NPASS Compound

Structure

NPC470735 OpenBabel07101718182D 35 39 0 0 1 0 0 0 0 0999 V2000 4.8936 -1.3112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6637 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7577 -2.7577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0683 -2.0683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9518 -1.5636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6887 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6995 -2.5054 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3775 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3206 -1.1265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5331 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3889 -3.1948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 -0.4875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1762 1.8194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2624 -0.8742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9418 0.2523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 12 1 0 0 0 0 5 15 2 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 24 1 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 1 1 6 0 0 0 11 14 1 0 0 0 0 11 34 1 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 26 1 6 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 34 1 0 0 0 0 16 35 1 1 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 28 2 0 0 0 0 20 29 2 0 0 0 0 21 22 1 0 0 0 0 21 23 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 2 1 6 0 0 0 23 32 1 0 0 0 0 24 25 1 1 0 0 0 24 33 1 0 0 0 0 25 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.15
Volume:	464.984
LogP:	1.261
LogD:	0.343
LogS:	-3.555
# Rotatable Bonds:	2
TPSA:	170.82
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	5.181
Fsp3:	0.48
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.922
MDCK Permeability:	8.218454240704887e-06
Pgp-inhibitor:	0.417
Pgp-substrate:	0.83
Human Intestinal Absorption (HIA):	0.788
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	92.80107879638672%
Volume Distribution (VD):	0.922
Pgp-substrate:	4.178870677947998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.132
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.488
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	4.174
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.27
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.96
Rat Oral Acute Toxicity:	0.902
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.521
Carcinogencity:	0.873
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.578

Download Data

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

Natural Product: NPC470735

Natural Product ID:	NPC470735
*Common Name:**	Sakyomicin A
IUPAC Name:	(2S,3R,4aR,12bS)-2,3,4a,8-tetrahydroxy-12b-[(2R,5R,6R)-5-hydroxy-6-methyloxan-2-yl]oxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
Synonyms:	Sakyomicin A
Standard InCHIKey:	CKZNKYSWWCSICZ-OOTOCDODSA-N
Standard InCHI:	InChI=1S/C25H26O10/c1-11-14(26)6-7-16(34-11)35-25-18-13(19(28)17-12(20(18)29)4-3-5-15(17)27)8-9-24(25,33)10-23(2,32)21(30)22(25)31/h3-5,8-9,11,14,16,21,26-27,30,32-33H,6-7,10H2,1-2H3/t11-,14-,16-,21-,23-,24+,25-/m1/s1
SMILES:	CC1C(CCC(O1)OC23C(=O)C(C(CC2(C=CC4=C3C(=O)C5=C(C4=O)C(=CC=C5)O)O)(C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208051
PubChem CID:	71450742
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001600] Anthraquinone glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33103	amycolatopsis sp. hca1	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23131338]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	34870.0	nM	PMID[465689]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	15060.0	nM	PMID[465689]

