NPASS Compound

Structure

NPC120774 OpenBabel07101719512D 41 45 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 4.3301 1.5000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 6.9282 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 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 1.7321 -1.0000 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 -0.0000 2.0000 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 35 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 8 2 0 0 0 0 4 16 1 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 9 2 0 0 0 0 6 17 1 0 0 0 0 7 11 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 22 1 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 38 1 0 0 0 0 18 28 1 0 0 0 0 19 21 2 0 0 0 0 19 31 1 0 0 0 0 20 22 2 0 0 0 0 20 32 1 0 0 0 0 21 35 1 0 0 0 0 22 36 1 0 0 0 0 23 29 2 0 0 0 0 23 37 1 0 0 0 0 24 15 1 6 0 0 0 24 27 1 0 0 0 0 24 39 1 0 0 0 0 25 33 2 0 0 0 0 25 38 1 0 0 0 0 26 34 2 0 0 0 0 26 40 1 0 0 0 0 27 17 1 1 0 0 0 27 41 1 0 0 0 0 28 30 2 0 0 0 0 28 40 1 0 0 0 0 29 30 1 0 0 0 0 29 41 1 0 0 0 0 30 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.15
Volume:	547.072
LogP:	3.704
LogD:	3.063
LogS:	-4.563
# Rotatable Bonds:	9
TPSA:	143.12
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.18
Synthetic Accessibility Score:	3.732
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.837
MDCK Permeability:	5.532310751732439e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.122
30% Bioavailability (F30%):	0.623

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	94.1529769897461%
Volume Distribution (VD):	0.392
Pgp-substrate:	13.112747192382812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.155
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.791
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.878
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.239
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.586
CYP3A4-substrate:	0.778

ADMET: Excretion

Clearance (CL):	6.292
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.172
Human Hepatotoxicity (H-HT):	0.715
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.256
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.932
Carcinogencity:	0.475
Eye Corrosion:	0.003
Eye Irritation:	0.197
Respiratory Toxicity:	0.069

Download Data

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

Natural Product: NPC120774

Natural Product ID:	NPC120774
*Common Name:**	Repenin B
IUPAC Name:	[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	RDPYGDKKJMTRLB-KTRJKXECSA-N
Standard InCHI:	InChI=1S/C30H26O11/c1-35-21-12-16(4-8-19(21)31)5-10-25(33)38-15-24-27(17-6-9-20(32)22(13-17)36-2)41-29-23(37-3)14-18-7-11-26(34)40-28(18)30(29)39-24/h4-14,24,27,31-32H,15H2,1-3H3/b10-5+/t24-,27-/m1/s1
SMILES:	COc1cc(ccc1O)/C=C/C(=O)OC[C@@H]1[C@@H](c2ccc(c(c2)OC)O)Oc2c(cc3ccc(=O)oc3c2O1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452452
PubChem CID:	44511362
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0002545] Coumarinolignans

*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
NPO32501	Duranta erecta	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19464173]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	420000.0	nM	PMID[525183]

