NPASS Compound

Structure

NPC355 OpenBabel07101718182D 31 35 0 0 1 0 0 0 0 0999 V2000 3.7089 2.0135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8990 -2.8122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2312 2.3035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3176 1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1211 1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3173 -1.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7512 -0.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3201 -1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1878 0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -1.3090 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 1.2298 -2.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1266 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7568 1.4010 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.1180 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 0.2517 -2.2770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5593 2.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5593 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 15 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 13 19 2 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 15 29 2 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 14 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 22 28 1 0 0 0 0 22 31 2 0 0 0 0 23 25 1 1 0 0 0 23 27 1 0 0 0 0 23 28 1 0 0 0 0 25 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	415.19
Volume:	431.17
LogP:	3.309
LogD:	2.929
LogS:	-5.383
# Rotatable Bonds:	3
TPSA:	69.72
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.761
Synthetic Accessibility Score:	3.965
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.89
MDCK Permeability:	3.4211232559755445e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.451

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	90.1595458984375%
Volume Distribution (VD):	0.457
Pgp-substrate:	9.438897132873535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.914
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.878
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.211
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.93

ADMET: Excretion

Clearance (CL):	2.029
Half-life (T1/2):	0.308

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.899
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.313
Maximum Recommended Daily Dose:	0.095
Skin Sensitization:	0.799
Carcinogencity:	0.11
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC355

Natural Product ID:	NPC355
*Common Name:**	Acyl Aszonalenin
IUPAC Name:	n.a.
Synonyms:	Acyl Aszonalenin
Standard InCHIKey:	TXNJQKDZOVFCAQ-GRYUFTJMSA-N
Standard InCHI:	InChI=1S/C25H25N3O3/c1-5-24(3,4)25-14-20-21(30)26-18-12-8-6-10-16(18)22(31)28(20)23(25)27(15(2)29)19-13-9-7-11-17(19)25/h5-13,20,23H,1,14H2,2-4H3,(H,26,30)/t20-,23-,25+/m0/s1
SMILES:	C=CC(C)(C)[C@]12C[C@H]3C(=Nc4ccccc4C(=O)N3[C@@H]2N(C(=O)C)c2ccccc12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480101
PubChem CID:	44575660
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22329646]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31674782]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32568536]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7517439]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT297	Individual Protein	Neurokinin 1 receptor	Homo sapiens	Ki	=	170000.0	nM	PMID[525181]

