NPASS Compound

Structure

NPC476345 OpenBabel07101718312D 30 32 0 0 1 0 0 0 0 0999 V2000 -3.2579 1.4565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2193 -0.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6646 0.5430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0768 -0.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1977 -3.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1488 -4.1835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0823 -0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0388 -2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7330 -2.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9898 -2.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8920 -3.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6840 -2.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4128 0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8430 -3.8234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -1.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4272 -1.8671 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 -0.9706 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 4 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 5 1 0 0 0 0 5 10 1 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 9 2 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 29 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 15 30 1 0 0 0 0 18 11 1 6 0 0 0 18 19 1 0 0 0 0 19 12 1 1 0 0 0 19 24 1 0 0 0 0 20 22 2 0 0 0 0 20 25 1 0 0 0 0 21 23 2 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 1 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	434.913
LogP:	4.372
LogD:	3.832
LogS:	-4.821
# Rotatable Bonds:	10
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.562
Synthetic Accessibility Score:	3.541
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.756
MDCK Permeability:	2.5056948288693093e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.547
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.252
30% Bioavailability (F30%):	0.092

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	98.7935562133789%
Volume Distribution (VD):	0.586
Pgp-substrate:	1.4394140243530273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.113
CYP1A2-substrate:	0.876
CYP2C19-inhibitor:	0.679
CYP2C19-substrate:	0.696
CYP2C9-inhibitor:	0.681
CYP2C9-substrate:	0.767
CYP2D6-inhibitor:	0.816
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.613
CYP3A4-substrate:	0.794

ADMET: Excretion

Clearance (CL):	11.429
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.523
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.811
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.105
Maximum Recommended Daily Dose:	0.436
Skin Sensitization:	0.949
Carcinogencity:	0.13
Eye Corrosion:	0.005
Eye Irritation:	0.926
Respiratory Toxicity:	0.685

Download Data

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

Natural Product: NPC476345

Natural Product ID:	NPC476345
*Common Name:**	4,4'-Dihydroxy-3,3'-Dimethoxy-9-Butoxy-9,9'-Epoxylignan
IUPAC Name:	4-[[(3R,4R,5S)-5-butoxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	OMCHYMLRSCWZQB-GLDPYIMESA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-4-5-10-29-24-19(12-17-7-9-21(26)23(14-17)28-3)18(15-30-24)11-16-6-8-20(25)22(13-16)27-2/h6-9,13-14,18-19,24-26H,4-5,10-12,15H2,1-3H3/t18-,19+,24-/m0/s1
SMILES:	CCCCOC1C(C(CO1)CC2=CC(=C(C=C2)O)OC)CC3=CC(=C(C=C3)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573411
PubChem CID:	25156705
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans

*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
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	146000.0	nM	PMID[567407]

