NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	394.1
Volume:	350.508
LogP:	1.375
LogD:	0.842
LogS:	-2.374
# Rotatable Bonds:	11
TPSA:	100.01
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.281
Synthetic Accessibility Score:	2.444
Fsp3:	0.412
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.809
MDCK Permeability:	5.442648216558155e-06
Pgp-inhibitor:	0.05
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.097
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.27

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	30.032215118408203%
Volume Distribution (VD):	1.869
Pgp-substrate:	78.32999420166016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.756
CYP1A2-substrate:	0.516
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.882
CYP2D6-substrate:	0.768
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	3.851
Half-life (T1/2):	0.352

ADMET: Toxicity

hERG Blockers:	0.472
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.757
AMES Toxicity:	0.724
Rat Oral Acute Toxicity:	0.528
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.826
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.252

Download Data

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

Natural Product: NPC477004

Natural Product ID:	NPC477004
*Common Name:**	Didemnidine B
IUPAC Name:	N-[3-(4-aminobutylamino)propyl]-2-(6-bromo-1H-indol-3-yl)-2-oxoacetamide
Synonyms:	Didemnidine B
Standard InCHIKey:	IAMCWSVWBJVYIO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H23BrN4O2/c18-12-4-5-13-14(11-22-15(13)10-12)16(23)17(24)21-9-3-8-20-7-2-1-6-19/h4-5,10-11,20,22H,1-3,6-9,19H2,(H,21,24)
SMILES:	C1=CC2=C(C=C1Br)NC=C2C(=O)C(=O)NCCCNCCCCN
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1789813
PubChem CID:	52950926
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO33591	Didemnum sp.	Species	Didemnidae	Eukaryota	n.a.	Stanley Reef, the Great Barrier Reef, Queensland, Australia	1983-MAY	PMID[12086492]
NPO33591	Didemnum sp.	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO33591	Didemnum sp.	Species	Didemnidae	Eukaryota	n.a.	Tiwai Wharf, Tiwai Point, Southland, New Zealand (4635.52' S, 16821.14' E)	2007-AUG	PMID[21348447]
NPO33591	Didemnum sp.	Species	Didemnidae	Eukaryota	n.a.	at a depth of 7 m from wooden piles at Tiwai Wharf, Tiwai Point, Southland, New Zealand (4635.52' S, 16821.14' E)	2007-AUG	PMID[21348447]

☑ 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	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	25000	nM	PMID[21348447]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	15000	nM	PMID[21348447]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	160000	nM	PMID[21348447]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	82000	nM	PMID[21348447]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	44000	nM	PMID[21348447]

