NPASS Compound

Structure

NPC470069 OpenBabel07101719132D 32 35 0 0 1 0 0 0 0 0999 V2000 -4.9504 3.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8164 1.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9504 5.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6203 3.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9504 2.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0214 2.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0269 2.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 1.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3799 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0159 -0.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0104 -0.6399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9504 0.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 1.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0844 3.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8164 0.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0844 1.8383 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2183 2.3383 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2183 3.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0844 0.8383 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3523 0.8383 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3523 3.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2183 0.3383 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -6.6824 0.3383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 4.8383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0844 4.8383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 3.3383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 15 1 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 2 0 0 0 0 9 20 2 0 0 0 0 10 11 1 0 0 0 0 11 27 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 18 2 0 0 0 0 14 31 1 0 0 0 0 15 28 2 0 0 0 0 16 5 1 6 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 1 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 1 0 0 0 22 25 1 1 0 0 0 22 27 1 0 0 0 0 23 29 2 0 0 0 0 23 32 1 0 0 0 0 24 25 1 0 0 0 0 24 26 2 0 0 0 0 24 30 1 0 0 0 0 25 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.23
Volume:	454.22
LogP:	2.883
LogD:	3.106
LogS:	-3.827
# Rotatable Bonds:	7
TPSA:	84.94
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	5.1
Fsp3:	0.56
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:	-4.647
MDCK Permeability:	3.714419653988443e-05
Pgp-inhibitor:	0.483
Pgp-substrate:	0.354
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.591
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	60.54560470581055%
Volume Distribution (VD):	0.875
Pgp-substrate:	31.77391815185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.498
CYP2C19-inhibitor:	0.341
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.408
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.892
CYP2D6-substrate:	0.716
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.934

ADMET: Excretion

Clearance (CL):	12.196
Half-life (T1/2):	0.37

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.735
Drug-inuced Liver Injury (DILI):	0.639
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.729
Carcinogencity:	0.662
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC470069

Natural Product ID:	NPC470069
*Common Name:**	Macrophylline B
IUPAC Name:	methyl (Z)-2-[(3S,5'S,6'R,7'S,8'aS)-6'-ethyl-2-oxo-5'-(2-oxopropyl)spiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate
Synonyms:	Macrophylline B
Standard InCHIKey:	VWNYHBABHBBFQC-ISZZZUSESA-N
Standard InCHI:	InChI=1S/C25H32N2O5/c1-5-16-17(18(14-31-3)23(29)32-4)13-22-25(10-11-27(22)21(16)12-15(2)28)19-8-6-7-9-20(19)26-24(25)30/h6-9,14,16-17,21-22H,5,10-13H2,1-4H3,(H,26,30)/b18-14-/t16-,17+,21+,22+,25+/m1/s1
SMILES:	CCC1C(CC2C3(CCN2C1CC(=O)C)C4=CC=CC=C4NC3=O)C(=COC)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668785
PubChem CID:	53326135
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000251] Indolizidines

*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
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21070010]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21070010]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	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	4

Activity Type	# Activity
Cell Line	2
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[541880]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[541880]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	>	30.0	ug.mL-1	PMID[541880]

