NPASS Compound

Structure

CID216369 OpenBabel06191716002D 26 28 0 0 1 0 0 0 0 0999 V2000 3.6036 -1.4986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3164 -0.3397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 -2.2418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -1.0828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9637 0.1956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 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 3.2946 -0.5476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 -2.0339 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 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6547 1.1466 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3238 1.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.6765 1.3545 0.0000 N 0 0 0 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 -3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3019 1.6819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0148 2.8408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 9 2 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 13 1 0 0 0 0 7 15 2 0 0 0 0 8 12 2 0 0 0 0 8 21 1 0 0 0 0 10 26 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 20 1 6 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.02
Volume:	355.715
LogP:	0.741
LogD:	2.348
LogS:	-3.846
# Rotatable Bonds:	6
TPSA:	125.64
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	2.833
Fsp3:	0.111
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:	-5.24
MDCK Permeability:	8.530265404260717e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	97.91522216796875%
Volume Distribution (VD):	0.268
Pgp-substrate:	1.497226357460022%

ADMET: Metabolism

CYP1A2-inhibitor:	0.621
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.221
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.379
CYP2C9-substrate:	0.525
CYP2D6-inhibitor:	0.667
CYP2D6-substrate:	0.346
CYP3A4-inhibitor:	0.24
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	5.737
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.245
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.466
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.667
Carcinogencity:	0.137
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.166

Download Data

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

Natural Product: NPC216369

Natural Product ID:	NPC216369
*Common Name:**	Herdmanine D
IUPAC Name:	(2S)-2-amino-3-[4-(6-bromo-5-hydroxy-1H-indole-3-carbonyl)oxyphenyl]propanoic acid
Synonyms:	Herdmanine D
Standard InCHIKey:	PKFPVOPFIFUXPW-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C18H15BrN2O5/c19-13-7-15-11(6-16(13)22)12(8-21-15)18(25)26-10-3-1-9(2-4-10)5-14(20)17(23)24/h1-4,6-8,14,21-22H,5,20H2,(H,23,24)/t14-/m0/s1
SMILES:	c1cc(ccc1C[C@@H](C(=O)O)N)OC(=O)c1c[nH]c2cc(c(cc12)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915724
PubChem CID:	53483957
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004321] Phenylalanine 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
NPO7505	Herdmania momus	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21770369]
NPO7505	Herdmania momus	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23189988]
NPO7505	Herdmania momus	Species	Pyuridae	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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9000.0	nM	PMID[476627]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	170000.0	nM	PMID[476627]

