NPASS Compound

Structure

NPC471335 OpenBabel07101718192D 44 47 0 0 1 0 0 0 0 0999 V2000 3.6026 -2.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5622 1.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5109 -4.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9839 0.1786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5622 -2.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 -1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9192 -1.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5622 0.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 -3.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 0.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7370 -0.4794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8831 -2.0662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0109 -3.7976 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.5327 -4.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 -0.4612 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3417 -3.0544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6921 -1.4784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 1.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9641 -0.4612 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 2.5388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.6565 -0.0864 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.0617 -3.0501 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -9.0054 -3.6930 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -5.5622 -1.9612 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7896 -5.1248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2942 0.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5497 -2.0763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5727 -1.9522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 1.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5261 -0.8806 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 1 41 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 34 1 0 0 0 0 4 42 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 15 2 0 0 0 0 7 18 1 0 0 0 0 7 19 1 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 33 1 0 0 0 0 10 20 1 0 0 0 0 10 33 1 0 0 0 0 11 17 2 0 0 0 0 11 43 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 24 2 0 0 0 0 14 28 1 0 0 0 0 15 24 1 0 0 0 0 15 29 1 0 0 0 0 16 23 2 0 0 0 0 16 30 1 0 0 0 0 17 23 1 0 0 0 0 17 31 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 0 0 0 0 19 36 2 0 0 0 0 20 37 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 21 35 2 0 0 0 0 22 38 2 0 0 0 0 23 41 1 0 0 0 0 24 42 1 0 0 0 0 25 27 1 6 0 0 0 25 39 1 0 0 0 0 26 34 1 0 0 0 0 26 40 2 0 0 0 0 27 8 1 6 0 0 0 27 43 1 0 0 0 0 27 44 1 0 0 0 0 35 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	886.81
Volume:	619.406
LogP:	3.333
LogD:	1.236
LogS:	-2.38
# Rotatable Bonds:	12
TPSA:	161.85
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.128
Synthetic Accessibility Score:	5.881
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.071
MDCK Permeability:	1.5841809727135114e-05
Pgp-inhibitor:	0.913
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.763
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	95.85608673095703%
Volume Distribution (VD):	0.823
Pgp-substrate:	6.351788520812988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	0.547
CYP2C19-substrate:	0.724
CYP2C9-inhibitor:	0.582
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.96
CYP3A4-substrate:	0.866

ADMET: Excretion

Clearance (CL):	1.481
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.148
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.883
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.992
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.348
Carcinogencity:	0.662
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC471335

