NPASS Compound

Structure

NPC473547 OpenBabel07101718182D 45 52 0 0 1 0 0 0 0 0999 V2000 1.5578 0.9056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7261 -3.8410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8298 -4.2401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2126 -0.5985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0063 -1.1752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3319 -0.3032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3322 -2.1806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0831 -0.8786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5012 -0.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6325 -3.2466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7828 -2.7560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6325 -0.3032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7828 0.1874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5578 -0.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5576 -0.6779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7748 -0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4153 -3.0592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7748 -2.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9566 -3.1618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0484 0.0559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6245 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4822 -2.7560 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5767 -0.7938 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6245 -1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9251 -1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9920 -2.2655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5576 -2.2655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1343 -1.4717 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9251 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7828 -1.7749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4153 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0295 0.0559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9324 -3.2643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1100 -1.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6325 -1.2843 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9331 -1.2843 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4822 -1.7749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9331 -0.3032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9920 -0.6779 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5201 0.9056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3322 0.5931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5201 -0.7938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5091 -2.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 34 1 0 0 0 0 3 34 1 0 0 0 0 4 35 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 37 1 0 0 0 0 9 43 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 31 1 0 0 0 0 12 13 1 0 0 0 0 12 36 1 0 0 0 0 13 39 1 0 0 0 0 14 21 2 0 0 0 0 15 22 1 0 0 0 0 16 22 2 0 0 0 0 16 30 1 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 37 1 0 0 0 0 20 28 2 0 0 0 0 20 34 1 0 0 0 0 21 33 1 0 0 0 0 22 25 1 0 0 0 0 23 38 1 1 0 0 0 24 14 1 6 0 0 0 24 44 1 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 26 30 2 0 0 0 0 27 32 2 0 0 0 0 28 29 1 0 0 0 0 29 15 1 1 0 0 0 29 35 1 0 0 0 0 30 40 1 0 0 0 0 31 36 1 6 0 0 0 31 37 1 0 0 0 0 32 38 1 0 0 0 0 32 40 1 0 0 0 0 33 41 2 0 0 0 0 33 43 1 0 0 0 0 34 45 1 0 0 0 0 35 45 1 0 0 0 0 36 38 1 1 0 0 0 37 39 1 6 0 0 0 38 8 1 1 0 0 0 39 42 1 1 0 0 0 39 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	613.38
Volume:	651.141
LogP:	7.57
LogD:	4.921
LogS:	-5.503
# Rotatable Bonds:	3
TPSA:	80.78
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.268
Synthetic Accessibility Score:	5.574
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.162
MDCK Permeability:	2.0757082893396728e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.887
30% Bioavailability (F30%):	0.389

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	95.23811340332031%
Volume Distribution (VD):	3.727
Pgp-substrate:	2.6563143730163574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.519
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.787
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.624
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.984
CYP3A4-substrate:	0.934

ADMET: Excretion

Clearance (CL):	9.984
Half-life (T1/2):	0.03

ADMET: Toxicity

hERG Blockers:	0.955
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.522
Carcinogencity:	0.944
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC473547

Natural Product ID:	NPC473547
*Common Name:**	Nodulisporic Acid D1 Methyl Ester
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid D1 Methyl Ester
Standard InCHIKey:	IEBHNEDRQAMFNT-XJLPSLHVSA-N
Standard InCHI:	InChI=1S/C39H51NO5/c1-21(33(41)43-9)14-24-19-37(7)31-11-10-23-17-27-26-18-25-22(15-29-28(25)20-34(2,3)45-35(29,4)5)16-30(26)40-32(27)38(23,8)36(31,6)12-13-39(37,42)44-24/h14,16,18,20,23-24,29,31,40,42H,10-13,15,17,19H2,1-9H3/b21-14+/t23-,24+,29-,31+,36-,37-,38+,39-/m0/s1
SMILES:	COC(=O)/C(=C/[C@@H]1C[C@@]2([C@](O1)(O)CC[C@]1([C@H]2CC[C@@H]2[C@]1(C)c1[nH]c3c(c1C2)cc1c(c3)C[C@H]2C1=CC(OC2(C)C)(C)C)C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445248
PubChem CID:	11250520
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO32628	nodulisporium	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387649]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	100.0	nM	PMID[529532]

