NPASS Compound

Structure

NPC70318 OpenBabel07101718182D 40 46 0 0 1 0 0 0 0 0999 V2000 1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5890 -5.2958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4123 -5.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.8820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5394 -0.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5024 -3.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4641 -4.4326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1756 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7099 -2.7335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0656 -4.0340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8047 -3.7516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1059 -4.2669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0843 -3.3715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1421 -3.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3766 -3.6618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6849 -3.2344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6710 -2.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -0.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6335 -2.0753 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7688 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6954 -2.5636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9540 -4.4931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5917 -3.2457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7511 -4.7502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7512 -5.0308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 0.3820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5126 -1.5986 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 2 11 1 0 0 0 0 3 36 1 0 0 0 0 4 37 1 0 0 0 0 5 38 1 0 0 0 0 6 39 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 29 1 0 0 0 0 10 1 1 1 0 0 0 10 40 1 0 0 0 0 11 31 2 0 0 0 0 12 16 1 0 0 0 0 12 32 1 0 0 0 0 13 17 1 0 0 0 0 13 33 1 0 0 0 0 14 18 2 0 0 0 0 14 36 1 0 0 0 0 15 19 2 0 0 0 0 15 37 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 24 27 2 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 34 2 0 0 0 0 26 28 1 0 0 0 0 26 35 2 0 0 0 0 27 38 1 0 0 0 0 28 29 1 6 0 0 0 28 39 1 0 0 0 0 29 30 1 1 0 0 0 30 11 1 1 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.09
Volume:	340.524
LogP:	3.562
LogD:	3.05
LogS:	-4.741
# Rotatable Bonds:	4
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	2.531
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.974
MDCK Permeability:	8.095064004010055e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.112
30% Bioavailability (F30%):	0.588

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	97.41300201416016%
Volume Distribution (VD):	0.642
Pgp-substrate:	3.573577404022217%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.897
CYP2C19-inhibitor:	0.232
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.54
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.375
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.526
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	9.827
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.644
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.901
Carcinogencity:	0.059
Eye Corrosion:	0.021
Eye Irritation:	0.939
Respiratory Toxicity:	0.615

Download Data

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

Natural Product: NPC70318

Natural Product ID:	NPC70318
*Common Name:**	Phaeosphaerin B
IUPAC Name:	n.a.
Synonyms:	Phaeosphaerin B
Standard InCHIKey:	FAEMLLNCUQWZAR-BGUSSPSCSA-N
Standard InCHI:	InChI=1S/C30H26O10/c1-10-9-29-23-21-17(26(35)28(29)39-6)13(33)8-15(37-4)19(21)18-14(36-3)7-12(32)16-20(18)22(23)24(27(38-5)25(16)34)30(29,40-10)11(2)31/h7-8,10,28,32-33H,9H2,1-6H3/t10-,28+,29+,30-/m0/s1
SMILES:	C[C@H]1C[C@@]23c4c5c(c(cc(c5c5c(cc(c6c5c4C(=C(C6=O)OC)[C@]3(C(=O)C)O1)O)OC)OC)O)C(=O)[C@H]2OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011655
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002903] Perylenequinones

*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
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18570471]
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276650]
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	isolated from living stems and leaves of a Sedum sp.	Motilleja, Albacete, Spain	n.a.	PMID[23259972]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	2420.0	nM	PMID[536943]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	9540.0	nM	PMID[536943]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	2670.0	nM	PMID[536943]

