NPASS Compound

Structure

NPC470510 OpenBabel07101719242D 31 33 0 0 1 0 0 0 0 0999 V2000 -7.0327 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 4.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5686 3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5686 2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8988 -0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2007 0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 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 -4.4347 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 4 1 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 21 1 0 0 0 0 8 28 1 0 0 0 0 9 20 1 0 0 0 0 9 22 1 0 0 0 0 10 20 1 0 0 0 0 10 29 1 0 0 0 0 11 12 1 0 0 0 0 12 30 1 0 0 0 0 13 8 1 1 0 0 0 13 14 1 0 0 0 0 13 31 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 6 0 0 0 15 16 1 0 0 0 0 15 24 1 1 0 0 0 16 18 1 0 0 0 0 16 25 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 17 26 1 0 0 0 0 18 30 1 1 0 0 0 18 31 1 0 0 0 0 19 28 1 1 0 0 0 19 29 1 0 0 0 0 20 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.16
Volume:	414.953
LogP:	-0.516
LogD:	-0.481
LogS:	-2.178
# Rotatable Bonds:	8
TPSA:	178.53
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.222
Synthetic Accessibility Score:	4.525
Fsp3:	0.6
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.04
MDCK Permeability:	2.943929393950384e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.819
Human Intestinal Absorption (HIA):	0.912
20% Bioavailability (F20%):	0.815
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.214
Plasma Protein Binding (PPB):	43.95538330078125%
Volume Distribution (VD):	0.387
Pgp-substrate:	31.739234924316406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.031

ADMET: Excretion

Clearance (CL):	1.178
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.142
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.69
AMES Toxicity:	0.487
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.907
Carcinogencity:	0.197
Eye Corrosion:	0.003
Eye Irritation:	0.068
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC470510

Natural Product ID:	NPC470510
*Common Name:**	Cinnacasolide B
IUPAC Name:	(2R,3S,4S,5R,6S)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-[(E)-3-hydroxyprop-1-enyl]phenoxy]oxane-3,4,5-triol
Synonyms:	Cinnacasolide B
Standard InCHIKey:	OBAALXPOHKOEEY-IDPVQYMJSA-N
Standard InCHI:	InChI=1S/C20H28O11/c21-7-3-5-11-4-1-2-6-12(11)30-18-16(25)15(24)14(23)13(31-18)8-28-19-17(26)20(27,9-22)10-29-19/h1-6,13-19,21-27H,7-10H2/b5-3+/t13-,14-,15+,16-,17+,18-,19-,20-/m1/s1
SMILES:	OC/C=C/c1ccccc1O[C@@H]1O[C@H](CO[C@@H]2OC[C@]([C@H]2O)(O)CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048805
PubChem CID:	70692599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[19555125]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[22677314]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	Inhibition	=	35.4	%	PMID[550569]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[550569]

☑ 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 NPC470510 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	342
0.1-0.2	1317
0.2-0.3	3730
0.3-0.4	9886
0.4-0.5	9176
0.5-0.6	7135
0.6-0.7	8676
0.7-0.8	2191
0.8-0.85	206
0.85-0.9	30
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9496	High Similarity	NPC226712
0.9421	High Similarity	NPC287429
0.925	High Similarity	NPC469412
0.925	High Similarity	NPC198734
0.925	High Similarity	NPC269242
0.9147	High Similarity	NPC469383
0.9127	High Similarity	NPC474491
0.912	High Similarity	NPC146540
0.912	High Similarity	NPC40377
0.9062	High Similarity	NPC25821
0.9048	High Similarity	NPC97326
0.9008	High Similarity	NPC60589
0.9008	High Similarity	NPC469708
0.8906	High Similarity	NPC166168
0.8846	High Similarity	NPC87696
0.8806	High Similarity	NPC472353
0.879	High Similarity	NPC476142
0.8779	High Similarity	NPC79957
