NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	834.29
Volume:	771.947
LogP:	2.287
LogD:	1.748
LogS:	-4.306
# Rotatable Bonds:	9
TPSA:	260.35
# H-Bond Aceptor:	19
# H-Bond Donor:	6
# Rings:	9
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	7.691
Fsp3:	0.7
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.023
MDCK Permeability:	6.094282798585482e-05
Pgp-inhibitor:	0.181
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.848
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.343

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	64.55732727050781%
Volume Distribution (VD):	0.467
Pgp-substrate:	15.997634887695312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.997
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	2.909
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.894
Rat Oral Acute Toxicity:	0.423
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.854
Carcinogencity:	0.939
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.349

Download Data

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

Natural Product: NPC478035

Natural Product ID:	NPC478035
*Common Name:**	Trioxacarcin D
IUPAC Name:	(1S,8S,10S,17S,18S,19R,21S)-17-[(2S,4R,5S,6S)-5-acetyl-4,5-dihydroxy-6-methyloxan-2-yl]oxy-8-[(2R,4R,5R,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-19-(dimethoxymethyl)-10,13-dihydroxy-6-methoxy-3-methylspiro[16,20,22-trioxahexacyclo[17.2.1.02,15.05,14.07,12.017,21]docosa-2(15),3,5(14),6,12-pentaene-18,2'-oxirane]-11-one
Synonyms:	Trioxacarcin D
Standard InCHIKey:	OIAMNLQWYUHUAN-FVHIEPIMSA-N
Standard InCHI:	InChI=1S/C40H50O19/c1-14-9-18-25(29(45)27-26(30(18)49-6)20(10-19(42)28(27)44)55-23-12-36(5,47)33(46)15(2)53-23)31-24(14)32-34-39(57-31,37(13-52-37)40(58-32,59-34)35(50-7)51-8)56-22-11-21(43)38(48,16(3)41)17(4)54-22/h9,15,17,19-23,32-35,42-43,45-48H,10-13H2,1-8H3/t15-,17-,19-,20-,21+,22-,23-,32-,33+,34-,36+,37-,38+,39+,40-/m0/s1
SMILES:	C[C@H]1[C@H]([C@](C[C@@H](O1)O[C@H]2C[C@@H](C(=O)C3=C(C4=C(C=C(C5=C4O[C@@]6([C@@H]7[C@H]5O[C@]([C@]68CO8)(O7)C(OC)OC)O[C@H]9C[C@H]([C@]([C@@H](O9)C)(C(=O)C)O)O)C)C(=C23)OC)O)O)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49799759
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0004158] 1-hydroxysteroids

*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
NPO33633	Streptomyces sp. isolate B8652 BCC 5149	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19299148]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.0015	ug/ml	PMID[19299148]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0017	ug/ml	PMID[19299148]

☑ 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 NPC478035 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	461
0.1-0.2	1722
0.2-0.3	3461
0.3-0.4	7758
0.4-0.5	10254
0.5-0.6	6633
0.6-0.7	6887
0.7-0.8	5223
0.8-0.85	286
0.85-0.9	9
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC478034
0.9278	High Similarity	NPC314687
0.8722	High Similarity	NPC470453
0.8722	High Similarity	NPC164047
0.8722	High Similarity	NPC470452
0.8722	High Similarity	NPC470448
0.8696	High Similarity	NPC48474
0.8667	High Similarity	NPC245059
0.8667	High Similarity	NPC84494
0.8652	High Similarity	NPC213052
0.8617	High Similarity	NPC131405
0.8611	High Similarity	NPC470582
0.8611	High Similarity	NPC115447
0.8611	High Similarity	NPC266513
0.8611	High Similarity	NPC470581
0.8603	High Similarity	NPC470583
0.8603	High Similarity	NPC19056
0.8548	High Similarity	NPC470199
0.8548	High Similarity	NPC314459
0.8541	High Similarity	NPC314672
0.8508	High Similarity	NPC83331
0.8503	High Similarity	NPC314020
0.85	High Similarity	NPC470454
0.85	High Similarity	NPC63105
0.85	High Similarity	NPC199533
0.8495	Intermediate Similarity	NPC321046
0.8492	Intermediate Similarity	NPC315619
