NPASS Compound

Structure

NPC473485 OpenBabel07101719252D 43 48 0 0 1 0 0 0 0 0999 V2000 -3.2295 -12.1815 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 -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 22 2 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 24 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 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 20 31 1 0 0 0 0 21 36 1 0 0 0 0 23 27 1 0 0 0 0 24 35 1 6 0 0 0 25 34 1 1 0 0 0 25 35 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 26 35 1 6 0 0 0 27 34 1 0 0 0 0 27 37 2 0 0 0 0 28 31 1 1 0 0 0 28 41 1 0 0 0 0 29 32 1 6 0 0 0 29 40 1 0 0 0 0 30 32 1 1 0 0 0 30 34 1 0 0 0 0 30 38 1 0 0 0 0 31 22 1 6 0 0 0 31 42 1 0 0 0 0 32 21 1 1 0 0 0 32 40 1 0 0 0 0 33 18 1 1 0 0 0 33 41 1 0 0 0 0 33 42 1 0 0 0 0 33 43 1 0 0 0 0 34 39 1 1 0 0 0 35 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	598.35
Volume:	619.717
LogP:	5.771
LogD:	4.219
LogS:	-4.041
# Rotatable Bonds:	13
TPSA:	117.98
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.12
Synthetic Accessibility Score:	6.635
Fsp3:	0.743
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:	-4.871
MDCK Permeability:	3.3690230338834226e-05
Pgp-inhibitor:	0.763
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.86
30% Bioavailability (F30%):	0.094

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.754
Plasma Protein Binding (PPB):	96.49938201904297%
Volume Distribution (VD):	2.136
Pgp-substrate:	3.0672919750213623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.411
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.66
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.564

ADMET: Excretion

Clearance (CL):	7.589
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.808
Human Hepatotoxicity (H-HT):	0.975
Drug-inuced Liver Injury (DILI):	0.638
AMES Toxicity:	0.676
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.93
Carcinogencity:	0.821
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC473485

Natural Product ID:	NPC473485
*Common Name:**	XUTWSWVTCRFNFW-KTRKAOTKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XUTWSWVTCRFNFW-KTRKAOTKSA-N
Standard InCHI:	InChI=1S/C35H50O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-33-41-28-26-29-32(21-36,40-29)30(38)34(39)25(19-23(4)27(34)37)35(26,43-33)24(5)20-31(28,42-33)22(2)3/h15-19,24-26,28-30,36,38-39H,2,6-14,20-21H2,1,3-5H3/b16-15+,18-17-/t24-,25-,26-,28-,29+,30-,31-,32+,33-,34-,35+/m1/s1
SMILES:	CCCCCCCCCC/C=C/C=C[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:	CHEMBL443180
PubChem CID:	44559842
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	=	0.02	nmol	PMID[547515]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	50.0	/nmol	PMID[547515]

☑ 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 NPC473485 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	1488
0.2-0.3	4224
0.3-0.4	7204
0.4-0.5	12622
0.5-0.6	10344
0.6-0.7	5260
0.7-0.8	1164
0.8-0.85	55
0.85-0.9	14
0.9-0.95	2
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474508
0.9917	High Similarity	NPC251564
0.9917	High Similarity	NPC475606
0.9917	High Similarity	NPC477189
0.9917	High Similarity	NPC475314
0.9836	High Similarity	NPC471136
0.9836	High Similarity	NPC473548
0.9836	High Similarity	NPC100017
0.9836	High Similarity	NPC182266
0.9836	High Similarity	NPC475500
0.9836	High Similarity	NPC471137
0.9836	High Similarity	NPC223356
0.9836	High Similarity	NPC475154
0.9833	High Similarity	NPC162495
0.9677	High Similarity	NPC68282
0.9672	High Similarity	NPC475139
0.9672	High Similarity	NPC180902
0.9667	High Similarity	NPC475273
0.9667	High Similarity	NPC168849
0.9583	High Similarity	NPC217901
0.9268	High Similarity	NPC476091
0.9268	High Similarity	NPC476078
0.9262	High Similarity	NPC471939
0.9187	High Similarity	NPC471940
0.912	High Similarity	NPC473838