☑ 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 NPC470735 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	405
0.1-0.2	1464
0.2-0.3	3038
0.3-0.4	6524
0.4-0.5	9701
0.5-0.6	7563
0.6-0.7	7230
0.7-0.8	6160
0.8-0.85	530
0.85-0.9	55
0.9-0.95	24
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329647
0.9503	High Similarity	NPC470580
0.9448	High Similarity	NPC19056
0.9448	High Similarity	NPC470583
0.9444	High Similarity	NPC270027
0.9333	High Similarity	NPC266513
0.9333	High Similarity	NPC115447
0.9333	High Similarity	NPC470582
0.9333	High Similarity	NPC470581
0.9277	High Similarity	NPC283980
0.9277	High Similarity	NPC187441
0.9217	High Similarity	NPC83331
0.9207	High Similarity	NPC294501
0.9146	High Similarity	NPC478021
0.9136	High Similarity	NPC478020
0.9136	High Similarity	NPC478022
0.8917	High Similarity	NPC280753
0.8917	High Similarity	NPC44378
0.8882	High Similarity	NPC208651
0.8882	High Similarity	NPC206641
0.8862	High Similarity	NPC183441
0.8855	High Similarity	NPC175477
0.8805	High Similarity	NPC205918
0.8793	High Similarity	NPC314672
0.8788	High Similarity	NPC478026
0.8772	High Similarity	NPC315221
0.8765	High Similarity	NPC29552
0.8758	High Similarity	NPC3449
0.8734	High Similarity	NPC94781
0.8721	High Similarity	NPC313452
0.8713	High Similarity	NPC72783
0.8712	High Similarity	NPC53139
0.8706	High Similarity	NPC176246
0.8704	High Similarity	NPC478027
0.8704	High Similarity	NPC148323
0.8704	High Similarity	NPC283480
0.8683	High Similarity	NPC63470
0.8679	High Similarity	NPC120171
0.8667	High Similarity	NPC187934
0.8667	High Similarity	NPC97637
0.8652	High Similarity	NPC108487
0.8647	High Similarity	NPC70862
0.8642	High Similarity	NPC192219
0.8642	High Similarity	NPC82190
0.8642	High Similarity	NPC314257
0.8642	High Similarity	NPC174599
0.8631	High Similarity	NPC246274
0.8631	High Similarity	NPC222455
0.8608	High Similarity	NPC136878
0.8606	High Similarity	NPC317544
0.8596	High Similarity	NPC475246
0.8588	High Similarity	NPC65118
0.8588	High Similarity	NPC199357
0.858	High Similarity	NPC209393
0.858	High Similarity	NPC312482
0.858	High Similarity	NPC205172
0.8563	High Similarity	NPC472049
0.8556	High Similarity	NPC131405
0.8554	High Similarity	NPC146837
0.8554	High Similarity	NPC212099
0.8554	High Similarity	NPC101116
0.8554	High Similarity	NPC278329
0.8547	High Similarity	NPC133775
0.8538	High Similarity	NPC470667
0.8538	High Similarity	NPC186800
0.8538	High Similarity	NPC3718
0.8537	High Similarity	NPC472889
0.8529	High Similarity	NPC111536
0.8529	High Similarity	NPC76128
0.8529	High Similarity	NPC315619
0.8529	High Similarity	NPC30432
0.8529	High Similarity	NPC5029
0.8529	High Similarity	NPC271385
0.8523	High Similarity	NPC205721
0.8521	High Similarity	NPC328321
0.8509	High Similarity	NPC475407
0.85	High Similarity	NPC112816
0.8497	Intermediate Similarity	NPC114257
0.8497	Intermediate Similarity	NPC299149
0.8497	Intermediate Similarity	NPC153578
0.8497	Intermediate Similarity	NPC277710
0.8494	Intermediate Similarity	NPC477627
0.8491	Intermediate Similarity	NPC285122
0.8488	Intermediate Similarity	NPC475233
0.8488	Intermediate Similarity	NPC46958
0.8488	Intermediate Similarity	NPC102053
0.8485	Intermediate Similarity	NPC314795
0.8481	Intermediate Similarity	NPC103910
0.8481	Intermediate Similarity	NPC29932
0.848	Intermediate Similarity	NPC154986
0.848	Intermediate Similarity	NPC85368
0.848	Intermediate Similarity	NPC203751
0.8452	Intermediate Similarity	NPC178281
0.8448	Intermediate Similarity	NPC477860
0.8448	Intermediate Similarity	NPC475161
0.8439	Intermediate Similarity	NPC47191
0.843	Intermediate Similarity	NPC68381
0.843	Intermediate Similarity	NPC223735
0.843	Intermediate Similarity	NPC307754
0.8427	Intermediate Similarity	NPC48474
0.8424	Intermediate Similarity	NPC478226
0.8424	Intermediate Similarity	NPC177742
0.8421	Intermediate Similarity	NPC473113
0.8415	Intermediate Similarity	NPC478133
