NPASS Compound

Structure

NPC470448 OpenBabel07101719252D 43 47 0 0 1 0 0 0 0 0999 V2000 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 0.8660 1.5000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 4.3301 2.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 2 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 2 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 -3.4641 0.0000 0.0000 C 0 0 2 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 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 3.4641 4.0000 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 8 1 0 0 0 0 2 38 1 0 0 0 0 3 8 2 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 9 1 0 0 0 0 5 12 2 0 0 0 0 6 28 1 0 0 0 0 7 39 1 0 0 0 0 8 40 1 0 0 0 0 9 29 1 0 0 0 0 10 16 2 0 0 0 0 10 24 1 0 0 0 0 11 15 1 0 0 0 0 11 24 2 0 0 0 0 12 15 1 0 0 0 0 12 41 1 0 0 0 0 13 6 1 6 0 0 0 13 17 1 0 0 0 0 13 42 1 0 0 0 0 14 7 1 1 0 0 0 14 18 1 0 0 0 0 14 43 1 0 0 0 0 15 19 2 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 30 1 1 0 0 0 18 21 1 0 0 0 0 18 31 1 6 0 0 0 19 32 1 0 0 0 0 20 22 1 0 0 0 0 20 33 1 6 0 0 0 21 23 1 0 0 0 0 21 34 1 1 0 0 0 22 26 1 0 0 0 0 22 35 1 1 0 0 0 23 27 1 0 0 0 0 23 36 1 6 0 0 0 24 38 1 0 0 0 0 25 37 2 0 0 0 0 25 40 1 0 0 0 0 26 39 1 6 0 0 0 26 42 1 0 0 0 0 27 41 1 1 0 0 0 27 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.17
Volume:	554.954
LogP:	-0.486
LogD:	-0.443
LogS:	-2.524
# Rotatable Bonds:	7
TPSA:	258.43
# H-Bond Aceptor:	16
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.127
Synthetic Accessibility Score:	5.1
Fsp3:	0.519
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.542
MDCK Permeability:	3.710910095833242e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.88
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	66.67398071289062%
Volume Distribution (VD):	0.606
Pgp-substrate:	21.917245864868164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.135
Half-life (T1/2):	0.636

ADMET: Toxicity

hERG Blockers:	0.181
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.553
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.244
Carcinogencity:	0.161
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC470448

Natural Product ID:	NPC470448
*Common Name:**	7,9,10-Trihydroxy-5-Methoxy-3-Methyl-1H-Naphtho[2,3-C]Pyran-1-One-9-O-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	7,10-dihydroxy-5-methoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzo[g]isochromen-1-one
Synonyms:
Standard InCHIKey:	LTXGXYWAIVIDEM-QEKRRRGYSA-N
Standard InCHI:	InChI=1S/C27H32O16/c1-8-3-10-16(25(37)40-8)19(32)15-11(24(10)38-2)4-9(29)5-12(15)41-27-23(36)21(34)18(31)14(43-27)7-39-26-22(35)20(33)17(30)13(6-28)42-26/h3-5,13-14,17-18,20-23,26-36H,6-7H2,1-2H3/t13-,14-,17-,18-,20+,21+,22-,23-,26-,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3cc(O)cc4c3c(O)c3c(c4OC)cc(oc3=O)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2037051
PubChem CID:	57409959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones [CHEMONTID:0001646] Naphthopyranone glycosides

*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
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	Flowers	Santana do Riacho, State Minas Gerais, Brazil	n.a.	PMID[22506638]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.038	mM	PMID[490434]

