NPASS Compound

Structure

NPC30688 OpenBabel07101719252D 31 34 0 0 1 0 0 0 0 0999 V2000 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 1.5000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 4.3301 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 0.8660 0.5000 0.0000 C 0 0 2 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 1.7321 -0.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 2.0000 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 -1.7321 -1.0000 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 11 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 28 1 0 0 0 0 11 23 2 0 0 0 0 11 28 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 10 1 6 0 0 0 17 19 1 0 0 0 0 17 29 1 0 0 0 0 18 25 2 0 0 0 0 18 30 1 0 0 0 0 19 12 1 1 0 0 0 19 31 1 0 0 0 0 20 22 2 0 0 0 0 20 30 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.11
Volume:	410.226
LogP:	2.15
LogD:	2.242
LogS:	-4.519
# Rotatable Bonds:	6
TPSA:	113.66
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	3.516
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.774
MDCK Permeability:	3.381081114639528e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.388
Plasma Protein Binding (PPB):	80.01457214355469%
Volume Distribution (VD):	0.811
Pgp-substrate:	18.101398468017578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.268
CYP1A2-substrate:	0.82
CYP2C19-inhibitor:	0.538
CYP2C19-substrate:	0.143
CYP2C9-inhibitor:	0.797
CYP2C9-substrate:	0.815
CYP2D6-inhibitor:	0.672
CYP2D6-substrate:	0.523
CYP3A4-inhibitor:	0.715
CYP3A4-substrate:	0.682

ADMET: Excretion

Clearance (CL):	3.31
Half-life (T1/2):	0.718

ADMET: Toxicity

hERG Blockers:	0.187
Human Hepatotoxicity (H-HT):	0.821
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.221
Rat Oral Acute Toxicity:	0.407
Maximum Recommended Daily Dose:	0.265
Skin Sensitization:	0.371
Carcinogencity:	0.658
Eye Corrosion:	0.003
Eye Irritation:	0.116
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC30688

Natural Product ID:	NPC30688
*Common Name:**	Durantin A
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 acetate
Synonyms:
Standard InCHIKey:	ICLAWMWLMZMRGC-IEBWSBKVSA-N
Standard InCHI:	InChI=1S/C22H20O9/c1-11(23)28-10-17-19(12-4-6-14(24)15(8-12)26-2)31-21-16(27-3)9-13-5-7-18(25)30-20(13)22(21)29-17/h4-9,17,19,24H,10H2,1-3H3/t17-,19-/m1/s1
SMILES:	COc1cc2ccc(=O)oc2c2c1O[C@@H]([C@H](O2)COC(=O)C)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495830
PubChem CID:	11224109
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
Others	6

Activity Type	# Activity
NON-MOLECULAR	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	625000.0	nM	PMID[471364]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	73.3	%	PMID[471365]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	76.25	%	PMID[471365]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	81.88	%	PMID[471365]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	78.3	%	PMID[471365]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	109.32	%	PMID[471365]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	74.84	%	PMID[471365]

