NPASS Compound

Structure

NPC471144 OpenBabel07101719132D 33 34 0 0 1 0 0 0 0 0999 V2000 2.6554 1.1823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7899 -2.3127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9035 -5.0785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8711 -3.6066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9219 -4.0592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4704 -4.4566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6611 -1.0766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2770 -0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4647 -2.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5198 0.1597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4590 0.2585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3177 -1.4947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8017 -4.7866 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1692 -4.2385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7629 -2.6323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8179 -0.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6216 -1.3960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8236 -2.7310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0057 -2.2588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7019 -0.6320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1470 -3.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2962 -3.2309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9981 -3.8628 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5036 -5.4186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3656 -5.1624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6257 -0.4356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5919 -4.2592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4926 -2.3071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6301 -3.1610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0863 -3.5938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6272 -3.6548 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 -0.3980 -3.5227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 2 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 23 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 1 0 0 0 0 9 15 2 0 0 0 0 10 11 2 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 13 24 1 0 0 0 0 14 25 2 0 0 0 0 14 31 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 10 1 6 0 0 0 16 17 1 0 0 0 0 16 32 1 0 0 0 0 17 12 1 1 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 18 31 1 6 0 0 0 19 33 1 1 0 0 0 20 26 2 0 0 0 0 20 32 1 0 0 0 0 21 27 2 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 28 2 0 0 0 0 22 33 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.18
Volume:	458.698
LogP:	1.387
LogD:	1.145
LogS:	-2.782
# Rotatable Bonds:	8
TPSA:	145.66
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	5.429
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.294
MDCK Permeability:	0.00011055384675273672
Pgp-inhibitor:	0.047
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.948
20% Bioavailability (F20%):	0.783
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.529
Plasma Protein Binding (PPB):	52.07914733886719%
Volume Distribution (VD):	0.825
Pgp-substrate:	51.06391143798828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.292
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	4.168
Half-life (T1/2):	0.533

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.613
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.137
Carcinogencity:	0.043
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.711

Download Data

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

Natural Product: NPC471144

Natural Product ID:	NPC471144
*Common Name:**	Tetraludin A
IUPAC Name:	methyl (3aS,4S,5S,6E,10E,11aR)-5-acetyloxy-4-(2,3-dihydroxy-2-methylbutanoyl)oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
Synonyms:
Standard InCHIKey:	WKVRXCYBZOWRLM-CMVWZTJQSA-N
Standard InCHI:	InChI=1S/C23H30O10/c1-11-8-7-9-15(21(27)30-6)18(31-14(4)25)19(33-22(28)23(5,29)13(3)24)17-12(2)20(26)32-16(17)10-11/h9-10,13,16-19,24,29H,2,7-8H2,1,3-6H3/b11-10+,15-9+/t13?,16-,17+,18+,19+,23?/m1/s1
SMILES:	COC(=O)/C/1=C/CC/C(=C/[C@@H]2[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C(C(O)C)(O)C)C(=C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380783
PubChem CID:	73351935
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO8415	Tetragonotheca ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO8415	Tetragonotheca ludoviciana	Species	Asteraceae	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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	21379.62	nM	PMID[529820]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[529820]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	21370.0	nM	PMID[529820]