0.8769	High Similarity	NPC6836
0.875	High Similarity	NPC248355
0.875	High Similarity	NPC166040
0.8731	High Similarity	NPC215512
0.8731	High Similarity	NPC476442
0.8722	High Similarity	NPC183781
0.8712	High Similarity	NPC104167
0.8712	High Similarity	NPC166180
0.8702	High Similarity	NPC34456
0.8702	High Similarity	NPC470881
0.8692	High Similarity	NPC252833
0.8692	High Similarity	NPC269421
0.8682	High Similarity	NPC80600
0.8682	High Similarity	NPC472024
0.8678	High Similarity	NPC175771
0.8672	High Similarity	NPC302378
0.8647	High Similarity	NPC87777
0.8647	High Similarity	NPC262328
0.8644	High Similarity	NPC264784
0.8629	High Similarity	NPC476445
0.8629	High Similarity	NPC469548
0.8629	High Similarity	NPC476448
0.8626	High Similarity	NPC215037
0.8615	High Similarity	NPC9912
0.8605	High Similarity	NPC218003
0.8605	High Similarity	NPC295970
0.8605	High Similarity	NPC26653
0.8605	High Similarity	NPC270849
0.8593	High Similarity	NPC108674
0.8583	High Similarity	NPC12308
0.8571	High Similarity	NPC475628
0.8561	High Similarity	NPC471029
0.855	High Similarity	NPC303422
0.855	High Similarity	NPC26080
0.855	High Similarity	NPC85799
0.855	High Similarity	NPC165686
0.8548	High Similarity	NPC282409
0.8548	High Similarity	NPC469702
0.8538	High Similarity	NPC262606
0.8512	High Similarity	NPC142319
0.8512	High Similarity	NPC313193
0.8507	High Similarity	NPC134260
0.8485	Intermediate Similarity	NPC115022
0.8485	Intermediate Similarity	NPC49074
0.8485	Intermediate Similarity	NPC294166
0.8478	Intermediate Similarity	NPC43508
0.8478	Intermediate Similarity	NPC476301
0.8473	Intermediate Similarity	NPC65942
0.8473	Intermediate Similarity	NPC475067
0.8473	Intermediate Similarity	NPC121376
0.8473	Intermediate Similarity	NPC248307
0.8467	Intermediate Similarity	NPC46092
0.8462	Intermediate Similarity	NPC307110
0.8456	Intermediate Similarity	NPC210192
0.845	Intermediate Similarity	NPC198798
0.8433	Intermediate Similarity	NPC103409
0.8429	Intermediate Similarity	NPC169510
0.8425	Intermediate Similarity	NPC470907
0.8425	Intermediate Similarity	NPC232454
0.8425	Intermediate Similarity	NPC178449
0.8421	Intermediate Similarity	NPC187194
0.8421	Intermediate Similarity	NPC476411
0.8421	Intermediate Similarity	NPC251981
0.8421	Intermediate Similarity	NPC48863
0.8421	Intermediate Similarity	NPC13745
0.8421	Intermediate Similarity	NPC188555
0.8421	Intermediate Similarity	NPC130496
0.8409	Intermediate Similarity	NPC299144
0.8409	Intermediate Similarity	NPC162093
0.8406	Intermediate Similarity	NPC283995
0.8406	Intermediate Similarity	NPC217635
0.8406	Intermediate Similarity	NPC129417
0.8406	Intermediate Similarity	NPC470235
0.8406	Intermediate Similarity	NPC471667
0.8406	Intermediate Similarity	NPC79429
0.8394	Intermediate Similarity	NPC145319
0.8394	Intermediate Similarity	NPC245219
0.8394	Intermediate Similarity	NPC230718
0.8394	Intermediate Similarity	NPC475084
0.8394	Intermediate Similarity	NPC84207
0.8394	Intermediate Similarity	NPC128337
0.8394	Intermediate Similarity	NPC31081
0.8394	Intermediate Similarity	NPC49542
0.8394	Intermediate Similarity	NPC5253
0.8394	Intermediate Similarity	NPC139976
0.8387	Intermediate Similarity	NPC228907
0.8374	Intermediate Similarity	NPC148055
0.8372	Intermediate Similarity	NPC171533
0.837	Intermediate Similarity	NPC470413
0.837	Intermediate Similarity	NPC138738
0.837	Intermediate Similarity	NPC195196
0.8361	Intermediate Similarity	NPC157338
0.8358	Intermediate Similarity	NPC185778
0.8358	Intermediate Similarity	NPC238243
0.8357	Intermediate Similarity	NPC15956
0.8357	Intermediate Similarity	NPC31325
0.8357	Intermediate Similarity	NPC224674
0.8357	Intermediate Similarity	NPC193473
0.8357	Intermediate Similarity	NPC275284
0.8357	Intermediate Similarity	NPC296377
0.8357	Intermediate Similarity	NPC213074
0.8357	Intermediate Similarity	NPC114505
0.8346	Intermediate Similarity	NPC471067
0.8346	Intermediate Similarity	NPC215833
