NPASS Compound

Structure

NPC128475 OpenBabel07101719512D 34 39 0 0 1 0 0 0 0 0999 V2000 0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0390 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8477 0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 1.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1730 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3070 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9051 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9051 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3070 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0390 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3070 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4410 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7711 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7711 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1730 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9021 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1730 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4899 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0390 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4410 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6371 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6371 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0390 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.6910 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 2 24 1 0 0 0 0 3 24 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 9 15 1 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 12 19 1 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 26 1 0 0 0 0 14 1 1 6 0 0 0 14 24 1 0 0 0 0 15 25 1 1 0 0 0 16 8 1 6 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 26 1 1 0 0 0 18 19 1 0 0 0 0 18 29 1 6 0 0 0 19 30 1 6 0 0 0 20 22 1 0 0 0 0 20 31 1 1 0 0 0 21 10 1 1 0 0 0 21 23 1 0 0 0 0 21 33 1 0 0 0 0 22 25 1 1 0 0 0 23 26 1 1 0 0 0 23 27 1 0 0 0 0 24 34 1 0 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 27 28 1 1 0 0 0 27 32 1 0 0 0 0 28 11 1 1 0 0 0 28 33 1 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.33
Volume:	494.247
LogP:	4.141
LogD:	3.882
LogS:	-4.476
# Rotatable Bonds:	0
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	5.973
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.108
MDCK Permeability:	3.810920679825358e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.188

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	59.1114387512207%
Volume Distribution (VD):	0.823
Pgp-substrate:	22.890562057495117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.736
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	12.43
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.358
Drug-inuced Liver Injury (DILI):	0.131
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.939
Carcinogencity:	0.686
Eye Corrosion:	0.387
Eye Irritation:	0.057
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC128475

Natural Product ID:	NPC128475
*Common Name:**	BCZIXMFNQQMCFI-LMGJWPTFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BCZIXMFNQQMCFI-LMGJWPTFSA-N
Standard InCHI:	InChI=1S/C28H46O6/c1-14-11-28(34-24(14,2)3)27(6,32)23-21(33-28)10-17-16-8-7-15-9-18(29)19(30)12-25(15,4)22(16)20(31)13-26(17,23)5/h14-23,29-32H,7-13H2,1-6H3/t14-,15-,16-,17-,18-,19+,20-,21-,22+,23-,25-,26-,27+,28-/m0/s1
SMILES:	C[C@H]1C[C@@]2([C@@](C)([C@H]3[C@H](C[C@H]4[C@@H]5CC[C@H]6C[C@@H]([C@@H](C[C@]6(C)[C@H]5[C@H](C[C@]34C)O)O)O)O2)O)OC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457151
PubChem CID:	20833541
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001702] Furospirostanes 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