☑ 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 NPC476345 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	343
0.1-0.2	1398
0.2-0.3	3570
0.3-0.4	10664
0.4-0.5	8390
0.5-0.6	6130
0.6-0.7	8572
0.7-0.8	2741
0.8-0.85	624
0.85-0.9	204
0.9-0.95	50
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC275950
0.976	High Similarity	NPC181079
0.976	High Similarity	NPC173308
0.9685	High Similarity	NPC169973
0.9597	High Similarity	NPC274356
0.9535	High Similarity	NPC184938
0.9535	High Similarity	NPC101624
0.9453	High Similarity	NPC106739
0.9453	High Similarity	NPC471505
0.9385	High Similarity	NPC135777
0.9385	High Similarity	NPC142547
0.9355	High Similarity	NPC317769
0.9355	High Similarity	NPC31344
0.9355	High Similarity	NPC249788
0.9323	High Similarity	NPC472711
0.9185	High Similarity	NPC477898
0.9185	High Similarity	NPC185307
0.9185	High Similarity	NPC470950
0.9173	High Similarity	NPC88640
0.9173	High Similarity	NPC123526
0.9173	High Similarity	NPC193666
0.9154	High Similarity	NPC227002
0.9147	High Similarity	NPC134764
0.9147	High Similarity	NPC171550
0.9141	High Similarity	NPC21867
0.9141	High Similarity	NPC45774
0.9141	High Similarity	NPC11258
0.9141	High Similarity	NPC184733
0.9141	High Similarity	NPC128208
0.9141	High Similarity	NPC129570
0.9141	High Similarity	NPC282703
0.9134	High Similarity	NPC40352
0.9134	High Similarity	NPC213711
0.912	High Similarity	NPC85488
0.9118	High Similarity	NPC129417
0.9118	High Similarity	NPC470235
0.9118	High Similarity	NPC84181
0.9118	High Similarity	NPC283995
0.9111	High Similarity	NPC476356
0.907	High Similarity	NPC475875
0.9062	High Similarity	NPC158737
0.9051	High Similarity	NPC279298
0.9051	High Similarity	NPC22150
0.9051	High Similarity	NPC38041
0.9048	High Similarity	NPC280704
0.9044	High Similarity	NPC46092
0.9032	High Similarity	NPC242885
0.9032	High Similarity	NPC227217
0.9032	High Similarity	NPC95614
0.9032	High Similarity	NPC344161
0.9032	High Similarity	NPC56214
0.9032	High Similarity	NPC232316
0.9032	High Similarity	NPC165133
0.9032	High Similarity	NPC117780
0.9023	High Similarity	NPC52277
0.9023	High Similarity	NPC199459
0.9023	High Similarity	NPC177035
0.9008	High Similarity	NPC104077
0.9008	High Similarity	NPC219671
0.9008	High Similarity	NPC147616
0.9008	High Similarity	NPC259742
0.9	High Similarity	NPC257582
0.9	High Similarity	NPC242807
0.9	High Similarity	NPC153739
0.9	High Similarity	NPC42300
0.9	High Similarity	NPC145305
0.9	High Similarity	NPC77040
0.9	High Similarity	NPC241522
0.9	High Similarity	NPC64201
0.9	High Similarity	NPC187998
0.9	High Similarity	NPC174495
0.9	High Similarity	NPC92164
0.8986	High Similarity	NPC112861
0.8978	High Similarity	NPC187774
0.8978	High Similarity	NPC472713
0.8978	High Similarity	NPC472712
0.8978	High Similarity	NPC118385
0.8978	High Similarity	NPC473046
0.8971	High Similarity	NPC253878
0.8963	High Similarity	NPC177868
0.8955	High Similarity	NPC474039
0.8952	High Similarity	NPC310338
0.8952	High Similarity	NPC281298
0.8931	High Similarity	NPC228346
0.8931	High Similarity	NPC40432
0.8931	High Similarity	NPC27843
0.8931	High Similarity	NPC115207
0.8931	High Similarity	NPC161557
0.8931	High Similarity	NPC277804
0.8931	High Similarity	NPC7171
0.8931	High Similarity	NPC158079
0.8921	High Similarity	NPC193473
0.8921	High Similarity	NPC114505
0.8921	High Similarity	NPC213074
0.8921	High Similarity	NPC39657
0.8921	High Similarity	NPC31325