☑ 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 NPC216369 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	599
0.1-0.2	4027
0.2-0.3	13014
0.3-0.4	4865
0.4-0.5	15329
0.5-0.6	2953
0.6-0.7	1706
0.7-0.8	201
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8421	Intermediate Similarity	NPC74360
0.7991	Intermediate Similarity	NPC276657
0.7967	Intermediate Similarity	NPC97902
0.791	Intermediate Similarity	NPC37152
0.7895	Intermediate Similarity	NPC82053
0.7884	Intermediate Similarity	NPC200553
0.7826	Intermediate Similarity	NPC171787
0.7787	Intermediate Similarity	NPC162002
0.7783	Intermediate Similarity	NPC193238
0.7768	Intermediate Similarity	NPC219087
0.7753	Intermediate Similarity	NPC315491
0.7753	Intermediate Similarity	NPC45459
0.7746	Intermediate Similarity	NPC174489
0.7738	Intermediate Similarity	NPC471536
0.7737	Intermediate Similarity	NPC279189
0.7711	Intermediate Similarity	NPC78609
0.7692	Intermediate Similarity	NPC207020
0.7683	Intermediate Similarity	NPC26641
0.7683	Intermediate Similarity	NPC15801
0.7673	Intermediate Similarity	NPC182222
0.7664	Intermediate Similarity	NPC207686
0.7655	Intermediate Similarity	NPC222018
0.7602	Intermediate Similarity	NPC245055
0.7598	Intermediate Similarity	NPC213308
0.7595	Intermediate Similarity	NPC74969
0.759	Intermediate Similarity	NPC148889
0.7585	Intermediate Similarity	NPC477610
0.7551	Intermediate Similarity	NPC260434
0.754	Intermediate Similarity	NPC178858
0.7511	Intermediate Similarity	NPC266931
0.749	Intermediate Similarity	NPC27041
0.749	Intermediate Similarity	NPC284888
0.748	Intermediate Similarity	NPC91868
0.748	Intermediate Similarity	NPC63971
0.7479	Intermediate Similarity	NPC183777
0.747	Intermediate Similarity	NPC235685
0.7467	Intermediate Similarity	NPC156704
0.746	Intermediate Similarity	NPC33064
0.7459	Intermediate Similarity	NPC24370
0.7459	Intermediate Similarity	NPC319232
0.7458	Intermediate Similarity	NPC477609
0.7449	Intermediate Similarity	NPC474192
0.7449	Intermediate Similarity	NPC475720
0.7449	Intermediate Similarity	NPC122436
0.7449	Intermediate Similarity	NPC54803
0.7449	Intermediate Similarity	NPC321592
0.7445	Intermediate Similarity	NPC99666
0.744	Intermediate Similarity	NPC101350
0.7439	Intermediate Similarity	NPC223409
0.7438	Intermediate Similarity	NPC60621
0.7429	Intermediate Similarity	NPC304307
0.7429	Intermediate Similarity	NPC34580
0.7429	Intermediate Similarity	NPC124920
0.7429	Intermediate Similarity	NPC118559
0.7422	Intermediate Similarity	NPC181081
0.7413	Intermediate Similarity	NPC258048
0.7407	Intermediate Similarity	NPC243633
0.7407	Intermediate Similarity	NPC175150
0.7404	Intermediate Similarity	NPC321428
0.7398	Intermediate Similarity	NPC100547
0.7379	Intermediate Similarity	NPC196718
0.7371	Intermediate Similarity	NPC82472
0.7368	Intermediate Similarity	NPC95240
0.7368	Intermediate Similarity	NPC322135
0.7362	Intermediate Similarity	NPC208522
0.7362	Intermediate Similarity	NPC300156
0.736	Intermediate Similarity	NPC272549
0.7358	Intermediate Similarity	NPC261251
0.7353	Intermediate Similarity	NPC87413
0.7345	Intermediate Similarity	NPC278434
0.7343	Intermediate Similarity	NPC196449
0.7343	Intermediate Similarity	NPC314222
0.7339	Intermediate Similarity	NPC14288
0.7336	Intermediate Similarity	NPC307963
0.7331	Intermediate Similarity	NPC88008
0.7325	Intermediate Similarity	NPC138370
0.7317	Intermediate Similarity	NPC214142
0.7314	Intermediate Similarity	NPC264285
0.7313	Intermediate Similarity	NPC77101
0.7311	Intermediate Similarity	NPC309845
0.7309	Intermediate Similarity	NPC102593
0.7304	Intermediate Similarity	NPC276517
0.7291	Intermediate Similarity	NPC477549
0.7287	Intermediate Similarity	NPC478078
0.7284	Intermediate Similarity	NPC168209
0.728	Intermediate Similarity	NPC323752
0.7273	Intermediate Similarity	NPC251090
0.7273	Intermediate Similarity	NPC475816
0.7241	Intermediate Similarity	NPC90229
0.7237	Intermediate Similarity	NPC161801
0.7237	Intermediate Similarity	NPC296527
0.7227	Intermediate Similarity	NPC39679
0.7224	Intermediate Similarity	NPC280799
0.7214	Intermediate Similarity	NPC475746
0.7208	Intermediate Similarity	NPC132385