☑ 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 NPC70318 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	462
0.1-0.2	1802
0.2-0.3	3397
0.3-0.4	8201
0.4-0.5	10582
0.5-0.6	5167
0.6-0.7	6213
0.7-0.8	6469
0.8-0.85	380
0.85-0.9	21
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9529	High Similarity	NPC470332
0.9521	High Similarity	NPC470333
0.8908	High Similarity	NPC470334
0.8757	High Similarity	NPC219686
0.875	High Similarity	NPC228654
0.8736	High Similarity	NPC470336
0.8736	High Similarity	NPC470335
0.8647	High Similarity	NPC472261
0.8613	High Similarity	NPC470341
0.8613	High Similarity	NPC105414
0.8613	High Similarity	NPC324522
0.8613	High Similarity	NPC472058
0.8613	High Similarity	NPC234497
0.8605	High Similarity	NPC316262
0.8605	High Similarity	NPC314653
0.8596	High Similarity	NPC15374
0.8588	High Similarity	NPC313368
0.858	High Similarity	NPC474637
0.8563	High Similarity	NPC469486
0.8563	High Similarity	NPC264063
0.8529	High Similarity	NPC324736
0.8523	High Similarity	NPC131862
0.8523	High Similarity	NPC229051
0.8516	High Similarity	NPC289223
0.8497	Intermediate Similarity	NPC469664
0.848	Intermediate Similarity	NPC472060
0.848	Intermediate Similarity	NPC470810
0.848	Intermediate Similarity	NPC472052
0.848	Intermediate Similarity	NPC470342
0.848	Intermediate Similarity	NPC186325
0.8466	Intermediate Similarity	NPC118128
0.8466	Intermediate Similarity	NPC473113
0.8462	Intermediate Similarity	NPC226656
0.8462	Intermediate Similarity	NPC66508
0.8457	Intermediate Similarity	NPC473096
0.8457	Intermediate Similarity	NPC473095
0.8448	Intermediate Similarity	NPC82330
0.8448	Intermediate Similarity	NPC477835
0.8444	Intermediate Similarity	NPC182693
0.8439	Intermediate Similarity	NPC476505
0.8439	Intermediate Similarity	NPC214279
0.8439	Intermediate Similarity	NPC290160
0.843	Intermediate Similarity	NPC137232
0.843	Intermediate Similarity	NPC273467
0.843	Intermediate Similarity	NPC18380
0.843	Intermediate Similarity	NPC189552
0.8421	Intermediate Similarity	NPC472617
0.8421	Intermediate Similarity	NPC177650
0.8418	Intermediate Similarity	NPC475080
0.8412	Intermediate Similarity	NPC474360
0.8409	Intermediate Similarity	NPC315306
0.8409	Intermediate Similarity	NPC313717
0.84	Intermediate Similarity	NPC473094
0.8393	Intermediate Similarity	NPC474417
0.8393	Intermediate Similarity	NPC149526
0.8391	Intermediate Similarity	NPC472051
0.8391	Intermediate Similarity	NPC472057
0.8389	Intermediate Similarity	NPC315221
0.8382	Intermediate Similarity	NPC472059
0.8382	Intermediate Similarity	NPC315772
0.838	Intermediate Similarity	NPC478000
0.8373	Intermediate Similarity	NPC34802
0.8372	Intermediate Similarity	NPC292863
0.8372	Intermediate Similarity	NPC284495
0.8372	Intermediate Similarity	NPC184326
0.8372	Intermediate Similarity	NPC472618
0.8372	Intermediate Similarity	NPC312993
0.8371	Intermediate Similarity	NPC477991
0.8371	Intermediate Similarity	NPC477992
0.8363	Intermediate Similarity	NPC201127
0.8362	Intermediate Similarity	NPC477529
0.8362	Intermediate Similarity	NPC477836
0.8352	Intermediate Similarity	NPC54903
0.8352	Intermediate Similarity	NPC286074
0.8343	Intermediate Similarity	NPC475656
0.8343	Intermediate Similarity	NPC313452
0.8343	Intermediate Similarity	NPC475148
0.8333	Intermediate Similarity	NPC473009
0.8333	Intermediate Similarity	NPC100849
0.8333	Intermediate Similarity	NPC472053
0.8333	Intermediate Similarity	NPC470568
0.8324	Intermediate Similarity	NPC301256
0.8324	Intermediate Similarity	NPC117985
0.8324	Intermediate Similarity	NPC478134
0.8324	Intermediate Similarity	NPC312273
0.8315	Intermediate Similarity	NPC154986
0.8314	Intermediate Similarity	NPC51760
0.8314	Intermediate Similarity	NPC195167
0.8304	Intermediate Similarity	NPC180924
0.8295	Intermediate Similarity	NPC286230
0.8295	Intermediate Similarity	NPC253730
0.8294	Intermediate Similarity	NPC329844
0.8286	Intermediate Similarity	NPC472784
0.8286	Intermediate Similarity	NPC169471
0.8286	Intermediate Similarity	NPC473010
0.8284	Intermediate Similarity	NPC470569
0.8284	Intermediate Similarity	NPC230848
0.8284	Intermediate Similarity	NPC72958
0.8284	Intermediate Similarity	NPC477276