0.8921	High Similarity	NPC224674
0.8921	High Similarity	NPC275284
0.8921	High Similarity	NPC15956
0.8913	High Similarity	NPC18979
0.8905	High Similarity	NPC265154
0.8905	High Similarity	NPC278961
0.8905	High Similarity	NPC255566
0.8905	High Similarity	NPC113680
0.8905	High Similarity	NPC298317
0.8897	High Similarity	NPC471414
0.8897	High Similarity	NPC166137
0.8897	High Similarity	NPC282291
0.8889	High Similarity	NPC160380
0.8889	High Similarity	NPC301641
0.8889	High Similarity	NPC80241
0.8889	High Similarity	NPC156376
0.8889	High Similarity	NPC38996
0.8872	High Similarity	NPC470881
0.8872	High Similarity	NPC67247
0.8871	High Similarity	NPC470626
0.8864	High Similarity	NPC181049
0.8864	High Similarity	NPC207400
0.8846	High Similarity	NPC226862
0.8846	High Similarity	NPC470084
0.8846	High Similarity	NPC165128
0.8846	High Similarity	NPC158471
0.8846	High Similarity	NPC57119
0.8841	High Similarity	NPC253015
0.8841	High Similarity	NPC471065
0.8832	High Similarity	NPC52664
0.8832	High Similarity	NPC5262
0.8832	High Similarity	NPC246947
0.8832	High Similarity	NPC472714
0.8832	High Similarity	NPC302506
0.8824	High Similarity	NPC284464
0.8815	High Similarity	NPC185908
0.8815	High Similarity	NPC281780
0.8815	High Similarity	NPC304152
0.8815	High Similarity	NPC138738
0.8815	High Similarity	NPC470413
0.881	High Similarity	NPC207613
0.8806	High Similarity	NPC236522
0.8806	High Similarity	NPC18576
0.8797	High Similarity	NPC158331
0.8797	High Similarity	NPC6836
0.8797	High Similarity	NPC196937
0.8794	High Similarity	NPC51328
0.8794	High Similarity	NPC286235
0.8794	High Similarity	NPC55158
0.879	High Similarity	NPC293619
0.8788	High Similarity	NPC65942
0.8788	High Similarity	NPC248307
0.8779	High Similarity	NPC476748
0.8777	High Similarity	NPC272619
0.8777	High Similarity	NPC43508
0.8777	High Similarity	NPC476301
0.8777	High Similarity	NPC286245
0.8769	High Similarity	NPC165045
0.8769	High Similarity	NPC5428
0.8769	High Similarity	NPC118533
0.8768	High Similarity	NPC185071
0.8768	High Similarity	NPC12728
0.876	High Similarity	NPC148627
0.8759	High Similarity	NPC471908
0.875	High Similarity	NPC30951
0.875	High Similarity	NPC6369
0.8741	High Similarity	NPC471988
0.8741	High Similarity	NPC77861
0.874	High Similarity	NPC54872
0.874	High Similarity	NPC470212
0.874	High Similarity	NPC312675
0.874	High Similarity	NPC473853
0.874	High Similarity	NPC113865
0.874	High Similarity	NPC262156
0.874	High Similarity	NPC324571
0.874	High Similarity	NPC184651
0.874	High Similarity	NPC343720
0.8732	High Similarity	NPC475224
0.8732	High Similarity	NPC98624
0.8731	High Similarity	NPC471942
0.8731	High Similarity	NPC287745
0.8731	High Similarity	NPC176814
0.8731	High Similarity	NPC35731
0.8731	High Similarity	NPC4982
0.8731	High Similarity	NPC68779
0.8731	High Similarity	NPC300776
0.8731	High Similarity	NPC187616
0.8731	High Similarity	NPC47181
0.8731	High Similarity	NPC193026
0.8731	High Similarity	NPC49603
0.8731	High Similarity	NPC5310
0.8723	High Similarity	NPC130449
0.8723	High Similarity	NPC226153
0.8723	High Similarity	NPC304048
0.8723	High Similarity	NPC248132
0.8722	High Similarity	NPC4940
0.8722	High Similarity	NPC252833
0.8722	High Similarity	NPC97316
0.8722	High Similarity	NPC175067
0.8722	High Similarity	NPC204215
0.872	High Similarity	NPC474040
0.8712	High Similarity	NPC271208
0.8712	High Similarity	NPC63574
0.8712	High Similarity	NPC233224

