NPASS Compound

Structure

NPC475273 OpenBabel07101719522D 44 49 0 0 1 0 0 0 0 0999 V2000 -2.9212 13.1328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3586 1.7642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2942 0.3066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6881 -0.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0262 0.7639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2295 12.1815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5598 11.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8680 10.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1983 9.7449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5066 8.7936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8369 8.0510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1452 7.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4755 6.3571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7837 5.4058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1140 4.6632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4223 3.7119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7526 2.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0609 2.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3911 1.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9280 -0.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7056 0.7380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6381 -3.6289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4056 0.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7370 -1.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1678 0.2510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1190 -1.1002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6757 -1.2618 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4280 -2.0513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5491 -0.7748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8099 -2.2527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8771 -2.8859 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5641 0.2251 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1189 -2.9755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6994 0.3240 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4280 -2.0513 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1827 -0.7489 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4508 -4.6112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0158 -2.8603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3900 -3.7443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6591 -2.6906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0904 -3.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3888 -0.0208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0823 -0.1577 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 6 1 0 0 0 0 2 23 2 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 32 1 0 0 0 0 22 37 1 0 0 0 0 24 28 1 0 0 0 0 25 36 1 1 0 0 0 26 35 1 6 0 0 0 26 36 1 0 0 0 0 27 29 1 0 0 0 0 27 30 1 0 0 0 0 27 36 1 1 0 0 0 28 35 1 0 0 0 0 28 38 2 0 0 0 0 29 32 1 6 0 0 0 29 42 1 0 0 0 0 30 33 1 1 0 0 0 30 41 1 0 0 0 0 31 33 1 6 0 0 0 31 35 1 0 0 0 0 31 39 1 0 0 0 0 32 23 1 1 0 0 0 32 43 1 0 0 0 0 33 22 1 6 0 0 0 33 41 1 0 0 0 0 34 19 1 6 0 0 0 34 42 1 0 0 0 0 34 43 1 0 0 0 0 34 44 1 0 0 0 0 35 40 1 6 0 0 0 36 44 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.4
Volume:	642.286
LogP:	7.383
LogD:	4.568
LogS:	-4.436
# Rotatable Bonds:	16
TPSA:	117.98
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	6.387
Fsp3:	0.861
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:	-4.954