☑ 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 NPC30688 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	405
0.1-0.2	1840
0.2-0.3	4955
0.3-0.4	10161
0.4-0.5	7416
0.5-0.6	4016
0.6-0.7	5318
0.7-0.8	4921
0.8-0.85	1906
0.85-0.9	1442
0.9-0.95	293
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC176903
0.993	High Similarity	NPC120426
0.993	High Similarity	NPC294522
0.993	High Similarity	NPC21184
0.993	High Similarity	NPC205727
0.9792	High Similarity	NPC264875
0.9792	High Similarity	NPC120774
0.9792	High Similarity	NPC163598
0.9789	High Similarity	NPC476348
0.9789	High Similarity	NPC187398
0.9718	High Similarity	NPC15577
0.9718	High Similarity	NPC476347
0.9437	High Similarity	NPC34245
0.9437	High Similarity	NPC110067
0.9437	High Similarity	NPC7439
0.9437	High Similarity	NPC256555
0.9437	High Similarity	NPC91492
0.9375	High Similarity	NPC40222
0.9375	High Similarity	NPC268515
0.9324	High Similarity	NPC150442
0.932	High Similarity	NPC213197
0.931	High Similarity	NPC231149
0.9291	High Similarity	NPC13067
0.9262	High Similarity	NPC8712
0.9257	High Similarity	NPC176186
0.9257	High Similarity	NPC169404
0.9257	High Similarity	NPC53587
0.9247	High Similarity	NPC48366
0.9247	High Similarity	NPC139839
0.922	High Similarity	NPC95162
0.922	High Similarity	NPC76336
0.922	High Similarity	NPC20511
0.922	High Similarity	NPC139548
0.922	High Similarity	NPC148835
0.922	High Similarity	NPC52086
0.9184	High Similarity	NPC313334
0.9184	High Similarity	NPC212670
0.9184	High Similarity	NPC206264
0.9178	High Similarity	NPC178129
0.9161	High Similarity	NPC300611
0.9155	High Similarity	NPC164148
0.9155	High Similarity	NPC43500
0.9149	High Similarity	NPC82271
0.9149	High Similarity	NPC126682
0.9128	High Similarity	NPC476352
0.9128	High Similarity	NPC215060
0.9122	High Similarity	NPC114740
0.9116	High Similarity	NPC478237
0.9116	High Similarity	NPC93924
0.9116	High Similarity	NPC96294
0.911	High Similarity	NPC205361
0.9103	High Similarity	NPC185127
0.9097	High Similarity	NPC193722
0.9097	High Similarity	NPC278469
0.9097	High Similarity	NPC142614
0.9085	High Similarity	NPC102904
0.9085	High Similarity	NPC176051
0.9085	High Similarity	NPC107551
0.9085	High Similarity	NPC126206
0.9085	High Similarity	NPC103976
0.9085	High Similarity	NPC474886
0.9085	High Similarity	NPC326797
0.9085	High Similarity	NPC38874
0.9085	High Similarity	NPC474282
0.9054	High Similarity	NPC475250
0.9054	High Similarity	NPC106138
0.9048	High Similarity	NPC41844
0.9034	High Similarity	NPC138212
0.9028	High Similarity	NPC83375
0.9028	High Similarity	NPC224876
0.9014	High Similarity	NPC471664
0.9014	High Similarity	NPC471665
0.9014	High Similarity	NPC286843
0.9013	High Similarity	NPC284810
0.9007	High Similarity	NPC474600
0.9007	High Similarity	NPC268484
0.9007	High Similarity	NPC92830
0.9007	High Similarity	NPC111635
0.9007	High Similarity	NPC309953
0.898	High Similarity	NPC199928
0.8973	High Similarity	NPC471763
0.8966	High Similarity	NPC469564
0.8958	High Similarity	NPC267291
0.8951	High Similarity	NPC211549
0.8951	High Similarity	NPC276490
0.8944	High Similarity	NPC112246
0.8944	High Similarity	NPC472337
0.8944	High Similarity	NPC470356
0.8944	High Similarity	NPC474206
0.8944	High Similarity	NPC94750
0.8944	High Similarity	NPC234865
0.8944	High Similarity	NPC121812
0.8944	High Similarity	NPC311430
0.8944	High Similarity	NPC224941
0.8944	High Similarity	NPC112939
0.894	High Similarity	NPC223720