0.8483	Intermediate Similarity	NPC246274
0.8483	Intermediate Similarity	NPC259905
0.8483	Intermediate Similarity	NPC473202
0.8478	Intermediate Similarity	NPC87583
0.8462	Intermediate Similarity	NPC187441
0.8462	Intermediate Similarity	NPC283980
0.8457	Intermediate Similarity	NPC470196
0.8457	Intermediate Similarity	NPC470195
0.8457	Intermediate Similarity	NPC470197
0.8457	Intermediate Similarity	NPC282474
0.8457	Intermediate Similarity	NPC470198
0.8457	Intermediate Similarity	NPC470193
0.8457	Intermediate Similarity	NPC316274
0.8457	Intermediate Similarity	NPC470194
0.8457	Intermediate Similarity	NPC470200
0.8453	Intermediate Similarity	NPC46958
0.8453	Intermediate Similarity	NPC232818
0.8453	Intermediate Similarity	NPC198893
0.8453	Intermediate Similarity	NPC475233
0.8453	Intermediate Similarity	NPC314489
0.8436	Intermediate Similarity	NPC470580
0.8407	Intermediate Similarity	NPC477682
0.8407	Intermediate Similarity	NPC477683
0.8389	Intermediate Similarity	NPC270027
0.8387	Intermediate Similarity	NPC41845
0.8378	Intermediate Similarity	NPC241847
0.8371	Intermediate Similarity	NPC178851
0.837	Intermediate Similarity	NPC475656
0.837	Intermediate Similarity	NPC475148
0.8361	Intermediate Similarity	NPC58538
0.8352	Intermediate Similarity	NPC102053
0.8352	Intermediate Similarity	NPC324220
0.8352	Intermediate Similarity	NPC475246
0.8352	Intermediate Similarity	NPC312630
0.8343	Intermediate Similarity	NPC98776
0.8333	Intermediate Similarity	NPC294863
0.8333	Intermediate Similarity	NPC282636
0.8324	Intermediate Similarity	NPC292706
0.8324	Intermediate Similarity	NPC148710
0.8324	Intermediate Similarity	NPC63470
0.8324	Intermediate Similarity	NPC49690
0.8324	Intermediate Similarity	NPC106700
0.8324	Intermediate Similarity	NPC472722
0.8324	Intermediate Similarity	NPC224557
0.8315	Intermediate Similarity	NPC477860
0.8315	Intermediate Similarity	NPC208069
0.8315	Intermediate Similarity	NPC475161
0.8315	Intermediate Similarity	NPC478026
0.8305	Intermediate Similarity	NPC216752
0.8297	Intermediate Similarity	NPC307754
0.8297	Intermediate Similarity	NPC223735
0.8297	Intermediate Similarity	NPC3718
0.8287	Intermediate Similarity	NPC76128
0.8287	Intermediate Similarity	NPC30432
0.8287	Intermediate Similarity	NPC111536
0.8287	Intermediate Similarity	NPC271385
0.8287	Intermediate Similarity	NPC5029
0.828	Intermediate Similarity	NPC221140
0.828	Intermediate Similarity	NPC475352
0.828	Intermediate Similarity	NPC475220
0.828	Intermediate Similarity	NPC229817
0.828	Intermediate Similarity	NPC473686
0.8278	Intermediate Similarity	NPC191653
0.8278	Intermediate Similarity	NPC5319
0.827	Intermediate Similarity	NPC313452
0.827	Intermediate Similarity	NPC473072
0.827	Intermediate Similarity	NPC478001
0.8268	Intermediate Similarity	NPC178173
0.8261	Intermediate Similarity	NPC299149
0.8261	Intermediate Similarity	NPC114257
0.8261	Intermediate Similarity	NPC277710
0.8261	Intermediate Similarity	NPC153578
0.8258	Intermediate Similarity	NPC17432
0.8251	Intermediate Similarity	NPC98943
0.8251	Intermediate Similarity	NPC289876
0.8242	Intermediate Similarity	NPC25724
0.8242	Intermediate Similarity	NPC85368
0.8242	Intermediate Similarity	NPC154986
0.8242	Intermediate Similarity	NPC203751
0.8239	Intermediate Similarity	NPC470607
0.8235	Intermediate Similarity	NPC174486
0.8232	Intermediate Similarity	NPC477571
0.8232	Intermediate Similarity	NPC477572
0.8232	Intermediate Similarity	NPC477573
0.8232	Intermediate Similarity	NPC298778
0.8222	Intermediate Similarity	NPC225419
0.8222	Intermediate Similarity	NPC473094
0.8216	Intermediate Similarity	NPC473071
0.8216	Intermediate Similarity	NPC315221
0.8216	Intermediate Similarity	NPC197357
0.8216	Intermediate Similarity	NPC473073