☑ 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 NPC470069 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	178
0.1-0.2	861
0.2-0.3	2695
0.3-0.4	9701
0.4-0.5	20599
0.5-0.6	6849
0.6-0.7	1634
0.7-0.8	154
0.8-0.85	4
0.85-0.9	4
0.9-0.95	6
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC52059
0.9733	High Similarity	NPC243673
0.9733	High Similarity	NPC148468
0.9733	High Similarity	NPC63210
0.9733	High Similarity	NPC263709
0.9733	High Similarity	NPC310403
0.9733	High Similarity	NPC97380
0.9536	High Similarity	NPC153694
0.9536	High Similarity	NPC211525
0.9533	High Similarity	NPC161827
0.9304	High Similarity	NPC210415
0.9304	High Similarity	NPC276993
0.9304	High Similarity	NPC181138
0.9304	High Similarity	NPC21752
0.9304	High Similarity	NPC298851
0.9304	High Similarity	NPC293255
0.8861	High Similarity	NPC472121
0.8133	Intermediate Similarity	NPC278887
0.7987	Intermediate Similarity	NPC472100
0.7921	Intermediate Similarity	NPC28510
0.7892	Intermediate Similarity	NPC474058
0.7874	Intermediate Similarity	NPC475962
0.7862	Intermediate Similarity	NPC472103
0.7778	Intermediate Similarity	NPC204970
0.7746	Intermediate Similarity	NPC476441
0.774	Intermediate Similarity	NPC469460
0.7735	Intermediate Similarity	NPC203972
0.7667	Intermediate Similarity	NPC174629
0.7661	Intermediate Similarity	NPC469462
0.7651	Intermediate Similarity	NPC473297
0.763	Intermediate Similarity	NPC476425
0.7602	Intermediate Similarity	NPC279527
0.7602	Intermediate Similarity	NPC214960
0.759	Intermediate Similarity	NPC478076
0.7586	Intermediate Similarity	NPC13367
0.7584	Intermediate Similarity	NPC97584
0.7558	Intermediate Similarity	NPC223595
0.7558	Intermediate Similarity	NPC167724
0.7558	Intermediate Similarity	NPC224970
0.7557	Intermediate Similarity	NPC99043
0.7557	Intermediate Similarity	NPC218594
0.7515	Intermediate Similarity	NPC193410
0.75	Intermediate Similarity	NPC472114
0.75	Intermediate Similarity	NPC472115
0.75	Intermediate Similarity	NPC243162
0.75	Intermediate Similarity	NPC474077
0.75	Intermediate Similarity	NPC282092
0.7472	Intermediate Similarity	NPC476428
0.7471	Intermediate Similarity	NPC225319
0.7471	Intermediate Similarity	NPC143457
0.7471	Intermediate Similarity	NPC248117
0.7456	Intermediate Similarity	NPC113946
0.7456	Intermediate Similarity	NPC61013
0.7444	Intermediate Similarity	NPC472209
0.7443	Intermediate Similarity	NPC203202
0.7443	Intermediate Similarity	NPC264482
0.7427	Intermediate Similarity	NPC293458
0.7412	Intermediate Similarity	NPC36495
0.7386	Intermediate Similarity	NPC317758
0.7363	Intermediate Similarity	NPC14994
0.736	Intermediate Similarity	NPC6974
0.7326	Intermediate Similarity	NPC472101
0.7326	Intermediate Similarity	NPC472117
0.7326	Intermediate Similarity	NPC282339
0.7326	Intermediate Similarity	NPC472120
0.7326	Intermediate Similarity	NPC99632
0.7318	Intermediate Similarity	NPC39822
0.731	Intermediate Similarity	NPC469461
0.7308	Intermediate Similarity	NPC291759
0.7303	Intermediate Similarity	NPC186669
0.7303	Intermediate Similarity	NPC476326
0.7294	Intermediate Similarity	NPC29285
0.7293	Intermediate Similarity	NPC245741
0.7288	Intermediate Similarity	NPC469726
0.7288	Intermediate Similarity	NPC329338
0.7283	Intermediate Similarity	NPC313757
0.7267	Intermediate Similarity	NPC472102
0.7267	Intermediate Similarity	NPC309531
0.7253	Intermediate Similarity	NPC133591
0.7251	Intermediate Similarity	NPC123241
0.7241	Intermediate Similarity	NPC472106
0.7238	Intermediate Similarity	NPC159963
0.7234	Intermediate Similarity	NPC475559
0.7234	Intermediate Similarity	NPC302548
0.7196	Intermediate Similarity	NPC100863
0.7196	Intermediate Similarity	NPC138615
0.7196	Intermediate Similarity	NPC132874
0.7196	Intermediate Similarity	NPC218733
0.7196	Intermediate Similarity	NPC265642
0.7189	Intermediate Similarity	NPC5630
0.7174	Intermediate Similarity	NPC472323
0.7174	Intermediate Similarity	NPC21425
0.7167	Intermediate Similarity	NPC321211