☑ 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 NPC120774 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	425
0.1-0.2	1787
0.2-0.3	4837
0.3-0.4	10042
0.4-0.5	7797
0.5-0.6	3992
0.6-0.7	5398
0.7-0.8	4920
0.8-0.85	2006
0.85-0.9	1326
0.9-0.95	154
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC163598
1.0	High Similarity	NPC264875
0.9792	High Similarity	NPC30688
0.9792	High Similarity	NPC176903
0.9724	High Similarity	NPC205727
0.9724	High Similarity	NPC21184
0.9724	High Similarity	NPC120426
0.9724	High Similarity	NPC294522
0.9586	High Similarity	NPC187398
0.9586	High Similarity	NPC476348
0.9517	High Similarity	NPC476347
0.9517	High Similarity	NPC15577
0.9463	High Similarity	NPC8712
0.9448	High Similarity	NPC268515
0.9448	High Similarity	NPC40222
0.929	High Similarity	NPC142614
0.9241	High Similarity	NPC256555
0.9241	High Similarity	NPC110067
0.9241	High Similarity	NPC91492
0.9241	High Similarity	NPC34245
0.9241	High Similarity	NPC7439
0.9205	High Similarity	NPC268484
0.9139	High Similarity	NPC150442
0.9139	High Similarity	NPC223720
0.9133	High Similarity	NPC213197
0.9128	High Similarity	NPC475250
0.9122	High Similarity	NPC231149
0.9097	High Similarity	NPC13067
0.9073	High Similarity	NPC53587
0.9073	High Similarity	NPC476352
0.9073	High Similarity	NPC176186
0.9073	High Similarity	NPC169404
0.9073	High Similarity	NPC215060
0.906	High Similarity	NPC139839
0.906	High Similarity	NPC48366
0.9028	High Similarity	NPC148835
0.9028	High Similarity	NPC139548
0.9028	High Similarity	NPC76336
0.9028	High Similarity	NPC95162
0.9028	High Similarity	NPC20511
0.9028	High Similarity	NPC52086
0.9	High Similarity	NPC212670
0.9	High Similarity	NPC313334
0.9	High Similarity	NPC206264
0.8993	High Similarity	NPC275125
0.8993	High Similarity	NPC178129
0.8993	High Similarity	NPC97937
0.8993	High Similarity	NPC170239
0.8973	High Similarity	NPC300611
0.8966	High Similarity	NPC43500
0.8966	High Similarity	NPC164148
0.8961	High Similarity	NPC284810
0.8958	High Similarity	NPC126682
0.8958	High Similarity	NPC82271
0.8954	High Similarity	NPC62903
0.8954	High Similarity	NPC7178
0.894	High Similarity	NPC114740
0.8933	High Similarity	NPC281549
0.8933	High Similarity	NPC96294
0.8933	High Similarity	NPC93924
0.8933	High Similarity	NPC478237
0.8926	High Similarity	NPC205361
0.8919	High Similarity	NPC185127
0.8912	High Similarity	NPC278469
0.8912	High Similarity	NPC193722
0.891	High Similarity	NPC53889
0.8903	High Similarity	NPC125495
0.8897	High Similarity	NPC474886
0.8897	High Similarity	NPC326797
0.8897	High Similarity	NPC102904
0.8897	High Similarity	NPC107551
0.8897	High Similarity	NPC176051
0.8897	High Similarity	NPC103976
0.8897	High Similarity	NPC126206
0.8897	High Similarity	NPC474282
0.8897	High Similarity	NPC38874
0.8896	High Similarity	NPC142479
0.8896	High Similarity	NPC155015
0.8889	High Similarity	NPC474656
0.8874	High Similarity	NPC106138
0.8874	High Similarity	NPC113790
0.8867	High Similarity	NPC41844
0.8859	High Similarity	NPC473909
0.8859	High Similarity	NPC143120
0.8859	High Similarity	NPC125617
0.8859	High Similarity	NPC274960
0.8851	High Similarity	NPC138212
0.8846	High Similarity	NPC87317
0.8844	High Similarity	NPC224876
0.8844	High Similarity	NPC83375
0.8828	High Similarity	NPC471664
0.8828	High Similarity	NPC286843
0.8828	High Similarity	NPC471665
0.8819	High Similarity	NPC474600
0.8819	High Similarity	NPC111635
0.8819	High Similarity	NPC309953