MDCK Permeability:	2.5990433641709387e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.066
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.507
Plasma Protein Binding (PPB):	98.38436126708984%
Volume Distribution (VD):	1.967
Pgp-substrate:	3.054975748062134%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.926
CYP2C19-inhibitor:	0.345
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.335
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	10.248
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.705
Human Hepatotoxicity (H-HT):	0.895
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.693
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.921
Carcinogencity:	0.443
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC475273

Natural Product ID:	NPC475273
*Common Name:**	NSMGHRRDBZDSFL-WVGMNTNRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NSMGHRRDBZDSFL-WVGMNTNRSA-N
Standard InCHI:	InChI=1S/C36H56O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-34-42-29-27-30-33(22-37,41-30)31(39)35(40)26(20-24(4)28(35)38)36(27,44-34)25(5)21-32(29,43-34)23(2)3/h20,25-27,29-31,37,39-40H,2,6-19,21-22H2,1,3-5H3/t25-,26-,27-,29-,30+,31-,32-,33+,34-,35-,36+/m1/s1
SMILES:	CCCCCCCCCCCCCCC[C@@]12O[C@H]3[C@@](O1)(C[C@H]([C@@]1(O2)[C@H]3[C@@H]2O[C@@]2([C@H]([C@]2([C@H]1C=C(C2=O)C)O)O)CO)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502490
PubChem CID:	44559843
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

*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
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.04	nmol	PMID[527748]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	25.0	/nmol	PMID[527748]

☑ 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 NPC475273 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	286
0.1-0.2	1673
0.2-0.3	4890
0.3-0.4	7819
0.4-0.5	12870
0.5-0.6	8524
0.6-0.7	5264
0.7-0.8	1277
0.8-0.85	43
0.85-0.9	17
0.9-0.95	1
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168849
0.9914	High Similarity	NPC217901
0.9831	High Similarity	NPC162495
0.9667	High Similarity	NPC473485
0.9667	High Similarity	NPC474508
0.9667	High Similarity	NPC475139
0.9667	High Similarity	NPC180902
0.9583	High Similarity	NPC475606
0.9583	High Similarity	NPC251564
0.9583	High Similarity	NPC475314
0.9583	High Similarity	NPC477189
0.9508	High Similarity	NPC182266
0.9508	High Similarity	NPC100017
0.9508	High Similarity	NPC473548
0.9508	High Similarity	NPC471136
0.9508	High Similarity	NPC471137
0.9508	High Similarity	NPC475500
0.9508	High Similarity	NPC223356
0.9508	High Similarity	NPC475154
0.9355	High Similarity	NPC68282
0.9256	High Similarity	NPC476078
0.9256	High Similarity	NPC476091
0.9106	High Similarity	NPC475389
0.9106	High Similarity	NPC473838
0.9083	High Similarity	NPC473802
0.9008	High Similarity	NPC473709
0.9008	High Similarity	NPC473919
0.8992	High Similarity	NPC142882
0.8934	High Similarity	NPC471939
0.8862	High Similarity	NPC471940
0.864	High Similarity	NPC270109
0.8525	High Similarity	NPC329008
0.8525	High Similarity	NPC317635
0.8492	Intermediate Similarity	NPC236999
0.848	Intermediate Similarity	NPC222307
0.8468	Intermediate Similarity	NPC472399
0.8387	Intermediate Similarity	NPC19464
0.8387	Intermediate Similarity	NPC257017
0.8387	Intermediate Similarity	NPC162009
0.8306	Intermediate Similarity	NPC52839
0.8306	Intermediate Similarity	NPC472401
0.8306	Intermediate Similarity	NPC477046
0.8306	Intermediate Similarity	NPC102822
0.8268	Intermediate Similarity	NPC298841
0.8226	Intermediate Similarity	NPC157252
0.8226	Intermediate Similarity	NPC471126
0.8226	Intermediate Similarity	NPC145182
0.8226	Intermediate Similarity	NPC471128
0.8189	Intermediate Similarity	NPC225049
