarity	NPD6032	Approved
0.6867	Remote Similarity	NPD4477	Approved
0.6867	Remote Similarity	NPD5712	Approved
0.6867	Remote Similarity	NPD2438	Suspended
0.6864	Remote Similarity	NPD2309	Approved
0.6854	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1296	Phase 2
0.6851	Remote Similarity	NPD2403	Approved
0.685	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7783	Phase 2
0.6845	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7028	Phase 2
0.6835	Remote Similarity	NPD4749	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data