NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	428.37
Volume:	476.382
LogP:	6.273
LogD:	5.498
LogS:	-5.638
# Rotatable Bonds:	0
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.457
Synthetic Accessibility Score:	5.602
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.136
MDCK Permeability:	5.25631257914938e-05
Pgp-inhibitor:	0.24
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.547

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	94.4607925415039%
Volume Distribution (VD):	1.108
Pgp-substrate:	2.0210952758789062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.504
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.256
CYP3A4-substrate:	0.581

ADMET: Excretion

Clearance (CL):	4.947
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.713
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.149
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.932
Carcinogencity:	0.008
Eye Corrosion:	0.53
Eye Irritation:	0.187
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC477508

Natural Product ID:	NPC477508
*Common Name:**	(1S,4R,5R,8R,10S,13R,14R,17R,18R,19S,20R)-4,5,9,9,13,20-hexamethyl-22-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-10-ol
IUPAC Name:	(1S,4R,5R,8R,10S,13R,14R,17R,18R,19S,20R)-4,5,9,9,13,20-hexamethyl-22-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-10-ol
Synonyms:
Standard InCHIKey:	BRAPVSGNVTYIBT-KPPFHTLOSA-N
Standard InCHI:	InChI=1S/C29H48O2/c1-18-17-31-29-14-9-19(18)24(29)20-7-8-22-26(4)12-11-23(30)25(2,3)21(26)10-13-28(22,6)27(20,5)15-16-29/h18-24,30H,7-17H2,1-6H3/t18-,19-,20+,21-,22+,23-,24+,26-,27+,28+,29-/m0/s1
SMILES:	C[C@H]1CO[C@]23CC[C@@H]1[C@@H]2[C@H]4CC[C@@H]5[C@]6(CC[C@@H](C([C@@H]6CC[C@]5([C@@]4(CC3)C)C)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	25136232
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO24136	Melaleuca ericifolia	Species	Myrtaceae	Eukaryota	leaves	Mansoura, Egypt	2006-JAN	PMID[18826277]
NPO24136	Melaleuca ericifolia	Species	Myrtaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	18100	nM	PMID[18826277]

☑ 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 NPC477508 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	440
0.1-0.2	5090
0.2-0.3	17721
0.3-0.4	8099
0.4-0.5	4439
0.5-0.6	4038
0.6-0.7	2112
0.7-0.8	670
0.8-0.85	72
0.85-0.9	13
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9275	High Similarity	NPC282454
0.9143	High Similarity	NPC157422
0.9143	High Similarity	NPC100586
0.9143	High Similarity	NPC109457
0.9143	High Similarity	NPC473279
0.9118	High Similarity	NPC48079
0.8986	High Similarity	NPC472741
0.8971	High Similarity	NPC142712
0.8857	High Similarity	NPC129829
0.8857	High Similarity	NPC254037
0.8732	High Similarity	NPC231945
0.8732	High Similarity	NPC192192
0.8696	High Similarity	NPC44122
0.8676	High Similarity	NPC281540
0.8676	High Similarity	NPC118937
0.8676	High Similarity	NPC159654
0.8676	High Similarity	NPC167995
0.8649	High Similarity	NPC470145
0.8611	High Similarity	NPC127094
0.8611	High Similarity	NPC157777
0.8611	High Similarity	NPC131506
0.8611	High Similarity	NPC195530
0.8592	High Similarity	NPC477820
0.8571	High Similarity	NPC63190
0.8533	High Similarity	NPC476233
0.8529	High Similarity	NPC114891
0.8493	Intermediate Similarity	NPC253805
0.8493	Intermediate Similarity	NPC153719
0.8472	Intermediate Similarity	NPC63588
0.8472	Intermediate Similarity	NPC251201
0.8472	Intermediate Similarity	NPC232925
0.8421	Intermediate Similarity	NPC42853
0.8382	Intermediate Similarity	NPC148174
0.8382	Intermediate Similarity	NPC218585
0.8382	Intermediate Similarity	NPC71460
0.8378	Intermediate Similarity	NPC304499
0.8356	Intermediate Similarity	NPC127283
