NPASS Compound

Structure

NPC251564 OpenBabel07101718322D 38 43 0 0 1 0 0 0 0 0999 V2000 -1.8369 8.0510 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 -2.1452 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 17 2 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 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 2 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 26 1 0 0 0 0 16 31 1 0 0 0 0 18 22 1 0 0 0 0 19 30 1 1 0 0 0 20 29 1 6 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 21 30 1 1 0 0 0 22 29 1 0 0 0 0 22 32 2 0 0 0 0 23 26 1 6 0 0 0 23 36 1 0 0 0 0 24 27 1 1 0 0 0 24 35 1 0 0 0 0 25 27 1 6 0 0 0 25 29 1 0 0 0 0 25 33 1 0 0 0 0 26 17 1 1 0 0 0 26 37 1 0 0 0 0 27 16 1 6 0 0 0 27 35 1 0 0 0 0 28 13 1 6 0 0 0 28 36 1 0 0 0 0 28 37 1 0 0 0 0 28 38 1 0 0 0 0 29 34 1 6 0 0 0 30 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.27
Volume:	533.237
LogP:	3.789
LogD:	3.219
LogS:	-3.916
# Rotatable Bonds:	8
TPSA:	117.98
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.191
Synthetic Accessibility Score:	6.734
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825
MDCK Permeability:	2.222114744654391e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.578
30% Bioavailability (F30%):	0.332

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.767
Plasma Protein Binding (PPB):	85.8841323852539%
Volume Distribution (VD):	1.946
Pgp-substrate:	10.883159637451172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.299
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.799
CYP3A4-substrate:	0.567

ADMET: Excretion

Clearance (CL):	6.08
Half-life (T1/2):	0.535

ADMET: Toxicity

hERG Blockers:	0.655
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.738
AMES Toxicity:	0.8
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.9
Carcinogencity:	0.851
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: NPC251564

Natural Product ID:	NPC251564
*Common Name:**	CZCPFHFUOUQBDL-OCLYYHQSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CZCPFHFUOUQBDL-OCLYYHQSSA-N
Standard InCHI:	InChI=1S/C30H40O8/c1-6-7-8-9-10-11-12-13-28-36-23-21-24-27(16-31,35-24)25(33)29(34)20(14-18(4)22(29)32)30(21,38-28)19(5)15-26(23,37-28)17(2)3/h10-14,19-21,23-25,31,33-34H,2,6-9,15-16H2,1,3-5H3/b11-10+,13-12-/t19-,20-,21-,23-,24+,25-,26-,27+,28-,29-,30+/m1/s1
SMILES:	CCCCC/C=C/C=C[C@@]12O[C@@H]3[C@@H]4[C@H]5[C@@](CO)([C@H]([C@]6([C@@H](C=C(C)C6=O)[C@]4([C@H](C)C[C@]3(C(=C)C)O1)O2)O)O)O5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453030
PubChem CID:	44559841
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	=	0.15	nmol	PMID[448487]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	6.7	/nmol	PMID[448487]

☑ 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 NPC251564 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	284
0.1-0.2	1459
0.2-0.3	4172
0.3-0.4	7133
0.4-0.5	12472
0.5-0.6	10708
0.6-0.7	5181
0.7-0.8	1173
0.8-0.85	64
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	NPC475314
1.0	High Similarity	NPC475606
1.0	High Similarity	NPC477189
0.9917	High Similarity	NPC474508
0.9917	High Similarity	NPC473485
0.9754	High Similarity	NPC475500
0.9754	High Similarity	NPC475154
0.9754	High Similarity	NPC223356