☑ 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 NPC355 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	283
0.1-0.2	1460
0.2-0.3	9555
0.3-0.4	19679
0.4-0.5	7148
0.5-0.6	3574
0.6-0.7	895
0.7-0.8	98
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8436	Intermediate Similarity	NPC106118
0.8427	Intermediate Similarity	NPC471199
0.8312	Intermediate Similarity	NPC122553
0.8242	Intermediate Similarity	NPC68650
0.8054	Intermediate Similarity	NPC295548
0.8023	Intermediate Similarity	NPC470548
0.7968	Intermediate Similarity	NPC225400
0.7926	Intermediate Similarity	NPC471155
0.7926	Intermediate Similarity	NPC470786
0.7926	Intermediate Similarity	NPC472538
0.7884	Intermediate Similarity	NPC270241
0.7772	Intermediate Similarity	NPC472539
0.7772	Intermediate Similarity	NPC472540
0.7772	Intermediate Similarity	NPC470787
0.7765	Intermediate Similarity	NPC307396
0.773	Intermediate Similarity	NPC472541
0.773	Intermediate Similarity	NPC472542
0.765	Intermediate Similarity	NPC276430
0.7614	Intermediate Similarity	NPC248601
0.756	Intermediate Similarity	NPC117032
0.7544	Intermediate Similarity	NPC471122
0.75	Intermediate Similarity	NPC472102
0.75	Intermediate Similarity	NPC309531
0.7471	Intermediate Similarity	NPC471130
0.7471	Intermediate Similarity	NPC471124
0.7458	Intermediate Similarity	NPC177261
0.7457	Intermediate Similarity	NPC472120
0.7457	Intermediate Similarity	NPC472117
0.7457	Intermediate Similarity	NPC472101
0.7423	Intermediate Similarity	NPC315051
0.7387	Intermediate Similarity	NPC244425
0.7387	Intermediate Similarity	NPC15384
0.7374	Intermediate Similarity	NPC475607
0.7371	Intermediate Similarity	NPC472106
0.7362	Intermediate Similarity	NPC469560
0.736	Intermediate Similarity	NPC285622
0.7356	Intermediate Similarity	NPC88970
0.7346	Intermediate Similarity	NPC471123
0.7345	Intermediate Similarity	NPC472118
0.7333	Intermediate Similarity	NPC285192
0.7333	Intermediate Similarity	NPC474081
0.7318	Intermediate Similarity	NPC475594
0.73	Intermediate Similarity	NPC471197
0.7293	Intermediate Similarity	NPC475761
0.7284	Intermediate Similarity	NPC300299
0.7283	Intermediate Similarity	NPC113946
0.7264	Intermediate Similarity	NPC471198
0.7262	Intermediate Similarity	NPC324445
0.7232	Intermediate Similarity	NPC279527
0.7232	Intermediate Similarity	NPC214960
0.7225	Intermediate Similarity	NPC84317
0.7216	Intermediate Similarity	NPC189116
0.7205	Intermediate Similarity	NPC207428
0.7198	Intermediate Similarity	NPC475094
0.7198	Intermediate Similarity	NPC474041
0.7193	Intermediate Similarity	NPC66936
0.7184	Intermediate Similarity	NPC104345
0.7143	Intermediate Similarity	NPC471191
0.7143	Intermediate Similarity	NPC316746
0.7143	Intermediate Similarity	NPC154478
0.7143	Intermediate Similarity	NPC36495
0.7128	Intermediate Similarity	NPC471196
0.7128	Intermediate Similarity	NPC471195
0.7117	Intermediate Similarity	NPC162417
0.7117	Intermediate Similarity	NPC316104
0.7112	Intermediate Similarity	NPC473815
0.7108	Intermediate Similarity	NPC207554
0.7076	Intermediate Similarity	NPC300596
0.7076	Intermediate Similarity	NPC237649
0.7066	Intermediate Similarity	NPC471574
0.7059	Intermediate Similarity	NPC17273
0.7059	Intermediate Similarity	NPC135601
0.7059	Intermediate Similarity	NPC141612
0.7059	Intermediate Similarity	NPC473615
0.7049	Intermediate Similarity	NPC64436
0.7048	Intermediate Similarity	NPC83214
0.7045	Intermediate Similarity	NPC276085
0.7027	Intermediate Similarity	NPC270301
0.7021	Intermediate Similarity	NPC229484
0.7015	Intermediate Similarity	NPC153980
0.7015	Intermediate Similarity	NPC6865
0.7011	Intermediate Similarity	NPC295021
0.7006	Intermediate Similarity	NPC143457
0.7006	Intermediate Similarity	NPC225319
0.7005	Intermediate Similarity	NPC259626
0.6989	Remote Similarity	NPC222029
0.6984	Remote Similarity	NPC292675
0.6973	Remote Similarity	NPC91179
0.6965	Remote Similarity	NPC72956