☑ 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 NPC473547 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	355
0.1-0.2	1498
0.2-0.3	3774
0.3-0.4	19685
0.4-0.5	12743
0.5-0.6	3220
0.6-0.7	1275
0.7-0.8	95
0.8-0.85	28
0.85-0.9	14
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9947	High Similarity	NPC97388
0.9634	High Similarity	NPC475165
0.9583	High Similarity	NPC250129
0.9343	High Similarity	NPC242446
0.9343	High Similarity	NPC475476
0.9323	High Similarity	NPC187456
0.9263	High Similarity	NPC475151
0.9163	High Similarity	NPC475424
0.9163	High Similarity	NPC79107
0.9082	High Similarity	NPC284102
0.9058	High Similarity	NPC473747
0.9045	High Similarity	NPC473650
0.9045	High Similarity	NPC160527
0.8894	High Similarity	NPC282033
0.8667	High Similarity	NPC471634
0.8667	High Similarity	NPC473806
0.8641	High Similarity	NPC61813
0.8594	High Similarity	NPC206967
0.8525	High Similarity	NPC94541
0.8525	High Similarity	NPC470843
0.8483	Intermediate Similarity	NPC183426
0.8446	Intermediate Similarity	NPC34271
0.8406	Intermediate Similarity	NPC96131
0.84	Intermediate Similarity	NPC123019
0.8381	Intermediate Similarity	NPC469312
0.8381	Intermediate Similarity	NPC41318
0.8316	Intermediate Similarity	NPC6093
0.8216	Intermediate Similarity	NPC245756
0.8213	Intermediate Similarity	NPC235900
0.8177	Intermediate Similarity	NPC198339
0.8144	Intermediate Similarity	NPC165201
0.8134	Intermediate Similarity	NPC471284
0.8112	Intermediate Similarity	NPC119700
0.805	Intermediate Similarity	NPC85066
0.805	Intermediate Similarity	NPC181502
0.801	Intermediate Similarity	NPC97525
0.801	Intermediate Similarity	NPC18661
0.7956	Intermediate Similarity	NPC311451
0.7921	Intermediate Similarity	NPC231342
0.7892	Intermediate Similarity	NPC473565
0.7892	Intermediate Similarity	NPC278540
0.7857	Intermediate Similarity	NPC302191
0.7857	Intermediate Similarity	NPC471583
0.7857	Intermediate Similarity	NPC471782
0.7718	Intermediate Similarity	NPC32200
0.7711	Intermediate Similarity	NPC46413
0.77	Intermediate Similarity	NPC99428
0.768	Intermediate Similarity	NPC126492
0.7639	Intermediate Similarity	NPC131273
0.7639	Intermediate Similarity	NPC473441
0.7577	Intermediate Similarity	NPC154293
0.7573	Intermediate Similarity	NPC205403
0.7534	Intermediate Similarity	NPC470874
0.7512	Intermediate Similarity	NPC470280
0.7488	Intermediate Similarity	NPC204303
0.7477	Intermediate Similarity	NPC235885
0.7411	Intermediate Similarity	NPC470873
0.7406	Intermediate Similarity	NPC477135
0.7389	Intermediate Similarity	NPC476319
0.7333	Intermediate Similarity	NPC249342
0.7313	Intermediate Similarity	NPC270009
0.7304	Intermediate Similarity	NPC280290
0.7302	Intermediate Similarity	NPC474905
0.7289	Intermediate Similarity	NPC472762
0.7286	Intermediate Similarity	NPC34508
0.7277	Intermediate Similarity	NPC300688
0.7265	Intermediate Similarity	NPC2395
0.7215	Intermediate Similarity	NPC475778
0.7206	Intermediate Similarity	NPC19679
0.7202	Intermediate Similarity	NPC234999
0.7195	Intermediate Similarity	NPC203614
0.7195	Intermediate Similarity	NPC204491
0.7186	Intermediate Similarity	NPC280548
0.7165	Intermediate Similarity	NPC184476
0.7157	Intermediate Similarity	NPC472587
0.7136	Intermediate Similarity	NPC473189
0.7111	Intermediate Similarity	NPC280799
0.711	Intermediate Similarity	NPC61637
0.7105	Intermediate Similarity	NPC57690
0.7101	Intermediate Similarity	NPC160381
0.7094	Intermediate Similarity	NPC151939
0.7087	Intermediate Similarity	NPC474701
0.7087	Intermediate Similarity	NPC477531
0.7083	Intermediate Similarity	NPC476115
0.7074	Intermediate Similarity	NPC252251
0.7073	Intermediate Similarity	NPC192270
0.7071	Intermediate Similarity	NPC8104
0.7064	Intermediate Similarity	NPC475844
0.7048	Intermediate Similarity	NPC147446
0.7048	Intermediate Similarity	NPC266192
0.7048	Intermediate Similarity	NPC51388
0.7045	Intermediate Similarity	NPC126066