☑ 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 NPC470448 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	437
0.1-0.2	1910
0.2-0.3	3854
0.3-0.4	9078
0.4-0.5	8928
0.5-0.6	5366
0.6-0.7	5580
0.7-0.8	5737
0.8-0.85	1309
0.85-0.9	465
0.9-0.95	23
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470453
1.0	High Similarity	NPC470452
1.0	High Similarity	NPC164047
0.994	High Similarity	NPC84494
0.994	High Similarity	NPC245059
0.9759	High Similarity	NPC470454
0.9759	High Similarity	NPC199533
0.9759	High Similarity	NPC63105
0.9581	High Similarity	NPC213052
0.9415	High Similarity	NPC475161
0.9415	High Similarity	NPC477860
0.9401	High Similarity	NPC259905
0.9364	High Similarity	NPC241847
0.9353	High Similarity	NPC46958
0.9345	High Similarity	NPC298778
0.9294	High Similarity	NPC68381
0.9281	High Similarity	NPC178851
0.9253	High Similarity	NPC221140
0.9253	High Similarity	NPC475352
0.9253	High Similarity	NPC473686
0.9253	High Similarity	NPC87583
0.9253	High Similarity	NPC475220
0.9253	High Similarity	NPC229817
0.924	High Similarity	NPC475246
0.9231	High Similarity	NPC210808
0.9231	High Similarity	NPC199079
0.9226	High Similarity	NPC249977
0.9181	High Similarity	NPC3718
0.9181	High Similarity	NPC474345
0.9176	High Similarity	NPC9002
0.9176	High Similarity	NPC271385
0.9176	High Similarity	NPC288152
0.9176	High Similarity	NPC30432
0.9176	High Similarity	NPC257011
0.9176	High Similarity	NPC76128
0.9176	High Similarity	NPC137871
0.9176	High Similarity	NPC111536
0.9176	High Similarity	NPC5029
0.9162	High Similarity	NPC17432
0.9153	High Similarity	NPC48474
0.9138	High Similarity	NPC293227
0.9138	High Similarity	NPC473717
0.9138	High Similarity	NPC475662
0.9138	High Similarity	NPC473631
0.9133	High Similarity	NPC299149
0.9133	High Similarity	NPC277710
0.9133	High Similarity	NPC153578
0.9133	High Similarity	NPC114257
0.9107	High Similarity	NPC99216
0.9107	High Similarity	NPC7752
0.9106	High Similarity	NPC470198
0.9106	High Similarity	NPC282474
0.9106	High Similarity	NPC470200
0.9106	High Similarity	NPC470194
0.9106	High Similarity	NPC470195
0.9106	High Similarity	NPC316274
0.9106	High Similarity	NPC470197
0.9106	High Similarity	NPC470193
0.9106	High Similarity	NPC470196
0.9059	High Similarity	NPC473202
0.9053	High Similarity	NPC70441
0.9048	High Similarity	NPC124155
0.9048	High Similarity	NPC257566
0.9045	High Similarity	NPC264302
0.9045	High Similarity	NPC321046
0.9017	High Similarity	NPC102053
0.9017	High Similarity	NPC475233
0.9012	High Similarity	NPC472054
0.9012	High Similarity	NPC25724
0.9006	High Similarity	NPC241874
0.9006	High Similarity	NPC477572
0.9006	High Similarity	NPC477571
0.9006	High Similarity	NPC477573
0.9	High Similarity	NPC314687
0.8994	High Similarity	NPC314459
0.8994	High Similarity	NPC470199
0.8989	High Similarity	NPC314672
0.8989	High Similarity	NPC472721
0.8989	High Similarity	NPC31208
0.8989	High Similarity	NPC469652
0.8989	High Similarity	NPC472724
0.8989	High Similarity	NPC160543
0.8989	High Similarity	NPC93065
0.8989	High Similarity	NPC472720
0.8988	High Similarity	NPC44947
0.8988	High Similarity	NPC216752
0.8988	High Similarity	NPC298171
0.8983	High Similarity	NPC105591
0.8982	High Similarity	NPC328093
0.8977	High Similarity	NPC148710
0.8977	High Similarity	NPC49690
0.8976	High Similarity	NPC257309
0.896	High Similarity	NPC102028
0.8956	High Similarity	NPC131405
0.8956	High Similarity	NPC174140