0.8412	Intermediate Similarity	NPC137460
0.8412	Intermediate Similarity	NPC473096
0.8412	Intermediate Similarity	NPC473095
0.8405	Intermediate Similarity	NPC478220
0.8402	Intermediate Similarity	NPC469419
0.8402	Intermediate Similarity	NPC472150
0.8391	Intermediate Similarity	NPC212290
0.8391	Intermediate Similarity	NPC58538
0.8385	Intermediate Similarity	NPC470479
0.8383	Intermediate Similarity	NPC316457
0.8383	Intermediate Similarity	NPC471493
0.8382	Intermediate Similarity	NPC314489
0.8382	Intermediate Similarity	NPC232818
0.8382	Intermediate Similarity	NPC289876
0.8382	Intermediate Similarity	NPC198893
0.8375	Intermediate Similarity	NPC470330
0.8372	Intermediate Similarity	NPC470335
0.8372	Intermediate Similarity	NPC470336
0.8372	Intermediate Similarity	NPC472054
0.8372	Intermediate Similarity	NPC98776
0.8362	Intermediate Similarity	NPC105591
0.8354	Intermediate Similarity	NPC474622
0.8354	Intermediate Similarity	NPC155686
0.8354	Intermediate Similarity	NPC474621
0.8354	Intermediate Similarity	NPC137301
0.8353	Intermediate Similarity	NPC103633
0.8353	Intermediate Similarity	NPC473094
0.8343	Intermediate Similarity	NPC261012
0.8343	Intermediate Similarity	NPC109403
0.8343	Intermediate Similarity	NPC314738
0.8333	Intermediate Similarity	NPC477683
0.8333	Intermediate Similarity	NPC56735
0.8333	Intermediate Similarity	NPC216752
0.8333	Intermediate Similarity	NPC61594
0.8333	Intermediate Similarity	NPC470334
0.8333	Intermediate Similarity	NPC478219
0.8333	Intermediate Similarity	NPC168584
0.8333	Intermediate Similarity	NPC477682
0.8324	Intermediate Similarity	NPC108202
0.8324	Intermediate Similarity	NPC171706
0.8324	Intermediate Similarity	NPC294629
0.8324	Intermediate Similarity	NPC146803
0.8323	Intermediate Similarity	NPC284495
0.8313	Intermediate Similarity	NPC474630
0.8313	Intermediate Similarity	NPC257309
0.8313	Intermediate Similarity	NPC170055
0.8305	Intermediate Similarity	NPC87583
0.8304	Intermediate Similarity	NPC270578
0.8304	Intermediate Similarity	NPC259905
0.8304	Intermediate Similarity	NPC52382
0.8303	Intermediate Similarity	NPC317585
0.8303	Intermediate Similarity	NPC478221
0.8303	Intermediate Similarity	NPC170189
0.8303	Intermediate Similarity	NPC472890
0.8303	Intermediate Similarity	NPC478230
0.8303	Intermediate Similarity	NPC69043
0.8303	Intermediate Similarity	NPC208173
0.8303	Intermediate Similarity	NPC474501
0.8302	Intermediate Similarity	NPC143898
0.8295	Intermediate Similarity	NPC478001
0.8294	Intermediate Similarity	NPC178851
0.8293	Intermediate Similarity	NPC478224
0.8293	Intermediate Similarity	NPC115249
0.8291	Intermediate Similarity	NPC257003
0.8286	Intermediate Similarity	NPC244903
0.8284	Intermediate Similarity	NPC183672
0.8284	Intermediate Similarity	NPC278419
0.8284	Intermediate Similarity	NPC147596
0.8284	Intermediate Similarity	NPC179198
0.8284	Intermediate Similarity	NPC66087
0.828	Intermediate Similarity	NPC103337
0.828	Intermediate Similarity	NPC114620
0.8276	Intermediate Similarity	NPC65563
0.8276	Intermediate Similarity	NPC470949
0.8276	Intermediate Similarity	NPC472380
0.8276	Intermediate Similarity	NPC472382
0.8276	Intermediate Similarity	NPC472384
0.8274	Intermediate Similarity	NPC478134
0.8274	Intermediate Similarity	NPC476929
0.8266	Intermediate Similarity	NPC45522
0.8266	Intermediate Similarity	NPC169977
0.8266	Intermediate Similarity	NPC470438
0.8266	Intermediate Similarity	NPC42773
0.8266	Intermediate Similarity	NPC213052
0.8266	Intermediate Similarity	NPC24043
0.8266	Intermediate Similarity	NPC469393
0.8266	Intermediate Similarity	NPC101026
0.8266	Intermediate Similarity	NPC21666
0.8263	Intermediate Similarity	NPC231475
0.8263	Intermediate Similarity	NPC472156
0.8263	Intermediate Similarity	NPC57072
0.8256	Intermediate Similarity	NPC206123
0.8256	Intermediate Similarity	NPC105511
0.8256	Intermediate Similarity	NPC475058
0.8256	Intermediate Similarity	NPC44558
0.8256	Intermediate Similarity	NPC95866

