NPASS Compound

Natural Product: NPC604706

Natural Product ID	NPC604706
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WPYOCTODIOSRQG-WOXDTIJASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL4447109
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 108111 0 0 0 0 0 0 0 0999 V2000 -4.5249 4.5700 -0.7672 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8611 3.7803 0.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0041 4.4516 1.2370 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7498 3.5753 1.3786 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 2.8612 1.0043 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7507 3.4172 -0.0386 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3900 3.0578 -0.2185 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0875 2.0908 0.5404 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6321 3.6116 -1.1163 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2345 4.2912 -2.3495 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6124 5.5342 -2.1870 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4009 3.3544 -3.3709 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6368 2.6091 -1.3630 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5127 2.0810 -0.4159 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4174 2.5163 0.7128 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5437 1.0010 -0.7224 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7120 1.6168 -1.3455 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4353 2.6740 -0.5932 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5845 3.1769 -1.5048 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1418 2.1014 0.6191 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6596 0.2633 0.4888 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7751 -0.8188 0.7119 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9788 -1.0072 -0.2172 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6977 -1.7124 1.8917 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9502 -2.4619 2.1878 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3980 -3.3449 1.1086 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2529 -2.9196 0.1148 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6610 -3.7849 -0.8997 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2217 -5.0864 -0.9367 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3677 -5.5191 0.0526 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9603 -4.6492 1.0685 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5313 -2.5833 1.7330 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3234 -2.4042 2.4415 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4227 -1.4704 3.2622 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9066 -3.2170 2.2425 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7224 -4.6777 2.2988 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6432 -5.1617 1.1931 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5915 -4.0025 0.1734 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5685 -2.8680 0.9884 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9759 -1.5379 0.7996 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6075 -0.7974 1.7732 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7063 -0.8823 -0.2846 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2032 -1.1094 -0.2852 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6379 -2.5059 -0.4080 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8606 -3.2813 0.7091 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2808 -4.5907 0.6060 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4886 -5.1576 -0.6261 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2737 -4.4061 -1.7622 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8526 -3.0943 -1.6471 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4563 0.5716 -0.2183 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8414 1.3869 0.8209 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5169 0.8635 1.7127 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1422 4.0053 -1.6347 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8839 5.4418 -0.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5202 5.0503 -1.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2642 2.7762 0.0805 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4464 5.2055 0.5663 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6285 4.9308 2.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7962 3.6993 1.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1333 3.1123 2.3666 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 4.6045 1.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8965 2.7791 1.9664 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0847 4.0706 -0.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1303 4.4441 -0.4495 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1961 4.6364 -2.8498 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6406 5.8556 -1.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6525 5.4145 -2.5508 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1605 6.3541 -2.8050 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0879 3.6815 -4.3736 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1089 2.3307 -3.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5017 3.5153 -3.3171 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7511 2.2270 -2.3025 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9733 0.3423 -1.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4756 1.9577 -2.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4762 0.7787 -1.5124 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8340 3.5560 -0.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2989 3.7122 -0.8537 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1508 3.8191 -2.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1158 2.2915 -1.8996 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6046 2.2753 1.5687 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1565 2.6299 0.7282 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4057 1.0383 0.5257 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3045 0.4332 1.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5303 -1.0052 2.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7353 -1.6989 2.4247 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7881 -3.0077 3.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6041 -1.9016 0.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3283 -3.4312 -1.6651 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5347 -5.7792 -1.7293 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0355 -6.5470 0.0025 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2898 -4.9947 1.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5617 -3.3518 1.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5664 -2.9365 3.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3368 -4.9389 2.1122 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0107 -5.1333 3.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6618 -5.2772 1.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2042 -6.0611 0.7811 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6279 -4.1557 -0.4064 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4085 -4.1558 -0.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3487 -1.2574 -1.2779 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6572 -0.5358 -1.1452 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6986 -0.6347 0.6086 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6994 -2.8459 1.6952 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4606 -5.2149 1.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8188 -6.1849 -0.7495 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4242 -4.8089 -2.7610 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6858 -2.5098 -2.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9811 0.9935 -0.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 9 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 16 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 24 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 1 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 42 50 1 0 50 51 1 0 51 52 2 0 51 5 1 0 31 26 1 0 39 35 1 0 49 44 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 0 3 57 1 0 3 58 1 0 3 59 1 0 4 60 1 0 4 61 1 0 5 62 1 1 6 63 1 0 9 64 1 1 10 65 1 0 11 66 1 0 11 67 1 0 11 68 1 0 12 69 1 0 12 70 1 0 12 71 1 0 13 72 1 0 16 73 1 6 17 74 1 0 17 75 1 0 18 76 1 0 19 77 1 0 19 78 1 0 19 79 1 0 20 80 1 0 20 81 1 0 20 82 1 0 21 83 1 0 24 84 1 1 25 85 1 0 25 86 1 0 27 87 1 0 28 88 1 0 29 89 1 0 30 90 1 0 31 91 1 0 32 92 1 0 35 93 1 1 36 94 1 0 36 95 1 0 37 96 1 0 37 97 1 0 38 98 1 0 38 99 1 0 42100 1 6 43101 1 0 43102 1 0 45103 1 0 46104 1 0 47105 1 0 48106 1 0 49107 1 0 50108 1 0 M END

