NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1196.63
Volume:	1264.509
LogP:	0.634
LogD:	1.214
LogS:	-4.644
# Rotatable Bonds:	6
TPSA:	313.82
# H-Bond Aceptor:	18
# H-Bond Donor:	12
# Rings:	3
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.095
Synthetic Accessibility Score:	7.217
Fsp3:	0.441
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.459
MDCK Permeability:	2.4755707272561267e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	90.93102264404297%
Volume Distribution (VD):	0.133
Pgp-substrate:	5.8273162841796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.635
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.249
CYP2C19-substrate:	0.385
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.977
CYP3A4-inhibitor:	0.496
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	0.79
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.001
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.961
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.342

Download Data

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

Natural Product: NPC476684

Natural Product ID:	NPC476684
*Common Name:**	(8E,16E,18E,20E,22E,24E,38E,46E,48E,50E,52E,54E)-6,10,12,14,28,36,40,42,44,58-decahydroxy-4,34-bis(2-hydroxypropyl)-30,60-dimethoxy-16,46-dimethyl-3,33-dioxatricyclo[54.4.0.026,31]hexaconta-1(56),8,16,18,20,22,24,26(31),27,29,38,46,48,50,52,54,57,59-octadecaene-2,32-dione
IUPAC Name:	(8E,16E,18E,20E,22E,24E,38E,46E,48E,50E,52E,54E)-6,10,12,14,28,36,40,42,44,58-decahydroxy-4,34-bis(2-hydroxypropyl)-30,60-dimethoxy-16,46-dimethyl-3,33-dioxatricyclo[54.4.0.026,31]hexaconta-1(56),8,16,18,20,22,24,26(31),27,29,38,46,48,50,52,54,57,59-octadecaene-2,32-dione
Synonyms:
Standard InCHIKey:	NPLSGIXDWVETBM-TYRQAPOMSA-N
Standard InCHI:	InChI=1S/C68H92O18/c1-45-23-17-13-9-7-11-15-19-25-49-35-57(77)43-63(83-5)65(49)67(81)86-62(34-48(4)70)42-54(74)30-22-28-52(72)38-60(80)40-56(76)32-46(2)24-18-14-10-8-12-16-20-26-50-36-58(78)44-64(84-6)66(50)68(82)85-61(33-47(3)69)41-53(73)29-21-27-51(71)37-59(79)39-55(75)31-45/h7-28,35-36,43-44,47-48,51-56,59-62,69-80H,29-34,37-42H2,1-6H3/b9-7+,10-8+,15-11+,16-12+,17-13+,18-14+,25-19+,26-20+,27-21+,28-22+,45-23+,46-24+
SMILES:	C/C/1=C\C=C\C=C\C=C\C=C\C2=C(C(=O)OC(CC(C/C=C/C(CC(CC(C/C(=C/C=C/C=C/C=C/C=C/C3=C(C(=O)OC(CC(C/C=C/C(CC(CC(C1)O)O)O)O)CC(O)C)C(=CC(=C3)O)OC)/C)O)O)O)O)CC(O)C)C(=CC(=C2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122177656
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO17376.1	Bacillus amyloliquefaciens subsp. plantarum AP183	Under-species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25756620]

☑ 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	6
MIC	6
Others	5

Activity Type	# Activity
Organism	17

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	<	0.02	ug/ml	PMID[25756620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	1.2	ug/ml	PMID[25756620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.2	ug/ml	PMID[25756620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	0.04	ug/ml	PMID[25756620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	2.5	ug/ml	PMID[25756620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.6	ug/ml	PMID[25756620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	0.6	ug/ml	PMID[25756620]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	IC50	=	0.2	ug/ml	PMID[25756620]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	=	0.6	ug/ml	PMID[25756620]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MBC	=	2.5	ug/ml	PMID[25756620]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	=	0.1	ug/ml	PMID[25756620]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	0.6	ug/ml	PMID[25756620]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IC50	=	0.2	ug/ml	PMID[25756620]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	0.6	ug/ml	PMID[25756620]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MBC	=	1.2	ug/ml	PMID[25756620]