0.8936	High Similarity	NPC26673
0.8936	High Similarity	NPC241341
0.8936	High Similarity	NPC168059
0.8936	High Similarity	NPC229442
0.8936	High Similarity	NPC36437
0.8936	High Similarity	NPC233018
0.8936	High Similarity	NPC277021
0.8919	High Similarity	NPC275125
0.8919	High Similarity	NPC97937
0.8919	High Similarity	NPC52740
0.8919	High Similarity	NPC170239
0.8904	High Similarity	NPC6568
0.8904	High Similarity	NPC230157
0.8904	High Similarity	NPC236419
0.8897	High Similarity	NPC471389
0.8889	High Similarity	NPC245207
0.8889	High Similarity	NPC127218
0.8889	High Similarity	NPC319647
0.8889	High Similarity	NPC25966
0.8882	High Similarity	NPC7178
0.8882	High Similarity	NPC62903
0.8881	High Similarity	NPC16435
0.8881	High Similarity	NPC227503
0.8881	High Similarity	NPC472336
0.8881	High Similarity	NPC306441
0.8881	High Similarity	NPC471719
0.8881	High Similarity	NPC472334
0.8881	High Similarity	NPC230734
0.8881	High Similarity	NPC474639
0.8873	High Similarity	NPC135127
0.8873	High Similarity	NPC170694
0.8873	High Similarity	NPC106215
0.8873	High Similarity	NPC310854
0.8865	High Similarity	NPC137669
0.8865	High Similarity	NPC137949
0.8865	High Similarity	NPC319969
0.8865	High Similarity	NPC245120
0.8844	High Similarity	NPC232228
0.8844	High Similarity	NPC292443
0.8844	High Similarity	NPC471824
0.8839	High Similarity	NPC53889
0.8836	High Similarity	NPC107161
0.8831	High Similarity	NPC125495
0.8824	High Similarity	NPC142479
0.8824	High Similarity	NPC155015
0.8816	High Similarity	NPC149735
0.8816	High Similarity	NPC474656
0.8811	High Similarity	NPC260898
0.8811	High Similarity	NPC234333
0.8811	High Similarity	NPC61946
0.8811	High Similarity	NPC47398
0.8811	High Similarity	NPC151224
0.8811	High Similarity	NPC195022
0.8803	High Similarity	NPC11060
0.8803	High Similarity	NPC474810
0.88	High Similarity	NPC113790
0.8794	High Similarity	NPC73738
0.8792	High Similarity	NPC21776
0.8792	High Similarity	NPC16269
0.8792	High Similarity	NPC227902
0.8784	High Similarity	NPC473909
0.8784	High Similarity	NPC274960
0.8784	High Similarity	NPC125617
0.8784	High Similarity	NPC226722
0.8784	High Similarity	NPC143120
0.8776	High Similarity	NPC478239
0.8776	High Similarity	NPC252169
0.8774	High Similarity	NPC87317
0.8767	High Similarity	NPC247291
0.8767	High Similarity	NPC472520
0.8767	High Similarity	NPC279851
0.8759	High Similarity	NPC270256
0.8759	High Similarity	NPC471388
0.875	High Similarity	NPC162659
0.875	High Similarity	NPC173660
0.875	High Similarity	NPC269091
0.875	High Similarity	NPC265433
0.875	High Similarity	NPC302701
0.875	High Similarity	NPC270456
0.875	High Similarity	NPC248727
0.8741	High Similarity	NPC309744
0.8741	High Similarity	NPC317380
0.8733	High Similarity	NPC175976
0.8733	High Similarity	NPC102934
0.8733	High Similarity	NPC252402
0.8733	High Similarity	NPC281549
0.8732	High Similarity	NPC127624
0.8732	High Similarity	NPC7903
0.8732	High Similarity	NPC184447
0.8732	High Similarity	NPC86655
0.8732	High Similarity	NPC160991
0.8732	High Similarity	NPC5423
0.8732	High Similarity	NPC202762
0.8732	High Similarity	NPC16208
0.8732	High Similarity	NPC35932
0.8725	High Similarity	NPC125755
0.8725	High Similarity	NPC287275
0.8723	High Similarity	NPC214860
0.8723	High Similarity	NPC19242
0.8723	High Similarity	NPC240722
0.8723	High Similarity	NPC91291
0.8723	High Similarity	NPC476399
0.8723	High Similarity	NPC244799
0.8718	High Similarity	NPC24164

