NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	694.23
Volume:	677.219
LogP:	2.487
LogD:	2.623
LogS:	-3.942
# Rotatable Bonds:	14
TPSA:	199.9
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.099
Synthetic Accessibility Score:	4.764
Fsp3:	0.333
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.567
MDCK Permeability:	1.2460836842365097e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.83
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	98.02123260498047%
Volume Distribution (VD):	0.395
Pgp-substrate:	4.983678817749023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.379
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.321
CYP2C9-inhibitor:	0.286
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.526
CYP3A4-inhibitor:	0.415
CYP3A4-substrate:	0.665

ADMET: Excretion

Clearance (CL):	2.766
Half-life (T1/2):	0.623

ADMET: Toxicity

hERG Blockers:	0.267
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.171
AMES Toxicity:	0.526
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.85
Skin Sensitization:	0.948
Carcinogencity:	0.377
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.059

Download Data

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

Natural Product: NPC478267

Natural Product ID:	NPC478267
*Common Name:**	Ovatoside A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NEHBIXYYFGPSPV-URKWQAFXSA-N
Standard InCHI:	InChI=1S/C36H38O14/c1-44-26-14-19(6-9-24(26)38)7-11-30(40)47-18-29-31(41)32(42)33(43)36(49-29)48-17-23-22-13-20(5-4-12-37)15-28(46-3)35(22)50-34(23)21-8-10-25(39)27(16-21)45-2/h4-16,23,29,31-34,36,38-39,41-43H,17-18H2,1-3H3/b5-4+,11-7+/t23?,29?,31-,32+,33?,34?,36-/m1/s1
SMILES:	[H]C(=O)/C=C/C1=CC2=C(OC(C3=CC=C(O)C(OC)=C3)C2CO[C@@H]2OC(COC(=O)/C=C/C3=CC(OC)=C(O)C=C3)[C@@H](O)[C@H](O)C2O)C(OC)=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9835	Catalpa ovata	Species	Bignoniaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478267 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	353
0.1-0.2	1483
0.2-0.3	3322
0.3-0.4	7914
0.4-0.5	9766
0.5-0.6	5386
0.6-0.7	7708
0.7-0.8	5801
0.8-0.85	755
0.85-0.9	189
0.9-0.95	20
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC478269
0.9481	High Similarity	NPC11411
0.9474	High Similarity	NPC478268
0.9355	High Similarity	NPC228357
0.9286	High Similarity	NPC115203
0.9241	High Similarity	NPC7191
0.9241	High Similarity	NPC149873
0.9202	High Similarity	NPC316539
0.9193	High Similarity	NPC208818
0.9145	High Similarity	NPC193473
0.9145	High Similarity	NPC224674
0.9145	High Similarity	NPC114505
0.9145	High Similarity	NPC15956
0.9145	High Similarity	NPC31325
0.9145	High Similarity	NPC213074
0.9145	High Similarity	NPC275284
0.9085	High Similarity	NPC3460
0.9085	High Similarity	NPC28651
0.9085	High Similarity	NPC80732
0.9085	High Similarity	NPC300262
0.9085	High Similarity	NPC201148
0.9085	High Similarity	NPC192763
0.9085	High Similarity	NPC210611
0.9085	High Similarity	NPC215095
0.9085	High Similarity	NPC199311
0.9085	High Similarity	NPC261122
0.9051	High Similarity	NPC125495
0.9051	High Similarity	NPC470827
0.9038	High Similarity	NPC470769
0.9013	High Similarity	NPC163898
0.9013	High Similarity	NPC43508
0.9013	High Similarity	NPC476301
0.9012	High Similarity	NPC59516
0.8994	High Similarity	NPC173726
0.8994	High Similarity	NPC241600
0.8994	High Similarity	NPC470828
0.8974	High Similarity	NPC302610
0.8968	High Similarity	NPC470934
0.8968	High Similarity	NPC188393
0.8968	High Similarity	NPC98624
0.8961	High Similarity	NPC236166
0.8954	High Similarity	NPC199928
0.8947	High Similarity	NPC471667
0.8947	High Similarity	NPC232228
0.8947	High Similarity	NPC474444
0.8947	High Similarity	NPC284881
0.8947	High Similarity	NPC264706
0.8947	High Similarity	NPC79429
0.8947	High Similarity	NPC217635
0.8947	High Similarity	NPC93433
0.891	High Similarity	NPC7145
0.891	High Similarity	NPC85192
0.891	High Similarity	NPC125823
0.891	High Similarity	NPC143480
0.8889	High Similarity	NPC262182
0.8889	High Similarity	NPC34587
0.8889	High Similarity	NPC252292
0.8889	High Similarity	NPC287615
0.8889	High Similarity	NPC476382
0.8889	High Similarity	NPC34927
0.8889	High Similarity	NPC216819
0.8889	High Similarity	NPC83743
0.8889	High Similarity	NPC100998
0.8882	High Similarity	NPC478239
0.8882	High Similarity	NPC185307
0.8882	High Similarity	NPC470950
0.8854	High Similarity	NPC289967