0.9754	High Similarity	NPC471136
0.9754	High Similarity	NPC473548
0.9754	High Similarity	NPC182266
0.9754	High Similarity	NPC100017
0.9754	High Similarity	NPC471137
0.975	High Similarity	NPC162495
0.9664	High Similarity	NPC217901
0.9597	High Similarity	NPC68282
0.959	High Similarity	NPC180902
0.959	High Similarity	NPC475139
0.9583	High Similarity	NPC475273
0.9583	High Similarity	NPC168849
0.9187	High Similarity	NPC476078
0.9187	High Similarity	NPC476091
0.918	High Similarity	NPC471939
0.9106	High Similarity	NPC471940
0.904	High Similarity	NPC475389
0.904	High Similarity	NPC473838
0.9016	High Similarity	NPC473802
0.8943	High Similarity	NPC473709
0.8943	High Similarity	NPC473919
0.877	High Similarity	NPC142882
0.873	High Similarity	NPC236999
0.8583	High Similarity	NPC270109
0.8425	Intermediate Similarity	NPC222307
0.8413	Intermediate Similarity	NPC472399
0.8346	Intermediate Similarity	NPC145238
0.8333	Intermediate Similarity	NPC257017
0.8333	Intermediate Similarity	NPC162009
0.832	Intermediate Similarity	NPC317635
0.832	Intermediate Similarity	NPC329008
0.8281	Intermediate Similarity	NPC225049
0.8254	Intermediate Similarity	NPC472401
0.8194	Intermediate Similarity	NPC146310
0.8189	Intermediate Similarity	NPC19464
0.8175	Intermediate Similarity	NPC471128
0.8175	Intermediate Similarity	NPC475885
0.8175	Intermediate Similarity	NPC157252
0.8175	Intermediate Similarity	NPC145182
0.8175	Intermediate Similarity	NPC471126
0.8151	Intermediate Similarity	NPC181924
0.812	Intermediate Similarity	NPC471234
0.811	Intermediate Similarity	NPC477046
0.811	Intermediate Similarity	NPC102822
0.811	Intermediate Similarity	NPC52839
0.8095	Intermediate Similarity	NPC49297
0.8095	Intermediate Similarity	NPC470186
0.8095	Intermediate Similarity	NPC236918
0.8095	Intermediate Similarity	NPC156745
0.8077	Intermediate Similarity	NPC298841
0.8062	Intermediate Similarity	NPC470922
0.8031	Intermediate Similarity	NPC185876
0.8031	Intermediate Similarity	NPC19336
0.8031	Intermediate Similarity	NPC329080
0.8031	Intermediate Similarity	NPC472004
0.8031	Intermediate Similarity	NPC472759
0.8031	Intermediate Similarity	NPC143755
0.803	Intermediate Similarity	NPC476852
0.8016	Intermediate Similarity	NPC171905
0.8016	Intermediate Similarity	NPC472397
0.8016	Intermediate Similarity	NPC471125
0.8016	Intermediate Similarity	NPC472758
0.8016	Intermediate Similarity	NPC146280
0.8016	Intermediate Similarity	NPC284707
0.8016	Intermediate Similarity	NPC124676
0.8015	Intermediate Similarity	NPC473620
0.8	Intermediate Similarity	NPC181999
0.8	Intermediate Similarity	NPC243014
0.8	Intermediate Similarity	NPC477509
0.7984	Intermediate Similarity	NPC477126
0.7984	Intermediate Similarity	NPC469352
0.797	Intermediate Similarity	NPC471855
0.7955	Intermediate Similarity	NPC470851
0.7955	Intermediate Similarity	NPC476851
0.7955	Intermediate Similarity	NPC231529
0.7955	Intermediate Similarity	NPC475371
0.7953	Intermediate Similarity	NPC472667
0.7953	Intermediate Similarity	NPC475775
0.7953	Intermediate Similarity	NPC22628
0.7953	Intermediate Similarity	NPC471108
0.7953	Intermediate Similarity	NPC476529
0.7953	Intermediate Similarity	NPC180640
0.7953	Intermediate Similarity	NPC275696