0.7208	Intermediate Similarity	NPC246518
0.7206	Intermediate Similarity	NPC125597
0.7205	Intermediate Similarity	NPC76748
0.7203	Intermediate Similarity	NPC476098
0.7195	Intermediate Similarity	NPC16352
0.7194	Intermediate Similarity	NPC6786
0.7189	Intermediate Similarity	NPC477608
0.7189	Intermediate Similarity	NPC477607
0.7186	Intermediate Similarity	NPC88315
0.7185	Intermediate Similarity	NPC4687
0.7184	Intermediate Similarity	NPC174760
0.7184	Intermediate Similarity	NPC472099
0.7181	Intermediate Similarity	NPC165964
0.7181	Intermediate Similarity	NPC314002
0.7179	Intermediate Similarity	NPC280714
0.7178	Intermediate Similarity	NPC316981
0.7176	Intermediate Similarity	NPC53534
0.7176	Intermediate Similarity	NPC210296
0.7174	Intermediate Similarity	NPC92111
0.7172	Intermediate Similarity	NPC96321
0.7172	Intermediate Similarity	NPC184408
0.7171	Intermediate Similarity	NPC49547
0.7168	Intermediate Similarity	NPC220765
0.7167	Intermediate Similarity	NPC77555
0.7154	Intermediate Similarity	NPC473317
0.7153	Intermediate Similarity	NPC116701
0.7149	Intermediate Similarity	NPC157931
0.7149	Intermediate Similarity	NPC74575
0.7143	Intermediate Similarity	NPC476121
0.7143	Intermediate Similarity	NPC45190
0.7143	Intermediate Similarity	NPC473105
0.7137	Intermediate Similarity	NPC204717
0.7137	Intermediate Similarity	NPC21638
0.7137	Intermediate Similarity	NPC245348
0.7126	Intermediate Similarity	NPC470501
0.7123	Intermediate Similarity	NPC9482
0.7121	Intermediate Similarity	NPC74619
0.712	Intermediate Similarity	NPC274640
0.7113	Intermediate Similarity	NPC270918
0.7108	Intermediate Similarity	NPC60006
0.7107	Intermediate Similarity	NPC110182
0.7107	Intermediate Similarity	NPC128084
0.7097	Intermediate Similarity	NPC229893
0.7092	Intermediate Similarity	NPC326363
0.709	Intermediate Similarity	NPC67658
0.709	Intermediate Similarity	NPC142901
0.709	Intermediate Similarity	NPC469928
0.7085	Intermediate Similarity	NPC470502
0.7079	Intermediate Similarity	NPC152620
0.7078	Intermediate Similarity	NPC476287
0.7074	Intermediate Similarity	NPC171171
0.7068	Intermediate Similarity	NPC179287
0.7066	Intermediate Similarity	NPC82370
0.7064	Intermediate Similarity	NPC306376
0.7063	Intermediate Similarity	NPC474701
0.7061	Intermediate Similarity	NPC169402
0.7052	Intermediate Similarity	NPC246381
0.7052	Intermediate Similarity	NPC194740
0.7049	Intermediate Similarity	NPC118228
0.7045	Intermediate Similarity	NPC54066
0.7045	Intermediate Similarity	NPC478083
0.7045	Intermediate Similarity	NPC150239
0.7043	Intermediate Similarity	NPC475844
0.7043	Intermediate Similarity	NPC46580
0.7042	Intermediate Similarity	NPC207620
0.7033	Intermediate Similarity	NPC247803
0.7033	Intermediate Similarity	NPC46561
0.7028	Intermediate Similarity	NPC470503
0.7028	Intermediate Similarity	NPC51388
0.7025	Intermediate Similarity	NPC470020
0.7025	Intermediate Similarity	NPC471304
0.7025	Intermediate Similarity	NPC11464
0.7025	Intermediate Similarity	NPC123839
0.702	Intermediate Similarity	NPC473187
0.702	Intermediate Similarity	NPC3207
0.7012	Intermediate Similarity	NPC266249
0.7011	Intermediate Similarity	NPC270515
0.7008	Intermediate Similarity	NPC236668
0.7008	Intermediate Similarity	NPC39500
0.7008	Intermediate Similarity	NPC303374
0.7004	Intermediate Similarity	NPC213530
0.7004	Intermediate Similarity	NPC176538
0.7004	Intermediate Similarity	NPC193267
0.7	Intermediate Similarity	NPC476124
0.6996	Remote Similarity	NPC474688
0.6992	Remote Similarity	NPC67288
0.6991	Remote Similarity	NPC184964
0.6988	Remote Similarity	NPC144452
0.6984	Remote Similarity	NPC471762
0.6984	Remote Similarity	NPC66777
0.6984	Remote Similarity	NPC311906
0.6983	Remote Similarity	NPC325297
0.698	Remote Similarity	NPC146976
0.698	Remote Similarity	NPC325976
0.698	Remote Similarity	NPC50562
0.698	Remote Similarity	NPC116238
0.6979	Remote Similarity	NPC179701
0.6976	Remote Similarity	NPC323969
0.6974	Remote Similarity	NPC117980
0.6972	Remote Similarity	NPC470018
0.6971	Remote Similarity	NPC249583
0.697	Remote Similarity	NPC329982
0.6966	Remote Similarity	NPC191489
0.6964	Remote Similarity	NPC473041
0.6962	Remote Similarity	NPC477004

