NPASS Compound

Structure

NPC471290 OpenBabel07101718292D 24 27 0 0 1 0 0 0 0 0999 V2000 6.0622 -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 0.8660 2.5000 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 5.1962 1.0000 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 5.1962 -0.0000 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 -0.8660 1.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 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 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 11 2 0 0 0 0 7 22 1 0 0 0 0 8 12 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 14 1 0 0 0 0 14 20 2 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.06
Volume:	308.802
LogP:	1.948
LogD:	2.112
LogS:	-4.019
# Rotatable Bonds:	1
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	3.427
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.294
MDCK Permeability:	7.111693776096217e-06
Pgp-inhibitor:	0.598
Pgp-substrate:	0.325
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.553

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	92.30765533447266%
Volume Distribution (VD):	0.701
Pgp-substrate:	7.594542980194092%

ADMET: Metabolism

CYP1A2-inhibitor:	0.845
CYP1A2-substrate:	0.833
CYP2C19-inhibitor:	0.147
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.549
CYP2D6-substrate:	0.319
CYP3A4-inhibitor:	0.209
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	1.647
Half-life (T1/2):	0.671

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.765
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.678
Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.739
Skin Sensitization:	0.156
Carcinogencity:	0.317
Eye Corrosion:	0.004
Eye Irritation:	0.625
Respiratory Toxicity:	0.662

Download Data

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

Natural Product: NPC471290

Natural Product ID:	NPC471290
*Common Name:**	Rac-Boeravinone O
IUPAC Name:	4,6,11-trihydroxy-9-methoxy-6H-chromeno[3,4-b]chromen-12-one
Synonyms:
Standard InCHIKey:	HIHQFLYPSJTPSM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12O7/c1-22-7-5-10(19)13-11(6-7)23-16-12(14(13)20)8-3-2-4-9(18)15(8)24-17(16)21/h2-6,17-19,21H,1H3
SMILES:	COc1cc(O)c2c(c1)oc1c(c2=O)c2cccc(c2OC1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408967
PubChem CID:	71662493
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	roots	n.a.	n.a.	PMID[16792408]
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23914900]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	Inhibition	=	61.2	%	PMID[464850]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	59.9	%	PMID[464850]