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 NPC30688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	983
0.2-0.3	2055
0.3-0.4	2588
0.4-0.5	1735
0.5-0.6	924
0.6-0.7	331
0.7-0.8	106
0.8-0.85	31
0.85-0.9	20
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9184	High Similarity	NPD1653	Approved
0.8645	High Similarity	NPD4868	Clinical (unspecified phase)
0.8601	High Similarity	NPD1612	Clinical (unspecified phase)
0.8601	High Similarity	NPD1613	Approved
0.8451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD2801	Approved
0.8392	Intermediate Similarity	NPD3027	Phase 3
0.838	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD1934	Approved
0.8255	Intermediate Similarity	NPD7266	Discontinued
0.8232	Intermediate Similarity	NPD7054	Approved
0.8228	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD7472	Approved
0.8165	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1465	Phase 2
0.816	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6166	Phase 2
0.8146	Intermediate Similarity	NPD1652	Phase 2
0.8144	Intermediate Similarity	NPD7549	Discontinued
0.8113	Intermediate Similarity	NPD5402	Approved
0.8085	Intermediate Similarity	NPD422	Phase 1
0.8072	Intermediate Similarity	NPD7074	Phase 3
0.8061	Intermediate Similarity	NPD3818	Discontinued
0.8041	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5124	Phase 1
0.8024	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6797	Phase 2
0.7976	Intermediate Similarity	NPD7251	Discontinued
0.795	Intermediate Similarity	NPD3882	Suspended
0.7945	Intermediate Similarity	NPD4908	Phase 1
0.7935	Intermediate Similarity	NPD1511	Approved
0.7929	Intermediate Similarity	NPD7808	Phase 3
0.7901	Intermediate Similarity	NPD7075	Discontinued
0.7901	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4380	Phase 2
0.7853	Intermediate Similarity	NPD6234	Discontinued
0.7838	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1512	Approved
0.7806	Intermediate Similarity	NPD6190	Approved
0.7805	Intermediate Similarity	NPD5494	Approved
0.7801	Intermediate Similarity	NPD1548	Phase 1
0.7785	Intermediate Similarity	NPD5403	Approved
0.7755	Intermediate Similarity	NPD2861	Phase 2
0.7742	Intermediate Similarity	NPD3750	Approved
0.7738	Intermediate Similarity	NPD7228	Approved
0.7724	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1610	Phase 2
0.7658	Intermediate Similarity	NPD5401	Approved
0.7654	Intermediate Similarity	NPD37	Approved
0.7654	Intermediate Similarity	NPD6801	Discontinued
0.7651	Intermediate Similarity	NPD7199	Phase 2
0.7639	Intermediate Similarity	NPD3496	Discontinued
0.7635	Intermediate Similarity	NPD3018	Phase 2
0.7622	Intermediate Similarity	NPD4965	Approved
0.7622	Intermediate Similarity	NPD4967	Phase 2
0.7622	Intermediate Similarity	NPD4966	Approved
0.7616	Intermediate Similarity	NPD4060	Phase 1
0.7607	Intermediate Similarity	NPD7819	Suspended
0.7605	Intermediate Similarity	NPD6232	Discontinued
0.7595	Intermediate Similarity	NPD6799	Approved
0.7593	Intermediate Similarity	NPD7411	Suspended
0.7586	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD230	Phase 1
0.756	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6559	Discontinued
0.7551	Intermediate Similarity	NPD3225	Approved
0.755	Intermediate Similarity	NPD6233	Phase 2
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1549	Phase 2
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD2982	Phase 2
0.7483	Intermediate Similarity	NPD2983	Phase 2
0.7471	Intermediate Similarity	NPD7473	Discontinued
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7685	Pre-registration
0.7453	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD447	Suspended
0.7451	Intermediate Similarity	NPD4340	Discontinued
0.744	Intermediate Similarity	NPD8127	Discontinued
0.7438	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3748	Approved
0.7417	Intermediate Similarity	NPD4625	Phase 3
0.7415	Intermediate Similarity	NPD2981	Phase 2
0.741	Intermediate Similarity	NPD7768	Phase 2
0.7405	Intermediate Similarity	NPD4628	Phase 3
0.7383	Intermediate Similarity	NPD2797	Approved
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1551	Phase 2
0.7372	Intermediate Similarity	NPD2796	Approved
0.7368	Intermediate Similarity	NPD6798	Discontinued