0.8216	Intermediate Similarity	NPC85316
0.8207	Intermediate Similarity	NPC241196
0.8207	Intermediate Similarity	NPC67302
0.8197	Intermediate Similarity	NPC68381
0.8192	Intermediate Similarity	NPC470358
0.8187	Intermediate Similarity	NPC9002
0.8187	Intermediate Similarity	NPC288152
0.8187	Intermediate Similarity	NPC137871
0.8187	Intermediate Similarity	NPC257011
0.8187	Intermediate Similarity	NPC476159
0.8182	Intermediate Similarity	NPC470606
0.8177	Intermediate Similarity	NPC137460
0.8177	Intermediate Similarity	NPC473095
0.8177	Intermediate Similarity	NPC473096
0.8172	Intermediate Similarity	NPC473883
0.8172	Intermediate Similarity	NPC473631
0.8172	Intermediate Similarity	NPC475662
0.8172	Intermediate Similarity	NPC293227
0.8172	Intermediate Similarity	NPC473717
0.8167	Intermediate Similarity	NPC70441
0.8162	Intermediate Similarity	NPC241423
0.8162	Intermediate Similarity	NPC473682
0.8162	Intermediate Similarity	NPC470444
0.8162	Intermediate Similarity	NPC473571
0.8162	Intermediate Similarity	NPC110941
0.8162	Intermediate Similarity	NPC126784
0.8162	Intermediate Similarity	NPC470443
0.8156	Intermediate Similarity	NPC257566
0.8156	Intermediate Similarity	NPC183672
0.8156	Intermediate Similarity	NPC124155
0.8152	Intermediate Similarity	NPC65563
0.8152	Intermediate Similarity	NPC156635
0.8152	Intermediate Similarity	NPC255799
0.8152	Intermediate Similarity	NPC469345
0.8152	Intermediate Similarity	NPC257714
0.8152	Intermediate Similarity	NPC169733
0.8152	Intermediate Similarity	NPC470949
0.8142	Intermediate Similarity	NPC470335
0.8142	Intermediate Similarity	NPC470336
0.8132	Intermediate Similarity	NPC199079
0.8132	Intermediate Similarity	NPC251144
0.8132	Intermediate Similarity	NPC241874
0.8132	Intermediate Similarity	NPC241387
0.8132	Intermediate Similarity	NPC210808
0.8132	Intermediate Similarity	NPC477670
0.8128	Intermediate Similarity	NPC470455
0.8128	Intermediate Similarity	NPC470451
0.8128	Intermediate Similarity	NPC75574
0.8125	Intermediate Similarity	NPC17521
0.8122	Intermediate Similarity	NPC249977
0.8122	Intermediate Similarity	NPC103633
0.8114	Intermediate Similarity	NPC470331
0.8111	Intermediate Similarity	NPC294722
0.8111	Intermediate Similarity	NPC475979
0.8111	Intermediate Similarity	NPC470735
0.8111	Intermediate Similarity	NPC287889
0.8111	Intermediate Similarity	NPC329647
0.8111	Intermediate Similarity	NPC135358
0.8108	Intermediate Similarity	NPC168584
0.8108	Intermediate Similarity	NPC233978
0.8108	Intermediate Similarity	NPC5671
0.8105	Intermediate Similarity	NPC264302
0.8101	Intermediate Similarity	NPC472402
0.8101	Intermediate Similarity	NPC44947
0.8101	Intermediate Similarity	NPC131745
0.8101	Intermediate Similarity	NPC259834
0.8098	Intermediate Similarity	NPC232412
0.8098	Intermediate Similarity	NPC108202
0.8098	Intermediate Similarity	NPC472607
0.8098	Intermediate Similarity	NPC470667
0.8098	Intermediate Similarity	NPC86809
0.8098	Intermediate Similarity	NPC294629
0.8098	Intermediate Similarity	NPC98667
0.8098	Intermediate Similarity	NPC162248
0.8098	Intermediate Similarity	NPC102028
0.8098	Intermediate Similarity	NPC474345
0.8095	Intermediate Similarity	NPC473618
0.8087	Intermediate Similarity	NPC183441
0.8087	Intermediate Similarity	NPC169018
0.8085	Intermediate Similarity	NPC197972
0.8077	Intermediate Similarity	NPC222455
0.8077	Intermediate Similarity	NPC207574

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 NPC478035 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	897
0.2-0.3	2019
0.3-0.4	2847
0.4-0.5	1918
0.5-0.6	752
0.6-0.7	232
0.7-0.8	90
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7808	Phase 3
0.8043	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD6797	Phase 2
0.7957	Intermediate Similarity	NPD8312	Approved