☑ 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 NPC471290 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	449
0.1-0.2	1942
0.2-0.3	4490
0.3-0.4	10369
0.4-0.5	7536
0.5-0.6	4010
0.6-0.7	4991
0.7-0.8	5161
0.8-0.85	1887
0.85-0.9	1335
0.9-0.95	521
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC470772
0.9869	High Similarity	NPC470756
0.9682	High Similarity	NPC471288
0.9679	High Similarity	NPC470773
0.9497	High Similarity	NPC471287
0.9474	High Similarity	NPC470771
0.9474	High Similarity	NPC471289
0.9434	High Similarity	NPC229729
0.943	High Similarity	NPC311830
0.943	High Similarity	NPC22832
0.9416	High Similarity	NPC92395
0.9416	High Similarity	NPC87404
0.9379	High Similarity	NPC307518
0.9379	High Similarity	NPC48773
0.9379	High Similarity	NPC205076
0.9375	High Similarity	NPC93337
0.9375	High Similarity	NPC475942
0.9375	High Similarity	NPC58053
0.9375	High Similarity	NPC105025
0.9375	High Similarity	NPC201292
0.9375	High Similarity	NPC186807
0.9375	High Similarity	NPC229687
0.9375	High Similarity	NPC226294
0.9375	High Similarity	NPC469931
0.9375	High Similarity	NPC45638
0.9371	High Similarity	NPC5778
0.9371	High Similarity	NPC236934
0.9367	High Similarity	NPC284960
0.9367	High Similarity	NPC191306
0.9367	High Similarity	NPC19709
0.9367	High Similarity	NPC270335
0.9367	High Similarity	NPC309025
0.9367	High Similarity	NPC222936
0.9367	High Similarity	NPC88023
0.9367	High Similarity	NPC243930
0.9346	High Similarity	NPC471291
0.9317	High Similarity	NPC105511
0.9317	High Similarity	NPC224462
0.9317	High Similarity	NPC21190
0.9317	High Similarity	NPC231194
0.9317	High Similarity	NPC51326
0.9317	High Similarity	NPC183357
0.9317	High Similarity	NPC22195
0.9313	High Similarity	NPC45618
0.9313	High Similarity	NPC58716
0.9313	High Similarity	NPC146792
0.9313	High Similarity	NPC45400
0.9308	High Similarity	NPC165720
0.9304	High Similarity	NPC473043
0.9304	High Similarity	NPC127782
0.9304	High Similarity	NPC300537
0.9304	High Similarity	NPC77660
0.9304	High Similarity	NPC189142
0.9259	High Similarity	NPC117260
0.9259	High Similarity	NPC235575
0.9259	High Similarity	NPC254540
0.9259	High Similarity	NPC476405
0.9259	High Similarity	NPC172807
0.9259	High Similarity	NPC256760
0.9259	High Similarity	NPC211594
0.9255	High Similarity	NPC471457
0.9255	High Similarity	NPC209296
0.9255	High Similarity	NPC219904
0.9255	High Similarity	NPC472383
0.9255	High Similarity	NPC112755
0.9255	High Similarity	NPC472381
0.9255	High Similarity	NPC170675
0.9255	High Similarity	NPC203050
0.9255	High Similarity	NPC195257
0.9255	High Similarity	NPC120099
0.9255	High Similarity	NPC95855
0.9255	High Similarity	NPC223747
0.9255	High Similarity	NPC225434
0.9255	High Similarity	NPC210042
0.925	High Similarity	NPC21100
0.925	High Similarity	NPC197285
0.925	High Similarity	NPC115674
0.925	High Similarity	NPC210073
0.9245	High Similarity	NPC88043
0.9245	High Similarity	NPC168822
0.9245	High Similarity	NPC29830
0.9241	High Similarity	NPC182045
0.9236	High Similarity	NPC184755
0.9236	High Similarity	NPC74178
0.9226	High Similarity	NPC168805
0.9226	High Similarity	NPC121910
0.9221	High Similarity	NPC31363
0.9216	High Similarity	NPC183950
0.9216	High Similarity	NPC40290
0.9216	High Similarity	NPC264550
0.9216	High Similarity	NPC69430
0.9216	High Similarity	NPC137062
0.9216	High Similarity	NPC287101
0.9216	High Similarity	NPC52005
0.9216	High Similarity	NPC195763
0.9216	High Similarity	NPC200060