0.7365	Intermediate Similarity	NPD4749	Approved
0.7349	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1091	Approved
0.7342	Intermediate Similarity	NPD6674	Discontinued
0.7329	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3751	Discontinued
0.7321	Intermediate Similarity	NPD919	Approved
0.7317	Intermediate Similarity	NPD6599	Discontinued
0.731	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1510	Phase 2
0.7305	Intermediate Similarity	NPD228	Approved
0.7284	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7213	Phase 3
0.7267	Intermediate Similarity	NPD7212	Phase 2
0.7267	Intermediate Similarity	NPD4357	Discontinued
0.7257	Intermediate Similarity	NPD7240	Approved
0.7255	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3268	Approved
0.7244	Intermediate Similarity	NPD7097	Phase 1
0.7241	Intermediate Similarity	NPD5536	Phase 2
0.7237	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6959	Discontinued
0.7233	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD1933	Approved
0.7222	Intermediate Similarity	NPD6671	Approved
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7447	Phase 1
0.7197	Intermediate Similarity	NPD7033	Discontinued
0.7195	Intermediate Similarity	NPD3687	Approved
0.7195	Intermediate Similarity	NPD3686	Approved
0.7193	Intermediate Similarity	NPD3787	Discontinued
0.719	Intermediate Similarity	NPD7095	Approved
0.7186	Intermediate Similarity	NPD8455	Phase 2
0.7176	Intermediate Similarity	NPD5677	Discontinued
0.7161	Intermediate Similarity	NPD1558	Phase 1
0.716	Intermediate Similarity	NPD3749	Approved
0.7152	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1247	Approved
0.7133	Intermediate Similarity	NPD5535	Approved
0.7124	Intermediate Similarity	NPD6832	Phase 2
0.712	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4675	Approved
0.7108	Intermediate Similarity	NPD4678	Approved
0.7107	Intermediate Similarity	NPD5762	Approved
0.7107	Intermediate Similarity	NPD3540	Phase 1
0.7107	Intermediate Similarity	NPD5763	Approved
0.7089	Intermediate Similarity	NPD4308	Phase 3
0.7088	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5283	Phase 1
0.7081	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4110	Phase 3
0.7063	Intermediate Similarity	NPD2424	Discontinued
0.7062	Intermediate Similarity	NPD7039	Approved
0.7062	Intermediate Similarity	NPD7038	Approved
0.7059	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1240	Approved
0.7048	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6099	Approved
0.7044	Intermediate Similarity	NPD6100	Approved
0.7044	Intermediate Similarity	NPD6032	Approved
0.7044	Intermediate Similarity	NPD3539	Phase 1
0.7041	Intermediate Similarity	NPD5353	Approved
0.7039	Intermediate Similarity	NPD1203	Approved
0.7032	Intermediate Similarity	NPD1296	Phase 2
0.7025	Intermediate Similarity	NPD4536	Approved
0.7025	Intermediate Similarity	NPD4538	Approved
0.7025	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1358	Approved
0.7017	Intermediate Similarity	NPD6843	Phase 3
0.7017	Intermediate Similarity	NPD6841	Approved
0.7017	Intermediate Similarity	NPD6842	Approved
0.7006	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1535	Discovery
0.7	Intermediate Similarity	NPD1611	Approved
0.7	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3705	Approved
0.6987	Remote Similarity	NPD4062	Phase 3
0.6983	Remote Similarity	NPD8312	Approved
0.6983	Remote Similarity	NPD8313	Approved
0.698	Remote Similarity	NPD4626	Approved
0.698	Remote Similarity	NPD1778	Approved
0.6975	Remote Similarity	NPD8166	Discontinued
0.6962	Remote Similarity	NPD1607	Approved
0.6962	Remote Similarity	NPD6653	Approved
0.6959	Remote Similarity	NPD6971	Discontinued
0.6954	Remote Similarity	NPD3926	Phase 2
0.6954	Remote Similarity	NPD5242	Approved
0.6954	Remote Similarity	NPD1481	Phase 2
0.6952	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.695	Remote Similarity	NPD968	Approved
0.6948	Remote Similarity	NPD9494	Approved
0.6946	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3226	Approved
0.6944	Remote Similarity	NPD8053	Approved
0.6944	Remote Similarity	NPD8054	Approved
0.6943	Remote Similarity	NPD943	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