NPASS Compound

Structure

NPC204469 OpenBabel07101719252D 37 40 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 16 20 1 0 0 0 0 16 25 2 0 0 0 0 17 26 1 0 0 0 0 17 28 2 0 0 0 0 18 15 1 1 0 0 0 18 22 1 0 0 0 0 19 27 1 0 0 0 0 19 30 2 0 0 0 0 20 31 1 0 0 0 0 21 23 2 0 0 0 0 21 37 1 0 0 0 0 22 24 2 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 24 26 1 0 0 0 0 24 30 1 0 0 0 0 25 32 1 0 0 0 0 26 33 2 0 0 0 0 27 34 2 0 0 0 0 28 29 1 0 0 0 0 28 35 1 0 0 0 0 29 36 2 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.2
Volume:	523.104
LogP:	6.669
LogD:	2.589
LogS:	-2.773
# Rotatable Bonds:	4
TPSA:	128.2
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.128
Synthetic Accessibility Score:	3.762
Fsp3:	0.267
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.122
MDCK Permeability:	1.0847932571778074e-05
Pgp-inhibitor:	0.824
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.859
20% Bioavailability (F20%):	0.259
30% Bioavailability (F30%):	0.224

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	86.47430419921875%
Volume Distribution (VD):	0.645
Pgp-substrate:	16.020652770996094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.486
CYP1A2-substrate:	0.259
CYP2C19-inhibitor:	0.561
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.191
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.051

ADMET: Excretion

Clearance (CL):	0.79
Half-life (T1/2):	0.311

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.532
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.477
Rat Oral Acute Toxicity:	0.384
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.941
Carcinogencity:	0.168
Eye Corrosion:	0.003
Eye Irritation:	0.891
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC204469

Natural Product ID:	NPC204469
*Common Name:**	Artonin O
IUPAC Name:	n.a.
Synonyms:	Artonin O
Standard InCHIKey:	RREWBAHJGHVXMY-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C30H30O7/c1-13(2)7-9-16-20(31)12-21-23(25(16)32)27(34)19-11-18(15(5)6)22-24(30(19)37-21)26(33)17(10-8-14(3)4)28(35)29(22)36/h7-8,12,18,31-32,35H,5,9-11H2,1-4,6H3/t18-/m1/s1
SMILES:	CC(=CCc1c(cc2c(c1O)c(=O)c1C[C@H](C(=C)C)C3=C(C(=O)C(=C(C3=O)O)CC=C(C)C)c1o2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096733
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384315]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	Stems	n.a.	n.a.	PMID[29227656]

☑ 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
ED50	1
IC50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[505359]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	3.2	nM	PMID[505359]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[505359]