0.7953	Intermediate Similarity	NPC476107
0.7953	Intermediate Similarity	NPC469488
0.7953	Intermediate Similarity	NPC5991
0.7953	Intermediate Similarity	NPC5989
0.7953	Intermediate Similarity	NPC255081
0.7939	Intermediate Similarity	NPC287423
0.7939	Intermediate Similarity	NPC42399
0.7939	Intermediate Similarity	NPC470780
0.7937	Intermediate Similarity	NPC156252
0.7937	Intermediate Similarity	NPC53396
0.7937	Intermediate Similarity	NPC474518
0.7937	Intermediate Similarity	NPC98249
0.7937	Intermediate Similarity	NPC27999
0.7937	Intermediate Similarity	NPC477116
0.7933	Intermediate Similarity	NPC275477
0.7933	Intermediate Similarity	NPC477188
0.7933	Intermediate Similarity	NPC43304
0.7933	Intermediate Similarity	NPC477190
0.7923	Intermediate Similarity	NPC24651
0.791	Intermediate Similarity	NPC168879
0.7895	Intermediate Similarity	NPC476863
0.7895	Intermediate Similarity	NPC476855
0.7895	Intermediate Similarity	NPC476862
0.7891	Intermediate Similarity	NPC112038
0.7891	Intermediate Similarity	NPC107338
0.7891	Intermediate Similarity	NPC475003
0.7891	Intermediate Similarity	NPC109607
0.7881	Intermediate Similarity	NPC322420
0.7879	Intermediate Similarity	NPC476859
0.7879	Intermediate Similarity	NPC470850
0.7874	Intermediate Similarity	NPC472760
0.7874	Intermediate Similarity	NPC204552
0.7874	Intermediate Similarity	NPC188667
0.7869	Intermediate Similarity	NPC29827
0.7863	Intermediate Similarity	NPC473635
0.7863	Intermediate Similarity	NPC293112
0.7857	Intermediate Similarity	NPC154363
0.7857	Intermediate Similarity	NPC234858
0.7857	Intermediate Similarity	NPC471172
0.7857	Intermediate Similarity	NPC471127
0.7852	Intermediate Similarity	NPC242486
0.7852	Intermediate Similarity	NPC15215
0.7846	Intermediate Similarity	NPC471392
0.7846	Intermediate Similarity	NPC91693
0.7846	Intermediate Similarity	NPC11895
0.7846	Intermediate Similarity	NPC18945
0.7846	Intermediate Similarity	NPC105926
0.7846	Intermediate Similarity	NPC265557
0.7846	Intermediate Similarity	NPC67251
0.784	Intermediate Similarity	NPC469463
0.784	Intermediate Similarity	NPC469454
0.784	Intermediate Similarity	NPC469496
0.7836	Intermediate Similarity	NPC33378
0.7836	Intermediate Similarity	NPC102316
0.7836	Intermediate Similarity	NPC254614
0.7836	Intermediate Similarity	NPC100390
0.7836	Intermediate Similarity	NPC254146
0.7836	Intermediate Similarity	NPC6274
0.7836	Intermediate Similarity	NPC470185
0.7829	Intermediate Similarity	NPC310511
0.7829	Intermediate Similarity	NPC470779
0.782	Intermediate Similarity	NPC471407
0.782	Intermediate Similarity	NPC175186
0.782	Intermediate Similarity	NPC473593
0.782	Intermediate Similarity	NPC470880
0.782	Intermediate Similarity	NPC104382
0.782	Intermediate Similarity	NPC476854
0.7812	Intermediate Similarity	NPC9674
0.7812	Intermediate Similarity	NPC19028
0.781	Intermediate Similarity	NPC596
0.7803	Intermediate Similarity	NPC476008
0.7803	Intermediate Similarity	NPC470882
0.7803	Intermediate Similarity	NPC473253
0.7803	Intermediate Similarity	NPC305496
0.7801	Intermediate Similarity	NPC48813
0.7801	Intermediate Similarity	NPC194854
0.7795	Intermediate Similarity	NPC97908
0.7795	Intermediate Similarity	NPC474654