Natural Product ID:	NPC471335
*Common Name:**	19-Hydroxypsammaplysine X
IUPAC Name:	(4S,5S)-7,9-dibromo-N-[3-[2,6-dibromo-4-[2-[[(Z)-(3-chloro-2,5-dioxocyclopentylidene)methyl]amino]-1-hydroxyethyl]phenoxy]propyl]-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
Synonyms:
Standard InCHIKey:	FGYQWPOMHRREQY-ILXFYYIXSA-N
Standard InCHI:	InChI=1S/C27H26Br4ClN3O9/c1-41-23-16(30)8-27(43-11-17(23)31)25(39)21(35-44-27)26(40)34-3-2-4-42-24-14(28)5-12(6-15(24)29)20(37)10-33-9-13-19(36)7-18(32)22(13)38/h5-6,9,11,18,20,25,33,37,39H,2-4,7-8,10H2,1H3,(H,34,40)/b13-9-/t18?,20?,25-,27-/m0/s1
SMILES:	COC1=C(Br)C[C@]2(OC=C1Br)ON=C([C@@H]2O)C(=O)NCCCOc1c(Br)cc(cc1Br)C(CN/C=C1/C(=O)CC(C1=O)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419314
PubChem CID:	73346123
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473442]
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964644]

☑ 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
GI50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	=	3500.0	nM	PMID[515890]
NPT2477	Cell Line	NUGC-3	Homo sapiens	GI50	=	4000.0	nM	PMID[515890]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	800.0	nM	PMID[515890]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	2500.0	nM	PMID[515890]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	2100.0	nM	PMID[515890]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	3500.0	nM	PMID[515890]

☑ 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 NPC471335 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	299
0.1-0.2	1821
0.2-0.3	9328
0.3-0.4	10042
0.4-0.5	18360
0.5-0.6	2690
0.6-0.7	129
0.7-0.8	12
0.8-0.85	7
0.85-0.9	5
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9634	High Similarity	NPC471339
0.933	High Similarity	NPC471336
0.933	High Similarity	NPC470746
0.9005	High Similarity	NPC475843
0.8969	High Similarity	NPC123140
0.8953	High Similarity	NPC471338
0.8953	High Similarity	NPC474678
0.8776	High Similarity	NPC471337
0.8639	High Similarity	NPC121571
0.8639	High Similarity	NPC8093
0.8063	Intermediate Similarity	NPC477255
0.798	Intermediate Similarity	NPC77435
0.798	Intermediate Similarity	NPC259071
0.7882	Intermediate Similarity	NPC202866
0.7879	Intermediate Similarity	NPC477254
0.7833	Intermediate Similarity	NPC227953
0.7586	Intermediate Similarity	NPC174607
0.7549	Intermediate Similarity	NPC147847
0.7202	Intermediate Similarity	NPC469711
0.7005	Intermediate Similarity	NPC156311
0.6814	Remote Similarity	NPC326027
0.68	Remote Similarity	NPC326333
0.6754	Remote Similarity	NPC474673
0.675	Remote Similarity	NPC233926
0.6717	Remote Similarity	NPC258222
0.6699	Remote Similarity	NPC143450
0.6683	Remote Similarity	NPC47672
0.6667	Remote Similarity	NPC248822
0.6636	Remote Similarity	NPC323662
0.6632	Remote Similarity	NPC128877
0.6615	Remote Similarity	NPC308571
0.6583	Remote Similarity	NPC76412
0.6577	Remote Similarity	NPC473450
0.655	Remote Similarity	NPC109968
0.653	Remote Similarity	NPC328763
0.6528	Remote Similarity	NPC475658
0.6528	Remote Similarity	NPC473892
0.6522	Remote Similarity	NPC209463
0.6498	Remote Similarity	NPC82741
0.6498	Remote Similarity	NPC246591
0.6498	Remote Similarity	NPC473409
0.6498	Remote Similarity	NPC141405
0.6482	Remote Similarity	NPC71629
0.6452	Remote Similarity	NPC471591
0.6435	Remote Similarity	NPC92235
0.6425	Remote Similarity	NPC80514
0.6414	Remote Similarity	NPC78530
0.6409	Remote Similarity	NPC102245
0.6406	Remote Similarity	NPC49172
0.64	Remote Similarity	NPC296085
0.6381	Remote Similarity	NPC471568
0.6381	Remote Similarity	NPC473693
0.6368	Remote Similarity	NPC469731
0.6351	Remote Similarity	NPC469721
0.6335	Remote Similarity	NPC64066
0.6332	Remote Similarity	NPC135349
0.6327	Remote Similarity	NPC214368
0.6316	Remote Similarity	NPC469479
0.6313	Remote Similarity	NPC474128
0.6308	Remote Similarity	NPC470471
0.6306	Remote Similarity	NPC65714
0.6303	Remote Similarity	NPC196091