☑ 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 NPC204469 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	416
0.1-0.2	1653
0.2-0.3	4378
0.3-0.4	10964
0.4-0.5	7637
0.5-0.6	4612
0.6-0.7	5837
0.7-0.8	4306
0.8-0.85	1928
0.85-0.9	879
0.9-0.95	86
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC329678
0.9433	High Similarity	NPC326500
0.9429	High Similarity	NPC200694
0.942	High Similarity	NPC470669
0.942	High Similarity	NPC470668
0.9416	High Similarity	NPC174999
0.9362	High Similarity	NPC212932
0.9362	High Similarity	NPC158874
0.9362	High Similarity	NPC293053
0.9362	High Similarity	NPC9117
0.9362	High Similarity	NPC24821
0.9362	High Similarity	NPC190637
0.9357	High Similarity	NPC282300
0.9353	High Similarity	NPC301217
0.9353	High Similarity	NPC96565
0.9353	High Similarity	NPC220062
0.9353	High Similarity	NPC303633
0.9353	High Similarity	NPC216978
0.9353	High Similarity	NPC55018
0.9338	High Similarity	NPC93756
0.9338	High Similarity	NPC108113
0.9301	High Similarity	NPC14001
0.9301	High Similarity	NPC166757
0.9296	High Similarity	NPC273538
0.9296	High Similarity	NPC216538
0.9291	High Similarity	NPC62840
0.9291	High Similarity	NPC473042
0.9291	High Similarity	NPC214236
0.9291	High Similarity	NPC217083
0.9291	High Similarity	NPC78803
0.9291	High Similarity	NPC59739
0.9291	High Similarity	NPC299080
0.9291	High Similarity	NPC293852
0.9286	High Similarity	NPC159275
0.9286	High Similarity	NPC241100
0.9286	High Similarity	NPC261227
0.9286	High Similarity	NPC172986
0.9286	High Similarity	NPC270883
0.9281	High Similarity	NPC470671
0.9281	High Similarity	NPC470672
0.9281	High Similarity	NPC201395
0.9281	High Similarity	NPC131130
0.9281	High Similarity	NPC474487
0.9281	High Similarity	NPC474504
0.9275	High Similarity	NPC156910
0.927	High Similarity	NPC125920
0.9265	High Similarity	NPC10971
0.9236	High Similarity	NPC296869
0.9236	High Similarity	NPC244407
0.9236	High Similarity	NPC470460
0.9231	High Similarity	NPC178343
0.9231	High Similarity	NPC474161
0.9231	High Similarity	NPC220418
0.9231	High Similarity	NPC470458
0.9231	High Similarity	NPC5820
0.9231	High Similarity	NPC124729
0.9231	High Similarity	NPC306488
0.9231	High Similarity	NPC476088
0.9225	High Similarity	NPC473812
0.9225	High Similarity	NPC38219
0.9225	High Similarity	NPC473813
0.9225	High Similarity	NPC219915
0.922	High Similarity	NPC205006
0.922	High Similarity	NPC110969
0.922	High Similarity	NPC14871
0.922	High Similarity	NPC147688
0.922	High Similarity	NPC156590
0.922	High Similarity	NPC64908
0.922	High Similarity	NPC118840
0.9214	High Similarity	NPC139554
0.9214	High Similarity	NPC78913
0.9214	High Similarity	NPC217186
0.9214	High Similarity	NPC18260
0.9214	High Similarity	NPC23257
0.9214	High Similarity	NPC53181
0.9203	High Similarity	NPC60667
0.9178	High Similarity	NPC81474
0.9172	High Similarity	NPC470461
0.9161	High Similarity	NPC472447
0.9161	High Similarity	NPC472446
0.9161	High Similarity	NPC319752
0.9155	High Similarity	NPC11561
0.9155	High Similarity	NPC226636
0.9149	High Similarity	NPC150522
0.9149	High Similarity	NPC305355
0.9149	High Similarity	NPC235239
0.9149	High Similarity	NPC471587
0.9149	High Similarity	NPC477272
0.9149	High Similarity	NPC69769
0.9149	High Similarity	NPC475680
0.9137	High Similarity	NPC13408
0.913	High Similarity	NPC144027
0.913	High Similarity	NPC236974
0.9124	High Similarity	NPC25937
0.9118	High Similarity	NPC270369
0.9118	High Similarity	NPC5515