0.8284	Intermediate Similarity	NPC232645
0.8284	Intermediate Similarity	NPC478148
0.8278	Intermediate Similarity	NPC5671
0.8276	Intermediate Similarity	NPC473012
0.8276	Intermediate Similarity	NPC475106
0.8274	Intermediate Similarity	NPC198927
0.8274	Intermediate Similarity	NPC329933
0.8268	Intermediate Similarity	NPC300657
0.8266	Intermediate Similarity	NPC476506
0.8256	Intermediate Similarity	NPC164110
0.8256	Intermediate Similarity	NPC96342
0.8256	Intermediate Similarity	NPC212967
0.8256	Intermediate Similarity	NPC246647
0.8256	Intermediate Similarity	NPC272196
0.8256	Intermediate Similarity	NPC196448
0.8256	Intermediate Similarity	NPC263483
0.8242	Intermediate Similarity	NPC478001
0.8242	Intermediate Similarity	NPC228209
0.8239	Intermediate Similarity	NPC178173
0.8239	Intermediate Similarity	NPC120857
0.8239	Intermediate Similarity	NPC30027
0.8239	Intermediate Similarity	NPC85047
0.8239	Intermediate Similarity	NPC17274
0.8235	Intermediate Similarity	NPC40356
0.8235	Intermediate Similarity	NPC87708
0.8235	Intermediate Similarity	NPC154683
0.8232	Intermediate Similarity	NPC120102
0.8229	Intermediate Similarity	NPC109180
0.8229	Intermediate Similarity	NPC159508
0.8225	Intermediate Similarity	NPC119929
0.8225	Intermediate Similarity	NPC147735
0.8222	Intermediate Similarity	NPC324220
0.8222	Intermediate Similarity	NPC312630
0.8214	Intermediate Similarity	NPC472841
0.8212	Intermediate Similarity	NPC469393
0.8208	Intermediate Similarity	NPC55443
0.8208	Intermediate Similarity	NPC18699
0.8208	Intermediate Similarity	NPC295090
0.8202	Intermediate Similarity	NPC477572
0.8202	Intermediate Similarity	NPC477571
0.8202	Intermediate Similarity	NPC477573
0.8198	Intermediate Similarity	NPC146211
0.8192	Intermediate Similarity	NPC95715
0.8192	Intermediate Similarity	NPC193222
0.8187	Intermediate Similarity	NPC169990
0.8187	Intermediate Similarity	NPC472211
0.8187	Intermediate Similarity	NPC210942
0.8187	Intermediate Similarity	NPC214632
0.8187	Intermediate Similarity	NPC208806
0.8182	Intermediate Similarity	NPC472049
0.8177	Intermediate Similarity	NPC477683
0.8177	Intermediate Similarity	NPC477682
0.8177	Intermediate Similarity	NPC77179
0.8177	Intermediate Similarity	NPC246877
0.8177	Intermediate Similarity	NPC23553
0.8171	Intermediate Similarity	NPC473022
0.8171	Intermediate Similarity	NPC478229
0.8171	Intermediate Similarity	NPC193998
0.8171	Intermediate Similarity	NPC472402
0.8171	Intermediate Similarity	NPC473011
0.8167	Intermediate Similarity	NPC475398
0.8166	Intermediate Similarity	NPC97028
0.8166	Intermediate Similarity	NPC288036
0.8166	Intermediate Similarity	NPC158338
0.8166	Intermediate Similarity	NPC97029
0.8166	Intermediate Similarity	NPC65589
0.8166	Intermediate Similarity	NPC100985
0.8166	Intermediate Similarity	NPC80370
0.8156	Intermediate Similarity	NPC169018
0.8156	Intermediate Similarity	NPC478002
0.8156	Intermediate Similarity	NPC91650
0.8155	Intermediate Similarity	NPC245584
0.8155	Intermediate Similarity	NPC56433
0.8155	Intermediate Similarity	NPC312929
0.8155	Intermediate Similarity	NPC289042
0.8155	Intermediate Similarity	NPC118027
0.8155	Intermediate Similarity	NPC126767
0.8155	Intermediate Similarity	NPC190648
0.815	Intermediate Similarity	NPC158542
0.815	Intermediate Similarity	NPC282390
0.815	Intermediate Similarity	NPC268360
0.815	Intermediate Similarity	NPC281137
0.8146	Intermediate Similarity	NPC20734
0.8146	Intermediate Similarity	NPC300307
0.8144	Intermediate Similarity	NPC12402
0.8144	Intermediate Similarity	NPC28632
0.8142	Intermediate Similarity	NPC8927
0.814	Intermediate Similarity	NPC254351
0.814	Intermediate Similarity	NPC182555
0.814	Intermediate Similarity	NPC148938
0.814	Intermediate Similarity	NPC300668
0.814	Intermediate Similarity	NPC66441
0.814	Intermediate Similarity	NPC68727
0.814	Intermediate Similarity	NPC134171
0.8136	Intermediate Similarity	NPC475109
0.8136	Intermediate Similarity	NPC62444
0.8136	Intermediate Similarity	NPC251336
0.8136	Intermediate Similarity	NPC53640
0.8136	Intermediate Similarity	NPC476056
0.8136	Intermediate Similarity	NPC476255
0.8133	Intermediate Similarity	NPC84266