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 NPC216369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	688
0.2-0.3	1046
0.3-0.4	1749
0.4-0.5	2814
0.5-0.6	1910
0.6-0.7	599
0.7-0.8	53
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
0.7821	Intermediate Similarity	NPD5612	Discontinued
0.7787	Intermediate Similarity	NPD3006	Discontinued
0.7764	Intermediate Similarity	NPD6242	Discontinued
0.7753	Intermediate Similarity	NPD484	Approved
0.7686	Intermediate Similarity	NPD5050	Approved
0.764	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4845	Discontinued
0.7451	Intermediate Similarity	NPD5482	Discontinued
0.7439	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7994	Phase 2
0.7353	Intermediate Similarity	NPD5416	Discontinued
0.735	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD1038	Approved
0.7314	Intermediate Similarity	NPD5632	Approved
0.73	Intermediate Similarity	NPD2510	Approved
0.73	Intermediate Similarity	NPD2509	Approved
0.729	Intermediate Similarity	NPD6530	Approved
0.729	Intermediate Similarity	NPD6531	Approved
0.728	Intermediate Similarity	NPD4373	Phase 2
0.7231	Intermediate Similarity	NPD3394	Approved
0.7231	Intermediate Similarity	NPD3393	Approved
0.7231	Intermediate Similarity	NPD3389	Approved
0.7229	Intermediate Similarity	NPD4952	Phase 3
0.7229	Intermediate Similarity	NPD4418	Discontinued
0.7222	Intermediate Similarity	NPD7853	Phase 2
0.7214	Intermediate Similarity	NPD8091	Phase 3
0.719	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7417	Discontinued
0.7172	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3354	Phase 2
0.7167	Intermediate Similarity	NPD7948	Phase 1
0.716	Intermediate Similarity	NPD5022	Discontinued
0.7149	Intermediate Similarity	NPD3259	Approved
0.7116	Intermediate Similarity	NPD5450	Discontinued
0.7114	Intermediate Similarity	NPD1996	Discontinued
0.7108	Intermediate Similarity	NPD3263	Phase 3
0.7106	Intermediate Similarity	NPD3825	Phase 3
0.7102	Intermediate Similarity	NPD4429	Discontinued
0.7101	Intermediate Similarity	NPD5901	Discontinued
0.708	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7558	Phase 2
0.7071	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6962	Phase 2
0.7061	Intermediate Similarity	NPD2091	Phase 2
0.7061	Intermediate Similarity	NPD2096	Phase 2
0.7037	Intermediate Similarity	NPD7069	Discontinued
0.7033	Intermediate Similarity	NPD7395	Discontinued
0.7028	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5891	Approved
0.7018	Intermediate Similarity	NPD2094	Phase 2
0.7018	Intermediate Similarity	NPD2095	Phase 2
0.7018	Intermediate Similarity	NPD2092	Phase 2
0.7016	Intermediate Similarity	NPD1483	Discontinued
0.6996	Remote Similarity	NPD7470	Discontinued
0.6988	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5559	Phase 2
0.697	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7708	Approved
0.6953	Remote Similarity	NPD4454	Phase 2
0.695	Remote Similarity	NPD6716	Phase 1
0.6941	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6494	Phase 2
0.6936	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3258	Approved
0.6926	Remote Similarity	NPD7803	Approved
0.6926	Remote Similarity	NPD5066	Phase 2
0.6926	Remote Similarity	NPD5067	Phase 2
0.6923	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6790	Phase 1
0.6911	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8463	Approved
0.6905	Remote Similarity	NPD7603	Discontinued
0.6901	Remote Similarity	NPD7222	Phase 2
0.6901	Remote Similarity	NPD1392	Approved
0.6901	Remote Similarity	NPD7453	Approved
0.6901	Remote Similarity	NPD7452	Approved
0.6898	Remote Similarity	NPD5866	Approved
0.6882	Remote Similarity	NPD4558	Phase 2
0.6875	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3003	Approved
0.686	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD8101	Phase 3
0.6848	Remote Similarity	NPD6964	Approved
0.6848	Remote Similarity	NPD6963	Approved
0.6844	Remote Similarity	NPD6276	Discontinued
0.6842	Remote Similarity	NPD3257	Approved
0.6842	Remote Similarity	NPD5293	Phase 2
0.6835	Remote Similarity	NPD5512	Phase 3
0.6828	Remote Similarity	NPD482	Approved