0.6952	Remote Similarity	NPC2933
0.6941	Remote Similarity	NPC136002
0.6927	Remote Similarity	NPC138293
0.6927	Remote Similarity	NPC113056
0.6914	Remote Similarity	NPC209389
0.6911	Remote Similarity	NPC92803
0.691	Remote Similarity	NPC315368
0.6905	Remote Similarity	NPC130251
0.69	Remote Similarity	NPC71238
0.6898	Remote Similarity	NPC256288
0.6898	Remote Similarity	NPC159125
0.6893	Remote Similarity	NPC61013
0.6893	Remote Similarity	NPC153694
0.6893	Remote Similarity	NPC123241
0.6893	Remote Similarity	NPC211525
0.6885	Remote Similarity	NPC214626
0.6885	Remote Similarity	NPC139085
0.6885	Remote Similarity	NPC251212
0.6882	Remote Similarity	NPC11149
0.6879	Remote Similarity	NPC109787
0.6872	Remote Similarity	NPC293458
0.6872	Remote Similarity	NPC476231
0.6872	Remote Similarity	NPC286871
0.6871	Remote Similarity	NPC314431
0.6864	Remote Similarity	NPC301760
0.6864	Remote Similarity	NPC471164
0.6864	Remote Similarity	NPC316202
0.6854	Remote Similarity	NPC263709
0.6854	Remote Similarity	NPC148468
0.6854	Remote Similarity	NPC310403
0.6854	Remote Similarity	NPC97380
0.6854	Remote Similarity	NPC243673
0.6854	Remote Similarity	NPC63210
0.6854	Remote Similarity	NPC193410
0.6847	Remote Similarity	NPC471193
0.6847	Remote Similarity	NPC471194
0.6836	Remote Similarity	NPC29285
0.6829	Remote Similarity	NPC471192
0.6828	Remote Similarity	NPC248462
0.6826	Remote Similarity	NPC267508
0.6818	Remote Similarity	NPC471436
0.6816	Remote Similarity	NPC248117
0.6806	Remote Similarity	NPC18890
0.68	Remote Similarity	NPC154602
0.6798	Remote Similarity	NPC54981
0.6796	Remote Similarity	NPC470069
0.6796	Remote Similarity	NPC52059
0.6793	Remote Similarity	NPC96901
0.6792	Remote Similarity	NPC257490
0.6791	Remote Similarity	NPC39822
0.6784	Remote Similarity	NPC314287
0.6779	Remote Similarity	NPC272174
0.6778	Remote Similarity	NPC282339
0.6778	Remote Similarity	NPC99632
0.6772	Remote Similarity	NPC245741
0.6772	Remote Similarity	NPC177684
0.6772	Remote Similarity	NPC291962
0.6765	Remote Similarity	NPC186284
0.6765	Remote Similarity	NPC22082
0.6761	Remote Similarity	NPC285381
0.6757	Remote Similarity	NPC13367
0.6746	Remote Similarity	NPC474896
0.6743	Remote Similarity	NPC473329
0.674	Remote Similarity	NPC313757
0.673	Remote Similarity	NPC161956
0.673	Remote Similarity	NPC258531
0.673	Remote Similarity	NPC112373
0.6728	Remote Similarity	NPC474926
0.6724	Remote Similarity	NPC212799
0.6723	Remote Similarity	NPC469903
0.6722	Remote Similarity	NPC474058
0.6722	Remote Similarity	NPC201424
0.6721	Remote Similarity	NPC224970
0.6721	Remote Similarity	NPC33507
0.6721	Remote Similarity	NPC63047
0.6721	Remote Similarity	NPC223595
0.6721	Remote Similarity	NPC475248
0.6721	Remote Similarity	NPC167724
0.6718	Remote Similarity	NPC198401
0.6716	Remote Similarity	NPC477173
0.6714	Remote Similarity	NPC31097
0.671	Remote Similarity	NPC276949
0.671	Remote Similarity	NPC35850
0.6706	Remote Similarity	NPC243162
0.6703	Remote Similarity	NPC242269
0.6702	Remote Similarity	NPC475685
0.6702	Remote Similarity	NPC282092
0.67	Remote Similarity	NPC477179
0.6685	Remote Similarity	NPC472121
0.6685	Remote Similarity	NPC161827
0.6684	Remote Similarity	NPC105055
0.6684	Remote Similarity	NPC97584
0.6684	Remote Similarity	NPC22689
0.6683	Remote Similarity	NPC470488
0.6667	Remote Similarity	NPC17059
0.6667	Remote Similarity	NPC477178
0.6667	Remote Similarity	NPC2823
0.6667	Remote Similarity	NPC264589
0.6667	Remote Similarity	NPC113626
0.6667	Remote Similarity	NPC477181
0.6667	Remote Similarity	NPC254850
0.6667	Remote Similarity	NPC477180
0.6667	Remote Similarity	NPC200589
0.6667	Remote Similarity	NPC473376
0.6649	Remote Similarity	NPC99043
0.6649	Remote Similarity	NPC218594
0.6649	Remote Similarity	NPC117244
0.6649	Remote Similarity	NPC133003
0.6649	Remote Similarity	NPC473763
0.6648	Remote Similarity	NPC144691
0.6646	Remote Similarity	NPC476950