☑ 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 NPC476684 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	337
0.1-0.2	1370
0.2-0.3	3332
0.3-0.4	7645
0.4-0.5	10951
0.5-0.6	3693
0.6-0.7	5602
0.7-0.8	7226
0.8-0.85	2080
0.85-0.9	404
0.9-0.95	56
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9521	High Similarity	NPC475460
0.9507	High Similarity	NPC474385
0.9384	High Similarity	NPC221352
0.9375	High Similarity	NPC280404
0.9375	High Similarity	NPC86373
0.9375	High Similarity	NPC277426
0.9375	High Similarity	NPC210425
0.9371	High Similarity	NPC250755
0.9306	High Similarity	NPC51106
0.9306	High Similarity	NPC469542
0.9301	High Similarity	NPC1704
0.9301	High Similarity	NPC475730
0.9301	High Similarity	NPC158634
0.9301	High Similarity	NPC67650
0.9247	High Similarity	NPC237208
0.9241	High Similarity	NPC66404
0.9241	High Similarity	NPC95123
0.9236	High Similarity	NPC469579
0.9195	High Similarity	NPC70016
0.9195	High Similarity	NPC215921
0.9184	High Similarity	NPC210320
0.9184	High Similarity	NPC472036
0.9184	High Similarity	NPC125801
0.9178	High Similarity	NPC29577
0.9178	High Similarity	NPC134621
0.9178	High Similarity	NPC472034
0.9172	High Similarity	NPC472006
0.9161	High Similarity	NPC32360
0.9155	High Similarity	NPC135837
0.9128	High Similarity	NPC309979
0.9128	High Similarity	NPC469670
0.9128	High Similarity	NPC60413
0.9128	High Similarity	NPC307780
0.9128	High Similarity	NPC469619
0.9122	High Similarity	NPC73411
0.9122	High Similarity	NPC471641
0.9122	High Similarity	NPC215711
0.9122	High Similarity	NPC240622
0.9122	High Similarity	NPC240253
0.9122	High Similarity	NPC471642
0.9116	High Similarity	NPC472033
0.9116	High Similarity	NPC225173
0.9116	High Similarity	NPC163846
0.9103	High Similarity	NPC105648
0.9097	High Similarity	NPC158472
0.9091	High Similarity	NPC478200
0.9091	High Similarity	NPC212693
0.9091	High Similarity	NPC94248
0.9091	High Similarity	NPC33144
0.9067	High Similarity	NPC200773
0.9067	High Similarity	NPC240768
0.906	High Similarity	NPC6923
0.9054	High Similarity	NPC12305
0.9034	High Similarity	NPC220106
0.9028	High Similarity	NPC268052
0.9021	High Similarity	NPC71256
0.9021	High Similarity	NPC70380
0.9014	High Similarity	NPC182496
0.9014	High Similarity	NPC180905
0.9007	High Similarity	NPC273483
0.8986	High Similarity	NPC107625
0.898	High Similarity	NPC470932
0.8973	High Similarity	NPC49108
0.8966	High Similarity	NPC155205
0.8958	High Similarity	NPC472602
0.8958	High Similarity	NPC191835
0.8951	High Similarity	NPC235115
0.894	High Similarity	NPC133856
0.8933	High Similarity	NPC270160
0.8933	High Similarity	NPC291049
0.8933	High Similarity	NPC237440
0.8933	High Similarity	NPC233267
0.8919	High Similarity	NPC312789
0.8917	High Similarity	NPC7752
0.8912	High Similarity	NPC478202
0.8904	High Similarity	NPC478217
0.8904	High Similarity	NPC472604
0.8904	High Similarity	NPC472035
0.8904	High Similarity	NPC90411
0.8904	High Similarity	NPC53649
0.8904	High Similarity	NPC472605
0.8904	High Similarity	NPC313123
0.8904	High Similarity	NPC478201
0.8897	High Similarity	NPC139634
0.8897	High Similarity	NPC105456
0.8889	High Similarity	NPC89625
0.8889	High Similarity	NPC473391
0.8889	High Similarity	NPC99381
0.8889	High Similarity	NPC472364
0.8889	High Similarity	NPC472367
0.8889	High Similarity	NPC476333
0.8889	High Similarity	NPC149618
0.8882	High Similarity	NPC167903
0.8882	High Similarity	NPC474843
0.8874	High Similarity	NPC295036