0.8854	High Similarity	NPC472611
0.8854	High Similarity	NPC472612
0.8846	High Similarity	NPC476871
0.8846	High Similarity	NPC472710
0.8846	High Similarity	NPC472709
0.8831	High Similarity	NPC476865
0.8827	High Similarity	NPC12326
0.8824	High Similarity	NPC129417
0.8824	High Similarity	NPC110063
0.8824	High Similarity	NPC292443
0.8824	High Similarity	NPC470235
0.8824	High Similarity	NPC283995
0.8816	High Similarity	NPC253878
0.8816	High Similarity	NPC67467
0.8816	High Similarity	NPC140502
0.8816	High Similarity	NPC131971
0.8816	High Similarity	NPC157816
0.8816	High Similarity	NPC476356
0.8797	High Similarity	NPC245615
0.8797	High Similarity	NPC299706
0.8797	High Similarity	NPC150442
0.8797	High Similarity	NPC115466
0.8797	High Similarity	NPC61604
0.8782	High Similarity	NPC44452
0.8782	High Similarity	NPC106138
0.8782	High Similarity	NPC181452
0.8782	High Similarity	NPC476386
0.8782	High Similarity	NPC220006
0.8782	High Similarity	NPC471062
0.8782	High Similarity	NPC470933
0.8782	High Similarity	NPC475940
0.8782	High Similarity	NPC476398
0.8782	High Similarity	NPC94871
0.8782	High Similarity	NPC474893
0.8782	High Similarity	NPC473427
0.8782	High Similarity	NPC259347
0.8782	High Similarity	NPC306890
0.8774	High Similarity	NPC232992
0.8766	High Similarity	NPC476864
0.8766	High Similarity	NPC38041
0.8766	High Similarity	NPC143120
0.8766	High Similarity	NPC476869
0.8766	High Similarity	NPC476866
0.8766	High Similarity	NPC473909
0.8766	High Similarity	NPC476868
0.8766	High Similarity	NPC22150
0.8766	High Similarity	NPC138915
0.8766	High Similarity	NPC274960
0.8766	High Similarity	NPC279298
0.8765	High Similarity	NPC216916
0.8765	High Similarity	NPC469889
0.8758	High Similarity	NPC46092
0.8758	High Similarity	NPC215400
0.8758	High Similarity	NPC230531
0.875	High Similarity	NPC186406
0.875	High Similarity	NPC67629
0.875	High Similarity	NPC79736
0.875	High Similarity	NPC471414
0.875	High Similarity	NPC472711
0.8734	High Similarity	NPC474442
0.8734	High Similarity	NPC169404
0.8734	High Similarity	NPC176186
0.8734	High Similarity	NPC53587
0.8726	High Similarity	NPC470927
0.8726	High Similarity	NPC475224
0.8726	High Similarity	NPC257970
0.8718	High Similarity	NPC473408
0.8718	High Similarity	NPC102934
0.8718	High Similarity	NPC270751
0.8718	High Similarity	NPC474795
0.8718	High Similarity	NPC252402
0.8718	High Similarity	NPC474834
0.8718	High Similarity	NPC159697
0.8718	High Similarity	NPC117788
0.8718	High Similarity	NPC290902
0.8718	High Similarity	NPC474856
0.8718	High Similarity	NPC226153
0.8718	High Similarity	NPC291326
0.8718	High Similarity	NPC474940
0.8718	High Similarity	NPC130959
0.8718	High Similarity	NPC303013
0.8718	High Similarity	NPC304048
0.871	High Similarity	NPC112861
0.8701	High Similarity	NPC471063
0.8701	High Similarity	NPC476867
0.8698	High Similarity	NPC267549
0.869	High Similarity	NPC193377
0.8688	High Similarity	NPC131532
0.8667	High Similarity	NPC475621
0.8662	High Similarity	NPC90896
0.8662	High Similarity	NPC283839
0.8659	High Similarity	NPC45943
0.8654	High Similarity	NPC39657
0.8645	High Similarity	NPC18979
0.8645	High Similarity	NPC286245
0.8645	High Similarity	NPC272619
0.8636	High Similarity	NPC278961
0.8636	High Similarity	NPC113680
0.8636	High Similarity	NPC477898
0.8634	High Similarity	NPC163635
0.8618	High Similarity	NPC100389
0.8618	High Similarity	NPC226005
0.8616	High Similarity	NPC59692
0.8616	High Similarity	NPC470264
0.8614	High Similarity	NPC286809
0.8608	High Similarity	NPC158635
0.8608	High Similarity	NPC229882
0.8608	High Similarity	NPC183380
0.8599	High Similarity	NPC93924
0.859	High Similarity	NPC268515
0.859	High Similarity	NPC260397
0.859	High Similarity	NPC205796
0.859	High Similarity	NPC93610
0.859	High Similarity	NPC276753
0.859	High Similarity	NPC241846
0.859	High Similarity	NPC40222
0.8581	High Similarity	NPC296954
0.8581	High Similarity	NPC300894
0.8581	High Similarity	NPC141455
0.8581	High Similarity	NPC253015
0.8581	High Similarity	NPC196063
0.8581	High Similarity	NPC471065
0.8581	High Similarity	NPC84181
0.8571	High Similarity	NPC246947
0.8571	High Similarity	NPC302506
0.8562	High Similarity	NPC106944
0.8562	High Similarity	NPC200645
0.8562	High Similarity	NPC106669
0.8562	High Similarity	NPC475227
0.8562	High Similarity	NPC202700
0.8553	High Similarity	NPC126206
0.8553	High Similarity	NPC138738
0.8553	High Similarity	NPC470413