NPO19653	Isis hippuris	Species	Isididae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141096]
NPO19653	Isis hippuris	Species	Isididae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974612]
NPO19653	Isis hippuris	Species	Isididae	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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.62	ug.mL-1	PMID[454578]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.59	ug.mL-1	PMID[454578]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	0.75	ug.mL-1	PMID[454578]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.77	ug.mL-1	PMID[454578]
NPT22886	SINGLE PROTEIN	Eukaryotic initiation factor 4A-I	Mus musculus	IC50	=	19000.0	nM	PMID[454579]

☑ 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 NPC128475 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	497
0.1-0.2	4641
0.2-0.3	13408
0.3-0.4	10977
0.4-0.5	5559
0.5-0.6	4565
0.6-0.7	2167
0.7-0.8	669
0.8-0.85	173
0.85-0.9	31
0.9-0.95	3
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC161928
0.9878	High Similarity	NPC210658
0.9535	High Similarity	NPC182740
0.9535	High Similarity	NPC211845
0.9535	High Similarity	NPC256104
0.9535	High Similarity	NPC122083
0.9268	High Similarity	NPC470611
0.9186	High Similarity	NPC20822
0.9167	High Similarity	NPC273290
0.9167	High Similarity	NPC232044
0.9048	High Similarity	NPC227260
0.8989	High Similarity	NPC3538
0.8989	High Similarity	NPC113500
0.8989	High Similarity	NPC477224
0.8977	High Similarity	NPC5632
0.8977	High Similarity	NPC149966
0.8966	High Similarity	NPC228059
0.8929	High Similarity	NPC470070
0.8889	High Similarity	NPC21897
0.8876	High Similarity	NPC167644
0.8876	High Similarity	NPC311246
0.8864	High Similarity	NPC473542
0.8837	High Similarity	NPC471240
0.8817	High Similarity	NPC477225
0.881	High Similarity	NPC475388
0.881	High Similarity	NPC296734
0.8804	High Similarity	NPC292775
0.8778	High Similarity	NPC175
0.8778	High Similarity	NPC30687
0.8778	High Similarity	NPC45959
0.8778	High Similarity	NPC252253
0.8764	High Similarity	NPC59006
0.8764	High Similarity	NPC293609
0.875	High Similarity	NPC82955
0.875	High Similarity	NPC473472
0.8721	High Similarity	NPC290612
0.8696	High Similarity	NPC477223
0.8696	High Similarity	NPC477222
0.8681	High Similarity	NPC473065
0.8681	High Similarity	NPC473067
0.8681	High Similarity	NPC473064
0.8675	High Similarity	NPC81074
0.8675	High Similarity	NPC477282
0.8667	High Similarity	NPC88962
0.8667	High Similarity	NPC144790
0.8667	High Similarity	NPC277774
0.8667	High Similarity	NPC149400
0.8659	High Similarity	NPC11907
0.8659	High Similarity	NPC474574
0.8659	High Similarity	NPC64081
0.8659	High Similarity	NPC133596
0.8652	High Similarity	NPC279329
0.8652	High Similarity	NPC223143
0.8636	High Similarity	NPC281004
0.8602	High Similarity	NPC473638
0.8587	High Similarity	NPC139271
0.8587	High Similarity	NPC121453
0.8587	High Similarity	NPC142264
0.8587	High Similarity	NPC304011
0.8587	High Similarity	NPC156377
0.8587	High Similarity	NPC476510
0.8571	High Similarity	NPC179859
0.8571	High Similarity	NPC7479
0.8571	High Similarity	NPC473851
0.8571	High Similarity	NPC174024
0.8571	High Similarity	NPC257296
0.8571	High Similarity	NPC475436
0.8571	High Similarity	NPC473774
0.8571	High Similarity	NPC291547
0.8571	High Similarity	NPC222731
0.8571	High Similarity	NPC253268
0.8571	High Similarity	NPC131693
0.8571	High Similarity	NPC312678
0.8571	High Similarity	NPC24960
0.8571	High Similarity	NPC294686
0.8571	High Similarity	NPC248944
0.8556	High Similarity	NPC36372
0.8556	High Similarity	NPC229801
0.8556	High Similarity	NPC307167
0.8556	High Similarity	NPC210759
0.8542	High Similarity	NPC100078
0.8539	High Similarity	NPC102725
0.8537	High Similarity	NPC163597