0.8346	Intermediate Similarity	NPC69513
0.8345	Intermediate Similarity	NPC18979
0.8345	Intermediate Similarity	NPC469586
0.8333	Intermediate Similarity	NPC470950
0.8333	Intermediate Similarity	NPC252169
0.8333	Intermediate Similarity	NPC242756
0.8333	Intermediate Similarity	NPC116922
0.8333	Intermediate Similarity	NPC185307
0.831	Intermediate Similarity	NPC98624
0.8306	Intermediate Similarity	NPC9248
0.8296	Intermediate Similarity	NPC203230
0.8296	Intermediate Similarity	NPC172818
0.8296	Intermediate Similarity	NPC197723
0.8296	Intermediate Similarity	NPC164857
0.8296	Intermediate Similarity	NPC138350
0.8296	Intermediate Similarity	NPC3293
0.8296	Intermediate Similarity	NPC37468
0.8296	Intermediate Similarity	NPC165482
0.8296	Intermediate Similarity	NPC242028
0.8296	Intermediate Similarity	NPC40664
0.8296	Intermediate Similarity	NPC25695
0.8295	Intermediate Similarity	NPC90318
0.8286	Intermediate Similarity	NPC112861
0.8284	Intermediate Similarity	NPC35731
0.8273	Intermediate Similarity	NPC168579
0.8273	Intermediate Similarity	NPC469313
0.8273	Intermediate Similarity	NPC177597
0.8273	Intermediate Similarity	NPC76176
0.8273	Intermediate Similarity	NPC138227
0.8273	Intermediate Similarity	NPC292443
0.8273	Intermediate Similarity	NPC225445
0.8273	Intermediate Similarity	NPC232228
0.8268	Intermediate Similarity	NPC57751
0.8261	Intermediate Similarity	NPC253878
0.8261	Intermediate Similarity	NPC246947
0.8261	Intermediate Similarity	NPC476356
0.8261	Intermediate Similarity	NPC164599
0.825	Intermediate Similarity	NPC276061
0.825	Intermediate Similarity	NPC474148
0.8248	Intermediate Similarity	NPC106944
0.8244	Intermediate Similarity	NPC87224
0.8244	Intermediate Similarity	NPC222572
0.8235	Intermediate Similarity	NPC59324
0.8235	Intermediate Similarity	NPC477797
0.8235	Intermediate Similarity	NPC477798
0.8235	Intermediate Similarity	NPC304152
0.8235	Intermediate Similarity	NPC194034
0.8235	Intermediate Similarity	NPC65530
0.8235	Intermediate Similarity	NPC124149
0.8231	Intermediate Similarity	NPC233559
0.8227	Intermediate Similarity	NPC469700
0.8227	Intermediate Similarity	NPC474422
0.8222	Intermediate Similarity	NPC174191
0.8222	Intermediate Similarity	NPC55040
0.8222	Intermediate Similarity	NPC470236
0.822	Intermediate Similarity	NPC152384
0.822	Intermediate Similarity	NPC37714
0.8214	Intermediate Similarity	NPC226722
0.8214	Intermediate Similarity	NPC22150
0.8214	Intermediate Similarity	NPC279298
0.8214	Intermediate Similarity	NPC38041
0.8214	Intermediate Similarity	NPC138915
0.8214	Intermediate Similarity	NPC475096
0.8214	Intermediate Similarity	NPC85624
0.8209	Intermediate Similarity	NPC132895
0.8203	Intermediate Similarity	NPC52097
0.8201	Intermediate Similarity	NPC81638
0.8201	Intermediate Similarity	NPC37793
0.8195	Intermediate Similarity	NPC478255
0.8195	Intermediate Similarity	NPC162801
0.8189	Intermediate Similarity	NPC469704
0.8189	Intermediate Similarity	NPC201402
0.8189	Intermediate Similarity	NPC160854
0.8189	Intermediate Similarity	NPC473875
0.8189	Intermediate Similarity	NPC469703
0.8189	Intermediate Similarity	NPC475529
0.8188	Intermediate Similarity	NPC471414
0.8188	Intermediate Similarity	NPC5155

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 NPC470510 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	756
0.2-0.3	1767
0.3-0.4	2874
0.4-0.5	1810
0.5-0.6	1159
0.6-0.7	471
0.7-0.8	51
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9496	High Similarity	NPD1091	Approved
0.8235	Intermediate Similarity	NPD290	Approved
0.7887	Intermediate Similarity	NPD5058	Phase 3
0.7862	Intermediate Similarity	NPD1653	Approved
0.776	Intermediate Similarity	NPD7843	Approved
0.7737	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1613	Approved
0.7724	Intermediate Similarity	NPD2684	Approved
0.763	Intermediate Similarity	NPD2861	Phase 2
0.7615	Intermediate Similarity	NPD1357	Approved