0.8356	Intermediate Similarity	NPC187471
0.8356	Intermediate Similarity	NPC252182
0.8356	Intermediate Similarity	NPC8004
0.8356	Intermediate Similarity	NPC1340
0.8356	Intermediate Similarity	NPC470071
0.8333	Intermediate Similarity	NPC241085
0.8333	Intermediate Similarity	NPC66407
0.8333	Intermediate Similarity	NPC107919
0.8333	Intermediate Similarity	NPC299948
0.8333	Intermediate Similarity	NPC470830
0.8312	Intermediate Similarity	NPC49599
0.8312	Intermediate Similarity	NPC220379
0.8312	Intermediate Similarity	NPC49627
0.831	Intermediate Similarity	NPC473230
0.831	Intermediate Similarity	NPC475884
0.8286	Intermediate Similarity	NPC190827
0.8286	Intermediate Similarity	NPC80463
0.8286	Intermediate Similarity	NPC475943
0.8286	Intermediate Similarity	NPC260116
0.8286	Intermediate Similarity	NPC474380
0.8286	Intermediate Similarity	NPC41577
0.8286	Intermediate Similarity	NPC243469
0.8286	Intermediate Similarity	NPC473276
0.8267	Intermediate Similarity	NPC270306
0.8267	Intermediate Similarity	NPC317242
0.8267	Intermediate Similarity	NPC91387
0.8267	Intermediate Similarity	NPC231680
0.8261	Intermediate Similarity	NPC292419
0.8261	Intermediate Similarity	NPC290791
0.8243	Intermediate Similarity	NPC472341
0.8243	Intermediate Similarity	NPC470610
0.8243	Intermediate Similarity	NPC473238
0.8228	Intermediate Similarity	NPC296734
0.8205	Intermediate Similarity	NPC248944
0.8205	Intermediate Similarity	NPC257296
0.8205	Intermediate Similarity	NPC7479
0.8194	Intermediate Similarity	NPC474756
0.8194	Intermediate Similarity	NPC475893
0.8182	Intermediate Similarity	NPC471045
0.8158	Intermediate Similarity	NPC163597
0.8143	Intermediate Similarity	NPC69149
0.8133	Intermediate Similarity	NPC48795
0.8101	Intermediate Similarity	NPC73515
0.8077	Intermediate Similarity	NPC476176
0.8056	Intermediate Similarity	NPC204233
0.8052	Intermediate Similarity	NPC105208
0.8052	Intermediate Similarity	NPC474574
0.8052	Intermediate Similarity	NPC133596
0.8052	Intermediate Similarity	NPC23884
0.8052	Intermediate Similarity	NPC128951
0.8052	Intermediate Similarity	NPC185915
0.8052	Intermediate Similarity	NPC64081
0.8052	Intermediate Similarity	NPC477227
0.8052	Intermediate Similarity	NPC192046
0.8052	Intermediate Similarity	NPC171658
0.8052	Intermediate Similarity	NPC302578
0.8052	Intermediate Similarity	NPC11907
0.8026	Intermediate Similarity	NPC231256
0.8026	Intermediate Similarity	NPC97534
0.8026	Intermediate Similarity	NPC240235
0.8026	Intermediate Similarity	NPC195155
0.8026	Intermediate Similarity	NPC178383
0.8026	Intermediate Similarity	NPC212879
0.8026	Intermediate Similarity	NPC104387
0.8026	Intermediate Similarity	NPC174964
0.8	Intermediate Similarity	NPC249078
0.8	Intermediate Similarity	NPC475388
0.8	Intermediate Similarity	NPC209686
0.8	Intermediate Similarity	NPC236099
0.7949	Intermediate Similarity	NPC471769
0.7949	Intermediate Similarity	NPC477577
0.7949	Intermediate Similarity	NPC18857
0.7949	Intermediate Similarity	NPC67657
0.7945	Intermediate Similarity	NPC469987
0.7941	Intermediate Similarity	NPC162685
0.7941	Intermediate Similarity	NPC476735
0.7927	Intermediate Similarity	NPC232044
0.7927	Intermediate Similarity	NPC273290
0.7922	Intermediate Similarity	NPC93662
0.7922	Intermediate Similarity	NPC86305
0.7922	Intermediate Similarity	NPC78067
0.7922	Intermediate Similarity	NPC278091
0.7922	Intermediate Similarity	NPC5767
0.7922	Intermediate Similarity	NPC14112
0.7922	Intermediate Similarity	NPC475742
0.7895	Intermediate Similarity	NPC192501
0.7895	Intermediate Similarity	NPC475458
0.7895	Intermediate Similarity	NPC192638
0.7895	Intermediate Similarity	NPC25511
0.7895	Intermediate Similarity	NPC62657