0.8523	High Similarity	NPC140446
0.8523	High Similarity	NPC472396
0.8523	High Similarity	NPC43912
0.8506	High Similarity	NPC266651
0.8495	Intermediate Similarity	NPC233649
0.8495	Intermediate Similarity	NPC470028
0.8478	Intermediate Similarity	NPC474399
0.8478	Intermediate Similarity	NPC92196
0.8462	Intermediate Similarity	NPC250393
0.8462	Intermediate Similarity	NPC234352
0.8462	Intermediate Similarity	NPC476669
0.8462	Intermediate Similarity	NPC477547
0.8462	Intermediate Similarity	NPC249204
0.8462	Intermediate Similarity	NPC477451
0.8462	Intermediate Similarity	NPC48339
0.8462	Intermediate Similarity	NPC177834
0.8462	Intermediate Similarity	NPC325828
0.8462	Intermediate Similarity	NPC297348
0.8462	Intermediate Similarity	NPC141769
0.8454	Intermediate Similarity	NPC166079
0.8444	Intermediate Similarity	NPC65550
0.8434	Intermediate Similarity	NPC128951
0.8434	Intermediate Similarity	NPC477227
0.8434	Intermediate Similarity	NPC105208
0.8434	Intermediate Similarity	NPC302578
0.8434	Intermediate Similarity	NPC192046
0.8415	Intermediate Similarity	NPC91387
0.8415	Intermediate Similarity	NPC270306
0.8415	Intermediate Similarity	NPC231680
0.8415	Intermediate Similarity	NPC317242
0.8409	Intermediate Similarity	NPC155531
0.8409	Intermediate Similarity	NPC215968
0.8404	Intermediate Similarity	NPC473518
0.8391	Intermediate Similarity	NPC474156
0.8391	Intermediate Similarity	NPC320824
0.8387	Intermediate Similarity	NPC473601
0.8387	Intermediate Similarity	NPC473287
0.8387	Intermediate Similarity	NPC195297
0.837	Intermediate Similarity	NPC291203
0.837	Intermediate Similarity	NPC264101
0.837	Intermediate Similarity	NPC309866
0.837	Intermediate Similarity	NPC217205
0.837	Intermediate Similarity	NPC471464
0.837	Intermediate Similarity	NPC305418
0.837	Intermediate Similarity	NPC473503
0.837	Intermediate Similarity	NPC475325
0.8353	Intermediate Similarity	NPC16449
0.8352	Intermediate Similarity	NPC473637
0.8352	Intermediate Similarity	NPC473830
0.8352	Intermediate Similarity	NPC476668
0.8352	Intermediate Similarity	NPC204881
0.8352	Intermediate Similarity	NPC473066
0.8333	Intermediate Similarity	NPC131466
0.8333	Intermediate Similarity	NPC213528
0.8333	Intermediate Similarity	NPC244969
0.8333	Intermediate Similarity	NPC67657
0.8333	Intermediate Similarity	NPC18857
0.8316	Intermediate Similarity	NPC470030
0.8298	Intermediate Similarity	NPC83137
0.8298	Intermediate Similarity	NPC115165
0.8298	Intermediate Similarity	NPC470861
0.8298	Intermediate Similarity	NPC307534
0.8298	Intermediate Similarity	NPC303069
0.8298	Intermediate Similarity	NPC51520
0.8298	Intermediate Similarity	NPC475207
0.8298	Intermediate Similarity	NPC476112
0.8298	Intermediate Similarity	NPC232611
0.8298	Intermediate Similarity	NPC470862
0.8298	Intermediate Similarity	NPC274200
0.828	Intermediate Similarity	NPC469710
0.828	Intermediate Similarity	NPC473610
0.828	Intermediate Similarity	NPC6295
0.828	Intermediate Similarity	NPC475351
0.828	Intermediate Similarity	NPC107188
0.828	Intermediate Similarity	NPC473727
0.828	Intermediate Similarity	NPC19400
0.828	Intermediate Similarity	NPC107962
0.828	Intermediate Similarity	NPC211354
0.828	Intermediate Similarity	NPC206003
0.8276	Intermediate Similarity	NPC477285
0.8276	Intermediate Similarity	NPC111582
0.8265	Intermediate Similarity	NPC306776
0.8261	Intermediate Similarity	NPC172838
0.8261	Intermediate Similarity	NPC473726
0.8261	Intermediate Similarity	NPC137004
0.8261	Intermediate Similarity	NPC35164
0.8229	Intermediate Similarity	NPC476512
0.8229	Intermediate Similarity	NPC108227
0.8229	Intermediate Similarity	NPC475574
0.8229	Intermediate Similarity	NPC472081
0.8214	Intermediate Similarity	NPC476233
0.8214	Intermediate Similarity	NPC185915