0.8953	High Similarity	NPC472386
0.8947	High Similarity	NPC222455
0.8947	High Similarity	NPC246274
0.8933	High Similarity	NPC223534
0.8933	High Similarity	NPC158214
0.8933	High Similarity	NPC240200
0.8933	High Similarity	NPC290289
0.8929	High Similarity	NPC101636
0.8929	High Similarity	NPC47923
0.8927	High Similarity	NPC111490
0.8927	High Similarity	NPC261623
0.892	High Similarity	NPC470446
0.892	High Similarity	NPC470445
0.892	High Similarity	NPC470449
0.892	High Similarity	NPC470447
0.8914	High Similarity	NPC58538
0.8914	High Similarity	NPC212290
0.8908	High Similarity	NPC255799
0.8908	High Similarity	NPC312630
0.8908	High Similarity	NPC324220
0.8902	High Similarity	NPC203751
0.8902	High Similarity	NPC98776
0.8902	High Similarity	NPC208668
0.8902	High Similarity	NPC85368
0.8902	High Similarity	NPC204693
0.8895	High Similarity	NPC78734
0.8895	High Similarity	NPC52353
0.8895	High Similarity	NPC313304
0.8895	High Similarity	NPC76047
0.8895	High Similarity	NPC150767
0.8895	High Similarity	NPC218488
0.8883	High Similarity	NPC187632
0.8876	High Similarity	NPC260521
0.8876	High Similarity	NPC469649
0.8876	High Similarity	NPC190450
0.887	High Similarity	NPC224557
0.887	High Similarity	NPC470451
0.887	High Similarity	NPC75574
0.887	High Similarity	NPC470455
0.887	High Similarity	NPC292706
0.8869	High Similarity	NPC470358
0.8857	High Similarity	NPC472387
0.8857	High Similarity	NPC477683
0.8857	High Similarity	NPC477682
0.8851	High Similarity	NPC146803
0.8851	High Similarity	NPC142996
0.8844	High Similarity	NPC267254
0.8844	High Similarity	NPC259152
0.8844	High Similarity	NPC256760
0.8844	High Similarity	NPC254540
0.8844	High Similarity	NPC475155
0.8844	High Similarity	NPC156977
0.8844	High Similarity	NPC3583
0.8844	High Similarity	NPC211594
0.8844	High Similarity	NPC172807
0.8844	High Similarity	NPC315619
0.8844	High Similarity	NPC301683
0.884	High Similarity	NPC477082
0.8837	High Similarity	NPC472381
0.8837	High Similarity	NPC5319
0.8837	High Similarity	NPC472383
0.8833	High Similarity	NPC471091
0.8833	High Similarity	NPC478034
0.8833	High Similarity	NPC97924
0.8833	High Similarity	NPC40078
0.883	High Similarity	NPC298666
0.883	High Similarity	NPC178173
0.883	High Similarity	NPC64425
0.883	High Similarity	NPC68592
0.883	High Similarity	NPC262222
0.8827	High Similarity	NPC477083
0.8827	High Similarity	NPC473618
0.8827	High Similarity	NPC477081
0.882	High Similarity	NPC469650
0.8817	High Similarity	NPC303913
0.8814	High Similarity	NPC313452
0.881	High Similarity	NPC22062
0.881	High Similarity	NPC473634
0.881	High Similarity	NPC138811
0.8807	High Similarity	NPC241423
0.8807	High Similarity	NPC470444
0.8807	High Similarity	NPC470443
0.8807	High Similarity	NPC126784
0.8807	High Similarity	NPC473682
0.8807	High Similarity	NPC110941
0.8807	High Similarity	NPC473571
0.8802	High Similarity	NPC261866
0.88	High Similarity	NPC470949
0.88	High Similarity	NPC169733
0.88	High Similarity	NPC314489
0.88	High Similarity	NPC471669
0.88	High Similarity	NPC289876
0.88	High Similarity	NPC232818
0.88	High Similarity	NPC472380
0.88	High Similarity	NPC472382
0.88	High Similarity	NPC472384
0.88	High Similarity	NPC89127
0.88	High Similarity	NPC297574
0.88	High Similarity	NPC65563
0.88	High Similarity	NPC198893
0.8793	High Similarity	NPC263119
0.8793	High Similarity	NPC239549
0.8793	High Similarity	NPC166674
0.8793	High Similarity	NPC51774
0.8793	High Similarity	NPC473550