0.8145	Intermediate Similarity	NPC5991
0.8145	Intermediate Similarity	NPC5989
0.8145	Intermediate Similarity	NPC471108
0.8145	Intermediate Similarity	NPC22628
0.8145	Intermediate Similarity	NPC255081
0.8145	Intermediate Similarity	NPC275696
0.8125	Intermediate Similarity	NPC42399
0.811	Intermediate Similarity	NPC145238
0.811	Intermediate Similarity	NPC470922
0.808	Intermediate Similarity	NPC112038
0.808	Intermediate Similarity	NPC472004
0.8077	Intermediate Similarity	NPC476852
0.8067	Intermediate Similarity	NPC29827
0.8065	Intermediate Similarity	NPC472758
0.8065	Intermediate Similarity	NPC146280
0.8065	Intermediate Similarity	NPC204552
0.8065	Intermediate Similarity	NPC124676
0.8065	Intermediate Similarity	NPC471125
0.8065	Intermediate Similarity	NPC188667
0.8065	Intermediate Similarity	NPC171905
0.8065	Intermediate Similarity	NPC472397
0.8033	Intermediate Similarity	NPC477126
0.8031	Intermediate Similarity	NPC469352
0.803	Intermediate Similarity	NPC471234
0.8015	Intermediate Similarity	NPC471855
0.8	Intermediate Similarity	NPC476529
0.8	Intermediate Similarity	NPC476107
0.8	Intermediate Similarity	NPC475371
0.8	Intermediate Similarity	NPC469488
0.8	Intermediate Similarity	NPC475775
0.8	Intermediate Similarity	NPC476851
0.7985	Intermediate Similarity	NPC596
0.7984	Intermediate Similarity	NPC470854
0.7984	Intermediate Similarity	NPC97908
0.7984	Intermediate Similarity	NPC122033
0.7984	Intermediate Similarity	NPC287343
0.7984	Intermediate Similarity	NPC10721
0.7984	Intermediate Similarity	NPC156252
0.7984	Intermediate Similarity	NPC470780
0.7984	Intermediate Similarity	NPC474654
0.7969	Intermediate Similarity	NPC24651
0.7939	Intermediate Similarity	NPC476855
0.7937	Intermediate Similarity	NPC107338
0.7937	Intermediate Similarity	NPC109607
0.7937	Intermediate Similarity	NPC143755
0.7923	Intermediate Similarity	NPC476859
0.7923	Intermediate Similarity	NPC473620
0.792	Intermediate Similarity	NPC297179
0.791	Intermediate Similarity	NPC471089
0.791	Intermediate Similarity	NPC190065
0.791	Intermediate Similarity	NPC141215
0.7907	Intermediate Similarity	NPC473635
0.7903	Intermediate Similarity	NPC234858
0.7903	Intermediate Similarity	NPC471127
0.7903	Intermediate Similarity	NPC154363
0.7899	Intermediate Similarity	NPC471172
0.7891	Intermediate Similarity	NPC49297
0.7891	Intermediate Similarity	NPC471392
0.7891	Intermediate Similarity	NPC91693
0.7891	Intermediate Similarity	NPC67251
0.7891	Intermediate Similarity	NPC265557
0.7891	Intermediate Similarity	NPC18945
0.7891	Intermediate Similarity	NPC105926
0.7886	Intermediate Similarity	NPC474937
0.7886	Intermediate Similarity	NPC477091
0.7879	Intermediate Similarity	NPC6274
0.7879	Intermediate Similarity	NPC33378
0.7879	Intermediate Similarity	NPC472769
0.7879	Intermediate Similarity	NPC254614
0.7879	Intermediate Similarity	NPC100390
0.7879	Intermediate Similarity	NPC254146
0.7874	Intermediate Similarity	NPC310511
0.7874	Intermediate Similarity	NPC470779
0.7863	Intermediate Similarity	NPC476854
0.7863	Intermediate Similarity	NPC471407
0.7863	Intermediate Similarity	NPC470851
0.7863	Intermediate Similarity	NPC231529
0.7862	Intermediate Similarity	NPC146310
0.7857	Intermediate Similarity	NPC19028
0.7857	Intermediate Similarity	NPC9674
0.7857	Intermediate Similarity	NPC472667
0.7857	Intermediate Similarity	NPC470186
0.7852	Intermediate Similarity	NPC140045
0.7852	Intermediate Similarity	NPC295885
0.7846	Intermediate Similarity	NPC287423
0.7846	Intermediate Similarity	NPC305496
0.7842	Intermediate Similarity	NPC48813
0.7842	Intermediate Similarity	NPC194854
0.784	Intermediate Similarity	NPC27999
0.784	Intermediate Similarity	NPC477116
0.7836	Intermediate Similarity	NPC262813
