NPASS Compound

Structure

NPC113946 OpenBabel07101719242D 26 30 0 0 1 0 0 0 0 0999 V2000 -5.4044 3.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5349 2.8236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7572 2.6783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3968 2.1371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1444 0.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5627 1.5913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7353 2.4704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0041 1.9405 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0880 1.9351 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3611 1.2688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 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 -3.0104 0.6399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8080 1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 1 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 -2.8025 1.6180 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -5.0443 1.5193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3842 1.9272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 2 0 0 0 0 7 17 2 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 10 18 1 0 0 0 0 11 26 1 0 0 0 0 12 24 2 0 0 0 0 13 23 1 6 0 0 0 13 26 1 0 0 0 0 14 8 1 6 0 0 0 14 15 1 0 0 0 0 15 11 1 6 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 6 0 0 0 19 21 1 1 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 21 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.19
Volume:	364.172
LogP:	1.406
LogD:	1.603
LogS:	-3.873
# Rotatable Bonds:	2
TPSA:	49.85
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.818
Synthetic Accessibility Score:	6.177
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.102
MDCK Permeability:	3.0422595955315046e-05
Pgp-inhibitor:	0.072
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.703
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.957
Plasma Protein Binding (PPB):	35.163490295410156%
Volume Distribution (VD):	1.617
Pgp-substrate:	72.07892608642578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.178
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.648
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	5.975
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.913
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.637
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.541
Carcinogencity:	0.779
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC113946

Natural Product ID:	NPC113946
*Common Name:**	FUFCKBIZSJGNAI-RKBASDMCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FUFCKBIZSJGNAI-RKBASDMCSA-N
Standard InCHI:	InChI=1S/C21H26N2O3/c1-12(24)8-14-9-19-21(10-18-15(14)11-26-13(2)23(18)19)16-6-4-5-7-17(16)22(3)20(21)25/h4-7,13-15,18-19H,8-11H2,1-3H3/t13-,14-,15-,18+,19+,21-/m1/s1
SMILES:	CC(=O)C[C@@H]1C[C@@H]2N3[C@H]([C@@H]1CO[C@@H]3C)C[C@]12c2ccccc2N(C1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338247
PubChem CID:	15884897
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles 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
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[525455]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[525455]

☑ 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 NPC113946 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	248
0.1-0.2	1207
0.2-0.3	4365
0.3-0.4	22106
0.4-0.5	10342
0.5-0.6	3580
0.6-0.7	660
0.7-0.8	159
0.8-0.85	21
0.85-0.9	4
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.915	High Similarity	NPC472120
0.915	High Similarity	NPC472101
0.9097	High Similarity	NPC279527
0.9097	High Similarity	NPC214960
0.9032	High Similarity	NPC472106
0.8662	High Similarity	NPC472117
0.8599	High Similarity	NPC472102
0.8599	High Similarity	NPC309531
0.8526	High Similarity	NPC29285
0.8519	High Similarity	NPC139085
0.8519	High Similarity	NPC214626