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 NPC470448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	995
0.2-0.3	1984
0.3-0.4	2719
0.4-0.5	1858
0.5-0.6	801
0.6-0.7	248
0.7-0.8	121
0.8-0.85	19
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8837	High Similarity	NPD7804	Clinical (unspecified phase)
0.8786	High Similarity	NPD7472	Approved
0.8771	High Similarity	NPD7879	Clinical (unspecified phase)
0.8728	High Similarity	NPD7054	Approved
0.8693	High Similarity	NPD8312	Approved
0.8693	High Similarity	NPD8313	Approved
0.8686	High Similarity	NPD7251	Discontinued
0.8678	High Similarity	NPD7074	Phase 3
0.8639	High Similarity	NPD4381	Clinical (unspecified phase)
0.8636	High Similarity	NPD7808	Phase 3
0.8636	High Similarity	NPD4338	Clinical (unspecified phase)
0.8629	High Similarity	NPD6797	Phase 2
0.8596	High Similarity	NPD6959	Discontinued
0.858	High Similarity	NPD6559	Discontinued
0.8514	High Similarity	NPD5844	Phase 1
0.8482	Intermediate Similarity	NPD7783	Phase 2
0.8482	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8474	Intermediate Similarity	NPD8151	Discontinued
0.8353	Intermediate Similarity	NPD7819	Suspended
0.8352	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8314	Intermediate Similarity	NPD7075	Discontinued
0.8307	Intermediate Similarity	NPD7435	Discontinued
0.8295	Intermediate Similarity	NPD7473	Discontinued
0.8284	Intermediate Similarity	NPD4380	Phase 2
0.8251	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8249	Intermediate Similarity	NPD7228	Approved
0.815	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6779	Approved
0.8148	Intermediate Similarity	NPD6781	Approved
0.8148	Intermediate Similarity	NPD6782	Approved
0.8148	Intermediate Similarity	NPD6780	Approved
0.8148	Intermediate Similarity	NPD6778	Approved
0.8148	Intermediate Similarity	NPD6777	Approved
0.8148	Intermediate Similarity	NPD6776	Approved
0.814	Intermediate Similarity	NPD8455	Phase 2
0.814	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD6166	Phase 2
0.8115	Intermediate Similarity	NPD7698	Approved
0.8115	Intermediate Similarity	NPD7697	Approved
0.8115	Intermediate Similarity	NPD7696	Phase 3
0.8095	Intermediate Similarity	NPD2534	Approved
0.8095	Intermediate Similarity	NPD2533	Approved
0.8095	Intermediate Similarity	NPD2532	Approved
0.8092	Intermediate Similarity	NPD5402	Approved
0.8081	Intermediate Similarity	NPD6801	Discontinued
0.8051	Intermediate Similarity	NPD7874	Approved
0.8051	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD7701	Phase 2
0.8035	Intermediate Similarity	NPD1465	Phase 2
0.8035	Intermediate Similarity	NPD2801	Approved
0.8011	Intermediate Similarity	NPD5494	Approved
0.8011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD7871	Phase 2
0.7979	Intermediate Similarity	NPD7870	Phase 2
0.7977	Intermediate Similarity	NPD1934	Approved
0.7969	Intermediate Similarity	NPD6823	Phase 2
0.7967	Intermediate Similarity	NPD7240	Approved
0.7947	Intermediate Similarity	NPD7699	Phase 2
0.7947	Intermediate Similarity	NPD7700	Phase 2
0.7933	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7411	Suspended
0.7886	Intermediate Similarity	NPD3817	Phase 2
0.7884	Intermediate Similarity	NPD6535	Approved
0.7884	Intermediate Similarity	NPD6534	Approved
0.7882	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD37	Approved
0.7853	Intermediate Similarity	NPD6234	Discontinued
0.7845	Intermediate Similarity	NPD3751	Discontinued
0.7844	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7768	Phase 2
0.7841	Intermediate Similarity	NPD4965	Approved
0.7841	Intermediate Similarity	NPD4966	Approved
0.7841	Intermediate Similarity	NPD4967	Phase 2
0.7828	Intermediate Similarity	NPD7801	Approved
0.7821	Intermediate Similarity	NPD3787	Discontinued
0.7795	Intermediate Similarity	NPD8320	Phase 1
0.7795	Intermediate Similarity	NPD8319	Approved
0.7759	Intermediate Similarity	NPD6599	Discontinued
0.7754	Intermediate Similarity	NPD8150	Discontinued
0.7701	Intermediate Similarity	NPD3226	Approved
0.7697	Intermediate Similarity	NPD3749	Approved
0.7688	Intermediate Similarity	NPD5403	Approved