0.8873	High Similarity	NPC153783
0.8867	High Similarity	NPC172329
0.8867	High Similarity	NPC105415
0.8867	High Similarity	NPC2569
0.8859	High Similarity	NPC267509
0.8859	High Similarity	NPC473023
0.8851	High Similarity	NPC42540
0.8851	High Similarity	NPC151607
0.8836	High Similarity	NPC472600
0.8836	High Similarity	NPC472601
0.8831	High Similarity	NPC227062
0.8811	High Similarity	NPC175943
0.8808	High Similarity	NPC4423
0.8808	High Similarity	NPC77325
0.8805	High Similarity	NPC249977
0.8792	High Similarity	NPC32470
0.8792	High Similarity	NPC257558
0.8792	High Similarity	NPC83272
0.8784	High Similarity	NPC471731
0.8784	High Similarity	NPC159721
0.8784	High Similarity	NPC310340
0.8782	High Similarity	NPC472055
0.8776	High Similarity	NPC244923
0.8776	High Similarity	NPC472603
0.8774	High Similarity	NPC257309
0.8767	High Similarity	NPC247409
0.8767	High Similarity	NPC472368
0.8766	High Similarity	NPC16082
0.8766	High Similarity	NPC82592
0.8759	High Similarity	NPC261292
0.8759	High Similarity	NPC301915
0.8759	High Similarity	NPC194579
0.8758	High Similarity	NPC478224
0.875	High Similarity	NPC142027
0.875	High Similarity	NPC119929
0.875	High Similarity	NPC470107
0.8742	High Similarity	NPC153417
0.8742	High Similarity	NPC106328
0.8742	High Similarity	NPC35150
0.8742	High Similarity	NPC37139
0.8733	High Similarity	NPC138978
0.8732	High Similarity	NPC219892
0.8732	High Similarity	NPC189823
0.8725	High Similarity	NPC478203
0.8725	High Similarity	NPC126882
0.8725	High Similarity	NPC210966
0.8718	High Similarity	NPC474373
0.8718	High Similarity	NPC470339
0.8716	High Similarity	NPC471640
0.8716	High Similarity	NPC471733
0.8716	High Similarity	NPC96692
0.8716	High Similarity	NPC470087
0.8716	High Similarity	NPC321980
0.8716	High Similarity	NPC471644
0.8716	High Similarity	NPC476508
0.871	High Similarity	NPC146211
0.871	High Similarity	NPC54928
0.8707	High Similarity	NPC165172
0.8707	High Similarity	NPC472366
0.8707	High Similarity	NPC470211
0.8701	High Similarity	NPC472799
0.8701	High Similarity	NPC210942
0.8701	High Similarity	NPC281477
0.8701	High Similarity	NPC169990
0.8699	High Similarity	NPC475974
0.8699	High Similarity	NPC188879
0.8699	High Similarity	NPC9121
0.8699	High Similarity	NPC177307
0.8693	High Similarity	NPC470569
0.8693	High Similarity	NPC204350
0.8693	High Similarity	NPC72958
0.8693	High Similarity	NPC91809
0.8693	High Similarity	NPC232645
0.8693	High Similarity	NPC478148
0.8693	High Similarity	NPC227166
0.8681	High Similarity	NPC28753
0.8681	High Similarity	NPC18877
0.8681	High Similarity	NPC188646
0.8681	High Similarity	NPC56031
0.8681	High Similarity	NPC204960
0.8681	High Similarity	NPC337373
0.8681	High Similarity	NPC192304
0.8681	High Similarity	NPC175098
0.8681	High Similarity	NPC294593
0.8681	High Similarity	NPC144051
0.8681	High Similarity	NPC20560
0.8681	High Similarity	NPC82225
0.8681	High Similarity	NPC242294
0.8681	High Similarity	NPC159623
0.8681	High Similarity	NPC312318
0.8681	High Similarity	NPC263670
0.8681	High Similarity	NPC139813
0.8681	High Similarity	NPC472365
0.8675	High Similarity	NPC8817
0.8675	High Similarity	NPC259632
0.8675	High Similarity	NPC14098
0.8671	High Similarity	NPC470160
0.8667	High Similarity	NPC473692
0.8662	High Similarity	NPC299436
0.8662	High Similarity	NPC12694
0.8662	High Similarity	NPC321399
0.8662	High Similarity	NPC143050
0.8658	High Similarity	NPC84266
0.8658	High Similarity	NPC471639
0.8658	High Similarity	NPC471643