0.6824	Remote Similarity	NPD4948	Discontinued
0.6818	Remote Similarity	NPD3947	Discontinued
0.6813	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4889	Approved
0.6803	Remote Similarity	NPD2187	Approved
0.6803	Remote Similarity	NPD2189	Approved
0.6802	Remote Similarity	NPD3794	Approved
0.6802	Remote Similarity	NPD3795	Approved
0.6789	Remote Similarity	NPD5475	Discontinued
0.6787	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6228	Discontinued
0.6761	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD8102	Discontinued
0.6749	Remote Similarity	NPD4036	Approved
0.6749	Remote Similarity	NPD4035	Approved
0.6749	Remote Similarity	NPD4122	Approved
0.6749	Remote Similarity	NPD4034	Approved
0.6749	Remote Similarity	NPD4038	Approved
0.6749	Remote Similarity	NPD4037	Approved
0.6749	Remote Similarity	NPD31	Approved
0.6749	Remote Similarity	NPD32	Approved
0.6749	Remote Similarity	NPD4039	Approved
0.6749	Remote Similarity	NPD4033	Approved
0.6748	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD4328	Approved
0.6742	Remote Similarity	NPD8100	Phase 3
0.6741	Remote Similarity	NPD7956	Approved
0.6741	Remote Similarity	NPD7955	Approved
0.6739	Remote Similarity	NPD7689	Approved
0.6735	Remote Similarity	NPD5658	Approved
0.6734	Remote Similarity	NPD3243	Approved
0.6734	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1505	Phase 2
0.6725	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4989	Phase 2
0.672	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4885	Approved
0.6693	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6517	Phase 3
0.668	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.668	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4850	Phase 1
0.6679	Remote Similarity	NPD7859	Phase 2
0.6667	Remote Similarity	NPD6770	Approved
0.6667	Remote Similarity	NPD4890	Phase 2
0.6667	Remote Similarity	NPD2779	Approved
0.6654	Remote Similarity	NPD2951	Discontinued
0.6654	Remote Similarity	NPD8358	Approved
0.6653	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD4502	Phase 2
0.6643	Remote Similarity	NPD6153	Approved
0.664	Remote Similarity	NPD5903	Approved
0.664	Remote Similarity	NPD5902	Approved
0.664	Remote Similarity	NPD7180	Phase 3
0.6639	Remote Similarity	NPD6569	Phase 2
0.6639	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5051	Phase 1
0.6629	Remote Similarity	NPD3322	Phase 1
0.6626	Remote Similarity	NPD5429	Discontinued
0.6616	Remote Similarity	NPD7886	Phase 2
0.6616	Remote Similarity	NPD7885	Phase 2
0.6612	Remote Similarity	NPD4795	Phase 2
0.6612	Remote Similarity	NPD1768	Approved
0.6611	Remote Similarity	NPD4551	Phase 2
0.6609	Remote Similarity	NPD3178	Discontinued
0.6601	Remote Similarity	NPD6974	Phase 3
0.66	Remote Similarity	NPD3945	Discontinued
0.6599	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5003	Discontinued
0.6596	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5601	Phase 2
0.6584	Remote Similarity	NPD1739	Approved
0.6584	Remote Similarity	NPD1740	Approved
0.6584	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3280	Approved
0.6573	Remote Similarity	NPD4506	Discontinued
0.6571	Remote Similarity	NPD6176	Phase 1
0.657	Remote Similarity	NPD7924	Phase 2
0.657	Remote Similarity	NPD7925	Phase 2
0.6569	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5469	Phase 3
0.6565	Remote Similarity	NPD750	Phase 2
0.6564	Remote Similarity	NPD5479	Discontinued
0.6561	Remote Similarity	NPD7878	Phase 2
0.6554	Remote Similarity	NPD5488	Discontinued
0.6553	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2778	Approved
0.654	Remote Similarity	NPD5805	Approved
0.6538	Remote Similarity	NPD1867	Approved
0.6537	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5116	Phase 1
0.6531	Remote Similarity	NPD8073	Approved
0.6529	Remote Similarity	NPD2952	Discontinued
0.6525	Remote Similarity	NPD3217	Phase 2
0.652	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4350	Approved
0.6517	Remote Similarity	NPD3959	Phase 2
0.6517	Remote Similarity	NPD3962	Phase 2
0.6517	Remote Similarity	NPD4349	Approved
0.6513	Remote Similarity	NPD5015	Clinical (unspecified phase)

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