0.7045	Intermediate Similarity	NPC475422
0.7043	Intermediate Similarity	NPC209174
0.7039	Intermediate Similarity	NPC472444
0.7037	Intermediate Similarity	NPC137589
0.7037	Intermediate Similarity	NPC193761
0.7032	Intermediate Similarity	NPC127677
0.7032	Intermediate Similarity	NPC258062
0.7023	Intermediate Similarity	NPC313985
0.7023	Intermediate Similarity	NPC81654
0.7023	Intermediate Similarity	NPC79129
0.7023	Intermediate Similarity	NPC249150
0.7023	Intermediate Similarity	NPC195461
0.7023	Intermediate Similarity	NPC49196
0.7018	Intermediate Similarity	NPC476106
0.7018	Intermediate Similarity	NPC141428
0.7013	Intermediate Similarity	NPC290529
0.7009	Intermediate Similarity	NPC477044
0.7009	Intermediate Similarity	NPC477041
0.7005	Intermediate Similarity	NPC98715
0.7	Intermediate Similarity	NPC274640
0.6987	Remote Similarity	NPC267926
0.6986	Remote Similarity	NPC225821
0.6986	Remote Similarity	NPC46225
0.6982	Remote Similarity	NPC87856
0.6982	Remote Similarity	NPC151976
0.6979	Remote Similarity	NPC188239
0.6978	Remote Similarity	NPC82070
0.6977	Remote Similarity	NPC477045
0.6977	Remote Similarity	NPC476175
0.6976	Remote Similarity	NPC213468
0.6976	Remote Similarity	NPC472443
0.6972	Remote Similarity	NPC477043
0.697	Remote Similarity	NPC473320
0.6964	Remote Similarity	NPC132211
0.696	Remote Similarity	NPC477532
0.6955	Remote Similarity	NPC87755
0.6953	Remote Similarity	NPC70155
0.6951	Remote Similarity	NPC267965
0.6944	Remote Similarity	NPC214428
0.694	Remote Similarity	NPC474688
0.6937	Remote Similarity	NPC9894
0.6935	Remote Similarity	NPC16667
0.693	Remote Similarity	NPC50503
0.6923	Remote Similarity	NPC477548
0.6919	Remote Similarity	NPC106833
0.6919	Remote Similarity	NPC469497
0.6915	Remote Similarity	NPC470509
0.6912	Remote Similarity	NPC472586
0.6912	Remote Similarity	NPC267423
0.6912	Remote Similarity	NPC300183
0.6907	Remote Similarity	NPC124005
0.6906	Remote Similarity	NPC473180
0.6906	Remote Similarity	NPC48353
0.69	Remote Similarity	NPC475271
0.6897	Remote Similarity	NPC6982
0.6881	Remote Similarity	NPC201700
0.6878	Remote Similarity	NPC288785
0.6878	Remote Similarity	NPC39679
0.6872	Remote Similarity	NPC52254
0.6872	Remote Similarity	NPC128751
0.6872	Remote Similarity	NPC246700
0.6869	Remote Similarity	NPC195314
0.6866	Remote Similarity	NPC470508
0.6864	Remote Similarity	NPC277350
0.6856	Remote Similarity	NPC144452
0.6854	Remote Similarity	NPC55493
0.6853	Remote Similarity	NPC38736
0.6849	Remote Similarity	NPC37473
0.6847	Remote Similarity	NPC271862
0.6847	Remote Similarity	NPC201697
0.6847	Remote Similarity	NPC469743
0.6845	Remote Similarity	NPC293472
0.684	Remote Similarity	NPC95783
0.684	Remote Similarity	NPC202503
0.6837	Remote Similarity	NPC11445
0.6835	Remote Similarity	NPC476044
0.6834	Remote Similarity	NPC67056
0.6833	Remote Similarity	NPC477065
0.6833	Remote Similarity	NPC193777
0.6825	Remote Similarity	NPC473177
0.682	Remote Similarity	NPC241024
0.6816	Remote Similarity	NPC199667
0.6814	Remote Similarity	NPC476114
0.6806	Remote Similarity	NPC153042
0.6805	Remote Similarity	NPC199259
0.6804	Remote Similarity	NPC475112
0.6804	Remote Similarity	NPC474116
0.6804	Remote Similarity	NPC162730
0.6804	Remote Similarity	NPC291535
0.6804	Remote Similarity	NPC475085
0.6804	Remote Similarity	NPC129042
0.68	Remote Similarity	NPC475602
0.68	Remote Similarity	NPC31700
0.6796	Remote Similarity	NPC56618
0.6793	Remote Similarity	NPC6786
0.6791	Remote Similarity	NPC195239
0.6791	Remote Similarity	NPC157828
0.6789	Remote Similarity	NPC470279
0.6786	Remote Similarity	NPC87413
0.6784	Remote Similarity	NPC293151
0.6784	Remote Similarity	NPC249428
0.6784	Remote Similarity	NPC314552
0.6777	Remote Similarity	NPC473389
0.6774	Remote Similarity	NPC72211
0.6771	Remote Similarity	NPC473181
0.677	Remote Similarity	NPC118228
0.6769	Remote Similarity	NPC477134
0.6768	Remote Similarity	NPC471458