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 NPC478267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	881
0.2-0.3	1728
0.3-0.4	2734
0.4-0.5	1867
0.5-0.6	1012
0.6-0.7	542
0.7-0.8	91
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8497	Intermediate Similarity	NPD7266	Discontinued
0.8313	Intermediate Similarity	NPD1653	Approved
0.8284	Intermediate Similarity	NPD7228	Approved
0.8269	Intermediate Similarity	NPD6674	Discontinued
0.8171	Intermediate Similarity	NPD8455	Phase 2
0.8114	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6559	Discontinued
0.8084	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD8313	Approved
0.7989	Intermediate Similarity	NPD7685	Pre-registration
0.7988	Intermediate Similarity	NPD7199	Phase 2
0.7977	Intermediate Similarity	NPD7074	Phase 3
0.7965	Intermediate Similarity	NPD3818	Discontinued
0.7964	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD4966	Approved
0.7964	Intermediate Similarity	NPD4965	Approved
0.7964	Intermediate Similarity	NPD4967	Phase 2
0.7919	Intermediate Similarity	NPD7054	Approved
0.7874	Intermediate Similarity	NPD7472	Approved
0.784	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD5844	Phase 1
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7240	Approved
0.7778	Intermediate Similarity	NPD8127	Discontinued
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1613	Approved
0.7756	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7808	Phase 3
0.774	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7251	Discontinued
0.7644	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6166	Phase 2
0.7643	Intermediate Similarity	NPD4060	Phase 1
0.7628	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6797	Phase 2
0.7627	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7680	Approved
0.7564	Intermediate Similarity	NPD3027	Phase 3
0.7529	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1934	Approved
0.7447	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2861	Phase 2
0.7414	Intermediate Similarity	NPD5494	Approved
0.7401	Intermediate Similarity	NPD7473	Discontinued
0.7399	Intermediate Similarity	NPD7075	Discontinued
0.7386	Intermediate Similarity	NPD1091	Approved
0.7384	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5124	Phase 1
0.7375	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5762	Approved
0.7362	Intermediate Similarity	NPD5763	Approved
0.7349	Intermediate Similarity	NPD5058	Phase 3
0.7348	Intermediate Similarity	NPD7549	Discontinued
0.7341	Intermediate Similarity	NPD7768	Phase 2
0.733	Intermediate Similarity	NPD6232	Discontinued
0.7326	Intermediate Similarity	NPD1465	Phase 2
0.7326	Intermediate Similarity	NPD7819	Suspended
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7289	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7251	Intermediate Similarity	NPD4380	Phase 2
0.7241	Intermediate Similarity	NPD3882	Suspended
0.7229	Intermediate Similarity	NPD8166	Discontinued
0.7229	Intermediate Similarity	NPD4628	Phase 3
0.7225	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7411	Suspended
0.7205	Intermediate Similarity	NPD3620	Phase 2
0.7205	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7184	Intermediate Similarity	NPD3817	Phase 2
0.7179	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8651	Approved
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2801	Approved
0.7125	Intermediate Similarity	NPD7095	Approved
0.7121	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7783	Phase 2
0.7107	Intermediate Similarity	NPD8151	Discontinued
0.7099	Intermediate Similarity	NPD4140	Approved
0.7078	Intermediate Similarity	NPD1357	Approved
0.7072	Intermediate Similarity	NPD3751	Discontinued
0.7069	Intermediate Similarity	NPD6801	Discontinued
0.7066	Intermediate Similarity	NPD1652	Phase 2
0.7059	Intermediate Similarity	NPD6843	Phase 3