0.8519	High Similarity	NPC251212
0.8405	Intermediate Similarity	NPC96901
0.8365	Intermediate Similarity	NPC225319
0.828	Intermediate Similarity	NPC478076
0.8253	Intermediate Similarity	NPC260075
0.8199	Intermediate Similarity	NPC286871
0.8199	Intermediate Similarity	NPC176983
0.8086	Intermediate Similarity	NPC99632
0.8086	Intermediate Similarity	NPC282339
0.8061	Intermediate Similarity	NPC472118
0.8013	Intermediate Similarity	NPC471123
0.8	Intermediate Similarity	NPC224970
0.8	Intermediate Similarity	NPC223595
0.8	Intermediate Similarity	NPC167724
0.7964	Intermediate Similarity	NPC476425
0.7886	Intermediate Similarity	NPC22689
0.7886	Intermediate Similarity	NPC105055
0.7877	Intermediate Similarity	NPC100863
0.787	Intermediate Similarity	NPC203202
0.787	Intermediate Similarity	NPC264482
0.7857	Intermediate Similarity	NPC285622
0.7853	Intermediate Similarity	NPC193410
0.7836	Intermediate Similarity	NPC11149
0.7821	Intermediate Similarity	NPC162440
0.7805	Intermediate Similarity	NPC248117
0.7805	Intermediate Similarity	NPC143457
0.7791	Intermediate Similarity	NPC61013
0.7771	Intermediate Similarity	NPC471124
0.7765	Intermediate Similarity	NPC476441
0.7758	Intermediate Similarity	NPC293458
0.7744	Intermediate Similarity	NPC471122
0.7684	Intermediate Similarity	NPC473298
0.7677	Intermediate Similarity	NPC469560
0.7674	Intermediate Similarity	NPC99043
0.7674	Intermediate Similarity	NPC218594
0.7674	Intermediate Similarity	NPC6974
0.767	Intermediate Similarity	NPC14994
0.7647	Intermediate Similarity	NPC473743
0.7644	Intermediate Similarity	NPC159963
0.7636	Intermediate Similarity	NPC36495
0.7628	Intermediate Similarity	NPC315051
0.7616	Intermediate Similarity	NPC476326
0.7616	Intermediate Similarity	NPC186669
0.7602	Intermediate Similarity	NPC329338
0.7602	Intermediate Similarity	NPC469726
0.7596	Intermediate Similarity	NPC67904
0.7596	Intermediate Similarity	NPC138830
0.759	Intermediate Similarity	NPC315368
0.759	Intermediate Similarity	NPC201424
0.7576	Intermediate Similarity	NPC123241
0.7571	Intermediate Similarity	NPC181928
0.7545	Intermediate Similarity	NPC472121
0.7543	Intermediate Similarity	NPC477159
0.7515	Intermediate Similarity	NPC472114
0.7515	Intermediate Similarity	NPC472115
0.75	Intermediate Similarity	NPC475489
0.75	Intermediate Similarity	NPC97584
0.75	Intermediate Similarity	NPC13367
0.7485	Intermediate Similarity	NPC66936
0.7485	Intermediate Similarity	NPC474058
0.7468	Intermediate Similarity	NPC186284
0.7468	Intermediate Similarity	NPC22082
0.7458	Intermediate Similarity	NPC259626
0.7458	Intermediate Similarity	NPC52262
0.7456	Intermediate Similarity	NPC470069
0.7456	Intermediate Similarity	NPC52059
0.7455	Intermediate Similarity	NPC161827
0.7453	Intermediate Similarity	NPC264589
0.7444	Intermediate Similarity	NPC25401
0.744	Intermediate Similarity	NPC469741
0.7433	Intermediate Similarity	NPC329833
0.7405	Intermediate Similarity	NPC130251
0.7403	Intermediate Similarity	NPC473004
0.7401	Intermediate Similarity	NPC2933
0.7401	Intermediate Similarity	NPC472119
0.7386	Intermediate Similarity	NPC476428
0.7365	Intermediate Similarity	NPC153694
0.7365	Intermediate Similarity	NPC211525
0.7356	Intermediate Similarity	NPC129624
0.7353	Intermediate Similarity	NPC475420
0.7346	Intermediate Similarity	NPC472100
0.7345	Intermediate Similarity	NPC256288
0.7333	Intermediate Similarity	NPC284706
0.733	Intermediate Similarity	NPC15840
0.7326	Intermediate Similarity	NPC469915
0.7322	Intermediate Similarity	NPC221687
0.7322	Intermediate Similarity	NPC34717
0.7321	Intermediate Similarity	NPC97380
0.7321	Intermediate Similarity	NPC310403
0.7321	Intermediate Similarity	NPC263709
0.7321	Intermediate Similarity	NPC63210
0.7321	Intermediate Similarity	NPC148468
0.7321	Intermediate Similarity	NPC243673
0.7303	Intermediate Similarity	NPC245741
0.7303	Intermediate Similarity	NPC258480
0.7294	Intermediate Similarity	NPC313757