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 NPC476345 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	858
0.2-0.3	1605
0.3-0.4	2735
0.4-0.5	1884
0.5-0.6	1089
0.6-0.7	607
0.7-0.8	92
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8468	Intermediate Similarity	NPD5283	Phase 1
0.845	Intermediate Similarity	NPD3705	Approved
0.8359	Intermediate Similarity	NPD1357	Approved
0.8358	Intermediate Similarity	NPD3027	Phase 3
0.8306	Intermediate Similarity	NPD228	Approved
0.8145	Intermediate Similarity	NPD3021	Approved
0.8145	Intermediate Similarity	NPD3022	Approved
0.8045	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD3620	Phase 2
0.7972	Intermediate Similarity	NPD6674	Discontinued
0.7958	Intermediate Similarity	NPD7266	Discontinued
0.7914	Intermediate Similarity	NPD4060	Phase 1
0.7908	Intermediate Similarity	NPD6234	Discontinued
0.7877	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1613	Approved
0.7785	Intermediate Similarity	NPD7228	Approved
0.7769	Intermediate Similarity	NPD7157	Approved
0.7763	Intermediate Similarity	NPD2977	Approved
0.7763	Intermediate Similarity	NPD2978	Approved
0.7754	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD37	Approved
0.7681	Intermediate Similarity	NPD2861	Phase 2
0.7681	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7843	Approved
0.7662	Intermediate Similarity	NPD4966	Approved
0.7662	Intermediate Similarity	NPD4965	Approved
0.7662	Intermediate Similarity	NPD4967	Phase 2
0.7647	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD2684	Approved
0.7606	Intermediate Similarity	NPD6355	Discontinued
0.7571	Intermediate Similarity	NPD7095	Approved
0.7569	Intermediate Similarity	NPD4108	Discontinued
0.7551	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4110	Phase 3
0.7532	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD6671	Approved
0.7468	Intermediate Similarity	NPD7199	Phase 2
0.7466	Intermediate Similarity	NPD1375	Discontinued
0.7453	Intermediate Similarity	NPD3818	Discontinued
0.7451	Intermediate Similarity	NPD7028	Phase 2
0.7434	Intermediate Similarity	NPD1653	Approved
0.7432	Intermediate Similarity	NPD6331	Phase 2
0.7419	Intermediate Similarity	NPD3020	Approved
0.7413	Intermediate Similarity	NPD1558	Phase 1
0.7394	Intermediate Similarity	NPD5109	Approved
0.7394	Intermediate Similarity	NPD5110	Phase 2
0.7394	Intermediate Similarity	NPD5111	Phase 2
0.7383	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7685	Pre-registration
0.7376	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4908	Phase 1
0.7375	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7074	Phase 3
0.7361	Intermediate Similarity	NPD5735	Approved
0.7357	Intermediate Similarity	NPD6584	Phase 3
0.7344	Intermediate Similarity	NPD968	Approved
0.7343	Intermediate Similarity	NPD2674	Phase 3
0.7333	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5058	Phase 3
0.731	Intermediate Similarity	NPD6653	Approved
0.7305	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7054	Approved
0.7279	Intermediate Similarity	NPD2161	Phase 2
0.7273	Intermediate Similarity	NPD3145	Approved
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3144	Approved
0.7273	Intermediate Similarity	NPD7240	Approved
0.7266	Intermediate Similarity	NPD2983	Phase 2
0.7266	Intermediate Similarity	NPD5327	Phase 3
0.7266	Intermediate Similarity	NPD2982	Phase 2
0.726	Intermediate Similarity	NPD6895	Approved
0.726	Intermediate Similarity	NPD7097	Phase 1
0.726	Intermediate Similarity	NPD6896	Approved
0.7256	Intermediate Similarity	NPD7472	Approved
0.7248	Intermediate Similarity	NPD4236	Phase 3
0.7248	Intermediate Similarity	NPD4237	Approved
0.7248	Intermediate Similarity	NPD3060	Approved
0.7246	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1610	Phase 2
0.7244	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3657	Discovery
0.723	Intermediate Similarity	NPD5763	Approved
0.723	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD5846	Approved
0.7226	Intermediate Similarity	NPD6516	Phase 2
0.7222	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8166	Discontinued
0.7194	Intermediate Similarity	NPD2230	Approved
0.7194	Intermediate Similarity	NPD2981	Phase 2
0.7194	Intermediate Similarity	NPD2233	Approved
0.7194	Intermediate Similarity	NPD2232	Approved