0.7957	Intermediate Similarity	NPD8313	Approved
0.7935	Intermediate Similarity	NPD7472	Approved
0.7908	Intermediate Similarity	NPD7697	Approved
0.7908	Intermediate Similarity	NPD7696	Phase 3
0.7908	Intermediate Similarity	NPD7698	Approved
0.788	Intermediate Similarity	NPD7054	Approved
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7846	Intermediate Similarity	NPD6778	Approved
0.7846	Intermediate Similarity	NPD6781	Approved
0.7846	Intermediate Similarity	NPD6780	Approved
0.7846	Intermediate Similarity	NPD6782	Approved
0.7846	Intermediate Similarity	NPD6777	Approved
0.7846	Intermediate Similarity	NPD6776	Approved
0.7846	Intermediate Similarity	NPD6779	Approved
0.7839	Intermediate Similarity	NPD7701	Phase 2
0.7838	Intermediate Similarity	NPD7074	Phase 3
0.7835	Intermediate Similarity	NPD7699	Phase 2
0.7835	Intermediate Similarity	NPD7700	Phase 2
0.7826	Intermediate Similarity	NPD3751	Discontinued
0.7817	Intermediate Similarity	NPD7435	Discontinued
0.7807	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7870	Phase 2
0.7778	Intermediate Similarity	NPD7871	Phase 2
0.7747	Intermediate Similarity	NPD6959	Discontinued
0.773	Intermediate Similarity	NPD3818	Discontinued
0.7723	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7783	Phase 2
0.7705	Intermediate Similarity	NPD3787	Discontinued
0.768	Intermediate Similarity	NPD6534	Approved
0.768	Intermediate Similarity	NPD6535	Approved
0.7673	Intermediate Similarity	NPD7874	Approved
0.7673	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD7801	Approved
0.7624	Intermediate Similarity	NPD8151	Discontinued
0.7552	Intermediate Similarity	NPD8150	Discontinued
0.754	Intermediate Similarity	NPD7228	Approved
0.7527	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6166	Phase 2
0.7527	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6823	Phase 2
0.7486	Intermediate Similarity	NPD7075	Discontinued
0.7458	Intermediate Similarity	NPD2533	Approved
0.7458	Intermediate Similarity	NPD2532	Approved
0.7458	Intermediate Similarity	NPD2534	Approved
0.7444	Intermediate Similarity	NPD4380	Phase 2
0.7426	Intermediate Similarity	NPD8320	Phase 1
0.7426	Intermediate Similarity	NPD8319	Approved
0.7418	Intermediate Similarity	NPD7819	Suspended
0.7409	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD5494	Approved
0.7377	Intermediate Similarity	NPD5402	Approved
0.7371	Intermediate Similarity	NPD8434	Phase 2
0.733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7473	Discontinued
0.7292	Intermediate Similarity	NPD7240	Approved
0.7283	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6801	Discontinued
0.7263	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6232	Discontinued
0.7228	Intermediate Similarity	NPD2801	Approved
0.7228	Intermediate Similarity	NPD8455	Phase 2
0.7186	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6212	Phase 3
0.7186	Intermediate Similarity	NPD6213	Phase 3
0.7174	Intermediate Similarity	NPD1934	Approved
0.7166	Intermediate Similarity	NPD6234	Discontinued
0.7163	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD3882	Suspended
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD4966	Approved
0.7113	Intermediate Similarity	NPD7685	Pre-registration
0.7109	Intermediate Similarity	NPD7930	Approved
0.7097	Intermediate Similarity	NPD3817	Phase 2
0.7079	Intermediate Similarity	NPD2800	Approved
0.7072	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD8059	Phase 3
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5710	Approved
0.7053	Intermediate Similarity	NPD5711	Approved
0.7021	Intermediate Similarity	NPD3749	Approved
0.7	Intermediate Similarity	NPD1247	Approved
0.6995	Remote Similarity	NPD5403	Approved
0.6989	Remote Similarity	NPD37	Approved
0.6984	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6599	Discontinued