0.7895	Intermediate Similarity	NPC228994
0.7895	Intermediate Similarity	NPC10476
0.7867	Intermediate Similarity	NPC478103
0.7848	Intermediate Similarity	NPC287452
0.7848	Intermediate Similarity	NPC81074
0.7848	Intermediate Similarity	NPC477282
0.7838	Intermediate Similarity	NPC99264
0.7831	Intermediate Similarity	NPC471240
0.7821	Intermediate Similarity	NPC248830
0.7821	Intermediate Similarity	NPC202540
0.7821	Intermediate Similarity	NPC212241
0.7821	Intermediate Similarity	NPC143133
0.7821	Intermediate Similarity	NPC212453
0.7821	Intermediate Similarity	NPC298168
0.7821	Intermediate Similarity	NPC221420
0.7821	Intermediate Similarity	NPC119355
0.7805	Intermediate Similarity	NPC227260
0.7805	Intermediate Similarity	NPC474996
0.7794	Intermediate Similarity	NPC135438
0.7792	Intermediate Similarity	NPC196136
0.7792	Intermediate Similarity	NPC3403
0.7792	Intermediate Similarity	NPC158208
0.7792	Intermediate Similarity	NPC243027
0.7778	Intermediate Similarity	NPC470611
0.7778	Intermediate Similarity	NPC289486
0.7778	Intermediate Similarity	NPC61107
0.7765	Intermediate Similarity	NPC228059
0.7763	Intermediate Similarity	NPC232112
0.775	Intermediate Similarity	NPC261616
0.775	Intermediate Similarity	NPC16449
0.7722	Intermediate Similarity	NPC102708
0.7722	Intermediate Similarity	NPC477817
0.7722	Intermediate Similarity	NPC472501
0.7722	Intermediate Similarity	NPC477819
0.7711	Intermediate Similarity	NPC266651
0.7711	Intermediate Similarity	NPC290612
0.7692	Intermediate Similarity	NPC91573
0.7683	Intermediate Similarity	NPC5280
0.7674	Intermediate Similarity	NPC279329
0.7674	Intermediate Similarity	NPC65550
0.7662	Intermediate Similarity	NPC478130
0.7662	Intermediate Similarity	NPC74639
0.7654	Intermediate Similarity	NPC280781
0.7654	Intermediate Similarity	NPC50658
0.7654	Intermediate Similarity	NPC48756
0.7654	Intermediate Similarity	NPC58631
0.7647	Intermediate Similarity	NPC281004
0.7647	Intermediate Similarity	NPC3025
0.7632	Intermediate Similarity	NPC320549
0.7632	Intermediate Similarity	NPC111234
0.7632	Intermediate Similarity	NPC156277
0.7632	Intermediate Similarity	NPC58057
0.7632	Intermediate Similarity	NPC151018
0.7625	Intermediate Similarity	NPC472742
0.7625	Intermediate Similarity	NPC475727
0.7625	Intermediate Similarity	NPC116119
0.7625	Intermediate Similarity	NPC155924
0.7625	Intermediate Similarity	NPC80297
0.7614	Intermediate Similarity	NPC252253
0.7614	Intermediate Similarity	NPC45959
0.7614	Intermediate Similarity	NPC309866
0.7606	Intermediate Similarity	NPC185547
0.7606	Intermediate Similarity	NPC95804
0.7595	Intermediate Similarity	NPC138502
0.7595	Intermediate Similarity	NPC475031
0.7595	Intermediate Similarity	NPC260301
0.7595	Intermediate Similarity	NPC307336
0.7586	Intermediate Similarity	NPC36372
0.7586	Intermediate Similarity	NPC59006
0.7586	Intermediate Similarity	NPC293609
0.7586	Intermediate Similarity	NPC473830
0.7586	Intermediate Similarity	NPC204881
0.7571	Intermediate Similarity	NPC95958

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 NPC477508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	447
0.1-0.2	4586
0.2-0.3	3015
0.3-0.4	619
0.4-0.5	177
0.5-0.6	223
0.6-0.7	58
0.7-0.8	23
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8472	Intermediate Similarity	NPD4787	Phase 1
0.8333	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6928	Phase 2
0.7632	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4244	Approved
0.75	Intermediate Similarity	NPD4245	Approved
0.7468	Intermediate Similarity	NPD6117	Approved
0.7436	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6116	Phase 1
0.7368	Intermediate Similarity	NPD3698	Phase 2