Standard InCHIKey	WPYOCTODIOSRQG-WOXDTIJASA-N
Standard InCHI	InChI=1S/C40H56N6O6/c1-24(2)20-29-35(47)44-32(23-28-16-11-8-12-17-28)40(52)46-19-13-18-33(46)38(50)42-31(22-27-14-9-7-10-15-27)36(48)41-30(21-25(3)4)37(49)45-34(26(5)6)39(51)43-29/h7-12,14-17,24-26,29-34H,13,18-23H2,1-6H3,(H,41,48)(H,42,50)(H,43,51)(H,44,47)(H,45,49)/t29-,30+,31-,32+,33-,34-/m0/s1
SMILES	CC(C)C[C@@H]1NC(=O)[C@H](C(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	716.43	Volume:	753.254 ? Van der Waals volume.
Dense:	0.951	LogP:	2.328 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.368 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.984 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	40.0
TPSA:	165.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.268	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.879	Fsp³:	0.55
MCE-18:	98.71 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.675	Fluc inhibitor:	0.027 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.132 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.642 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.04

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.765	MDCK Permeability:	-4.832
Pgp-inhibitor:	1.0	Pgp-substrate:	0.782
PAMPA:	0.33 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.198
Plasma Protein Binding (PPB):	93.502%	Volume Distribution (VD):	-0.502
Fu:	7.698% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.192
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.003 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.623

Half-life (T1/2):

1.264

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.201
Human Hepatotoxicity (H-HT):	0.816	Drug-induced Liver Injury (DILI):	0.14
AMES Toxicity:	0.03	Rat Oral Acute Toxicity:	0.803
Maximum Recommended Daily Dose:	0.981	Skin Sensitization:	0.953
Carcinogencity:	0.007	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.722
Drug-induced Neurotoxicity:	0.998	Ototoxicity:	0.424
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.95
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.393
A549 Cytotoxicity:	0.07	Hek293 Cytotoxicity:	0.056
BCF:	0.571 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.329 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.607 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.169 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32477	Streptomyces sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1007/s00253-016-7823-y]
NPO32477	Streptomyces sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23013356]
NPO32477	Streptomyces sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28625960]
NPO32477	Streptomyces sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO45159	Streptomyces sp. MK600-cF7	Genus	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]

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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference
n.a.	n.a.	LogD	=	2.33	n.a.	PMID[27563399]
Canis lupus familiaris	n.a.	Papp	=	39.0	10'-6 cm/s	PMID[27563399]

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC604706 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	26256
0.1-0.2	22352
0.2-0.3	932
0.3-0.4	213
0.4-0.5	64
0.5-0.6	24
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC600414
0.9	High Similarity	NPC610520
0.8125	Intermediate Similarity	NPC604624
0.7	Intermediate Similarity	NPC603874
0.6667	Remote Similarity	NPC602452
0.6667	Remote Similarity	NPC607209
0.6629	Remote Similarity	NPC606523
0.6528	Remote Similarity	NPC603975
0.65	Remote Similarity	NPC603333
0.65	Remote Similarity	NPC604183
0.6477	Remote Similarity	NPC603858
0.6203	Remote Similarity	NPC607800
0.6184	Remote Similarity	NPC602763
0.6076	Remote Similarity	NPC604708
0.6049	Remote Similarity	NPC603507
0.597	Remote Similarity	NPC606917
0.5938	Remote Similarity	NPC605567
0.5833	Remote Similarity	NPC606945
0.5802	Remote Similarity	NPC602536
0.5729	Remote Similarity	NPC469903
0.5658	Remote Similarity	NPC608835
0.5641	Remote Similarity	NPC600996
0.5625	Remote Similarity	NPC476989
0.561	Remote Similarity	NPC602956
0.5443	Remote Similarity	NPC611487
0.5417	Remote Similarity	NPC603625
0.5366	Remote Similarity	NPC476990
0.5333	Remote Similarity	NPC602289
0.5315	Remote Similarity	NPC603629
0.5315	Remote Similarity	NPC606524
0.5294	Remote Similarity	NPC603846
0.527	Remote Similarity	NPC609985
0.5244	Remote Similarity	NPC601881
0.5147	Remote Similarity	NPC600121
0.5139	Remote Similarity	NPC609802
0.5125	Remote Similarity	NPC601721
0.5122	Remote Similarity	NPC610311
0.5116	Remote Similarity	NPC604279
0.5054	Remote Similarity	NPC473640

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC604706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3945
0.1-0.2	5028
0.2-0.3	175
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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