0.6301	Remote Similarity	NPC96275
0.6284	Remote Similarity	NPC299806
0.6256	Remote Similarity	NPC186617
0.625	Remote Similarity	NPC470472
0.6245	Remote Similarity	NPC81845
0.6244	Remote Similarity	NPC235033
0.6244	Remote Similarity	NPC470470
0.6244	Remote Similarity	NPC471235
0.6244	Remote Similarity	NPC283207
0.6244	Remote Similarity	NPC73132
0.6237	Remote Similarity	NPC247018
0.6237	Remote Similarity	NPC307123
0.6237	Remote Similarity	NPC97870
0.6222	Remote Similarity	NPC471592
0.6221	Remote Similarity	NPC475396
0.6193	Remote Similarity	NPC74618
0.6193	Remote Similarity	NPC301941
0.6193	Remote Similarity	NPC214188
0.618	Remote Similarity	NPC295795
0.6179	Remote Similarity	NPC469505
0.6171	Remote Similarity	NPC230539
0.6157	Remote Similarity	NPC469979
0.6157	Remote Similarity	NPC226001
0.6154	Remote Similarity	NPC80337
0.6129	Remote Similarity	NPC298981
0.6129	Remote Similarity	NPC207819
0.6129	Remote Similarity	NPC110454
0.6129	Remote Similarity	NPC473462
0.6129	Remote Similarity	NPC126128
0.6127	Remote Similarity	NPC324081
0.6126	Remote Similarity	NPC272463
0.6123	Remote Similarity	NPC477550
0.6123	Remote Similarity	NPC477552
0.6101	Remote Similarity	NPC290534
0.6096	Remote Similarity	NPC123859
0.6094	Remote Similarity	NPC110131
0.6081	Remote Similarity	NPC144823
0.607	Remote Similarity	NPC242728
0.607	Remote Similarity	NPC204546
0.607	Remote Similarity	NPC477551
0.6063	Remote Similarity	NPC315542
0.6055	Remote Similarity	NPC475421
0.6045	Remote Similarity	NPC167763
0.6045	Remote Similarity	NPC470903
0.6045	Remote Similarity	NPC470112
0.6038	Remote Similarity	NPC158900
0.6037	Remote Similarity	NPC225130
0.6036	Remote Similarity	NPC276120
0.6009	Remote Similarity	NPC144314
0.6009	Remote Similarity	NPC254700
0.6	Remote Similarity	NPC213471
0.5991	Remote Similarity	NPC471165
0.5983	Remote Similarity	NPC50548
0.5983	Remote Similarity	NPC219350
0.5983	Remote Similarity	NPC194699
0.5971	Remote Similarity	NPC20755
0.597	Remote Similarity	NPC40321
0.5965	Remote Similarity	NPC149962
0.5962	Remote Similarity	NPC472923
0.5956	Remote Similarity	NPC223384
0.5952	Remote Similarity	NPC56635
0.5948	Remote Similarity	NPC311357
0.5933	Remote Similarity	NPC123011
0.5933	Remote Similarity	NPC256689
0.5933	Remote Similarity	NPC470710
0.5931	Remote Similarity	NPC476661
0.5929	Remote Similarity	NPC477526
0.5928	Remote Similarity	NPC320242
0.5921	Remote Similarity	NPC59827
0.5921	Remote Similarity	NPC184933
0.5919	Remote Similarity	NPC138083
0.5917	Remote Similarity	NPC67658
0.5909	Remote Similarity	NPC474753
0.5907	Remote Similarity	NPC197125
0.5905	Remote Similarity	NPC476662
0.5905	Remote Similarity	NPC156055
0.5899	Remote Similarity	NPC328494
0.5899	Remote Similarity	NPC89831
0.5897	Remote Similarity	NPC14339
0.5896	Remote Similarity	NPC476194
0.5896	Remote Similarity	NPC471203
0.5888	Remote Similarity	NPC63931
0.5882	Remote Similarity	NPC277306
0.5882	Remote Similarity	NPC469442
0.5872	Remote Similarity	NPC248670
0.587	Remote Similarity	NPC281629
0.5865	Remote Similarity	NPC293347
0.5865	Remote Similarity	NPC477160
0.5862	Remote Similarity	NPC470709
0.5859	Remote Similarity	NPC475735
0.5859	Remote Similarity	NPC473724
0.585	Remote Similarity	NPC303993
0.585	Remote Similarity	NPC470441
0.5847	Remote Similarity	NPC79130
0.5844	Remote Similarity	NPC477527
0.5841	Remote Similarity	NPC471395
0.5841	Remote Similarity	NPC124626
0.5837	Remote Similarity	NPC175150
0.5837	Remote Similarity	NPC243633
0.5837	Remote Similarity	NPC475615
0.5833	Remote Similarity	NPC25539
0.5833	Remote Similarity	NPC473502
0.5829	Remote Similarity	NPC470392
0.5826	Remote Similarity	NPC308709
0.5818	Remote Similarity	NPC477115
0.5815	Remote Similarity	NPC29531
0.5811	Remote Similarity	NPC32064
0.581	Remote Similarity	NPC39431
0.5808	Remote Similarity	NPC474091
0.5808	Remote Similarity	NPC474087
0.5802	Remote Similarity	NPC185172