0.7795	Intermediate Similarity	NPC122033
0.7795	Intermediate Similarity	NPC470854
0.7795	Intermediate Similarity	NPC23046
0.7795	Intermediate Similarity	NPC10721
0.7795	Intermediate Similarity	NPC469684
0.7795	Intermediate Similarity	NPC287343
0.7795	Intermediate Similarity	NPC153651
0.7787	Intermediate Similarity	NPC474716
0.7786	Intermediate Similarity	NPC8369
0.7786	Intermediate Similarity	NPC476729
0.7786	Intermediate Similarity	NPC81736
0.7786	Intermediate Similarity	NPC172154
0.7778	Intermediate Similarity	NPC238667
0.7778	Intermediate Similarity	NPC73314
0.7778	Intermediate Similarity	NPC88668
0.7778	Intermediate Similarity	NPC61891
0.7778	Intermediate Similarity	NPC472400
0.7778	Intermediate Similarity	NPC474872
0.7769	Intermediate Similarity	NPC170538
0.7769	Intermediate Similarity	NPC474741
0.7769	Intermediate Similarity	NPC222688
0.7769	Intermediate Similarity	NPC312833
0.7761	Intermediate Similarity	NPC471170
0.776	Intermediate Similarity	NPC475391
0.7752	Intermediate Similarity	NPC4548
0.7752	Intermediate Similarity	NPC48692
0.7746	Intermediate Similarity	NPC475462
0.7746	Intermediate Similarity	NPC16729
0.7744	Intermediate Similarity	NPC311534
0.7744	Intermediate Similarity	NPC473888
0.7742	Intermediate Similarity	NPC46407

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 NPC251564 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	1574
0.2-0.3	3690
0.3-0.4	2412
0.4-0.5	735
0.5-0.6	327
0.6-0.7	153
0.7-0.8	18
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
0.7752	Intermediate Similarity	NPD6054	Approved
0.7634	Intermediate Similarity	NPD6370	Approved
0.7557	Intermediate Similarity	NPD6016	Approved
0.7557	Intermediate Similarity	NPD6015	Approved
0.7556	Intermediate Similarity	NPD7319	Approved
0.7519	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD5988	Approved
0.75	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD6059	Approved
0.7463	Intermediate Similarity	NPD6616	Approved
0.744	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD8516	Approved
0.7424	Intermediate Similarity	NPD8515	Approved
0.7424	Intermediate Similarity	NPD8517	Approved
0.7424	Intermediate Similarity	NPD8513	Phase 3
0.7407	Intermediate Similarity	NPD7078	Approved
0.7353	Intermediate Similarity	NPD7736	Approved
0.7333	Intermediate Similarity	NPD7507	Approved
0.7252	Intermediate Similarity	NPD7115	Discovery
0.7218	Intermediate Similarity	NPD6319	Approved
0.7188	Intermediate Similarity	NPD6371	Approved
0.7153	Intermediate Similarity	NPD8074	Phase 3
0.7153	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD7516	Approved
0.7097	Intermediate Similarity	NPD5344	Discontinued
0.7077	Intermediate Similarity	NPD6882	Approved
0.7068	Intermediate Similarity	NPD7327	Approved
0.7068	Intermediate Similarity	NPD7328	Approved
0.7059	Intermediate Similarity	NPD8328	Phase 3
0.7031	Intermediate Similarity	NPD6686	Approved
0.7016	Intermediate Similarity	NPD6648	Approved
0.6992	Remote Similarity	NPD6009	Approved
0.6978	Remote Similarity	NPD6033	Approved
0.6977	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8297	Approved
0.6944	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4634	Approved
0.6923	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7503	Approved