0.76	Intermediate Similarity	NPD8455	Phase 2
0.7578	Intermediate Similarity	NPD7157	Approved
0.7578	Intermediate Similarity	NPD6671	Approved
0.7576	Intermediate Similarity	NPD3705	Approved
0.7566	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD968	Approved
0.7552	Intermediate Similarity	NPD6674	Discontinued
0.7538	Intermediate Similarity	NPD1548	Phase 1
0.7518	Intermediate Similarity	NPD7033	Discontinued
0.7518	Intermediate Similarity	NPD5588	Approved
0.7447	Intermediate Similarity	NPD7097	Phase 1
0.7445	Intermediate Similarity	NPD4908	Phase 1
0.7445	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1610	Phase 2
0.7431	Intermediate Similarity	NPD1652	Phase 2
0.7424	Intermediate Similarity	NPD5126	Approved
0.7424	Intermediate Similarity	NPD5125	Phase 3
0.7413	Intermediate Similarity	NPD7266	Discontinued
0.7407	Intermediate Similarity	NPD8651	Approved
0.7391	Intermediate Similarity	NPD3027	Phase 3
0.7372	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2424	Discontinued
0.7338	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4749	Approved
0.7324	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4538	Approved
0.7324	Intermediate Similarity	NPD4536	Approved
0.731	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5124	Phase 1
0.7305	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3818	Discontinued
0.7292	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6002	Phase 3
0.7292	Intermediate Similarity	NPD6004	Phase 3
0.7292	Intermediate Similarity	NPD5762	Approved
0.7292	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6005	Phase 3
0.7292	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD5960	Phase 3
0.7266	Intermediate Similarity	NPD969	Suspended
0.7254	Intermediate Similarity	NPD6653	Approved
0.7239	Intermediate Similarity	NPD3496	Discontinued
0.7236	Intermediate Similarity	NPD291	Approved
0.7222	Intermediate Similarity	NPD6559	Discontinued
0.7214	Intermediate Similarity	NPD6798	Discontinued
0.7214	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3685	Discontinued
0.7203	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9365	Approved
0.7185	Intermediate Similarity	NPD422	Phase 1
0.7183	Intermediate Similarity	NPD6355	Discontinued
0.7164	Intermediate Similarity	NPD1778	Approved
0.7164	Intermediate Similarity	NPD5846	Approved
0.7164	Intermediate Similarity	NPD6516	Phase 2
0.7163	Intermediate Similarity	NPD6233	Phase 2
0.7153	Intermediate Similarity	NPD3225	Approved
0.7153	Intermediate Similarity	NPD6696	Suspended
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD3179	Approved
0.7143	Intermediate Similarity	NPD3180	Approved
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2231	Phase 2
0.7132	Intermediate Similarity	NPD2235	Phase 2
0.7113	Intermediate Similarity	NPD4060	Phase 1
0.7109	Intermediate Similarity	NPD556	Approved
0.7099	Intermediate Similarity	NPD7074	Phase 3
0.7099	Intermediate Similarity	NPD7472	Approved
0.7095	Intermediate Similarity	NPD2677	Approved
0.7092	Intermediate Similarity	NPD1048	Approved
0.7089	Intermediate Similarity	NPD7199	Phase 2
0.7086	Intermediate Similarity	NPD5403	Approved
0.7078	Intermediate Similarity	NPD37	Approved
0.7067	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4340	Discontinued
0.7055	Intermediate Similarity	NPD6797	Phase 2
0.7051	Intermediate Similarity	NPD4965	Approved
0.7051	Intermediate Similarity	NPD4967	Phase 2
0.7051	Intermediate Similarity	NPD4966	Approved
0.705	Intermediate Similarity	NPD558	Phase 2
0.705	Intermediate Similarity	NPD5647	Approved
0.7044	Intermediate Similarity	NPD3787	Discontinued
0.7027	Intermediate Similarity	NPD4628	Phase 3
0.7012	Intermediate Similarity	NPD7251	Discontinued
0.6978	Remote Similarity	NPD6362	Approved
0.6978	Remote Similarity	NPD1794	Approved
0.6975	Remote Similarity	NPD7228	Approved
0.697	Remote Similarity	NPD7808	Phase 3
0.697	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6234	Discontinued