☑ 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 NPC477004 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	509
0.1-0.2	6132
0.2-0.3	19579
0.3-0.4	10800
0.4-0.5	2368
0.5-0.6	2000
0.6-0.7	1103
0.7-0.8	186
0.8-0.85	18
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9261	High Similarity	NPC477003
0.8833	High Similarity	NPC110158
0.875	High Similarity	NPC476460
0.8624	High Similarity	NPC237414
0.8571	High Similarity	NPC473218
0.8571	High Similarity	NPC470702
0.8528	High Similarity	NPC470703
0.8526	High Similarity	NPC153123
0.8526	High Similarity	NPC220797
0.8526	High Similarity	NPC475914
0.8526	High Similarity	NPC474318
0.8526	High Similarity	NPC201266
0.8526	High Similarity	NPC268744
0.8482	Intermediate Similarity	NPC77241
0.8482	Intermediate Similarity	NPC13456
0.8482	Intermediate Similarity	NPC166209
0.8482	Intermediate Similarity	NPC269203
0.8352	Intermediate Similarity	NPC284775
0.8263	Intermediate Similarity	NPC304203
0.8256	Intermediate Similarity	NPC317701
0.8187	Intermediate Similarity	NPC474389
0.8173	Intermediate Similarity	NPC82053
0.8111	Intermediate Similarity	NPC42372
0.8085	Intermediate Similarity	NPC133003
0.8073	Intermediate Similarity	NPC188821
0.8073	Intermediate Similarity	NPC88315
0.8073	Intermediate Similarity	NPC474180
0.8011	Intermediate Similarity	NPC233050
0.8011	Intermediate Similarity	NPC276540
0.801	Intermediate Similarity	NPC324091
0.7966	Intermediate Similarity	NPC141926
0.7946	Intermediate Similarity	NPC293216
0.7926	Intermediate Similarity	NPC243381
0.7926	Intermediate Similarity	NPC191415
0.7926	Intermediate Similarity	NPC275292
0.7895	Intermediate Similarity	NPC99939
0.7895	Intermediate Similarity	NPC308931
0.7887	Intermediate Similarity	NPC267078
0.7887	Intermediate Similarity	NPC935
0.7887	Intermediate Similarity	NPC326422
0.7869	Intermediate Similarity	NPC114637
0.7857	Intermediate Similarity	NPC167710
0.785	Intermediate Similarity	NPC474357
0.784	Intermediate Similarity	NPC470323
0.7814	Intermediate Similarity	NPC233380
0.7814	Intermediate Similarity	NPC115232
0.7796	Intermediate Similarity	NPC477611
0.776	Intermediate Similarity	NPC274981
0.7737	Intermediate Similarity	NPC470677
0.7732	Intermediate Similarity	NPC154339
0.7725	Intermediate Similarity	NPC11126
0.7717	Intermediate Similarity	NPC2414
0.7717	Intermediate Similarity	NPC17751
0.7716	Intermediate Similarity	NPC79356
0.7716	Intermediate Similarity	NPC102592
0.7713	Intermediate Similarity	NPC151635
0.7696	Intermediate Similarity	NPC102755
0.7692	Intermediate Similarity	NPC474492
0.7688	Intermediate Similarity	NPC471943
0.7677	Intermediate Similarity	NPC262898
0.7667	Intermediate Similarity	NPC474195
0.766	Intermediate Similarity	NPC469529
0.7656	Intermediate Similarity	NPC228835
0.7656	Intermediate Similarity	NPC475736
0.7626	Intermediate Similarity	NPC179701
0.7619	Intermediate Similarity	NPC474958
0.7614	Intermediate Similarity	NPC267343
0.7609	Intermediate Similarity	NPC242116
0.7609	Intermediate Similarity	NPC214106
0.7606	Intermediate Similarity	NPC474196
0.7598	Intermediate Similarity	NPC2272
0.7585	Intermediate Similarity	NPC471194
0.7585	Intermediate Similarity	NPC471193
0.7585	Intermediate Similarity	NPC207020
0.7568	Intermediate Similarity	NPC149265
0.7563	Intermediate Similarity	NPC47190
0.7554	Intermediate Similarity	NPC470680
0.7554	Intermediate Similarity	NPC100104
0.7553	Intermediate Similarity	NPC82331
0.7539	Intermediate Similarity	NPC55772
0.7538	Intermediate Similarity	NPC17059
0.7538	Intermediate Similarity	NPC278434
0.7536	Intermediate Similarity	NPC72956
0.7527	Intermediate Similarity	NPC34844
0.7527	Intermediate Similarity	NPC274229
0.7513	Intermediate Similarity	NPC470205
0.7513	Intermediate Similarity	NPC252572
0.7513	Intermediate Similarity	NPC138370
0.75	Intermediate Similarity	NPC79777
0.75	Intermediate Similarity	NPC473666
0.75	Intermediate Similarity	NPC16659
0.75	Intermediate Similarity	NPC6865
0.75	Intermediate Similarity	NPC153980
0.7487	Intermediate Similarity	NPC14113
0.7487	Intermediate Similarity	NPC135601
0.7487	Intermediate Similarity	NPC94752
0.7487	Intermediate Similarity	NPC141612
0.7487	Intermediate Similarity	NPC145885