0.7833	Intermediate Similarity	NPC474716
0.7829	Intermediate Similarity	NPC86346
0.7829	Intermediate Similarity	NPC469379
0.7829	Intermediate Similarity	NPC75856
0.7829	Intermediate Similarity	NPC476729
0.7823	Intermediate Similarity	NPC472400
0.7823	Intermediate Similarity	NPC181924
0.7823	Intermediate Similarity	NPC474872
0.782	Intermediate Similarity	NPC475487
0.782	Intermediate Similarity	NPC88668
0.782	Intermediate Similarity	NPC478151
0.782	Intermediate Similarity	NPC168879
0.7812	Intermediate Similarity	NPC312833
0.7812	Intermediate Similarity	NPC222688
0.7805	Intermediate Similarity	NPC170212
0.7805	Intermediate Similarity	NPC221511
0.7805	Intermediate Similarity	NPC17138
0.7805	Intermediate Similarity	NPC101825
0.7805	Intermediate Similarity	NPC215643
0.7805	Intermediate Similarity	NPC151216
0.7805	Intermediate Similarity	NPC475391
0.7805	Intermediate Similarity	NPC471933
0.7805	Intermediate Similarity	NPC89227
0.7805	Intermediate Similarity	NPC265499
0.7803	Intermediate Similarity	NPC476863
0.7803	Intermediate Similarity	NPC476862
0.7803	Intermediate Similarity	NPC471170
0.7795	Intermediate Similarity	NPC48692
0.7795	Intermediate Similarity	NPC19336
0.7795	Intermediate Similarity	NPC472759
0.7795	Intermediate Similarity	NPC329080
0.7795	Intermediate Similarity	NPC241192
0.7795	Intermediate Similarity	NPC185876
0.7795	Intermediate Similarity	NPC475885
0.7794	Intermediate Similarity	NPC290746
0.7794	Intermediate Similarity	NPC79250
0.7786	Intermediate Similarity	NPC188291
0.7786	Intermediate Similarity	NPC475462
0.7786	Intermediate Similarity	NPC311534
0.7786	Intermediate Similarity	NPC470850
0.7786	Intermediate Similarity	NPC16729
0.7778	Intermediate Similarity	NPC17772
0.7778	Intermediate Similarity	NPC251998
0.7778	Intermediate Similarity	NPC251310
0.7769	Intermediate Similarity	NPC47113
0.7769	Intermediate Similarity	NPC293112
0.7769	Intermediate Similarity	NPC174367
0.7761	Intermediate Similarity	NPC476823
0.776	Intermediate Similarity	NPC235539
0.776	Intermediate Similarity	NPC471816
0.776	Intermediate Similarity	NPC207217
0.776	Intermediate Similarity	NPC40632
0.776	Intermediate Similarity	NPC152199
0.776	Intermediate Similarity	NPC270478
0.776	Intermediate Similarity	NPC251236
0.776	Intermediate Similarity	NPC477509
0.776	Intermediate Similarity	NPC302471
0.776	Intermediate Similarity	NPC96312
0.776	Intermediate Similarity	NPC328374
0.776	Intermediate Similarity	NPC134869

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 NPC475273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	1902
0.2-0.3	3961
0.3-0.4	1994
0.4-0.5	607
0.5-0.6	265
0.6-0.7	154
0.7-0.8	21
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
0.7795	Intermediate Similarity	NPD6054	Approved
0.7686	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6370	Approved
0.7656	Intermediate Similarity	NPD6059	Approved
0.7597	Intermediate Similarity	NPD6015	Approved
0.7597	Intermediate Similarity	NPD6016	Approved
0.7594	Intermediate Similarity	NPD7319	Approved
0.7557	Intermediate Similarity	NPD7492	Approved
0.7538	Intermediate Similarity	NPD5988	Approved
0.7519	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD6616	Approved
0.748	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8293	Discontinued
0.7444	Intermediate Similarity	NPD7078	Approved
0.7368	Intermediate Similarity	NPD7507	Approved
0.7348	Intermediate Similarity	NPD8328	Phase 3
0.7252	Intermediate Similarity	NPD6319	Approved
0.7222	Intermediate Similarity	NPD6371	Approved
0.7197	Intermediate Similarity	NPD8513	Phase 3
0.7197	Intermediate Similarity	NPD8516	Approved
0.7197	Intermediate Similarity	NPD8517	Approved