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 NPC70318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	988
0.2-0.3	1834
0.3-0.4	2775
0.4-0.5	1951
0.5-0.6	797
0.6-0.7	291
0.7-0.8	113
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8647	High Similarity	NPD6959	Discontinued
0.8035	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7390	Discontinued
0.7966	Intermediate Similarity	NPD6232	Discontinued
0.7933	Intermediate Similarity	NPD7473	Discontinued
0.7929	Intermediate Similarity	NPD2533	Approved
0.7929	Intermediate Similarity	NPD2532	Approved
0.7929	Intermediate Similarity	NPD2534	Approved
0.7877	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6166	Phase 2
0.7759	Intermediate Similarity	NPD7411	Suspended
0.7738	Intermediate Similarity	NPD2800	Approved
0.7719	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4380	Phase 2
0.767	Intermediate Similarity	NPD7819	Suspended
0.767	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3749	Approved
0.764	Intermediate Similarity	NPD7075	Discontinued
0.7584	Intermediate Similarity	NPD3882	Suspended
0.7554	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD5844	Phase 1
0.7543	Intermediate Similarity	NPD3226	Approved
0.7527	Intermediate Similarity	NPD6559	Discontinued
0.7526	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7768	Phase 2
0.7472	Intermediate Similarity	NPD5761	Phase 2
0.7472	Intermediate Similarity	NPD5760	Phase 2
0.7472	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5494	Approved
0.7449	Intermediate Similarity	NPD6780	Approved
0.7449	Intermediate Similarity	NPD6778	Approved
0.7449	Intermediate Similarity	NPD6776	Approved
0.7449	Intermediate Similarity	NPD6782	Approved
0.7449	Intermediate Similarity	NPD6781	Approved
0.7449	Intermediate Similarity	NPD6777	Approved
0.7449	Intermediate Similarity	NPD6779	Approved
0.7424	Intermediate Similarity	NPD7435	Discontinued
0.7416	Intermediate Similarity	NPD1934	Approved
0.7412	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1510	Phase 2
0.7389	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7870	Phase 2
0.7387	Intermediate Similarity	NPD7871	Phase 2
0.7381	Intermediate Similarity	NPD1607	Approved
0.7381	Intermediate Similarity	NPD6651	Approved
0.738	Intermediate Similarity	NPD6797	Phase 2
0.738	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5710	Approved
0.7377	Intermediate Similarity	NPD5711	Approved
0.7368	Intermediate Similarity	NPD1549	Phase 2
0.7368	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7251	Discontinued
0.7337	Intermediate Similarity	NPD7697	Approved
0.7337	Intermediate Similarity	NPD7696	Phase 3
0.7337	Intermediate Similarity	NPD7698	Approved
0.7337	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3817	Phase 2
0.733	Intermediate Similarity	NPD8150	Discontinued
0.7327	Intermediate Similarity	NPD8151	Discontinued
0.7322	Intermediate Similarity	NPD1247	Approved
0.7314	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3751	Discontinued
0.7312	Intermediate Similarity	NPD3818	Discontinued
0.7308	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7808	Phase 3
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7283	Intermediate Similarity	NPD7003	Approved
0.7278	Intermediate Similarity	NPD2801	Approved
0.7273	Intermediate Similarity	NPD1512	Approved
0.7273	Intermediate Similarity	NPD6273	Approved
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7262	Intermediate Similarity	NPD1240	Approved
0.7253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6100	Approved
0.7251	Intermediate Similarity	NPD2796	Approved
0.7251	Intermediate Similarity	NPD6099	Approved
0.724	Intermediate Similarity	NPD8434	Phase 2
0.7238	Intermediate Similarity	NPD5402	Approved
0.7234	Intermediate Similarity	NPD7074	Phase 3
0.7225	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6234	Discontinued
0.7211	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7874	Approved
0.7198	Intermediate Similarity	NPD4966	Approved
0.7198	Intermediate Similarity	NPD4965	Approved
0.7198	Intermediate Similarity	NPD4967	Phase 2
0.7194	Intermediate Similarity	NPD6535	Approved
