NPASS Compound

Structure

CID158673 OpenBabel06191715532D 32 34 0 0 1 0 0 0 0 0999 V2000 -4.3301 0.5000 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 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 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 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 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 -0.0000 3.0000 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 0.0000 0.0000 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 1 7 1 0 0 0 0 1 15 2 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 1 0 0 0 0 3 16 2 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 1 0 0 0 0 5 15 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 14 31 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 27 2 0 0 0 0 20 12 1 6 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 6 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 24 1 0 0 0 0 23 30 1 6 0 0 0 24 31 1 0 0 0 0 24 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.19
Volume:	449.857
LogP:	1.255
LogD:	1.224
LogS:	-2.622
# Rotatable Bonds:	10
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	3.842
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.516
MDCK Permeability:	7.651508894923609e-06
Pgp-inhibitor:	0.022
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.858
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	83.8742446899414%
Volume Distribution (VD):	0.575
Pgp-substrate:	8.693371772766113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.408
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.244
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	4.643
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.331
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.584
Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.796
Skin Sensitization:	0.929
Carcinogencity:	0.404
Eye Corrosion:	0.003
Eye Irritation:	0.143
Respiratory Toxicity:	0.119

Download Data

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

Natural Product: NPC158673

Natural Product ID:	NPC158673
*Common Name:**	Platyphyllonol-5-O-Beta-D-Xylopyranoside
IUPAC Name:	(5S)-1,7-bis(4-hydroxyphenyl)-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyheptan-3-one
Synonyms:
Standard InCHIKey:	GTGWRSYHHGXYAS-QOXFPCGXSA-N
Standard InCHI:	InChI=1S/C24H30O8/c25-17-7-1-15(2-8-17)5-11-19(27)13-20(12-6-16-3-9-18(26)10-4-16)32-24-23(30)22(29)21(28)14-31-24/h1-4,7-10,20-26,28-30H,5-6,11-14H2/t20-,21+,22-,23+,24-/m0/s1
SMILES:	Oc1ccc(cc1)CCC(=O)C[C@@H](O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346809
PubChem CID:	10599483
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20045319]
NPO32876	alnus hirsuta f. sibirica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23465614]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26341132]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	20.8	%	PMID[566516]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	14.4	%	PMID[566516]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	28.9	%	PMID[566516]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	81.7	%	PMID[566516]