0.7158	Intermediate Similarity	NPC322621
0.7151	Intermediate Similarity	NPC203628
0.7151	Intermediate Similarity	NPC25401
0.7135	Intermediate Similarity	NPC102338
0.7135	Intermediate Similarity	NPC96901
0.7135	Intermediate Similarity	NPC111602
0.7135	Intermediate Similarity	NPC63199
0.7135	Intermediate Similarity	NPC196251
0.7126	Intermediate Similarity	NPC476231
0.712	Intermediate Similarity	NPC207033
0.712	Intermediate Similarity	NPC38823
0.7119	Intermediate Similarity	NPC472118
0.7104	Intermediate Similarity	NPC258480
0.7097	Intermediate Similarity	NPC105055
0.7097	Intermediate Similarity	NPC22689
0.7093	Intermediate Similarity	NPC477157
0.7093	Intermediate Similarity	NPC477156
0.7083	Intermediate Similarity	NPC469732
0.7065	Intermediate Similarity	NPC52262
0.7062	Intermediate Similarity	NPC14339
0.7055	Intermediate Similarity	NPC281104
0.7047	Intermediate Similarity	NPC1464
0.7039	Intermediate Similarity	NPC214626
0.7039	Intermediate Similarity	NPC251212
0.7039	Intermediate Similarity	NPC139085
0.7035	Intermediate Similarity	NPC114808
0.7033	Intermediate Similarity	NPC15840
0.7029	Intermediate Similarity	NPC286871
0.7029	Intermediate Similarity	NPC176983
0.7026	Intermediate Similarity	NPC246140
0.7026	Intermediate Similarity	NPC195787
0.7022	Intermediate Similarity	NPC469915
0.7021	Intermediate Similarity	NPC55493
0.7011	Intermediate Similarity	NPC472119
0.7	Intermediate Similarity	NPC316746
0.7	Intermediate Similarity	NPC303214
0.6995	Remote Similarity	NPC232600
0.6979	Remote Similarity	NPC241024
0.6974	Remote Similarity	NPC87714
0.6973	Remote Similarity	NPC473007
0.6971	Remote Similarity	NPC315368
0.6971	Remote Similarity	NPC201424
0.697	Remote Similarity	NPC315051
0.6968	Remote Similarity	NPC22476
0.6964	Remote Similarity	NPC116519
0.6963	Remote Similarity	NPC90967
0.6947	Remote Similarity	NPC221687
0.6943	Remote Similarity	NPC312870
0.6943	Remote Similarity	NPC199851
0.6943	Remote Similarity	NPC254240
0.6943	Remote Similarity	NPC214428
0.6943	Remote Similarity	NPC294909
0.6943	Remote Similarity	NPC475489
0.6943	Remote Similarity	NPC128265
0.6939	Remote Similarity	NPC277350
0.6927	Remote Similarity	NPC52557
0.6918	Remote Similarity	NPC478079
0.6915	Remote Similarity	NPC473008
0.6915	Remote Similarity	NPC473298
0.6915	Remote Similarity	NPC474059
0.6915	Remote Similarity	NPC472112
0.6914	Remote Similarity	NPC471122
0.6911	Remote Similarity	NPC245916
0.69	Remote Similarity	NPC127996
0.6899	Remote Similarity	NPC325013
0.6898	Remote Similarity	NPC473815
0.6898	Remote Similarity	NPC181928
0.6893	Remote Similarity	NPC189116
0.6865	Remote Similarity	NPC477159
0.6862	Remote Similarity	NPC217294
0.6862	Remote Similarity	NPC284706
0.6859	Remote Similarity	NPC474121
0.6851	Remote Similarity	NPC285622
0.6848	Remote Similarity	NPC11149
0.6845	Remote Similarity	NPC66210
0.6845	Remote Similarity	NPC106593
0.6845	Remote Similarity	NPC314287
0.6842	Remote Similarity	NPC473004
0.6842	Remote Similarity	NPC300596
0.6842	Remote Similarity	NPC237649
0.6834	Remote Similarity	NPC469743
0.6832	Remote Similarity	NPC189661
0.6831	Remote Similarity	NPC260075
0.6829	Remote Similarity	NPC140311
0.6826	Remote Similarity	NPC316202
0.6825	Remote Similarity	NPC314333
0.6825	Remote Similarity	NPC329858
0.6824	Remote Similarity	NPC478039
0.6823	Remote Similarity	NPC473375
0.6823	Remote Similarity	NPC97100
0.6816	Remote Similarity	NPC472098
0.6815	Remote Similarity	NPC169485
0.6815	Remote Similarity	NPC84281
0.6815	Remote Similarity	NPC317474
0.6815	Remote Similarity	NPC291027
0.6815	Remote Similarity	NPC213126
0.6812	Remote Similarity	NPC473667
0.6811	Remote Similarity	NPC113626
0.68	Remote Similarity	NPC269449
0.6798	Remote Similarity	NPC152768
0.6798	Remote Similarity	NPC148183
0.6798	Remote Similarity	NPC470001
0.6798	Remote Similarity	NPC234772
0.6798	Remote Similarity	NPC470002
0.6796	Remote Similarity	NPC355
0.6788	Remote Similarity	NPC208725
0.6786	Remote Similarity	NPC162730