0.7487	Intermediate Similarity	NPC17273
0.7487	Intermediate Similarity	NPC84827
0.7486	Intermediate Similarity	NPC74357
0.7475	Intermediate Similarity	NPC473342
0.7475	Intermediate Similarity	NPC304187
0.7475	Intermediate Similarity	NPC477166
0.7475	Intermediate Similarity	NPC477167
0.7474	Intermediate Similarity	NPC21429
0.7473	Intermediate Similarity	NPC251391
0.7461	Intermediate Similarity	NPC307191
0.7448	Intermediate Similarity	NPC265710
0.7432	Intermediate Similarity	NPC37152
0.7426	Intermediate Similarity	NPC136957
0.7426	Intermediate Similarity	NPC19696
0.7423	Intermediate Similarity	NPC117027
0.7421	Intermediate Similarity	NPC161861
0.7415	Intermediate Similarity	NPC88115
0.7413	Intermediate Similarity	NPC475286
0.7413	Intermediate Similarity	NPC174281
0.7413	Intermediate Similarity	NPC227582
0.7409	Intermediate Similarity	NPC234403
0.7409	Intermediate Similarity	NPC477042
0.74	Intermediate Similarity	NPC202812
0.7397	Intermediate Similarity	NPC63031
0.7396	Intermediate Similarity	NPC240088
0.7396	Intermediate Similarity	NPC111275
0.7396	Intermediate Similarity	NPC473380
0.7393	Intermediate Similarity	NPC471192
0.7391	Intermediate Similarity	NPC116555
0.7389	Intermediate Similarity	NPC316069
0.7387	Intermediate Similarity	NPC216550
0.7382	Intermediate Similarity	NPC149155
0.7382	Intermediate Similarity	NPC280297
0.7382	Intermediate Similarity	NPC203468
0.7382	Intermediate Similarity	NPC110500
0.738	Intermediate Similarity	NPC265100
0.7377	Intermediate Similarity	NPC200214
0.7363	Intermediate Similarity	NPC471655
0.7363	Intermediate Similarity	NPC472293
0.7358	Intermediate Similarity	NPC126709
0.7358	Intermediate Similarity	NPC248041
0.7358	Intermediate Similarity	NPC283219
0.7354	Intermediate Similarity	NPC78020
0.7353	Intermediate Similarity	NPC471944
0.7344	Intermediate Similarity	NPC267885
0.734	Intermediate Similarity	NPC74413
0.734	Intermediate Similarity	NPC280864
0.7333	Intermediate Similarity	NPC314372
0.733	Intermediate Similarity	NPC105127
0.732	Intermediate Similarity	NPC88110
0.7318	Intermediate Similarity	NPC190296
0.7318	Intermediate Similarity	NPC200553
0.7318	Intermediate Similarity	NPC279189
0.7317	Intermediate Similarity	NPC106757
0.7313	Intermediate Similarity	NPC195239
0.7313	Intermediate Similarity	NPC294693
0.7313	Intermediate Similarity	NPC157828
0.731	Intermediate Similarity	NPC235684
0.7308	Intermediate Similarity	NPC123906
0.7304	Intermediate Similarity	NPC252338
0.7303	Intermediate Similarity	NPC469780
0.7303	Intermediate Similarity	NPC469783
0.7303	Intermediate Similarity	NPC469768
0.7303	Intermediate Similarity	NPC469767
0.7303	Intermediate Similarity	NPC469784
0.7303	Intermediate Similarity	NPC469779
0.7303	Intermediate Similarity	NPC469761
0.73	Intermediate Similarity	NPC472292
0.7291	Intermediate Similarity	NPC131887
0.7287	Intermediate Similarity	NPC21174
0.7287	Intermediate Similarity	NPC271797
0.7277	Intermediate Similarity	NPC476526
0.7277	Intermediate Similarity	NPC11445
0.7277	Intermediate Similarity	NPC329765
0.7277	Intermediate Similarity	NPC267811
0.7277	Intermediate Similarity	NPC48117
0.7277	Intermediate Similarity	NPC262338
0.7273	Intermediate Similarity	NPC96102
0.7268	Intermediate Similarity	NPC24678
0.7268	Intermediate Similarity	NPC105818
0.7263	Intermediate Similarity	NPC70949
0.7263	Intermediate Similarity	NPC469766
0.7255	Intermediate Similarity	NPC472297
0.7255	Intermediate Similarity	NPC472296
0.7253	Intermediate Similarity	NPC105811
0.7252	Intermediate Similarity	NPC174489
0.7247	Intermediate Similarity	NPC73767
0.7247	Intermediate Similarity	NPC110126
0.7238	Intermediate Similarity	NPC467188
0.7238	Intermediate Similarity	NPC159856
0.7236	Intermediate Similarity	NPC213629
0.7236	Intermediate Similarity	NPC321708
0.7233	Intermediate Similarity	NPC260900
0.7232	Intermediate Similarity	NPC84911
0.7231	Intermediate Similarity	NPC73994
0.7228	Intermediate Similarity	NPC70406
0.722	Intermediate Similarity	NPC205254
0.722	Intermediate Similarity	NPC303820
0.722	Intermediate Similarity	NPC23420
0.722	Intermediate Similarity	NPC106771
0.722	Intermediate Similarity	NPC162002
0.7216	Intermediate Similarity	NPC157583