0.7283	Intermediate Similarity	NPC355
0.7273	Intermediate Similarity	NPC475094
0.7273	Intermediate Similarity	NPC243756
0.7273	Intermediate Similarity	NPC475763
0.7263	Intermediate Similarity	NPC472107
0.7263	Intermediate Similarity	NPC473007
0.7263	Intermediate Similarity	NPC79062
0.7263	Intermediate Similarity	NPC472209
0.7256	Intermediate Similarity	NPC242000
0.7246	Intermediate Similarity	NPC473297
0.7243	Intermediate Similarity	NPC90967
0.7241	Intermediate Similarity	NPC298851
0.7241	Intermediate Similarity	NPC181138
0.7241	Intermediate Similarity	NPC473880
0.7241	Intermediate Similarity	NPC177261
0.7241	Intermediate Similarity	NPC21752
0.7241	Intermediate Similarity	NPC210415
0.7241	Intermediate Similarity	NPC276993
0.7241	Intermediate Similarity	NPC293255
0.7222	Intermediate Similarity	NPC282092
0.7222	Intermediate Similarity	NPC66210
0.7222	Intermediate Similarity	NPC473615
0.7212	Intermediate Similarity	NPC473329
0.72	Intermediate Similarity	NPC470548
0.7198	Intermediate Similarity	NPC473569
0.7195	Intermediate Similarity	NPC212799
0.7182	Intermediate Similarity	NPC229484
0.7181	Intermediate Similarity	NPC471512
0.7168	Intermediate Similarity	NPC475248
0.7168	Intermediate Similarity	NPC63047
0.716	Intermediate Similarity	NPC222029
0.7143	Intermediate Similarity	NPC470301
0.7143	Intermediate Similarity	NPC292675
0.7143	Intermediate Similarity	NPC301760
0.7135	Intermediate Similarity	NPC85651
0.7135	Intermediate Similarity	NPC230313
0.7135	Intermediate Similarity	NPC243626
0.7104	Intermediate Similarity	NPC472112
0.7104	Intermediate Similarity	NPC473008
0.7097	Intermediate Similarity	NPC97100
0.7097	Intermediate Similarity	NPC473375
0.7088	Intermediate Similarity	NPC21425
0.7088	Intermediate Similarity	NPC472323
0.7081	Intermediate Similarity	NPC470485
0.7079	Intermediate Similarity	NPC321211
0.7077	Intermediate Similarity	NPC159815
0.7076	Intermediate Similarity	NPC68650
0.7072	Intermediate Similarity	NPC322621
0.7066	Intermediate Similarity	NPC154602
0.7062	Intermediate Similarity	NPC320147
0.7059	Intermediate Similarity	NPC475559
0.7055	Intermediate Similarity	NPC469537
0.7055	Intermediate Similarity	NPC308197
0.7053	Intermediate Similarity	NPC473005
0.7041	Intermediate Similarity	NPC473006
0.7039	Intermediate Similarity	NPC286994
0.7033	Intermediate Similarity	NPC478077
0.7027	Intermediate Similarity	NPC472113
0.7024	Intermediate Similarity	NPC122106
0.7018	Intermediate Similarity	NPC276085
0.699	Remote Similarity	NPC10732
0.6978	Remote Similarity	NPC476095
0.6973	Remote Similarity	NPC470483
0.6973	Remote Similarity	NPC472097
0.6971	Remote Similarity	NPC33507
0.6968	Remote Similarity	NPC302548
0.6959	Remote Similarity	NPC104345
0.6935	Remote Similarity	NPC204970
0.6933	Remote Similarity	NPC471164
0.6931	Remote Similarity	NPC138615
0.6931	Remote Similarity	NPC265642
0.6931	Remote Similarity	NPC132874
0.6931	Remote Similarity	NPC218733
0.6902	Remote Similarity	NPC285841
0.6901	Remote Similarity	NPC469536
0.6885	Remote Similarity	NPC469460
0.6882	Remote Similarity	NPC22476
0.6882	Remote Similarity	NPC203628
0.6871	Remote Similarity	NPC243162
0.6867	Remote Similarity	NPC116519
0.6856	Remote Similarity	NPC477161
0.6856	Remote Similarity	NPC277350
0.6854	Remote Similarity	NPC242269
0.6845	Remote Similarity	NPC109787
0.6842	Remote Similarity	NPC52557
0.6839	Remote Similarity	NPC194881
0.6839	Remote Similarity	NPC477179
0.6833	Remote Similarity	NPC234987
0.6832	Remote Similarity	NPC318525
0.6832	Remote Similarity	NPC10653
0.6828	Remote Similarity	NPC5630
0.6828	Remote Similarity	NPC314333
0.6828	Remote Similarity	NPC329858

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 NPC113946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	507
0.2-0.3	714
0.3-0.4	1486
0.4-0.5	3537
0.5-0.6	2328
0.6-0.7	386
0.7-0.8	16
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
0.774	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6566	Discontinued