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 NPC473547 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	594
0.2-0.3	627
0.3-0.4	2178
0.4-0.5	3484
0.5-0.6	1685
0.6-0.7	345
0.7-0.8	10
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
0.743	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7957	Phase 1
0.7256	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7688	Phase 1
0.7232	Intermediate Similarity	NPD6995	Phase 1
0.7123	Intermediate Similarity	NPD5003	Discontinued
0.7023	Intermediate Similarity	NPD4600	Approved
0.7023	Intermediate Similarity	NPD4601	Approved
0.7005	Intermediate Similarity	NPD2920	Discontinued
0.6972	Remote Similarity	NPD8283	Approved
0.6972	Remote Similarity	NPD8282	Approved
0.6972	Remote Similarity	NPD56	Approved
0.6955	Remote Similarity	NPD8399	Phase 1
0.6955	Remote Similarity	NPD8423	Phase 2
0.695	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5835	Phase 3
0.6923	Remote Similarity	NPD5834	Phase 3
0.692	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2564	Approved
0.6919	Remote Similarity	NPD2565	Phase 2
0.6849	Remote Similarity	NPD6176	Phase 1
0.6844	Remote Similarity	NPD7707	Approved
0.684	Remote Similarity	NPD6281	Approved
0.6825	Remote Similarity	NPD8431	Approved
0.6824	Remote Similarity	NPD7824	Approved
0.6814	Remote Similarity	NPD8160	Phase 2
0.6808	Remote Similarity	NPD5913	Phase 3
0.6808	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7233	Approved
0.6792	Remote Similarity	NPD7234	Approved
0.6784	Remote Similarity	NPD5164	Discontinued
0.6783	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1326	Approved
0.6765	Remote Similarity	NPD1325	Approved
0.6757	Remote Similarity	NPD5429	Discontinued
0.6743	Remote Similarity	NPD6249	Phase 2
0.6743	Remote Similarity	NPD6248	Phase 2
0.6743	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5901	Discontinued
0.6741	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7730	Approved
0.6738	Remote Similarity	NPD7731	Approved
0.6731	Remote Similarity	NPD4076	Approved
0.6731	Remote Similarity	NPD4079	Approved
0.6724	Remote Similarity	NPD7271	Approved
0.6719	Remote Similarity	NPD8364	Approved
0.6719	Remote Similarity	NPD8363	Approved
0.6712	Remote Similarity	NPD6479	Discontinued
0.6712	Remote Similarity	NPD4500	Approved
0.6712	Remote Similarity	NPD4501	Approved
0.6712	Remote Similarity	NPD7010	Phase 3
0.6711	Remote Similarity	NPD7470	Discontinued
0.6699	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD8072	Approved
0.6697	Remote Similarity	NPD7946	Pre-registration
0.6683	Remote Similarity	NPD3505	Approved
0.6683	Remote Similarity	NPD3506	Approved
0.6683	Remote Similarity	NPD2144	Approved
0.6682	Remote Similarity	NPD4511	Phase 1
0.6682	Remote Similarity	NPD4499	Approved
0.6681	Remote Similarity	NPD7455	Approved
0.6681	Remote Similarity	NPD7454	Approved
0.6681	Remote Similarity	NPD7716	Approved
0.6681	Remote Similarity	NPD7717	Approved
0.6667	Remote Similarity	NPD7950	Approved
0.6667	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7952	Approved
0.6667	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7953	Approved
0.6667	Remote Similarity	NPD7951	Approved
0.6667	Remote Similarity	NPD7789	Approved
0.6667	Remote Similarity	NPD7790	Approved
0.6667	Remote Similarity	NPD6978	Phase 2
0.6667	Remote Similarity	NPD3038	Discontinued
0.6667	Remote Similarity	NPD7791	Approved
0.6652	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8073	Approved
0.6652	Remote Similarity	NPD2509	Approved
0.6652	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD2510	Approved
0.665	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7780	Approved
0.6638	Remote Similarity	NPD7781	Approved
0.6637	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4334	Discontinued
0.6634	Remote Similarity	NPD2844	Phase 3
0.6634	Remote Similarity	NPD5021	Discontinued
0.6628	Remote Similarity	NPD8467	Approved
0.6628	Remote Similarity	NPD8427	Approved
0.6628	Remote Similarity	NPD8466	Approved
0.6628	Remote Similarity	NPD8465	Approved
0.6628	Remote Similarity	NPD8428	Approved
0.6628	Remote Similarity	NPD8429	Approved