0.7368	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3702	Approved
0.7317	Intermediate Similarity	NPD7525	Registered
0.7303	Intermediate Similarity	NPD8171	Discontinued
0.7284	Intermediate Similarity	NPD6697	Approved
0.7284	Intermediate Similarity	NPD6118	Approved
0.7284	Intermediate Similarity	NPD6114	Approved
0.7284	Intermediate Similarity	NPD6115	Approved
0.7237	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5360	Phase 3
0.7195	Intermediate Similarity	NPD7645	Phase 2
0.7125	Intermediate Similarity	NPD3703	Phase 2
0.7093	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4789	Approved
0.6962	Remote Similarity	NPD5777	Approved
0.6905	Remote Similarity	NPD4748	Discontinued
0.6842	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8034	Phase 2
0.6813	Remote Similarity	NPD8035	Phase 2
0.6774	Remote Similarity	NPD7991	Discontinued
0.675	Remote Similarity	NPD4758	Discontinued
0.6707	Remote Similarity	NPD7339	Approved
0.6707	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD3671	Phase 1
0.6582	Remote Similarity	NPD6705	Phase 1
0.6566	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4243	Approved
0.6494	Remote Similarity	NPD371	Approved
0.6471	Remote Similarity	NPD5364	Discontinued
0.6386	Remote Similarity	NPD6926	Approved
0.6386	Remote Similarity	NPD6924	Approved
0.6386	Remote Similarity	NPD4784	Approved
0.6386	Remote Similarity	NPD4785	Approved
0.6383	Remote Similarity	NPD4202	Approved
0.6374	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6700	Approved
0.6341	Remote Similarity	NPD6081	Approved
0.6329	Remote Similarity	NPD4224	Phase 2
0.6324	Remote Similarity	NPD385	Approved
0.6324	Remote Similarity	NPD384	Approved
0.6277	Remote Similarity	NPD6702	Approved
0.6277	Remote Similarity	NPD6703	Approved
0.6275	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8308	Discontinued
0.6237	Remote Similarity	NPD5328	Approved
0.6235	Remote Similarity	NPD6933	Approved
0.6224	Remote Similarity	NPD7638	Approved
0.6222	Remote Similarity	NPD4786	Approved
0.6176	Remote Similarity	NPD6402	Approved
0.6176	Remote Similarity	NPD7128	Approved
0.6176	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD6675	Approved
0.6176	Remote Similarity	NPD6920	Discontinued
0.6162	Remote Similarity	NPD7639	Approved
0.6162	Remote Similarity	NPD7640	Approved
0.6146	Remote Similarity	NPD7748	Approved
0.6122	Remote Similarity	NPD4755	Approved
0.6118	Remote Similarity	NPD4190	Phase 3
0.6118	Remote Similarity	NPD5275	Approved
0.6111	Remote Similarity	NPD6695	Phase 3
0.6105	Remote Similarity	NPD6079	Approved
0.6105	Remote Similarity	NPD7515	Phase 2
0.61	Remote Similarity	NPD4159	Approved
0.6087	Remote Similarity	NPD3618	Phase 1
0.6058	Remote Similarity	NPD6881	Approved
0.6058	Remote Similarity	NPD6899	Approved
0.6058	Remote Similarity	NPD7320	Approved
0.6044	Remote Similarity	NPD3665	Phase 1
0.6044	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD3133	Approved
0.6044	Remote Similarity	NPD3666	Approved
0.604	Remote Similarity	NPD7632	Discontinued
0.6036	Remote Similarity	NPD8377	Approved
0.6036	Remote Similarity	NPD8294	Approved
0.6023	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD1811	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD1810	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5982	Remote Similarity	NPD8380	Approved
0.5982	Remote Similarity	NPD8378	Approved
0.5982	Remote Similarity	NPD8379	Approved
0.5982	Remote Similarity	NPD8296	Approved
0.5982	Remote Similarity	NPD8335	Approved
0.5982	Remote Similarity	NPD8033	Approved
0.5962	Remote Similarity	NPD5701	Approved
0.5962	Remote Similarity	NPD5697	Approved
0.596	Remote Similarity	NPD7902	Approved
0.596	Remote Similarity	NPD7919	Phase 3