0.58	Remote Similarity	NPC169766
0.58	Remote Similarity	NPC132308
0.5799	Remote Similarity	NPC273755
0.5797	Remote Similarity	NPC313414
0.5796	Remote Similarity	NPC94862
0.5796	Remote Similarity	NPC34780
0.5794	Remote Similarity	NPC471031
0.5794	Remote Similarity	NPC469689
0.5792	Remote Similarity	NPC473052
0.5792	Remote Similarity	NPC477665
0.5792	Remote Similarity	NPC473055
0.5789	Remote Similarity	NPC473378
0.5789	Remote Similarity	NPC473407
0.5787	Remote Similarity	NPC71205
0.5783	Remote Similarity	NPC322424
0.5782	Remote Similarity	NPC476268
0.5782	Remote Similarity	NPC244509
0.578	Remote Similarity	NPC46009
0.5778	Remote Similarity	NPC235194
0.5778	Remote Similarity	NPC128683
0.5778	Remote Similarity	NPC206061
0.5775	Remote Similarity	NPC287757
0.5775	Remote Similarity	NPC319320
0.5774	Remote Similarity	NPC14390
0.5773	Remote Similarity	NPC164608
0.5773	Remote Similarity	NPC26108
0.5771	Remote Similarity	NPC470951

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 NPC471335 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	621
0.2-0.3	1537
0.3-0.4	2772
0.4-0.5	3231
0.5-0.6	802
0.6-0.7	15
0.7-0.8	0
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
0.6372	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD2239	Approved
0.6294	Remote Similarity	NPD2240	Approved
0.6261	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD3153	Approved
0.6256	Remote Similarity	NPD3154	Approved
0.6237	Remote Similarity	NPD1423	Approved
0.6207	Remote Similarity	NPD3536	Discontinued
0.6202	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.615	Remote Similarity	NPD7608	Discontinued
0.6134	Remote Similarity	NPD3180	Approved
0.6134	Remote Similarity	NPD3179	Approved
0.6132	Remote Similarity	NPD8059	Phase 3
0.6132	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6863	Phase 2
0.6081	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4661	Approved
0.6049	Remote Similarity	NPD4662	Approved
0.6039	Remote Similarity	NPD3686	Approved
0.6039	Remote Similarity	NPD3687	Approved
0.6038	Remote Similarity	NPD8031	Discontinued
0.6037	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4466	Phase 1
0.6009	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7039	Approved
0.6	Remote Similarity	NPD7038	Approved
0.5991	Remote Similarity	NPD3366	Approved
0.599	Remote Similarity	NPD7131	Phase 3
0.598	Remote Similarity	NPD3054	Approved
0.598	Remote Similarity	NPD3052	Approved
0.5973	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD7972	Discontinued
0.597	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7811	Phase 3
0.5957	Remote Similarity	NPD7810	Phase 3
0.5953	Remote Similarity	NPD7485	Phase 3
0.5953	Remote Similarity	NPD7484	Phase 3
0.5943	Remote Similarity	NPD7318	Phase 3
0.5935	Remote Similarity	NPD6315	Phase 2
0.5933	Remote Similarity	NPD2649	Approved
0.5933	Remote Similarity	NPD2651	Approved
0.5928	Remote Similarity	NPD1817	Approved
0.5928	Remote Similarity	NPD1820	Approved
0.5928	Remote Similarity	NPD1819	Approved
0.5928	Remote Similarity	NPD1298	Discontinued
0.5928	Remote Similarity	NPD1818	Approved
0.5921	Remote Similarity	NPD7256	Discontinued
0.5898	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD3985	Discontinued
0.5888	Remote Similarity	NPD9718	Approved
0.5888	Remote Similarity	NPD3165	Approved
0.5888	Remote Similarity	NPD3164	Approved
0.5888	Remote Similarity	NPD3167	Approved
0.5888	Remote Similarity	NPD3166	Approved
0.5885	Remote Similarity	NPD4258	Approved
0.5885	Remote Similarity	NPD4259	Approved
0.5877	Remote Similarity	NPD6677	Suspended
0.5877	Remote Similarity	NPD6072	Discontinued
0.5857	Remote Similarity	NPD3769	Discontinued
0.5849	Remote Similarity	NPD7317	Phase 3
0.5847	Remote Similarity	NPD7584	Approved
0.5837	Remote Similarity	NPD7476	Discontinued
0.5833	Remote Similarity	NPD4666	Phase 3
0.5829	Remote Similarity	NPD3163	Approved
0.5829	Remote Similarity	NPD3162	Approved