☑ 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 NPC471144 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	225
0.1-0.2	1465
0.2-0.3	4978
0.3-0.4	8701
0.4-0.5	14574
0.5-0.6	7510
0.6-0.7	3856
0.7-0.8	1115
0.8-0.85	179
0.85-0.9	74
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC149371
0.9468	High Similarity	NPC475949
0.9457	High Similarity	NPC471142
0.9368	High Similarity	NPC47880
0.9286	High Similarity	NPC477513
0.9231	High Similarity	NPC473619
0.9149	High Similarity	NPC477921
0.9149	High Similarity	NPC17585
0.913	High Similarity	NPC473321
0.9062	High Similarity	NPC288876
0.9043	High Similarity	NPC477922
0.898	High Similarity	NPC475871
0.898	High Similarity	NPC475945
0.8969	High Similarity	NPC474339
0.8969	High Similarity	NPC164598
0.8947	High Similarity	NPC473859
0.8878	High Similarity	NPC474747
0.8878	High Similarity	NPC471148
0.8866	High Similarity	NPC477512
0.8842	High Similarity	NPC36954
0.8842	High Similarity	NPC475659
0.883	High Similarity	NPC295204
0.883	High Similarity	NPC288240
0.883	High Similarity	NPC273579
0.883	High Similarity	NPC475912
0.883	High Similarity	NPC162205
0.883	High Similarity	NPC476300
0.8817	High Similarity	NPC474232
0.8804	High Similarity	NPC473715
0.8788	High Similarity	NPC472755
0.8776	High Similarity	NPC477511
0.8776	High Similarity	NPC201718
0.8776	High Similarity	NPC474742
0.8776	High Similarity	NPC264477
0.8763	High Similarity	NPC473326
0.875	High Similarity	NPC39859
0.875	High Similarity	NPC279621
0.875	High Similarity	NPC158416
0.875	High Similarity	NPC470883
0.875	High Similarity	NPC230800
0.875	High Similarity	NPC76862
0.8723	High Similarity	NPC184463
0.8723	High Similarity	NPC30515
0.87	High Similarity	NPC474741
0.8687	High Similarity	NPC472754
0.8687	High Similarity	NPC324017
0.8687	High Similarity	NPC320019
0.8646	High Similarity	NPC270013
0.8646	High Similarity	NPC14961
0.8632	High Similarity	NPC179746
0.8632	High Similarity	NPC81419
0.8632	High Similarity	NPC212486
0.8617	High Similarity	NPC475855
0.8617	High Similarity	NPC51004
0.8602	High Similarity	NPC475819
0.8602	High Similarity	NPC202672
0.86	High Similarity	NPC4620
0.8587	High Similarity	NPC469910
0.8586	High Similarity	NPC476270
0.8586	High Similarity	NPC110443
0.8586	High Similarity	NPC472753
0.8586	High Similarity	NPC128733
0.8586	High Similarity	NPC185141
0.8586	High Similarity	NPC133907
0.8586	High Similarity	NPC15993
0.8586	High Similarity	NPC46998
0.8557	High Similarity	NPC476315
0.8557	High Similarity	NPC476009
0.8544	High Similarity	NPC38154
0.8542	High Similarity	NPC474247
0.8542	High Similarity	NPC57405
0.8542	High Similarity	NPC303942
0.8542	High Similarity	NPC474035
0.8542	High Similarity	NPC190294
0.8542	High Similarity	NPC81386
0.8526	High Similarity	NPC208886
0.8526	High Similarity	NPC12172
0.8515	High Similarity	NPC477510
0.8515	High Similarity	NPC475676
0.8515	High Similarity	NPC472756
0.8515	High Similarity	NPC220964
0.8515	High Similarity	NPC100487
0.8515	High Similarity	NPC471143
0.8511	High Similarity	NPC307411
0.8511	High Similarity	NPC474032
0.8478	Intermediate Similarity	NPC21469
0.8478	Intermediate Similarity	NPC470755
0.8469	Intermediate Similarity	NPC40812
0.8469	Intermediate Similarity	NPC471140
0.8454	Intermediate Similarity	NPC471141
0.8438	Intermediate Similarity	NPC228451
0.8438	Intermediate Similarity	NPC469645
0.8438	Intermediate Similarity	NPC469692
0.8438	Intermediate Similarity	NPC475838
0.8438	Intermediate Similarity	NPC475302
0.8438	Intermediate Similarity	NPC125674
0.8421	Intermediate Similarity	NPC474761
0.8421	Intermediate Similarity	NPC144133
0.8421	Intermediate Similarity	NPC476004
0.8421	Intermediate Similarity	NPC179394
0.8416	Intermediate Similarity	NPC475873
0.8404	Intermediate Similarity	NPC476805
0.8404	Intermediate Similarity	NPC476803
0.8384	Intermediate Similarity	NPC474213
0.837	Intermediate Similarity	NPC158756