0.7197	Intermediate Similarity	NPD8515	Approved
0.7176	Intermediate Similarity	NPD7516	Approved
0.7154	Intermediate Similarity	NPD7115	Discovery
0.7132	Intermediate Similarity	NPD6033	Approved
0.7109	Intermediate Similarity	NPD8297	Approved
0.7109	Intermediate Similarity	NPD6882	Approved
0.7099	Intermediate Similarity	NPD7327	Approved
0.7099	Intermediate Similarity	NPD7328	Approved
0.7063	Intermediate Similarity	NPD6686	Approved
0.7023	Intermediate Similarity	NPD6009	Approved
0.7023	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5344	Discontinued
0.6953	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4634	Approved
0.694	Remote Similarity	NPD8033	Approved
0.694	Remote Similarity	NPD8335	Approved
0.694	Remote Similarity	NPD8379	Approved
0.694	Remote Similarity	NPD8378	Approved
0.694	Remote Similarity	NPD6921	Approved
0.694	Remote Similarity	NPD8296	Approved
0.694	Remote Similarity	NPD8380	Approved
0.6934	Remote Similarity	NPD8074	Phase 3
0.6923	Remote Similarity	NPD4632	Approved
0.6905	Remote Similarity	NPD6008	Approved
0.6899	Remote Similarity	NPD6649	Approved
0.6899	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6650	Approved
0.6875	Remote Similarity	NPD6372	Approved
0.6875	Remote Similarity	NPD6373	Approved
0.6866	Remote Similarity	NPD8294	Approved
0.6866	Remote Similarity	NPD8377	Approved
0.686	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6412	Phase 2
0.6829	Remote Similarity	NPD4225	Approved
0.6807	Remote Similarity	NPD46	Approved
0.6807	Remote Similarity	NPD6698	Approved
0.6797	Remote Similarity	NPD6899	Approved
0.6797	Remote Similarity	NPD7320	Approved
0.6797	Remote Similarity	NPD6881	Approved
0.6794	Remote Similarity	NPD8133	Approved
0.6777	Remote Similarity	NPD5282	Discontinued
0.6772	Remote Similarity	NPD7128	Approved
0.6772	Remote Similarity	NPD5739	Approved
0.6772	Remote Similarity	NPD6675	Approved
0.6772	Remote Similarity	NPD6402	Approved
0.6769	Remote Similarity	NPD8130	Phase 1
0.6744	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1695	Approved
0.6719	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5697	Approved
0.6718	Remote Similarity	NPD6053	Discontinued
0.6715	Remote Similarity	NPD7604	Phase 2
0.6692	Remote Similarity	NPD7102	Approved
0.6692	Remote Similarity	NPD6883	Approved
0.6692	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6641	Remote Similarity	NPD6869	Approved
0.6641	Remote Similarity	NPD6617	Approved
0.6641	Remote Similarity	NPD6847	Approved
0.664	Remote Similarity	NPD4696	Approved
0.664	Remote Similarity	NPD6648	Approved
0.664	Remote Similarity	NPD5286	Approved
0.664	Remote Similarity	NPD5285	Approved
0.6615	Remote Similarity	NPD6014	Approved
0.6615	Remote Similarity	NPD6013	Approved
0.6615	Remote Similarity	NPD6012	Approved
0.6613	Remote Similarity	NPD4755	Approved
0.6589	Remote Similarity	NPD5701	Approved
0.6573	Remote Similarity	NPD8338	Approved
0.6569	Remote Similarity	NPD7503	Approved
0.6569	Remote Similarity	NPD5983	Phase 2
0.6562	Remote Similarity	NPD5141	Approved
0.656	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5956	Approved
0.6538	Remote Similarity	NPD6011	Approved
0.6535	Remote Similarity	NPD5224	Approved
0.6535	Remote Similarity	NPD5225	Approved
0.6535	Remote Similarity	NPD5226	Approved
0.6535	Remote Similarity	NPD4633	Approved
0.6508	Remote Similarity	NPD4700	Approved
0.65	Remote Similarity	NPD6336	Discontinued
0.6484	Remote Similarity	NPD5175	Approved
0.6484	Remote Similarity	NPD5174	Approved
0.6475	Remote Similarity	NPD7830	Approved
0.6475	Remote Similarity	NPD7829	Approved
0.6475	Remote Similarity	NPD7642	Approved
0.6457	Remote Similarity	NPD5223	Approved
0.6457	Remote Similarity	NPD1700	Approved