0.5826	Remote Similarity	NPD2215	Approved
0.5826	Remote Similarity	NPD2216	Approved
0.5825	Remote Similarity	NPD2677	Approved
0.5822	Remote Similarity	NPD5772	Approved
0.5822	Remote Similarity	NPD5773	Approved
0.5819	Remote Similarity	NPD7565	Approved
0.5818	Remote Similarity	NPD2163	Approved
0.5818	Remote Similarity	NPD6620	Discovery
0.5817	Remote Similarity	NPD3158	Phase 1
0.5817	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD3157	Approved
0.5815	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.5813	Remote Similarity	NPD1725	Approved
0.5805	Remote Similarity	NPD4162	Approved
0.5802	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD3933	Discontinued
0.5792	Remote Similarity	NPD5095	Phase 3
0.5792	Remote Similarity	NPD5096	Phase 3
0.5789	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD5709	Phase 3
0.5779	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5557	Phase 1
0.5765	Remote Similarity	NPD1794	Approved
0.5765	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.576	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.576	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD2388	Discontinued
0.5748	Remote Similarity	NPD2977	Approved
0.5748	Remote Similarity	NPD2978	Approved
0.5742	Remote Similarity	NPD6419	Discontinued
0.5735	Remote Similarity	NPD4210	Discontinued
0.5728	Remote Similarity	NPD2459	Approved
0.5728	Remote Similarity	NPD3060	Approved
0.5728	Remote Similarity	NPD2458	Approved
0.5728	Remote Similarity	NPD2460	Phase 3
0.5726	Remote Similarity	NPD6519	Phase 2
0.5726	Remote Similarity	NPD7827	Phase 1
0.5721	Remote Similarity	NPD2296	Approved
0.5721	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7583	Approved
0.5714	Remote Similarity	NPD2183	Approved
0.5714	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2184	Approved
0.5714	Remote Similarity	NPD2186	Approved
0.5702	Remote Similarity	NPD4157	Discontinued
0.5701	Remote Similarity	NPD5356	Approved
0.5701	Remote Similarity	NPD5355	Approved
0.5696	Remote Similarity	NPD7296	Approved
0.5694	Remote Similarity	NPD1774	Approved
0.569	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.569	Remote Similarity	NPD4361	Phase 2
0.569	Remote Similarity	NPD7585	Approved
0.5688	Remote Similarity	NPD2904	Discontinued
0.5687	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD5137	Approved
0.5678	Remote Similarity	NPD6823	Phase 2
0.5677	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3909	Discontinued
0.5674	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD5745	Approved
0.5667	Remote Similarity	NPD2874	Phase 2
0.566	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD2161	Phase 2
0.5658	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.565	Remote Similarity	NPD42	Phase 2
0.565	Remote Similarity	NPD5163	Phase 2
0.565	Remote Similarity	NPD6042	Phase 2
0.5649	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.564	Remote Similarity	NPD52	Approved
0.564	Remote Similarity	NPD7526	Approved
0.564	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD6851	Approved
0.5639	Remote Similarity	NPD6853	Approved
0.5631	Remote Similarity	NPD5605	Phase 2
0.5631	Remote Similarity	NPD7978	Discontinued
0.563	Remote Similarity	NPD7891	Discontinued
0.5628	Remote Similarity	NPD3819	Phase 2
0.5628	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD2250	Discontinued
0.5625	Remote Similarity	NPD2325	Approved
0.5622	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.562	Remote Similarity	NPD7801	Approved
0.5619	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD8469	Approved
0.5612	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.5611	Remote Similarity	NPD644	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD6681	Discovery
0.5604	Remote Similarity	NPD7153	Discontinued
0.5604	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6297	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