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 NPC477004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	712
0.2-0.3	1192
0.3-0.4	2478
0.4-0.5	2396
0.5-0.6	1584
0.6-0.7	498
0.7-0.8	41
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
0.7937	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD4848	Phase 1
0.7876	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4922	Phase 2
0.7604	Intermediate Similarity	NPD3319	Phase 1
0.7604	Intermediate Similarity	NPD3320	Approved
0.7604	Intermediate Similarity	NPD3318	Approved
0.7576	Intermediate Similarity	NPD7618	Phase 3
0.7576	Intermediate Similarity	NPD7619	Phase 3
0.7563	Intermediate Similarity	NPD7098	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD2008	Discontinued
0.75	Intermediate Similarity	NPD2481	Approved
0.75	Intermediate Similarity	NPD6664	Approved
0.75	Intermediate Similarity	NPD2479	Phase 3
0.7474	Intermediate Similarity	NPD7564	Discontinued
0.7449	Intermediate Similarity	NPD4988	Discontinued
0.7435	Intermediate Similarity	NPD4075	Phase 2
0.7415	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD1284	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2442	Approved
0.7391	Intermediate Similarity	NPD2443	Approved
0.7389	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2091	Phase 2
0.7385	Intermediate Similarity	NPD2096	Phase 2
0.7382	Intermediate Similarity	NPD482	Approved
0.7366	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD2290	Phase 3
0.7363	Intermediate Similarity	NPD2289	Phase 3
0.7344	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2411	Approved
0.7333	Intermediate Similarity	NPD2094	Phase 2
0.7333	Intermediate Similarity	NPD2092	Phase 2
0.7333	Intermediate Similarity	NPD2095	Phase 2
0.7321	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5473	Discontinued
0.7311	Intermediate Similarity	NPD3394	Approved
0.7311	Intermediate Similarity	NPD3389	Approved
0.7311	Intermediate Similarity	NPD3393	Approved
0.731	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2509	Approved
0.7308	Intermediate Similarity	NPD2510	Approved
0.7299	Intermediate Similarity	NPD6787	Phase 2
0.7277	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1996	Discontinued
0.7247	Intermediate Similarity	NPD786	Approved
0.7246	Intermediate Similarity	NPD3947	Discontinued
0.723	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2408	Discontinued
0.7173	Intermediate Similarity	NPD1343	Approved
0.7167	Intermediate Similarity	NPD1722	Approved
0.7163	Intermediate Similarity	NPD5901	Discontinued
0.7156	Intermediate Similarity	NPD4051	Discontinued
0.713	Intermediate Similarity	NPD5199	Approved
0.713	Intermediate Similarity	NPD5198	Approved
0.7123	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3961	Discontinued
0.7087	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD750	Phase 2
0.7039	Intermediate Similarity	NPD1982	Phase 1
0.7033	Intermediate Similarity	NPD6176	Phase 1
0.7028	Intermediate Similarity	NPD1600	Suspended
0.7027	Intermediate Similarity	NPD3100	Discontinued
0.7014	Intermediate Similarity	NPD1506	Discontinued
0.7014	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5426	Phase 3
0.699	Remote Similarity	NPD1952	Discontinued
0.6989	Remote Similarity	NPD2172	Phase 1
0.6981	Remote Similarity	NPD6459	Phase 2
0.6973	Remote Similarity	NPD1270	Approved
0.6965	Remote Similarity	NPD5809	Phase 3
0.6959	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5017	Discontinued
0.6938	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3178	Discontinued
0.6931	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7455	Approved
0.693	Remote Similarity	NPD7454	Approved
0.6927	Remote Similarity	NPD460	Discontinued
0.6927	Remote Similarity	NPD3583	Phase 2
0.6919	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6987	Phase 1
0.6919	Remote Similarity	NPD3079	Approved
0.6919	Remote Similarity	NPD3077	Approved
0.6919	Remote Similarity	NPD3076	Approved
0.6919	Remote Similarity	NPD3078	Approved
0.6915	Remote Similarity	NPD2837	Discontinued