0.6433	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7638	Approved
0.6412	Remote Similarity	NPD4729	Approved
0.6412	Remote Similarity	NPD4730	Approved
0.6393	Remote Similarity	NPD7838	Discovery
0.6391	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD4768	Approved
0.6385	Remote Similarity	NPD4767	Approved
0.6378	Remote Similarity	NPD7640	Approved
0.6378	Remote Similarity	NPD7639	Approved
0.6357	Remote Similarity	NPD6067	Discontinued
0.6341	Remote Similarity	NPD7983	Approved
0.6331	Remote Similarity	NPD8269	Approved
0.6331	Remote Similarity	NPD8268	Approved
0.6331	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD8266	Approved
0.6331	Remote Similarity	NPD8267	Approved
0.6324	Remote Similarity	NPD6274	Approved
0.6316	Remote Similarity	NPD5248	Approved
0.6316	Remote Similarity	NPD5250	Approved
0.6316	Remote Similarity	NPD5247	Approved
0.6316	Remote Similarity	NPD5249	Phase 3
0.6316	Remote Similarity	NPD5251	Approved
0.6308	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7101	Approved
0.6304	Remote Similarity	NPD7100	Approved
0.6294	Remote Similarity	NPD8336	Approved
0.6294	Remote Similarity	NPD8337	Approved
0.6288	Remote Similarity	NPD5128	Approved
0.6286	Remote Similarity	NPD8080	Discontinued
0.6276	Remote Similarity	NPD7260	Phase 2
0.627	Remote Similarity	NPD4697	Phase 3
0.627	Remote Similarity	NPD5222	Approved
0.627	Remote Similarity	NPD5221	Approved
0.627	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7799	Discontinued
0.625	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD6845	Suspended
0.6232	Remote Similarity	NPD6335	Approved
0.6231	Remote Similarity	NPD4754	Approved
0.622	Remote Similarity	NPD6083	Phase 2
0.622	Remote Similarity	NPD6084	Phase 2
0.622	Remote Similarity	NPD5173	Approved
0.6216	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6079	Approved
0.6185	Remote Similarity	NPD8407	Phase 2
0.6179	Remote Similarity	NPD5328	Approved
0.616	Remote Similarity	NPD5779	Approved
0.616	Remote Similarity	NPD5778	Approved
0.6159	Remote Similarity	NPD6317	Approved
0.6154	Remote Similarity	NPD8451	Approved
0.6149	Remote Similarity	NPD8415	Approved
0.6148	Remote Similarity	NPD5215	Approved
0.6148	Remote Similarity	NPD5216	Approved
0.6148	Remote Similarity	NPD5217	Approved
0.6129	Remote Similarity	NPD3168	Discontinued
0.6115	Remote Similarity	NPD6314	Approved
0.6115	Remote Similarity	NPD6313	Approved
0.6111	Remote Similarity	NPD8448	Approved
0.6105	Remote Similarity	NPD8368	Discontinued
0.6099	Remote Similarity	NPD6909	Approved
0.6099	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD6908	Approved
0.6094	Remote Similarity	NPD7902	Approved
0.6074	Remote Similarity	NPD5169	Approved
0.6074	Remote Similarity	NPD5135	Approved
0.6074	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD4629	Approved
0.6063	Remote Similarity	NPD5210	Approved
0.6063	Remote Similarity	NPD5695	Phase 3
0.6063	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD4753	Phase 2
0.6048	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6101	Approved
0.6047	Remote Similarity	NPD5696	Approved
0.6032	Remote Similarity	NPD6399	Phase 3
0.6032	Remote Similarity	NPD4202	Approved
0.6029	Remote Similarity	NPD5127	Approved
0.6016	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD7641	Discontinued
0.5986	Remote Similarity	NPD8392	Approved
0.5986	Remote Similarity	NPD8391	Approved
0.5986	Remote Similarity	NPD8390	Approved
0.5986	Remote Similarity	NPD8444	Approved
0.5984	Remote Similarity	NPD7748	Approved
0.5972	Remote Similarity	NPD8341	Approved
0.5972	Remote Similarity	NPD8340	Approved
0.5972	Remote Similarity	NPD8299	Approved
0.5972	Remote Similarity	NPD8342	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