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 NPC470735 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	895
0.2-0.3	1742
0.3-0.4	2797
0.4-0.5	1993
0.5-0.6	985
0.6-0.7	278
0.7-0.8	82
0.8-0.85	29
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8786	High Similarity	NPD7879	Clinical (unspecified phase)
0.8475	Intermediate Similarity	NPD6534	Approved
0.8475	Intermediate Similarity	NPD6535	Approved
0.8343	Intermediate Similarity	NPD6780	Approved
0.8343	Intermediate Similarity	NPD6777	Approved
0.8343	Intermediate Similarity	NPD6779	Approved
0.8343	Intermediate Similarity	NPD6782	Approved
0.8343	Intermediate Similarity	NPD6778	Approved
0.8343	Intermediate Similarity	NPD6776	Approved
0.8343	Intermediate Similarity	NPD8150	Discontinued
0.8343	Intermediate Similarity	NPD6781	Approved
0.8333	Intermediate Similarity	NPD7699	Phase 2
0.8333	Intermediate Similarity	NPD7700	Phase 2
0.8306	Intermediate Similarity	NPD7435	Discontinued
0.8246	Intermediate Similarity	NPD3751	Discontinued
0.8208	Intermediate Similarity	NPD6797	Phase 2
0.8198	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD8320	Phase 1
0.8162	Intermediate Similarity	NPD8319	Approved
0.8161	Intermediate Similarity	NPD7251	Discontinued
0.8114	Intermediate Similarity	NPD7808	Phase 3
0.8114	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7696	Phase 3
0.8108	Intermediate Similarity	NPD7698	Approved
0.8108	Intermediate Similarity	NPD7697	Approved
0.8095	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7870	Phase 2
0.8065	Intermediate Similarity	NPD7871	Phase 2
0.8046	Intermediate Similarity	NPD7074	Phase 3
0.8042	Intermediate Similarity	NPD7874	Approved
0.8042	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8032	Intermediate Similarity	NPD7701	Phase 2
0.7989	Intermediate Similarity	NPD7054	Approved
0.7966	Intermediate Similarity	NPD8313	Approved
0.7966	Intermediate Similarity	NPD8312	Approved
0.7944	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7472	Approved
0.7931	Intermediate Similarity	NPD3818	Discontinued
0.7912	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD6213	Phase 3
0.7912	Intermediate Similarity	NPD6212	Phase 3
0.7907	Intermediate Similarity	NPD3787	Discontinued
0.7906	Intermediate Similarity	NPD7801	Approved
0.7844	Intermediate Similarity	NPD4380	Phase 2
0.7831	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6166	Phase 2
0.7816	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6190	Approved
0.7778	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7075	Discontinued
0.7766	Intermediate Similarity	NPD6823	Phase 2
0.7753	Intermediate Similarity	NPD6559	Discontinued
0.7661	Intermediate Similarity	NPD5402	Approved
0.7638	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8434	Phase 2
0.7636	Intermediate Similarity	NPD3300	Phase 2
0.7617	Intermediate Similarity	NPD8151	Discontinued
0.7602	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6232	Discontinued
0.7571	Intermediate Similarity	NPD7473	Discontinued
0.7544	Intermediate Similarity	NPD6801	Discontinued
0.7544	Intermediate Similarity	NPD1934	Approved
0.7543	Intermediate Similarity	NPD6959	Discontinued
0.7514	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD7819	Suspended
0.7486	Intermediate Similarity	NPD5844	Phase 1
0.7459	Intermediate Similarity	NPD8368	Discontinued
0.7457	Intermediate Similarity	NPD3817	Phase 2
0.7439	Intermediate Similarity	NPD7266	Discontinued
0.743	Intermediate Similarity	NPD7799	Discontinued
0.743	Intermediate Similarity	NPD7228	Approved
0.7423	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD2801	Approved
0.7389	Intermediate Similarity	NPD1470	Approved
0.7386	Intermediate Similarity	NPD5494	Approved
0.7381	Intermediate Similarity	NPD7390	Discontinued
0.7368	Intermediate Similarity	NPD3226	Approved
0.7363	Intermediate Similarity	NPD7685	Pre-registration
0.736	Intermediate Similarity	NPD7783	Phase 2
0.736	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5403	Approved
0.7337	Intermediate Similarity	NPD8407	Phase 2
0.7337	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6599	Discontinued
0.7322	Intermediate Similarity	NPD4954	Approved
0.7322	Intermediate Similarity	NPD5028	Approved
0.7322	Intermediate Similarity	NPD5034	Approved
0.7322	Intermediate Similarity	NPD4955	Approved