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 NPC476684 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	911
0.2-0.3	1649
0.3-0.4	2538
0.4-0.5	1929
0.5-0.6	1151
0.6-0.7	471
0.7-0.8	172
0.8-0.85	35
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9073	High Similarity	NPD7819	Suspended
0.9028	High Similarity	NPD970	Clinical (unspecified phase)
0.8543	High Similarity	NPD2533	Approved
0.8543	High Similarity	NPD2534	Approved
0.8543	High Similarity	NPD2532	Approved
0.8535	High Similarity	NPD7075	Discontinued
0.8526	High Similarity	NPD8443	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD6232	Discontinued
0.8435	Intermediate Similarity	NPD1510	Phase 2
0.8414	Intermediate Similarity	NPD1240	Approved
0.8403	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD7473	Discontinued
0.8389	Intermediate Similarity	NPD1549	Phase 2
0.8387	Intermediate Similarity	NPD4380	Phase 2
0.8355	Intermediate Similarity	NPD6799	Approved
0.8354	Intermediate Similarity	NPD7768	Phase 2
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7411	Suspended
0.8301	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1607	Approved
0.8291	Intermediate Similarity	NPD3817	Phase 2
0.828	Intermediate Similarity	NPD1934	Approved
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8278	Intermediate Similarity	NPD3750	Approved
0.8261	Intermediate Similarity	NPD6959	Discontinued
0.8255	Intermediate Similarity	NPD2935	Discontinued
0.8255	Intermediate Similarity	NPD2796	Approved
0.8255	Intermediate Similarity	NPD1551	Phase 2
0.8242	Intermediate Similarity	NPD7472	Approved
0.8221	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7808	Phase 3
0.8187	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7054	Approved
0.8158	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8144	Intermediate Similarity	NPD7251	Discontinued
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8125	Intermediate Similarity	NPD3882	Suspended
0.8125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1511	Approved
0.8113	Intermediate Similarity	NPD2801	Approved
0.811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6166	Phase 2
0.811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD6797	Phase 2
0.8077	Intermediate Similarity	NPD5403	Approved
0.8075	Intermediate Similarity	NPD3749	Approved
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5402	Approved
0.8039	Intermediate Similarity	NPD4628	Phase 3
0.8014	Intermediate Similarity	NPD6832	Phase 2
0.8013	Intermediate Similarity	NPD1512	Approved
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD5401	Approved
0.7947	Intermediate Similarity	NPD3748	Approved
0.7931	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5710	Approved
0.7879	Intermediate Similarity	NPD5711	Approved
0.787	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3226	Approved
0.7857	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6559	Discontinued
0.7815	Intermediate Similarity	NPD6651	Approved
0.7808	Intermediate Similarity	NPD1203	Approved
0.7778	Intermediate Similarity	NPD1465	Phase 2
0.7765	Intermediate Similarity	NPD5953	Discontinued
0.7748	Intermediate Similarity	NPD230	Phase 1
0.7733	Intermediate Similarity	NPD8312	Approved
0.7733	Intermediate Similarity	NPD8313	Approved
0.7722	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD37	Approved
0.7712	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2799	Discontinued
0.7712	Intermediate Similarity	NPD7033	Discontinued
0.7711	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4966	Approved
0.7683	Intermediate Similarity	NPD4965	Approved
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7662	Intermediate Similarity	NPD6100	Approved
0.7662	Intermediate Similarity	NPD6099	Approved
0.7658	Intermediate Similarity	NPD7390	Discontinued
0.7651	Intermediate Similarity	NPD5494	Approved
0.7647	Intermediate Similarity	NPD7286	Phase 2
0.764	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2800	Approved
0.7628	Intermediate Similarity	NPD1243	Approved