0.9216	High Similarity	NPC139293
0.9216	High Similarity	NPC223579
0.9216	High Similarity	NPC264289
0.9216	High Similarity	NPC333691
0.9216	High Similarity	NPC142876
0.9202	High Similarity	NPC208668
0.9202	High Similarity	NPC169977
0.9202	High Similarity	NPC21666
0.9202	High Similarity	NPC45522
0.9202	High Similarity	NPC4390
0.9202	High Similarity	NPC204693
0.9202	High Similarity	NPC42773
0.9202	High Similarity	NPC51774
0.9202	High Similarity	NPC101026
0.9202	High Similarity	NPC239549
0.9202	High Similarity	NPC236191
0.9202	High Similarity	NPC24043
0.9198	High Similarity	NPC44558
0.9198	High Similarity	NPC474434
0.9198	High Similarity	NPC79056
0.9198	High Similarity	NPC34287
0.9198	High Similarity	NPC78734
0.9198	High Similarity	NPC471416
0.9198	High Similarity	NPC177731
0.9198	High Similarity	NPC245014
0.9198	High Similarity	NPC84265
0.9198	High Similarity	NPC150767
0.9198	High Similarity	NPC282987
0.9198	High Similarity	NPC212748
0.9198	High Similarity	NPC44328
0.9198	High Similarity	NPC105095
0.9198	High Similarity	NPC206123
0.9193	High Similarity	NPC84362
0.9193	High Similarity	NPC477502
0.9193	High Similarity	NPC223424
0.9193	High Similarity	NPC52550
0.9193	High Similarity	NPC265530
0.9193	High Similarity	NPC226304
0.9193	High Similarity	NPC173637
0.9193	High Similarity	NPC127546
0.9193	High Similarity	NPC116745
0.9193	High Similarity	NPC317489
0.9193	High Similarity	NPC93099
0.9193	High Similarity	NPC135345
0.9193	High Similarity	NPC325555
0.9187	High Similarity	NPC277205
0.9177	High Similarity	NPC110349
0.9172	High Similarity	NPC470402
0.9167	High Similarity	NPC213622
0.9161	High Similarity	NPC39732
0.9161	High Similarity	NPC156222
0.9161	High Similarity	NPC57030
0.9161	High Similarity	NPC241498
0.9161	High Similarity	NPC120163
0.9161	High Similarity	NPC131624
0.9161	High Similarity	NPC25270
0.9161	High Similarity	NPC100887
0.9161	High Similarity	NPC472912
0.9161	High Similarity	NPC71334
0.9161	High Similarity	NPC293183
0.9161	High Similarity	NPC187498
0.9161	High Similarity	NPC477231
0.9161	High Similarity	NPC212678
0.9161	High Similarity	NPC239128
0.9161	High Similarity	NPC219582
0.9161	High Similarity	NPC60972
0.9161	High Similarity	NPC275722
0.9161	High Similarity	NPC162313
0.9161	High Similarity	NPC188203
0.9161	High Similarity	NPC236637
0.9161	High Similarity	NPC260979
0.9161	High Similarity	NPC256283
0.9161	High Similarity	NPC302950
0.9161	High Similarity	NPC83508
0.9161	High Similarity	NPC275836
0.9161	High Similarity	NPC257648
0.9161	High Similarity	NPC198826
0.9161	High Similarity	NPC301323
0.9161	High Similarity	NPC222830
0.9156	High Similarity	NPC29231
0.9152	High Similarity	NPC168584
0.915	High Similarity	NPC254702
0.915	High Similarity	NPC194653
0.915	High Similarity	NPC139364
0.915	High Similarity	NPC119059
0.915	High Similarity	NPC120464
0.915	High Similarity	NPC80710
0.915	High Similarity	NPC203747
0.9146	High Similarity	NPC477848
0.9146	High Similarity	NPC472607
0.9141	High Similarity	NPC472386
0.9141	High Similarity	NPC175107
0.9141	High Similarity	NPC301683
0.9141	High Similarity	NPC259152
0.9141	High Similarity	NPC3583
0.9141	High Similarity	NPC153755
0.9141	High Similarity	NPC267254
0.9141	High Similarity	NPC190003
0.9141	High Similarity	NPC260263
0.9141	High Similarity	NPC261254
0.9136	High Similarity	NPC43587
0.9136	High Similarity	NPC270578
0.9136	High Similarity	NPC86008
0.9136	High Similarity	NPC183036