0.912	High Similarity	NPC475389
0.9098	High Similarity	NPC473802
0.9024	High Similarity	NPC473919
0.9024	High Similarity	NPC473709
0.881	High Similarity	NPC236999
0.8699	High Similarity	NPC142882
0.8516	High Similarity	NPC270109
0.8425	Intermediate Similarity	NPC145238
0.8413	Intermediate Similarity	NPC257017
0.8413	Intermediate Similarity	NPC162009
0.8359	Intermediate Similarity	NPC222307
0.8346	Intermediate Similarity	NPC472399
0.8268	Intermediate Similarity	NPC19464
0.8254	Intermediate Similarity	NPC317635
0.8254	Intermediate Similarity	NPC329008
0.8217	Intermediate Similarity	NPC225049
0.8189	Intermediate Similarity	NPC52839
0.8189	Intermediate Similarity	NPC472401
0.8175	Intermediate Similarity	NPC470186
0.8163	Intermediate Similarity	NPC49297
0.8154	Intermediate Similarity	NPC298841
0.8138	Intermediate Similarity	NPC146310
0.811	Intermediate Similarity	NPC19336
0.811	Intermediate Similarity	NPC185876
0.811	Intermediate Similarity	NPC157252
0.811	Intermediate Similarity	NPC472759
0.811	Intermediate Similarity	NPC471126
0.811	Intermediate Similarity	NPC329080
0.811	Intermediate Similarity	NPC471128
0.811	Intermediate Similarity	NPC145182
0.811	Intermediate Similarity	NPC475885
0.8095	Intermediate Similarity	NPC124676
0.8095	Intermediate Similarity	NPC146280
0.8095	Intermediate Similarity	NPC181924
0.806	Intermediate Similarity	NPC471234
0.8047	Intermediate Similarity	NPC102822
0.8047	Intermediate Similarity	NPC477046
0.8045	Intermediate Similarity	NPC471855
0.8031	Intermediate Similarity	NPC255081
0.8031	Intermediate Similarity	NPC275696
0.8031	Intermediate Similarity	NPC471108
0.8031	Intermediate Similarity	NPC156745
0.8031	Intermediate Similarity	NPC22628
0.8031	Intermediate Similarity	NPC180640
0.8031	Intermediate Similarity	NPC5989
0.8031	Intermediate Similarity	NPC5991
0.8031	Intermediate Similarity	NPC236918
0.8015	Intermediate Similarity	NPC42399
0.8	Intermediate Similarity	NPC470922
0.8	Intermediate Similarity	NPC477188
0.8	Intermediate Similarity	NPC43304
0.8	Intermediate Similarity	NPC477190
0.8	Intermediate Similarity	NPC275477
0.797	Intermediate Similarity	NPC476852
0.7969	Intermediate Similarity	NPC143755
0.7969	Intermediate Similarity	NPC472004
0.7955	Intermediate Similarity	NPC473620
0.7953	Intermediate Similarity	NPC472758
0.7953	Intermediate Similarity	NPC471125
0.7953	Intermediate Similarity	NPC284707
0.7953	Intermediate Similarity	NPC472760
0.7953	Intermediate Similarity	NPC472397
0.7953	Intermediate Similarity	NPC171905
0.7947	Intermediate Similarity	NPC322420
0.7941	Intermediate Similarity	NPC243014
0.7939	Intermediate Similarity	NPC181999
0.7939	Intermediate Similarity	NPC473635
0.7937	Intermediate Similarity	NPC477509
0.7929	Intermediate Similarity	NPC471172
0.7923	Intermediate Similarity	NPC469352
0.792	Intermediate Similarity	NPC477126
0.791	Intermediate Similarity	NPC470185
0.7895	Intermediate Similarity	NPC471407
0.7895	Intermediate Similarity	NPC475371
0.7895	Intermediate Similarity	NPC476851
0.7895	Intermediate Similarity	NPC470851
0.7895	Intermediate Similarity	NPC231529
0.7891	Intermediate Similarity	NPC472667
0.7891	Intermediate Similarity	NPC476529
0.7891	Intermediate Similarity	NPC476107
0.7891	Intermediate Similarity	NPC469488
0.7891	Intermediate Similarity	NPC475775
0.7883	Intermediate Similarity	NPC596
0.7879	Intermediate Similarity	NPC287423
0.7879	Intermediate Similarity	NPC470780
0.7874	Intermediate Similarity	NPC477116
0.7874	Intermediate Similarity	NPC53396
0.7874	Intermediate Similarity	NPC156252
0.7874	Intermediate Similarity	NPC10721
0.7874	Intermediate Similarity	NPC474518
0.7874	Intermediate Similarity	NPC27999
0.7874	Intermediate Similarity	NPC98249
0.7874	Intermediate Similarity	NPC153651
0.7872	Intermediate Similarity	NPC194854
0.7872	Intermediate Similarity	NPC48813
0.7863	Intermediate Similarity	NPC24651