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 NPC470069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	425
0.2-0.3	653
0.3-0.4	1067
0.4-0.5	3042
0.5-0.6	3194
0.6-0.7	632
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7174	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7599	Phase 2
0.7081	Intermediate Similarity	NPD5185	Approved
0.7081	Intermediate Similarity	NPD5182	Approved
0.7081	Intermediate Similarity	NPD5184	Approved
0.7069	Intermediate Similarity	NPD7600	Phase 2
0.7055	Intermediate Similarity	NPD2569	Approved
0.7055	Intermediate Similarity	NPD2567	Approved
0.7045	Intermediate Similarity	NPD7591	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5741	Approved
0.7035	Intermediate Similarity	NPD5743	Approved
0.7035	Intermediate Similarity	NPD5742	Approved
0.7012	Intermediate Similarity	NPD3170	Approved
0.6993	Remote Similarity	NPD2994	Approved
0.6977	Remote Similarity	NPD4120	Approved
0.6977	Remote Similarity	NPD4121	Phase 3
0.6964	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4500	Approved
0.6943	Remote Similarity	NPD4501	Approved
0.6928	Remote Similarity	NPD2117	Pre-registration
0.6928	Remote Similarity	NPD2116	Approved
0.6928	Remote Similarity	NPD2115	Approved
0.6872	Remote Similarity	NPD2844	Phase 3
0.6859	Remote Similarity	NPD2946	Phase 2
0.6848	Remote Similarity	NPD2670	Approved
0.6842	Remote Similarity	NPD7570	Approved
0.6842	Remote Similarity	NPD7569	Approved
0.6839	Remote Similarity	NPD3032	Approved
0.6839	Remote Similarity	NPD3031	Approved
0.6839	Remote Similarity	NPD2210	Approved
0.6839	Remote Similarity	NPD3030	Approved
0.6839	Remote Similarity	NPD2212	Approved
0.6833	Remote Similarity	NPD7795	Phase 2
0.6825	Remote Similarity	NPD4499	Approved
0.6824	Remote Similarity	NPD6416	Phase 2
0.6815	Remote Similarity	NPD2608	Approved
0.6815	Remote Similarity	NPD2609	Approved
0.6815	Remote Similarity	NPD2610	Approved
0.6815	Remote Similarity	NPD2611	Approved
0.6815	Remote Similarity	NPD4215	Approved
0.6815	Remote Similarity	NPD4217	Approved
0.6815	Remote Similarity	NPD4218	Approved
0.6815	Remote Similarity	NPD3132	Approved
0.6815	Remote Similarity	NPD3131	Approved
0.6815	Remote Similarity	NPD2612	Approved
0.6815	Remote Similarity	NPD4216	Approved
0.6804	Remote Similarity	NPD6874	Approved
0.6786	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5811	Approved
0.6774	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4602	Approved
0.6757	Remote Similarity	NPD6879	Phase 2
0.6757	Remote Similarity	NPD6878	Phase 2
0.6746	Remote Similarity	NPD2820	Phase 3
0.6744	Remote Similarity	NPD4682	Phase 2
0.6743	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1110	Approved
0.6707	Remote Similarity	NPD1109	Approved
0.6702	Remote Similarity	NPD5077	Approved
0.6702	Remote Similarity	NPD5076	Approved
0.6687	Remote Similarity	NPD6325	Discontinued
0.6686	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2365	Approved
0.6685	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6805	Discontinued
0.6684	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7205	Discontinued
0.6667	Remote Similarity	NPD6017	Discontinued
0.6667	Remote Similarity	NPD8416	Discontinued
0.6667	Remote Similarity	NPD4796	Discontinued
0.6667	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3965	Phase 1
0.6648	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7528	Approved
0.6633	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3423	Phase 2
0.663	Remote Similarity	NPD3422	Phase 3
0.6629	Remote Similarity	NPD3399	Approved
0.6629	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4041	Approved
0.6627	Remote Similarity	NPD8643	Discontinued
0.6626	Remote Similarity	NPD2613	Approved
0.6615	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2435	Approved
0.6607	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2607	Approved
0.66	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD4601	Approved
0.6599	Remote Similarity	NPD4600	Approved
0.6593	Remote Similarity	NPD3983	Phase 3
0.6593	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2506	Approved
0.659	Remote Similarity	NPD1802	Approved