0.8367	Intermediate Similarity	NPC306041
0.8351	Intermediate Similarity	NPC473330
0.8351	Intermediate Similarity	NPC140543
0.8351	Intermediate Similarity	NPC473316
0.8351	Intermediate Similarity	NPC471147
0.8351	Intermediate Similarity	NPC121825
0.835	Intermediate Similarity	NPC324327
0.835	Intermediate Similarity	NPC194620
0.835	Intermediate Similarity	NPC326994
0.835	Intermediate Similarity	NPC72813
0.835	Intermediate Similarity	NPC474421
0.835	Intermediate Similarity	NPC26617
0.8333	Intermediate Similarity	NPC203659
0.8316	Intermediate Similarity	NPC151770
0.8316	Intermediate Similarity	NPC166919
0.8298	Intermediate Similarity	NPC266957
0.8283	Intermediate Similarity	NPC328562
0.8283	Intermediate Similarity	NPC323421
0.8269	Intermediate Similarity	NPC55972
0.8269	Intermediate Similarity	NPC327286
0.8269	Intermediate Similarity	NPC169888
0.8269	Intermediate Similarity	NPC14862
0.8269	Intermediate Similarity	NPC474664
0.8269	Intermediate Similarity	NPC233379
0.8265	Intermediate Similarity	NPC475900
0.8261	Intermediate Similarity	NPC169575
0.8261	Intermediate Similarity	NPC116543
0.8261	Intermediate Similarity	NPC131669
0.8261	Intermediate Similarity	NPC473390
0.8261	Intermediate Similarity	NPC40746
0.8252	Intermediate Similarity	NPC9303
0.8252	Intermediate Similarity	NPC16313
0.8247	Intermediate Similarity	NPC165383
0.8235	Intermediate Similarity	NPC474165
0.8235	Intermediate Similarity	NPC69171
0.8235	Intermediate Similarity	NPC110989
0.8229	Intermediate Similarity	NPC475748
0.8211	Intermediate Similarity	NPC287089
0.82	Intermediate Similarity	NPC187268
0.82	Intermediate Similarity	NPC187761
0.82	Intermediate Similarity	NPC255592
0.82	Intermediate Similarity	NPC308567
0.82	Intermediate Similarity	NPC208233
0.82	Intermediate Similarity	NPC261377
0.82	Intermediate Similarity	NPC83895
0.8191	Intermediate Similarity	NPC305475
0.8191	Intermediate Similarity	NPC475461
0.819	Intermediate Similarity	NPC42662
0.819	Intermediate Similarity	NPC15218
0.819	Intermediate Similarity	NPC475922
0.8182	Intermediate Similarity	NPC35498
0.8182	Intermediate Similarity	NPC31645
0.8163	Intermediate Similarity	NPC476267
0.8155	Intermediate Similarity	NPC472748
0.8152	Intermediate Similarity	NPC229825
0.8144	Intermediate Similarity	NPC20713
0.8137	Intermediate Similarity	NPC225353
0.8137	Intermediate Similarity	NPC183571
0.8131	Intermediate Similarity	NPC66108
0.8125	Intermediate Similarity	NPC295312
0.8125	Intermediate Similarity	NPC92974
0.8125	Intermediate Similarity	NPC477011
0.8113	Intermediate Similarity	NPC5103
0.8113	Intermediate Similarity	NPC161816
0.8113	Intermediate Similarity	NPC115257
0.8105	Intermediate Similarity	NPC231889
0.8105	Intermediate Similarity	NPC186148
0.81	Intermediate Similarity	NPC471462
0.8085	Intermediate Similarity	NPC255307
0.8077	Intermediate Similarity	NPC243998
0.8077	Intermediate Similarity	NPC472749
0.8077	Intermediate Similarity	NPC472751
0.8077	Intermediate Similarity	NPC475802
0.8077	Intermediate Similarity	NPC223450
0.8065	Intermediate Similarity	NPC59097
0.8058	Intermediate Similarity	NPC472750
0.8058	Intermediate Similarity	NPC472747
0.8043	Intermediate Similarity	NPC24417
0.8041	Intermediate Similarity	NPC316228
0.8039	Intermediate Similarity	NPC473332
0.8022	Intermediate Similarity	NPC167881
0.8022	Intermediate Similarity	NPC98557
0.8021	Intermediate Similarity	NPC177629
0.8021	Intermediate Similarity	NPC58219
0.8021	Intermediate Similarity	NPC280621
0.8021	Intermediate Similarity	NPC233551
0.8021	Intermediate Similarity	NPC20339
0.8021	Intermediate Similarity	NPC21208
0.8021	Intermediate Similarity	NPC89001
0.8021	Intermediate Similarity	NPC40376
0.8021	Intermediate Similarity	NPC153805
0.8021	Intermediate Similarity	NPC48338
0.802	Intermediate Similarity	NPC161855
0.8	Intermediate Similarity	NPC471146
0.8	Intermediate Similarity	NPC150755