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 NPC355 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	475
0.2-0.3	728
0.3-0.4	1489
0.4-0.5	3069
0.5-0.6	2662
0.6-0.7	532
0.7-0.8	23
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
0.765	Intermediate Similarity	NPD8240	Discontinued
0.756	Intermediate Similarity	NPD3248	Phase 1
0.741	Intermediate Similarity	NPD6017	Discontinued
0.7394	Intermediate Similarity	NPD2820	Phase 3
0.7368	Intermediate Similarity	NPD7072	Phase 2
0.7345	Intermediate Similarity	NPD7795	Phase 2
0.7341	Intermediate Similarity	NPD7599	Phase 2
0.7333	Intermediate Similarity	NPD2365	Approved
0.7299	Intermediate Similarity	NPD7600	Phase 2
0.7278	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD951	Approved
0.7225	Intermediate Similarity	NPD6855	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD979	Approved
0.7176	Intermediate Similarity	NPD4432	Discontinued
0.716	Intermediate Similarity	NPD2949	Approved
0.716	Intermediate Similarity	NPD2950	Approved
0.7143	Intermediate Similarity	NPD4393	Approved
0.7143	Intermediate Similarity	NPD33	Approved
0.7099	Intermediate Similarity	NPD1919	Approved
0.7099	Intermediate Similarity	NPD1920	Approved
0.7091	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5748	Phase 2
0.7011	Intermediate Similarity	NPD2790	Discontinued
0.6982	Remote Similarity	NPD5024	Approved
0.6961	Remote Similarity	NPD2369	Discontinued
0.6952	Remote Similarity	NPD5923	Phase 1
0.6927	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6768	Approved
0.6902	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4942	Approved
0.6868	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3625	Discontinued
0.6848	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1527	Phase 2
0.6842	Remote Similarity	NPD4948	Discontinued
0.6842	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6557	Phase 2
0.6823	Remote Similarity	NPD5042	Phase 1
0.6813	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7011	Discontinued
0.6796	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3989	Phase 3
0.6784	Remote Similarity	NPD6176	Phase 1
0.6782	Remote Similarity	NPD5942	Approved
0.6782	Remote Similarity	NPD5941	Approved
0.6765	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3990	Phase 3
0.6747	Remote Similarity	NPD1541	Approved
0.6742	Remote Similarity	NPD1663	Discontinued
0.674	Remote Similarity	NPD3790	Phase 2
0.6736	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1036	Approved
0.6704	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3227	Phase 2
0.6701	Remote Similarity	NPD5856	Discontinued
0.6688	Remote Similarity	NPD1344	Phase 2
0.6687	Remote Similarity	NPD1593	Approved
0.6686	Remote Similarity	NPD4430	Phase 2
0.6667	Remote Similarity	NPD8643	Discontinued
0.6667	Remote Similarity	NPD7308	Discontinued
0.6667	Remote Similarity	NPD2093	Discontinued
0.6667	Remote Similarity	NPD2791	Discontinued
0.6667	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1524	Phase 1
0.6649	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD4091	Approved
0.663	Remote Similarity	NPD3983	Phase 3
0.663	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6566	Discontinued
0.6627	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5578	Approved
0.6615	Remote Similarity	NPD5809	Phase 3
0.6614	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5932	Phase 3
0.6609	Remote Similarity	NPD5933	Phase 3
0.6609	Remote Similarity	NPD5931	Phase 3
0.6606	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1781	Discontinued
0.6603	Remote Similarity	NPD1175	Approved
0.6602	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5552	Discontinued
0.6596	Remote Similarity	NPD4092	Approved
0.659	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5526	Phase 2
0.6585	Remote Similarity	NPD2840	Approved
0.6585	Remote Similarity	NPD797	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7105	Phase 1