0.6952	Remote Similarity	NPD1465	Phase 2
0.694	Remote Similarity	NPD1512	Approved
0.6938	Remote Similarity	NPD7584	Approved
0.6935	Remote Similarity	NPD7411	Suspended
0.6927	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8285	Discontinued
0.6919	Remote Similarity	NPD3226	Approved
0.6912	Remote Similarity	NPD7907	Approved
0.6911	Remote Similarity	NPD7199	Phase 2
0.6907	Remote Similarity	NPD7799	Discontinued
0.689	Remote Similarity	NPD7999	Approved
0.6885	Remote Similarity	NPD5401	Approved
0.6878	Remote Similarity	NPD7768	Phase 2
0.6872	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2346	Discontinued
0.6872	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8366	Approved
0.6833	Remote Similarity	NPD1549	Phase 2
0.6831	Remote Similarity	NPD6799	Approved
0.6831	Remote Similarity	NPD7390	Discontinued
0.6831	Remote Similarity	NPD1511	Approved
0.682	Remote Similarity	NPD4111	Phase 1
0.6816	Remote Similarity	NPD6099	Approved
0.6816	Remote Similarity	NPD6100	Approved
0.6806	Remote Similarity	NPD919	Approved
0.6796	Remote Similarity	NPD6674	Discontinued
0.6794	Remote Similarity	NPD7680	Approved
0.6787	Remote Similarity	NPD8491	Approved
0.6774	Remote Similarity	NPD1653	Approved
0.6758	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD3750	Approved
0.6748	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4665	Approved
0.6741	Remote Similarity	NPD8067	Phase 3
0.6738	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7458	Discontinued
0.6722	Remote Similarity	NPD2796	Approved
0.672	Remote Similarity	NPD920	Approved
0.6705	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8469	Approved
0.6667	Remote Similarity	NPD8407	Phase 2
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD1510	Phase 2
0.6651	Remote Similarity	NPD8404	Phase 2
0.6648	Remote Similarity	NPD6651	Approved
0.663	Remote Similarity	NPD2935	Discontinued
0.6613	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD1243	Approved
0.66	Remote Similarity	NPD8368	Discontinued
0.6597	Remote Similarity	NPD5760	Phase 2
0.6597	Remote Similarity	NPD5761	Phase 2
0.6589	Remote Similarity	NPD7585	Approved
0.6575	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1607	Approved
0.6543	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7583	Approved
0.6531	Remote Similarity	NPD7229	Phase 3
0.6524	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7985	Registered
0.6509	Remote Similarity	NPD3533	Approved
0.6509	Remote Similarity	NPD2972	Approved
0.6509	Remote Similarity	NPD2491	Approved
0.6505	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD5676	Approved
0.6493	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3748	Approved
0.6471	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD2403	Approved
0.6461	Remote Similarity	NPD4625	Phase 3
0.6458	Remote Similarity	NPD6844	Discontinued
0.645	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7048	Phase 3
0.6448	Remote Similarity	NPD1551	Phase 2
0.6444	Remote Similarity	NPD1240	Approved
0.6432	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD3448	Approved
0.6432	Remote Similarity	NPD3057	Approved
0.6425	Remote Similarity	NPD2313	Discontinued
0.6422	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD3300	Phase 2
0.6413	Remote Similarity	NPD2344	Approved
0.6411	Remote Similarity	NPD4363	Phase 3
0.6411	Remote Similarity	NPD4360	Phase 2
0.6409	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD5124	Phase 1
0.64	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7033	Discontinued
0.6386	Remote Similarity	NPD5953	Discontinued
0.6378	Remote Similarity	NPD2424	Discontinued
0.6377	Remote Similarity	NPD4287	Approved
0.6377	Remote Similarity	NPD8361	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