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 NPC471144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	2101
0.2-0.3	3651
0.3-0.4	2043
0.4-0.5	765
0.5-0.6	270
0.6-0.7	105
0.7-0.8	7
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.835	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD46	Approved
0.7857	Intermediate Similarity	NPD6698	Approved
0.7778	Intermediate Similarity	NPD7983	Approved
0.7615	Intermediate Similarity	NPD6371	Approved
0.7549	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7838	Discovery
0.7387	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4225	Approved
0.7117	Intermediate Similarity	NPD6686	Approved
0.7115	Intermediate Similarity	NPD5282	Discontinued
0.7009	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD8513	Phase 3
0.6975	Remote Similarity	NPD8517	Approved
0.6975	Remote Similarity	NPD8515	Approved
0.6975	Remote Similarity	NPD8516	Approved
0.6893	Remote Similarity	NPD1695	Approved
0.6891	Remote Similarity	NPD6319	Approved
0.6875	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5778	Approved
0.6857	Remote Similarity	NPD5779	Approved
0.6827	Remote Similarity	NPD5785	Approved
0.6727	Remote Similarity	NPD5344	Discontinued
0.6724	Remote Similarity	NPD6053	Discontinued
0.6721	Remote Similarity	NPD7642	Approved
0.6694	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7115	Discovery
0.6638	Remote Similarity	NPD2204	Approved
0.6634	Remote Similarity	NPD6110	Phase 1
0.6602	Remote Similarity	NPD4249	Approved
0.6602	Remote Similarity	NPD5786	Approved
0.6587	Remote Similarity	NPD7319	Approved
0.6585	Remote Similarity	NPD7829	Approved
0.6585	Remote Similarity	NPD7830	Approved
0.6538	Remote Similarity	NPD4250	Approved
0.6538	Remote Similarity	NPD4251	Approved
0.6532	Remote Similarity	NPD7492	Approved
0.6525	Remote Similarity	NPD4632	Approved
0.648	Remote Similarity	NPD8451	Approved
0.648	Remote Similarity	NPD6616	Approved
0.648	Remote Similarity	NPD7507	Approved
0.6475	Remote Similarity	NPD6054	Approved
0.6471	Remote Similarity	NPD7154	Phase 3
0.6466	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8328	Phase 3
0.6441	Remote Similarity	NPD8297	Approved
0.6436	Remote Similarity	NPD5369	Approved
0.6429	Remote Similarity	NPD7078	Approved
0.6429	Remote Similarity	NPD8448	Approved
0.6423	Remote Similarity	NPD6016	Approved
0.6423	Remote Similarity	NPD6015	Approved
0.6415	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6101	Approved
0.641	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7736	Approved
0.6373	Remote Similarity	NPD4270	Approved
0.6373	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4269	Approved
0.6373	Remote Similarity	NPD6435	Approved
0.6371	Remote Similarity	NPD8080	Discontinued
0.6371	Remote Similarity	NPD5988	Approved
0.6371	Remote Similarity	NPD6370	Approved
0.6357	Remote Similarity	NPD7260	Phase 2
0.6356	Remote Similarity	NPD6649	Approved
0.6356	Remote Similarity	NPD6650	Approved
0.6341	Remote Similarity	NPD6059	Approved
0.6339	Remote Similarity	NPD6648	Approved
0.6337	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4252	Approved
0.6325	Remote Similarity	NPD6373	Approved
0.6325	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD7641	Discontinued
0.6299	Remote Similarity	NPD8293	Discontinued
0.6296	Remote Similarity	NPD6411	Approved
0.6293	Remote Similarity	NPD5697	Approved
0.629	Remote Similarity	NPD8444	Approved
0.6279	Remote Similarity	NPD8391	Approved
0.6279	Remote Similarity	NPD8390	Approved
0.6279	Remote Similarity	NPD8392	Approved
0.6271	Remote Similarity	NPD4634	Approved
0.627	Remote Similarity	NPD8299	Approved
0.627	Remote Similarity	NPD8342	Approved
0.627	Remote Similarity	NPD8341	Approved
0.627	Remote Similarity	NPD8340	Approved
0.625	Remote Similarity	NPD7638	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.623	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6009	Approved
0.622	Remote Similarity	NPD8273	Phase 1
0.6214	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5209	Approved
0.6207	Remote Similarity	NPD7128	Approved
0.6207	Remote Similarity	NPD6675	Approved