0.655	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7944	Discontinued
0.6548	Remote Similarity	NPD941	Approved
0.6536	Remote Similarity	NPD5086	Approved
0.6534	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5937	Approved
0.6528	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1619	Phase 3
0.6519	Remote Similarity	NPD2622	Approved
0.6519	Remote Similarity	NPD8630	Approved
0.6512	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4412	Phase 2
0.6509	Remote Similarity	NPD7200	Approved
0.6508	Remote Similarity	NPD3994	Approved
0.6508	Remote Similarity	NPD3995	Approved
0.6508	Remote Similarity	NPD3993	Approved
0.6508	Remote Similarity	NPD3991	Approved
0.6508	Remote Similarity	NPD3996	Approved
0.6508	Remote Similarity	NPD3992	Approved
0.6505	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6987	Phase 1
0.65	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6999	Discontinued
0.6497	Remote Similarity	NPD5181	Approved
0.6497	Remote Similarity	NPD4888	Discontinued
0.6497	Remote Similarity	NPD5179	Approved
0.6497	Remote Similarity	NPD5180	Approved
0.6497	Remote Similarity	NPD4682	Phase 2
0.6495	Remote Similarity	NPD4515	Suspended
0.6494	Remote Similarity	NPD1625	Approved
0.6492	Remote Similarity	NPD2287	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.649	Remote Similarity	NPD3780	Phase 2
0.6489	Remote Similarity	NPD3522	Approved
0.6489	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6486	Approved
0.6488	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7232	Discontinued
0.6488	Remote Similarity	NPD6487	Approved
0.6477	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD2813	Phase 3
0.6476	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7771	Discontinued
0.6474	Remote Similarity	NPD3782	Discontinued
0.6474	Remote Similarity	NPD3999	Approved
0.6474	Remote Similarity	NPD3997	Approved
0.6474	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3998	Approved
0.6471	Remote Similarity	NPD7001	Phase 3
0.6467	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6395	Phase 2
0.6464	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD2351	Discontinued
0.6463	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5918	Discontinued
0.6455	Remote Similarity	NPD5471	Phase 3
0.645	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD2506	Approved
0.6447	Remote Similarity	NPD7570	Approved
0.6447	Remote Similarity	NPD7569	Approved
0.6447	Remote Similarity	NPD8146	Phase 2
0.6442	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8165	Discontinued
0.644	Remote Similarity	NPD4329	Approved
0.644	Remote Similarity	NPD4330	Approved
0.644	Remote Similarity	NPD6878	Phase 2
0.644	Remote Similarity	NPD6879	Phase 2
0.6436	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7817	Phase 1
0.6436	Remote Similarity	NPD750	Phase 2
0.6436	Remote Similarity	NPD5017	Discontinued
0.6433	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4796	Discontinued
0.6429	Remote Similarity	NPD4499	Approved
0.6429	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5982	Phase 2
0.6422	Remote Similarity	NPD8115	Approved
0.6422	Remote Similarity	NPD8114	Approved
0.6421	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5840	Discontinued
0.6421	Remote Similarity	NPD5600	Discontinued
0.642	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD1573	Approved
0.6417	Remote Similarity	NPD1575	Approved
0.6413	Remote Similarity	NPD19	Approved
0.6413	Remote Similarity	NPD1742	Approved
0.6413	Remote Similarity	NPD1743	Approved
0.641	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4988	Discontinued
0.6408	Remote Similarity	NPD2443	Approved
0.6408	Remote Similarity	NPD2442	Approved
0.6408	Remote Similarity	NPD7666	Phase 3
0.6408	Remote Similarity	NPD7665	Phase 2
0.6402	Remote Similarity	NPD2584	Suspended
0.6402	Remote Similarity	NPD7449	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