0.7625	Intermediate Similarity	NPD920	Approved
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD9545	Approved
0.7614	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.7603	Intermediate Similarity	NPD1608	Approved
0.7603	Intermediate Similarity	NPD9717	Approved
0.7595	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6234	Discontinued
0.7581	Intermediate Similarity	NPD8151	Discontinued
0.7566	Intermediate Similarity	NPD943	Approved
0.756	Intermediate Similarity	NPD7229	Phase 3
0.755	Intermediate Similarity	NPD3764	Approved
0.7548	Intermediate Similarity	NPD5406	Approved
0.7548	Intermediate Similarity	NPD5405	Approved
0.7548	Intermediate Similarity	NPD5404	Approved
0.7548	Intermediate Similarity	NPD5408	Approved
0.7534	Intermediate Similarity	NPD422	Phase 1
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD919	Approved
0.7485	Intermediate Similarity	NPD7228	Approved
0.7483	Intermediate Similarity	NPD9493	Approved
0.7471	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6273	Approved
0.745	Intermediate Similarity	NPD2797	Approved
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD411	Approved
0.7434	Intermediate Similarity	NPD3268	Approved
0.7421	Intermediate Similarity	NPD6190	Approved
0.7417	Intermediate Similarity	NPD4908	Phase 1
0.7414	Intermediate Similarity	NPD7685	Pre-registration
0.7412	Intermediate Similarity	NPD3926	Phase 2
0.741	Intermediate Similarity	NPD4288	Approved
0.7405	Intermediate Similarity	NPD7435	Discontinued
0.7403	Intermediate Similarity	NPD6355	Discontinued
0.7403	Intermediate Similarity	NPD447	Suspended
0.74	Intermediate Similarity	NPD2798	Approved
0.7397	Intermediate Similarity	NPD17	Approved
0.7384	Intermediate Similarity	NPD3751	Discontinued
0.7383	Intermediate Similarity	NPD1283	Approved
0.7372	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3027	Phase 3
0.7358	Intermediate Similarity	NPD7003	Approved
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7349	Intermediate Similarity	NPD8455	Phase 2
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4060	Phase 1
0.7333	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2438	Suspended
0.732	Intermediate Similarity	NPD2313	Discontinued
0.732	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7458	Discontinued
0.7316	Intermediate Similarity	NPD7783	Phase 2
0.7316	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2309	Approved
0.7312	Intermediate Similarity	NPD7697	Approved
0.7312	Intermediate Similarity	NPD7698	Approved
0.7312	Intermediate Similarity	NPD7696	Phase 3
0.7297	Intermediate Similarity	NPD1201	Approved
0.7297	Intermediate Similarity	NPD1610	Phase 2
0.7296	Intermediate Similarity	NPD2654	Approved
0.729	Intermediate Similarity	NPD5124	Phase 1
0.729	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7267	Intermediate Similarity	NPD3225	Approved
0.7267	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7874	Approved
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.726	Intermediate Similarity	NPD1548	Phase 1
0.7255	Intermediate Similarity	NPD4625	Phase 3
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD2979	Phase 3
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1164	Approved
0.7219	Intermediate Similarity	NPD1470	Approved
0.7216	Intermediate Similarity	NPD7240	Approved
0.7215	Intermediate Similarity	NPD4476	Approved
0.7215	Intermediate Similarity	NPD4477	Approved
0.7211	Intermediate Similarity	NPD5691	Approved
0.7209	Intermediate Similarity	NPD5242	Approved
0.7208	Intermediate Similarity	NPD6798	Discontinued
0.7202	Intermediate Similarity	NPD5353	Approved
0.7184	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7177	Discontinued
0.7181	Intermediate Similarity	NPD1281	Approved
0.7181	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1933	Approved
0.7171	Intermediate Similarity	NPD1019	Discontinued
0.7171	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1778	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