☑ 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 NPC158673 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	288
0.1-0.2	1086
0.2-0.3	2533
0.3-0.4	6856
0.4-0.5	11780
0.5-0.6	6375
0.6-0.7	10847
0.7-0.8	2765
0.8-0.85	123
0.85-0.9	26
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9837	High Similarity	NPC469705
0.9837	High Similarity	NPC470122
0.9837	High Similarity	NPC17968
0.9758	High Similarity	NPC476407
0.968	High Similarity	NPC471066
0.968	High Similarity	NPC471095
0.9603	High Similarity	NPC164172
0.9453	High Similarity	NPC180171
0.9453	High Similarity	NPC158325
0.9453	High Similarity	NPC103398
0.9308	High Similarity	NPC469696
0.9024	High Similarity	NPC469703
0.9024	High Similarity	NPC469704
0.9024	High Similarity	NPC201402
0.9024	High Similarity	NPC160854
0.8952	High Similarity	NPC469686
0.8889	High Similarity	NPC469623
0.8889	High Similarity	NPC148080
0.888	High Similarity	NPC471067
0.8864	High Similarity	NPC123988
0.8837	High Similarity	NPC469549
0.881	High Similarity	NPC232454
0.881	High Similarity	NPC178449
0.881	High Similarity	NPC470907
0.8797	High Similarity	NPC471345
0.8731	High Similarity	NPC310252
0.8731	High Similarity	NPC302583
0.8731	High Similarity	NPC84789
0.8731	High Similarity	NPC100558
0.8682	High Similarity	NPC288416
0.8672	High Similarity	NPC123704
0.8643	High Similarity	NPC473138
0.8643	High Similarity	NPC28776
0.8618	High Similarity	NPC148055
0.8607	High Similarity	NPC157338
0.8605	High Similarity	NPC94179
0.8538	High Similarity	NPC108659
0.8538	High Similarity	NPC231607
0.8538	High Similarity	NPC469687
0.8538	High Similarity	NPC264900
0.8538	High Similarity	NPC79715
0.8512	High Similarity	NPC177576
0.8504	High Similarity	NPC55608
0.85	High Similarity	NPC212808
0.8492	Intermediate Similarity	NPC469702
0.8492	Intermediate Similarity	NPC282409
0.843	Intermediate Similarity	NPC321252
0.843	Intermediate Similarity	NPC252544
0.8425	Intermediate Similarity	NPC476448
0.8425	Intermediate Similarity	NPC476445
0.8425	Intermediate Similarity	NPC469548
0.8421	Intermediate Similarity	NPC281798
0.8421	Intermediate Similarity	NPC235294
0.8421	Intermediate Similarity	NPC46137
0.8421	Intermediate Similarity	NPC478255
0.8417	Intermediate Similarity	NPC478250
0.8409	Intermediate Similarity	NPC184092
0.8385	Intermediate Similarity	NPC126991
0.8385	Intermediate Similarity	NPC83218
0.838	Intermediate Similarity	NPC116229
0.837	Intermediate Similarity	NPC169398
0.8345	Intermediate Similarity	NPC259182
0.8345	Intermediate Similarity	NPC121001
0.8333	Intermediate Similarity	NPC225307
0.8333	Intermediate Similarity	NPC148982
0.8321	Intermediate Similarity	NPC471157
0.8321	Intermediate Similarity	NPC252114
0.832	Intermediate Similarity	NPC473556
0.832	Intermediate Similarity	NPC175771
0.832	Intermediate Similarity	NPC301651
0.831	Intermediate Similarity	NPC470330
0.8306	Intermediate Similarity	NPC313193
0.8306	Intermediate Similarity	NPC285350
0.8298	Intermediate Similarity	NPC475528
0.8295	Intermediate Similarity	NPC469927
0.8295	Intermediate Similarity	NPC52097
0.8288	Intermediate Similarity	NPC106625
0.8284	Intermediate Similarity	NPC225384
0.8284	Intermediate Similarity	NPC138777
0.8284	Intermediate Similarity	NPC246869
0.8261	Intermediate Similarity	NPC324262
0.8261	Intermediate Similarity	NPC62800
0.8252	Intermediate Similarity	NPC120728
0.8248	Intermediate Similarity	NPC472132
0.824	Intermediate Similarity	NPC23402
0.8239	Intermediate Similarity	NPC143246
0.8239	Intermediate Similarity	NPC119773
0.8239	Intermediate Similarity	NPC291153
0.8239	Intermediate Similarity	NPC474268
0.8239	Intermediate Similarity	NPC475539
0.8235	Intermediate Similarity	NPC287597
0.8235	Intermediate Similarity	NPC34293
0.8235	Intermediate Similarity	NPC886
0.8231	Intermediate Similarity	NPC236981
0.8231	Intermediate Similarity	NPC97052
0.8231	Intermediate Similarity	NPC39351
0.8231	Intermediate Similarity	NPC72649
0.8231	Intermediate Similarity	NPC26195
0.8231	Intermediate Similarity	NPC131532
0.8231	Intermediate Similarity	NPC99233