0.7857	Intermediate Similarity	NPC73314
0.7852	Intermediate Similarity	NPC168879
0.7843	Intermediate Similarity	NPC61891
0.7836	Intermediate Similarity	NPC476863
0.7836	Intermediate Similarity	NPC471170
0.7836	Intermediate Similarity	NPC476855
0.7836	Intermediate Similarity	NPC476862
0.7829	Intermediate Similarity	NPC475003
0.7829	Intermediate Similarity	NPC48692
0.7829	Intermediate Similarity	NPC112038
0.7829	Intermediate Similarity	NPC109607
0.7829	Intermediate Similarity	NPC107338
0.782	Intermediate Similarity	NPC476859
0.782	Intermediate Similarity	NPC470850
0.7817	Intermediate Similarity	NPC475462
0.7817	Intermediate Similarity	NPC16729
0.7812	Intermediate Similarity	NPC204552
0.7812	Intermediate Similarity	NPC188667
0.781	Intermediate Similarity	NPC141215
0.781	Intermediate Similarity	NPC471089
0.781	Intermediate Similarity	NPC190065
0.7805	Intermediate Similarity	NPC29827
0.7803	Intermediate Similarity	NPC293112
0.7795	Intermediate Similarity	NPC154363
0.7795	Intermediate Similarity	NPC471127
0.7795	Intermediate Similarity	NPC234858
0.7794	Intermediate Similarity	NPC242486
0.7794	Intermediate Similarity	NPC15215
0.7786	Intermediate Similarity	NPC18945
0.7786	Intermediate Similarity	NPC91693
0.7786	Intermediate Similarity	NPC265557
0.7786	Intermediate Similarity	NPC5153
0.7786	Intermediate Similarity	NPC48414
0.7786	Intermediate Similarity	NPC67251
0.7786	Intermediate Similarity	NPC11895
0.7786	Intermediate Similarity	NPC105926
0.7786	Intermediate Similarity	NPC471392
0.7778	Intermediate Similarity	NPC477091
0.7778	Intermediate Similarity	NPC254614
0.7778	Intermediate Similarity	NPC254146
0.7778	Intermediate Similarity	NPC231240
0.7778	Intermediate Similarity	NPC100390
0.7778	Intermediate Similarity	NPC469454
0.7778	Intermediate Similarity	NPC6274
0.7778	Intermediate Similarity	NPC472769
0.7778	Intermediate Similarity	NPC102316
0.7778	Intermediate Similarity	NPC33378
0.7778	Intermediate Similarity	NPC474937
0.7778	Intermediate Similarity	NPC469496
0.7778	Intermediate Similarity	NPC469463
0.7769	Intermediate Similarity	NPC470779
0.7769	Intermediate Similarity	NPC310511
0.7769	Intermediate Similarity	NPC204731
0.7761	Intermediate Similarity	NPC470880
0.7761	Intermediate Similarity	NPC476854
0.7761	Intermediate Similarity	NPC104382
0.7761	Intermediate Similarity	NPC175186
0.7761	Intermediate Similarity	NPC473593
0.7761	Intermediate Similarity	NPC476966
0.7754	Intermediate Similarity	NPC140045
0.7754	Intermediate Similarity	NPC295885
0.7752	Intermediate Similarity	NPC9674
0.7752	Intermediate Similarity	NPC19028
0.7744	Intermediate Similarity	NPC473253
0.7744	Intermediate Similarity	NPC470882
0.7744	Intermediate Similarity	NPC305496
0.7744	Intermediate Similarity	NPC476008
0.7737	Intermediate Similarity	NPC262813
0.7734	Intermediate Similarity	NPC97908
0.7734	Intermediate Similarity	NPC122033
0.7734	Intermediate Similarity	NPC287343
0.7734	Intermediate Similarity	NPC469684
0.7734	Intermediate Similarity	NPC23046
0.7734	Intermediate Similarity	NPC470854
0.7734	Intermediate Similarity	NPC474654
0.7727	Intermediate Similarity	NPC324769
0.7727	Intermediate Similarity	NPC8369
0.7727	Intermediate Similarity	NPC75856
0.7727	Intermediate Similarity	NPC476729

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 NPC473485 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1596
0.2-0.3	3724
0.3-0.4	2368
0.4-0.5	727
0.5-0.6	317
0.6-0.7	157
0.7-0.8	16
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
0.7692	Intermediate Similarity	NPD6054	Approved
0.7581	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD8515	Approved
0.75	Intermediate Similarity	NPD6015	Approved
0.75	Intermediate Similarity	NPD8516	Approved
0.75	Intermediate Similarity	NPD8513	Phase 3
0.75	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD8517	Approved