0.596	Remote Similarity	NPD6083	Phase 2
0.596	Remote Similarity	NPD7920	Phase 3
0.596	Remote Similarity	NPD6084	Phase 2
0.5957	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6931	Approved
0.5955	Remote Similarity	NPD6930	Phase 2
0.5955	Remote Similarity	NPD7509	Discontinued
0.5952	Remote Similarity	NPD7152	Approved
0.5952	Remote Similarity	NPD7151	Approved
0.5952	Remote Similarity	NPD7150	Approved
0.5946	Remote Similarity	NPD7516	Approved
0.5943	Remote Similarity	NPD7102	Approved
0.5943	Remote Similarity	NPD7290	Approved
0.5943	Remote Similarity	NPD6883	Approved
0.5941	Remote Similarity	NPD5223	Approved
0.5926	Remote Similarity	NPD8133	Approved
0.5905	Remote Similarity	NPD6011	Approved
0.5905	Remote Similarity	NPD6415	Discontinued
0.5904	Remote Similarity	NPD6923	Approved
0.5904	Remote Similarity	NPD6922	Approved
0.59	Remote Similarity	NPD8088	Phase 1
0.5895	Remote Similarity	NPD4753	Phase 2
0.5895	Remote Similarity	NPD6051	Approved
0.5888	Remote Similarity	NPD8130	Phase 1
0.5888	Remote Similarity	NPD6847	Approved
0.5888	Remote Similarity	NPD6617	Approved
0.5888	Remote Similarity	NPD6649	Approved
0.5888	Remote Similarity	NPD6869	Approved
0.5888	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD5224	Approved
0.5882	Remote Similarity	NPD5211	Phase 2
0.5882	Remote Similarity	NPD5225	Approved
0.5882	Remote Similarity	NPD5226	Approved
0.5882	Remote Similarity	NPD4633	Approved
0.5876	Remote Similarity	NPD6399	Phase 3
0.5851	Remote Similarity	NPD7524	Approved
0.5851	Remote Similarity	NPD7750	Discontinued
0.5849	Remote Similarity	NPD6012	Approved
0.5849	Remote Similarity	NPD6013	Approved
0.5849	Remote Similarity	NPD6014	Approved
0.5843	Remote Similarity	NPD6929	Approved
0.5842	Remote Similarity	NPD8418	Phase 2
0.5833	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD7143	Approved
0.5833	Remote Similarity	NPD7144	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.5825	Remote Similarity	NPD7986	Approved
0.5825	Remote Similarity	NPD7912	Approved
0.5825	Remote Similarity	NPD5174	Approved
0.5825	Remote Similarity	NPD5175	Approved
0.5825	Remote Similarity	NPD7911	Approved
0.5825	Remote Similarity	NPD7987	Approved
0.5825	Remote Similarity	NPD4754	Approved
0.5824	Remote Similarity	NPD4221	Approved
0.5824	Remote Similarity	NPD4223	Phase 3
0.5806	Remote Similarity	NPD5329	Approved
0.5795	Remote Similarity	NPD6932	Approved
0.5789	Remote Similarity	NPD586	Phase 1
0.5769	Remote Similarity	NPD5141	Approved
0.5769	Remote Similarity	NPD3198	Approved
0.5745	Remote Similarity	NPD7521	Approved
0.5745	Remote Similarity	NPD6409	Approved
0.5745	Remote Similarity	NPD5330	Approved
0.5745	Remote Similarity	NPD7146	Approved
0.5745	Remote Similarity	NPD6684	Approved
0.5745	Remote Similarity	NPD7334	Approved
0.5714	Remote Similarity	NPD4139	Approved
0.5714	Remote Similarity	NPD388	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD8040	Discontinued
0.5714	Remote Similarity	NPD386	Approved
0.5714	Remote Similarity	NPD4768	Approved
0.5714	Remote Similarity	NPD4692	Approved
0.5702	Remote Similarity	NPD7503	Approved
0.57	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5221	Approved
0.57	Remote Similarity	NPD4697	Phase 3
0.57	Remote Similarity	NPD5222	Approved
0.5699	Remote Similarity	NPD4197	Approved
0.5676	Remote Similarity	NPD7754	Approved
0.5676	Remote Similarity	NPD7755	Approved
0.5667	Remote Similarity	NPD6683	Phase 2
0.566	Remote Similarity	NPD7990	Approved
0.566	Remote Similarity	NPD6412	Phase 2
0.566	Remote Similarity	NPD7989	Approved
0.5657	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7900	Approved
0.5652	Remote Similarity	NPD367	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