0.7322	Intermediate Similarity	NPD36	Approved
0.7322	Intermediate Similarity	NPD5026	Approved
0.7317	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6799	Approved
0.7268	Intermediate Similarity	NPD5030	Phase 2
0.7258	Intermediate Similarity	NPD5038	Approved
0.7258	Intermediate Similarity	NPD5037	Approved
0.7257	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD37	Approved
0.7235	Intermediate Similarity	NPD5401	Approved
0.7235	Intermediate Similarity	NPD2532	Approved
0.7235	Intermediate Similarity	NPD2534	Approved
0.7235	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2533	Approved
0.7232	Intermediate Similarity	NPD6234	Discontinued
0.7216	Intermediate Similarity	NPD4966	Approved
0.7216	Intermediate Similarity	NPD4967	Phase 2
0.7216	Intermediate Similarity	NPD4965	Approved
0.7204	Intermediate Similarity	NPD5036	Approved
0.7202	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8059	Phase 3
0.7198	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1512	Approved
0.7186	Intermediate Similarity	NPD1549	Phase 2
0.7184	Intermediate Similarity	NPD7411	Suspended
0.7181	Intermediate Similarity	NPD8361	Approved
0.7181	Intermediate Similarity	NPD8435	Approved
0.7181	Intermediate Similarity	NPD8360	Approved
0.7178	Intermediate Similarity	NPD943	Approved
0.7178	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7458	Discontinued
0.7136	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1201	Approved
0.7127	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.7126	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1510	Phase 2
0.7102	Intermediate Similarity	NPD8455	Phase 2
0.7102	Intermediate Similarity	NPD1465	Phase 2
0.7101	Intermediate Similarity	NPD4628	Phase 3
0.7101	Intermediate Similarity	NPD8166	Discontinued
0.7097	Intermediate Similarity	NPD5035	Approved
0.7083	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7240	Approved
0.7079	Intermediate Similarity	NPD3749	Approved
0.7076	Intermediate Similarity	NPD1511	Approved
0.7072	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5406	Approved
0.7066	Intermediate Similarity	NPD5404	Approved
0.7066	Intermediate Similarity	NPD2935	Discontinued
0.7066	Intermediate Similarity	NPD5405	Approved
0.7066	Intermediate Similarity	NPD5408	Approved
0.703	Intermediate Similarity	NPD230	Phase 1
0.7018	Intermediate Similarity	NPD7236	Approved
0.7	Intermediate Similarity	NPD3750	Approved
0.6989	Remote Similarity	NPD5031	Approved
0.6989	Remote Similarity	NPD5027	Approved
0.6989	Remote Similarity	NPD5029	Approved
0.6988	Remote Similarity	NPD1607	Approved
0.6985	Remote Similarity	NPD7584	Approved
0.697	Remote Similarity	NPD1240	Approved
0.6968	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2796	Approved
0.6961	Remote Similarity	NPD7199	Phase 2
0.6959	Remote Similarity	NPD8485	Approved
0.6954	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3764	Approved
0.6944	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1653	Approved
0.6914	Remote Similarity	NPD7239	Suspended
0.6895	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3926	Phase 2
0.6879	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7907	Approved
0.6868	Remote Similarity	NPD1247	Approved
0.6845	Remote Similarity	NPD8404	Phase 2
0.6842	Remote Similarity	NPD6674	Discontinued
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7768	Phase 2
0.6831	Remote Similarity	NPD5710	Approved
0.6831	Remote Similarity	NPD5711	Approved
0.6829	Remote Similarity	NPD7930	Approved
0.6824	Remote Similarity	NPD1471	Phase 3
0.681	Remote Similarity	NPD2798	Approved
0.6805	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4665	Approved
0.6779	Remote Similarity	NPD4111	Phase 1
0.6772	Remote Similarity	NPD5032	Approved
0.6768	Remote Similarity	NPD4914	Approved
0.6765	Remote Similarity	NPD6100	Approved
0.6765	Remote Similarity	NPD6099	Approved
0.6758	Remote Similarity	NPD919	Approved
0.6744	Remote Similarity	NPD2800	Approved
0.6743	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7028	Phase 2
0.6736	Remote Similarity	NPD6836	Approved
0.6725	Remote Similarity	NPD2344	Approved
0.6717	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD8285	Discontinued
0.6706	Remote Similarity	NPD3748	Approved
0.6706	Remote Similarity	NPD2799	Discontinued

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