0.8211	Intermediate Similarity	NPC291548
0.8211	Intermediate Similarity	NPC473616
0.8202	Intermediate Similarity	NPC477283
0.8193	Intermediate Similarity	NPC243027
0.8193	Intermediate Similarity	NPC196136
0.8193	Intermediate Similarity	NPC158208
0.8191	Intermediate Similarity	NPC475625
0.8191	Intermediate Similarity	NPC30856
0.8191	Intermediate Similarity	NPC476728
0.8191	Intermediate Similarity	NPC116756
0.8191	Intermediate Similarity	NPC470864
0.8191	Intermediate Similarity	NPC284104
0.8191	Intermediate Similarity	NPC160426
0.8191	Intermediate Similarity	NPC287483
0.8191	Intermediate Similarity	NPC470865
0.8191	Intermediate Similarity	NPC97700
0.8191	Intermediate Similarity	NPC145553
0.8191	Intermediate Similarity	NPC237071
0.8191	Intermediate Similarity	NPC470866
0.8191	Intermediate Similarity	NPC98018
0.8191	Intermediate Similarity	NPC470863
0.8191	Intermediate Similarity	NPC132080
0.8191	Intermediate Similarity	NPC203434
0.8191	Intermediate Similarity	NPC238796
0.8191	Intermediate Similarity	NPC128572

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 NPC128475 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	491
0.1-0.2	4465
0.2-0.3	2973
0.3-0.4	645
0.4-0.5	301
0.5-0.6	202
0.6-0.7	68
0.7-0.8	3
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
0.8571	High Similarity	NPD6928	Phase 2
0.8462	Intermediate Similarity	NPD8171	Discontinued
0.7805	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7991	Discontinued
0.7093	Intermediate Similarity	NPD4787	Phase 1
0.7054	Intermediate Similarity	NPD7516	Approved
0.6964	Remote Similarity	NPD7328	Approved
0.6964	Remote Similarity	NPD7327	Approved
0.6923	Remote Similarity	NPD6697	Approved
0.6923	Remote Similarity	NPD6118	Approved
0.6923	Remote Similarity	NPD6114	Approved
0.6923	Remote Similarity	NPD6115	Approved
0.6897	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD1811	Approved
0.6854	Remote Similarity	NPD1810	Approved
0.6842	Remote Similarity	NPD8294	Approved
0.6842	Remote Similarity	NPD8377	Approved
0.6827	Remote Similarity	NPD1700	Approved
0.6813	Remote Similarity	NPD6116	Phase 1
0.6786	Remote Similarity	NPD371	Approved
0.6783	Remote Similarity	NPD8380	Approved
0.6783	Remote Similarity	NPD8296	Approved
0.6783	Remote Similarity	NPD8378	Approved
0.6783	Remote Similarity	NPD8335	Approved
0.6783	Remote Similarity	NPD8379	Approved
0.6783	Remote Similarity	NPD8033	Approved
0.6703	Remote Similarity	NPD6117	Approved
0.6696	Remote Similarity	NPD6059	Approved
0.6696	Remote Similarity	NPD6054	Approved
0.6607	Remote Similarity	NPD8133	Approved
0.6596	Remote Similarity	NPD7525	Registered
0.6581	Remote Similarity	NPD6370	Approved
0.6555	Remote Similarity	NPD7507	Approved
0.6517	Remote Similarity	NPD2254	Approved
0.6517	Remote Similarity	NPD2687	Approved
0.6517	Remote Similarity	NPD2686	Approved
0.6514	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD7078	Approved
0.6496	Remote Similarity	NPD6016	Approved
0.6496	Remote Similarity	NPD6015	Approved
0.6484	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7492	Approved
0.6446	Remote Similarity	NPD7736	Approved
0.6444	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5988	Approved
0.6417	Remote Similarity	NPD6616	Approved
0.6413	Remote Similarity	NPD3703	Phase 2
0.6393	Remote Similarity	NPD7319	Approved
0.6364	Remote Similarity	NPD8293	Discontinued
0.6356	Remote Similarity	NPD7503	Approved
0.6348	Remote Similarity	NPD6940	Discontinued
0.6333	Remote Similarity	NPD4245	Approved
0.6333	Remote Similarity	NPD4244	Approved
0.6306	Remote Similarity	NPD8174	Phase 2
0.63	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3702	Approved
0.6224	Remote Similarity	NPD3669	Approved
0.6224	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3698	Phase 2