0.7289	Intermediate Similarity	NPD4120	Approved
0.7289	Intermediate Similarity	NPD4121	Phase 3
0.7246	Intermediate Similarity	NPD5742	Approved
0.7246	Intermediate Similarity	NPD5743	Approved
0.7246	Intermediate Similarity	NPD5741	Approved
0.7178	Intermediate Similarity	NPD5931	Phase 3
0.7178	Intermediate Similarity	NPD5933	Phase 3
0.7178	Intermediate Similarity	NPD5932	Phase 3
0.7134	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5918	Discontinued
0.7117	Intermediate Similarity	NPD7487	Discontinued
0.7101	Intermediate Similarity	NPD1663	Discontinued
0.7089	Intermediate Similarity	NPD5182	Approved
0.7089	Intermediate Similarity	NPD5184	Approved
0.7089	Intermediate Similarity	NPD5185	Approved
0.7076	Intermediate Similarity	NPD7600	Phase 2
0.7048	Intermediate Similarity	NPD4682	Phase 2
0.7018	Intermediate Similarity	NPD7599	Phase 2
0.7007	Intermediate Similarity	NPD5179	Approved
0.7007	Intermediate Similarity	NPD5181	Approved
0.7007	Intermediate Similarity	NPD5180	Approved
0.6951	Remote Similarity	NPD2820	Phase 3
0.6933	Remote Similarity	NPD5990	Approved
0.6933	Remote Similarity	NPD5991	Approved
0.6902	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2365	Approved
0.6887	Remote Similarity	NPD2994	Approved
0.6887	Remote Similarity	NPD6343	Approved
0.6887	Remote Similarity	NPD6345	Approved
0.6883	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2790	Discontinued
0.6865	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5997	Discontinued
0.6852	Remote Similarity	NPD6358	Phase 2
0.6845	Remote Similarity	NPD5942	Approved
0.6845	Remote Similarity	NPD5941	Approved
0.6835	Remote Similarity	NPD5131	Approved
0.6828	Remote Similarity	NPD4499	Approved
0.6821	Remote Similarity	NPD2117	Pre-registration
0.6821	Remote Similarity	NPD2115	Approved
0.6821	Remote Similarity	NPD2116	Approved
0.6815	Remote Similarity	NPD5993	Phase 1
0.6798	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6489	Phase 3
0.679	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6768	Approved
0.6786	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4549	Discontinued
0.6771	Remote Similarity	NPD6805	Discontinued
0.6766	Remote Similarity	NPD6017	Discontinued
0.6763	Remote Similarity	NPD8630	Approved
0.6753	Remote Similarity	NPD2946	Phase 2
0.6742	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3030	Approved
0.6732	Remote Similarity	NPD3031	Approved
0.6732	Remote Similarity	NPD3032	Approved
0.6727	Remote Similarity	NPD2093	Discontinued
0.6727	Remote Similarity	NPD3625	Discontinued
0.6722	Remote Similarity	NPD3423	Phase 2
0.6722	Remote Similarity	NPD3422	Phase 3
0.6684	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7295	Approved
0.6667	Remote Similarity	NPD7606	Phase 3
0.6667	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5183	Approved
0.6648	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5186	Approved
0.6648	Remote Similarity	NPD5600	Discontinued
0.6647	Remote Similarity	NPD4430	Phase 2
0.6646	Remote Similarity	NPD2670	Approved
0.6632	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2791	Discontinued
0.6625	Remote Similarity	NPD4365	Phase 2
0.6622	Remote Similarity	NPD4116	Approved
0.661	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3790	Phase 2
0.6606	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4176	Approved
0.6603	Remote Similarity	NPD4178	Approved
0.6601	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4500	Approved
0.6598	Remote Similarity	NPD4501	Approved
0.6597	Remote Similarity	NPD4602	Approved
0.6592	Remote Similarity	NPD6457	Approved
0.6591	Remote Similarity	NPD5992	Approved
0.6591	Remote Similarity	NPD2506	Approved
0.6591	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7478	Approved
0.6584	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5578	Approved
0.6582	Remote Similarity	NPD6792	Phase 3
0.6582	Remote Similarity	NPD7205	Discontinued
0.6576	Remote Similarity	NPD6879	Phase 2