0.6207	Remote Similarity	NPD5739	Approved
0.6207	Remote Similarity	NPD6402	Approved
0.6195	Remote Similarity	NPD7639	Approved
0.6195	Remote Similarity	NPD7640	Approved
0.619	Remote Similarity	NPD1694	Approved
0.619	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6013	Approved
0.6186	Remote Similarity	NPD6014	Approved
0.6186	Remote Similarity	NPD6012	Approved
0.6183	Remote Similarity	NPD6845	Suspended
0.6176	Remote Similarity	NPD4821	Approved
0.6176	Remote Similarity	NPD5368	Approved
0.6176	Remote Similarity	NPD4822	Approved
0.6176	Remote Similarity	NPD4820	Approved
0.6176	Remote Similarity	NPD4819	Approved
0.6167	Remote Similarity	NPD6882	Approved
0.616	Remote Similarity	NPD6921	Approved
0.616	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.616	Remote Similarity	NPD5983	Phase 2
0.6154	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5701	Approved
0.6139	Remote Similarity	NPD4271	Approved
0.6139	Remote Similarity	NPD4268	Approved
0.6134	Remote Similarity	NPD7102	Approved
0.6134	Remote Similarity	NPD7290	Approved
0.6134	Remote Similarity	NPD6883	Approved
0.6102	Remote Similarity	NPD6011	Approved
0.6102	Remote Similarity	NPD7320	Approved
0.6098	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8130	Phase 1
0.6083	Remote Similarity	NPD6617	Approved
0.6083	Remote Similarity	NPD6847	Approved
0.6083	Remote Similarity	NPD6869	Approved
0.6068	Remote Similarity	NPD6008	Approved
0.6063	Remote Similarity	NPD7604	Phase 2
0.6045	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4756	Discovery
0.6018	Remote Similarity	NPD6084	Phase 2
0.6018	Remote Similarity	NPD6083	Phase 2
0.6017	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD6421	Discontinued
0.5982	Remote Similarity	NPD5695	Phase 3
0.597	Remote Similarity	NPD8415	Approved
0.5969	Remote Similarity	NPD6336	Discontinued
0.5968	Remote Similarity	NPD7500	Approved
0.5965	Remote Similarity	NPD5696	Approved
0.5963	Remote Similarity	NPD5370	Suspended
0.5957	Remote Similarity	NPD3197	Phase 1
0.5948	Remote Similarity	NPD5211	Phase 2
0.5938	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7327	Approved
0.592	Remote Similarity	NPD7328	Approved
0.5913	Remote Similarity	NPD5286	Approved
0.5913	Remote Similarity	NPD4696	Approved
0.5913	Remote Similarity	NPD5285	Approved
0.5906	Remote Similarity	NPD7503	Approved
0.5906	Remote Similarity	NPD8269	Approved
0.5906	Remote Similarity	NPD8268	Approved
0.5906	Remote Similarity	NPD8033	Approved
0.5906	Remote Similarity	NPD8266	Approved
0.5906	Remote Similarity	NPD8267	Approved
0.5895	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6274	Approved
0.5878	Remote Similarity	NPD6033	Approved
0.5877	Remote Similarity	NPD4755	Approved
0.5873	Remote Similarity	NPD7516	Approved
0.5856	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD8133	Approved
0.5847	Remote Similarity	NPD5141	Approved
0.5847	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8377	Approved
0.5827	Remote Similarity	NPD8294	Approved
0.5825	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD5224	Approved
0.5812	Remote Similarity	NPD5225	Approved
0.5812	Remote Similarity	NPD5226	Approved
0.5812	Remote Similarity	NPD4633	Approved
0.5804	Remote Similarity	NPD6399	Phase 3
0.5804	Remote Similarity	NPD6190	Approved
0.5794	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5956	Approved
0.5789	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD8296	Approved
0.5781	Remote Similarity	NPD8380	Approved
0.5781	Remote Similarity	NPD8335	Approved
0.5781	Remote Similarity	NPD8379	Approved
0.5781	Remote Similarity	NPD8378	Approved
0.5776	Remote Similarity	NPD4700	Approved
0.5763	Remote Similarity	NPD5175	Approved
0.5763	Remote Similarity	NPD5174	Approved
0.5748	Remote Similarity	NPD7100	Approved
0.5748	Remote Similarity	NPD7101	Approved
0.5738	Remote Similarity	NPD2067	Discontinued
0.5726	Remote Similarity	NPD5223	Approved
0.5714	Remote Similarity	NPD6317	Approved
0.5714	Remote Similarity	NPD73	Approved
0.5714	Remote Similarity	NPD5693	Phase 1

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