0.9097	High Similarity	NPC246948
0.9097	High Similarity	NPC475052
0.9097	High Similarity	NPC142405
0.9097	High Similarity	NPC176229
0.9097	High Similarity	NPC195621
0.9097	High Similarity	NPC154217
0.9097	High Similarity	NPC20488
0.9097	High Similarity	NPC88964
0.9097	High Similarity	NPC301276
0.9097	High Similarity	NPC214774
0.9097	High Similarity	NPC54577
0.9097	High Similarity	NPC111786
0.9097	High Similarity	NPC83357
0.9097	High Similarity	NPC312973
0.9097	High Similarity	NPC470647
0.9097	High Similarity	NPC267375
0.9097	High Similarity	NPC67805
0.9091	High Similarity	NPC223812
0.9091	High Similarity	NPC87609
0.9091	High Similarity	NPC94794
0.9091	High Similarity	NPC11700
0.9091	High Similarity	NPC81697
0.9091	High Similarity	NPC77794
0.9091	High Similarity	NPC85162
0.9091	High Similarity	NPC107177
0.9091	High Similarity	NPC112791
0.9091	High Similarity	NPC196459
0.9091	High Similarity	NPC278249
0.9091	High Similarity	NPC125894
0.9091	High Similarity	NPC470296
0.9091	High Similarity	NPC188632
0.9085	High Similarity	NPC90582
0.9085	High Similarity	NPC156190
0.9085	High Similarity	NPC262094
0.9085	High Similarity	NPC17170
0.9085	High Similarity	NPC103362
0.9085	High Similarity	NPC279650
0.9085	High Similarity	NPC166689
0.9085	High Similarity	NPC96408
0.9085	High Similarity	NPC258630
0.9078	High Similarity	NPC143799
0.9078	High Similarity	NPC152042
0.9078	High Similarity	NPC241838
0.9071	High Similarity	NPC474624
0.9071	High Similarity	NPC138047
0.9071	High Similarity	NPC131782
0.9065	High Similarity	NPC101752
0.9065	High Similarity	NPC151113
0.9051	High Similarity	NPC31872
0.9051	High Similarity	NPC473584
0.9051	High Similarity	NPC475589
0.9041	High Similarity	NPC269420
0.9034	High Similarity	NPC283234
0.9034	High Similarity	NPC296998
0.9034	High Similarity	NPC23728
0.9034	High Similarity	NPC237635
0.9034	High Similarity	NPC104406
0.9034	High Similarity	NPC24673
0.9034	High Similarity	NPC79469
0.9034	High Similarity	NPC473077
0.9034	High Similarity	NPC201731
0.9034	High Similarity	NPC110303
0.9034	High Similarity	NPC249942
0.9034	High Similarity	NPC297886
0.9034	High Similarity	NPC97716
0.9028	High Similarity	NPC311741
0.9028	High Similarity	NPC278175
0.9028	High Similarity	NPC224714
0.9028	High Similarity	NPC131568
0.9028	High Similarity	NPC178627
0.9028	High Similarity	NPC257236
0.9028	High Similarity	NPC473015
0.9028	High Similarity	NPC271288
0.9028	High Similarity	NPC473014
0.9028	High Similarity	NPC131579
0.9028	High Similarity	NPC1886
0.9028	High Similarity	NPC473013
0.9028	High Similarity	NPC234629
0.9028	High Similarity	NPC196137
0.9028	High Similarity	NPC235217
0.9028	High Similarity	NPC469935
0.9021	High Similarity	NPC324436
0.9021	High Similarity	NPC32739
0.9021	High Similarity	NPC36181
0.9021	High Similarity	NPC194432
0.9021	High Similarity	NPC223500
0.9021	High Similarity	NPC125855
0.9021	High Similarity	NPC144499
0.9021	High Similarity	NPC296917
0.9021	High Similarity	NPC148757
0.9021	High Similarity	NPC66515
0.9021	High Similarity	NPC328164
0.9021	High Similarity	NPC182852
0.9021	High Similarity	NPC228504
0.9021	High Similarity	NPC325346
0.9021	High Similarity	NPC306829
0.9021	High Similarity	NPC40833
0.9021	High Similarity	NPC64915
0.9021	High Similarity	NPC10937
0.9021	High Similarity	NPC166934
0.9021	High Similarity	NPC265040
0.9021	High Similarity	NPC166482
0.9021	High Similarity	NPC76338
0.9021	High Similarity	NPC324134