0.8819	High Similarity	NPC92830
0.8808	High Similarity	NPC252402
0.8808	High Similarity	NPC102934
0.88	High Similarity	NPC199928
0.8792	High Similarity	NPC171932
0.8792	High Similarity	NPC471763
0.8792	High Similarity	NPC28440
0.879	High Similarity	NPC24164
0.879	High Similarity	NPC301089
0.8784	High Similarity	NPC469564
0.8782	High Similarity	NPC68324
0.8782	High Similarity	NPC114179
0.8782	High Similarity	NPC289322
0.8782	High Similarity	NPC160512
0.8782	High Similarity	NPC156818
0.8782	High Similarity	NPC38779
0.8776	High Similarity	NPC267291
0.8776	High Similarity	NPC262189
0.8776	High Similarity	NPC22317
0.8767	High Similarity	NPC211549
0.8767	High Similarity	NPC276490
0.8766	High Similarity	NPC476154
0.8766	High Similarity	NPC475141
0.8759	High Similarity	NPC470356
0.8759	High Similarity	NPC94750
0.8759	High Similarity	NPC224941
0.8759	High Similarity	NPC112246
0.8759	High Similarity	NPC474206
0.8759	High Similarity	NPC112939
0.8759	High Similarity	NPC472337
0.8759	High Similarity	NPC121812
0.8759	High Similarity	NPC234865
0.8759	High Similarity	NPC311430
0.8758	High Similarity	NPC476279
0.875	High Similarity	NPC26673
0.875	High Similarity	NPC277021
0.875	High Similarity	NPC241341
0.875	High Similarity	NPC229442
0.875	High Similarity	NPC233018
0.875	High Similarity	NPC36437
0.875	High Similarity	NPC168059
0.8742	High Similarity	NPC52740
0.8734	High Similarity	NPC124747
0.8734	High Similarity	NPC155754
0.8734	High Similarity	NPC109061
0.8725	High Similarity	NPC230157
0.8725	High Similarity	NPC6568
0.8725	High Similarity	NPC236419
0.8718	High Similarity	NPC300845
0.8718	High Similarity	NPC104983
0.8718	High Similarity	NPC318432
0.8718	High Similarity	NPC250436
0.8718	High Similarity	NPC291948
0.8718	High Similarity	NPC88803
0.8716	High Similarity	NPC178054
0.8716	High Similarity	NPC471389
0.871	High Similarity	NPC473736
0.8707	High Similarity	NPC25966
0.8707	High Similarity	NPC245207
0.8707	High Similarity	NPC127218
0.8707	High Similarity	NPC319647
0.8699	High Similarity	NPC306441
0.8699	High Similarity	NPC472336
0.8699	High Similarity	NPC471719
0.8699	High Similarity	NPC230734
0.8699	High Similarity	NPC16435
0.8699	High Similarity	NPC227503
0.8699	High Similarity	NPC472334
0.8699	High Similarity	NPC474639
0.8696	High Similarity	NPC243877
0.8696	High Similarity	NPC473818
0.869	High Similarity	NPC135127
0.869	High Similarity	NPC310854
0.869	High Similarity	NPC170694
0.869	High Similarity	NPC106215
0.8681	High Similarity	NPC319969
0.8681	High Similarity	NPC137669
0.8681	High Similarity	NPC137949
0.8681	High Similarity	NPC245120
0.8679	High Similarity	NPC476372
0.8679	High Similarity	NPC55121
0.8679	High Similarity	NPC12326
0.8679	High Similarity	NPC174311
0.8679	High Similarity	NPC476371
0.8667	High Similarity	NPC471824
0.8667	High Similarity	NPC292443
0.8667	High Similarity	NPC232228
0.8658	High Similarity	NPC107161
0.8658	High Similarity	NPC67467
0.8654	High Similarity	NPC125709
0.8654	High Similarity	NPC292385
0.8645	High Similarity	NPC470769
0.8645	High Similarity	NPC78809
0.8645	High Similarity	NPC149735
0.8645	High Similarity	NPC115203
0.8642	High Similarity	NPC280493
0.8636	High Similarity	NPC300329
0.8634	High Similarity	NPC471823
0.863	High Similarity	NPC151224
0.863	High Similarity	NPC260898
0.863	High Similarity	NPC47398
0.863	High Similarity	NPC195022
0.863	High Similarity	NPC61946
0.863	High Similarity	NPC234333