0.6222	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6033	Approved
0.6168	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD6009	Approved
0.6116	Remote Similarity	NPD6067	Discontinued
0.6111	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7639	Approved
0.6111	Remote Similarity	NPD7640	Approved
0.6111	Remote Similarity	NPD5360	Phase 3
0.6087	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD5777	Approved
0.6058	Remote Similarity	NPD8035	Phase 2
0.6058	Remote Similarity	NPD8034	Phase 2
0.6055	Remote Similarity	NPD4159	Approved
0.6034	Remote Similarity	NPD4632	Approved
0.6018	Remote Similarity	NPD7320	Approved
0.6018	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.5982	Remote Similarity	NPD6675	Approved
0.5982	Remote Similarity	NPD7128	Approved
0.5982	Remote Similarity	NPD6402	Approved
0.5982	Remote Similarity	NPD5739	Approved
0.5978	Remote Similarity	NPD4789	Approved
0.5965	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6700	Approved
0.5962	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD2267	Suspended
0.5948	Remote Similarity	NPD8297	Approved
0.5941	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4748	Discontinued
0.5905	Remote Similarity	NPD6703	Approved
0.5905	Remote Similarity	NPD6702	Approved
0.59	Remote Similarity	NPD6695	Phase 3
0.5882	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8308	Discontinued
0.5877	Remote Similarity	NPD6899	Approved
0.5877	Remote Similarity	NPD6881	Approved
0.5859	Remote Similarity	NPD8449	Approved
0.5841	Remote Similarity	NPD6008	Approved
0.5833	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD6372	Approved
0.5825	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7645	Phase 2
0.5814	Remote Similarity	NPD8450	Suspended
0.5789	Remote Similarity	NPD5701	Approved
0.5789	Remote Similarity	NPD5697	Approved
0.578	Remote Similarity	NPD4755	Approved
0.5778	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD7290	Approved
0.5776	Remote Similarity	NPD7102	Approved
0.5776	Remote Similarity	NPD6883	Approved
0.5776	Remote Similarity	NPD4634	Approved
0.5766	Remote Similarity	NPD7625	Phase 1
0.5745	Remote Similarity	NPD6081	Approved
0.5745	Remote Similarity	NPD4758	Discontinued
0.5743	Remote Similarity	NPD4788	Approved
0.5739	Remote Similarity	NPD6686	Approved
0.5729	Remote Similarity	NPD6942	Approved
0.5729	Remote Similarity	NPD7339	Approved
0.5726	Remote Similarity	NPD6649	Approved
0.5726	Remote Similarity	NPD6617	Approved
0.5726	Remote Similarity	NPD8130	Phase 1
0.5726	Remote Similarity	NPD6869	Approved
0.5726	Remote Similarity	NPD7604	Phase 2
0.5726	Remote Similarity	NPD6847	Approved
0.5726	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD5364	Discontinued
0.5714	Remote Similarity	NPD3671	Phase 1
0.5703	Remote Similarity	NPD5956	Approved
0.5701	Remote Similarity	NPD4202	Approved
0.57	Remote Similarity	NPD1779	Approved
0.57	Remote Similarity	NPD1780	Approved
0.5691	Remote Similarity	NPD5983	Phase 2
0.569	Remote Similarity	NPD6014	Approved
0.569	Remote Similarity	NPD6013	Approved
0.569	Remote Similarity	NPD6012	Approved
0.5676	Remote Similarity	NPD8418	Phase 2
0.5676	Remote Similarity	NPD5285	Approved
0.5676	Remote Similarity	NPD5286	Approved
0.5676	Remote Similarity	NPD4696	Approved
0.5676	Remote Similarity	NPD4700	Approved
0.5673	Remote Similarity	NPD7750	Discontinued
0.567	Remote Similarity	NPD6933	Approved
0.5641	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6083	Phase 2
0.5636	Remote Similarity	NPD6084	Phase 2
0.5635	Remote Similarity	NPD6336	Discontinued
0.5603	Remote Similarity	NPD6011	Approved
0.56	Remote Similarity	NPD6930	Phase 2
0.56	Remote Similarity	NPD8328	Phase 3
0.56	Remote Similarity	NPD6931	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