0.6912	Remote Similarity	NPD1658	Discontinued
0.6907	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2881	Approved
0.6905	Remote Similarity	NPD2879	Approved
0.6893	Remote Similarity	NPD5855	Phase 3
0.6893	Remote Similarity	NPD5853	Phase 3
0.6888	Remote Similarity	NPD4524	Discontinued
0.6881	Remote Similarity	NPD6217	Discontinued
0.6868	Remote Similarity	NPD2071	Approved
0.6868	Remote Similarity	NPD2070	Approved
0.6868	Remote Similarity	NPD2069	Approved
0.6868	Remote Similarity	NPD2068	Approved
0.6866	Remote Similarity	NPD7970	Approved
0.6866	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2214	Approved
0.6859	Remote Similarity	NPD2213	Approved
0.6856	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4883	Approved
0.6853	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD200	Phase 2
0.6851	Remote Similarity	NPD201	Phase 2
0.684	Remote Similarity	NPD4299	Phase 1
0.6837	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD272	Approved
0.683	Remote Similarity	NPD4845	Discontinued
0.6827	Remote Similarity	NPD2880	Discontinued
0.6823	Remote Similarity	NPD1404	Approved
0.6823	Remote Similarity	NPD1403	Approved
0.682	Remote Similarity	NPD5888	Phase 2
0.6806	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7470	Discontinued
0.6798	Remote Similarity	NPD7026	Phase 2
0.6789	Remote Similarity	NPD2061	Approved
0.6788	Remote Similarity	NPD5400	Approved
0.6787	Remote Similarity	NPD6242	Discontinued
0.6776	Remote Similarity	NPD3905	Phase 3
0.6774	Remote Similarity	NPD8093	Discontinued
0.6772	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1630	Approved
0.6769	Remote Similarity	NPD2639	Approved
0.6769	Remote Similarity	NPD2642	Approved
0.6768	Remote Similarity	NPD5065	Approved
0.6763	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6999	Discontinued
0.6762	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8272	Phase 2
0.6749	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2336	Approved
0.6745	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8094	Discontinued
0.6735	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD2641	Approved
0.6735	Remote Similarity	NPD2640	Approved
0.6731	Remote Similarity	NPD7944	Discontinued
0.673	Remote Similarity	NPD484	Approved
0.6728	Remote Similarity	NPD6152	Phase 1
0.6728	Remote Similarity	NPD5475	Discontinued
0.672	Remote Similarity	NPD4463	Approved
0.672	Remote Similarity	NPD4462	Approved
0.6718	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6595	Phase 3
0.6716	Remote Similarity	NPD1618	Phase 2
0.6716	Remote Similarity	NPD3927	Phase 2
0.6715	Remote Similarity	NPD5505	Discontinued
0.6714	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1575	Approved
0.6701	Remote Similarity	NPD1573	Approved
0.6701	Remote Similarity	NPD6771	Discontinued
0.67	Remote Similarity	NPD3506	Approved
0.67	Remote Similarity	NPD3505	Approved
0.67	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.67	Remote Similarity	NPD2144	Approved
0.67	Remote Similarity	NPD2753	Discontinued
0.6699	Remote Similarity	NPD6226	Phase 3
0.6697	Remote Similarity	NPD7657	Approved
0.6697	Remote Similarity	NPD7656	Approved
0.6697	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4128	Approved
0.6682	Remote Similarity	NPD5854	Approved
0.6682	Remote Similarity	NPD2405	Phase 3
0.6681	Remote Similarity	NPD6164	Phase 2
0.6681	Remote Similarity	NPD6165	Phase 2
0.6667	Remote Similarity	NPD1183	Approved
0.6667	Remote Similarity	NPD4079	Approved
0.6667	Remote Similarity	NPD4076	Approved
0.6667	Remote Similarity	NPD1631	Approved
0.6667	Remote Similarity	NPD3323	Discontinued
0.6667	Remote Similarity	NPD5446	Phase 2
0.6652	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5491	Phase 3
0.6651	Remote Similarity	NPD5489	Phase 1
0.6651	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3967	Approved
0.6651	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7001	Phase 3
0.665	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6044	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