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 NPC120774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	964
0.2-0.3	2026
0.3-0.4	2624
0.4-0.5	1766
0.5-0.6	910
0.6-0.7	311
0.7-0.8	117
0.8-0.85	28
0.85-0.9	20
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD1653	Approved
0.8718	High Similarity	NPD4868	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1613	Approved
0.8425	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD5844	Phase 1
0.8344	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD7549	Discontinued
0.8276	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2801	Approved
0.8219	Intermediate Similarity	NPD3027	Phase 3
0.8214	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7054	Approved
0.8176	Intermediate Similarity	NPD1934	Approved
0.8144	Intermediate Similarity	NPD7472	Approved
0.8092	Intermediate Similarity	NPD7266	Discontinued
0.8075	Intermediate Similarity	NPD3817	Phase 2
0.8036	Intermediate Similarity	NPD7074	Phase 3
0.8027	Intermediate Similarity	NPD4908	Phase 1
0.8012	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD1652	Phase 2
0.7963	Intermediate Similarity	NPD5402	Approved
0.7941	Intermediate Similarity	NPD7251	Discontinued
0.7919	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD422	Phase 1
0.7917	Intermediate Similarity	NPD3818	Discontinued
0.7895	Intermediate Similarity	NPD7808	Phase 3
0.7881	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD5124	Phase 1
0.7818	Intermediate Similarity	NPD6234	Discontinued
0.7811	Intermediate Similarity	NPD7228	Approved
0.7805	Intermediate Similarity	NPD3882	Suspended
0.7785	Intermediate Similarity	NPD1511	Approved
0.7771	Intermediate Similarity	NPD6190	Approved
0.7758	Intermediate Similarity	NPD7075	Discontinued
0.7758	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7199	Phase 2
0.7716	Intermediate Similarity	NPD4380	Phase 2
0.7688	Intermediate Similarity	NPD1512	Approved
0.7679	Intermediate Similarity	NPD6232	Discontinued
0.7669	Intermediate Similarity	NPD7411	Suspended
0.7665	Intermediate Similarity	NPD5494	Approved
0.764	Intermediate Similarity	NPD5403	Approved
0.7639	Intermediate Similarity	NPD1548	Phase 1
0.7633	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6233	Phase 2
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD37	Approved
0.76	Intermediate Similarity	NPD2861	Phase 2
0.7595	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD4967	Phase 2
0.759	Intermediate Similarity	NPD4966	Approved
0.759	Intermediate Similarity	NPD4965	Approved
0.7578	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.7544	Intermediate Similarity	NPD7473	Discontinued
0.7531	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7516	Intermediate Similarity	NPD5401	Approved
0.7515	Intermediate Similarity	NPD6801	Discontinued
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7768	Phase 2
0.7483	Intermediate Similarity	NPD3018	Phase 2
0.7483	Intermediate Similarity	NPD3496	Discontinued
0.747	Intermediate Similarity	NPD7819	Suspended
0.7468	Intermediate Similarity	NPD4060	Phase 1
0.7457	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7213	Phase 3
0.7453	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6799	Approved
0.7453	Intermediate Similarity	NPD7212	Phase 2
0.7451	Intermediate Similarity	NPD6798	Discontinued
0.7425	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD230	Phase 1
0.7412	Intermediate Similarity	NPD6959	Discontinued
0.7412	Intermediate Similarity	NPD8127	Discontinued
0.7407	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7447	Phase 1
0.74	Intermediate Similarity	NPD3225	Approved
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7375	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD8455	Phase 2
0.7358	Intermediate Similarity	NPD1549	Phase 2
0.7342	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2982	Phase 2
0.7333	Intermediate Similarity	NPD2983	Phase 2