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 NPC471290 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	423
0.1-0.2	971
0.2-0.3	1952
0.3-0.4	2638
0.4-0.5	1762
0.5-0.6	913
0.6-0.7	329
0.7-0.8	115
0.8-0.85	22
0.85-0.9	18
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9313	High Similarity	NPD3818	Discontinued
0.9255	High Similarity	NPD7054	Approved
0.9198	High Similarity	NPD7074	Phase 3
0.9198	High Similarity	NPD7472	Approved
0.9161	High Similarity	NPD1934	Approved
0.9103	High Similarity	NPD2801	Approved
0.903	High Similarity	NPD4338	Clinical (unspecified phase)
0.9024	High Similarity	NPD6797	Phase 2
0.897	High Similarity	NPD7251	Discontinued
0.8931	High Similarity	NPD4381	Clinical (unspecified phase)
0.8916	High Similarity	NPD7808	Phase 3
0.8889	High Similarity	NPD1511	Approved
0.8868	High Similarity	NPD3882	Suspended
0.8861	High Similarity	NPD2393	Clinical (unspecified phase)
0.8834	High Similarity	NPD6166	Phase 2
0.8834	High Similarity	NPD6167	Clinical (unspecified phase)
0.8834	High Similarity	NPD6168	Clinical (unspecified phase)
0.8774	High Similarity	NPD1512	Approved
0.8688	High Similarity	NPD3817	Phase 2
0.8563	High Similarity	NPD7804	Clinical (unspecified phase)
0.8519	High Similarity	NPD4868	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD4380	Phase 2
0.8377	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD1510	Phase 2
0.8354	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1549	Phase 2
0.8253	Intermediate Similarity	NPD5494	Approved
0.8242	Intermediate Similarity	NPD7075	Discontinued
0.8232	Intermediate Similarity	NPD5402	Approved
0.8221	Intermediate Similarity	NPD6801	Discontinued
0.8198	Intermediate Similarity	NPD6559	Discontinued
0.8194	Intermediate Similarity	NPD2796	Approved
0.8176	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD1465	Phase 2
0.8171	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6232	Discontinued
0.814	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5403	Approved
0.8125	Intermediate Similarity	NPD5401	Approved
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7473	Discontinued
0.8105	Intermediate Similarity	NPD1240	Approved
0.8105	Intermediate Similarity	NPD943	Approved
0.8061	Intermediate Similarity	NPD7819	Suspended
0.8049	Intermediate Similarity	NPD7411	Suspended
0.8025	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1607	Approved
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD7199	Phase 2
0.7987	Intermediate Similarity	NPD3750	Approved
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD919	Approved
0.7975	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD1247	Approved
0.7871	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1613	Approved
0.7866	Intermediate Similarity	NPD1653	Approved
0.784	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD230	Phase 1
0.7811	Intermediate Similarity	NPD3749	Approved
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7685	Pre-registration
0.7778	Intermediate Similarity	NPD6959	Discontinued
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7759	Intermediate Similarity	NPD7228	Approved
0.7751	Intermediate Similarity	NPD7768	Phase 2
0.7746	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1551	Phase 2
0.7727	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1933	Approved
0.7707	Intermediate Similarity	NPD447	Suspended
0.7692	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD37	Approved
0.7677	Intermediate Similarity	NPD3027	Phase 3
0.7673	Intermediate Similarity	NPD3748	Approved
0.7662	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7647	Intermediate Similarity	NPD4965	Approved
0.763	Intermediate Similarity	NPD3787	Discontinued
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8312	Approved
0.7598	Intermediate Similarity	NPD8313	Approved
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2800	Approved
0.759	Intermediate Similarity	NPD920	Approved
0.7576	Intermediate Similarity	NPD2533	Approved
0.7576	Intermediate Similarity	NPD2534	Approved
0.7576	Intermediate Similarity	NPD2532	Approved
0.7548	Intermediate Similarity	NPD9494	Approved
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1243	Approved
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2344	Approved
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7584	Approved
0.7444	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD5953	Discontinued
0.7407	Intermediate Similarity	NPD6782	Approved
0.7407	Intermediate Similarity	NPD6778	Approved
0.7407	Intermediate Similarity	NPD6781	Approved
0.7407	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6780	Approved
0.7407	Intermediate Similarity	NPD6777	Approved
0.7407	Intermediate Similarity	NPD6779	Approved
0.7407	Intermediate Similarity	NPD6776	Approved
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7396	Intermediate Similarity	NPD3226	Approved
0.7394	Intermediate Similarity	NPD6190	Approved
0.7372	Intermediate Similarity	NPD2798	Approved
0.7371	Intermediate Similarity	NPD8151	Discontinued
0.7362	Intermediate Similarity	NPD7266	Discontinued
0.7346	Intermediate Similarity	NPD7033	Discontinued
0.7346	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2799	Discontinued
0.734	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7286	Phase 2
0.7308	Intermediate Similarity	NPD1203	Approved
0.7301	Intermediate Similarity	NPD6100	Approved
0.7301	Intermediate Similarity	NPD6099	Approved
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7293	Intermediate Similarity	NPD7240	Approved
0.7292	Intermediate Similarity	NPD7435	Discontinued
0.729	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD4908	Phase 1
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2346	Discontinued
0.7244	Intermediate Similarity	NPD3225	Approved
0.7237	Intermediate Similarity	NPD1548	Phase 1
0.7225	Intermediate Similarity	NPD8455	Phase 2
0.7222	Intermediate Similarity	NPD6651	Approved
0.7208	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7783	Phase 2
0.7202	Intermediate Similarity	NPD7698	Approved
0.7202	Intermediate Similarity	NPD7696	Phase 3
0.7202	Intermediate Similarity	NPD7697	Approved
0.7191	Intermediate Similarity	NPD5242	Approved
0.7188	Intermediate Similarity	NPD3268	Approved
0.7188	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7165	Intermediate Similarity	NPD7871	Phase 2
0.7165	Intermediate Similarity	NPD7870	Phase 2
0.7161	Intermediate Similarity	NPD1610	Phase 2
0.7161	Intermediate Similarity	NPD422	Phase 1
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD6535	Approved
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD9269	Phase 2
0.7115	Intermediate Similarity	NPD1608	Approved
0.7115	Intermediate Similarity	NPD9717	Approved
0.7101	Intermediate Similarity	NPD7390	Discontinued
0.7097	Intermediate Similarity	NPD8434	Phase 2
0.7089	Intermediate Similarity	NPD2797	Approved
0.7086	Intermediate Similarity	NPD4288	Approved
0.7081	Intermediate Similarity	NPD6798	Discontinued
0.7081	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7874	Approved
0.7071	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6844	Discontinued
0.7066	Intermediate Similarity	NPD6674	Discontinued
0.7059	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7585	Approved
0.7056	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5710	Approved
0.7039	Intermediate Similarity	NPD5711	Approved
0.7035	Intermediate Similarity	NPD7801	Approved
0.7031	Intermediate Similarity	NPD7699	Phase 2
0.7031	Intermediate Similarity	NPD7700	Phase 2
0.7016	Intermediate Similarity	NPD4361	Phase 2
0.7016	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6385	Approved
0.7011	Intermediate Similarity	NPD6386	Approved
0.7005	Intermediate Similarity	NPD8150	Discontinued
0.7005	Intermediate Similarity	NPD7583	Approved
0.6995	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5353	Approved
0.6981	Remote Similarity	NPD3266	Approved
0.6981	Remote Similarity	NPD3267	Approved
0.6975	Remote Similarity	NPD411	Approved
0.6964	Remote Similarity	NPD1652	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