0.8231	Intermediate Similarity	NPC169248
0.8227	Intermediate Similarity	NPC296659
0.8227	Intermediate Similarity	NPC202391
0.8222	Intermediate Similarity	NPC254275
0.8219	Intermediate Similarity	NPC259767
0.8219	Intermediate Similarity	NPC88484
0.8219	Intermediate Similarity	NPC87403
0.8217	Intermediate Similarity	NPC11724
0.8217	Intermediate Similarity	NPC266045
0.8203	Intermediate Similarity	NPC34634
0.8203	Intermediate Similarity	NPC265454
0.8194	Intermediate Similarity	NPC287294
0.8188	Intermediate Similarity	NPC101686
0.8188	Intermediate Similarity	NPC469364
0.8188	Intermediate Similarity	NPC65262
0.8176	Intermediate Similarity	NPC170475
0.8176	Intermediate Similarity	NPC127406
0.8176	Intermediate Similarity	NPC206378
0.8175	Intermediate Similarity	NPC263829
0.8168	Intermediate Similarity	NPC231767
0.8163	Intermediate Similarity	NPC83283
0.8163	Intermediate Similarity	NPC29763
0.8163	Intermediate Similarity	NPC160882
0.8163	Intermediate Similarity	NPC143851
0.8163	Intermediate Similarity	NPC39360
0.8163	Intermediate Similarity	NPC210003
0.8162	Intermediate Similarity	NPC114116
0.8151	Intermediate Similarity	NPC106818
0.8148	Intermediate Similarity	NPC108553
0.814	Intermediate Similarity	NPC98305
0.814	Intermediate Similarity	NPC476872
0.8138	Intermediate Similarity	NPC12006
0.8138	Intermediate Similarity	NPC35097
0.8134	Intermediate Similarity	NPC253595
0.8125	Intermediate Similarity	NPC182240
0.8125	Intermediate Similarity	NPC472339
0.8121	Intermediate Similarity	NPC177742
0.8121	Intermediate Similarity	NPC258035
0.8121	Intermediate Similarity	NPC23817
0.8121	Intermediate Similarity	NPC156457
0.8121	Intermediate Similarity	NPC197896
0.8121	Intermediate Similarity	NPC161749
0.8121	Intermediate Similarity	NPC6985
0.8121	Intermediate Similarity	NPC43638
0.8121	Intermediate Similarity	NPC313163
0.812	Intermediate Similarity	NPC106677
0.8115	Intermediate Similarity	NPC317305
0.8112	Intermediate Similarity	NPC474465
0.8108	Intermediate Similarity	NPC95090
0.8108	Intermediate Similarity	NPC27408
0.8106	Intermediate Similarity	NPC127975
0.8106	Intermediate Similarity	NPC90318
0.8102	Intermediate Similarity	NPC471029
0.8099	Intermediate Similarity	NPC194938
0.8095	Intermediate Similarity	NPC257847
0.8085	Intermediate Similarity	NPC65833
0.8082	Intermediate Similarity	NPC474620
0.8067	Intermediate Similarity	NPC73511
0.8067	Intermediate Similarity	NPC308265
0.8058	Intermediate Similarity	NPC260425
0.8058	Intermediate Similarity	NPC78363
0.8054	Intermediate Similarity	NPC307938
0.8054	Intermediate Similarity	NPC149368
0.8054	Intermediate Similarity	NPC265480
0.8054	Intermediate Similarity	NPC203500
0.8054	Intermediate Similarity	NPC478055
0.8054	Intermediate Similarity	NPC323593
0.8043	Intermediate Similarity	NPC79957
0.8041	Intermediate Similarity	NPC205172
0.8041	Intermediate Similarity	NPC209393
0.8041	Intermediate Similarity	NPC185103
0.803	Intermediate Similarity	NPC244454
0.8029	Intermediate Similarity	NPC28637
0.8015	Intermediate Similarity	NPC476142
0.8015	Intermediate Similarity	NPC86900
0.8014	Intermediate Similarity	NPC79908
0.8014	Intermediate Similarity	NPC100818
0.8013	Intermediate Similarity	NPC208676
0.8013	Intermediate Similarity	NPC271270
0.8013	Intermediate Similarity	NPC130489
0.8013	Intermediate Similarity	NPC142860
0.8013	Intermediate Similarity	NPC97285
0.8013	Intermediate Similarity	NPC472320
0.8013	Intermediate Similarity	NPC246469
0.8013	Intermediate Similarity	NPC153342
0.8013	Intermediate Similarity	NPC200708
0.8013	Intermediate Similarity	NPC271479
0.8	Intermediate Similarity	NPC42911
0.8	Intermediate Similarity	NPC122809
0.8	Intermediate Similarity	NPC60966
0.8	Intermediate Similarity	NPC77672
0.8	Intermediate Similarity	NPC223335
0.8	Intermediate Similarity	NPC220936
0.8	Intermediate Similarity	NPC68092
0.8	Intermediate Similarity	NPC129827
0.8	Intermediate Similarity	NPC153795
0.8	Intermediate Similarity	NPC205195
0.8	Intermediate Similarity	NPC135391
0.8	Intermediate Similarity	NPC473512
0.8	Intermediate Similarity	NPC321184