0.659	Remote Similarity	NPD1801	Approved
0.6573	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7605	Discovery
0.6569	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD1573	Approved
0.6557	Remote Similarity	NPD1575	Approved
0.6556	Remote Similarity	NPD1742	Approved
0.6556	Remote Similarity	NPD1743	Approved
0.6556	Remote Similarity	NPD19	Approved
0.6552	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8283	Approved
0.655	Remote Similarity	NPD8282	Approved
0.655	Remote Similarity	NPD56	Approved
0.655	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6999	Discontinued
0.6548	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6891	Phase 2
0.6541	Remote Similarity	NPD5466	Approved
0.6538	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD2948	Discontinued
0.6529	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.652	Remote Similarity	NPD4493	Discontinued
0.652	Remote Similarity	NPD7470	Discontinued
0.6517	Remote Similarity	NPD1663	Discontinued
0.6517	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7001	Phase 3
0.6517	Remote Similarity	NPD2672	Discontinued
0.6517	Remote Similarity	NPD7105	Phase 1
0.6514	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7613	Discontinued
0.6512	Remote Similarity	NPD7487	Discontinued
0.6506	Remote Similarity	NPD3089	Approved
0.6506	Remote Similarity	NPD3616	Approved
0.6506	Remote Similarity	NPD2570	Approved
0.6506	Remote Similarity	NPD4745	Approved
0.6506	Remote Similarity	NPD3615	Approved
0.6506	Remote Similarity	NPD2566	Approved
0.6506	Remote Similarity	NPD4746	Phase 3
0.6506	Remote Similarity	NPD3614	Approved
0.6506	Remote Similarity	NPD2571	Approved
0.6506	Remote Similarity	NPD3088	Approved
0.6506	Remote Similarity	NPD3090	Approved
0.6506	Remote Similarity	NPD2573	Approved
0.6506	Remote Similarity	NPD3087	Approved
0.6506	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2574	Discontinued
0.6503	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7777	Approved
0.6497	Remote Similarity	NPD4397	Phase 1
0.6497	Remote Similarity	NPD53	Approved
0.6497	Remote Similarity	NPD7778	Approved
0.6494	Remote Similarity	NPD181	Approved
0.6488	Remote Similarity	NPD6073	Approved
0.6488	Remote Similarity	NPD8173	Phase 2
0.6488	Remote Similarity	NPD8172	Phase 2
0.6481	Remote Similarity	NPD1036	Approved
0.6481	Remote Similarity	NPD5578	Approved
0.6481	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7606	Phase 3
0.6474	Remote Similarity	NPD7281	Phase 3
0.6474	Remote Similarity	NPD4412	Phase 2
0.6474	Remote Similarity	NPD7295	Approved
0.6474	Remote Similarity	NPD7280	Phase 3
0.6474	Remote Similarity	NPD2622	Approved
0.6471	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6987	Phase 1
0.6461	Remote Similarity	NPD5617	Suspended
0.646	Remote Similarity	NPD2584	Suspended
0.6453	Remote Similarity	NPD8399	Phase 1
0.6453	Remote Similarity	NPD4082	Approved
0.6453	Remote Similarity	NPD2510	Approved
0.6453	Remote Similarity	NPD8423	Phase 2
0.6453	Remote Similarity	NPD2509	Approved
0.6452	Remote Similarity	NPD3150	Approved
0.6452	Remote Similarity	NPD3147	Approved
0.6452	Remote Similarity	NPD3148	Approved
0.6452	Remote Similarity	NPD2659	Approved
0.6452	Remote Similarity	NPD3149	Approved
0.6452	Remote Similarity	NPD2658	Approved
0.6447	Remote Similarity	NPD5003	Discontinued
0.6444	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD2427	Approved
0.6443	Remote Similarity	NPD2336	Approved
0.6442	Remote Similarity	NPD2159	Approved
0.6442	Remote Similarity	NPD2626	Approved
0.6442	Remote Similarity	NPD2160	Approved
0.6442	Remote Similarity	NPD1593	Approved
0.6442	Remote Similarity	NPD2627	Approved
0.6442	Remote Similarity	NPD2625	Approved
0.6442	Remote Similarity	NPD2628	Approved
0.6436	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3625	Discontinued
0.6429	Remote Similarity	NPD4686	Approved
0.6429	Remote Similarity	NPD4685	Phase 3
0.6429	Remote Similarity	NPD1631	Approved
0.6429	Remote Similarity	NPD4427	Phase 2
0.6429	Remote Similarity	NPD5088	Discontinued
0.6429	Remote Similarity	NPD4684	Phase 3
0.6425	Remote Similarity	NPD4334	Discontinued

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