0.6576	Remote Similarity	NPD6878	Phase 2
0.6566	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3449	Discontinued
0.6556	Remote Similarity	NPD7795	Phase 2
0.655	Remote Similarity	NPD4942	Approved
0.6548	Remote Similarity	NPD7082	Approved
0.6548	Remote Similarity	NPD5024	Approved
0.6545	Remote Similarity	NPD6342	Discontinued
0.6545	Remote Similarity	NPD5318	Discontinued
0.6536	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5823	Approved
0.6536	Remote Similarity	NPD6070	Approved
0.6536	Remote Similarity	NPD6069	Approved
0.6534	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD33	Approved
0.6534	Remote Similarity	NPD4393	Approved
0.6532	Remote Similarity	NPD8401	Approved
0.6532	Remote Similarity	NPD8402	Approved
0.6532	Remote Similarity	NPD8400	Approved
0.6531	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4601	Approved
0.6513	Remote Similarity	NPD4600	Approved
0.6509	Remote Similarity	NPD7259	Approved
0.6503	Remote Similarity	NPD2950	Approved
0.6503	Remote Similarity	NPD2949	Approved
0.6494	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2607	Approved
0.6484	Remote Similarity	NPD3377	Discontinued
0.648	Remote Similarity	NPD6321	Discontinued
0.6471	Remote Similarity	NPD7483	Phase 2
0.6471	Remote Similarity	NPD7482	Phase 2
0.6462	Remote Similarity	NPD6999	Discontinued
0.6462	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6891	Phase 2
0.6453	Remote Similarity	NPD979	Approved
0.6453	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7665	Phase 2
0.645	Remote Similarity	NPD7666	Phase 3
0.6447	Remote Similarity	NPD3387	Approved
0.6441	Remote Similarity	NPD6629	Discontinued
0.6441	Remote Similarity	NPD2427	Approved
0.644	Remote Similarity	NPD8240	Discontinued
0.6433	Remote Similarity	NPD3141	Discontinued
0.6432	Remote Similarity	NPD7001	Phase 3
0.6429	Remote Similarity	NPD2010	Phase 3
0.6424	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD1064	Approved
0.6419	Remote Similarity	NPD1065	Approved
0.6416	Remote Similarity	NPD5748	Phase 2
0.6413	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD2037	Approved
0.6407	Remote Similarity	NPD3170	Approved
0.6405	Remote Similarity	NPD3551	Approved
0.6402	Remote Similarity	NPD1527	Phase 2
0.6402	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7086	Phase 2
0.64	Remote Similarity	NPD7633	Discontinued
0.6398	Remote Similarity	NPD4330	Approved
0.6398	Remote Similarity	NPD4329	Approved
0.6395	Remote Similarity	NPD1801	Approved
0.6395	Remote Similarity	NPD1802	Approved
0.6392	Remote Similarity	NPD4215	Approved
0.6392	Remote Similarity	NPD4216	Approved
0.6392	Remote Similarity	NPD3131	Approved
0.6392	Remote Similarity	NPD2610	Approved
0.6392	Remote Similarity	NPD2609	Approved
0.6392	Remote Similarity	NPD2608	Approved
0.6392	Remote Similarity	NPD2611	Approved
0.6392	Remote Similarity	NPD3132	Approved
0.6392	Remote Similarity	NPD4217	Approved
0.6392	Remote Similarity	NPD4218	Approved
0.6392	Remote Similarity	NPD2612	Approved
0.6386	Remote Similarity	NPD6073	Approved
0.6384	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.638	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD1036	Approved
0.637	Remote Similarity	NPD4803	Discontinued
0.6364	Remote Similarity	NPD7072	Phase 2
0.6364	Remote Similarity	NPD3471	Approved
0.6364	Remote Similarity	NPD3470	Approved
0.6359	Remote Similarity	NPD7572	Phase 2
0.6359	Remote Similarity	NPD5466	Approved
0.6359	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6659	Phase 2
0.6354	Remote Similarity	NPD5504	Discontinued
0.6353	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5526	Phase 2
0.6352	Remote Similarity	NPD6408	Phase 1
0.635	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD2569	Approved
0.6347	Remote Similarity	NPD2567	Approved
0.6344	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5293	Phase 2
0.6339	Remote Similarity	NPD2431	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