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 NPC158673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	722
0.2-0.3	1388
0.3-0.4	2706
0.4-0.5	2278
0.5-0.6	1289
0.6-0.7	487
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8121	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7266	Discontinued
0.7718	Intermediate Similarity	NPD4380	Phase 2
0.7682	Intermediate Similarity	NPD8455	Phase 2
0.7658	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7074	Phase 3
0.7595	Intermediate Similarity	NPD3818	Discontinued
0.7547	Intermediate Similarity	NPD7054	Approved
0.7537	Intermediate Similarity	NPD1091	Approved
0.7535	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD7472	Approved
0.7453	Intermediate Similarity	NPD6797	Phase 2
0.7429	Intermediate Similarity	NPD6798	Discontinued
0.7407	Intermediate Similarity	NPD7251	Discontinued
0.7379	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7808	Phase 3
0.7329	Intermediate Similarity	NPD1549	Phase 2
0.7308	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD1934	Approved
0.7267	Intermediate Similarity	NPD7228	Approved
0.7261	Intermediate Similarity	NPD6234	Discontinued
0.7244	Intermediate Similarity	NPD4967	Phase 2
0.7244	Intermediate Similarity	NPD4966	Approved
0.7244	Intermediate Similarity	NPD4965	Approved
0.7241	Intermediate Similarity	NPD7033	Discontinued
0.723	Intermediate Similarity	NPD3400	Discontinued
0.723	Intermediate Similarity	NPD4628	Phase 3
0.7226	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2859	Approved
0.7213	Intermediate Similarity	NPD2860	Approved
0.7212	Intermediate Similarity	NPD8312	Approved
0.7212	Intermediate Similarity	NPD8313	Approved
0.72	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7097	Phase 1
0.7171	Intermediate Similarity	NPD5403	Approved
0.7165	Intermediate Similarity	NPD5048	Discontinued
0.7161	Intermediate Similarity	NPD6801	Discontinued
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4062	Phase 3
0.7132	Intermediate Similarity	NPD5125	Phase 3
0.7132	Intermediate Similarity	NPD5126	Approved
0.7131	Intermediate Similarity	NPD2933	Approved
0.7131	Intermediate Similarity	NPD2934	Approved
0.7125	Intermediate Similarity	NPD3787	Discontinued
0.7123	Intermediate Similarity	NPD1510	Phase 2
0.7115	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3027	Phase 3
0.7083	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1613	Approved
0.7068	Intermediate Similarity	NPD2629	Approved
0.7063	Intermediate Similarity	NPD3764	Approved
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD3020	Approved
0.7039	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5401	Approved
0.7039	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1535	Discovery
0.7025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5647	Approved
0.702	Intermediate Similarity	NPD5058	Phase 3
0.7018	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6663	Approved
0.7013	Intermediate Similarity	NPD1653	Approved
0.7007	Intermediate Similarity	NPD3019	Approved
0.7007	Intermediate Similarity	NPD2932	Approved
0.6988	Remote Similarity	NPD7685	Pre-registration
0.6987	Remote Similarity	NPD7411	Suspended
0.6985	Remote Similarity	NPD1894	Discontinued
0.6985	Remote Similarity	NPD9545	Approved
0.6978	Remote Similarity	NPD1481	Phase 2
0.6974	Remote Similarity	NPD6799	Approved
0.6972	Remote Similarity	NPD5736	Approved
0.6966	Remote Similarity	NPD1240	Approved
0.6966	Remote Similarity	NPD943	Approved
0.6962	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5402	Approved
0.6959	Remote Similarity	NPD2935	Discontinued
0.6957	Remote Similarity	NPD7199	Phase 2
0.6951	Remote Similarity	NPD3751	Discontinued
0.695	Remote Similarity	NPD3094	Phase 2
0.6947	Remote Similarity	NPD3022	Approved
0.6947	Remote Similarity	NPD3021	Approved
0.6933	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7843	Approved
0.6906	Remote Similarity	NPD1201	Approved
0.6906	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2798	Approved
0.6899	Remote Similarity	NPD2801	Approved
0.6887	Remote Similarity	NPD8166	Discontinued