0.733	Intermediate Similarity	NPD7240	Approved
0.733	Intermediate Similarity	NPD7685	Pre-registration
0.7325	Intermediate Similarity	NPD7097	Phase 1
0.7312	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6674	Discontinued
0.7308	Intermediate Similarity	NPD447	Suspended
0.7308	Intermediate Similarity	NPD4340	Discontinued
0.7301	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7267	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD2981	Phase 2
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7237	Intermediate Similarity	NPD2797	Approved
0.7235	Intermediate Similarity	NPD3749	Approved
0.7233	Intermediate Similarity	NPD1551	Phase 2
0.7233	Intermediate Similarity	NPD2796	Approved
0.7219	Intermediate Similarity	NPD4749	Approved
0.72	Intermediate Similarity	NPD1091	Approved
0.7193	Intermediate Similarity	NPD919	Approved
0.7186	Intermediate Similarity	NPD6599	Discontinued
0.717	Intermediate Similarity	NPD1510	Phase 2
0.7161	Intermediate Similarity	NPD7095	Approved
0.7158	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD228	Approved
0.7152	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7038	Approved
0.7135	Intermediate Similarity	NPD7039	Approved
0.7134	Intermediate Similarity	NPD4357	Discontinued
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3268	Approved
0.7115	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8054	Approved
0.7111	Intermediate Similarity	NPD8053	Approved
0.7103	Intermediate Similarity	NPD5535	Approved
0.7099	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5536	Phase 2
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD1933	Approved
0.7075	Intermediate Similarity	NPD6671	Approved
0.7066	Intermediate Similarity	NPD3687	Approved
0.7066	Intermediate Similarity	NPD3686	Approved
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD8166	Discontinued
0.7053	Intermediate Similarity	NPD7680	Approved
0.7052	Intermediate Similarity	NPD5677	Discontinued
0.7035	Intermediate Similarity	NPD6971	Discontinued
0.7025	Intermediate Similarity	NPD1558	Phase 1
0.7021	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1247	Approved
0.7005	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6832	Phase 2
0.6982	Remote Similarity	NPD4675	Approved
0.6982	Remote Similarity	NPD4678	Approved
0.6975	Remote Similarity	NPD5762	Approved
0.6975	Remote Similarity	NPD5763	Approved
0.6975	Remote Similarity	NPD3540	Phase 1
0.6971	Remote Similarity	NPD7229	Phase 3
0.6957	Remote Similarity	NPD4308	Phase 3
0.6951	Remote Similarity	NPD4110	Phase 3
0.6951	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5283	Phase 1
0.6936	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2424	Discontinued
0.6932	Remote Similarity	NPD3926	Phase 2
0.6923	Remote Similarity	NPD3226	Approved
0.6919	Remote Similarity	NPD5353	Approved
0.6918	Remote Similarity	NPD4140	Approved
0.6918	Remote Similarity	NPD3620	Phase 2
0.6918	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1240	Approved
0.6915	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6032	Approved
0.6914	Remote Similarity	NPD6100	Approved
0.6914	Remote Similarity	NPD3539	Phase 1
0.6914	Remote Similarity	NPD6099	Approved
0.6903	Remote Similarity	NPD1203	Approved
0.6902	Remote Similarity	NPD6842	Approved
0.6902	Remote Similarity	NPD6843	Phase 3
0.6902	Remote Similarity	NPD6841	Approved
0.6902	Remote Similarity	NPD7906	Approved
0.6899	Remote Similarity	NPD1296	Phase 2
0.6894	Remote Similarity	NPD4536	Approved
0.6894	Remote Similarity	NPD4538	Approved
0.6894	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7783	Phase 2
0.6886	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1358	Approved
0.6875	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1535	Discovery
0.6863	Remote Similarity	NPD3705	Approved
0.6863	Remote Similarity	NPD1611	Approved
0.6859	Remote Similarity	NPD6584	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