0.6622	Remote Similarity	NPD7941	Phase 3
0.6622	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7770	Phase 3
0.6609	Remote Similarity	NPD7395	Discontinued
0.6595	Remote Similarity	NPD5506	Approved
0.6595	Remote Similarity	NPD5507	Approved
0.6591	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.658	Remote Similarity	NPD6455	Phase 3
0.6574	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8358	Approved
0.6571	Remote Similarity	NPD8386	Phase 2
0.6569	Remote Similarity	NPD6635	Approved
0.6568	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD1534	Approved
0.6557	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5104	Approved
0.6552	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD5487	Phase 1
0.6544	Remote Similarity	NPD4315	Phase 2
0.6538	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4463	Approved
0.6533	Remote Similarity	NPD4462	Approved
0.6531	Remote Similarity	NPD5254	Discontinued
0.6527	Remote Similarity	NPD8426	Approved
0.6527	Remote Similarity	NPD8460	Approved
0.6527	Remote Similarity	NPD8459	Approved
0.6527	Remote Similarity	NPD8425	Approved
0.6522	Remote Similarity	NPD3389	Approved
0.6522	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3393	Approved
0.6522	Remote Similarity	NPD3394	Approved
0.6522	Remote Similarity	NPD7474	Suspended
0.6516	Remote Similarity	NPD8396	Approved
0.6516	Remote Similarity	NPD8395	Approved
0.6507	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD8094	Discontinued
0.65	Remote Similarity	NPD6206	Phase 1
0.6493	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5939	Approved
0.6491	Remote Similarity	NPD5936	Approved
0.649	Remote Similarity	NPD7921	Approved
0.6484	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4506	Discontinued
0.6473	Remote Similarity	NPD5891	Approved
0.6471	Remote Similarity	NPD6261	Phase 3
0.6465	Remote Similarity	NPD5444	Phase 1
0.6463	Remote Similarity	NPD8093	Discontinued
0.646	Remote Similarity	NPD8322	Phase 2
0.6459	Remote Similarity	NPD7418	Discontinued
0.6456	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5512	Phase 3
0.6452	Remote Similarity	NPD7769	Phase 3
0.645	Remote Similarity	NPD3833	Phase 3
0.645	Remote Similarity	NPD3835	Phase 3
0.6449	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6987	Phase 1
0.6438	Remote Similarity	NPD6770	Approved
0.6435	Remote Similarity	NPD7276	Approved
0.6435	Remote Similarity	NPD7277	Approved
0.6429	Remote Similarity	NPD1592	Phase 3
0.6429	Remote Similarity	NPD7187	Phase 2
0.6419	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5075	Discontinued
0.6419	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4897	Phase 2
0.6407	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD7956	Approved
0.6403	Remote Similarity	NPD7955	Approved
0.6402	Remote Similarity	NPD5596	Phase 2
0.6402	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4075	Phase 2
0.6396	Remote Similarity	NPD7777	Approved
0.6396	Remote Similarity	NPD53	Approved
0.6396	Remote Similarity	NPD7778	Approved
0.6395	Remote Similarity	NPD7878	Phase 2
0.6394	Remote Similarity	NPD4639	Approved
0.6394	Remote Similarity	NPD4638	Approved
0.6394	Remote Similarity	NPD4640	Approved
0.6391	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7069	Discontinued
0.6387	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5897	Approved
0.6385	Remote Similarity	NPD5898	Approved
0.6385	Remote Similarity	NPD5899	Approved
0.6384	Remote Similarity	NPD7934	Discovery
0.6384	Remote Similarity	NPD7727	Phase 2
0.6384	Remote Similarity	NPD7933	Approved
0.6384	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7931	Approved
0.6381	Remote Similarity	NPD43	Approved
0.6381	Remote Similarity	NPD6182	Approved
0.6381	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.638	Remote Similarity	NPD6550	Discontinued
0.6378	Remote Similarity	NPD7708	Approved
0.6377	Remote Similarity	NPD2915	Discontinued
0.6372	Remote Similarity	NPD8115	Approved
0.6372	Remote Similarity	NPD8098	Approved
0.6372	Remote Similarity	NPD8114	Approved
0.6368	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7865	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