0.75	Intermediate Similarity	NPD7319	Approved
0.7463	Intermediate Similarity	NPD7492	Approved
0.7444	Intermediate Similarity	NPD5988	Approved
0.7426	Intermediate Similarity	NPD7736	Approved
0.7424	Intermediate Similarity	NPD6059	Approved
0.7407	Intermediate Similarity	NPD6616	Approved
0.7381	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7078	Approved
0.7279	Intermediate Similarity	NPD7507	Approved
0.7226	Intermediate Similarity	NPD8074	Phase 3
0.7226	Intermediate Similarity	NPD8293	Discontinued
0.7197	Intermediate Similarity	NPD7115	Discovery
0.7164	Intermediate Similarity	NPD6319	Approved
0.7132	Intermediate Similarity	NPD6371	Approved
0.7132	Intermediate Similarity	NPD8328	Phase 3
0.709	Intermediate Similarity	NPD7516	Approved
0.704	Intermediate Similarity	NPD5344	Discontinued
0.7023	Intermediate Similarity	NPD6882	Approved
0.7023	Intermediate Similarity	NPD8297	Approved
0.7015	Intermediate Similarity	NPD7328	Approved
0.7015	Intermediate Similarity	NPD7327	Approved
0.7014	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6686	Approved
0.696	Remote Similarity	NPD6648	Approved
0.6947	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6009	Approved
0.6929	Remote Similarity	NPD6033	Approved
0.6923	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4634	Approved
0.6861	Remote Similarity	NPD8380	Approved
0.6861	Remote Similarity	NPD8378	Approved
0.6861	Remote Similarity	NPD8033	Approved
0.6861	Remote Similarity	NPD8379	Approved
0.6861	Remote Similarity	NPD8296	Approved
0.6861	Remote Similarity	NPD7503	Approved
0.6861	Remote Similarity	NPD8335	Approved
0.6861	Remote Similarity	NPD6921	Approved
0.6842	Remote Similarity	NPD4632	Approved
0.6818	Remote Similarity	NPD6649	Approved
0.6818	Remote Similarity	NPD6650	Approved
0.6815	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD8294	Approved
0.6788	Remote Similarity	NPD8377	Approved
0.6774	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7830	Approved
0.6763	Remote Similarity	NPD7829	Approved
0.6746	Remote Similarity	NPD4225	Approved
0.6721	Remote Similarity	NPD46	Approved
0.6721	Remote Similarity	NPD7838	Discovery
0.6721	Remote Similarity	NPD6698	Approved
0.6718	Remote Similarity	NPD6881	Approved
0.6718	Remote Similarity	NPD6899	Approved
0.6694	Remote Similarity	NPD5282	Discontinued
0.6692	Remote Similarity	NPD8130	Phase 1
0.6692	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7604	Phase 2
0.6642	Remote Similarity	NPD6053	Discontinued
0.6641	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6412	Phase 2
0.6641	Remote Similarity	NPD5697	Approved
0.6617	Remote Similarity	NPD7102	Approved
0.6617	Remote Similarity	NPD7290	Approved
0.6617	Remote Similarity	NPD6883	Approved
0.6593	Remote Similarity	NPD8133	Approved
0.6591	Remote Similarity	NPD7320	Approved
0.6589	Remote Similarity	NPD5211	Phase 2
0.6567	Remote Similarity	NPD6847	Approved
0.6567	Remote Similarity	NPD6869	Approved
0.6567	Remote Similarity	NPD6617	Approved
0.6565	Remote Similarity	NPD7128	Approved
0.6565	Remote Similarity	NPD6402	Approved
0.6565	Remote Similarity	NPD5739	Approved
0.6565	Remote Similarity	NPD6675	Approved
0.6562	Remote Similarity	NPD5286	Approved
0.6562	Remote Similarity	NPD5285	Approved
0.6562	Remote Similarity	NPD4696	Approved
0.6552	Remote Similarity	NPD7260	Phase 2
0.6541	Remote Similarity	NPD6012	Approved
0.6541	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6013	Approved
0.6541	Remote Similarity	NPD6014	Approved
0.6525	Remote Similarity	NPD7642	Approved
0.6507	Remote Similarity	NPD8338	Approved
0.6504	Remote Similarity	NPD1695	Approved
0.65	Remote Similarity	NPD5983	Phase 2
0.6489	Remote Similarity	NPD5141	Approved
0.6488	Remote Similarity	NPD7799	Discontinued
0.6483	Remote Similarity	NPD5956	Approved
0.648	Remote Similarity	NPD5778	Approved
0.648	Remote Similarity	NPD5779	Approved
0.6466	Remote Similarity	NPD6011	Approved