0.6912	Remote Similarity	NPD6921	Approved
0.6894	Remote Similarity	NPD4632	Approved
0.687	Remote Similarity	NPD6650	Approved
0.687	Remote Similarity	NPD6649	Approved
0.687	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4225	Approved
0.6788	Remote Similarity	NPD8380	Approved
0.6788	Remote Similarity	NPD8335	Approved
0.6788	Remote Similarity	NPD8296	Approved
0.6788	Remote Similarity	NPD8378	Approved
0.6788	Remote Similarity	NPD8379	Approved
0.6788	Remote Similarity	NPD8033	Approved
0.6777	Remote Similarity	NPD46	Approved
0.6777	Remote Similarity	NPD6698	Approved
0.6769	Remote Similarity	NPD6899	Approved
0.6769	Remote Similarity	NPD6881	Approved
0.6748	Remote Similarity	NPD5282	Discontinued
0.6744	Remote Similarity	NPD6008	Approved
0.6741	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6373	Approved
0.6718	Remote Similarity	NPD6372	Approved
0.6715	Remote Similarity	NPD8294	Approved
0.6715	Remote Similarity	NPD8377	Approved
0.6692	Remote Similarity	NPD6412	Phase 2
0.6692	Remote Similarity	NPD5697	Approved
0.6692	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6053	Discontinued
0.6691	Remote Similarity	NPD7604	Phase 2
0.6691	Remote Similarity	NPD7830	Approved
0.6691	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6641	Remote Similarity	NPD5211	Phase 2
0.6641	Remote Similarity	NPD7320	Approved
0.6639	Remote Similarity	NPD7838	Discovery
0.6617	Remote Similarity	NPD6847	Approved
0.6617	Remote Similarity	NPD6617	Approved
0.6617	Remote Similarity	NPD8130	Phase 1
0.6617	Remote Similarity	NPD6869	Approved
0.6615	Remote Similarity	NPD6675	Approved
0.6615	Remote Similarity	NPD7128	Approved
0.6615	Remote Similarity	NPD6402	Approved
0.6615	Remote Similarity	NPD5739	Approved
0.6614	Remote Similarity	NPD5285	Approved
0.6614	Remote Similarity	NPD5286	Approved
0.6614	Remote Similarity	NPD4696	Approved
0.6608	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7260	Phase 2
0.6591	Remote Similarity	NPD6014	Approved
0.6591	Remote Similarity	NPD6013	Approved
0.6591	Remote Similarity	NPD6012	Approved
0.6585	Remote Similarity	NPD7983	Approved
0.6571	Remote Similarity	NPD7642	Approved
0.6557	Remote Similarity	NPD1695	Approved
0.6547	Remote Similarity	NPD5983	Phase 2
0.6538	Remote Similarity	NPD5141	Approved
0.6532	Remote Similarity	NPD5778	Approved
0.6532	Remote Similarity	NPD5779	Approved
0.6528	Remote Similarity	NPD5956	Approved
0.6519	Remote Similarity	NPD8133	Approved
0.6515	Remote Similarity	NPD6011	Approved
0.6512	Remote Similarity	NPD5225	Approved
0.6512	Remote Similarity	NPD5226	Approved
0.6512	Remote Similarity	NPD4633	Approved
0.6512	Remote Similarity	NPD5224	Approved
0.6479	Remote Similarity	NPD6336	Discontinued
0.6466	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5175	Approved
0.6462	Remote Similarity	NPD5174	Approved
0.6457	Remote Similarity	NPD4755	Approved
0.6439	Remote Similarity	NPD5701	Approved
0.6438	Remote Similarity	NPD8338	Approved
0.6438	Remote Similarity	NPD6845	Suspended
0.6434	Remote Similarity	NPD5223	Approved
0.6429	Remote Similarity	NPD7799	Discontinued
0.6406	Remote Similarity	NPD7638	Approved
0.6391	Remote Similarity	NPD4729	Approved
0.6391	Remote Similarity	NPD4730	Approved