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 NPC204469 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	980
0.2-0.3	1680
0.3-0.4	2743
0.4-0.5	1912
0.5-0.6	1016
0.6-0.7	305
0.7-0.8	101
0.8-0.85	31
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9296	High Similarity	NPD4378	Clinical (unspecified phase)
0.9028	High Similarity	NPD7410	Clinical (unspecified phase)
0.8671	High Similarity	NPD1550	Clinical (unspecified phase)
0.8671	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD8443	Clinical (unspecified phase)
0.8611	High Similarity	NPD1549	Phase 2
0.8552	High Similarity	NPD2800	Approved
0.8543	High Similarity	NPD7411	Suspended
0.8531	High Similarity	NPD1510	Phase 2
0.8521	High Similarity	NPD6651	Approved
0.8511	High Similarity	NPD1240	Approved
0.8506	High Similarity	NPD7075	Discontinued
0.8487	Intermediate Similarity	NPD6801	Discontinued
0.8477	Intermediate Similarity	NPD4380	Phase 2
0.8472	Intermediate Similarity	NPD2796	Approved
0.8456	Intermediate Similarity	NPD1512	Approved
0.8431	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1607	Approved
0.8367	Intermediate Similarity	NPD3750	Approved
0.8356	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1511	Approved
0.8322	Intermediate Similarity	NPD6799	Approved
0.8261	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2801	Approved
0.8194	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD1243	Approved
0.8153	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1934	Approved
0.8117	Intermediate Similarity	NPD6599	Discontinued
0.8113	Intermediate Similarity	NPD6959	Discontinued
0.8089	Intermediate Similarity	NPD3882	Suspended
0.8089	Intermediate Similarity	NPD7768	Phase 2
0.8075	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6166	Phase 2
0.8054	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD5403	Approved
0.8027	Intermediate Similarity	NPD3748	Approved
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.7925	Intermediate Similarity	NPD3749	Approved
0.7908	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD2534	Approved
0.7908	Intermediate Similarity	NPD5401	Approved
0.7908	Intermediate Similarity	NPD2533	Approved
0.7905	Intermediate Similarity	NPD2799	Discontinued
0.7881	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6100	Approved
0.7852	Intermediate Similarity	NPD6099	Approved
0.7844	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD5494	Approved
0.7806	Intermediate Similarity	NPD920	Approved
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3268	Approved
0.774	Intermediate Similarity	NPD2313	Discontinued
0.774	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7808	Phase 3
0.7733	Intermediate Similarity	NPD1551	Phase 2
0.7733	Intermediate Similarity	NPD2935	Discontinued
0.773	Intermediate Similarity	NPD422	Phase 1
0.7711	Intermediate Similarity	NPD7054	Approved
0.7703	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD5124	Phase 1
0.7697	Intermediate Similarity	NPD7473	Discontinued
0.7688	Intermediate Similarity	NPD5402	Approved
0.7682	Intermediate Similarity	NPD2344	Approved
0.7677	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD9717	Approved
0.7667	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7074	Phase 3
0.7665	Intermediate Similarity	NPD7472	Approved
0.7654	Intermediate Similarity	NPD919	Approved
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD2797	Approved
0.7639	Intermediate Similarity	NPD1203	Approved
0.7633	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6232	Discontinued
0.7619	Intermediate Similarity	NPD5953	Discontinued
0.7613	Intermediate Similarity	NPD7390	Discontinued
0.7605	Intermediate Similarity	NPD7286	Phase 2
0.7603	Intermediate Similarity	NPD4908	Phase 1
0.7586	Intermediate Similarity	NPD2798	Approved
0.7582	Intermediate Similarity	NPD2654	Approved
0.7561	Intermediate Similarity	NPD1247	Approved
0.7514	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD4363	Phase 3
0.75	Intermediate Similarity	NPD4360	Phase 2
0.7484	Intermediate Similarity	NPD3226	Approved
0.7484	Intermediate Similarity	NPD2309	Approved
0.7471	Intermediate Similarity	NPD6559	Discontinued
0.7448	Intermediate Similarity	NPD3225	Approved
0.7447	Intermediate Similarity	NPD1548	Phase 1
0.7434	Intermediate Similarity	NPD7033	Discontinued
0.7425	Intermediate Similarity	NPD2403	Approved
0.7412	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD943	Approved
0.7397	Intermediate Similarity	NPD3266	Approved
0.7397	Intermediate Similarity	NPD3267	Approved
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7383	Intermediate Similarity	NPD1296	Phase 2
0.7365	Intermediate Similarity	NPD6832	Phase 2
0.7365	Intermediate Similarity	NPD3926	Phase 2
0.7362	Intermediate Similarity	NPD4288	Approved
0.7361	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1610	Phase 2
0.736	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4361	Phase 2
0.7338	Intermediate Similarity	NPD2346	Discontinued
0.732	Intermediate Similarity	NPD4308	Phase 3
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7305	Intermediate Similarity	NPD5710	Approved
0.7305	Intermediate Similarity	NPD5711	Approved
0.7301	Intermediate Similarity	NPD1465	Phase 2
0.7284	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1729	Discontinued
0.7214	Intermediate Similarity	NPD1241	Discontinued
0.7208	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9545	Approved
0.72	Intermediate Similarity	NPD4625	Phase 3
0.7192	Intermediate Similarity	NPD1608	Approved
0.7183	Intermediate Similarity	NPD9493	Approved
0.716	Intermediate Similarity	NPD7458	Discontinued
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD411	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD230	Phase 1
0.7124	Intermediate Similarity	NPD447	Suspended
0.7118	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6585	Discontinued
0.7115	Intermediate Similarity	NPD1471	Phase 3
0.7095	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7003	Approved
0.7081	Intermediate Similarity	NPD5049	Phase 3
0.7075	Intermediate Similarity	NPD3972	Approved
0.7073	Intermediate Similarity	NPD5890	Approved
0.7073	Intermediate Similarity	NPD5889	Approved
0.7069	Intermediate Similarity	NPD6104	Discontinued
0.7067	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4307	Phase 2
0.7055	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5406	Approved
0.7051	Intermediate Similarity	NPD5404	Approved
0.7051	Intermediate Similarity	NPD5408	Approved
0.7051	Intermediate Similarity	NPD5405	Approved
0.7044	Intermediate Similarity	NPD2354	Approved
0.7037	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3751	Discontinued
0.702	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1933	Approved
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD1201	Approved
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD1019	Discontinued
0.7	Intermediate Similarity	NPD3300	Phase 2
0.6986	Remote Similarity	NPD17	Approved
0.6983	Remote Similarity	NPD4287	Approved
0.6977	Remote Similarity	NPD3446	Phase 1
0.6968	Remote Similarity	NPD7584	Approved
0.6966	Remote Similarity	NPD8434	Phase 2
0.6966	Remote Similarity	NPD8150	Discontinued
0.6959	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4060	Phase 1
0.6946	Remote Similarity	NPD2296	Approved
0.6936	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1164	Approved
0.6933	Remote Similarity	NPD1470	Approved
0.6928	Remote Similarity	NPD3764	Approved
0.6919	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1652	Phase 2
0.6903	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3787	Discontinued
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD2353	Approved
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6002	Phase 3
0.6893	Remote Similarity	NPD8312	Approved
0.6893	Remote Similarity	NPD8313	Approved
0.6889	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6233	Phase 2
0.6867	Remote Similarity	NPD8651	Approved
0.6855	Remote Similarity	NPD2424	Discontinued
0.6852	Remote Similarity	NPD7212	Phase 2
0.6852	Remote Similarity	NPD7213	Phase 3
0.6852	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1481	Phase 2

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