0.7679	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7199	Phase 2
0.7659	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD3750	Approved
0.7644	Intermediate Similarity	NPD1653	Approved
0.7644	Intermediate Similarity	NPD6213	Phase 3
0.7644	Intermediate Similarity	NPD6212	Phase 3
0.7644	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD1549	Phase 2
0.7624	Intermediate Similarity	NPD5710	Approved
0.7624	Intermediate Similarity	NPD5711	Approved
0.7619	Intermediate Similarity	NPD2935	Discontinued
0.7616	Intermediate Similarity	NPD1511	Approved
0.7616	Intermediate Similarity	NPD7390	Discontinued
0.7616	Intermediate Similarity	NPD6799	Approved
0.7606	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7458	Discontinued
0.7581	Intermediate Similarity	NPD7685	Pre-registration
0.7574	Intermediate Similarity	NPD2346	Discontinued
0.7572	Intermediate Similarity	NPD5401	Approved
0.7542	Intermediate Similarity	NPD3882	Suspended
0.7538	Intermediate Similarity	NPD7584	Approved
0.7529	Intermediate Similarity	NPD1512	Approved
0.7515	Intermediate Similarity	NPD2796	Approved
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8434	Phase 2
0.7471	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1510	Phase 2
0.7449	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7585	Approved
0.7412	Intermediate Similarity	NPD1551	Phase 2
0.7386	Intermediate Similarity	NPD920	Approved
0.7384	Intermediate Similarity	NPD6674	Discontinued
0.7366	Intermediate Similarity	NPD7930	Approved
0.7363	Intermediate Similarity	NPD7583	Approved
0.7353	Intermediate Similarity	NPD3748	Approved
0.7353	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1607	Approved
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.7313	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8059	Phase 3
0.731	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7680	Approved
0.7288	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1247	Approved
0.7283	Intermediate Similarity	NPD2800	Approved
0.7283	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1243	Approved
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD919	Approved
0.7267	Intermediate Similarity	NPD7266	Discontinued
0.7249	Intermediate Similarity	NPD5953	Discontinued
0.7234	Intermediate Similarity	NPD7286	Phase 2
0.7219	Intermediate Similarity	NPD1240	Approved
0.7209	Intermediate Similarity	NPD5408	Approved
0.7209	Intermediate Similarity	NPD5405	Approved
0.7209	Intermediate Similarity	NPD5406	Approved
0.7209	Intermediate Similarity	NPD5404	Approved
0.7186	Intermediate Similarity	NPD8285	Discontinued
0.7175	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2799	Discontinued
0.715	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD7999	Approved
0.7143	Intermediate Similarity	NPD7003	Approved
0.713	Intermediate Similarity	NPD8067	Phase 3
0.7127	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2313	Discontinued
0.709	Intermediate Similarity	NPD7177	Discontinued
0.7083	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5124	Phase 1
0.7076	Intermediate Similarity	NPD230	Phase 1
0.7071	Intermediate Similarity	NPD4363	Phase 3
0.7071	Intermediate Similarity	NPD4360	Phase 2
0.7052	Intermediate Similarity	NPD7033	Discontinued
0.7039	Intermediate Similarity	NPD6273	Approved
0.7035	Intermediate Similarity	NPD6651	Approved
0.7021	Intermediate Similarity	NPD3926	Phase 2
0.7018	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4060	Phase 1
0.7018	Intermediate Similarity	NPD1613	Approved
0.7011	Intermediate Similarity	NPD2438	Suspended
0.701	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6844	Discontinued
0.6994	Remote Similarity	NPD7097	Phase 1
0.6989	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6832	Phase 2
0.6977	Remote Similarity	NPD1933	Approved
0.6919	Remote Similarity	NPD4288	Approved
0.6916	Remote Similarity	NPD8366	Approved
0.6915	Remote Similarity	NPD8127	Discontinued
0.6911	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7985	Registered
0.6893	Remote Similarity	NPD1652	Phase 2
0.6882	Remote Similarity	NPD4908	Phase 1

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