0.6954	Remote Similarity	NPD5401	Approved
0.6953	Remote Similarity	NPD1358	Approved
0.6948	Remote Similarity	NPD4380	Phase 2
0.6947	Remote Similarity	NPD821	Approved
0.6947	Remote Similarity	NPD1138	Approved
0.6939	Remote Similarity	NPD1375	Discontinued
0.6933	Remote Similarity	NPD3122	Phase 3
0.6929	Remote Similarity	NPD9697	Approved
0.6929	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD8312	Approved
0.6928	Remote Similarity	NPD8313	Approved
0.6923	Remote Similarity	NPD3162	Approved
0.6923	Remote Similarity	NPD3163	Approved
0.6923	Remote Similarity	NPD4062	Phase 3
0.6894	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1774	Approved
0.6879	Remote Similarity	NPD5402	Approved
0.6879	Remote Similarity	NPD3018	Phase 2
0.6875	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2238	Phase 2
0.6871	Remote Similarity	NPD3751	Discontinued
0.6871	Remote Similarity	NPD6032	Approved
0.687	Remote Similarity	NPD228	Approved
0.687	Remote Similarity	NPD1137	Approved
0.687	Remote Similarity	NPD1139	Approved
0.6857	Remote Similarity	NPD2797	Approved
0.6846	Remote Similarity	NPD5062	Approved
0.6846	Remote Similarity	NPD5061	Approved
0.6835	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1933	Approved
0.6828	Remote Similarity	NPD5735	Approved
0.6824	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9552	Approved
0.6818	Remote Similarity	NPD5535	Approved
0.6815	Remote Similarity	NPD2978	Approved
0.6815	Remote Similarity	NPD2977	Approved
0.6812	Remote Similarity	NPD776	Approved
0.6809	Remote Similarity	NPD3691	Phase 2
0.6809	Remote Similarity	NPD3690	Phase 2
0.6807	Remote Similarity	NPD7685	Pre-registration
0.68	Remote Similarity	NPD4535	Phase 3
0.68	Remote Similarity	NPD3892	Phase 2
0.68	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7075	Discontinued
0.6791	Remote Similarity	NPD2557	Approved
0.6791	Remote Similarity	NPD191	Approved
0.6783	Remote Similarity	NPD7095	Approved
0.6779	Remote Similarity	NPD1549	Phase 2
0.6776	Remote Similarity	NPD6799	Approved
0.6776	Remote Similarity	NPD7212	Phase 2
0.6776	Remote Similarity	NPD7213	Phase 3
0.6765	Remote Similarity	NPD1182	Approved
0.6765	Remote Similarity	NPD1894	Discontinued
0.6763	Remote Similarity	NPD9717	Approved
0.6757	Remote Similarity	NPD1551	Phase 2
0.6752	Remote Similarity	NPD1934	Approved
0.6752	Remote Similarity	NPD6801	Discontinued
0.6747	Remote Similarity	NPD7007	Discovery
0.6744	Remote Similarity	NPD3134	Approved
0.6738	Remote Similarity	NPD1819	Approved
0.6738	Remote Similarity	NPD1818	Approved
0.6738	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1817	Approved
0.6738	Remote Similarity	NPD1820	Approved
0.6738	Remote Similarity	NPD1203	Approved
0.6736	Remote Similarity	NPD3268	Approved
0.6736	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4237	Approved
0.6733	Remote Similarity	NPD4236	Phase 3
0.6732	Remote Similarity	NPD3536	Discontinued
0.6715	Remote Similarity	NPD6382	Discontinued
0.6715	Remote Similarity	NPD5585	Approved
0.6714	Remote Similarity	NPD2982	Phase 2
0.6714	Remote Similarity	NPD6583	Phase 3
0.6714	Remote Similarity	NPD2983	Phase 2
0.6714	Remote Similarity	NPD6582	Phase 2
0.6713	Remote Similarity	NPD6832	Phase 2
0.6711	Remote Similarity	NPD5756	Phase 2
0.6709	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5773	Approved
0.6709	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5772	Approved
0.6707	Remote Similarity	NPD7240	Approved
0.6691	Remote Similarity	NPD1535	Discovery
0.6689	Remote Similarity	NPD2154	Approved
0.6689	Remote Similarity	NPD2156	Approved
0.6689	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4108	Discontinued
0.6689	Remote Similarity	NPD2155	Approved
0.6689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6072	Discontinued
0.6688	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6387	Discontinued
0.6667	Remote Similarity	NPD709	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