0.7194	Intermediate Similarity	NPD6534	Approved
0.7192	Intermediate Similarity	NPD7701	Phase 2
0.7184	Intermediate Similarity	NPD3750	Approved
0.7181	Intermediate Similarity	NPD7054	Approved
0.7159	Intermediate Similarity	NPD6799	Approved
0.7159	Intermediate Similarity	NPD1511	Approved
0.7151	Intermediate Similarity	NPD5404	Approved
0.7151	Intermediate Similarity	NPD5406	Approved
0.7151	Intermediate Similarity	NPD3926	Phase 2
0.7151	Intermediate Similarity	NPD5405	Approved
0.7151	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD7472	Approved
0.7135	Intermediate Similarity	NPD7199	Phase 2
0.7135	Intermediate Similarity	NPD920	Approved
0.7128	Intermediate Similarity	NPD7799	Discontinued
0.7128	Intermediate Similarity	NPD7228	Approved
0.7127	Intermediate Similarity	NPD37	Approved
0.7102	Intermediate Similarity	NPD7236	Approved
0.7097	Intermediate Similarity	NPD7229	Phase 3
0.7095	Intermediate Similarity	NPD7239	Suspended
0.7088	Intermediate Similarity	NPD1465	Phase 2
0.7087	Intermediate Similarity	NPD7801	Approved
0.7086	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7700	Phase 2
0.7085	Intermediate Similarity	NPD7699	Phase 2
0.7068	Intermediate Similarity	NPD6764	Approved
0.7068	Intermediate Similarity	NPD6765	Approved
0.7056	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7458	Discontinued
0.7052	Intermediate Similarity	NPD2935	Discontinued
0.7044	Intermediate Similarity	NPD8319	Approved
0.7044	Intermediate Similarity	NPD8320	Phase 1
0.7039	Intermediate Similarity	NPD5403	Approved
0.703	Intermediate Similarity	NPD6823	Phase 2
0.7027	Intermediate Similarity	NPD919	Approved
0.7021	Intermediate Similarity	NPD2403	Approved
0.7011	Intermediate Similarity	NPD2346	Discontinued
0.7011	Intermediate Similarity	NPD2344	Approved
0.7011	Intermediate Similarity	NPD1471	Phase 3
0.7005	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7783	Phase 2
0.6948	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1243	Approved
0.6927	Remote Similarity	NPD5401	Approved
0.6927	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6785	Approved
0.6923	Remote Similarity	NPD6784	Approved
0.6897	Remote Similarity	NPD3748	Approved
0.6893	Remote Similarity	NPD4628	Phase 3
0.6882	Remote Similarity	NPD4625	Phase 3
0.6866	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7177	Discontinued
0.6857	Remote Similarity	NPD1551	Phase 2
0.6854	Remote Similarity	NPD2309	Approved
0.6851	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3764	Approved
0.6842	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5953	Discontinued
0.6831	Remote Similarity	NPD7028	Phase 2
0.6823	Remote Similarity	NPD7286	Phase 2
0.6818	Remote Similarity	NPD4287	Approved
0.6816	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7685	Pre-registration
0.6804	Remote Similarity	NPD7240	Approved
0.6772	Remote Similarity	NPD8127	Discontinued
0.6748	Remote Similarity	NPD7497	Discontinued
0.6746	Remote Similarity	NPD1470	Approved
0.6744	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7057	Phase 3
0.6738	Remote Similarity	NPD7058	Phase 2
0.6725	Remote Similarity	NPD4908	Phase 1
0.6716	Remote Similarity	NPD6212	Phase 3
0.6716	Remote Similarity	NPD6213	Phase 3
0.6716	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8285	Discontinued
0.6713	Remote Similarity	NPD7907	Approved
0.6707	Remote Similarity	NPD1201	Approved
0.6705	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6663	Approved
0.6705	Remote Similarity	NPD2799	Discontinued
0.6704	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4360	Phase 2
0.6683	Remote Similarity	NPD4363	Phase 3
0.6667	Remote Similarity	NPD943	Approved
0.6667	Remote Similarity	NPD7930	Approved
0.6667	Remote Similarity	NPD6190	Approved
0.665	Remote Similarity	NPD2493	Approved
0.665	Remote Similarity	NPD2494	Approved
0.6647	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD8455	Phase 2
0.6629	Remote Similarity	NPD5762	Approved
0.6629	Remote Similarity	NPD5763	Approved
0.6629	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6005	Phase 3

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