0.7059	Intermediate Similarity	NPD6841	Approved
0.7059	Intermediate Similarity	NPD6842	Approved
0.7059	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7906	Approved
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.7048	Intermediate Similarity	NPD6002	Phase 3
0.7048	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6004	Phase 3
0.7048	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6005	Phase 3
0.7039	Intermediate Similarity	NPD7229	Phase 3
0.7037	Intermediate Similarity	NPD6233	Phase 2
0.703	Intermediate Similarity	NPD5588	Approved
0.7026	Intermediate Similarity	NPD7435	Discontinued
0.7024	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4110	Phase 3
0.7018	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6273	Approved
0.7012	Intermediate Similarity	NPD6653	Approved
0.7006	Intermediate Similarity	NPD2424	Discontinued
0.6989	Remote Similarity	NPD5402	Approved
0.6988	Remote Similarity	NPD2935	Discontinued
0.6983	Remote Similarity	NPD6959	Discontinued
0.6975	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4536	Approved
0.697	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4538	Approved
0.6966	Remote Similarity	NPD919	Approved
0.6961	Remote Similarity	NPD27	Approved
0.6961	Remote Similarity	NPD2489	Approved
0.6959	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7028	Phase 2
0.6951	Remote Similarity	NPD1933	Approved
0.6951	Remote Similarity	NPD5735	Approved
0.6944	Remote Similarity	NPD3787	Discontinued
0.6944	Remote Similarity	NPD3051	Approved
0.6941	Remote Similarity	NPD6667	Approved
0.6941	Remote Similarity	NPD6666	Approved
0.6935	Remote Similarity	NPD7312	Approved
0.6935	Remote Similarity	NPD7313	Approved
0.6935	Remote Similarity	NPD7310	Approved
0.6935	Remote Similarity	NPD7311	Approved
0.6932	Remote Similarity	NPD2977	Approved
0.6932	Remote Similarity	NPD2978	Approved
0.6928	Remote Similarity	NPD7033	Discontinued
0.6923	Remote Similarity	NPD4626	Approved
0.6923	Remote Similarity	NPD5125	Phase 3
0.6923	Remote Similarity	NPD3750	Approved
0.6923	Remote Similarity	NPD5126	Approved
0.6915	Remote Similarity	NPD4663	Approved
0.6915	Remote Similarity	NPD8150	Discontinued
0.6914	Remote Similarity	NPD4625	Phase 3
0.6914	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5283	Phase 1
0.6908	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2970	Approved
0.6906	Remote Similarity	NPD2969	Approved
0.6904	Remote Similarity	NPD7870	Phase 2
0.6904	Remote Similarity	NPD7871	Phase 2
0.6901	Remote Similarity	NPD1511	Approved
0.69	Remote Similarity	NPD7874	Approved
0.69	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7309	Approved
0.6897	Remote Similarity	NPD3226	Approved
0.6888	Remote Similarity	NPD6823	Phase 2
0.6879	Remote Similarity	NPD5403	Approved
0.6879	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD2797	Approved
0.6872	Remote Similarity	NPD6779	Approved
0.6872	Remote Similarity	NPD6781	Approved
0.6872	Remote Similarity	NPD6776	Approved
0.6872	Remote Similarity	NPD6780	Approved
0.6872	Remote Similarity	NPD6782	Approved
0.6872	Remote Similarity	NPD6777	Approved
0.6872	Remote Similarity	NPD6778	Approved
0.6871	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD4481	Phase 3
0.6867	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5691	Approved
0.6853	Remote Similarity	NPD7696	Phase 3
0.6853	Remote Similarity	NPD7698	Approved
0.6853	Remote Similarity	NPD7697	Approved
0.6848	Remote Similarity	NPD4340	Discontinued
0.6847	Remote Similarity	NPD7930	Approved
0.6845	Remote Similarity	NPD4577	Approved
0.6845	Remote Similarity	NPD4578	Approved
0.6842	Remote Similarity	NPD7843	Approved
0.6835	Remote Similarity	NPD422	Phase 1
0.6833	Remote Similarity	NPD4666	Phase 3
0.6828	Remote Similarity	NPD7038	Approved
0.6828	Remote Similarity	NPD7039	Approved
0.6826	Remote Similarity	NPD5960	Phase 3

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