0.6887	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7240	Approved
0.6884	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1607	Approved
0.687	Remote Similarity	NPD2684	Approved
0.6863	Remote Similarity	NPD1511	Approved
0.6859	Remote Similarity	NPD7458	Discontinued
0.6855	Remote Similarity	NPD3817	Phase 2
0.6853	Remote Similarity	NPD2861	Phase 2
0.6849	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2796	Approved
0.6846	Remote Similarity	NPD9570	Approved
0.6839	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6535	Approved
0.6839	Remote Similarity	NPD6534	Approved
0.6835	Remote Similarity	NPD3847	Discontinued
0.6831	Remote Similarity	NPD2797	Approved
0.6831	Remote Similarity	NPD1470	Approved
0.6831	Remote Similarity	NPD1164	Approved
0.6828	Remote Similarity	NPD3268	Approved
0.6825	Remote Similarity	NPD9495	Approved
0.6824	Remote Similarity	NPD4536	Approved
0.6824	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4538	Approved
0.6824	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1237	Approved
0.6821	Remote Similarity	NPD6674	Discontinued
0.6818	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6599	Discontinued
0.6809	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4908	Phase 1
0.6803	Remote Similarity	NPD1933	Approved
0.6792	Remote Similarity	NPD7819	Suspended
0.6786	Remote Similarity	NPD3092	Approved
0.6786	Remote Similarity	NPD1610	Phase 2
0.6783	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6212	Phase 3
0.6782	Remote Similarity	NPD6213	Phase 3
0.6779	Remote Similarity	NPD5588	Approved
0.6779	Remote Similarity	NPD5960	Phase 3
0.6776	Remote Similarity	NPD3750	Approved
0.6774	Remote Similarity	NPD1512	Approved
0.6772	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7157	Approved
0.6763	Remote Similarity	NPD6516	Phase 2
0.6763	Remote Similarity	NPD5846	Approved
0.6759	Remote Similarity	NPD7095	Approved
0.6755	Remote Similarity	NPD4534	Discontinued
0.6755	Remote Similarity	NPD2424	Discontinued
0.6755	Remote Similarity	NPD5958	Discontinued
0.6742	Remote Similarity	NPD6779	Approved
0.6742	Remote Similarity	NPD6777	Approved
0.6742	Remote Similarity	NPD6780	Approved
0.6742	Remote Similarity	NPD6778	Approved
0.6742	Remote Similarity	NPD6776	Approved
0.6742	Remote Similarity	NPD6782	Approved
0.6742	Remote Similarity	NPD6781	Approved
0.6739	Remote Similarity	NPD1548	Phase 1
0.6736	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD825	Approved
0.6735	Remote Similarity	NPD4060	Phase 1
0.6735	Remote Similarity	NPD826	Approved
0.6733	Remote Similarity	NPD5405	Approved
0.6733	Remote Similarity	NPD2438	Suspended
0.6733	Remote Similarity	NPD5406	Approved
0.6733	Remote Similarity	NPD5408	Approved
0.6733	Remote Similarity	NPD5404	Approved
0.6726	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7700	Phase 2
0.6723	Remote Similarity	NPD7699	Phase 2
0.6716	Remote Similarity	NPD969	Suspended
0.6715	Remote Similarity	NPD9493	Approved
0.6713	Remote Similarity	NPD1203	Approved
0.6712	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2313	Discontinued
0.671	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3882	Suspended
0.6705	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6832	Phase 2
0.669	Remote Similarity	NPD4659	Approved
0.6689	Remote Similarity	NPD230	Phase 1
0.6689	Remote Similarity	NPD4340	Discontinued
0.6667	Remote Similarity	NPD846	Approved
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD940	Approved
0.6667	Remote Similarity	NPD5535	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.6646	Remote Similarity	NPD6959	Discontinued
0.6645	Remote Similarity	NPD7390	Discontinued
0.6644	Remote Similarity	NPD6653	Approved
0.6644	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3225	Approved
0.6642	Remote Similarity	NPD255	Approved
0.6642	Remote Similarity	NPD256	Approved
0.6641	Remote Similarity	NPD7798	Approved
0.663	Remote Similarity	NPD7435	Discontinued
0.6627	Remote Similarity	NPD7852	Clinical (unspecified phase)

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