0.7183	Intermediate Similarity	NPD3018	Phase 2
0.7183	Intermediate Similarity	NPD9494	Approved
0.7177	Intermediate Similarity	NPD2860	Approved
0.7177	Intermediate Similarity	NPD2859	Approved
0.7172	Intermediate Similarity	NPD4140	Approved
0.7153	Intermediate Similarity	NPD6798	Discontinued
0.7153	Intermediate Similarity	NPD5585	Approved
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD3685	Discontinued
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7134	Intermediate Similarity	NPD1934	Approved
0.7133	Intermediate Similarity	NPD4162	Approved
0.7133	Intermediate Similarity	NPD5177	Phase 3
0.7114	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4624	Approved
0.7111	Intermediate Similarity	NPD709	Approved
0.7111	Intermediate Similarity	NPD6387	Discontinued
0.7107	Intermediate Similarity	NPD3882	Suspended
0.7103	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD5126	Approved
0.7101	Intermediate Similarity	NPD2668	Approved
0.7101	Intermediate Similarity	NPD2667	Approved
0.7101	Intermediate Similarity	NPD5125	Phase 3
0.7101	Intermediate Similarity	NPD4626	Approved
0.7097	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD9296	Approved
0.7097	Intermediate Similarity	NPD2934	Approved
0.7095	Intermediate Similarity	NPD5588	Approved
0.7092	Intermediate Similarity	NPD8651	Approved
0.7092	Intermediate Similarity	NPD1283	Approved
0.7086	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1182	Approved
0.7078	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD52	Approved
0.7078	Intermediate Similarity	NPD7526	Approved
0.7075	Intermediate Similarity	NPD6353	Approved
0.7071	Intermediate Similarity	NPD2231	Phase 2
0.7071	Intermediate Similarity	NPD2235	Phase 2
0.7071	Intermediate Similarity	NPD1840	Phase 2
0.7067	Intermediate Similarity	NPD7037	Approved
0.7066	Intermediate Similarity	NPD7251	Discontinued
0.7063	Intermediate Similarity	NPD7833	Phase 2
0.7063	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7831	Phase 2
0.7063	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2979	Phase 3
0.7051	Intermediate Similarity	NPD7458	Discontinued
0.705	Intermediate Similarity	NPD3496	Discontinued
0.705	Intermediate Similarity	NPD3847	Discontinued
0.7045	Intermediate Similarity	NPD5451	Approved
0.7042	Intermediate Similarity	NPD3094	Phase 2
0.7039	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5241	Discontinued
0.7034	Intermediate Similarity	NPD5718	Phase 2
0.7029	Intermediate Similarity	NPD5691	Approved
0.7027	Intermediate Similarity	NPD4536	Approved
0.7027	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4538	Approved
0.7024	Intermediate Similarity	NPD7808	Phase 3
0.7023	Intermediate Similarity	NPD290	Approved
0.7023	Intermediate Similarity	NPD1358	Approved
0.702	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1138	Approved
0.7013	Intermediate Similarity	NPD4123	Phase 3
0.7013	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6797	Phase 2
0.7	Intermediate Similarity	NPD3092	Approved
0.6986	Remote Similarity	NPD4062	Phase 3
0.6981	Remote Similarity	NPD8455	Phase 2
0.6981	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2801	Approved
0.6974	Remote Similarity	NPD4628	Phase 3
0.6972	Remote Similarity	NPD6696	Suspended
0.6972	Remote Similarity	NPD2922	Phase 1
0.6968	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2492	Phase 1
0.6957	Remote Similarity	NPD3091	Approved
0.6957	Remote Similarity	NPD5604	Discontinued
0.6957	Remote Similarity	NPD1548	Phase 1
0.6954	Remote Similarity	NPD5958	Discontinued
0.695	Remote Similarity	NPD1608	Approved
0.6949	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3134	Approved
0.6944	Remote Similarity	NPD5736	Approved
0.694	Remote Similarity	NPD1137	Approved
0.694	Remote Similarity	NPD1139	Approved
0.6939	Remote Similarity	NPD2238	Phase 2
0.6933	Remote Similarity	NPD2438	Suspended
0.6933	Remote Similarity	NPD2935	Discontinued
0.6933	Remote Similarity	NPD8127	Discontinued
0.6933	Remote Similarity	NPD6032	Approved
0.6923	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7119	Phase 2
0.6909	Remote Similarity	NPD2489	Approved
0.6909	Remote Similarity	NPD27	Approved
0.6906	Remote Similarity	NPD1651	Approved
0.6903	Remote Similarity	NPD4739	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