0.6462	Remote Similarity	NPD4633	Approved
0.6462	Remote Similarity	NPD5225	Approved
0.6462	Remote Similarity	NPD5224	Approved
0.6462	Remote Similarity	NPD5226	Approved
0.6434	Remote Similarity	NPD8451	Approved
0.6434	Remote Similarity	NPD6336	Discontinued
0.6416	Remote Similarity	NPD8407	Phase 2
0.6412	Remote Similarity	NPD5175	Approved
0.6412	Remote Similarity	NPD5174	Approved
0.6406	Remote Similarity	NPD4755	Approved
0.6395	Remote Similarity	NPD6845	Suspended
0.6391	Remote Similarity	NPD5701	Approved
0.6389	Remote Similarity	NPD8448	Approved
0.6385	Remote Similarity	NPD5223	Approved
0.6357	Remote Similarity	NPD7638	Approved
0.6343	Remote Similarity	NPD4730	Approved
0.6343	Remote Similarity	NPD4729	Approved
0.6337	Remote Similarity	NPD8368	Discontinued
0.6328	Remote Similarity	NPD7839	Suspended
0.6308	Remote Similarity	NPD4700	Approved
0.6308	Remote Similarity	NPD7640	Approved
0.6308	Remote Similarity	NPD7639	Approved
0.6268	Remote Similarity	NPD8444	Approved
0.6268	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.626	Remote Similarity	NPD1700	Approved
0.6259	Remote Similarity	NPD8392	Approved
0.6259	Remote Similarity	NPD8391	Approved
0.6259	Remote Similarity	NPD8390	Approved
0.625	Remote Similarity	NPD8299	Approved
0.625	Remote Similarity	NPD8342	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD8341	Approved
0.625	Remote Similarity	NPD8340	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5251	Approved
0.6241	Remote Similarity	NPD7101	Approved
0.6241	Remote Similarity	NPD7100	Approved
0.624	Remote Similarity	NPD6101	Approved
0.624	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8273	Phase 1
0.6204	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD5221	Approved
0.6202	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD5222	Approved
0.62	Remote Similarity	NPD8415	Approved
0.6194	Remote Similarity	NPD4768	Approved
0.6194	Remote Similarity	NPD4767	Approved
0.6181	Remote Similarity	NPD6067	Discontinued
0.617	Remote Similarity	NPD7641	Discontinued
0.617	Remote Similarity	NPD6335	Approved
0.6159	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8266	Approved
0.6154	Remote Similarity	NPD8267	Approved
0.6154	Remote Similarity	NPD5173	Approved
0.6154	Remote Similarity	NPD8268	Approved
0.6154	Remote Similarity	NPD8269	Approved
0.6143	Remote Similarity	NPD6274	Approved
0.6142	Remote Similarity	NPD6079	Approved
0.6142	Remote Similarity	NPD6411	Approved
0.6122	Remote Similarity	NPD8336	Approved
0.6122	Remote Similarity	NPD8337	Approved
0.6119	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8080	Discontinued
0.6103	Remote Similarity	NPD5128	Approved
0.6099	Remote Similarity	NPD6317	Approved
0.6087	Remote Similarity	NPD5216	Approved
0.6087	Remote Similarity	NPD5217	Approved
0.6087	Remote Similarity	NPD5215	Approved
0.6077	Remote Similarity	NPD4697	Phase 3
0.6067	Remote Similarity	NPD8434	Phase 2
0.6056	Remote Similarity	NPD6314	Approved
0.6056	Remote Similarity	NPD6313	Approved
0.6048	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD4754	Approved
0.6031	Remote Similarity	NPD6084	Phase 2
0.6031	Remote Similarity	NPD6083	Phase 2
0.6016	Remote Similarity	NPD7637	Suspended
0.6014	Remote Similarity	NPD5169	Approved
0.6014	Remote Similarity	NPD5135	Approved
0.6014	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8361	Approved
0.6	Remote Similarity	NPD8360	Approved
0.6	Remote Similarity	NPD4629	Approved
0.6	Remote Similarity	NPD8435	Approved
0.6	Remote Similarity	NPD5210	Approved
0.5984	Remote Similarity	NPD5328	Approved
0.5977	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD5127	Approved
0.5952	Remote Similarity	NPD7524	Approved
0.5938	Remote Similarity	NPD3168	Discontinued
0.5938	Remote Similarity	NPD5785	Approved
0.5934	Remote Similarity	NPD7879	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