0.6364	Remote Similarity	NPD8451	Approved
0.6358	Remote Similarity	NPD8407	Phase 2
0.6357	Remote Similarity	NPD7639	Approved
0.6357	Remote Similarity	NPD4700	Approved
0.6357	Remote Similarity	NPD7640	Approved
0.6319	Remote Similarity	NPD8448	Approved
0.6312	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD1700	Approved
0.6296	Remote Similarity	NPD5248	Approved
0.6296	Remote Similarity	NPD5249	Phase 3
0.6296	Remote Similarity	NPD5250	Approved
0.6296	Remote Similarity	NPD5251	Approved
0.6296	Remote Similarity	NPD5247	Approved
0.629	Remote Similarity	NPD6101	Approved
0.629	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7101	Approved
0.6286	Remote Similarity	NPD7100	Approved
0.6279	Remote Similarity	NPD8368	Discontinued
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7839	Suspended
0.6241	Remote Similarity	NPD4768	Approved
0.6241	Remote Similarity	NPD4767	Approved
0.6224	Remote Similarity	NPD6067	Discontinued
0.6214	Remote Similarity	NPD6335	Approved
0.6214	Remote Similarity	NPD7641	Discontinued
0.6202	Remote Similarity	NPD5173	Approved
0.6197	Remote Similarity	NPD8444	Approved
0.619	Remote Similarity	NPD8390	Approved
0.619	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD8392	Approved
0.619	Remote Similarity	NPD8391	Approved
0.619	Remote Similarity	NPD6079	Approved
0.6187	Remote Similarity	NPD6274	Approved
0.6181	Remote Similarity	NPD8299	Approved
0.6181	Remote Similarity	NPD8342	Approved
0.6181	Remote Similarity	NPD8340	Approved
0.6181	Remote Similarity	NPD8341	Approved
0.6148	Remote Similarity	NPD5128	Approved
0.6143	Remote Similarity	NPD6317	Approved
0.6138	Remote Similarity	NPD8273	Phase 1
0.6133	Remote Similarity	NPD8415	Approved
0.6131	Remote Similarity	NPD5215	Approved
0.6131	Remote Similarity	NPD5216	Approved
0.6131	Remote Similarity	NPD5217	Approved
0.6124	Remote Similarity	NPD4697	Phase 3
0.6099	Remote Similarity	NPD6313	Approved
0.6099	Remote Similarity	NPD6314	Approved
0.6098	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.609	Remote Similarity	NPD4754	Approved
0.6084	Remote Similarity	NPD8266	Approved
0.6084	Remote Similarity	NPD8268	Approved
0.6084	Remote Similarity	NPD8267	Approved
0.6084	Remote Similarity	NPD8269	Approved
0.6077	Remote Similarity	NPD6084	Phase 2
0.6077	Remote Similarity	NPD6083	Phase 2
0.6063	Remote Similarity	NPD7637	Suspended
0.6058	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5169	Approved
0.6058	Remote Similarity	NPD5135	Approved
0.6054	Remote Similarity	NPD8336	Approved
0.6054	Remote Similarity	NPD8337	Approved
0.6047	Remote Similarity	NPD5210	Approved
0.6047	Remote Similarity	NPD4629	Approved
0.6045	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8080	Discontinued
0.6032	Remote Similarity	NPD5328	Approved
0.6014	Remote Similarity	NPD5127	Approved
0.6011	Remote Similarity	NPD8434	Phase 2
0.6	Remote Similarity	NPD7524	Approved
0.5984	Remote Similarity	NPD3168	Discontinued
0.5984	Remote Similarity	NPD5785	Approved
0.5972	Remote Similarity	NPD6908	Approved
0.5972	Remote Similarity	NPD6909	Approved
0.5968	Remote Similarity	NPD1696	Phase 3
0.5968	Remote Similarity	NPD1694	Approved
0.5957	Remote Similarity	NPD6868	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